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Gay stories > Category : Gay boys > Caddy sleep over
By david pavlick, 0 Reviews Post your review

I felt like I had been pulling the same clothes on every day of every summer for six years. Of course it is impossible to wear the same clothes for six years. Yet here I was pulling my caddy clothes on again getting ready for another Saturday at the country club. It’s the same routine I’d followed since I’d found caddying as a skinny 12 year-old. 

The unofficially required uniform of cut-offs (or shorts if you were a sissy), t-shirt and tennis shoes was dictated by the older caddies. It had a certain economy about it and I economized even more. I wore just that, no more no less, no socks, no underwear, just that. I loved the feel of the denim rubbing on my dick, the coarse seams in the crotch tickling my balls. 

When I first got out of bed each morning I would stop in front of the mirror and pose, staring at my cock as it stood pointing at the ceiling. I loved looking at my hard flat stomach grooving down to a cock that seemed to grow longer every day. My face and neck were nut brown from the summer sun while my stomach and thighs were creamy white. We called this a looper’s tan (caddies were called loopers). I struggled to zip the zipper on my cut-offs without maiming myself and wondered why cut-offs were always a size too small. 

Finally I got the zipper safely closed and put on a clean t-shirt. I slipped on my worn tennis shoes and was out the door in a few minutes. The cool morning air hit me like a slap in the face. It smelled moist and clean, the first rays of early dawn caused the dew to sparkle on the manicured lawns. The walk to the golf course was short and made shorter by the beautiful clear morning sky.
The sounds of the caddies arguing and grab-assing floated on the air as I approached the caddy yard. It was always a happy sound to my ears. 
The caddy yard was nothing more than a square patch of asphalt with a basketball hoop on one end and benches around the perimeter. A square table was planted in the ground in a corner and there was a hot euchre game started already even though it was still only 6:30 in the morning. The guys who got to the course the earliest had the best chance to get 2 or even 3 caddy jobs that we called “loops”.
I turned into the opening in the chain link fence and spotted my buddy Lenny sitting on a bench
I walked over to where Lenny was sitting, 
“Hi Greg” Lenny was leaning his elbows on his thighs and didn’t look up.
There was a new kid sitting next to him, “Move it maggot” I said glaring. 
The kid gave me a dirty look and moved to another seat. He was a kid in his first summer of caddying.
First-year kids stood out and could be quickly spotted their first day at the club. They were usually pale pudgy shy kids in jeans and sports shirts. 
Their body would change by summer’s end. Dragging one or two 40 pound bags of clubs around a golf course every day all summer had a way of turning their pudge into hard lean muscle. Their bellies became flat six-packs and the brown skin on their arms and legs clung tight to the sinewy muscle. By the second year they had the body of a caddy.
Usually on the first day the new kids would be taught how to dress for work. It was the caddy initiation that almost every kid went through it. Before the course opened the older caddies would escort one of the new kids to the 18th green depantsed them. The naked kid was rolled in a sand trap while the legs to his jeans were cut off at the knees.

Lenny and I were friends and we came to the caddy yard together 6 summers earlier. We were treated with respect by the newer kids. Of course they knew we’d kick their ass if they didn’t stay out of our way.
We sat making talk as friends do.
“Whatd’ya do last night?”
“I was out with Darlene.”
“Who?”
“ You know her. She gave Big Skip that blowjob. I tried to get her to go down on me but the best I could do was cop a few feels. My balls are still aching I am so horny.” Lenny rubbed his crotch.
I laughed and told him he could have done what I did and stayed home visiting Rosie Palm. You could always get a little from Rosie.
I loved Lenny talking about sex with me. It turned me on to hear what he liked in a girl and how hot he’d get. His nuts were always aching. I would fanaticize that someday he was going to pull his cock out and ask me to give him some relief. I would, of course, what friend wouldn’t help out a buddy? Lenny never suspected relief was sitting right next to him.

The bags were starting to be assigned to kids and quickly enough Lenny and I were each given two bags with a foursome playing together that morning.
“Greg, Lenny, give these people a good loop, they’re new members. And don’t get away tonight without checking with me. Maybe we could get together after I close.”
The assistant caddy master, Mike, was handing us the bags. Lenny and I had known Mike for at least five years but hadn’t really hung out with him. Mike was one of those neat-as-a-pin guys who caddied in pressed shorts and sparkling white t-shirts. His light freckled skin and short red hair didn’t lend themselves to long hours in the blazing sun and he was always sunburned. The caddy master took pity on Mike this summer and made him his assistant knowing Mike would be leaving for college in September.

