Diaper Gay Sissy Stories

28,999 results
Orientation
Length
Source
Infinite Scroll

Shattered

by kayla_femboi on Sep 16, 2017
Transsexuals & Crossdressers

The following story is mostly true. I changed the names for the sake of privacy and maybe spiced up the details a bit. A little background about me: my name is Brian, although when dressed i feminize me name to Brianna. I was a closet crossdressing sissy. I had always been effeminate growing up and a bit confused sexually. I never really dated girls. Inst...

Uncovering the Sissy Beneath Pt. 06

by jefferyscott745 on Jul 31, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part five of my previous work. Be sure to read parts 1-5 if you wish to understand the background of this section. Sherry and I sat on the couch for a while watching fashion shows again. There was no discussion about what had just ha...

The Marriage

by zeta515 on Sep 17, 2017
Fetish

Acknowledgements: My very grateful thanks to AngelLove for agreeing to edit this story, for her very timely work, and her valuable suggestions and corrections. Copyright 2006 by Zeta. All rights reserved. Rose turned and looked at the red numbers on the clock: six-seventeen a.m. The bedroom was beginning to lighten as the sun rose, heralding the new day a...

Butch's Bar Slut

by sissymissyct on Jan 7, 2020
BDSM

(A bit darker than most of my tales. It would fit in gay or nonconsent as well. Gay sex, sissy sex, chastity and punishment.) *** I love this bar, Butch thought to himself as he finished another beer. And why shouldn't he. It had everything a Leather Bear could want. Plenty of hot men in leather, and some women as well. A bunch of trans girls and some siss...

Stevie's Journey

by gbr2004 on Oct 7, 2019
Fetish

I remember being so excited landing a position as a legal assistant at such a good law firm. My boss Mike Maddox seemed to be a great guy and I was looking forward to learning from him. I never imagined what it would be that I would learn from him. This job has changed so much and I can't even decide if I regret what has happened or if it was where my life w...

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...

Stevie's Journey Ch. 02

by gbr2004 on Oct 7, 2019
Fetish

I sleep soundly but finally wake up and realize it's almost nine o'clock. I get up and take a shower. The hot water feels so good. I get dried off and go over to the dresser and open the top drawer and there are several pairs of panties in the drawer. I pick out a red pair and slip them up my legs. They feel so soft as I pull them up. I reach in and tuck my...

The Visitor Ch. 08

by Leanne_sissy on Sep 26, 2017
Transsexuals & Crossdressers

This is a continued story of my experience with an online master that became a reality. ***** He knelt in front of me pulling me closer to him as I whimpered through fresh tears, my fight seemingly gone out of me. Why oh why didn't I just kick him away then, why didn't I push him over, run out of the door, run, hide. I couldn't call the police, I knew I co...

Re-tooled

by Sissyhalo on Mar 13, 2018
Transsexuals & Crossdressers

Re-tool your life. Re-tool yourself. Sick of not getting what you should? Sick to fucking hell of all these assholes getting with hot people they really don't deserve? Sick to hell of Liberals and Feminists making impossible to jump through hoops so that only the privileged people get to be happy? Sick of being a goddamned incel? Look we all know that...

Danni

by Coder3445 on Jan 6, 2020
Transgender & Crossdressers

This story is a complete work of fiction. In said work all characters are at least 18 years if age. This is my first story so constructive criticism is welcomed. Enjoy or not don't let me tell you what to do. *** Daniel had an issue, the issue being that when he had first started watching porn he like any other cis-gendered male had started with a voluptu...