He responded ( along with about 20 others ). I picked him because he took charge telling me what he wanted when and how and was very specific (I hate 1 word responses, they demonstrate a lack of enthusiasm to me), was tall (6"6") and well hung (9“). I gave him my # and he called me 2 minutes later (enthusiasm is +++) I had always had fantasy"s about men with big dicks but had never even so much as touched another mans cock.

My fantasy"s mostly included being picked up, teasing the guy, being eyed like a piece of meat, and generally feeling like a slut, having him manhandle and me, hard as a rock, force me down to suck and worship his massive throbbing cock and then variously fuck me 6 ways from Sunday. Sometimes loaning me out as a gift to his big dicked friends and or neighbors for blow jobs or a whole weekend of fucking and sucking, often introducing me as his virginal nephew or stepson, sometimes in groups or taking rotating turns fucking me in the back of a van while the other (s) drive or tied to a bed like some kind of communal fuck toy.

I have always had a fantasy (unfulfilled) about being fucked in a moving vehicle. We arranged to meet at a local train station near my house at around 8pm, he told me to wear a small skirt, no underwear and the smallest tightest white t shirt I could find. I expressed hesitation about wearing a skirt as I had never been interested in cross dressing, but he assured me it was not cross dressing, just role playing. He said he didn’t like cross dressers, he liked boys in short skirts for the “access“, how their ass looked, and the venerability it made them feel and display and besides, I WAS going to do it, so into my sisters closet I went, retrieving her old plaid skirt from a school uniform several years ago and a white t shirt. I was very skinny when I was 18. At 6" and around 140lb with a 28-30” waist. My hips stuck out from my profile, my ass was round as a peach and with my shoulder length blond hair in a ponytail high on the back of my head I probably looked very feminine from behind. The fact that my sisters skirt was from her 5th grade year didn’t help, it was tight on me and way, way too short, so it rode high in the back, draping over my plump little ass in a futile attempt to cover the billowing flesh beneath .

The bottom of my little round cheeks conspicuously poking out below the thin fabric, bouncing ever so slightly as I moved . I stood under a street light near the curb, shivering nervously under my black leather jacket ( Not what he told me to wear, but it was cold ) skin goose bumped. After about a 1/2 hour a very tall, large framed man with a slight belly, big pecks, thick arms and a strong build walked past I could feel him staring at my ass as he approached and he gave me an "I‘d Like to fuck you senseless" look as he passed. I was wondering if he thought I was a girl, other guys had been eyeing me as they walked out of the station and I could feel their gaze on my over exposed cheeks.

My nipples were hard from the cold and the butterflies in my stomach were getting stronger. Exited, but nervous I tried to look sexy, arching my back and crossing my legs slightly as I leaned against a bus stop pole to make my ass stick out. I watched the stranger walk across the lot. He got into a car and drove around to the curb where I was shivering and rolled down the window. Annoyed that I was being stood up, I didn"t realize that this could be my “date” until he called out my name. I nervously walked to the passenger window of his large, dark colored sedan, praying that a security camera wouldn’t see me as my marginally concealed ass became totally exposed when I bent down to the window. “Hi” I said, as flirtatiously as I could, are you Steve? “You must be Matt” he said in a voice deep enough to make my knees wobble.

Eyeing me up and down like a dog eyes a T-bone he said “Why don’t you get in and warm up”. My heart jumped with nervous excitement as I quickly opened the door and stepped forward, eyeing the prominent bulge in his jeans. “Take off the jacket and turn around once so I can get a look at you” he said firmly. I obediently complied, dropping my jacked to the ground and spinning slowly, hoping desperately that he liked what he saw. “Bend down and show me that firm little round ass of yours” he ordered. I gasped slightly and quickly obeyed, the thought of being caught wiped from my mind by arousal, “oh, yeah!” he rumbled, staring at my tiny pink virgin hole. “Get that tight young ass in here”. I picked up my jacket, tugging down on the skirt in a futile attempt to avoid exposing my bare cheeks and giving him a flirtatious look I turned around to sit down in his car and was immediately greeted by a hand, palming my left cheek and staying as I sat down, his hand would squeeze and caressed my ass the whole way to his house.

