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“In a word no, for several reasons; firstly, it wouldn’t be ethical on a professional front. You came to me asking for advice and guidance, which I have given as your prison officer. To go along with your suggestion would cross the professional boundary and potentially cause both of us problems by blurring the basis of our relationship. Secondly, on a personal front, and this is to remain just between the two of us. I’ve only ever been fucked up the arse once and that was in the line of duty, so to speak.” I replied a little gruffly.

“Sorry Sir, I didn’t mean to speak out of turn, you don’t have to give me an explanation after all I’m the inmate and you’re the officer.” Jarek said suddenly all petulant.

“Look there’s no need to be like that. Personally I like you, but I think it’s best to keep things simple and I am just being honest with you as I have always been throughout our interactions. Right back to business, now you know the reason for your hole’s condition did you want to tighten it up or leave it be?” I asked.

“I think I’ll leave it be for the time being if you don’t mind, I can see that there may be some advantages to being able to accommodate large objects, at least I won’t have to fear advances from any of the larger endowed prisoners!” he said with a chuckle before adding “Oh, and by the way it doesn’t change how I feel about Marita you know.”

“Of course not, now if that’s everything I think it’s time we got you back to your cell before they think you’ve done a runner.”

With that I escorted him back to E-Wing and went for lunch, I was famished as well as parched (too much dribbling I think!). After lunch I submitted my report to Max detailing what had been said, what happened and the results before resuming my normal duties for the afternoon which passed without incident.

WEDNESDAY 7TH APRIL 2010

Dear diary, another interesting day at the office and one that has given me much to think about! This morning I turned up for work as normal, made myself a coffee and checked my pigeon hole for mail. Normally it is empty but this morning there was an official looking envelope with just my name on it. Sitting down on a nearby chair I tore open the envelope to see a note from Liam asking me to see him immediately at the beginning of my next shift.

Having spoken to George and asked him to go on the morning prison rounds without me (showing him the note as I did so) I made my way up to the Governor’s office and knocked on the door wondering what he wanted to see me about.

“Come in!” called the familiar voice of Liam.

As I walked in and smiled in his direction he gestured for me to sit down at the desk in front of him, I was a little surprised to find that there was only the two of us in the room with no sign of Max or Adrian. When I made a comment to this effect I was told that this was a confidential meeting and was to be kept secret until a definite outcome had been reached. I was intrigued by this statement and asked him to elaborate.

“Okay Sam, I will explain. Do you remember the post-punishment meeting we had with Tyler? You do? Good. Well I’ve been doing a lot of thinking since then and the report you submitted to Max yesterday crystallised the matter for me and I’ve decided to put my plans into action but I wanted to run them past you for your input. I have decided to create the role of ‘Volunteer Punisher’, one for each wing, they will be responsible for the implementation of inmate punishment under the new rules introduced in March under the close supervision of the Volunteer Co-ordinator. It will serve two purposes, firstly it will free up our own officers and secondly it will lock our tougher prisoners into a role which should restrain their more unruly tendencies.”

“Right Sir, but where do I fit in your plans and why do you need my input?” I asked, still none the wiser.

“Well, I am seriously considering making you the Volunteer Co-ordinator. If you are interested in this role I will elaborate further, there’s no pressure but I am very impressed with your attitude and popularity with the inmates. I believe you are an ideal candidate.”

“Thank you, it’s fair to say that I am interested but what is involved and will it affect my normal duties?” I replied deep in thought.

“Once I have assessed your training needs and brought you up to speed, then you will be responsible for the selection, training and supervision of the volunteer punishers. You will also be responsible for their punishment should they break the rules of their roles. As you are no doubt aware the prison philosophy is to lead by example, so we will expect you to do so too. Your behaviour must be exemplary while on duty and be able to perform all the tasks you expect the inmates to do. I have drawn up for your reference a manual outlining the volunteer role and the sexual activities they will have to be adept at. As to it affecting your normal routines it is impossible to say at this stage as we have no idea about the amount of time the role will require. This is something we can assess as we go but there’s no need to worry, we have no intention of overloading you!”

“Sounds good to me, I’d love the opportunity to increase my experience and value to the prison service so please count me in. Is there any chance of seeing the training manual?”

Beaming broadly Liam reached behind him and pushed a posh looking presentation black folder with my name on it, I guess they had every intention of me taking on the role. I guess my ambition must be a little predictable?! Opening the front cover I scanned the introduction and turned to the volunteer role section and started reading avidly. From the corner of my eye I could see Liam watching me with a slight smile on his face, ignoring it I carried on reading. I was intrigued to read that the volunteer’s uniform was to be simply a red beret and a leather belt worn around the waist to which attaches two small tubes, one of KY and the other Crisco. No other items of clothing are permitted.

Looking up I asked “Will I be expected to wear this uniform and what about the inmates who are not permanently naked?”

“Absolutely not, your uniform is that of a prison officer, that doesn’t change in any way. As to the inmates, if they want to be volunteers then they have to wear the uniform, there will be no exceptions on this point. The uniform is designed to set them apart from the other inmates, be distinctive but at the same time not give them too much authority. After all compared to prison officers and the majority of inmates they will still be virtually naked.”

I nodded my understanding and carried on reading through the manual, I was just getting to the section about sexual activities when the phone rang breaking my concentration. Liam spoke on the phone for a couple of minutes, hung up and announced that events had overtaken us

“Please feel free to take the manual and read it at your leisure when you get home, but please keep it to yourself as the contents are confidential. I have scheduled your assessment for first thing tomorrow morning, I will get Max to reschedule your morning timetable to accommodate the assessment. Okay then? I’ll see you tomorrow morning in Richard’s consultation room”

With that the meeting was clearly over so I stood up, shook Liam’s hand and made my exit with my folder under my arm. I discreetly put the folder into the boot of my car for reading when I get home and went back to work.

This evening I made myself comfortable and read the manual from cover to cover. It was very well written and covered all the areas I could think of when it came to the volunteers and the role. However when it came to the sexual activities expected to be carried out I couldn’t believe what I was reading, it was very graphic and left nothing to the imagination! I must admit I was sporting a hard on until I remembered that Liam had told me that I would be expected to be an expert in all areas of the manual both on the giving and receiving as I would be training the volunteers.

Ho hum! I could always back out but that would be the coward’s way, after all I have been happy to undertake some of the activities listed in the manual so why not go with the flow and see how far I can stretch my boundaries? Not only that, my standing in the eyes of Liam and his team would be diminished and possibly jeopardise my shining new career. I went to bed wondering what tomorrow would bring.

THURSDAY 8TH APRIL 2010

Oh diary, where do I begin? It has been one hell of a long and exhausting day. Starting at the beginning would be the best place I guess, here goes.

Got up early, showered and shaved in preparation for my assessment with Liam, had breakfast and got to work twenty minutes early. I clocked on, checked my pigeon hole and then made my way over to Richard’s (the prison doctor) consultation room in the medical centre. Knocking on the door I waited for an answer as I could hear muted voices on the other side. Finally I heard a “come in” and I opened the door and went in to be greeted by Liam and Richard who were sitting round Richard’s desk discussing what looked like a medical form much like we had completed for the inmates during the post punishment sessions.

“Ah do come in Sam, sit on the couch for a moment please while I explain what this morning’s assessment is going to consist of” Liam said looking up from the paperwork.

I did as I was told without comment.

“Did you read the manual I gave you yesterday?” Liam asked.

“Yes Sir, from beginning to end. It certainly made for interesting reading and quite an eye opener!” I replied smiling.

“Indeed! I’m glad you liked it. Richard is going to do the usual medical checkups on you, we will then assess your body’s capabilities so we can determine what exercises you will need to undertake in the following days. Okay so far? Good. As before all we ask is for you to trust us, follow instructions and know that whatever you are asked to do is for your own benefit. Right let’s make a start. Firstly, would you please remove all of your clothing; you can place them on the chair in the corner and then stand facing us by the couch.” Liam said with a deadpan face.

I remembered what he had been like during the interview process and how he could change from being affable one moment to very hard and stern in the blink of an eye. He wasn’t the Governor of the prison for nothing! So without hesitation I disrobed as quickly and efficiently as possible, neatly placing my uniform and underwear where indicated. In less than two minutes I was standing in front of the couch, naked as the day that I was born with my hands behind my back (well I wanted to appear as relaxed as possible).

Richard then spent the next ten minutes going over my body with a fine tooth comb (I don’t mean literally) noting down every statistic, measuring my heart rate, blood pressure, peak flow etc. You name it he checked it with great care and fed the results back to Liam who faithfully wrote them down on the form. When he was satisfied he left the room for a moment before returning with a familiar contraption. I gulped quietly to myself, it was the portable colonic irrigator and I had seen this device in operation only nine days ago on (or rather in) Jarek so I knew what was coming next!

“Sam” Richard said “please turn to face the couch and bend over resting your elbows on it, then spread your legs apart as far as is comfortable.”

I did as I was told without saying anything, what was there to say?

Before long I felt greasy fingers feel between my cheeks and explore the length of my crack before finding their target, my anus. Then with one deft movement I felt a glob of grease being pushed inside and a couple of fingers massage my ring before they too were pushed up my rectum. I groaned in spite myself and was told by Liam to relax as much as possible, it would make it a lot easier for me if I did.

I was just getting used to the intrusion when I felt the fingers being removed to be replaced by the cold metal douching tube making my hole twitch in response. I looked over my shoulder out of curiosity; the tubing looked a lot smaller than it felt! Richard looked up at me and winked before returning his concentration to the task at hand. He switched the motor on and the irrigator started humming and vibrating, within seconds I felt warm water flow up into my rectum. Just when I started to feel full, the flow reversed and the water/faeces mixture left my body before the tube was pushed further up inside me, from the feel of it my inner ring had been breached and the tube travelled up into my bowels. It felt strange, not exactly painful but not comfortable either. I can only estimate that this went on for about fifteen minutes before Richard announced that the whole of the tubing had been inserted and no more faeces was coming out. He then slowly withdrew the tubing, I was relieved when it finally left and my hole was once more free to close up.

“Well done Sam, that went very smoothly” Liam announced, stepping over to me as Richard removed the machine from the room. “Now I would like you to climb up on the couch, lay on your back, bring your knees up to your chest and hold them in position using your arms.”

“Yes Sir.” I said and did as I was told.

“How are you feeling so far?” Liam asked as he snapped on a pair of latex gloves and started to grease them up.

“Okay, a little exposed. It’s not the first time I’ve been in this position Sir, Richard can vouch for that.” I said trying to sound as confident as possible and grinned in Richard’s direction.

“He’s right” Richard confirmed. “I had him like this just about a month ago in fact.”

“Good. I am now going to assess your anal ring’s tightness. You are of course familiar with the process because I know you have carried out those tests yourself on the inmates during the post-punishment assessments. I won’t waste breath explaining them to you, I am going to get straight down to business, so nice steady breaths Sam, try to relax and enjoy the experience!” Liam said chuckling as he smoothly slid one finger up my exposed rectum.

I didn’t actually find one finger uncomfortable; I guess being fucked by Sayeed put paid to being tight in a virginal way. I closed my eyes and practised relaxation methods in head which helped enormously when Liam inserted two fingers, there was distinctly less room available for them. He is skilled at his art I thought because I expected him to immediately try for three fingers but no, the two fingers slowly rotated and pushed in and out of my hole relaxing my ring remarkably quickly. As I felt three fingers attempt an entrance all thoughts of mantras and relaxation methods flew out of the window, I was now getting curious about the action going on at my backdoor. Lifting my head I looked between my knees to find that I couldn’t see very much as my cock and balls were neatly blocking my view so I let my head fall back onto the couch. All the while those three fingers were rotating and pushing inwards but my ring was now at full stretch and I was groaning loudly in protest.

“How much have you got in there because I don’t think I can take any more Sir” I asked with a slight trace of worry in my voice.

“I have currently got three fingers fully inserted but don’t be alarmed I am stopping there, for today at least. We have a lot of work to do on your hole to get it in shape for the task ahead. There’s just no way you can train the volunteers at present, this because you cannot demonstrate all of the techniques and you will risk serious injury if you attempt to. Starting from tomorrow morning, you are to come straight here at the beginning of each shift and we will start your training in earnest. Do you have any questions?” Liam asked as he withdrew his fingers, removed his gloves and wiped his hands on some tissue.

“No I don’t think so.” I replied quite truthfully.

“In that case, you’re free to wipe yourself clean, get dressed and return to normal duties for the rest of the day. Don’t forget Sam, none of this is to leak out yet.” Liam announced all smiles now.

“Thank you, I won’t forget.” I replied rolling of the couch and walked rather stiffly over to the box of tissues to wipe my bum clean of all the grease before getting dressed as instructed.

Back of the prison wing George tried fishing to find out what I had been doing but despite his best attempts I managed to avoid any slip ups and evaded his traps. Eventually he gave up and the day carried on as normal. At long last my shift was over and all I wanted to do was to have a long hot shower and vegetate in front of the TV with a beer or two or maybe surf the internet for an hour or two.

It wasn’t until I was halfway home that I remembered that I was supposed to be going jogging with Aaron and Jason, damn! Perhaps they might cancel and I will still get to have my evening on the couch after all. No such luck! At 7.00pm on the dot there was a ring on the bell and I opened the door to be greeted by two grinning young men telling me I must be getting past it as I took so long to answer the door. Past it indeed! I’ll show them I thought to myself. While they sat in the living room watching the TV I quickly got changed into my running gear, then we were off for a deliberately brisk jog twice round the park. Mission accomplished, I had two exhausted young men panting like there was no tomorrow by the end of the jog, while I had hardly broken into sweat.

“Never mind boys” I said with just a very slight smug tone in my voice “I’ll get you as fit as an old man like me before much longer.”

“Ha ha ha” was all they could manage between gasps for breath. Walking back to my flat we had to stop a couple of times due to cramps and stitches but eventually we got there and their mood lifted a little. As I turned the key in my door they were back to being their joking selves.

I let them shower first like I did on Monday, this time Aaron went first as he had to get home early to baby sit. By the time Jason returned from his shower with as usual a towel wrapped round his waist, Aaron was dressed and flying out the door with a “See you guys on Sunday at the Leisure Centre, bye!”

I decided it was time for my shower and invited Jason to make himself comfortable while I took my shower, he accepted my invitation with a nod and sat down on the sofa with the TV remote control. Five minutes later I was in the shower soaped up and just about to rinse off when there was a knock on the bathroom door and before I could call out I heard the door open.

“Sorry Sam, I know you’re having a shower and I really hate to invade your privacy but I’m bursting for a pee and I can’t hold on any longer. Do you mind if I quickly use the loo? I won’t be a minute.” Jason said with a pleading tone in his voice.

What could I say? He was already in the room.

“Sure go ahead Jason. Just be careful where you look, you might see more than you want to!” I said trying to be as jovial as possible as I rinsed the soap out of my hair and eyes.

“Don’t worry about me, I’ve seen loads of naked men, don’t forget I’ve always played loads of team sports and you get to see plenty in the changing rooms afterwards.”

I carried on rinsing off, I kept my eyes closed because I have this hatred of getting soap in my eyes (have had ever since I was a kid). By the time I turned the shower off I had expected the bathroom to be empty again, but no Jason was still very much present and was even offering me my towel! At a little loss for words I simply took the offered towel with a smile and started to dry myself off. There was little point in pretending modesty when he had just about seen everything there was to see. I couldn’t help but have the feeling that he was enjoying seeing me naked so I asked him outright.

“Jason, do you always hang around in the bathroom when someone is having a shower?”

“Guilty your honour!” he said without hesitating. “Unlike Aaron’s old man, mine is very liberal. Ever since a kid we, that is my dad and brothers, have always been very relaxed about our bodies, none of us think twice about walking into the bathroom when another is having a shower or using the loo. Okay with my mum it’s a bit different but then she has her own en suite bathroom which makes things a lot easier. She’s even used to us walking around the house naked, okay that’s normally after a night on the tiles or during hot weather admittedly. I guess that is why I feel so comfortable here; you and dad are very similar in some ways. I hope I haven’t made you feel uncomfortable by acting like this and please don’t say anything about this to Aaron because he wouldn’t understand and he’d only get the wrong end of the stick.”

“Fair enough, I hear what you’re saying, however I would prefer that you be upfront about things like this, people can get the wrong idea you know.”

“Okay Sam, I hope I haven’t offended you at all.” Jason said contritely.

“Offended? No not at all. Surprised? Well, yes I guess so.” I replied as casually as I could manage.

Well, I suppose I must be a bit of an exhibitionist (as if you hadn’t guessed by now) and decided that I would play a game with Jason to see if my feelings were correct or if he was being totally genuine and innocent in his actions. Having towelled myself dry I sprayed some deodorant on and then walked out of the bathroom, still starkers heading towards the kitchen. Behind me I could hear Jason’s footsteps following me not too far behind. Judging him to be visual range I opened the fridge door and reached in for a couple of cans of beer which were on the bottom shelf at the rear. In order to do this without crouching I had to spread my legs a little and bend at the waist, unfortunately this action exposed my hole and my tackle dangled nicely in the space between my thighs. I heard a stifled murmur so having hold on the cans I quickly stood upright and turned round in one smooth movement, catching Jason by surprise. There he stood, leaning against a work counter, feet crossed at the ankles, towel around his waist and just the beginnings of a tent pole!

