Caddy sleep over

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.