On the ride to his place it started with him grabbing my hand and placing it on his thigh, I proceeded to rub and caress his inner thigh while resting my head on the seat back next to his shoulder, turned towards him, sideways on the seat with my right leg crossed over and my foot rubbing the inside of his calf. My ass stuck out into the air slightly, only half covered by thin pleated fabric. It drove him crazy. I lightly ran my fingers up his inner thigh and began to tenderly massage and rub the ever-increasing bulge in his pants while at the same time delicately tonguing and blowing in his ear. He almost drove off the road when he took his hand off the wheel to hurriedly undo his jeans, but I happily relieved him of that duty, pouncing on his crotch. I scooted over on the seat and leaned down toward his bulging groin, sliding my soft cheek across his chest as I tugged at the buttons to unwrap what I had been yearning for.

The hand that had been firmly grasping my ass let go now, as my ass was now sticking up in the air, totally uncovered as I half kneeled, half lay on the seat, one leg in the floorboards. If anyone was next to us in the lane they got a great view of my taut rosy ass, trembling in all its unspoiled glory. The hand came back, firmly slapping, then squeezing my bare ass and sliding down my back to my head and grabbing my cheek length, multi colored hair near the back of my head. I had no Idea what I was doing, but I knew that what I sought was behind those jeans. I fumbled with his belt, finally getting it out of the way, buttons undone, I expected it to pop out on its own and when it didn’t I went in after it. Thrusting my hands into his jeans I located the root of his cock and hastily pulled, causing him some discomfort. More gently on the second try I ran my hand down the shaft to the end and gently slid it up out of the jeans. I gasped sharply, exclaiming “Oh my god!”, in that moment his cock was the biggest thing I had ever seen, Eiffel tower eat you heart out !

My eyes were as big as plates, my chest heaved and my breathing turned heavy, drool poured from my lips as I sat awestruck, staring at this monster. He didn’t wait long for me to figure out what to do. Grabbing the back of my head as we swerved between lanes he shoved my mouth onto his cock. “It’s too big, it wont even fit in my mouth” I thought, but undeterred he stretched my little mouth around his throbbing member and thrust it into my throat. I tried not to gag but the reflex was too strong, as he continued to thrust deeper my body went limp. He let up for a second and pushing against his arm I pulled his cock out of my mouth. “You are SOOO big” I said, “I cant take it all at once, let me get used to it a little“.

He objected at first but eventually agreed to stop forcing it in… for now. After wiping my mouth and taking a breath or two I headed back down. It took both of my hands to wrap all the way around his throbbing shaft and I began to gently lick, kiss and suck my way from the tip, down the shaft to his balls, then back up again, squeezing the base with both hands, I liked my lips and sucked the head of his cock into my mouth, running my tongue around the head.

He was thick, my lips stretched so tightly around his shaft that they stung and my jaw started getting sore almost immediately but sucking on his big, hard cock made me so hot, and getting hotter by the minute that I wasn’t going to stop. My own cute little 6” cock was rock hard, throbbing and turning blue pressed against my stomach and rubbing against the corner of the velvety seat when we pulled into his driveway. If he had lived another 15 minutes away I think I would have cum just sucking his cock, I was so hot, I was practically delirious. He pulled my head out of his lap by my hair and forcefully kissed me, thrusting his tongue into my mouth and pulling me onto his lap with his free arm. I inhaled sharply and let out a load gasp as I straddled him, ass pressed against the steering wheel, our cocks grinding together under the hiked up skirt.

We kissed and fondled each other in the drivers seat of his car, door half open, middle of the driveway. The thought that the some tall, older, horse hung neighbor of his might be watching as I moaned and writhed on his lap with his tongue down my throat drove me over the edge and I came, followed shortly by him. He pushed me off his lap and as I stood up in his driveway I tried to readjust the skirt, but I was a little premature. He stood up, closed the door to the car, pants still unbuttoned and cock still hard, bouncing as he stood up. He turned towards me, placing his hand on the top of my head, Pushing me down to my knees. He was so strong, and so big, I was a rag doll. He told me to clean his cock with my mouth and don’t miss a drop.