“Would you like a beer? Can I offer you anything else?” I asked as innocently as possible.

“Anything else?” Jason replied, voice raised just a little. Something must have been lodged in it because he had to clear his throat before continuing “What do you have in mind?”

“Dunno really, I’ve got some chips in the freezer, or I can do us a salad. Actually, if you want to have a look in the cupboards and let me know if there’s anything you fancy. Personally I’m going to have a salad as I have to watch my weight these days, I don’t want to get belly or fat bum!” I patted both as I said this.

I sensed a deflation in him as he realised I wasn’t suggesting what he thought I had. His towel still had a slight tent pole but he ignored it as he stood up straight and said “If a salad is good enough for you then it’s good enough for me, after all it’s me who needs to lose the weight. Look at you, there’s not an ounce of fat on you anywhere!”

Smiling in acknowledgement I set about preparing a ham salad, not giving my nakedness another thought but making sure that I struck suggestive poses wherever possible. Jason didn’t say anything untoward but his tent pole never went down one little bit. Once we had eaten we moved into the living room and watched the 10 O’clock news on ITV. I sprawled out on the sofa, making sure that my tackle was nicely displayed and Jason sat in the armchair, for some reason he seemed to have trouble concentrating because out of the corner of my eye I noticed he kept glancing in my direction. After the news he decided that he needed to be getting home and so retrieved his clothes and got dressed before bidding me good night. Poor boy he just couldn’t help but look at my body one more time as he shut the door behind him, on the other side of the door I was grinning to myself knowing that my intuition had been right all along.

FRIDAY 9TH APRIL 2010

Last day of the week thank God! My poor hole will be getting a rest for a couple of days, from prying fingers at least.

Richard and Liam were waiting for me in the consultation room as I arrived, and it was straight down to business. I was told to strip and assume the position for being cleaned out. I won’t bore you with the details but it was exactly the same process as yesterday, although a little easier as I knew what to expect. The I was told to hop onto the couch but this time stay on all fours with my head on my hands (actually this position was identical to the one I got Jarek to assume last Tuesday).

It wasn’t long before I felt latex covered fingers tickling my anus, making me wriggle a little before I felt the familiar sensation of cold Crisco being pushed into my hole and smeared all round it. First one finger went in, then two, all the time they were rotating and massaging the anal ring. Their movement was hypnotic and I was almost in a trance when I felt a third finger join them. I shifted my weight a little and was asked if I was okay, all I could do was respond with an affirmative grunt. The three fingers massaged their way for what seemed an eternity, my hole was getting looser and I was just beginning to feel restless when they were withdrawn and I was told to climb off the couch and stretch my body for a minute while Richard fetched the next piece of equipment. Did I say piece of equipment, more like a cross between an item of clothing and an instrument of torture!

As I was limbering up, touching my toes and then the ceiling etc, Richard walked back into the room carrying what looked for all the world like a leather thong. I said as much to him and he nodded in agreement.

“You are right Sam. That is exactly what it is, although not one you are able to buy in Marks & Spencer! I just have to connect the attachment and we’re ready for your first fitting.”

Fitting for what? I asked myself. I didn’t have long to wait before I found out. Richard reached into a drawer and pulled out a box of what looked like black rubber objects, light bulb in shape with a metal screw thread at the neck end. There followed a brief discussion between Liam and Richard before an agreement was reached and the required object selected. Richard then picked up the throng and appeared to screw the “light bulb” onto the narrow part of the thong. Sometimes I can be so thick because I still didn’t have a clue about what was coming next! When he was satisfied that all was in order he knelt down on the floor and asked me to stand in front of him facing away, which I did. He then asked me to step into the outstretched thong, which I did, only then did it occur to me what the bulb was for.

“Please pull the thong up to your waist and maintain that position.” Richard instructed.

I did as I was told, then I felt a hand reach between my legs and take hold of the bulb before placing it against my anus and gently pushed it upwards. It felt bigger than it looked and was certainly bigger than the three fingers I had just accommodated.

“Spread your legs a little and push out as if you’re about to drop a log.” I heard Richard advise from behind me.

Well that paints and interesting picture I thought, but again did as I was told. All I can say is it worked, by spreading my legs I ended up squatting slightly and as I pushed out I felt Richard apply more pressure. In less than a minute the head of the bulb made its abrupt entrance into my rectum and my ring clamped shut tight around the neck.

“Aaaaaargh! That hurt!” I groaned.

“It’s okay, your ring will calm down in a minute or two, it’s just not used to stretching that extra bit” Liam assured me. “What we want you to do is to wear this thong when you go to bed each night, leave it in place all night and then remove it in the morning, okay?”

“Um, yes, okay I guess. Can I take it out now?”

“Is your anus still aching?” Richard asked.

“It is a little, I also feel very full like I need a crap badly.” I admitted quite frankly.

“In that case you need to keep it in a little longer to allow your body to adjust to the intrusion. Please climb up on to the couch and lay down on your front as if you’re going to have a massage, then RELAX.” Liam instructed.

As I lay there relaxing doing my best to ignore the object within, I felt fingers slip underneath the thong and explore the boundary between the neck of the bulb and my ring. For a couple of minutes they massaged all the way round several times before withdrawing and grasping the neck. I then felt the bulb being gently tugged, then pushed in further, wiggled around and then the cycle started again.

“How does it feel now?” Liam asked as Richard continued his ministrations.

“Okay actually thanks, I no longer feel any discomfort at all which I am surprised about” I replied.

“Good, that is progress indeed. We’re now going to take it out now so just relax and as before push out gently.” Liam said.

It came out with a plop, slightly uncomfortable but certainly not painful like it had been going in. I was then told the training session was over, I could clean myself up and get dressed. As I was dressing Liam reminded me that I was to wear the thong & insert the bulb each night until the next training session on Monday. Then it was back to work, this time George didn’t bother asking where I’d been as he knew I wouldn’t say.

This evening just before bed time in the privacy of my own bathroom I tried to insert the bulb again. Although I was using the same grease that Richard had given me, this time it just seemed so much harder! No matter how I tried it just wouldn’t pass my golden gates. I was getting very frustrated. Then I recalled the trick about squatting and pushing out at the same time, I am so glad no one was there to watch, it was all rather undignified. There I was squatting over the toilet with rubber bulb in one hand, the rest of the thong in the other hand to prevent it trailing in the water and me pretending to have a dump! Mind you, once again the trick worked, in it popped as quick as you like, but boy did I break out in a sweat and groan. It wasn’t so much painful more like a throbbing toothache which slowly faded away. With the bulb inserted I stood up and pulled the thong on and made my way to bed. What I do in the name of duty.......

SATURDAY 10TH APRIL 2010

Dear diary, if I am honest I thought today was going to be one of those unremarkable days but actually it ended on a high note so I guess I can’t complain.

Woke up this morning after a good night’s sleep, I had totally forgotten about the thong and bulb so was a little confused by the feeling as I normally sleep in bed with just a T-shirt on.

Went to the bathroom to remove it using the same trick as last night, I was surprised to find that my ring really didn’t want to let go of it but after a bit of huffing and puffing it shot out along with a load of shit behind it – major yuk! Not the best sight or smell first thing in the morning; I retrieved it from the pan and gave it a very thorough washing along with my arse which felt strangely loose. It was, I could easily stick two fingers up inside with no problem or lube!

Having recovered from that shock I got dressed, shaved, had breakfast and went shopping for the mundane things in life like food and groceries. Then home to more mundane things like housework, washing and ironing.

By late afternoon I was totally bored so I called Tom to see what he was up to. He said he was glad that I had called because he and Chrissie were entertaining Mike, Aaron and his wife Sally, Jason and his girlfriend Kirsty this evening and if I could join them it would make the numbers even. I leapt at the chance to have dinner with my two best mates, they’re always good for a laugh and Chrissie is lovely as is Sally. Kirsty I don’t know but knowing Jason she is bound to be pretty and educated. We chit chatted for a while before Chrissie came on the line and begged me to come as we hadn’t seen each other since the wedding, that was settled then!

Eight O’clock on the dot finds me knocking on the front door, which opens to reveal a laughing Chrissie (already half cut) holding a glass of red wine. She squeals in delight (that’s Chrissie for you) and gives me a hearty one-handed hug before dragging me inside and shutting the door behind me. By the sound of it I’m the last to arrive as the house is buzzing and rather noisy. I tell Chrissie that she is one swell looking lady in that little black dress, which only causes her to giggle all the more and informs me that my smooth tongue and an eye for the ladies hasn’t changed one little bit over the years (if only she knew the half of it!).

The sound of our voices in the hallway attracts attention and Tom sticks his head round the living room door, shouts hello and tells me to join the crew in the living room while the ladies finish preparing dinner. I do as instructed and as I walk into the room I am greeted by a united “hello” from Mike, Aaron and Jason all trying to offer me a can of beer or glass of wine. Holding my hands up in mock surrender I take a can of beer and proceed to make small talk with them until dinner is announced.

Dinner (or rather a three course banquet) was truly scrumptious, for starters it was homemade potato and leek soup with croutons. Main course was roast duck breast served with a medley of green vegetables, rosti potato cakes and a rich port sauce. For dessert homemade vanilla ice cream marbled with dark chocolate and a raspberry sauce followed by the obligatory coffee and mints.

It was during the coffee round that attention turned towards me and I received a good natured grilling over my current job as a prison officer. I talked about my role and the inmates I came into contact with (without revealing their real names) and some of the incidents that I had encountered. I successfully managed to avoid mentioning the sexual nature of some of my encounters and the new prison rules etc. I also managed to avoid any reference to the fact that I was no longer 100% heterosexual in my thoughts or activities. After what seemed like ages the attention turned to physical fitness and finally Kirsty came out of her shell. She thanked me for taking Jason under my wing, although he has only just started his training with me she has already noticed a difference. He has started to eat more healthy food, drink less alcohol (this night being an exception) and has been religiously doing all of the exercises I had given him. She thinks in the right light she can make out muscles underneath his belly! This brings resounding laughter from all except Jason who pulls a hurt expression before throwing me a sly wink. Then Sally nudges Aaron and makes it clear that he has no room to laugh as his middle is beginning to spread! Tom regains control of the situation by expressing the fact that really all the guys in the room (except me, of course) could do with a little more exercise and less girth round their middle, perhaps Mike and he could join the rest of us on Sunday at the swimming pool and see how they get on. I thought this was a splendid idea, but what about the ladies though? By the end of the conversation we were going to be a group of eight in the pool on Sunday, I wonder if we can get a group discount?

I finally staggered in through my front door at about 1.30am (technically Sunday I know but I don’t count it being the next day until I’ve been to bed and woken up again) and was all set to collapse into bed when I saw the rubber bulb waiting on the side for me. I ummed and aahed over it, thought sod it one day won’t make any difference, then changed my mind and picked it up on the way to the bathroom.

I sat on the toilet and emptied out as best I could then greased my arse up and also the bulb. Perhaps it was the alcohol in my system or my deadened sense of time but it (the bulb) seemed to disappear up inside me more easily and quickly than I expected. It did have one unexpected side effect, it gave me a raging hard on as it gently rubbed and banged against my prostate from the inside. There was no way I could go to bed like this, so with one hand feeling the neck of the bulb and my ring clamping hard round it, and the other wrapped round my cock I jacked myself of to a pretty earth shattering orgasm over the bathroom basin. Deciding now enough was enough I really needed to get to bed I washed myself off (and the basin), pulled up the thong and made my way to the bedroom where I quickly succumbed to oblivion.

SUNDAY 11TH APRIL 2010

If I’m honest diary, today didn’t actually start until about 11.45am when I woke with a jolt to the sound of my phone ringing about six inches from my ear – not a good way to start the day if you’ve got a little bit of a hangover....

I was just a little groggy when I picked up the phone and mumbled a hello down the line only to be greeted by the chirpy tones of Chrissie.

“Morning Sam! I just thought I’d give you a quick call to make sure you got home safely & that we’re still on for the swimming session this afternoon. How’s the head this morning?”

“Urrr morning Chrissie, I think, what time is it? Yeah got home okay and yes I’ll be there at the leisure centre at 2pm as agreed! My head is still on my shoulders but feeling distinctly tender, I guess that will teach me to finish up that last bottle of red with you... how’s your head by the way?” I asked as I came to, slowly.

“I’m just fine, thanks” Chrissie assured me “must get on, still got some clearing up to do before we meet up. As to the time, it’s nearly mid-day. See you shortly, byeee!”

And then she was gone. Just as well she woke me up as I didn’t have all that much time to get spruced up etc. First things first, into the bathroom to shower and remove a certain object. Crikey, my arse must be getting like a bucket because it’s getting easier to take the bulb out, I didn’t have to squat over the toilet and strain, I simply started to squat down and as I did so it popped right out with little discomfort. Curiosity got the better of me, I just had to assess the damage to my hole, not only did two finger slide right on up inside with no trouble but so did three! Progress indeed, I’m sure that Liam will be pleased. However I had no time to dwell, I quickly showered and shaved before getting dressed and packed my bag with my swimming gear.

I got to the leisure centre just before 2pm to find Jason and Kirsty waiting outside for me and the others; we made small talk and recounted the events and conversations from the previous evening. Throughout our conversation I monitored discreetly Jason’s behaviour towards me, but he acted impeccably and not once did he act in anyway other than being Kirsty’s partner, to my relief. Ten minutes later the others had arrived and we made our way into the changing rooms.

With the five of us (Tom, Mike, Aaron, Jason and myself) getting changed it was a very relaxed affair, even Tom seemed at ease and managed to joke around as we undressed and got into our swimming trunks. Privately I had to agree with Tom, both he and Mike were carrying a decent sized spare tyre round their middles. They will definitely need to go on a diet and exercise regime before they can join Aaron, Jason and myself jogging round the park on a Tuesday and Thursday. An hour later after a mixture of hard swimming and relaxed messing around in the water the eight of us are sitting round a table in the cafe overlooking the swimming pool. I was lost in thought when I felt a sharp nudge in my ribs bringing me back to the present.

“Well Sam, what do you say? Are you up for it?” Aaron asked with a slightly exasperated tone to his voice.

“Up for what?” I asked in all innocence.

“Having a last lad’s night out this Friday before we cut out all the booze and grub as part of our diet and fitness regime” Tom explained.

“Yes, sounds good to me. Is it down the Kings Head shall we make it a special night and go into town?” I asked the group in general.

“Oh it’s got to be town if it’s going to be our last night out for a long time!” Jason cried out all enthusiastic like a big kid.

“That’s decided then” Chrissie announced “girls we’re going to paint the town red too! Kirsty and Sally, get your thinking caps on, we have four days to plan our night out.”

Shortly afterwards the conversation naturally dried up and we went our separate ways.

MONDAY 12TH APRIL 2010

Back to work already, oh how the weekends pass so quickly. The alarm clock went off and I swung into action on autopilot, even removing the rubber bulb from its night time lodging in my rectum had become part of my routine. I hate to admit it but I could insert and remove it with ease....

At the prison I made my way directly to Richard’s consultation room and knocked on the door before walking in to find that Richard was alone. He greeted me with a warm smile and explained that it would just be the two of us to start off with as Liam had been called away at the last minute but he hoped to join us later. With the preamble over we got straight down to business, I stripped naked and Richard cleaned me out thoroughly using the portable colonic irrigator. Then having climbed onto the couch, kneeling on all fours in the usual position Richard examined my anus to assess my progress with the rubber bulb. I felt him smear the Crisco round my hole and then fingers moving around the outside and inside of it. The movement was constant and I had difficulty keeping a track on how many there were and what they were doing, it all became a pleasurable blur.

“Well Sam, I can see that you have followed our instructions and the result is very pleasing indeed. You should be proud of your achievement, your progress is excellent.” Richard announced as he withdrew his fingers from me.

“Thank you Richard, I must admit it was not easy at first but by this morning I really become accustomed to it and I was even finding its presence pleasurable in a weird kind of way. When you say I have progressed, by how much and what is the target you have in mind?”

“I’m glad you are finding the insertions pleasurable, that is one of our objectives, you will then be able to pass this knowledge on and be able to demonstrate it to the trainee volunteers at the appropriate time. As to progress, on Friday morning you were just able to take three of Liam’s fingers, however this morning you were able to easily accommodate three of my fingers and so I am moving on to the next step of your training. By the end of this morning I expect to be able to insert at the minimum four fingers, but hopefully depending on your ability and willingness to stretch I will be able to insert the whole of my hand into your rectum. Then for the next couple of mornings we will be working on depth before moving onto width. How does that sound? I bet you’re glad you asked that question now aren’t you?” Richard said with a hearty chuckle.

“Mmm I think I will reserve judgement on that for now, if you don’t mind. To be honest, I’m not in a position to protest; after all I’ve had my fist up Jarek a couple of times now. He’s survived the experience intact and even seems to enjoy it despite being straight.” I replied looking over my shoulder at him as I spoke.

“Okay, shall we carry on then? Before we do, are you comfortable or do you need to stretch your legs because it may be some time before we can stop again.” Richard asked.

It was a good idea so I climbed down off the couch and did a number of stretching exercises under the watchful gaze of the doctor. After five minutes I climbed back onto the couch and assumed the customary position.

“Sam, I’m going to start stretching your anal ring further than it’s ever been to date, so relax as much as you possibly can. If at any time you feel pain you must let me know immediately. Discomfort is to be expected but pain is a big no no, do you understand?”

