Gay Shemale Stories

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My First Gloryhole Visit

by Gregjm on Sep 14, 2017
Gay Male

I visited a gloryhole for the first time last week. I was not very experienced as I have only sucked off a few shemale escorts before, and they usually don't cum because of hormonal treatments. But I was quite curious after reading about them on the web. I chose 11:30 on a holiday Friday in a sex shop. When I got there, there were a number of cars in the lot...

Straight Boy to Bi Bottom Ch. 01

by young7inchfun on Sep 14, 2017
Gay Male

This is my first story. Please feel free to leave constructive feedback and let me know if I should continue. The following is a true story, with minor embellishments, of my first gay experience. Everyone in the story is an 18+ consenting adult. NOTE: if this story encourages you to use Craigslist or another online site, please be safe. My biggest tip is i...

Experiencing Oral

by Jjdoesit1 on Aug 18, 2017
Gay Male

This story is of my discovery and my first time with a dildo in my mouth and my first experience sucking a man's dick. Yes, this story is true and yes, the names have probably been changed (lol). All subjects are well over 18. Feedback is certainly welcomed, I will answer any questions as I see them. Enjoy, JJ. ***** The question has been asked "what wa...

My First Cock in Years

by Bostonsnowball on Aug 18, 2017
Gay Male

As I was driving home after a weekend away, I started thinking about going to the Paris Theater. I was feeling very aroused since I hadn't jacked off in several days, I needed to feel a pair of lips on my cock. I had been there before and always had some guy slobbering on my cock within 15 minutes of walking through the door. I parked as close as I could, t...

Curiosity Brings a New Experience

by toddd0134 on Sep 15, 2017
Gay Male

This is the actual story of my first gay experience. The names have been changed, but everything else is as it happened. I hope you enjoy! ***** All my life, I'd always considered myself straight. Lots of girlfriends, lots of complements on my looks and plenty of opportunity to get naked with the "fairer" sex. Also, a healthy appetite for porn. It was pr...

Bob Handles Mark's Huge Tool Ch. 01

by scrotus on Aug 18, 2017
Gay Male

I had long fantasized about being involved in a sex situation with more than one guy. I had done several three ways with a woman (two guys and one girl) but they never involved the other guy and I performing on each other. In recent years, I've developed an insane desire to move beyond my several male-male encounters and add a third guy in. This is because o...

Sex with an Old Man

by johnthome7690 on Sep 14, 2017
Gay Male

Before I start I should give you some background on myself. I also want it to be known that this story is 100% non fiction. If you like the story, contact me via contact tab. I am a mostly straight man. I never have, and still after, the incident I am about to tell you about, am not attracted to men. I never walk past a guy on the streets and want him sexual...

Hot Ch. 02

by FantasyWorld2010 on Aug 31, 2017
Gay Male

********** It's hard to explain, but sucking his dick that night ignited something within me. There was clearly a sense of control over him, but the feel of his warm meaty flesh sliding across my lips and filling my mouth was intoxicating. It's as if I'm addicted to it now. The truth is that I have never wanted to try it, was repulsed by the thought of it,...

Finally My First Time

by bisibi on Nov 21, 2017
Gay Male

This is the story of my first time with a guy. My name is Simon and I'm 25, 5'10" 13st with a slightly athletic build. I had been bi curious for a long time, I watched a lot of gay and shemale porn and experimented with butt plugs and dildos while masturbating. I first became aware of my sexuality while watching straight porn and being slightly jealous of th...

Business Trip

by Diego99 on Jul 16, 2019
Gay Male

This is a true story of my 1st experience with another man while away on a business trip. Names only have been changed for privacy... *** I'm 32 years old married with kids and have been straight all my life - up to now. My curiosity about experiencing with other men started years ago because of watching porn. I was initially into lesbian porn, then threes...