There I was, kneeling in a strangers driveway with my ass hanging out of a stolen skirt, gleaming in the moonlight. He pulled my head closer to his dripping cock, I wondered what his cum would taste like as I moved closer for my first taste. My female friends had told me it was salty which is a taste I like in foods, “like a salt bagel with avocado”. I eagerly wrapped my lips around the head of his cock and … almost gagged. It didn’t taste anything like I thought but I knew by the way Steve carried himself that he wasn’t going to take no for an answer, so I suppressed the urge to vomit and started lapping up his musky seed. I tried to act like I enjoyed it but he knew, and made me take my time because of it. Once I had thoroughly licked him clean he quickly buttoned up his pants, said “come on” and started walking up the driveway toward the front door of the house. I followed, trying to adjust the skirt to cover both my ass and my half hard cock, which proved impossible.

The thing barely came down past my balls and as I walked my cock would lift up the front so I gave up and walked through the doorway hoping that no one else was home to see me prancing around in a mini skirt too small to cover my ass and a skin tight white T shirt that only came down to the bottom of my ribs. Thankfully, we were alone. Steve walked into the kitchen and offered me a drink which I accepted, not realizing he meant alcohol but I was so nervous that I quickly drank it down anyway, which seemed to please him. He walked toward the large wraparound couch in the living room carrying his drink and said “come over here and have a seat, make yourself comfortable”. I walked toward the couch and as he sat down he hungrily looked me up and down, fixating on my ass, spilling out from under the skirt. He patted his thigh and said “come sit right here”.

I walked over trying to be cute and sexy, sticking my ass out and wiggling it a little as I walked, which he seemed to like despite the fact that I had no Idea what I was doing. I started to sit next to him on the couch but he wrapped his hands around my waist and pulled me across his lap sideways. I liked it. He ran his hands up my smooth leg, fingers on my inner thigh, up to my hairless groin and squeezed my thigh. With one hand still fondling my thigh he rubbed my ass with the other which by now was popping from under the skirt and asked me if I wanted to smoke a Joint. I blushed and meekly nodded in agreement. He wrapped one arm around my waist, and holding me on his lap, leaned forward and took a joint and lighter from a box on the coffee table. Leaning back again he lit it, took a deep hit and passed it to me. I inhaled deeply, taking a large hit in an attempt to quash the jitters and coughed, allot. He chuckled and told me to take it easy, we had some time to kill while the hot tub warmed up. He handed me his drink which I gulped down quickly.

We passed the joint back and forth slowly for a while during which Steve continued to fondle my ass and thigh and the bulge beneath my lap continued to grow larger still. I don’t know if it was the rum or the joint or both but within a few minutes I had lost any inhibitions I had. The skirt started to feel strangely arousing, making me feel sexy, almost delicate as his strong hands slid underneath to grasp and squeeze my ass. He told me to stand up and turn around, he wanted me to dance for him and shake my ass in his face. As I spread my legs and stuck out my ass, waving it at him he slapped it hard and I gasped with pleasure. He told me to bend over, calling me a slut and started to kiss and grope my ass. The skirt was good, I felt like a slut, an object, a toy, a piece of ass and I liked it. He turned me around, stuffed my head in his crotch reached over and slapped my ass while I gasped with pleasure and kissed, licked and sucked his cock. I started kissing him all over his neck and fondling his pecks. My shirt was gone, I don’t know how. I was straddling him again with one hand on his cock and the other on the back of his neck, tongue down his throat, grinding against his lap. His hands left my waist and grabbed my ass, pulling me close.

He put his hands under my ass and picked me up. I was so surprised, I let go of his cock and grabbed his shoulders with both hands. He lowered me, sliding down his chest with my groin until I felt the thick tip of his huge cock press against my tight pink asshole. He tried to push it in, but with no lube, a big dick and a very tight hole, it was hopeless. He tried to use spit, to no avail and gravity, tossing me onto the couch with my legs in the air and pressing down with his weight but it wouldn’t go in, so he walked around to the other side, dragged my head over the edge of the couch and fucked my mouth until his cum was running down my chin. Either the rum or the pot had dulled my sense of taste so this time his cum wasn’t bad. I lovingly lapped up every drop until I had licked his cock totally clean, as ordered. He laid down across the couch and took off his shirt, when I crawled on top of him and started to kiss his chest, he pushed my head down to his crotch. We laid like that for a while, I brought him a drink and laid down with my head in his groin and kissed, licked and brushed his cock, balls and stomach while he sipped his drink and watched T.V.