“Gotcha, I will do.” I mumbled with my face half buried in my hands.

Almost immediately I felt more Crisco being packed into my rectum and then pushed further inside by a couple of fingers, I could feel the grease softening and melting because it’s presence seemed to diminish gradually until I could no longer sense it. Unlike the fingers! There were definitely three fully inside me constantly twirling around, pushing in and then pulling out and repeating the whole cycle. I gave up counting after the fifth cycle and my mind began to wander all over the place. I was broken out of my trance with the sound of the door opening and Liam’s voice greeting us both.

“So guys, how is the patient doing?” Liam asked laughing at his own joke

Richard, without slowing or stopping his hand movements in any way, proceeded to discuss his findings and plans at great length. It was all very technical and made me feel like an object or piece of stock, as a result I quickly lost interest and started drifting away again. That is until I felt a hand reach beneath me and take hold of my bollocks, giving them a quick massage before moving onto my erect cock. I didn’t even realise I had an erection.

“So Sam, I see you’re not adverse to the treatment the good doctor has been administering, this is excellent news and I hope you are as proud of your progress as we are. You will make a very good Volunteer Co-ordinator, as you have a prison officer, your can do attitude has not gone unnoticed I can assure you. Just out of interest, do you know how many fingers are currently in your hole at the moment?” Liam asked.

I tried to count Richard’s fingers which were still moving round in their usual cycle but my anus had become so desensitised that I had no option but to guess so I said “Three?”

“No, Richard actually has four fingers fully buried inside and from where I’m standing I don’t think it will be much longer before his thumb will be joining the other fingers.”

“That’s good” was all I could think of to say.

After what seemed an eternity I began to feel a new sensation in my rectum, it was one of fullness and my ring felt tight like it hadn’t felt since the day I was fucked by Sayeed. Richard’s hand had stopped its motion and was stationery, no, that’s not quite true, it was moving very slowly if at all in the direction of my rectum. My ring was finally putting up some resistance and so he applied a little more force to his pushing resulting in me moving a little up the couch.

“Sam” Liam said with a serious tone to his voice. “I want you to breathe deeply and do your best to relax as much as possible, we’re almost there.”

“Yes Sir.” I said through gritted teeth as it was getting distinctly uncomfortable now.

Then all of a sudden as I was doing as I was told, it hit me like a tidal wave, drawing an “aaaghh!” from my lips, my ring gave up its resistance and allowed Richard’s coned hand to slide inside, as it did so his hand balled into a fist and my ring clamped shut around his wrist.

“Jeez! Is that really your fist inside me?” I growled.

“Oh yes, it certainly is.” Richard confirmed “I’m going to hold it still so that you can get accustomed to its presence then I’m going to move it around and I want you to tell me how and what you feel okay?”

“Okay” I said panting heavily “For a start it felt like my ring was on fire, then I felt I desperately needed to go to the loo. Both of these sensations are fading now leaving me feeling very full down there but not unpleasantly so. As you move your hand around I can feel it both from the inside and also the outside which seems very strange indeed. Ah, now you’ve just brushed my prostate because I’ve felt a surge of blood to my cock which had started to go soft again.”

“Excellent feedback Sam, you’re really in the zone now. Keep those memories secure because you’re going to need them when training the volunteers so that you can tell them what to expect.” Liam said before continuing “In a few moments Richard will start to withdraw his fist, there may again be some discomfort at the point of exit, but as with the rubber bulb the more you do it the more you get accustomed to it and the less discomfort there will be.”

Richard then added “Start breathing deeply, relax and imagine you are going for a dump, push a little but not too much. Ready? One, two, three here we go.”

“Eeeeeeyooow!” I cried as Richard’s hand was released from my hole, leaving it gaping wide before it slowly closed up again. I collapsed slowly onto the couch in exhaustion, sweat pouring from every pore in my body. I laid there motionless, my mind was all over the place as if I’d had too many pints on a Friday night, however my peace was abruptly disturbed a couple of minutes later by a pair of hands pushing my thighs apart and then exploring the crack between them. Before long once more I felt fingers exploring my hole and then smoothly glided on inside; my poor ring was too exhausted to put up much resistance. At the same time Richard lifted my hips and slid a pillow underneath me to raise my bum slightly into the air and provide Liam with easier access to my hole.

“Well done Sam, that’s it, push out a little, welcome my fingers. Great! That’s now four fingers inside, let’s tuck that thumb in behind them and see if you can take my hand too.” Liam encouraged me.

I backed onto the invading fingers as best I could while pretending I wanted to evacuate my bowels, the technique seemed to be working because before very long I felt the cone of his fingers getting wider than ever and then came that sticking point when the widest part is reached. That moment seemed to last forever but then with a momentary burning sensation his fist slid inside me with my ring closing slowly around his wrist. I reared up in response but this time was able to keep the desire to growl almost within, just a little bit crept out between my gritted teeth.

“Excellent work!” was all Liam said in response before saying “Right then, I’m going to pull out now and then that’s today’s training session over with. I know I’ve said it several times already, but very well done Sam, I’m proud of you.”

“Thanks Liam, it would be great if we could call it a day, my arse is getting a little sore now!” I said quite sincerely.

Five minutes later after a bit of pulling and puffing (on my part) Liam’s fist vacated my rectum to my relief and I was provided with several wads of paper towelling to wipe myself clean of all the grease which had been smeared over my nether regions. As I did so Liam asked me to take some time out of the normal routine today and draw up a plan and schedule to select the six Volunteer Punishers out of the prison community ready for presentation to him in the morning. No pressure then! As I got dressed back into my prison uniform Liam reminded me that this is still highly confidential so no talking about it, he didn’t want the inmates to get wind of it before the prison is ready to roll it out. I agreed that I would keep it strictly to myself.

Back on the prison wing George asked me if I was okay as I seemed a little quiet, I grimaced and said that I had a stomach ache (which was true). He was genuinely concerned and said that I should take a break after the rounds had been completed this morning. I took him up on his offer as this would be an ideal way to somehow draw up a “beauty contest” come competition to select the six “lucky” volunteers. By the time I returned to work I had at least half an idea about what I was going to suggest, the rest of it I would think about tonight, which I did over a large pot of coffee and all distractions excluded i.e. no TV, the answer phone twitched on, my mobile switched off and the door bell disconnected. There was no way I was going to be disturbed!

TUESDAY 13TH APRIL 2010

It was a late night last; I was up until 1am putting the finishing touches to my presentation until it was polished to my satisfaction, so when the morning alarm went off I wasn’t really ready to get up and face the ordeal waiting for me at work. But like the trooper that I am I got up and was actually a little early for work, down to the traffic I’m afraid not my superhuman speed.

I will cut out the repetitive bits diary, after all you know that each day this week I will be going straight to the consultation room where I will be cleaned out and fisted by either Richard or Liam or both in order to ‘educate’ me. Actually this morning it was only by Richard and his sole mission was to get my anal ring totally used to being stretched wide by a fist, so for thirty minutes he methodically pistoned his fist in and out of my hole until it no longer caused me any discomfort and in fact I was actually beginning to enjoy it despite myself and the situation I was in. All too soon it was over and after withdrawing his fist for the last time Richard showed me techniques for closing my hole up again as if nothing had ever happened. I was impressed and my regard for Richard has increased immensely as a result.

Dressed once more I made my up to the Governor’s Office and knocked on the door, decidedly nervous and holding my presentation folder under one arm.

“Come in!” Liam called out.

As I opened the door and strode in trying to appear confident I was in for a shock, I was expecting to be making my presentation to Liam. Instead I was greeting by the smiling faces of Liam, Max, Adrian, Archie (the prison officer who had greeted me when I arrived for my interview) and George.

My face must have been a picture as I stopped in my tracks and stammered out a “Hello guys, I wasn’t expecting to see you all here this morning.”

After he had stopped chuckling Liam said “Sorry Sam, sorry about the lack of warning about your audience. I decided that you were nervous enough about doing the presentation without having the added pressure of knowing that you would have an audience too. You are no doubt wondering why the others are here.”

“Yes Sir, I am more than a little curious after all that you have told me.” I said quite frankly.

“As you know Max and Adrian are my deputies and business partners so are always included on major decisions like this volunteer business. Archie is here because he is an ex-union representative and his experience will be invaluable in ensuring that all we do is legal and above board i.e. make sure that the relevant rules and regulations are adhered to. Finally George is here as a witness and will be taking minutes for the meeting, he has also been part of your assessment to see if you kept your vow of silence. I am glad to learn that not one drop of information has George received from you and so you have passed that test with flying colours. Right then if everyone would like to make themselves comfortable Sam will start his presentation.”

Gulp here goes I thought!

“Okay, please bear with me for this is the first presentation I have done in a long while so I apologise if I appear a little nervous.” I said after clearing my throat a couple of times. I looked down at my notes to give myself breathing space and time to gather my thoughts before continuing.

“My assignment has been to establish a method to find six Volunteer Punishers, one for each prison wing. It will allow us to identify which inmates have the drive, desire, ability and the right attitude to carry out this important function. After a lot of consideration I realised that it will need to be a combination of management selection and peer selection, you know a bit like the TV show ‘X-Factor’ except the voting public will be fellow inmates. This is how I envisage it will run.

Week 1: We announce the competition and make it clear that it is open to all willing applicants with the auditions being held in the Chapel. The method of selection will be by answering questions, those that get the answer wrong will be eliminated; inmates who answer correctly go on to the next round of questions. By the end of the evening the number of applicants will be whittled down to twenty four applicants.

Week 2: This week each contestant will be given a task to complete which lasts all week. At the end of the week the inmates will vote on who carried out the tasks most successfully. Twelve inmates will be eliminated by the voting to leaving twelve remaining contestants.

Week 3: This week it steps up a gear. Each contestant now has to don the uniform of a Volunteer Punisher and start training in all aspects of the role. During the day they will learn the theoretical aspect of the role; then in the evening the contestants will receive training in the practical aspects in the Chapel’s punishment room. The whole session will be watched by the inmates in the auditorium area and at the end of the training session the inmates will vote off the least favourite or capable contestant. This will be repeated each day until there are seven contestants left.

Week 4: The final week sees the volunteers carrying out their duties for real, each day they will be moved to another wing so that all inmates can assess them in action before the final vote at the end of the week.

That gentleman is the outline of my selection process. Do you have any questions or concerns?” I asked.

“Thank you Sam” Liam spoke up “that was well presented and I like your idea very much. However I do have a question, you mention management selection but I can’t see where in the weekly elimination schedule our influence can be exerted.”

“That’s a good question Liam” I replied smiling. “My intention would be that ahead of the competition we will select a number of inmates who we consider suitable, meet with them in private and feed them the right answers so that they will make it through to the final twenty four. It is then down to them if they make it to the final.”

“I like it!” Max announced “A cunning way to get our favourites into the final, yet we will appear to be totally open in allowing the inmates to democratically choose their punishers.”

“Well said Max, I think we should run with this one” Adrian said thoughtfully “What does everyone else think?”

There was a unanimous decision to accept my proposal so it was signed off by Liam there and then. Next came the nitty gritty stuff, sitting round the meeting table we thrashed out the timetable, the design and wording of the competition, the questions to be asked at the audition round and what the tasks the contestants would need to complete. Last on the agenda were the inmates we would like to see included in the final twenty four contestants.

After much discussion and at times heated debate, the twelve inmates we agreed that should be included were Tyler, Flick, Eduardo, Dinesh, Jarek, Tony, Bert, Darren, Carl, Martin, Gus and Sayeed. The timing for the individual briefings would be within a couple of days of the posters going up. It would be done discretely so that no one, least of all the inmates would suspect that anything untoward was going on. The posters will be put up on Friday 16th April 2010 so that the inmates have the weekend to discuss and think about entering the competition. With that agreed the meeting was over and it was back to work for us, however with most of the morning gone it was a just short stint for me before my shift finished.

I got home and the first thing I did was to step into the shower with a cold can of beer, I wanted to wash the last traces of the grease from my body that tissues just simply couldn’t do along with the accumulated sweat from my pre-meeting nerves. With the beer warming my insides and the hot water pounding my body all my cares and thoughts about today’s events slipped away down the shower’s plug hole.

Towelling myself dry I turned my attention to this evening and the impending arrival of Jason and Aaron for our jog around the park. The two lads arrived a little later, dropping off their change of clothing and we made our way to the park. I decided to be kind to them tonight and started the jog off gently only starting to pick up the pace in the latter half of the lap. Just to add a little pressure to the exercise I engaged them in conversation while jogging, they quickly sussed my tactics but I wouldn’t allow them to let the conversation drop. At the end of the first lap I let them catch their breath while jogging on the spot before we carried on with the second lap, as it happened they led the way and I let them dictate the pace which I didn’t mind in the least. Who would? I had two pairs of pert buttocks straining beneath running shorts, muscular thighs and arms pistoning back and forth in unison. They were a sight for sore eyes indeed! By the end of second lap I came to the conclusion that their level of fitness had increased perceptibly. I kept this thought to myself as I didn’t want to boost their egos too much! To extend the exercise I insisted they jog back to my flat much to their moaning.

As they staggered up the steps to my front door I was chuckling inside, the sight of their sweat soaked clothes and bedraggled appearance was a far cry from their normal cock sure attitude that comes with guys in their prime. I unlocked the front door and held it open for them, as they passed by all I could smell was very sweaty bodies – Yuk with a capital Y!

“Right you two, no lounging around on my nice clean furniture with your sweaty, dirty clothes until you have showered and changed. I mean it. Run along while I sort out some refreshments.” I said before walking off and headed for the kitchen to raid the fridge for fruit juice and whatever I could find to eat.

A minute later I heard the shower running and the familiar sound of Aaron whistling floated in from the bathroom, it was such a trivial domestic sound that it caught me by surprise when I started to wonder what it would have been like if I had had children with my ex-wife. I was still thinking about it when I heard footsteps behind me and a “can I do anything to help?” brought me back to the here and now with a jolt.

Looking in the direction of the sound, the sight that greeted me made me lick my lips in reaction, I caught that action in mid motion and discreetly pulled my tongue back in. There stood Jason as cocky as ever, smirking, stark bullock naked, framed by the doorway using the lint to hold onto. I took a moment to take in his physique, his hairy muscular legs and finally his cock which was standing at half mast and bobbing to erection under my gaze.

“Jason, what on earth are you doing?” I asked in mock exasperation.

“I’m only doing what you told me to do.” He replied, walking into the kitchen and standing rather close to me. “After all you did say that you didn’t want us touching your nice clean furniture with our dirty clothes. I thought I’d prevent that from happening by making sure they were out of harm’s way from the start. Did I do wrong then?”

“Noooo, I suppose not” I replied.

“And you did say that you run a relaxed joint here, did you not?” he continued.

“Yes, this is true. Okay okay, now that you’re here why don’t you help yourself to a drink while we wait for Aaron” I suggested trying to keep my voice on an even keel and resist running my hands over his pert buttocks.

Thankfully Aaron joined us within a couple of minutes with his towel firmly wrapped round his waist, he did a double take at Jason’s nudity before shaking his head and wryly commenting “have you no shame boy?”

Laughing Jason said “None at all, now that you’ve finished hogging the shower I can perhaps use it myself!”

As Jason disappeared into the bathroom Aaron turned to me and asked “Doesn’t his antics bother you at all?”

“No, not really” I replied “If anything, he makes me laugh and he reminds me of myself when I was his age. Why? Does it bother you?”

Aaron was thoughtful for a moment then said “Yes, I guess it does. He is so brazen in the way he flaunts his body, okay he’s not bad looking but why does he have to do it so much?”

“Well, if you got it flaunt it I guess is the rule that he’s working by. To be honest you both have great bodies and are decent looking so I am a little surprised that you are not more like Jason.” I said sitting down at the kitchen table with a glass of orange juice in one hand.

“I’ve got Dad to thank for that, he’s instilled in me a conservative view of exposing my body and it’s very hard to overcome.”

“I find that if you want to overcome a mental block then the best way to do this is to face it and do the very thing you find hard to do.” I said in the most fatherly tone possible.

“So in my situation if I want to be more like Jason what should I do?” Aaron asked seemingly puzzled by my latest statement.

“Simple” I replied “remove your towel and let it drop to the floor. Remain naked until Jason returns and it’s time for you to go on your way. I will ignore your nakedness like I did with Jason, I am sure that you will find that before long you will feel more relaxed. The more you practise being naked, the more comfortable you will become with your body.”

“Are you serious? What just drop my towel? Okay, if you say so, but don’t tell dad will you. I don’t want him to think I’m queer or anything.” Aaron said with just a touch of edginess to his voice.

“Yes, yes and of course I won’t. You don’t have to do anything you don’t want to but I just thought it would help. After all at your stag do you stripped off in public happily enough.” I said shrugging my shoulders and took a sip of my juice.

“That was different, I was drunk and I got swept up in the moment. Right now I’m stone cold sober but I hear what you’re saying. I guess, we’re in private and no one’s going to see or say anything, so here goes.”

Taking a deep breath Aaron unfastened his towel and let it drop to the kitchen floor but kept his crown jewels covered with his hands. Standing there a little self-consciously he looked at me for approval.

