Gay Sissy Stories

744 results
Orientation
Length
Source
Infinite Scroll

Nephew's Readjustment Pt. 14

by bart_allen on Sep 14, 2017
Gay Male

This story contains femdom, gay conversion, extreme humiliation, BDSM aspects, and frankly, is fairly extreme. If you enjoy it, please check out Power Trip, by wally_west, who inspired this story. ***** Nicholas week began with a morning session with his new plastic lover. While the bathroom made things easiest if he was willing to work, morning wood wasn'...

The Birth of a Sissy

by sissymedic1426 on Sep 14, 2017
Gay Male

After some careful planning and serious consideration I had made the decision that I would use my parent's birthday present to me to travel to Orlando, FL. They have a University there and tons of other things to see. For a kid from a little town in NC it felt like the biggest city that I could visit and still be safe (they have the house of mouse what's the...

Finding a Perfect First Daddy Cock

by btmboi335 on Apr 3, 2019
Gay Male

This is the true story of the time I lost my virginity to Mike, an older man I met on the internet. I will always remember my times with Mike. His cock was one of those rare, perfect cocks that you can always recall in your mind in a second, so every time we fucked was memorable. I hope you enjoy our first time as much as I did. ***** For as long as I can...

Was I Raped? Ch. 04

by eviltwin52 on Sep 14, 2017
Gay Male

"What the fuck did you say to me bitch?" Uh oh. I'd pissed Daddy off. I'd been whoring for Daddy for three weeks now. I can't remember the number of black gentlemen who have enjoyed what I have to offer them. Still using my hotel room, every penny I earned went to Daddy. But that was a problem. The hotel wanted their room paid for and my credit cards have...

Cum on Panties

by jakladd on Aug 30, 2017
Gay Male

Cum on Panties - Our phone sex is always so hot, you egg me on in so many ways. My wife has no idea how much I wear her panties not to mention her lingerie, stockings and dresses. We talk about what I'd wear when we get together as I suck your cock. You always have me send you pictures of me dressed in panties, stockings & high heels, telling me how perfectl...

Tame Cocksucker

by drmweaver705 on Jun 8, 2020
Gay Male

All participants are over 18. The idea for this story was suggested by donaldelliott11, with thanks. ***** "With this ring, I thee wed," Angelica said. With this yoke, I thee burden, Artie's mind echoed, just one moment forgetting the perks that came with marrying this fat, moody cow. Everything had moved so fast. Artie had the good fortune of working f...

Owned by a Ghetto Bitch Pt. 09

by FantasizeAndRealize on Aug 28, 2017
Gay Male

Tyrone moved into my apartment the next day. With his move in, drastic changes occurred to my life. These changes turned my financial, social and sexual world upside down. I go to work everyday and pay all of the bills on my apartment. Sholanda spends my paychecks to the last cent. I see all of the new things that she buys Tyrone. I barely have enough money...

Little Sex Toy Ch. 02

by keptsissy on Sep 26, 2017
Gay Male

The only sounds in the room are his loud grunts and heavy breathing. That, and the springs of my bed, my bed board hitting the wall. My soft whimpers, soft crying and moaning are drown out by all of this. My eyes closed, I keep my face buried in the pillow in front of me. "Uhg, Uhg...fuck, ooooh, Uhg...", he slaps against me from behind forcefully and very...

Becoming a bitch

by Testytesterton on Nov 28, 2019
Gay

(Skip this if you don't like boring behind the scenes stuff. Wow! Over 3000 likes and story of the week for my first story here! Thanks to everyone who has liked, bookmarked or commented. The feedback lets me know what works and what might need work. I would love for this to be the most popular story in its category, so if you like the story, "like&quot...

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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...