After an hour or so, he got up, went to the bathroom and seeing me sprawled out on the couch with my ass in the air, came over to rub it and started to get noticeably hard. I dutifully rose off the couch and kneeled in front of him, grasping his hardening shaft around the base with both hands. As I started to tongue the head of his cock inside my mouth my jaw started to hurt and I stopped. He suggested we shower and then get into the hot tub to “loosen up my tight muscles”. I had forgotten in my delirium that he wanted to fuck my ass also and didn’t catch the reference. He warmed up the shower and told me to get in while he went to get some towels. I started lathering myself in the hot shower and was rinsing the shampoo out of my hair when I felt something warm, and hard press against my back and hands on my shoulders.

Steve pressed himself against my lathered back and rubbed his substantial cock against my ass spreading my cheeks with its girth. I was so turned on my knees got weak, but Steve had other plans. I had noticed the silver “ vibrator” shaped nozzle attached to a hose in his shower but was to naive to discern its true purpose. I was concentrating on Steve and his big dick and didn’t notice him picking it up or turning it on. He moved me over facing the shower wall and pushed me against it and down. I was only too happy to comply and bend forward, arching my back to stick my ass out and up. I thought he was going to rub me with his cock some more when he started rubbing the soap on my asshole. I felt a hard object pressing against my ass and looking back saw his hand. “Relax” he said, I started to turn around to protest but he grabbed my shoulder firmly and held me as if to say “ this isn’t optional, bitch, put your face on the wall”. “Relax” he said again.

Strangely, I was not scared but rather blindly obeyed and relaxed as he grabbed my ass with one hand and slowly penetrated me his finger. It hurt, at first. As he slowly massaged my tight little ass from within I started to get hard, and it started to feel good. “You like that don’t you?” he said in a low growl. I nodded a feverish yes. “You want it big and deep don’t you ?” he said as I writhed against the tile. “Uh Huh” I cooed as I nodded blindly. I gasped as he pulled out his finger and inserted the long slender chrome nozzle inside me and worked it around. In and out, left and right stretching my hole. I bit my lip when he turned on the water. I had never felt that sensation before - being inflated, filled by something, It strained my ass. He took it out and let me drain out when I complained. Then in and full again, and on like this until he was satisfied that I was clean enough inside to accommodate the hefty bulk of his tool. He tried to fuck me right there but he wasn’t fully hard and it just piled up against my ass so he returned to rubbing it between my cheeks.

I was worked, I asked him if we could soak in the hot tub before he fucked me because I was sore, and I was but I really just needed to relax. He agreed, possibly sensing that my first penetration had left me needing a break but more likely as a diversion to get me high so I would lose my “no”. It worked, he brought a joint as thick as my thumb to the tub and after seating me on his lap with my legs over his arms told me to smoke it which I happily did between kissing and tonguing his ear until I could feel that he was rock hard again. We stayed in the hot tub for what seemed like hours making out and grinding against each other while he force fed me what he later admitted was a “laced” joint. He never told me what with but hinted strongly at some kind of ecstasy. Whatever it was it worked. I was delirious, kissing, moaning, grinding against him. When he became concerned that my moans and squeals would wake the neighbors he led me upstairs to the bedroom. Leading me over to the bed he pulled me in front of him and pushed me onto the bed, slapping my ass as he did.

I giggled and crawled onto the bed laying my upper body on a pillow and sticking my ass up in the air. “MMM” he grumbled “ as he took up position behind me, rubbing his cock against my ass and pushing me into position. He lubed me up and rubbed some on his cock, kneeling behind me. I wanted it, bad and told him. He pressed the head of his swollen cock against my hole and pressed, failure. He told me too relax my ass, and when I told him I was he said “damn! Your tight”. More lube and another try, this time pressing even harder when I start to yell “ahh!, it hurts !” and he slowly forced it in, stretching my tiny asshole around his thick shaft. It hurt, I thought it couldn’t hurt any worse until he started thrusting into me. Not gently or progressively, all at once, hard. He looked down and realized he was hurting me and slowed down, a little. “Oh yeah!, Oh god!, you’re so tight!, Oh god your ass feels so good!” he yelled as he fucked me, hard and fast. I couldn’t speak, whimpering and panting was about it. He fucked me for maybe 2 minutes before Cumming.