“That’s all very well but my towel is getting dirty on the floor so please pick it up, fold it neatly and put it on the side over there please, then why not come and sit down at the table and have a juice with me. That way you will still be naked, getting accustomed to being so but not feeling like you’re on display all the time.” I said, deciding that I would not let him get off the hook so easily.

Sighing, Aaron did as he was instructed, picking up the towel and folding it necessitated him uncovering himself and as he walked back to the table I got a good view of him and his tackle. Although his hair was a blonde (dark straw if we’re being accurate) his body hair and pubes were several shades darker, made all the more striking by his naturally fair skin. Whereas Jason was a very big boy (10 inches by my reckoning at the stag do), Aaron was more your average guy which I wonder is perhaps part of his modesty problem. He made a good attempt of appearing relaxed but it was clear that he was relieved to be sitting down covering his modesty.

I let him be and we made small talk, I was good as my word and made no reference to his nakedness. Jason sauntered into the room, still naked and flushed red all over from the hot shower. He looked a little startled at the sight of Aaron sitting at the table without a stitch of clothing on and started to smirk.

“Less of that young man, it’s all very well for you to flash your tackle around without a care in the world but not everyone is as confident as you. Aaron is trying to overcome his shyness and you laughing at him isn’t going to help. We’re taking it one step at a time and the first goal is to get him accustomed to being naked.” I admonished him and then smiled encouragingly at Aaron.

“Thanks Sam, I appreciate your support. Jason, as my best mate, I would also appreciate your support, this is not easy for me as you well know.” Aaron piped up.

Putting his hands up in the air in mock surrender Jason said “Okay guys, I get the message and I am sorry for not being more supportive. A thought has just occurred to me, this is a safe place for us to be naked without judgement as we’ve already discussed previously. Why don’t we make it a rule that whenever we come over clothes are not permitted and we all have to be naked, that way Aaron will get all the practice he needs and won’t feel the odd one out. What do you reckon?”

“Sounds like a good idea to me” I nodded in agreement. “What about you Aaron?”

“Yeah, sounds cool to me, it will make things easier for me.... I guess. But no word of this is to leak out right?”

Both Jason and I nodded in agreement before I said “Well that’s sorted then, perhaps I can go for my shower now then.”

“Aren’t you forgetting something Sam?” Jason asked; then added in response to my quizzical expression, “You are still wearing your running gear, if this is a clothes free zone; they need to come off NOW!”

Chuckling at his impudence I nodded in agreement, stood up from the table and proceeded to remove my trainers placing them under the table where I normally keep them. Then I peeled off my muscle vest, pushed down my running shorts, leaving just my jock strap to go. Then in one smooth movement I pushed them down too, stepping out of them I put all my dirty washing into the washing machine before turning round with a smile on my face and arms spread wide and saying

“Are you happy now? I think this is enough for one day, I could do with a shower and you guys have got women to get home to, so get dressed and vamoosh. I will see you on Thursday.”

A little while later I had my flat back to myself and enjoying my second shower of the day. As the soap suds rinsed away I slowly stroked my cock thinking about Jason’s hot body and all the ways I would like to ravish his body given half the chance. Just as my imagination had me on my knees, with my hands wrapped round his waist and my face buried between his cheeks licking his tight little heiny hole, my balls decided it was time to unleash their load sending several jets of creamy spunk arching across the shower to hit the glass shower door and slowly slide their way down.

Recovering from my intense orgasm I looked down at the slug trails with disgust and quickly showered the congealing cum down the drain. And that diary brings the end to a very tiring day indeed.

WEDNESDAY 14TH APRIL 2010

Compared to yesterday, today was average really. Well average that is if you call having your boss stick his fist and half his forearm up your arse! No word of a lie, I kid you not, by 10am this morning I had been cleaned out and prepped by Richard. Okay Richard had been loosening up my hole ready for Liam who then using his experience pushed his fist further up my rectum than I thought humanly possible. Apparently he had found breaking the resistance of my inner rectal ring a challenge, but one that he was up for, and eventually succeeded in doing. Unable to stifle the groan I growled like a grizzly bear, face flushed red and sweat pouring down my face my inner ring opened up and his fist slid on by up into my bowels. Only the width of his muscular forearm prevented him from going in all the way to his elbow. I looked down between my legs (I was laying on my back with my arms wrapped round my knees) with an expression mixed with awe and horror at the sight of his arm half buried inside me, while Liam had a look of pure angelic rapture.

“Sam, you are a star do you know that? I have never worked with a guy who is so willing to explore his boundaries and push far beyond them. I have seen you in action as a fisting top, now I have seen you in action as a fisting bottom and I am very impressed indeed, you are so versatile. There is absolutely no way that I will consider any one else for the role of Volunteer Co-ordinator.” Liam said with a great deal of pride in his voice.

“Thank you Sir, I guess I have the army to thank for being able to push personal boundaries but I’m really not sure what the benefit of having your forearm buried in my butt will be in my role as Volunteer Co-ordinator.” I asked as politely as I could.

“It’s not so much the actual act you understand, although it must be said you have a very fine arse, but it is more of a test of your willingness to put your trust in me. Your level of trust is commendable, I couldn’t ask for more” Liam responded and at the same time started to slowly withdraw his arm and fist.

As my inner ring was breached by his hand I arched my back in response, groaning as I did so. Some part of me must have enjoyed it as my previously flaccid cock slowly engorged with blood until as his fist finally slipped out of my anus my cock was fully erect and bursting to erupt. My ring must have been slow to close because I could feel cool air flowing into my rectum before being expelled as my rectum closed up along with my ring. I lay there relaxing with my eyes closed for a moment, I was about to get up when I felt something warm and wet enclose my cock’s head.

Startled I looked up to see Liam’s head slowly descending on my cock until he had swallowed the whole of my shaft in one smooth move, then slowly and lovingly his head started to bob up and down. Jeez it felt good! I let my head slink slowly back on to the couch, closed my eyes and gave myself up to the sensations of the gorgeous blow job I was being given. Finally with my hips bucking wildly I could hold back no longer and I gave into the impending orgasm. Load after load of jism shot out of me and straight down Liam’s throat, not one drop did he let slip out and he didn’t stop sucking until my cock had run dry and receded to its flaccid state once more. I looked up at Liam in askance.

“Sam, it’s the least I can do considering how you have accepted without question all that I have asked you to do. I wanted to show you that as far as I am concerned this is a two way street and I have an inkling that it was an acceptable payback for you.” Liam said with just a trace of a smile on his face.

“Yes Sir, it was an unexpected bonus that’s for sure!”

“Right then, before we get back to normal duties is there anything you want to talk to me about?” Liam asked quite casually.

“Actually, there was as it happens. I know we agreed that we would speak to our preferred candidates once the posters have gone up but I’m concerned about timescales and I just can’t see us getting through all the candidates in time without suspicions being aroused. I am hoping that you will allow me to start talking to them today” I said as I cleaned myself up and started to put my uniform back on.

“Sam, you’re in charge of this venture now, if you think that’s the right thing to do, then go for it. All I ask is that you keep me posted on events or if you encounter any problems. Okay?”

With that the training session was over and I headed over to the prison wings and pay the first candidate a visit, namely Flick on A-Wing. Since the 48 hour removal of personal possessions punishment Flick had been true to his word, he had behaved himself and not got into any more trouble, thereby keeping his possessions and clothing in the process. However he had lost none of his cockiness and as I walked into his cell closing the door behind me it was very much on show in his mannerism and posture.

After he bantered with me about why I was paying him an unannounced visit I got straight down to business and explained about the purpose of my visit. I outlined the role of the volunteer punisher, broadly what would be involved and that we actively wanted him on board. Once Flick made it clear he was interested I gave him a run down on the questions that would be asked so that he would have the correct answers to get through the qualifying round. As he never asked about the uniform I kept quiet on it remembering his reaction to being stripped naked for his punishment. I decided that he could cross that bridge when he got to it. My final comment was for him to keep his mouth shut about our little meeting and to remember to register his application when the posters were put up on Friday. Flick’s mind was racing with the possibilities as I walked out of his cell.

On to B-Wing where I met just the person I was looking for playing snooker with a fellow inmate, who was just about to pot a red ball. Taking the opportunity while Tyler was waiting to play his turn, I walked up to him and whispered in his ear.

“Tyler, I know you’re playing snooker but I need to have a private chat with you right now in your cell, alone. It will be only for a few minutes and then you can continue with your game.”

Tyler frowned for a second, glanced at me but seeing that I was being serious nodded once in agreement and told his play mate that he would be back in a minute to continue the game. As Tyler was a force to be reckoned with there was no argument from the other guy.

As I followed him up the metal staircase to his cell I could not help but admire his muscular frame and jet black skin which had the optical effect of making him look like a moving obsidian statue. On entering his cell I closed the door behind me, turning round I was faced with the vision of Tyler sprawled out on his bed, hands behind his head, legs spread and his python of a dick snaking across one thigh. His balls hung loosely down between his legs. Despite my best intentions I could not help but look at them remembering the day that I had managed to accommodate the whole of his mammoth cock down my throat. Tyler chuckled loudly before inviting me to do the same thing again for him.

“Thanks for the offer” I replied “and as flattering as the invitation may be, I am here on official business not for personal pleasure. How have you been getting on since you voluntarily surrendered your clothing?”

“Oh man, I’ve been having a ball!” Tyler laughed again. “At first I was quite self-conscious, I know that might sound strange coming from me but it’s true I really was. It’s one thing when you are stripped as a punishment, you have no choice in the matter, but after the post-punishment meeting I voluntarily gave my clothing away in the hopes of becoming a volunteer punisher. I had to come up with a plausible story as to why you’ve kept my clothing and I’m not kicking up over it as the other inmates expected me to do. After a few days it was old news and the guys stopped asking me questions and simply accepted that I was going to remain naked from now on. It was made easier after Jarek’s antics because suddenly I was no longer the only inmate to be permanently naked. Now no one takes any notice except those that are either gay or trying to usurp my position as top dog on this wing.”

“Go on” I urged “I feel a story waiting in the wings just waiting to be told!”

“Do you remember how I told you when you first raided my cell that I had trouble getting any form of relief in this place?” he asked.

“Uh huh, I sure do”

“Well that isn’t a problem anymore. There’s a young lad on this wing, I’m sure you know him because he’s received the 48 hour no clothing punishment too, by the name of Gus. He’s very self-confident and easy going.” Tyler said.

“I think I know the guy, he looks very similar to Jarek but his hair is paler.” I asked pretending to be uncertain.

“That’s the guy!” Tyler agreed nodding with a smile before continuing “It must have been the day he got stripped as punishment I first really got acquainted with him properly so to speak. I was sitting in the canteen during our lunch break, chatting as normal to a couple of old timers when Gus walks over with his lunch on a tray and sits at our table opposite me. I don’t take much notice because up till now we’ve moved in different circles, however mid-way through his lunch he makes out that he’s dropped his fork and crawls underneath to retrieve it, or so I think.”

“What happens next?” I ask, genuinely curious.

“The next thing I know is a pair of hands pushing my knees apart and a pair of warm wet lips kissing my knob end. I don’t know who was shocked the most; me, my knob or the guy I was talking to! I looked under the table in surprise while my cock rapidly stood to attention under Gus’s expert administrations. No word of a lie he had swallowed the whole of my cock down to my balls within thirty seconds, and oh boy the feeling was out of this world! His head was bobbing, my body was sawing and I couldn’t help by groan with pleasure. All too soon I could hold off no longer and with a shudder my balls exploded jism down his willing throat. He only came up for air when my cock ran dry and was back to its normal size, then he resumed his position at the table without looking at me, with fork in hand and continued eating his meal cool as a cucumber.”

“Now that’s what I call a lunchtime treat!” I laughed.

“From that day on any time that I’ve wanted to dump a load I’ve only had to nod in his direction and I get to plunge my cock either down his throat or up his arse. Tell you what though, he’s a dirty bugger, he’s even got me to shove my fist up his arse right in up to my elbow! My eyes nearly popped out of their sockets he got me to do it. I didn’t think it was humanly possible, but he’s shown me otherwise on several occasions since then. So I’ve got myself a regular little bitch now and I couldn’t be happier. Well that’s not strictly true, I wonder when I’m going to hear about this volunteering business otherwise I’m going to think someone’s having a laugh at my expense and I won’t be very happy if that’s the case” he said throwing me a menacing frown.

“Actually that’s what I came to talk to you about....” I said and then spent the next twenty minutes going through the details of the selection process, the auditions, questions, tasks etc. I got him to repeat the questions and answers so that there would be no mistakes made preventing him from being a finalist. I left him lying on his bed looking like the cat that got the cream.

My final visit of the morning was to C-Wing where I bumped into Eduardo enjoying a cigarette by the main door. This made things easier for me because I invited him to join me for a short stroll round the exercise yard where I made small talk before doing the whole sales pitch on the volunteering, after only a minute or two’s thought he decided he was definitely up for the challenge so I gave him all the other necessary information before leaving him to finish his second cigarette while I went off for lunch.

After lunch I headed off to D-Wing in search of Dinesh, where I found him in the general lounge area reading “The Times” newspaper under the finance section.

Laughing I said “Planning your next big scam Dinesh? You do realise that you’re going to be inside for several years yet don’t you?”

“Oh yes Sir, but I can always dream and a man has to have plans for when he is released you know.” He said looking up at me and smiling.

“Indeed, you’re right. Do you have five minutes to spare, I have a proposition for you which you might find interesting.”

“Well, I’m not going anywhere as you’ve pointed out and this paper can wait, so fire away you have my attention” Dinesh said with a deadpan face.

I was getting polished in my presentation and in no time at all I had another volunteer in the bag and so it was off onto my next target, Jarek in E-Wing.

Jarek was also eager to be a volunteer, the only question he really had on the subject was the matter of a uniform. He had been hoping that he would get some form of clothing back but as previously explained to him; that simply wasn’t going to happen. The closest thing he will get to clothing is either the boiler suit for visiting times or the red beret and leather belt. Other than that he was up for the competition and hopefully become the one doing the giving rather than receiving for a change.

My final target for the day was Tony from F-Wing, I found him in his cell busy writing a letter which he quickly turned over on my entrance to the room. As I shut the door behind me he began to look concerned and asked

“Is there anything wrong Sir? I don’t recall being warned about an impending visit from management.”

“There isn’t and there wasn’t, but relax, I’ve come about a matter which might be of interest to you.” I said in my best conspiratorial tone.

“I’m all ears Sir, carry on then”.

Tony is a very astute guy, he grasped all the things I said instantly including the things I hadn’t said, such as the uniform. When I explained it to him he asked if he could wear the beret and belt as well as the usual jeans and T-shirt. I explained it was all or nothing and that he would have to forgo the pleasure of wearing clothes if he wanted the prestige of being a volunteer punisher. After much umming and aahing he finally decided that he would give it a shot, he had nothing to lose (other than his clothes) and it might be a laugh.

Once that visit was over I rejoined George to do the final round of the day before making my way home feeling mentally exhausted. I was pleased to get home and veg out for the evening without having to do anything or say anything to anyone.

THURSDAY 15TH APRIL 2010

No rest for the wicked as they say, back to work early the next morning and straight into Richard’s consultation room to be cleaned out and stretched to within an inch of my life. Today instead of depth Richard and Liam were going for width, by the end of the session they managed to squeeze two hands into my butt at the same time. Now this was going some and was not at all enjoyable for me compared to the other exercises. I was distinctly sore by the end of the marathon session and my anus took quite some time to close up again. But at least I would be able to take on the biggest hands, such as Tyler’s, should the need arise Liam and Richard assured me. Thanks, I think! All morning my bum throbbed, only easing off as it got to lunch time.

In an attempt to take my mind of the aching I threw myself into speaking to the other six candidates left on my list to talk to. Deciding to get the hardest sell over with first I made my way to A-Wing looking for Sayeed, I really wasn’t looking forward to this one because he’s a tricky devil and with him you really have to read the small print, as I have found out to my cost!

As the prison rounds had just been completed and breakfast a distant memory, most inmates were in their cells getting prepared for their daily jobs, whatever they may be. Sayeed was no exception, as I walked into his cell he was donning his outdoor overalls ready for his shift on the prison farm. He looked mildly irritated to see me but I chose to ignore it. I shut the cell door behind me and asked him to sit down.

“Is this absolutely necessary Sir? I’m going to be late for my shift and don’t want to get into trouble with the farm manager because of an unexpected interruption to my schedule.” Sayeed had definitely got out of his bed on the wrong side this morning.

“There is no need to take that tone with me Sayeed, what I want to talk to you about won’t take long and it is in your best interest to think about seriously. If the farm manager asks where you’ve been you can say that I called you into a meeting on behalf of the Prison Governor; that should keep him off your back. Now shall we start again with a little less attitude?” I asked in a very reasonable tone.

“Ok fair enough, sorry Sir, what was it you wanted to speak to me about?” Sayeed asked in a more conciliatory tone.

I outlined the volunteer punisher’s role, placing more emphasis on the mentoring and fatherly roles than the sexual activities as I knew it would appeal to his sense of morality and social consciousness. I deliberately left out any mention of a uniform, at this stage he knew nothing about it and it would only scare him off. He sat there silently deep in thought, occasionally throwing a guarded look before finally speaking.

“I will certainly give this idea a lot of thought but I have some questions which I would like answers to before I make up my mind either way. Firstly why have you asked me, what is in it for you? Secondly, why must I keep it secret? Thirdly, giving me the answers ahead of the audition is cheating; doesn’t it make the competition unfair?”