“Wonder why he wants to hang out with us tonight?” Lenny kind of mumbled walking the bags to the first tee.
The loop was a breeze, the weather was comfortably warm and the time flew. 
In no time we were trudging up the 18th fairway. The golfers were good and the course wasn’t crowded for a change. After the golfers finished the hole they put their balls and tees away and then each of them gave Lenny and I a couple of dollars tip. We got $7 more from the pro-shop and it made for a nice profitable morning.
“That was fast guys.” Mike was counting out our money “You guys like beer don’t you?” 
Lenny and I just nodded. 
“How ‘bout us getting some beer and hangin’ out here drinking it and then sleeping over at my house?”
Lenny and I looked at each other and back at Mike and then shrugged our shoulders. 
“Ah, yeah Mike, that’d be fine. Right now, I need another loop” I took my money and stuffed it into my pocket causing the denim to stretch tight around my dick. Mike was staring as I struggled to get my hand out of my pocket without the money.
I got out on the next loop out with a couple of new kids who only carried one bag each. One of them was the kid I chased from his seat. It was great, they had to tend all the pins and rake the traps. 

This loop took a little longer. The course had gotten more crowded and the time dragged. Finally we walked off the 18th green.
“Thanks boys” one of the men was handing dollars to the two kids, “and this is for you” he said handing me a five.
“Ah, thanks, Thanks a lot” I stammered. A five dollar tip was a lot in those days. 
I sat and relaxed on the bench in the caddy yard waiting for Lenny to finish his loop. The two boys who’d been on my loop were talking excitedly to a couple of their friends and pointing. They didn’t like me and were mad that they did all the work and I got the big tip. Every now and then one of them would shoot me a dirty look. Each time I just flipped them the bird which made them even madder.
“Hey Greg,” Mike called me over to the pro shop, “why don’t you and Lenny help me put bags away until the course closes? I’ll pay you $5 each”
“Yeah, ok” I hopped over the half door into the air conditioned pro shop. Helping with the bags was always fun and an easy way to add a little to the day’s take.
Lenny finally brought his bags to the window.

“It’s about time, you guys get lost or what”
“Aw the fuckers were so bad. They must’ve shot 120 each” Lenny rubbed his bag stained shoulders. The straps from the bags and sweat mixed to create dark stripes on each caddie’s shoulders. You could always spot the guys who hadn’t gotten out (on a loop) by their clean shoulders.
“Mike wants us to put away bags ‘til the course closes, 5 bucks. Hop in”
Lenny hopped over the door “Oh yeah, the a.c. feels good”.
He grabbed a cold soda and popped the cap and ripped off his t-shirt while sprawling on a pile of golf bags.
“I gotta rest a minute” he said.
I loved watching him stretch out. His legs were splayed in every direction while his cream colored stomach pumped with each gulp of pop.
“What’re you staring at fucker? You want some of this?” Lenny put his hand on his crotch and humped his hips in the air.
“I just want a sip of pop, you perv,” I turned away pretending to take care of some golf clubs.
We finished bringing the last of the golfers’ bags in and started closing up the pro-shop.
“Meet me on the first tee. I’ll lock up and go get some beer” Mike was slamming doors and clicking dead bolts.
Lenny and I hopped out the back door and headed to the tee to stretch out under the stars. It was a beautiful balmy night and the full moon gave the course a ghostly look.

