I know what you're thinking, it's usually sneaky uncle, and it's usually the older person who starts these things, but this time it was the other way around. But first let's start off with a disclaimer; he wasn't really my nephew, just a friend of a friend. I met him when he was 17, his girlfriend worked at the Subway I managed, and he and his friends asked if they could use our parking lot to practice their skateboard moves. What gay man in his right mind wouldn't let a bunch of teenage skaters play in the lot? They helped bring in business, running around with shirts off, and they actually bought food and drinks as well. Back to the story, Darrin(not his real name of course) was a hot trim red head, smooth body and long, almost wild hair. He would get off school, and come skateboard around with his shirt off, teasing the girls and some of the guys. He'd get all sweaty and worked up, then politely sit in a corner booth waiting on his girlfriend to finish work.
We developed a great friendship over the year she worked for me, so when he asked if he could have his 18th birthday at my place I was thrilled. I laid out a few ground rules, No one under the age of 17 past 11pm, when they arrived, I got the car keys along with the parents numbers and permission to be there. Underage drinking was one thing, but drinking and driving no matter what age is totally different, and not wanting parents looking for their kids was another. I only had to tell one girl NO, because her mom said no, and I didn't want issues with parents.
Darrin and his brother arrived at my place early to help clean up and get things ready. Around 9pm the rest of his invited guests started arriving. Here I was 40 years old and hosting a party with hot young men and women, I was having a great time I I think they were as well. I only bought 2 cases of beer, and one bottle of hard liquor for the birthday shot. As things started winding down, the girls retired to the spare room to sleep (yes I kept boys and girls separate) and the boys took various couch and spots on the floor. Darrin was all pumped up and said he was too tired to sleep, so he followed me to my room so we could talk and watch TV. Around 1am we both decided it was time to go to bed, and I assumed he would head out to sleep with his buddies, but he asked if I minded him sleeping in my bed. "So I won't wake anyone up" was his excuse. I was not about to say no, and instead of getting naked like normal, I left my boxers on, and watched as he stripped down to his boxers as well. We climbed under the covers, turned our backs to each other and fell asleep. I'm not sure what woke me, but I felt his arm around me and his hard teen cock pressing into my ass.
I knew he had a girlfriend, and yes we had discussed man to man sex, but I was not one to push the issue. Soon however I noticed he was humping my ass and mumbling her name, I just laid there waiting to see what would happen. Soon his hand started rubbing my chest, and stomach, and his humping was getting more persistent. I slowly reached around and his boxers had disappeared, so I pulled mine down so that we were skin on skin. His cock was hard as only a teen cock can be, and I maneuvered it so that it was between my thighs and I could feel it better. He stopped suddenly and I was afraid I had gone too far, his hand reached between us and as soon as he figured out it wasn't in my ass, he started again.
.... There is more of this story ...