Gay Chastity Stories

28,507 results
Orientation
Length
Source
Infinite Scroll

Sissy Life Pt. 02

by sissymark79 on Sep 19, 2017
Transsexuals & Crossdressers

I scurried to the bathroom, tears streaking my face. I was dripping cum on the bedroom floor as I went, but I didn't stop. I just wanted to get out of the room. I couldn't believe how badly things had gone! 20 minutes ago I was stood in my May babydoll, black stockings & red heels set for some intimate time with my wife, my Mistress, but now? Now things were...

End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...

XXX-Women Ch. 03

by scatwoman on Sep 14, 2017
Celebrities & Fan Fiction

NOTE: is you just wanna get to the nasty stuff, you can skip the marked-off section that deals with the background and set-up... * * * * * The Premise: XXX-Women After founding the original X-Men, Professor X was often found to be missing or believed to be dead or off on some secret mission he told no-one about. In truth, Professor X was training an enti...

Letter from Eisengrim Township

by justincbenedict on Sep 17, 2017
BDSM

Dear Shoeblossom: Sometimes Brearley lets me jerk off. Kneeling on the hardwood floor on my bare knees, rubbing my stiff and long denied cock, it's so painful! Brearley is always gorgeous, fully clothed as a striking contrast to my nakedness, in tight jeans or a sexy miniskirt, sometimes a tube top. Often she will wear a sexy business office outfit, which r...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

Black on Black Cuckolding is Nice

by Samuelx on Apr 3, 2019
Group Sex

Don't believe the stereotypes, ladies and gentlemen. Black cuckolds do EXIST. My name is Jeanette Langlois and I'm a woman of Haitian and French Canadian descent living in the City of Gatineau, Quebec. My mother, Annabelle Jean was Haitian and my father, Roger Langlois was white, of French Canadian descent. I guess that technically makes me mixed but I alway...

One Glass of Wine, Revisited

by sublocked on Sep 14, 2017
BDSM

Note to reader: My last entry, "One Glass of Wine?" was not very good. That was partly because it was hastily prepared in fantasy mode. This version, "One Glass of Wine, Revisited" (without a question mark) is, I think, better and here is why. The first was fiction, with things added that I would like to see done to me. But that is not up to me, so in this s...

Lucy 01

by Gullos on Sep 12, 2017
Fetish

I – Forcing Dan into my cumslut It is incredible. Unbelievable what just happened on the last weekend. A big milestone turning hubby into my private little cumslut. And the best thing: He hates cum, what makes me even hornier every time I think about it. The more persisting he is in not being gay, the more fun I have thinking about the plans I have for the...

Transgender Avis's Incredible Power

by justincbenedict on Jul 4, 2018
Transsexuals & Crossdressers

Skokie, Illinois, 2009 Aiken Aycock was sad to be losing her brother Aiden to the operation. He was a great guy, but he gave Aiken the beatings and torture she needed. But he'd finally gotten the money to do the big change. Aiken had really enjoyed supporting Aiden, letting him live in her apartment...stripping naked when she got home, and taking a few fro...

A Tale of Slavery

by gunnarsub on Sep 17, 2017
BDSM

Once upon a time there was a straight guy who was known by everybody as a well respected fellow. But he had a secret life. Nobody knew that he dreamt to become a feminized slaveslut, seeking an infinite and irrevocable blackmail relationship with a pitiless Mistress who would be prepared to break him with no way out. He wanted the Mistress to torment him n...