Sleep Sex

From a fairly early age, I had an interest in having a sexual experience with a man. At like 10 or 11 years old, I would find ways to get porn, and I would hide it in my crawlspace. When certain friends would come over, we would jerk off together in the crawlspace, while looking at the porn. None of us ever got the courage to try more than that, and eventually we even stopped jerking off together, as we were much more focused on chasing girls.

I got to college, still having never had that one experience I was hoping to have, and during spring semester of my freshman year, I started dating a woman who would eventually become my wife. She was two years ahead of me in school, so she graduated at the end of my sophomore year. During my Junior year and the first half of my senior year, she worked in the town where we went to college, while I continued towards my degree, and we lived together. During my senior year, we got engaged to be married, and she also got a much better paying job in a big city, about 2 hours from my school. So, during my final semester, she moved away to start her new job, and I was going to follow after I graduated and found a job up there.

Shortly after she moved, I started to get very lonely, and started watching a lot of porn. Somehow this reminded me that I never got that one experience with a man I had been looking for since I was little. I started posting personal ads, back when you could do that on Craigslist, and got coffee with probably more than a dozen guys, with the purpose that we would hook up after. Every time, one of us (usually me) would get too nervous, and we would go our separate ways.

Finally, I came up with the idea that I needed something to give me the confidence to do this before I get married. I had a surplus of ambien, because doctors seemed to give them out like candy back then if you struggled to sleep, and decided that I would take an ambien before the experience, so I wouldn't get cold feet again.

I bought lube, in preparation, and made the arrangements with another Craigslist guy. He was a married guy, with a dad bod and an above average sized penis. I told him my plan, and he was totally fine with it. So, I took the sleeping pill when he said he was on his way, and gave myself an enema, in case we had sex. I left my door unlocked, in case I fell asleep before he arrived. He let himself in, and when he got to my room, I was barely awake. I was wearing gym shorts and a t-shirt. He asked if I was still okay with this, and I garbled out some words that he thought meant yes. He quickly took his pants off and straddled my chest. He put his soft cock in my mouth, which quickly got hard, and he put his hands on my head and thrusted in and out of my mouth. I have no clue how long this took place because the sleeping pill was making it hard to stay conscious. Eventually he climbed off my chest, and flipped me over and started applying lube to himself and to me. My last conscious memory of the night was feeling one of his hands spread one of my ass cheeks, while he slowly started to insert himself in me. I don't remember any pain, so I must not have stayed awake for long after he started.

When I woke up, about 10 hours later, I was very groggy, a tiny bit sore, I was fully clothed, and my asshole was still moist and sticky from the cum slowly seaping out of me while I slept on my stomach.

Somehow, this odd experience scratched the itch for me of having one day sex experience, despite the fact I didn't really participate in it. I still jerk off thinking about it, but am happily married and wouldn't do it again.