“Good questions” I replied “clearly there’s no pulling the wool over your eyes! Firstly, we, the management selected you for your social standing with the wing. We want someone that the other inmates can look up to. Secondly, you must keep it a secret because the posters don’t go up until tomorrow and we don’t want news to leak out ahead of time. Thirdly, yes technically you could call it cheating but it won’t make the competition unfair. The only advantage you will have is in the first round auditions where it is questions and answers. It will be whittled down to twenty four contestants, including yourself, after that if you become a volunteer punisher then it will be down to your hard work and merit. It’s entirely up to you, personally I think you will make a great volunteer but it is your decision.”

Sayeed was silent again for a couple minutes before finally agreeing with my reasoning and confirmed that he would be willing to participate in the competition and would abide by our rules. Thanking him for his time I left without delay to allow him to get to the farm without being too late.

Next port of call was B-Wing and a far easier customer, Gus, the guy who was now Tyler’s fuck buddy amongst other things. He was a push over, I appealed to the tart in him making sure I highlighted all the sexual perks that came with the role, I didn’t even have to mention the uniform for him to be sold on the idea. The only difficulty I had was to get him to understand that he had to keep our meeting secret from everyone, especially Tyler of all people!

After leaving Gus I made my way over to C-Wing and met up with Bert, an old timer in his fifties with just three years to go before his release. Despite his years he kept himself fit and was considered by management as being a very stable character generally popular with the inmates on the wing. Personally I get on well with him as we have a similar sense of humour and outlook on life. I was straight with him about the volunteer role, the pros and cons and why I was asking him to consider the position. Like Sayeed he considered it for several minutes before giving a “tentative maybe” then changing his mind to a “yes, okay”.

From Bert it was on to Darren, Carl and Martin on D, E and F-Wings respectively. Although all three men were physically very different; temperament-wise they were generally level headed, laid back with good sense of humours but didn’t take fools gladly and wouldn’t take shit from anyone. In fact perfect candidates for the roles! With a little bit of sales patter I had them all in the bag and my mission was complete. Twelve candidates of the management’s choosing which will give us a fifty fifty chance of getting the right guys into the volunteer roles.

I was behind time when I got home, I had barely half an hour before Jason and Aaron were due to arrive so it was a dash into the bathroom, quick strip wash and change into my running gear before they rang on the door bell raring to go. If I’m honest my mind was elsewhere throughout the two lap jog round the park and before I knew it I had two guys beefing at me that I hadn’t let up in the pace or giving them a half way breather like I normally did. I was a little unsympathetic in my response pointing out that they were here to get fit and lose some weight, no pain no gain! It did however bring my attention back to the task at hand and I was more focused from there on.

As I walked up to my front door and put the key in the lock Jason reminded us of our agreement made on Tuesday evening about clothing being banned within my flat. We all nodded that we remembered and promptly stripped off our running clothes once the front door was safely shut. As I wore the least clothing I was the first one naked, I picked up my sweaty clothing and put them into the washing machine. On my return Jason had by then stripped naked and was busy trying to cajole Aaron into removing his final piece of clothing, his pants.

“I hear what you’re saying Jason and yes I know I agreed to do it but I just don’t feel comfortable stripping completely when I am all hot and sweaty.” Aaron said with a slight whine to his voice.

Taking control of the situation I said “That’s fine Aaron, keep your pants on until you have your shower, then once you’ve had your shower come back to us with your towel on. Then if you feel comfortable you can take it off or leave it on whichever is good for you. At the end of the day you need to take it at a pace that is right for you.”

“I would prefer to do that if you don’t mind, I won’t feel so pressurised so may be more relaxed about it.” Aaron said smiling in my direction before walking towards the bathroom, as he passed Jason he stuck his tongue out in an exaggerated manner.

Both Jason and I laughed in response, shook our heads and made our way into the kitchen where we waited in our customary fashion making small talk until Aaron returned with towel wrapped firmly around his waist. I went next for a shower, during which I hatched a plan to give Aaron a goal to aim for regarding his acceptance of his naked body. So while Jason had his shower I discussed my idea with Aaron about building his self-confidence, to my surprise he was actually receptive to it. To cut a long story short we agreed that in the summer we will as a group (Tom, Mike, Jason, Aaron, Chrissie, Sally, Kirsty and myself) take a trip down to Brighton and do some sun bathing on the beach, more specifically the nudist beach! Something to look forward to, not sure how we’re going to broach the subject with the others though.......

FRIDAY 16TH APRIL 2010

D-Day for me at work, the day my project starts for real. Thankfully I no longer had to attend Liam’s training sessions so my arse got a rest at last! This morning the posters went up all round the prison advertising the auditions that were going to be held on Monday 19th April in the Chapel and I think it’s fair to say that there was a great deal of interest judging by the reaction of the inmates and the conversations that could be heard all over the wings. Some guys were serious others were in it for a laugh, but none had a clue about what really lay ahead. Apart from twelve inmates who had at least some idea about it. During the morning and afternoon prison rounds I was fielding questions left, right and centre. In the end George gave up on me leaving me to answer the questions while he carried on doing the cell inspections.

It was exciting thinking that my project was about to be launched but I was more than a little nervous because I need to pull it off big time otherwise my reputation will be in tatters. Not that my colleagues have any doubt about my abilities or ambition, so I can at least take comfort from that.

By knocking off time I was glad for the peace and quiet of my car whilst driving home and then my beloved flat, which has always been a sanctuary for me when the world comes crowding in like it did today. Not that I’m going to be in for long as tonight I’m out with the lads for that final food and drink binge before Mike and Tom do some serious dieting and exercising care of yours truly.

So diary, that’s all from me for one day as I have to get ready, put some smart clothes on spruce myself up before meeting the others in town. I don’t think I will be in the mood for writing when I get home later.

SUNDAY 18TH APRIL 2010

Oh my God! Oh my God! I can’t believe how this weekend has panned out.... if someone had told me what was going to happen I would never have believed them, in fact I still have to pinch myself to believe it.

Friday night in town went pretty much as expected, lots of food and far too much beer and spirits were drunk but we did have a brilliant time. Everyone was in good spirits but by the end of the night Jason was by far the drunkest in the group, so much so that Aaron and Tom both said that Kirsty would go mental when she sees the state of him.

“No shee woooon’t, she lovesh me sho mush” Jason protested.

“Not in that state she won’t!” Tom chided

“Well what are we going to do with him until he can sober up?” Aaron asked, suddenly concerned about his best mate.

“I can shleep at Shams flat, he’sh got a shpare room” Jason announced and then proceeded to hic up loudly.

“Um, I guess he can do. I mean I do have a spare room so he could kip down in there. Once he’s slept the alcohol off he can go home and do some making up with Kirsty” I said appearing to think things over.

“That’s settled then” Tom agreed. “Thanks for taking the burden on, I really don’t think Chrissie would have appreciated me bringing a drunken Jason home. We had too much of that when they were younger!”

“No problem, glad to be of service.” I smiled all the while hoping that Jason wasn’t going to throw up everywhere.

Waving the other guys off I steered Jason through my front door and half pushed, half guided him into my spare bedroom/office and plonked him onto the bed. I removed his shoes and made sure that he was comfortable before closing the door behind me.

By now I had the munchies again, alcohol has that effect don’t you find? I made myself a coffee and was standing in front of the fridge peering inside trying to decide what I fancied eating when I nearly jumped out of my skin. A pair of hands had snaked their way round my waist and met in the middle, at the same time a lager laden mouth breathed on the back of my neck before planting a firm kiss on it. I stood there rigid before exclaiming

“Jason, what the hell do you think you’re doing?!” and pulled away at the same time, turning to face him.

“Something I’ve wanted to do for a very long time!” Jason replied in a husky voice, he didn’t seem to be drunk anymore.

Before I could react he stepped up to me, with one hand he pulled me towards him and with the other he held the back of my head so that I couldn’t pull away. I opened my mouth to speak and found it instantly covered by his hungry mouth. His tongue darted out and thrust its way past my lips (which had started to close in reaction) and proceeded to ravage my mouth mercilessly. I was so taken aback I did nothing to resist, it felt so strange having a masculine mouth kissing me, I have only been kissed in this way by women in the past. Desire inside me ignited and my hands left my side to explore the body pressing into me, I pulled him closer to me, I could feel his erection through his jeans pressing into my equally erect cock which was straining to be released. I started to kiss him back, pushing his tongue into retreat before thrusting my tongue into his mouth. I don’t know for how long we kissed but my lips and chin were starting to get stubble burn – a first for me. Our hands became more desperate in their exploration and if my cock got any harder I was going to explode!

Jason must have read my mind because without saying a word he stepped away from me, his eyes were full of lust and his chest was heaving. Then he took my hand and still not saying anything pulled me out of the kitchen and effectively dragged me into my own bedroom. Once inside he pushed me backwards onto the bed where I lay sprawled out wondering as to what would happen next. I didn’t have long to wait to find out because he dived onto the bed landing between my outspread legs and expertly undid my jeans before yanking them down around my knees along with my boxer shorts. Standing up for a moment he pulled them off me entirely before jumping onto the bed again and taking my throbbing cock in his hand.

Looking along my body and into my eyes he whispered “You don’t know how many times I have dreamed of being in this situation. I’m going to savour every minute of this”

Not knowing quite how to respond I smiled encouragingly and dropped my head back onto the bed. Delaying no further Jason started to lick the shaft of my cock as if it were a lollipop coating it liberally with saliva before moving onto my cock head. I raised myself up onto my elbows to watch him; his eyes were closed as he slowly and smoothly swallowed the whole of me right down to the base. I had to concentrate so hard on not cumming there and then, I thought of mundane things until I was under control before I could relax and enjoy the expert blow job I was receiving. The sight of his handsome face bobbing up and down, lips wrapped round my shaft was a sight to behold and I’m sorry to say that it wasn’t long before I couldn’t restrain myself any longer. My hips began to buck and my head dropped back down again on to the bed just as my cock exploded sending jet after jet of jism down his willing throat. I was panting heavily from the orgasm but he was totally unfazed as he carried on sucking my cock until it had gone soft, only then did he reluctantly let it drop from his mouth. I thought he had finished with me but no, not by a long chalk. Without missing a beat he started licking and mouthing my balls, at the same time his hands reached out for my legs, once he had hold of them he pushed them up and back towards me. Understanding what he wanted I wrapped my arms around my knees to hold them in place. His tongue then travelled down from my balls along my crack until its goal was reached, my hole. He licked and lapped at my ring, in and out it darted round and round until even I could feel it relaxing and welcoming the intrusion.

While he was occupied down below I managed to gather enough thoughts to think about lubrication and remembered that I still had some of the Crisco Liam had given me, in my bedside drawer. Reaching across the bed I managed to open the drawer and retrieve it without Jason losing a stroke.

“Jason mate, you might want to use some of this” I said offering him the opened tub.

“Sure thing Sam, I have just the thing for that” Jason replied with a chuckle and immediately took a glob of it and greased up his cock.

Then throwing me a wink he placed his cock at my entrance and slowly pushed. Bearing in mind my recent training at work he had no problem getting past my ring and his cock, despite being a whopping ten inches in length, quickly disappeared inside. When he was in as far as he could go he took hold of my knees, pushed them aside and leant forward intent on kissing me. I reached out and pulled him towards me at the same time wrapping my legs around his waist to keep him buried inside me. We kissed passionately for the longest of times, finally coming up for air he gave me one last kiss before he nuzzled and bit my neck and shoulders as he started to slowly fuck me. He might be young but he was certainly experienced and/or talented in the art of fucking! He had the knack of hitting my prostate with every stroke and boy did he have stamina. On and on he fucked me gradually gaining in pace and force, I was loving every single moment of it. My head was rolling on the pillow with groans escaping from my lips in time to his thrusts and my legs tried to pull him ever closer to me until his balls were at risk of being swallowed too!

As they say, all good things must come to an end and with a grunting cry Jason’s body went rigid, spasmed several times before he collapsed exhausted onto me panting heavily. I kissed him tenderly on the cheek and held him in my arms while he got his breath back. My legs released their grip and I stretched them out straight again which caused Jason’s now subsiding cock to slip out of me dribbling a little bit of after-cum across my thighs. We laid there motionless for several minutes without saying anything, however his body pressing into mine aroused my cock from its slumber and I decided it was my time to show this youngster that an old man can still have a few tricks up his sleeve.

So I reached across him to where the Crisco tub sat abandoned and took a generous handful before rolling a sleepy Jason on to his front and spreading his legs. He made protesting noises but I played deaf and started to smear the Crisco along his crack and pushed some inside his anus. Now I understood his concerns for his ring was tight and he knew the size of my cock. He must be an anal virgin; I smiled to myself and thought ‘I’m going to have one tight hole to fuck tonight!’ In view of this fact I took extra care and attention to warming up his hole. First I inserted one finger and stroked his prostate which persuaded him that this wasn’t such a bad idea after all. Then when he was relaxed with one finger I introduced a second finger and so on until I could get three in. By this time he was raring to go so I climbed on top of him, supporting myself with my elbows and slipped my cockhead just inside his ring. He reared up in reaction and his ring clamped down tight. I remained stationary until he released his grip and then gently applied pressure pushing my cock inside inch by inch. Finally I was fully inside, what a gorgeous feeling to be inside a tight hole, not only that the view before my eyes was hot too. Jason was lying with his head on his hands which accentuated the musculature of his back, further highlighted by the shadows cast by the hallway light. I was having difficulty remembering how I ever found a woman sexually attractive, but then again it’s like comparing day with night. Both are very different but each beautiful in its own way. Back to the task at hand and I quickly became consumed by the passion of the moment and was fucking Jason’s arse like there was no tomorrow. Again all too soon I climaxed and shot my load deep inside him before rolling him onto his side, lying spooned together with me still up him. I never lost my erection and five minutes later I was ready to go again, this time I took it more leisurely and as I slowly fucked him I reached over and stroked his cock until he had another erection. Somehow by coincidence or good luck we climaxed at the same time, my sheets definitely needed to be changed now! Finally our lust was spent for now and we drifted off into sleep.

It was early the next morning when I next woke up, the sun had just risen and was streaming in through the windows; I never had the sense last night to close the curtains. Jason was still asleep looking positively angelic, oh how deceptive that man can be I thought to myself. I guess this is the sight Kirsty must see most mornings, the thought of her brought up pangs of guilt and it took the edge of the post-sex glow I still had about me. Mentally I shrugged my shoulders, it takes two to tango and he was the one who had initiated the action, I certainly had no intention of spilling the beans to Kirsty or anyone else. Jason is a big boy (literally) and can choose his own path, who am I to judge?

Anyway, where was I? Oh yes lying in bed watching the man I had shagged the night before. Deciding I was hungry and definitely needed a shower as a certain present deposited the night before was about to make an exit, sooner rather than later. I crawled out of bed as quietly as possible so as not to disturb sleeping beauty and tiptoed to the bathroom. First port of call the toilet, then into the shower to wash off the smell of sex, and finally have a shave.


Twenty minutes later I was in the kitchen brewing a pot of coffee and grilling some bacon for a sandwich when I heard the shower running so I set the table for two and put some more bacon under the grill. By the time I was buttering the bread and pouring out the coffees Jason sauntered into the room, towel wrapped round his waist and hair all tousled.

“Did you sleep well?” I asked brightly.

“Yeah, like the dead thanks. Is that bacon I can smell? I’m starving!” Jason replied casually as he sat down at the table and poured himself a cup of coffee.

This whole situation was so surreal, in my kitchen sat a man young enough to be my son, who I had known virtually all of his life, and had a girlfriend of his own yet sat here as if this was the most natural thing in the world. It then occurred to me that this can’t have been the first time he had been in this type of situation. Sitting down opposite him I passed him his round of bacon sandwiches and as I ate mine I planned what I was going to say to him.

However Jason beat me to it by thanking me for breakfast and for taking care of him so well last night. Taking care of him had more than one meaning I smiled inwardly. He asked if I had any objections to him calling Kirsty to let her know that he was fine and would be home later. I shrugged my shoulders and said “Be my guest”. He stood up and wandered into the living room to retrieve his mobile before returning and sitting back down at the table once more. With his cup of coffee in one hand and his mobile in the other he quick dialled Kirsty and chatted away to her for about ten minutes. Oh boy was he a smooth operator, he had her eating out of his palm in no time and I’m not even convinced that he actually apologised for not going home last night. At the end of the conversation he swore that he loved her and would be home by lunchtime.

“You’ve done this before haven’t you?” I casually asked taking a sip of my coffee.

“Done what? Had sex with a man or been unfaithful to Kirsty?” he asked with raised eyebrows.

“Both. Does she know that you bat for both sides? Or that you have been unfaithful.”

“No one knows that I do on either counts and that’s how exactly how I want it to stay” he responded giving me a hard stare.

I held my hands up in mock surrender before bursting out laughing stating “I’m not judging you Jason it’s just that last night came as a bit of a surprise, a very pleasant one granted, but a surprise none the less but this morning you seem totally relaxed and gave a very polished performance which led me to suspect that you’ve done this before.”

“You caught me fair and square Guvner” Jason replied with a sly smile.

