submitted August 8, 2000
When I was 18, my friend Billy was about three years older than me and had gotten me a job for the summer. It was a small roofing company that consisted of Me, Billy and the owner, Phil. Billy was out of high school but I still had a year to go, Phil was in his late 30’s.
One Friday afternoon we knocked off early because Billy and Phil were going up to Phil’s cabin for the weekend to do some fishing. On the way to drop me off they asked me to come along and I agreed.
We got to the cabin a couple of hours before dark. It was pretty nice, no electricity, but it was clean and roomy. There was one bed, which was Phil’s. Billy and I were to sleep on the floor, which was fine with me. Phil informed us that the fish would only bite early in the morning so we should get settled in and get up at first light.
We had supper and it was too early to sleep so we had a few beers down at the dock. By the time we got back to the cabin, I was feeling pretty buzzed by the beer. Phil suggested that we play some cards. After playing hearts for a while, Phil said, “Let’s play some strip poker”.
Billy laughed and said “Why the hell not!” They looked at me kind of daringly and I agreed. Billy was the first one to lose everything and when he removed his shorts Phil teased “Hey c’mon Bill, let's see watchya got there” he turned to me and said, pointing at Billy “ya ever see the cock on this guy?” I hadn’t but I had heard stories about him being real hung. He was a good-looking guy, well built but not overly muscular. He stood up at Phil’s prodding and thrust his pelvis out to show us his cock. It was huge. Completely soft it was about 8 inches, and thick. Then Phil stood up and showed his. It was a good sized one too but nowhere near Billy’s. At their request I showed them mine too.
We all had a good laugh. We were all feeling the beer by now and when it seemed like there was nothing else to do Phil piped up. “Hey, lets play another game of hearts”
“The loser has to jerk the other two off!” We roared with laughter and Billy eventually said, “OK, I’m in”
“How ‘bout you kid?” Phil said, daringly. I had hand jobs by guys before that picked me up hitchhiking and it felt good so I thought “what the hell”. I ended up the loser and It was decided that Phil be the one to go first. He laid on his bed with his eyes closed and said, “Ok kid. Do a good job now.” I had never touched a guy’s cock before and I was embarrassed, but a bet was a bet so I wrapped my hand around his flaccid dick and started to bring it to life. It was strange feeling Phil’s cock growing in my hand. It was also turning me on a little.
Phil’s cock was alot bigger when it got hard. It had a little head, and the shaft just below it was not very thick and it reached its full thickness a couple of inches from the head. At that point it was very thick and the entire length was about 10 inches. I was actually kind of enjoying beating this guy off and after a few minutes he blew his load all over his belly. Phil then said he was going for a dip and before he walked out the door naked he said “Ok Bill, your turn, this kid’s pretty good” Bill lay on his back on top of his sleeping bag, eyes closed waiting. Watching me jerk Phil off and anticipating his turn had Billy about three quarters hard and it was massive. There was a half-inch gap between my middle finger and my thumb as my hand wrapped around it and it soon grew to all its glory. I was on my knees beside him, the big purple head no more than a few inches from my face. I was so turned on by this monster in my hand that the next thing I knew my lips were touching the head of it and as I opened my mouth and took it in Billy moaned out loud. I could only get the head and a couple of inches of shaft in my mouth and I caressed the shaft with my lips and used my tongue on the head, while I continued to jerk him off with my hand.
I heard the door open and close and Phil’s voice say, “whoa, what the hell’s going on here?”. I was on my knees and elbows with my ass sticking up and I exaggerated it by sticking it up even more to try and let Phil know what I wanted. I could fell his presence behind me as his hand wrapped around my own cock and as he started to jerk me off he fondled my ass with the other hand. After a few moments of fondling my ass he got up and walked away. A few seconds later he was behind me again and I could feel him rubbing something cold and slippery on my ass and he began to work it into me by sticking his finger in and out of my ass.
Momentarily I could feel the head of his dick pressing against my virgin ass. The feeling was great, and as the head gained entrance it felt even better. As the thickest part of the shaft went in there was some pain but the pleasure was immense. Phil drove the length of his cock into me a few times and came deep inside me. As he pulled out Billy pulled my head off his cock and said “Don’t make me come, I want some of that ass myself.” As he positioned himself behind me he said, “I’ve wanted to do this for a long time.” Then he lubed the head of his cock and without further ado shoved it right in. As soon as the head entered my ass I could feel him coming, each pump deeper than the one before it and as he hit bottom he held my hips and pumped the last of it deep into me. Then slowly pulled out as I came myself.
I spent the next couple of summers letting them fuck my ass as much as they wanted to. We lost touch as the years went by and I am married now with a family. But I have fond memories and my wife often fucks me with a dildo to satisfy that part of me.