When he pulled it out I collapsed and passed out. I woke up laying next to him, ass aching, still high. I got up and went straight to the shower. When I returned he was asleep and although I really just wanted to go home I knew he wasn’t going to hop out of bed and drive me so I curled up against him and laid my head on his chest, waiting for him to wake up. I must have dozed of because I woke up about 3 am and he wasn’t in the bed. The sound of a running shower filled the room and as I looked up I could see him through the bathroom door. He saw me looking and firmly told me to come join him which I did, partly because I love showers but mostly because I needed a ride home, my ass was way too sore to walk anywhere. He must have seen me walking funny because he was strangely tender when I got in, rubbing my shoulders and giving up the spot under the water. He said “you are so hot” to which I blushed and said “thanks” meekly. He lovingly washed my back, turned me around started washing my chest when I reached up and kissed him.

I don’t know what I was thinking, I just did it, and it felt good, I felt my cock stir as our soapy bodies rubbed together, caressing each other. He didn’t go for my ass at all, which was sweet considering how torn up it was from that monster of a cock. We had stopped kissing and were just rubbing each other tenderly enjoying the heat and steam. I felt his cock, it was hanging down but had begun to get hard and was trying to rise, pressing its head on my thigh. His hands were wandering around my back and shoulders and I grabbed one and put it on my ass, where it wanted to be. “mmm” he said and kissed me. I don’t know what came over me, my cock was rock hard, my breathing was heavy, loosing my anal virginity had been the most painful experience of my life and here I was, making him horny again. He released my waist and I turned around, pressing my ass against his cock and looking up at him over my shoulder. I thought for sure he was going to shove it in me again, but he didn’t. He reached his hand down and brushed a finger across my stretched out ass.

I inhaled sharply in pain and seeing this he said don’t worry I’ll be gentle. He soaped up his fingers and lightly rubbed my anus. It stung at first, but stopped soon enough as he started to slowly massage my beleaguered little ass. Slowly, gently he massaged me until it didn’t hurt anymore then slowly started to finger me. One finger slowly at first then as my comfort level rose another and then a third until the discomfort was almost gone. I was panting slightly and as the pain subsided, desire replaced it. I was fully hard, pressing myself against the shower wall panting while he fingered my hole, legs spread, ass out, I reached for his cock. It was rock hard, I soaped it up. I pulled it toward my ass and he asked me “are you sure?”. Yes, I was, I think. He was a totally different animal this time, tender, patient. He placed his cock against my soapy hole and let me slowly push my ass onto it.

Once the tip was in, I slowly worked it in and out a little at a time, each time taking a little more of his shaft as the pain dissipated. My ass was stretched around his thick shaft like a banjo string and as I neared the halfway point he was grunting with pleasure every time I pushed it in. I wasn’t sure I could take anymore because it started to hurt inside my ass before it hit its deepest point but he must have noticed because he grabbed my hips and wiggled his cock around a little inside me while pushing in. It hurt, but then I felt a pop and it slid in another 2 inches, I moaned but no more pain inside. I looked back at him to see if that pop was bad but he gave me an all is well look. I pushed his cock into me again moaning as I went, “oh god… you’re soooo big!” My ass was burning from the soap and the stretching as I pushed back on to him panting and moaning but the feeling of taking him inside me was amazing so I had no illusions about stopping. After about 30 minutes of slowly pushing and stretching I finally reached the base of his shaft and felt his balls rubbing against my ass.