“So tell me what made you pull that stunt last night? You weren’t as drunk as you were making out were you? Why pick me, I’m old enough to be your father and there are plenty of young guys out there who’d be more than willing to take your cock whichever way you want it.” I said in all seriousness.

“Like I said last night, and I meant it, I have wanted to get you into bed for so long I have forgotten a time when I didn’t want to. Ever since I was about fourteen years old I have fancied you like crazy. I used to hang onto every bit of information I could get when you were in the army and I was so jealous of your wife thinking she was in bed with you each night. You have no idea how many times I have just wanted to touch your body or have you hold me in your arms. I can remember listening to the conversations Aaron had in school and if there was any suggestion that you would be going to his house I would find a way to gatecrash the barbecue or party.” Jason admitted quite candidly.

I was silent for a moment before responding. “I don’t know what to say, I never had a clue that you felt like that and if I had known I probably wouldn’t have been very receptive in those days. I was too busy being a man’s man at the time and no one was going to say that I was anything other than a real 100% heterosexual alpha male. It’s only since I have worked as a Prison Officer that I have even contemplated that there could be another side to me that hadn’t been explored. Thinking about it I do seem to remember you being on the scene a lot when you were a teenager, we simply put it down to you and Aaron being inseparable buddies.”

“Yeah” Jason replied, deep in thought remembering the past “we were and still are I guess. It has been very hard sometimes keeping these feelings hidden from view and a couple of times it has nearly slipped out but as far as I am aware no one suspects my bisexuality. I love Kirsty very much and I want to be with her, but there is this other side of me which needs to be satisfied at the same time. Up until now I have been having one night stands when I get the opportunity but I have grown tired of these casual and sporadic sessions which somehow no longer feel as satisfying as they once did. I guess if I was honest I would like to find a guy who loves to have sex with no strings attached.”

Again I thought for a moment before replying “So let me get this straight in my head, you are looking for a guy who is prepared to have sex with you on an ongoing basis but is happy to keep it secret and isn’t looking for a relationship with you? I guess it would help if you liked the guy too?”

“Got it in one! Any ideas on where I should look for this guy?” Jason asked raising one eyebrow.

“Well....... I suppose if you are having trouble finding someone I guess I could help you out in the meantime. I love sex, am not looking for a significant other; we get on okay and can keep my gob shut. What do you reckon? The other bonus is that you have an excuse for coming round here as I’m now your fitness trainer.” I said trying to sound matter of fact as if this was the most normal thing in the world.

“Great minds think alike! If you’re up for it I definitely am but I’ve just realised the time, if I’m not careful I’m going to be late and that is something Kirsty does NOT like.” Jason said closing the discussion on the subject by jumping up and heading for the bedroom to get dressed. Within ten minutes he was flying out of the door with a promise that we will have to this again real soon. Yeah yeah I thought, where have I heard that before?

The rest of Saturday was spent flitting between surfing the internet, watching the Sports Channel and reluctantly doing mundane chores round the flat.

Sunday was pretty mediocre if I’m honest, went to the leisure centre for the weekly swimming session with the guys which was very surreal as Jason acted perfectly in character as if Friday night had never happened. I don’t honestly know if I was relieved or disappointed, either way tomorrow (Monday) has been looming large in my mind.

MONDAY 19TH APRIL 2010

The atmosphere in the prison today has been electric; it only found a release in the evening when it was time for the auditions in the chapel. Standing on the podium with Liam, Max and Adrian at my side I looked out over a sea of expectant faces and began my speech welcoming each and every contender for the six positions of Volunteer Punishers. There must have been nearly six hundred men in the room as it was standing room only (all the chairs had been removed earlier in the day). Having explained the rules of the audition tonight I asked the men to hold their competition passes in the air for without a valid pass they will be excluded from the competition and escorted from the chapel immediately

“Right folks!” I called out loudly “let’s get the competition under way. Okay, listen up. For starters it’s a simple yes or no for the answer. Question one, do you think that by being a volunteer punisher this will give you authority over other inmates? You have five minutes to make your mind up.”

For a minute or two there was silence then slowly a whisper was heard and then more as inmates decided to discuss the whispering got louder and louder until I had to shout for silence in the room.

“Okay guys, times up. Put your hand up in the air with your pass clearly showing if you think the answer is yes.” I announced. Around two thirds of the room put their hands up.

“All the yes’s are to move to the left side of the room where Liam is standing and all the no’s are to the right where Max is standing. Please do so as quickly as possible so we can keep to the timetable.”

For a couple of moments there was a swirling mass of bodies as the inmates divided into two groups. George and a couple of other officers patrolled the divide to ensure that there were no sneaky jumpers after the results were announced. As the inmates quietened I announced the correct answer.

“The correct answer to this question is – YES – you will have authority over other inmates. You will follow directions from the prison staff and be given certain powers which will be confirmed later in the competition. All those that have answered incorrectly are now to leave the chapel by the main door and surrender your passes to Liam as you go.”

There were groans of disappointment from the ‘No’ group but they followed the instructions and slowly filed out of the room leaving four hundred inmates in the competition.

“Question number two.” I called out “Do you have the right to humiliate in public an inmate who has broken the prison rules? Again this is a yes or no question and as before all the yes’s to left and no’s to the right.”

This time the room was split fifty fifty, the correct answer was ‘no’, after the yes’s had left the room two hundred inmates remained and the questions continued.

“Question number three. If an inmate approaches you for advice or assistance regarding anything providing it’s legal are you obliged to help?”

Again the room was evenly split, the correct answer was ‘yes’, once the no’s had left the room one hundred inmates remained.

“Question number four. Once an inmate has broken the rules and the punishment initiated, do you have the right to engage in any sexual activity of your choosing and whenever you want? Same as before this is a yes or no question with all the yes’s to left and no’s to the right.”

The room was deadly silent, the inmates looked stunned and then a few started to grin wickedly at the thought of the question’s implications. This didn’t stop them from being indecisive and it took longer for the dividing up to finalise. In the end it was split with sixty saying yes and forty saying no. Yes was the correct answer so we were left with sixty inmates, the chapel was now feeling decidedly emptier.

“Question number five. If we told you that the uniform of a volunteer punisher consists solely of a red beret and leather belt with no other clothing being permitted, would you be prepared to comply with this requirement?”

This time the reaction from the inmates was more animated and I heard a few gasps, whistles of astonishment and a couple of “no ways!” but surprisingly at the end of the dividing there were thirty five yes’s and twenty five no’s. I had been expecting a lot fewer yes’s considering what had been asked, but I was relieved to see that the twelve inmates I had primed were still in the running.

“Right guys, we’re now down to thirty five and there are only twenty four can go through to the next round. This is going to be your first challenge. Scattered around the prison in the public areas are twenty four white envelopes, inside will be a red ticket with ‘VP’ embossed in silver. The twenty four men who successfully find the envelopes will be the ones going through. After I say go, you are free to search for them. On your marks, get set, go!” I cried out.

In one surge the thirty five men raced out of the room determined to be the ones to find the tickets. Once the chapel was empty Liam came over to me and congratulated on how well it had gone so far. I smiled an acknowledgement, inside praying that the rest of the competition would run just as smoothly. It took about five minutes for the first contender to come back in the room and about half an hour for the twenty fourth to stumble back into the chapel clearly exhausted having scoured the prison for the last remaining ticket. On his entry the chapel door was locked behind him, with a note outside advising the other eleven men that they were out of the competition.

“Okay guys; the first selection round is now over and this is where the hard work begins! Starting from tomorrow and continuing until Sunday you will be split up into six teams of four. Each day you will be on a different wing carrying out specified duties. Then on Sunday the rest of the prison inmates will vote for who they feel undertook the duties most willingly and most successfully. The twelve with the most votes will go through to the next round. Any questions so far? No? Okay, then I’ll explain a couple of rules. You are free to reject the tasks set you but by doing so it will immediately disqualify you from the competition, equally if you decide that this competition isn’t for you then you are free to leave at any time. That’s all for now, you are free to leave and return to your cells, get a good night’s sleep because the next six days are going to be hectic for you. In the morning you are to report to the main reception where your instructions will be published. Good night gentlemen.”

There as a small round of applause from the inmates and prison staff, to whom I bowed before we all left the chapel and went our separate ways.

Back at home, I flopped onto my sofa mentally exhausted from today’s events and took my time enjoying a cold beer letting my mind go blank. I was only roused from this state by the sound of my mobile phone bleeping to let me know a text message had arrived. Sod it! I thought to myself but couldn’t resist seeing who it was. It was Jason, just asking how my day had been – if only you knew – and shall we have another session after swimming on Sunday 25th April as Kirsty is off to visit her best friend in Manchester that day and will be staying overnight. I text back saying that sounded a great idea and to make sure he had a good night’s sleep because he was going to need it....

TUESDAY 20TH APRIL 2010

I was in even earlier at work than usual, I simply had to make sure that the instruction leaflets had been printed correctly, that I was in position and prepared for when the twenty four contestants arrived at the main reception. I was idly chatting to Andy, the security guard on reception when they started turning up en masse. It was like being hit by a tidal wave! They were full of enthusiasm and couldn’t wait to see what tasks they were to be set, I wasn’t sure if they would be so happy when they saw what was required though.

I spent the next ten minutes explaining that they will be given a number of tasks which everyone will have to participate in and complete to the best of their ability. The other inmates will be watching their every move and at the end of the six days will be voting for the contestant who has most impressed them. I then read out the daily tasks to them:

1. Assist with the cleaning & maintenance of the prison facilities.
2. Assist the prison officers during the daily cell inspections.
3. Befriend new arrivals, help them settle in & offer assistance where required.
4. Befriend inmates who are having difficulty socialising, help them network & offer assistance where required.

They were quiet for a few minutes while it sank in before Sayeed put his hand up and asked politely what the purpose of these tasks was.

“As ever Sayeed, you ask a very pertinent question” I said smiling broadly to him and the others in turn “and I am happy to answer it. Task one involves you doing chores which others normally refuse to do or do so unwillingly, thereby proving your ego and pride is not going to be a barrier to your progress. Task two requires you to distance yourself from fellow inmates sufficiently to help the prison officer search the cells, sometimes against the inmate’s wishes. Do you have the integrity to do this? Task three, this is a demonstration of your social skills and ability to relate to others who may be feeling vulnerable. Finally, task four. This will involve you dealing with inmates who will already be known to you, so you will have to overcome any personal prejudices you may have about that person as well as using the same skills as for task three. Any questions?”

No one answered so I split them up into the six teams making sure that any guys from the same wing were split into different groups. I then sent them on their way having explained in greater detail what they need to do but that a large part of it will be down to their own initiative and reminded them that their every move will be watched by the inmates. Then to add just a little bit of pressure I said that I would be round doing spot checks at random times of the day which brought a collective groan from them all.

I spent most of the day doing exactly that and catching up with the other officers making sure that the contestants were doing what they were supposed to be doing (which I was pleasantly surprised to find that they were doing, but it is only their first day).

This evening I actually enjoyed going for a run with Aaron and Jason, it was great to be doing something that didn’t require a great deal of thought (apart from making sure that I wasn’t going too fast for them). After our cooling down exercises and walking back home I commented on the fact that I could see improvements in their fitness levels and perhaps we ought to up the ante a little by doing two and a half circuits. Surprise, surprise this brought groans of protest from them but as their coach my word goes so as from Thursday we will be jogging further. I also dropped in the fact that I will be doing a physique check after the showers to ascertain if they have been doing all of the exercises I set for them.

After we had all had showers it was time for the physique inspection. As was now customary Jason and I were naked but Aaron was still hiding within his towel, not for long though. With Aaron watching while sitting on the sofa I got Jason to stand up straight in the middle of the lounge with his hands down by his sides looking forward. I then took my time examining him from head to toe making positive comments whenever I found an improvement in his muscle tones and reduction in his fat layers. I then focused on areas requiring attention. Giving Jason a sharp but playful slap on the bum I told him to make himself comfortable as it was now Aaron’s turn.

With a sigh of resignation Aaron stood up and assumed the same pose Jason had and I repeated the procedures that I had done with Jason. In all fairness both of them had made good progress and said so, this brought smiles and thanks from them. While Aaron was momentarily distracted by the compliments I until his towel and whipped it away before he could protest. I continued with my inspection pointing out that the towel had impeded my progress and simply had to go! Jason decided to go one better and retrieved the towel before putting it into the washing machine so Aaron had no choice but to join us in nakedness – he’s a little devil, that Jason! Aaron was rather petulant for a few minutes following this stunt but eventually got over it and by the time they dressed to leave he was relaxed enough to take his hands away from his crutch and behave more normally.

WEDNESDAY 21ST APRIL 2010

Work has been a little surreal today, the contestants have moved on to another wing as instructed getting on with their tasks with little supervision, so there has been little training for me to do. The feedback I have been getting has so far been positive, although it is too early to say if it will have lasting effects on the prison system. I could almost believe that it was business as usual except that we had some volunteers in helping us out.

THURSDAY 22ND APRIL 2010

Dear diary, nothing much to say. Today was much the same as yesterday, the only difference is that Liam called me in to his office for me to give feedback which I did in as balanced a way as possible. Even running tonight with Aaron and Jason was par for the course. Aaron summonsed up the courage to drop his towel part way into the evening which I acknowledged with a smile and nod. Jason thoughtfully made no issue of the matter.

SUNDAY 25TH APRIL 2010

Sorry for not having written for the last couple of days, with nothing going on there doesn’t seem much point in writing anything. Today has been different, in fact a first for me, I have been to a Sauna for the first time! Me at forty five, going to a gay sauna of all places..... but I am getting ahead of myself (as usual).

As I read the Sunday paper over breakfast a text came through on my mobile, it was Jason, cancelling our session no doubt I humphed to myself. But I was wrong, the message actually read:

“There’s been a change of plan. Kirsty wants me to wave her off from Euston Station so I can’t go swimming. Meet me outside Euston Station at 3.30pm and we can go into town. Please say you can make it. Jase xx”

Mmm I thought to myself, sounds interesting so I text him back agreeing to meet him as arranged. In the meantime I had a swimming session to attend. Due to time constraints I would have after the swimming session I took a change of clothing with me to the leisure centre. I paid to hire a locker overnight acting as casually as possible so as not to attract attention to my plans. Afterwards I quickly donned my clean change of clothing and made a discreet exit heading for the tube station. I was running five minutes late when I arrived at Euston to find that Jason was already waiting for me. I went to apologise for being late but from the expression on his face it was clear that he was simply relieved that I had turned up at all. I asked him what the plan of action was for this afternoon and evening. He refused to divulge any information saying it was all taken care of and that I should just relax and enjoy the experience. Fair enough so I let him have his way.

Our first port of call was Leicester Square, more specifically the cinema where we watched the recently released “Alice in Wonderland” which was very well made but a little on the weird side. I kept this last thought to myself as Jason clearly loved every moment of it (perhaps it’s an age thing). From there we walked over to China Town and enjoyed a sumptuous three course meal in an expensive looking restaurant, all paid for by Jason despite my protests to pay my half. Finally stuffed with food beyond comfort levels we sought refuge in a coffee house in Soho and watched the world go by chatting about anything that came to mind. Finally when I thought we were going to call it a day the final surprise was revealed, well, only as we walked up to the front door actually. In bright rainbow neon lettering were the words ‘Manzone Sauna” – there was no way you could mistake what this establishment was! I looked at Jason in surprise and asked him if this was where we were headed, indeed it was and without further delay we went inside.

Not knowing what to expect I looked around me studying every detail, at first glance it looked very much like a hotel main reception with a butch looking guy in his early sixties manning the desk. As Jason paid our entrance fees he gave me a curious glance up and down, stopping momentarily at crutch level before smiling briefly at me and handing us a couple of white towels and locker keys. He asked if we had been before and offered us a tour of the facilities, but Jason politely declined as he had been here several times already. He headed straight to the only door available and indicated that I should follow him, as we got to the door the receptionist pressed a button and a buzzer sounded releasing the lock on the door. On the other side of the door was a small changing room with lockers along one wall, on the opposite wall stood three doors, one with a sign saying ‘rest room’, one with ‘showers’ and the other ‘amenities’. Wasting no time we stripped off our clothes and wrapped the rather small white towels around our waists before locking our clothes away and walking through the amenities door and into the corridor beyond which had several doors on either side.

“So Sam what do you fancy trying first?” Jason asked with a smile “They’ve got a steam room which is hot and wet, a sauna which is hot and dry, a Jacuzzi, a massage parlour and exercise room.”

“Well I don’t fancy the exercise room” I replied “we get enough of that already, nor the massage parlour. I think I will try the sauna first.”

The heat hit me as I opened the door, it was like walking into a furnace and I could feel sweat bursting out of every pore as I stepped inside. The lighting was dim inside, provided by one solitary red light bulb, but it was enough to make out the two tiered slatted wooden benches running along each of the walls. There were already five men in the sauna, ranging in age from late teens up to early seventies and all were wearing the obligatory white towels. In one corner stood the heater with what looked like hot pumice stones, adjacent to it was a metal bucket of water and a ladle for putting water onto the stones. As I walked down the aisle between the benches I tried to make visual contact with the guys but most had their eyes closed or were staring down at the floor, avoiding eye contact. The only one who did look up was a young lad who appeared to be in his late teens who smiled shyly at me, if you ignored the spots he was cute in a goofy sort of way. I felt a tap on my shoulder and with a very pointed look on his face Jason indicated where we should sit. Strangely the seat I was offered was out of eye line of the youth, I mentally shrugged my shoulders, if Jason wanted to be jealous over a smile let him.

