Gay Sissy Stories

27,439 results
Orientation
Length
Source
Infinite Scroll

The Homosexual Sissy Wife

by jakladd on Sep 14, 2017
Transsexuals & Crossdressers

I love being the one for you, the one waiting at home for you while you are at work. The house is immaculate. My time at home is spent making everything perfect, especially me, your gay sissy wife. Gay does not aptly describe the level of homosexual submission I have towards you. Being femme and sexy for you is my constant quest. I spend hours at our home gy...

Fifi La Femme: A Pansy at Last

by pris69696 on Sep 16, 2017
Transsexuals & Crossdressers

I have written this story "Fifi La Femme-A Pansy at Last" mainly from personal experience as a mature homosexual transvestite who was a gay virgin until my early 40s. I hope that it will appeal both to extreme effeminates and the ultra-masculine men they ache to serve. Now divorced I've been living with my boyfriend Ron for three years as his gay wife and ye...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Becoming Her Whore

by ecdilettante on Sep 19, 2017
BDSM

Last time we parted, you told me that you were going to fuck me when we next met. You loved the fact that I've never been taken with a strapon and you promised to be gentle, in the beginning. It sent a shiver of excitement and fear through me, which made you smile. I can imagine heading to your small apartment, anxious and excited. I haven't cum for days a...

Steve's First Adventure Pt. 02

by gbr2004 on Mar 26, 2019
Fetish

Total fantasy. Do not read if not into gay sex, domination and forced fem. ***** After that first experience, things didn't get too crazy like I was afraid they might. I did meet with Daddy several more times in the next couple months. There were more spankings as he taught me it was better to do as told, that if I resisted things would just get worse. He...

OMG My Daddy’s a Sissy (Prequel)

by fittexanman on Aug 22, 2018
Fetish

All characters are purely fictional and of legal age (over 18). * I met Deidre during my first year in college. We were neighbors on the 1st floor of Elliot Dorm. She was an art student, and I was a business major. It didn't take us long to realize that we weren't like the others at this school. As it was located in the Southern part of the country, our co...

Mistress Aimz

by hyperpress on Aug 17, 2017
Fetish

Mistress ordered me into my chastity device. I complied. "you may not cum this week," she told me. I didn't. I was good. I used depilatory cream and removed all my leg, clit and pussy hair for mistress. It was Friday. She told me to take off my chastity and jack off into a glass. She said I could cum as much as I want Friday and Saturday, but to cum in th...

A Mistress to Obey Ch. 02

by gbr2004 on Sep 12, 2017
BDSM

This story involves bdsm and gay play. Not your thing, move on. * I can't stop thinking about what happened last Saturday. It was so much more than I expected, and frankly, I did things I never thought I would do. I had fantasized about forced fem but still was surprised how different I felt when in panties. It's just hard to feel very masculine when in a...

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

My First... Turned Me Fabulous!

by BerkeleyJanine on Sep 16, 2017
First Time

I'm lying in the bed of a man who picked me up outside a gay bar a few hours ago, listening to the sounds of his gentle, contented sleep. Contented from my having given him delicious head, contented from having fucked me with my stockinged legs wrapped around his shoulders. I'm lying here, looking at the trail of clothing that marks our evening: my strap-y h...