Sissy Whore Stories

50,992 results
Orientation
Length
Source
Infinite Scroll

Illicit Desires

by MistressRogueSpider on Apr 20, 2020
Transgender & Crossdressers

It was a hotel room like any other hotel, located in the cheap district. $28.99 a night could get you four walls, a "clean" bed, and a small bathroom with a tub/shower combo. The size was about the size of a studio apartment or a really small living room. Paper-thin walls meant privacy was low; you could guarantee the neighbors could hear so much as a whispe...

A Sissy and His Master's Hand

by keptsissy on Aug 8, 2018
Fetish

AUTHOR'S NOTE: No character in this story is under the legal age of consent. They are all 21 years of age or older. No sex act in this story takes place other than between two CONSENTING adults. No character in this story does anything against their will or is seriously hurt, permanently physically harmed, abused without prior consent, maimed or killed. Ever...

Letters to Michelle Ch. 01

by stevemike08066 on Oct 16, 2018
Letters & Transcripts

Dear Michelle, I hope it's ok that I email you like this, I found your email in the company database. You're a very sexy woman, and I'm not sure if you noticed me staring at you. I mean, I couldn't help it, seeing your ass in those jeans, I couldn't help it, and your breasts wrapped up in that sweater, I wouldn't mind having a couple of hours to worship...

A Downtown Moment

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the company. While I never went out with Loretta, we did have the od...

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

A Sissy Girl Bitch, 'BEST IN SHOW'

by keptsissy on Mar 3, 2020
Fetish

** Author's note: All characters depicted in this story are fictional, well beyond age-of-consent, and are consenting adults. ********************************* He made a point of showing me off, displaying me. That was obviously his thing from the start. Many men at the clubs he'd take me to were allowed to not only look but touch me too. I never thought a...

It Happened in Mexico Ch. 03

by Angelscuck on Sep 16, 2017
BDSM

Angel watched the video of her husband in disbelief. Kelly had never shown any signs that he was gay before yet hear he was, begging to suck Joaquin's cock and to be fucked in the ass and looking like a sissy drag queen. It hurt her when her husband said he didn't want her anymore and called her a whore. She felt disgusted at the sight of him being fucked,...

Doggy Style

by keptsissy on Sep 13, 2017
Fetish

I feel his middle finger slide up into my butt. He drives me crazy every time he does that. Each time is like the first time. It's the most erotic thing he does with me. It makes me hotter than when he fucks me, breeds me. I never get used to it. Every time he does this to me it's like the first time. He pushes his finger into me as far as it will go. He fe...

Sissy Cristal Used by Mistress

by mistressandpussyboy on Jan 8, 2019
Transgender & Crossdressers

This is a real life story, another day in my life with my Mistress. We were ready to go out to run some errands, when Mistress addressed me. "Plans are canceled. I want to bang a hooker: get dressed for me." No sooner said than done, I was getting naked, opening my sissy suitcase. I put on a pretty panty, black stockings, a miniskirt and my high heels. M...

Bar Table Fun

by princess_nicole on Sep 13, 2017
Transsexuals & Crossdressers

Up to Miss Kate's door i walked, then knocked on the door happily. i hadn't been to Mistress's home for a couple weeks, and was thrilled to finally be back to see Her. She opened the door and smiled at me, i smiled back and lowered my eyes. "Come in sissy", She ordered. i quickly scampered inside and set my bag on the floor. She closed the door and came ove...