So here's my story about the first time.
I was a Freshman in college, he was a sophomore. We had been part of a friend group in high school and fooled around back then. But now we were of age and had been skiing all day and had returned to his parent's ski house in Southern Vermont.
We did the traditional family dinner, his parents were drinking and went to bed. That left us and his brother to our own devices. We smoked some weed and probably had some beers or liquor, his dad had plenty. We smoked a few cigs and went up to our shared room upstairs. I had brought some Hustler and Penthouse magazines as well as some XXX that advertised some hot porn stuff.
We were checking them out and smoked some more weed when his brother passed out on one of the beds.
Larry and I got on the floor in our sleeping bags with a flashlight and were checking stuff out together and I noticed he was rubbing himself.
"Do you ever jerk off," I asked?
"Yeah, sometimes."
"If we're quiet, I bet he won't wake up, I'd love to see you rub one out," I whispered.
"Ok, but you have to do it also."
That was all the encouragement I needed. I immediately stripped naked and opened my sleeping bag so he could see my naked body with the flashlight. He handed me some kind of lube that he had and I began to stroke myself for him. The porn mags were soon forgotten and we took turns showing off for each other.
This went on for a few minutes and we heard his brother stirring in the bed, so we turned off the flashlight and pretended to sleep.
While we were laying there, I noticed he had inched closer and was making some body contact, which really turned me on. I decided to reach over and squeeze his ass. Apparently that was a good idea and he slid closer.
I decided to see how far I could take this and began to slide a lubed finger into his ass. Zero resistance from him or his hairless puckered asshole. I slid into him effortlessly.
"Is that your finger," he asked me?
"Yeah, do you like it?"