Jason and I chit chatted for a few minutes but it was just too hot to talk so the conversation died out and we sat in silence soaking in the heat and feeling the sweat trickle down our bodies. After what seemed an eternity Jason admitted defeat and we escaped into the relatively chilly corridor to cool down. I decided that I needed to wash off the grime and sweat from my body before I did anything else so I headed back to the changing room and straight through the door marked ‘showers’. It was just as I expected, a communal shower area much like the leisure centre except for the fact that here they provided soap and shampoo! Hanging my towel up on a convenient clothes hook I stepped over to the nearest shower head and turned the tap on. Eeeek! The water was cold but quickly warmed up and I lathered myself up, as I did so I heard the shower head next to me start to run, glancing over I saw Jason doing the same thing. Boy was he a sight to behold and the sight of him washing was somehow erotic, so I asked him if there was anywhere more private that we could go and you know.....

“Easy tiger!” Jason laughed “There’s plenty of time for that later, just chill out, we’ve still got the steam room and Jacuzzi to go yet. It’s my turn to choose, so I think the Jacuzzi is next followed by the steam room. Come on old man.”

With that he turned off the shower, picked up his towel slinging it over his shoulder, not bothering to dry himself and opened the door to the changing room. Only then did he look to see if I was following, which I was just a couple of steps behind. The Jacuzzi room was actually quite busy with about four other guys already sitting in the bubbling water and another couple standing around talking while idly watching the others. Luckily there was enough room for us to squeeze in although it was a bit cosy (okay, sardines might be a better description!) I sat down gingerly not wanting to slip and make a fool of myself and I noticed that Jason did much the same. He quickly settled back and closed his eyes enjoying the sensations the bubbles were causing. I however was more curious about the fellow occupants of the Jacuzzi and casually looked round the pool. Just regular guys really I thought to myself, as I did so I felt a hand slide it’s way slowly up my thigh to my groin and then over to my crotch. Startled by this development I glanced over the owner of the hand, who looked at me with a tentative smile and pleading expression. I would have put him in his early sixties, not bad looking for a man of his age and then seeing that I wasn’t about to punch him his smile broadened before he looked down and concentrated on exploring my body. I spread my legs a little to allow him easier access, his fingers by now had hold of my balls and were gently rolling them, my cock was rapidly rising to attention and the head was just poking up above the frothing water. I expected the hand to stroke my cock but instead the hand went lower and I felt a finger trace the outline of my anus before very gently pushing the tip just inside my hole drawing a satisfied sigh from my lips.

“Do you like that? I can give you something better if you would like” the owner of the finger whispered trying to be discreet as possible.

“Yeah I guess I might. How do you fancy a little company? I’m with this gorgeous guy so we come as a pair.” I replied, sounding out his sincerity.

By now Jason had focused in on the conversation and seeing the state of my cock put two and two together instantly. Raising one eye brow he looked at me with a grin and said “you don’t waste time do you?”

“Nope” was all I said in response before turning back to the guy and asking “Well?”

The guy must have thought he’d died and gone to heaven because he had a big grin on his face and said he knew just the place to go. Five minutes later we were in one of the ‘rest rooms’; designed apparently just for this type of activity. There was a single bed sized couch covered in black plastic along with two armchairs covered in the same material. Beside the bed was a coffee table with a lamp and a big bowl containing condoms and sachets of lubricants. We didn’t waste time with pleasantries like closing the door behind us or asking names but got straight down to business.

Having seen the size of our cocks the guy decided that he wanted to be bottom after all so Jason pulled on a condom, then bent the guy over the couch before lubricating his hole and shoving his cock up him, sparing him no mercy. The poor guy cried out and wriggled trying to escape his ordeal without success. As Jason hammered away I climbed up on the couch and kneeled before the willing victim, taking hold of his head I impaled him on my own throbbing erection. I stopped for a moment to allow him to adjust to it before I started to fuck his face. Jason told me not to come and as soon as we felt like we would then we were to stop and swap places. Before long this is exactly what we had to do! I could feel pressure building up in my balls so I called time and we swapped positions. As I slipped on a condom I asked the guy if he was okay, with a slut happy grin on his face he said that he was indeed.

This time Jason sat in one of the chairs while the guy was on all fours with his head between Jason’s legs, slurping with great gusto on the naked cock in front of him. I knelt down and slid my cock easily into the guy’s sloppy hole and started to steadily fuck him. Behind me I heard the creak of the door opening and saw the young guy I had previously seen in the sauna peering through the doorway unable to believe his eyes. I motioned for him to join us and do whatever feels right for him. Needing no second telling the youth stepped inside and quickly lost his towel, his cock was resembled him, long and slender with a nicely shaped head. He stood in front of me with his cock half mast, with one free hand I guided it into my mouth and sucked it into life. It grew before my eyes but although it was nice and long it wasn’t as hefty as Jason’s, just as I was getting into the rhythm of sucking it he pulled away and walked over to the bowl picking up a condom and sachet of lubricant. He quickly donned the condom and knelt down behind me, pushing me forward a little before applying the lubricant to my hole. Just from the way his fingers moved I could tell he was no novice and sure enough before I could think of saying no he had gently and smoothly slid his cock deep inside me and was slowly beginning to fuck me as I fucked the guy in front of me. I guess this is what they call a meat sandwich; it was certainly a novel experience feeling my cock buried deep inside an arse while a cock was stuffed up mine. I looked over to Jason, told him it was such a great feeling that he might like to try it too. So there was a brief interruption while we rearranged ourselves. Jason stood up put another condom on, then willing guy crawled half onto the chair while Jason reinserted his cock up his hole, I then shuffled forward and pushed my cock up Jason’s hole, finally I felt the youth’s cock slide back inside me. For the next five to ten minutes this human daisy chain groaned and grunted before one by one we shot our loads and collapsed on top of the person in front. This impromptu orgy came to a natural end when youthful guy and willing guy made it clear that they were going to have their own private party and wandered off to another rest room for some privacy.

I smiled at Jason and then said “I don’t know about you sunshine, I have had a great time here and it’s been a real eye opener but I am bush whacked and would like to call it a day.”

Jason’s smile wavered momentarily before being fixed back in place “Sure thing old man, there’s always another time? Shall we go for a shower and then head back to yours?”

“Come on don’t be like that Jason, I’ve got work in the morning and I don’t want to be too late in getting to bed. Of course we can do this again, I’ve really enjoyed myself. Would you like to stay overnight?” I asked.

Jason laughed and raised his hands in mock surrender “Okay okay! You win and how could I refuse when you’ve made such a tempting offer?”

Taking charge of the situation I took him by the hand and forcibly led him back to the showers where we thoroughly washed off the stale smells of sex and the sauna in general. As we stepped back out into the street I was reminded of the children’s story ‘The Lion, the Witch & the Wardrobe’, this is how they must have felt stepping through the wardrobe having left Narnia behind.

Two hours later I was laying in bed with Jason snuggled up against me, head on my shoulders with one arm draped across my chest sighing in contentment. I don’t like to admit it but I was feeling pretty pleased with myself, for I had shown Jason that between the sheets not only can I be a rampant beast but I can also be a considerate lover. We had fucked each other in just about every position possible and swapping roles several times, I don’t think I have one drop of spunk left in my balls! I simply held him tight against me enjoying the moment, not wanting to break the spell. Somewhere along the line we must have drifted off to sleep because the next thing I knew was the alarm going off and the morning rush was underway..........

MONDAY 26TH APRIL 2010

First task this morning was to collect up the votes submitted by the inmates via the ballot boxes on each wing, then take them to the Governor’s office for counting and verification by Liam.

By mid-morning the twelve contestants through to the next round were: Tyler, Flick, Eduardo, Dinesh, Jarek, Tony, Bert, Darren, Carl, Martin, Gus and Sayeed. Okay folks I guess the cynical reader might say that it was all a fix but I swear to you the voting was absolutely free and the counting was not fixed in any way. I just like to think that the management got it right first time round.....

I quickly printed out the list of remaining contestants and put up the notices on each wing stating that training will begin in the chapel this evening after dinner and the twelve contestants will be given their new uniforms. The whole prison was quickly buzzing with the news and it continued throughout the afternoon right up until the time I began my welcoming speech, only then did it go quiet.

The contestants sat in the front row of the auditorium waiting to be called up one by one. Tyler and Jarek were the easiest as they were already naked and in fact they ended up wearing more than they started with! But the others were a different story. After those two Flick was next, I called him up on to the stage congratulating him on making it through to the next round and presented him with his red beret and leather belt. Shaking my hand and thanking me he made to walk off the stage as had Tyler and Jarek before him. I called him back and explained that as a volunteer punisher his uniform was the beret and belt, nothing else was considered appropriate and he would have to surrender his clothing immediately or forfeit his place in the competition. He narrowed his eyes at me momentarily, said nothing before grinning mischievously and started to undress handing to me each item of clothing until he stood there naked in front of me. Only then did I give him permission to don his uniform and return to his seat in the audience. Looking down into the audience everyone was enjoying the spectacle except for the remaining nine contestants who were less than happy with what lay ahead but knowing they had no escape route without forfeiting their place in the competition. One by one they collected their new uniform and surrendered their clothing, surprisingly once on stage they acted with good grace and didn’t show any of their real feelings. When all twelve were dealt with I called them back up on stage and lined them up in a row facing the audience.

I then made my final speech of the evening “Gentleman, before you stand the final twelve contestants all vying for the six positions of volunteer punisher. For the next five evenings we will ask you to sit in this auditorium and watch the practical training sessions taking place next door. At the end of the evening we will ask you to vote for the contestant who you consider to be the least capable or willing. The training will be filmed totally live and you will be able to see and hear everything as it happens, there will be no faking or trick photography, what you see is what is happening.”

Then turning to the contestants I said “Let’s get the show on the road, we will now make our way next door and start the training.”

There was a short round of applause which subsided into whispering conversations as I led the twelve guys off the stage, down the aisle and through to the training room. Inside waiting for us were James, Max and George positioned behind the video cameras along with Richard who was preparing the shower area. I pointed to a spare couch and told them to remove their berets and belts and place them on the couch as they won’t be needed. Briefly glancing at the cameras they did as they were told before joining me in the shower area.

“Okay guys, tonight we are going to focus on personal hygiene both externally and internally. During the course of this evening Richard and I will be demonstrating the cleaning methods that are to be used on a daily basis when you are carrying out your role a volunteer punisher. Then following the demonstration ALL of you will undertake the cleaning methods, I don’t need to remind you that every move you make is being recorded and scrutinised by the audience next door and any reluctance may cost you dearly in this competition.” I told the men who were standing in a semi circle round me.

As I allowed this information to sink in I started to remove my prison uniform, folding it neatly and passing it to Richard who stood ready to take it from me. Finally I stood in just my boxer shorts, then smiling at the others I pulled them down and handed them to Richard too. I was now as naked as the rest of them.

“Firstly, and I’m sure you all know how to do this, I am going to show you how to wash thoroughly. There is nothing more important than personal hygiene especially as you will be virtually naked twenty four seven. Then afterwards I am going to show you how to clean yourself out internally too.” As I announced this I walked over to the shower unit and turned the shower on, adjusting the flow until it was an ambient temperature.

“Come closer because you all need to see this.”

The guys shuffled forward positioning themselves so that they could all see me properly. I then spent the next ten minutes showing how to soap up every part of my body including my crack, balls and under the foreskin. Then I demonstrated how to rinse the soap off again afterwards. By now Richard had joined the group with a small pot of Crisco in one hand and when I nodded in his direction he turned the shower off and prepared the douching tube for me.

“Right guys, now comes the fun part! I am going to wash all the shit and detritus out of my rectum so that should a cock need to find its way up my arse it won’t come out covered in the brown stuff. You can laugh if you want but I expect this to become part of your daily routine and I will be doing routine inspections of your rectums to make sure you are doing this a matter of course. Richard will explain what he is doing and what you need to remember when it comes round to your turn because you will be practising the method on each other.”

I glanced round the group to gauge their reaction to my announcement but with the cameras in close proximity they were careful to keep straight faces and merely nodded in the right places.

Having connected the douching tube to the shower Richard explained to the contestants that the water flowing through it must be just above a trickle and be around body temperature, too cold and it will cause cramping and too hot will burn. Then the tube needs to be greased up and so does the anus. With that he indicated that I was to join him facing away from the contestants, then, I was to bend over at the waist with my hands pulling my cheeks apart.

Out of the corner of one eye I could see a camera moving in for a close up and out of the other eye I could see the guys also moving in for a close up. Then with that I felt the familiar touch of Richard’s fingers greasing up my hole and gently inserting the douching tube. It was at that point I heard several gasps from the guys as they realised that this would be happening to them very shortly. In a strange way I was enjoying all this attention until I felt the pangs of a bloated rectum full of water and faeces. I was told to hold it as long as possible by Richard before being given permission to evacuate the contents down the nearby toilet. This process was repeated three times, after which Richard was satisfied I was fully cleaned out.

Standing up straight I thanked Richard for his assistance and asked who wanted to go first. As no one volunteered straight away I randomly selected Eduardo and asked him to take my place in the shower area and assume the same position that I had a few minutes ago. I knelt down behind him and savoured the view of his glowing white cheeks in contrast to his brown back and legs, as he pulled his cheeks apart his ring glistened pinkly and opened very slightly. I took the tub of Crisco from Richard, placed it on the floor before smearing a glob of it around his ring and just inside, when I was satisfied he was greased up sufficiently I took the douching tube, greased that up and inserted it into Eduardo’s rectum drawing a quiet groan from his lips. As water flowed into him I gently massaged his ever increasingly bloated stomach, explaining what I was doing all the while, then when he could take no more I pulled the tube out and let him sit down on the toilet to release the water. The force in which it flew out made us all laugh releasing some of the tension in the room. Then it was time for Eduardo to assume the position again and the process was repeated for another two times before the effluent ran clear from his backside.

Deciding it was best to take charge I didn’t ask for a volunteer, instead I selected Dinesh, Jarek and Gus in that order because I knew that they had to be familiar with the process as they could all accommodate fists and there was no way to be able to do this without being cleaned out first. Sure enough they took the cleaning out in their stride and were comfortable enough with it to crack a couple of jokes with the other guys while it was going on. Then it was Tony’s turn and he was the last of the easy ones, all the remaining guys had only ever had a finger up their bums!

That was about to change, starting with Sayeed, I had a score to settle with him and he was going to be a tough one to crack. But crack he did, having seen five guys before him being cleaned out with no difficulty pride would not let him back away from this challenge. So after I crooked a finger at him as Tony rejoined the crowd he assumed the required position and obediently spread his cheeks wide. Once again I was given the treat of seeing his tight pink anus nestling amongst the black hairs of his crack. Not giving him time to react I started to grease up his hole with a generous amount of Crisco, I took my time in doing so savouring the chance to get my fingers up his arse. Slowly but surely his resistance broke down and I was just able to insert two fingers into his virgin hole, after some more warming up and words of encouragement he was sufficiently relaxed to be able to comfortably accommodate the two fingers. Deciding he was loose enough I inserted the douching tube, I made sure that there was enough of the tube up there that he knew what it felt like to have a cock inside him. He was panting from the exertion and I could see that his face was flushed as well as his neck and shoulders. Reaching underneath him, I accidentally brushed against his genitals and was surprised to find that he was erect, considering his attitude during his post punishment meeting this was not the reaction I had been expecting. However I kept my thoughts to myself and concentrated on the task at hand which was to massage his expanding stomach. All too soon he was fully loaded with water and I allowed him to empty himself out into the toilet under the watchful gaze of the other guys and the cameras. As with the preceding guys I cleaned him out a further couple of times before releasing him for his ordeal.

Flick and Tyler were next and just like Sayeed were anal virgins so they took some breaking into! With Tyler he was definitely a crowd puller (possibly because of his reputation) and when the douching tube was pushed inside more than one guy clapped and whistled. Flick was a different matter, he was more concerned with image and once he realised that he wasn’t about to lose face he readily submitted to the anal intrusion. Of the four remaining guys Bert, Darren, Carl and Martin only Bert seemed to show any reluctance in being cleaned out and he deliberately hung back until last. From my point of view it was game up for him, he had been the only one of the twelve guys to show any hesitation or reluctance, but that would be for the audience outside to decide not me, management no longer had a say in the matter.

Finally some two hours after entering the training room all twelve contestants had been cleaned out, allowed to don their uniforms again and were standing up on stage waiting for the results of the voting. I had to give the contestants credit, they all walked back up the aisle with heads held high and when other inmates called out to them they waved back in response with grins on their faces. They gave no sign of any tension as they waited for the votes to be counted. After five minutes of waiting with baited breath Liam handed me an envelope, I opened it with great ceremony and read out the one word written on the paper within the envelope – Bert. There was deliberately no indication of the number of votes he had got, it was sufficient for him to know that he was no longer in the competition. After a short thank you speech by Bert he removed the beret and leather belt and handed it to me as he was required to do. He stood there expectantly waiting for his clothes to be returned. I informed him that all the contestants clothing had been confiscated as soon as the training session had commenced and was locked away within the Governor’s office for safekeeping. Unfortunately this meant he would not be able to gain access to his clothes until tomorrow morning when the offices were open again. In the meantime he would have to remain naked until then. Consider it a booby prize for being voted off I suggested with just a trace of a smile. There was nothing he could do except shrug his shoulders and leave the stage with as much dignity as he could muster to the applause of the audience. As he left the room I closed the meeting by confirming once again that the next round would take place at the same time tomorrow here in the chapel where things will be taken to the next level.

