Gay Losing Stories

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Losing My Boyfriend Ch. 01

by rcfox on Aug 30, 2017
Gay Male

Over the 5 years of our relationship, sex had become less frequent and far duller. The last time was maybe 8 months ago and even then, it ended without orgasm... "Stop! Get off of me." Ryan had said that last time, pushing me off of his back. "That didn't feel good... You aren't even hard." I felt a tinge of humiliation that I couldn't keep it up for him....

Losing My Boyfriend Ch. 02

by rcfox on Aug 30, 2017
Gay Male

"Did Joey respond yet?" Ryan yelled from the bathroom. I looked down and read aloud, "Fuck yes. Be there in 15." "Sweet. Change the bedsheets for me." He yelled back. I don't know what was wrong with me, but I simply complied. I went out into the hall, feeling sullen, grabbed some sheets from the linen cabinet and started changing our bed. Ryan came out,...

Losing My Cherry

by BoneyMoreOny on Aug 31, 2017
Gay Male

This is a true story of a summer experience that happened many years ago. I lost contact with the other person in the story, but never forgot him. Several weeks had passed since that first sexual encounter with another man had taken place. I found that I was thinking about that experience more as the time passed. Since that time I had seduced my girl friend...

Losing my Virginity!

by rodneysteele41 on Aug 28, 2017
Gay Male

My name is Rodney Steele. This year I will be celebrating my fortieth birthday. By my story begins a long time ago. More than twenty years ago, in fact. When I was a young stud of eighteen, fresh out of high school and looking forward to college. I was headed to one of the mid-west's better universities, on an engineering scholarship. I was also headed towar...

Losing My Cherry

by bimanms on Sep 14, 2017
Gay Male

It was 1996 and I was living on the coast of Mississippi. I had been married for six years, and my second son had just been born. I had just returned from several months at sea on a Navy ship. My wife was always exhausted and not interested in sex. I, on the other hand, had a perpetual hard on. One day while driving along the beach I happen to notice a sign...

Losing My Anal Cherry

by pescaderoblue on Sep 15, 2017
Gay Male

Mike and I had a very special relationship. In our senior year in highschool he and his then-girlfriend had invited me to a threesome which had developed into a more or less regular fucking session. After that relationship had been over Mike and I, ever horny, but without any female partners to blow off some steam, had taken to whacking off together to the...

Losing My Virginity to Brandon Ch. 01

by BlaqJm18 on Aug 18, 2017
Gay Male

Chapter 1: The Videotape I was up late trying to finish up this romantic comedy script that I had been working on for the past year, and finally, I got a great intimate scene set up for the two characters. Once I worked on the intimate scene, I had my roommate, Brandon critique the scene, but he thought it was too slow. "They need to have sex." He said to...

Losing My Virginity

by mdtchaser62 on Oct 12, 2017
Gay Male

A Chubby Chaser's Autobiographical Tale Episode 1: First Contact Hi, my name's David. I've known that I was a Chubby Chaser my whole life. I'm apparently "hard wired" for it. But, knowing what you want doesn't necessarily help you get it. This is the tale of how I finally "got it". Right after graduating High School, where I had been completely closeted,...

Losing Bets

by XxPrinceAnonomousxX on Dec 9, 2017
Gay Male

"I'll make you a bet," Giovanni said. I looked over at him hesitantly. "I bet you our team will win tonight," he said, and I thought about it, our team never wins, though. "But our team never wins." I said, and he smirked. "What are the terms of this bet?" I asked. "If you win you get a hundred dollars. If I win you have to do whatever I want for an enti...

Losing My Virginity to BBC

by DLBottom4BBC on Feb 6, 2018
Gay Male

This is the true story of how I lost my anal virginity to Big Black Cock. I wanted to give some backstory and that's kind of long but I assure you the read is worth it. It starts before I would actually end up losing my virginity. I was dating a female. For the first year of our relationship everything was pretty normal. But when she went to college and I...