Gay Sissy Caught Stories

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From Alex to Lexi Ch. 03

by oskarwild on Sep 14, 2017
Gay Male

Awakening Lexi lay in bed with the morning sunlight streaming across his naked body. He was in the fetal position and he could see Max, his new Daddy, lying on his back next to him, sound asleep. Daddy's arm was over his head and Lexi could smell the pungent odor of Max's underarm. They had worked up quite a sweat last night before finally falling asleep....

Special Inducements

by bjmichaels on May 1, 2018
Gay Male

I was reluctant, but my ex-boyfriend Brian talked me into going to his younger brothers graduation pool party. We were sitting in my car in the parking lot of the liquor store. He had bought two kegs of beer and I helped load them in the car. "Why should I torture myself staring at all those eighteen year-old hard bodies?" I jokingly asked him. "Because yo...

My Friend's Dad Ch. 04

by Kent100 on Sep 14, 2017
Gay Male

When I awoke, I was startled to see it was dark outside as I laid alone in his bed. My ass, while a pretty sore, didn't really hurt as much as I thought it might. To tell the truth, remembering what he had done to it, it just felt empty and hungry. The clock on the night stand said it was after 7:00 PM, and the first thing that came to my mind was that my gi...

First Time Fucked

by tinywhiteboi on Aug 18, 2017
Gay Male

It's a long story but I had by now been the chastised slave to my former Mistress for over 6 months. Over that time I'd been conditioned to be more and more subservient. She seemed to take particular pleasure in humiliating me in front of others, especially her friends. Most Friday nights she'd have a gathering at her house with 2 or 3 friends. I would serv...

That's My Good Boy

by Submissivegoodboy on Sep 21, 2020
Gay Male

Bethany and I arrived at the hotel early that morning. We spend the day talking, snuggling, kissing, giggling and getting ready. Around midday I go into the bathroom and shave my body, we want me to feel extra sexy and feminine for my first time with another man. Mmmm as I come out naked and smooth Bethany giggles and jumps up and runs over to me. After sl...

Crossdresser's Unexpected First Time

by kprice1984 on Nov 27, 2017
Gay Male

Just want to say firstly, that this story is 100% true. Secondly, it was much better in person. I'm just getting around to writing it after several years. ***** I'm a 20 year old guy, very good looking, easy to get girls. Brown hair, green eyes and a sexual appetite that's hardly ever satisfied. I had always had a craving or tendencies towards being a lit...

Research Pt. 02

by eviltwin52 on Aug 18, 2017
Gay Male

Please read Research part one first. ***** "So in summation I submit that although a certain portion of the male population engages in homosexual acts, they aren't homosexual at all. No, they are under-endowed males who wish they could have heterosexual relationships but whom women shun. Through aggressive parenting, peer pressure, and social activities th...

Fantasy Out Of Control

by gbr2004 on Aug 18, 2017
Gay Male

I'm a divorced man living in Las Vegas. Recently retired, live alone and live a relatively normal life. I'm in decent shape for my age, 5'8", 180, and stocky build. I have been straight for the majority of my life. For the last few years, I have started to think more about getting together with another man. It goes beyond just this, as I want to be submissiv...

I Turned Myself Out Ch. 03

by drmweaver705 on Aug 24, 2020
Gay Male

"Warning: this video is designed to turn straight men into gay bottoms. Don't say you haven't been warned..." The female narrator had a breathy, clear, commanding voice. It was a voice to be obeyed. "You've stripped yourself naked and stretched your ass in preparation for the arrival of your first ever top..." In fact, I was naked, lying in the marital b...

How I Became a Sissy Slut

by DixeenormousToo on Sep 15, 2017
Gay Male

I wish I knew I had these sissy urges when I was younger. Who knows, instead of getting married, having kids, and living the "American Dream," I might have discovered hormones, worked my body into shape, and become a tranny porn star. After all, how often does the American Dream really work out anyway? I'm unhappily divorced, my oldest is on his 6th year of...