Mike returned with the beer in no time. 
“Here we go” he said handing each of us a bottle. “I picked up some subs too”
We hadn’t eaten all day and dug into the foot longs. No one talked while we gobbled down the subs, washing each bite down with gulps of beer
We all got a quick buzz after only two beers. By the time we had finished the subs we were giggling and burping. We opened beer after beer and babbled about golfers and the course and school. 
Mike kept turning the conversation toward sex “So, you say you were in sixth when you first jacked off Greg? How ‘bout you Lenny?”
“I guess sixth, I don’t remember. It’s been too long ago.”
“How many loads?” Mike pressed. “How many loads do you think? A thousand?”
“Geez Mike i don’t know. What’s the diff?” Lenny took a long swig and turned away.
Mike switched to me “How many times have you gotten off in at one time, Greg?”
I thought a minute “Three, maybe four times” . I knew it was three but three didn’t sound impressive.
“You, Lenny?”
“My record’s six.” he said matter-of-factly while burping loudly.
“Jesus, Lenny, six?! You must’ve been bloody.” I can’t believe anyone could do it six times.”
Mike moved over to Lenny who was on the ground leaning back on his arms.
“You must have scars. Let’s see” 
“Yeah, let’s see” I chimed in hoping for a chance to see Lenny’s dick.
“There’s no scars. It was barely sore” 
“Prove it, prove it, prove it” Mike chanted leaning over Lenny
I picked up the chant “Prove it, prove it, prove it” 
Lenny gave me a dirty look and stood up, “You guys are queer. Here take a look”
Lenny flopped his pecker out of his cut-offs. It had a nice long neck and a pink rimmed mushroom head. The head was quite a bit bigger around than the shaft. 
Mike and I stared at his soft cock.
“There’s a scar. Mike pointed his finger being careful not to touch and violate any etiquette.
“It is not. That’s a birth mark. Fuck you pervs.” Lenny turned and zipped up.
“You guys are staying over aren’t you?” Mike asked while he picked up a couple of empties, putting them into a bag.
“Yeah, I’m too drunk to go home.” Lenny answered.
“Me too” 
Mike drove us over to the house that he shared with his mom.
“Don’t be too loud. Mom’s asleep”
We all quietly slipped in the front door and made our way to the bedroom giggling.
Mike kept putting his finger to his mouth trying to hush us while giggling himself.
Lenny and I stopped to use the phone telling our folks where we’d be that night.


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We made our way to Mike’s room. He closed the door behind us, “Just keep it down guys, ok?”
Mike pulled his t-shirt off ,“I need a shower, anyone else?”
“Yeah, I can’t sleep smellin’ like this” I said sniffing my pits.
“Not me, I’m good for another day” Lenny was bouncing lightly on the bed.
“Bullshit” I leaped onto the bed grabbing Lenny in a bear hug and pulled him down on the bed. “You’re stinky. You’re getting a shower” 
Mike was laughing while he grabbed one of Lenny’s legs and pulled his tennis shoe off.
Lenny struggled, twisting to free himself.
“Ok, ok I’ll shower. Just let go” Lenny said trying to pull away.
“I’m glad that’s settled.” Mike said letting go, “Guests first. Lenny, then you Greg and then I’ll be last"
Mike tossed Lenny a towel. He quickly removed his shirt and shorts and wrapped the towel around his waist, padding off to the bathroom.
“I got the bed” I declared.
“You guys take the bed, I’ll sleep on the floor.” Mike was being the good host.
Lenny came out of the steamy bathroom rubbing his hair with the towel “I’m not sleeping with him, he’s a perv.” Lenny grinned “really though, I’ll sleep on the floor, I don’t mind”
Seeing Lenny’s lean smooth body completely naked really got me hot. I was hoping Mike would insist Lenny share the bed with me but he didn’t.
“Yeah, ok, I’ll sleep with the perv.” Mike shot me a grin. Disappointed I flipped him the bird and smiled weakly.
I took my shower and washed my dick a few times too many strokes causing it to get rock hard. I was enjoying myself when interrupted by Mike pounding on the door.

