It was the summer after we turned 18 and more than the weather got hot. Brad, Greg and I were friends and neighbors. Three horny young men and no prospects for a girlfriend in sight. We were young and our hormones were raging, so we took matters into our own hands.
I remember one day we were lined up jerking on our cocks in a contest to see who could shoot cum the farthest. I always lost that game because my cum was thicker than theirs and didn't squirt out as far, but, it always felt really good.
We lived in a rural fishing community on the East Coast and finding privacy for our adventures was easy with lots of barns and other outbuildings available to us or we could just find a place in the woods or long grass, anything that would hide us from view as we jerked each other off.
Brad lived next door and Greg was about a half mile away. Brad and I would often sneak away for a little while and usually ended up lying on our back next to each other head to foot with our right hand between the others legs grasping each other's penis milking them until cum spurted out onto bellies and hands.
One warm summer day Brad and I were playing around talking about girls and getting horny. This all happened before a lot of young women were on the pill, so talking about girls was the only girl action we ever got. Luckily for us, it was also before the HIV virus.
Being horny we found ourselves in a little meadow, hidden by some trees, lying down in long grass under an apple tree playing with each other's cocks. Brad knew that I liked to play with my ass and got up the courage to ask if I would let him fuck me. I told him that I didn't think it would fit but I was as horny as hell and said "what the hell, let's try it."
Neither of us really knew what we were doing so I rolled over on my stomach and spread my legs far enough that he could see my hole. He put his cock against my hole and pushed a little. A sharp pain shot through me and I jumped away saying "holy shit that thing is just too big."
Brad thought a little lubricant would help and sweet talked me into letting him try again. I assumed the position again and Brad put his cock against my asshole. This time he dropped some saliva right down my crack and rubbed it with the head of his cock, dropped some more and continued rubbing.
This was feeling pretty good and I started to relax a bit. Then he pushed a little again. This time he went slower and the pain was more bearable, just a stretching feeling that I thought sure was going to split my ass and I told him so. Brad assured me that it would fit.
I thought that was just his cock talking and as he started to push again I moved away an inch or so and the pain subsided a bit. He followed me as I moved and said he would try just gentle pushes then ease off. After doing this a few times there was hardly any pain. He dropped some more saliva in my crack and gave me three or four more gentle nudges and then one that was a little harder and oh my god the head was in but the giant pain in the ass was back.
I begged him to stop but he didn't pull out and the pain started to go away so I asked him not to move for minute. It hurt but my cock was still as hard as a rock and I started to move back onto his cock a little, rocking back and forth on the head of his cock was turning pain to pleasure.
After a minute or so of this I relaxed and told him to go deeper but not too much at a time. He worked it in and out going a little deeper with each stroke. When he was nearly all the way in he pulled out so that just the head was in and dropped some more saliva down my crack onto his cock before sliding in all the way.
By this time all the pain was gone replaced by a dull ache that soon turned to pleasure unlike anything I had ever felt and I never wanted it to end. I told him "don't let it come out because it will hurt too much when you put it back in."
He buried his cock to the hilt and fucked me for a couple of minutes with short quick strokes and I thought I had died and gone to heaven then the unthinkable happened. Brad's stroke got a little too long and his cock came out of my ass. 'Oh shit' I thought but he just put the head of his cock right back on my hole and it slipped right back in. It felt so fucking good I couldn't believe it.