Gay Sissy Caught Stories

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Sissy's BBC Submission

by tawnysuede on Sep 19, 2017
Gay Male

Chapter 1 - First Contact "Tyler! Snap out of it - you're staring again, and he's noticed!" Jack's voice whispered hoarsely in Tyler's ear as the hot water from the shower drummed across his back. There were just the three of them left in the shower now. Basketball practise had been over for more than half an hour and the most of the players were showered...

Sissy Bottom Has a Nite Out Ch. 03

by lostsoul1974 on Sep 14, 2017
Gay Male

After two wild and raunchy nights at the local ABS with my fuck-buddy Eric, I still had one night left while my wife was out of town. Eric and I were both pretty whipped (and sore) after the previous two nights play, but opportunities like this only come up so often. We had gotten in late from last nights adventure and crashed in my bed without even showerin...

Sissy for Older Men Ch. 01

by sissyforold on Aug 18, 2017
Gay Male

These experiences I'm writing about, are made from my former relations with older men ( being only with older men until now:) , only names and places are not the real ones. * I should start with the beginning into the world of older gay men, which was 10 years ago, when I was 19 years old. Until then, I've been only curious and had only fantasies about be...

Caught, Blackmailed and Loving It! 001

by CSK on Sep 14, 2017
Gay Male

This story involves gay sex, group sex, semi-incest, but since the main theme of the story is gay sex, I decided to put it here. If this bother's you, please do not read any farther. Thank you and have a happy cum!!! -------------------------------------------- I loved it. I might have been doing these extra jobs to get some extra spending cash while in co...

Caught with My Pants Down

by Cumfusion on Aug 18, 2017
Gay Male

The early morning sun shone into my student apartment that beautiful May morning. First Year exams were finished, there was no more revising to do, it was relaxation at last. 'Nothing to do. This is going to be my freedom.' I thought. I would often wake up with a hard on but that morning I felt like doing something really sexy. Just lying in bed and masturb...

PIXIE Sissy Stripper Ch. 01

by EROTICbearscribe on Dec 24, 2019
Gay Male

The imposing shadow loomed over Benji blocking out the lights from the stage. "I asked you a question," a deep voice said. There were no other sounds in the club. The loud dance music had been turned off a while ago. There was only the clinking of dishes coming from the kitchen. 20 year old college student Benji knew someone was speaking to him, but the...

PIXIE Sissy Stripper Ch. 02

by EROTICbearscribe on Dec 24, 2019
Gay Male

Sunlight played peekaboo through the blinds and woke Benji from the best sleep he'd ever known. He opened his eyes and breathed deeply. His eyes adjusted to the bright light and he looked around the strange bedroom he found himself in. He noticed a fuzzy pink sweater draped over the back of a chair in the corner of the room. There was also a pair of yello...

PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

Turned into a Sissy Slut Ch. 01

by i_like_it_like_that on Sep 14, 2017
Gay Male

My name is Mark. I'm 18, and am around 140 lbs, thin, with a kind of girly ass. I began to fully embrace my love of dicks by watching hours of gay porn and at the same time embraced my feminine side by buying and hiding a lot of women's clothes. Still, by the time I was 18 and going off to college, I had not done anything with a man. It's not that I didn't w...

Drunk Friend to Sissy Slut

by olybiguy27 on Sep 14, 2017
Gay Male

What follows is the completely true story of the weekend that changed my life. This really happened to me and took place in the summer of 2008 just after graduating from high school. My name is Andrew and I was a major stoner in school. I had a lot of friends, mostly due to the fact I always had really great weed that I would get from my rich old neighbor...