I moaned and yelled “I love your big cock sooo much!”. With that he couldn’t take it any more, he grabbed my hips and started to thrust. Not as fast this time, thank god. He slowly worked up steam thrusting faster and harder till I told him enough and then stayed at that pace. The feeling of him thrusting in and out of me was incredibly intense, I felt a straining, burning feeling inside me building until I couldn’t take it anymore. I started to moan and grunt loudly and my tongue was hanging out of my mouth like a panting dog yelling “yeeeeees!, oooooh goooood!, yes!, oh my god!” as he stuffed me full of cock over and over again. “Oh yeah!, you like it big, don’t you?!” he yelled as he plunged it in deeper. “yes!, yes!” I said, “I love your big cock SO MUCH!!”. My ass started to spasm, squeezing down on his cock and he yelled “oh god that feels good!, oh my god your gonna make cum!” I let go of the wall and grabbed my cock, jerking at it wildly, Cumming over and over 5 or 6 times. “Ughh!” I heard him say as he thrust all the way in Cumming and held it there, throbbing inside me. We were fixed there for a few seconds, frozen in time. Impaled on his generous cock I leaned quivering against the shower wall, cooing euphorically.

He pulled out slowly after a few seconds leaving me feeling empty and sore. We showered absentmindedly and fell into his bed exhausted. He pulled me close to him and kissed me gently as we cuddled. Feeling secure I asked him when he could take me home. Monday he replied, I was going to stay there, he was going to spend the weekend stuffing my mouth and ass with his fat cock. I tried to argue but it was no use, He had spoken. It was going to be a long weekend for me, I could tell. My jaw was already so sore it hurt to speak and as good as it had felt the last time he fucked me, my ass hurt so bad I was sure it couldn"t take any more, but he was definitely not giving me a choice. Anxiously resigned to my fate I passed into unconsciousness draped across his sizeable frame. I woke up face down on the bed with a pillow propping up my hips, ass on fire.

He was fucking me again, hard. I guess I was out so soundly that I hadn’t woken up when he started, he had been at it for a while, I started to cum. The next 2 days and nights are mostly a blur of moaning, howling, choking, and cum as he relentlessly pounded my mouth and ass again and again. He never seemed to run out of steam. He didn’t allow me to put on clothes the entire weekend. Nude, overwhelmed and compliant, I was informed that I would promptly and dutifully satisfy any needs or desires he had for the rest of the weekend, In other words, I was his sex slave. I became a playground for his abundant manhood, I was either on my knees, lips stretched around his thick shaft, mouth bursting with swollen, hard flesh as he crammed my mouth, or moaning and groaning in delirium as he filled me to the limit with cock, fucking me in every room of the house. I softly complied, having totally surrendered my body to this large, strong and very dominant man, he moved me from room to room, fucking me on every surface in the house.

He laid me across furniture, held me in mid air impaling me or against a wall, anywhere, everywhere. When I gave him a massage, we both got covered in baby oil making our body’s slip and slide against each other, he loved it and told me he was going to keep me oiled up for the rest of the weekend, so he could slide me up and down on his cock more easily. Even when I was on top, he was so strong that I couldn’t have stopped him if I wanted to, tossing me around like a rag doll, stretching my ass around his cock until I was bursting at the seams with his meat, he pounded me until I passed out, stuffing my tight little ass with his huge tool day and night until I started cumming with every thrust, he even stopped caring if the neighbors knew. I wasn’t counting but he must have fucked me 15 or 20 times by Monday morning and I must have had 2 gallons of his cum in my stomach and ass.

I was so sore I could barely walk by Sunday and after he fucked my mouth and ass for an hour or so on the back lawn in full view of anyone in the neighborhood who wanted to look, I passed out laying in the soft grass, cum dripping out of my mouth and gaping, stretched open ass, I lay there for an hour or two for the whole world to see while he made dinner. I shoveled it down fast, he took his time. I found out why when I was done, under the table I went. While he ate his vegetables, I drank cum from his throbbing cock. He practically had to carry me to the car by the time it was over. I hadn"t showered in 24 hours and was covered in cum, lube and baby oil from head to toe.

Ass still stretched wide open, rubbed raw, red and gaping, torn skirt half covering my bruise covered ass, ripped T shirt hanging off me I looked, and felt, like I had been gang raped by an entire army. As I walked the few blocks home in broad daylight, people gawked, staring at the raw, gaping hole between my bruised red cheeks as I painfully tiptoed home, punch drunk, with my well fucked ass hanging in the breeze . I avoided my house till after my parents were gone. I hid in the bushes nearby to avoid being stared at by everyone who passed. I showered and fell asleep, my ass was never the same again. I didn"t even think about sex for at least 2 weeks... until Steve called me again.