Diaper Gay Sissy Stories

28,999 results
Orientation
Length
Source
Infinite Scroll

His Sissy Bitch Ch. 07

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

He makes sure they all get a good look at my rear end. He pinned my skirt up in the back, large safety pin holds my skirt up at the top. It's a large baby diaper safety pin, one that women used in the 1950s, pink plastic shows at the top. Kind of cute, the pink plastic matches my ear rings. I could just take my skirt off but he says it's way sexier this way,...

Caught in a New Life Pt. 01

by Fibaro on Apr 20, 2020
Transgender & Crossdressers

(Hello everyone, this is a story that has been written for a very special reader of mine.) Intro Monroe Smith had everything pretty well figured out for himself. He was 43, his hair was brown and slightly greying, but his hairline hadn't really receded thanks to the hair implants he had done about a year back. He had never been a big guy when it came to mu...

Dominating a Man

by Tosshhh_ on Aug 21, 2019
BDSM

Even I will admit this story is a little on the unusual side but it is 100% true. I have and will always consider myself a straight man. I think even to call myself bisexual is not entirely accurate. Being a natural and experienced dominant I was well accustomed to offering my services to women who I didn't find particularly attractive. I had never considere...

My Glorious Transformation Pt. 01

by switchhitter420 on Sep 18, 2017
Transsexuals & Crossdressers

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry. ***** About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass an...

Mistress Marisa's Estate Pt. 22

by keptsissy on Sep 12, 2017
BDSM

I am one of several slaves my Mistress Marisa keeps in her household. I am completely owned as are the other slaves that serve her. These episodes are written with her permission. It is my, our story... *********** I hear the female chatter as I come down the hall from your kitchen and main bar area. I have a tray full of margaritas. As I enter the room I...

A Look Into My Mind: Uncle Sissyboy Ch. 05

by rickiee_2002 on Aug 31, 2017
Fetish

Lori and Lauren led me into the bathroom. They were giggling and talking to each other so quietly, that I could not figure out what they were saying. My wife, Serena yelled to them as they walked me to the bathroom. "Girls, I bought a liquid depilatory at the drug store. It's in my purse." "We can spread the liquid all over his body and watch the hair just...

Changes: One Spell at a Time

by Guy_Faux on Aug 31, 2017
Fetish

Author's note: This story involves themes of incest, mind-control, the abuse of magic, and transgender. If these don't appeal to you then don't read it. Otherwise please enjoy. * I was still young when I lost my virginity. She was older than me, a high school girl in fact, but she was so impressed by how large my dick was that she gave me a shot. I imagin...

Sissy Keven Jeanne Bardot

by nancyvasquez on Sep 14, 2017
Erotic Couplings

After Jinky and I had been married about a year, she began to make gay references about me being gay. When I'd get mad, she'd laugh and say, "I'm only joking!" I remember she always used to squeeze my breasts, which were quite prominent, and say, "Wow, sweetie, nice development!" And then she'd laugh. My feminine breasts had been a source of embarrassment f...

The Roommate Test Ch. 02

by PetRopeBunny on Apr 13, 2020
BDSM

Last night was amazing. When I woke up the next morning, I was still floating on cloud nine. I was looking for a new place to live, my best friend from work was looking for a new roommate and yesterday started our weekend sleepover to see if we were compatible living together. It started as a slumber party and ended up with me being restrained to her bed and...

Mistress Emma's Revenge

by sissymissyct on Oct 15, 2017
Fetish

Hi I'm Ken. Well I was, now I'm called Brenda. Here's a bit of my story for you. I hope you don't make the same mistakes I did. Because until I got caught misbehaving by my mistress, life was pretty good. At 38, I had a great job as an office manager in charge of 25 or so employees, mostly women, a really good salary, a nice office and plenty of job securit...