Gay Cross Dressing Stories

3,703 results
Orientation
Length
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Infinite Scroll

How Did I Get Here

by bart_allen on Oct 15, 2017
Gay Male

I found Wendy on OKCupid. She was just another face as I scrolled down, albeit a fairly attractive one. I clicked on her profile, glancing over it: she was older than me, which is not usually my type, and she was six years older than I at thirty two. She had a darker natural red hair in shoulder length cut, but a sort of light olive complexion, and pouty lip...

An Old Friend Ch. 02

by jjdtx on Sep 14, 2017
Gay Male

Chapter 2 – The Next Day The next morning, Joe left early for work and I didn't have an appointment until late in the day. So, I lounged around, looking at his DVD collection. In a small box, I found his porn stash. It was a nice selection of compilation DVD's. About twenty in all, most were straight cum shot movies, but there were four bi movies. All were...

Bathhouse Observations

by glory_first on May 12, 2020
Gay Male

The baths are undoubtedly the easiest place in a city to have male group sex, after allowing for individual circumstances during any single trip. After more than a hundred visits over the last few years, basically all of them involving satisfying sex with other men, often writing about the experiences afterwards, leads to a few general observations. Visitin...

First Time in a Long Time

by twotimeloser on Dec 24, 2019
Gay Male

A little about myself. I am a panty wearer. I love everything about women's panties and sexy men's underwear. A few years ago I stumbled upon a very popular app, where members can share photos and began posting pictures of myself in panties and lingerie. I have been identifying myself as bisexual most of my life. But, at 54 years old, it had been since my te...

Stick Shift: Storge

by zackjack on Aug 30, 2017
Gay Male

Cal leaned over me, rippled chocolate stomach muscles sweaty on my lower back and buttglobes, ten-inch manmeat throbbing fixedly inside my cum-glistened bare ass. My arms extended straight down on to the bed, supporting us both as I kneeled before the greek god fucking me. His long dark thumb still wrapped around my dickroot as my piece pulsed out a final...

Winners and Losers Ch. 07

by bawdybloke on Sep 15, 2017
Gay Male

If you have missed the previous instalments the premise of the story is that after a football match, the losing team must provide sexual relief for the victorious players. Previous chapters for Winners and Losers are on Literotica. * * * * * There was no denying that the last minute loss to AFC Kerlon had dented confidence in the dressing room, but when...

Fair Is Fair Ch. 05

by bgdddy_2000 on Sep 18, 2017
Gay Male

This is a story of married men having gay sex and it's pure fiction. If you are offended by this kind of story, read something else. Any inference to actual people is purely coincidence. Since this is not reality, safe sex isn't practiced. In real life, always use condoms and practice safe sex. ***** Here I was on my knees, with hard cocks pressed against...

Becoming a Gal Friday Pt. 03

by Showoff888 on Sep 14, 2017
Gay Male

I just turned twenty, was in a relationship for almost two years to a hot older commanding bitch who was ten years my elder. We had great sex but she left me for an older and richer man. I also lost my job at the law firm were we both worked, probably due to her efforts, I was just an office person there. Now I'm out of a job and have to move out from sleepi...

The Slut Inside Me

by Abaddon89 on Oct 21, 2019
Gay Male

Editor's note: this story contains scenes of incest or incest content. * I was caught. The excitement of doing something naughty combined with the potential of being caught reaches a fever pitch when you actually are caught, because it's both what you dreaded with every fiber of your being, but also of course secretly wanted. That's the line you tread, lik...

Infomercial

by kicky1000 on Aug 31, 2017
Gay Male

I'm the best cameraman in the country. I know it. Everybody knows it. So it did not come as a complete surprise when North American Pharmaceuticals offered me a ridiculous amount of money to film a new infomercial. North American Pharmaceuticals had a new product on the market. A breakthrough product. It was going to be a blockbuster. It was a brand new typ...