I didn’t get home until late that evening and as I sat eating my supper I realised that I would not have time this week to join Aaron and Jason for their Tuesday and Thursday runs. I sent them both a text message from my mobile informing them that for this week only due to work commitments I would not be able to join them in their runs but they were not to use that as an excuse to avoid doing it! Aaron replied within minutes saying that it wasn’t a problem and that he’ll see me at the leisure centre as normal at the weekend. Jason however didn’t respond until much later, in fact I was just about to turn my phone off when his message arrived. He said that it was okay with him but hoped that I wasn’t getting cold feet with him after the weekend. Stupid boy! I thought to myself, I was a little more tactful in my reply however. I assured him that there was no way I was getting cold feet and it was simply down to being on late shifts all this week. He then came back asking if he could stay over tomorrow night as Kirsty was still away? Not having the energy to argue I agreed to his request, if I’m honest I was just a little bit pleased with his eagerness to sleep with me again.

TUESDAY 27TH APRIL 2010

Dear diary, I’m going to skip the boring bits of today and jump straight to this evening’s training session in the chapel. It was slightly different tonight in the fact that Adrian was acting as compere in the auditorium whilst I and the contestants went straight to the training room next door and as before they removed their uniforms putting them to one side. As with last night James, Max and George were the camera men and Richard acted as shower assistant.

Standing in front of the eleven contestants I explained to them that the first task of the evening was to clean themselves inside and out. They were expected to do it without assistance as they had been shown how to do it the previous evening. No one made a move until they heard the creak of a video camera moving, this seemed to jolt them into action and this time Tyler took the lead and stepped up to the shower and made a great show of soaping himself up and then rinsing himself off. It was hard not to stand and gawp at him, as I’ve mentioned before he is pure beefcake, black as coal and hung like a horse. Then, not bothering to dry himself he bent over spreading his legs a little and greased up his little puckered hole. Next he took the douching tube, adjusted the flow of water through it and the temperature before carefully sliding the tube deep inside him. He remained in that position until he felt enough water had flowed inside before removing the tube and squatting over the toilet. On my instruction he hovered over the seat so that I (and the cameras) could see the colour of the effluent. Naturally on the first clear out it came out brown but by the third clearout it was clear.

Not wanting to be out done Flick announced that he would go next. As he showered I could not help but watch his dragon tattoos move as his washed himself, they were quality tattoo s and seemed to have a life of their own. Before long he was cleaned out and it was then the turn of Gus, then Carl and so on until all eleven guys were done.

While the last few guys were busy cleaning themselves out I went to the metal cabinet and retrieved eleven dildos of average cock size along with five tubs of Crisco and placed them all on a nearby couch ready for the next stage of their training. Calling them over I told them that as adult males we knew that they had experience in the art of fucking in an active capacity, however in the role of volunteer punisher they may be required to participate in man to man sex in a passive capacity. The purpose of the next exercise is to introduce their anus and rectum to having an object i.e. a cock up inside them, and as a responsible organisation it is safer to do it this way than to allow them to be fucked by another inmate without having any prior experience. As I was talking I looked round the group I could see a couple of faces looking worried, one was Sayeed (no surprise there!) and the other was Martin. I mentally made a note of this to ensure they got special attention from me.

I then went on to say that I recognised that some guys had already got experience of having cocks up them and if they didn’t mind they would take the bottom role to start off with so the others could be taught the correct technique for inserting the dildos. There were no objections and I didn’t expect any given the nature of the competition so I asked Eduardo, Dinesh, Jarek, Tony and Gus to get down on all fours on the floor facing away from us with their heads on their hands. This had the effect of raising their bums in the air and exposing their holes to us, what a sight indeed, five puckered holes waiting to be stuffed. Next I instructed Flick, Tyler, Darren, Carl and Martin to collect a dildo each and a tub of Crisco and then kneel down behind a hole of their choosing. Sayeed asked me why he had not been included, I explained that I already knew that he was experienced in stuffing holes and that I wouldn’t insult his intelligence by getting him to do this exercise. His pride was intact with this assurance and he nodded his understanding. Walking over to the group I told them to liberally grease up the holes in front of them all round the outside of the ring and then to take another glob of grease and push it inside the anus with two fingers and smear it all around as much as possible. Next they were to grease up the dildo and place the head of it at the entrance, tell the recipient to breathe deeply and relax before very slowly and gently pushing the dildo inside. Keep pushing until the dildo is fully inserted up to the silicone balls, place your hand on the base of the dildo to keep it in position and let it sit there for a couple of minutes before slowly pulling it back out. I told them to leave just the head inside and then push it back in again, then, with the other hand they were to reach between the recipients legs and take hold of the cock. Next while they slowly fuck the bottom they are to stroke the cock and wank off the recipient until he cums, only then can the dildo be removed. I asked them if they understood the instructions, I simply got nods of agreement as the five guys were concentrating on the tasks at hand. It was reminiscent of a porn film watching the five guys in a row being fucked with the dildos and wanked off. After about five minutes I heard Tony grunting and then the distinctive splat of jism hitting the tiled floor, I told Darren to remove the dildo and clean Tony’s hole up using the tissue I handed to him. Watching Darren do so I noted that Tony’s hole closed up quite quickly indicating that he obviously doesn’t get that much bottom action inside! A couple of minutes later Eduardo came, followed by Gus, Dinesh and finally Jarek. However their holes were slower to close up (as I expected) because they saw more action and were capable of taking larger objects. Whilst their holes remained open I pointed out to the “tops” that this was a good sign and indicated that the bottoms were completely relaxed. Now that they were all cleaned up I announced that it was time to swap!

The “tops” were a little hesitant in kneeling on the floor but after words of encouragement from the “bottoms” they did indeed swap positions. Eduardo now knelt behind Tyler, Dinesh behind Carl, Jarek behind Flick, Gus behind Martin and Tony behind Darren. I told Sayeed it was now time for him to join the other “bottoms” and that I would be taking care of him today. He threw me a quirky smile in response before assuming the same position as the others. I asked the new “tops” if they had any questions and reminded them to take extra care with their “bottoms” as they were relatively virginal, all shook their heads before starting to grease up the waiting holes. Confident that they knew what they were doing I focused on Sayeed’s hole before me. Following my own instructions I greased up his hole and pushed two fingers inside, he reflexively gripped my fingers before relaxing again. I then replaced my fingers with the dildo and as the head pushed up inside him I am sure that I heard him sigh. I let him get adjusted to the intrusion before sliding the rest of the dildo up his rectum. As I started to fuck him with the dildo I reached between his legs to find that he was already erect and his cock was throbbing. It didn’t take many strokes of the dildo to bring him to a growling climax and a large puddle of jism lay on the floor beneath him. I removed the dildo, wiped him clean and congratulated him on doing so well. He looked over his shoulder and smiled weakly.

Once everyone had finished the exercise and donned their uniform again it was time to tidy the room up and make our way back to the auditorium for the results of the voting. This time I had no idea of who would be voted off as they all seemed to have performed okay, if pushed I would guess it would be either Darren or Martin as they had seemed slightly shy and quieter than the others. We stood on the stage in a row, with me at one side, like last night the contestants stood up straight with pride and their hands clasped behind their backs in a show of confidence while we waited for the results. Finally Liam came over and handed me the envelope, with slightly shaking hands I tore it open and read out the name on the paper – Martin. As I read out his name his face showed his disappointment but he gave me a nice smile as I shook his hand in commiseration before asking him to surrender his uniform to me. With good grace he handed me his red beret and leather belt before bowing to the audience and walking out of the auditorium to remain naked until the following morning. I congratulated the remaining ten contestants and once again closed the proceedings by inviting everyone back for the next session tomorrow evening.

Back at home I quickly ate and had a shower before texting Jason to let him know that I was ready for him to come round. Twenty minutes later there was a ring on the door bell and I let him in with a casual hello, his response was more energetic. He shut the door behind him then grabbed me in a bear hug before pushing me against the wall and kissing me forcefully on the lips.

Coming up for air, he took a step backwards grinning and said “Boy have I missed you! I’ve wanted to do that ever since I last saw you.....”

“But that was less than forty eight hours ago.” I pointed out laughing, his cheerfulness was very contagious.

“Can we go to bed now?” Jason asked taking my hand and pulling me in the direction of my bedroom.

“In a hurry or something? I thought you were planning to stay the night.”

“I am but the time for talking is later, I need you NOW!” he said hoarsely as we reached the bedroom.

He pushed me onto the bed and started ripping my clothes off. He was in a hurry but didn’t fumble once (I take this to be an indication on his experience) as my T-shirt, socks, jeans and boxers left me and flew across the room landing in a pile – quickly followed by his own clothes. By the time he joined me on the bed we both were sporting erections, there’s nothing like raw passion to get a guy turned on! He lay on top of me, supporting himself on his elbows and started to kiss me on the mouth before moving onto nibbling my neck and shoulders. Deciding to turn the tables on him I reached up and pushed his head down my body. He took the hint and kissed his way down my body and tracing my hairline with his tongue until he reached my intended target, my pulsing erection. Taking his time he repeatedly licked the shaft applying copious amounts of saliva as he did so before placing the cockhead between his lips and looking up at me with lust filled eyes. Before I could say anything he went down on me and swallowed my entire cock in one smooth movement. Aah! The feeling of his warm moist mouth and throat was heaven! I could not help but flex my hip pushing myself further (if that was possible) down his throat. He gagged a little but quickly recovered and then started to give me a fabulous blow job. Not wanting to be selfish I tapped him on his shoulder to get his attention and then told him to scoot round so we could sixty-nine.

Giving me a thumbs up he carefully manoeuvred his hefty frame round so that his crotch was immediately above my head without releasing my cock from his mouth and barely missing a beat in his blow job. I looked up to be greeted by the sight of his ten inch erection less than an inch from my face, I stuck my tongue out just managed to lick his piss slit. Reaching up with my hands I gently pulled his hips do towards me giving me easier access to him. I abandoned all restraint and energetically sucked on his cock. I don’t know how long we carried on like this because we didn’t stop after the first orgasm. The first warning I had was when Jason’s hips shuddered slightly and his cock expanded a little then suddenly my mouth was full of his salty jism. I struggled for a moment to swallow it all but manage I did and I continued to suck him until he started to soften. I thought he might pull off me but no, he lowered himself slightly so I couldn’t pull away and concentrated on my needs. By the time I was ready to shoot he was hard again and actively fucking my mouth. This cycle was repeated several times before we admitted that we were spent and exhausted by our efforts. As he crawled his way back up the bed and into my arms a thought wheedled its way into my brain and it was one that I couldn’t ignore. I looked at his handsome face and all I could think was that no matter how wrong it was or how much trouble it may cause, I was not going to let him get away from me. I’m not sure if I can at this stage call it love but the thought of letting him go is very painful to me.

WEDNESDAY 28TH APRIL 2010

Day three of the training and tonight we got the contestants, after the now customary cleaning out, to give each other blow jobs and swallow the jism before getting them to fuck one another to orgasm. Now that we were really getting down to serious action it was intensely erotic, I am sure that we could do a side line in gay porn films! Yet despite this I found I was going through the motions of being the trainer rather than being really into the scene as I had been the previous two evenings. In fact I was glad when it was all over and we were once more standing before the audience waiting for the vote. The result did not come as a shock to me, Darren’s number was up when he spat out Flick’s jism in disgust and walked over to the shower without permission to wash his mouth out. He seemed relieved to be handing in his uniform and marched off stage with barely an acknowledgement to the audience.

Back home I reflected on my distracted state of mind and I quickly realised that Jason was the cause. I just couldn’t him out of my mind nor decide what do to resolve the problems I could foresee surrounding our relationship if it were to continue. For tonight at least there is nothing to be gained by torturing myself, I will just have to have a candid talk to him at the weekend after swimming.

THURSDAY 29TH APRIL 2010

After a good night’s sleep and giving myself a stern mental dressing down I was more able to focus of today’s activities. Which is just as well as tonight’s session in the training room was a lot more intense and even more erotic (for me at least) than yesterday. We were now down to nine guys – Flick, Tyler, Eduardo, Dinesh, Jarek, Tony, Gus, Sayeed and Carl. The competition was heating up and they were clearly determined to outdo each other to ensure their place on the next round.

By now I didn’t need to supervise their cleaning out as they were now doing automatically and actually helping each other, possibly to gain favour with the audience I imagine. That left me free to help Richard get the toys ready for action as tonight’s aim was anal stretching. Each guy would have four butt plugs, ranging in size from small cock size up to large fist size, which by the end of the evening they had to be able to fully insert into their rectums with ease. I liberally greased each one with Crisco and arranged them in size order, smallest at the front and largest at the back, on the floor in a circle. This was so that the contestants could monitor each other’s progress and act as an incentive to do better themselves.

I explained what was required from them this evening, saying that each time they successfully inserted a plug they were to stand up and bend over displaying the buried plug for the group to see and for my inspection. It wasn’t a race but to pass this round each guy needed to have inserted all four plugs, failure to do so would mean instant disqualification without the need for the audience voting. The nine men looked at one another with expressions that ranged from confident to apprehensive but none had time to dwell on the matter as I clapped my hands and told them to get started.

In no time at all Dinesh, Jarek and Gus had inserted all four plugs (not surprising as they can all accommodate fists up their back sides) and were free to act as encouraging mentors for the remaining six guys who were still trying to expand their horizons if you follow my drift. Eduardo and Tony were quickly onto the third plug whilst the others were having a hard time on the second plug. It was time to lend a helping hand, so I instructed Flick, Tyler, Sayeed, Carl, Tony and Eduardo to get down on all fours with their bums in the air, as they had done on Tuesday. Then Richard and I each took the biggest plug and started to slowly and gently fuck Eduardo and Tony with them until with groans from each man the huge butt plugs sank inside and their rings clamped firmly down on the plug’s neck. We left them to get accustomed to the massive intrusion before starting to slowly pull them out and reinsert them. After about ten minutes their holes were totally stretched out and they could swallow the plugs with ease. Their ordeal was now over and were allowed to shower themselves thoroughly clean. Whilst we were doing this Dinesh, Jarek and Gus had taken the third plugs and mirrored our actions on Flick, Tyler and Carl. Sayeed was left waiting until I was free to assist. Progress was a little slower with these four as they were less anally stretched than the rest but after a lot of encouragement and words of advice they all managed to take in the third plugs. As with Tony and Eduardo we left them for a minute before starting the fucking actions. Finally they were ready for the largest plug and half an hour later even Flick was now proudly impaled on the fist sized plug. The highlight of the evening for me was when Sayeed spontaneously shot his load all over the floor as the widest part of the plug slipped past his protesting anal ring.

Tonight the audience voted off Carl, the only reason I can assume is that he perhaps showed the least enthusiasm with the butt plugs or perhaps was the least photogenic.

FRIDAY 30TH APRIL 2010

Dear diary, I can’t believe another month has flown past, how time flies when you’re having fun! Or should that be when you’re working like mad and only getting a little bit of fun on the side......

Thankfully for my sanity at least, tonight was the last evening of the training sessions and the contestants have been whittled down to seven with Tony being voted off. Again as with Carl I think it was more down to the way he came across with the cameras rather than anything he did wrong.

Last night was relatively easy as far as pushing anal boundaries go, well I think so at least, tonight was going to be the final boundary to be crossed. After being cleaned out I told them that they were going to stand in a ring facing the back of the guy in front. Then having liberally greased up one hand and the arse in front with Crisco they were going to fist each other until the recipient had cum with or without manual assistance of the fister.

Standing back I observed the daisy chain fisting with a rock hard erection, the only thing holding me back from whacking off was the fact that the three cameras were all over the place trying to record in close up detail each fist as it slid in and out of the hole it was impaling and I needed to maintain a professional stance throughout. By the end of the fistathon eight guys lay collapsed on the floor in a sweaty, dirty heap totally exhausted and spaced out for their experiences.......

Having cleaned themselves inside and out again under a hot shower, I handed them their uniforms again before we strode back into the auditorium for the final vote off. After Carl was voted off Liam and I thanked everyone involved in the competition for all the hard work that went into making it a success. Then we thanked the competitors for participating in every task set before them and pushing their boundaries so willingly, and finally we thanked the audience for their votes and we hoped they enjoyed the spectacle. We also pointed out that they had selected the volunteer punishers themselves so they had no room to complain should they not like the results further down the road! The final speech I had to make was tell the remaining seven contestants that from tomorrow onwards they will be assuming the role of a Volunteer Punisher twenty four seven and would be expected to act accordingly at all times. Next week will be their final assessment when one last contestant will be voted off leaving the six permanent punishers.

After that they were free to go and enjoy their last night of relative freedom, talking of which I was now free myself to go back to my normal shift patterns and get back to having a social life again. Okay, that can be read as seeing more of Jason........ Mmm, now that’s a problem waiting to be solved.


I very much hope you have enjoyed my story and I would welcome any feedback. Please email me at: jaypbee at fsmail dot net

Thanks.