“Hurry up in there. I want a shower before morning.”
I shut off the water and began drying. My dick finally went down and I felt I could open the door. 
“About time” Mike brushed by me while I was still in the doorway. His body felt good rubbing on mine and I shivered when his dick brushed my thigh.
Lenny had already snuggled into the quilts and pillows and was just laying on his back with his hands behind his head. He looked so inviting, the soft tufts of brown underarm hair contrasted with his clear white skin. I just wanted to crawl in with him and snuggle up. 
Instead I finished drying and crawled under the covers.
Mike finished showering and came out with the towel draped around his shoulders. The light was soft and it gave his red pubic hair an orange glow. He looked great in the dim light and I found myself getting a hard on looking at him.
He flipped off the light and slid under the covers next to me. He was naked and in bed with me. My mind raced with possibilities. I figured I’d let him fall asleep and then I’d let my hands do some exploring.
“Night guys, see ya in the morning.” Mike said softly pulling the sheet under his chin.
Lenny was making the deep breathing sounds of early sleep. He was out already. 
I started breathing deep and then began making soft snoring sounds hoping Mike would think I was asleep. I figured after he dozed off I’d check him out. I kept the fake sleep noses up for a few minutes while listening for any sounds of sleep from Mike.
Then I noticed some gentle movement on Mike’s side of the bed, a very subtle rhythmic bounce. It only took a second to realize Mike was jerking off. I couldn’t just lay there and let that happen. I tried to continue to sound asleep while very slowly moving my hand over toward Mike. I finally brushed his forearm. 
“Oh Greg, you’re awake. I’m, I’m embar.........” Mike started to stammer.
My hand moved down his arm to his hand and he let it fall away to his side. I reached my hand toward his dick and my fingers wrapped around it. I was amazed how much it felt like my own dick. 
“Greg, you like to ah. . . this?” Mike whispered while I stroked slowly.
The end of Mike’s cock was wet and slimy. I put my palm over the end and cupped my fingers around the shaft and stroked a few times. I knew I wanted to taste it. I had to taste it.

I put my head under the sheet and moved quickly toward my goal. I could smell the soapy scent from the shower as my face arrived at Mike’s crotch. I pulled the end of his dick toward my mouth and put my lips on the tip. It tasted sweet and salty. It had a delicious after taste that filled my throat when I swallowed. My mouth hungrily slid down the shaft and when the head entered the back of my throat I gagged. 
Mike threw the sheet off of us and I crawled over straddling his legs. I squatted down and took his dick in my mouth again. Mike hummed softly in pleasure.
I was working my mouth up and down Mike’s dick when I felt something press between my ass cheeks. I hadn’t noticed that Lenny had awakened and moved around behind me. He was rubbing his dick all around my ass.
“I can’t let you guys have all the fun. This should take care of my aching balls.” Lenny said poking my ass with his dick but missing the spot, I needed to help him. 
I tried to position myself to help his aim. I hadn’t ever been butt fucked but the idea turned me on.
Mike put his hands on my head to remind me what he wanted. He was moving his hips causing his dick to slide up and down my throat gently. I was working hard to keep my lips over my teeth.

Suddenly a sharp pain told me Lenny had finally found his way. He gave a shove pressing the head of his dick into my tight hole.
“Agghhhh!” I tried to protest with Mike’s six inches buried in my throat. 
Mike shoved his dick into my throat hard pulling my face into his pubic hair. The only sound I could make was a throaty gurgling.
At the same time Lenny was not about to go away with aching balls again. He increased the pressure and his dick began to slide in deeper.
Tears filled my eyes as a searing pain flooded my body. My teeth were bare and I began to bite on Mike’s cock reflexively.
“Owww, don’t bite dammit” Mike got my attention with a slap on the back of the head.
The pain was beginning to subside as Lenny rested with his dick buried deep inside me. He began to slowly stroke and got into a steady rhythm. It felt good, I had wanted him for such a long time. 
Tears from the pain rolled off my cheeks as I came back to my senses. I tried to work with both guys as they synchronized their stroking. They each pushed and withdrew together. 

They started moving more quickly and I knew they were getting ready to cum. Mike hardened and swelled in my mouth as he raised his hips trying to drive his dick even deeper into my throat. He groaned as he shot a huge load that nearly filled my mouth. I swallowed the best I could to make room for more but it was no use, plenty was dribbling out the corners of my mouth.
At the same time Lenny was slamming hard into my ass and I felt a warm liquid flood into me as he shot his load deep inside. Each of them kept the steady stroke as they emptied their balls. 
I rolled over onto the bed feeling hot, exhausted and flushed. Cum was drooling out the sides of my mouth . My ass burned from the hard fucking it had received and cum leaked down my leg.

Laying on my back I breathing heavily with my eyes closed when suddenly I felt my cock being sucked into a warm wet place. It caused shivers of pleasure to coarse through my body. I was thrilled to see it was Lenny and immediately began a long, steadily intensifying orgasm. Entering another dimension I felt long streams of electrifying satisfaction flowing from my body. Spent, I lay there happily exhausted. 
The three of us fell into a deep sleep clinging to each other in total exhaustion. By morning three cocks were crowing, eager to welcome a new dawn.


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