Alphabetical Listing of Gay First Time Sex Stories - Page 10

Though it was seasonal work, we knew we could always get summer jobs to provide us with round-the-year income. The Berkshires are beautiful all four seasons and the thought of living there for a few years, after living in a cramped Manhattan studio apartment for the previous two years had us both in the best of spirits.
4.3 2897 words 13 mins beginnings

One day we were at his house and his mom had just left for work, we were in his room playing his game. MK asked me if I could keep a secret and I told him yes and he said that he had a crush on me and that he thinks about me alot and being inside of me.
3.5 284 words 1 mins beginnings & friendship

Joey was a 20-year-old homeless man. He turned to prostitution and selling drugs to stay alive. At 35, David was a self-made millionaire. In high school he had made a major invention and turned it into a major empire. David lived alone and had never married. He had a few relationships with women, none had lasted very long and none were satisfying sexually.
4.1 3201 words 14 mins beginnings

This particular story was of the first time I met a hunk of a guy who I fell head over heels for. Back in 2010 at the ripe young age of 27 I befriended a guy on a social media app for gay men looking for NSA action. We hit it off immediately and our conversations quickly turned steamy.
3.7 2081 words 9 mins

He was a 48 year old married man with balding hair and a black beard with some grey. Although he appeared to be a little on the chubby side, he actually had a solid thick body. I had just finished my first year of college, and since it was now summer, I rode my bike whenever I could around town.
3.6 2992 words 13 mins

He made an appointment with Dr. Drew Right, a psychologist. Dr. Right thought he could see the problem as soon as Jeff walked into his office for his first session. Even with all the experience and years of schooling, the Doctor was still amazed how a person could not get their brain to state the obvious to them when everyone else could see it plainly. Dr.
3.9 1069 words 5 mins

I went into the bathroom and did my usual hoping to see dick. A guy came to the urinal beside me and pulled his out. I don't know if he peed, but even though other guys were in the bathroom, he was stroking his limp dick. I couldn't believe it. He wasn't hung, but I was very entertained. He further surprised me as I could hear him moaning.
3.8 4048 words 18 mins encounters & interracial

I'm 19 years old, 5'11", 185, muscular, smooth, brown hair, blue eyes, nine inches, cut. My nickname is "Bub," short for bubble, well bubble butt. Did I cover everything? I hope so. This is my first time telling somebody about a sexual experience and I'm a little unsure as to what I'm supposed to say. I guess you folks want the story, so, here we go.
3.9 3222 words 14 mins college

I had just turned eighteen. Young, naive, and always horny, that was me. I had sex with only one girl just before I joined the navy. It was good for me, but I don't think she enjoyed it much. I was too clumsy and thinking of my own pleasure. I was only 5'4" and had a slim build (120 lbs).
3.9 3676 words 16 mins domination & military

All three of us scurrying around like rodents trying to get our suitcases packed. I remained relatively quiet as I threw my shampoo, hair brush, and other things into a bag. I could hear Cheri and Christina yapping away in the other room. "Uggh, I'm so excited summer is finally here!" Christina said. "Oh I know!" Cheri beamed as she threw her astrology book into her suitcase.
3.9 8372 words 37 mins beginnings & college & relationship