Sissy Fucked Stories

161,189 results
Orientation
Length
Source
Infinite Scroll

Sissy Chantel, New Reality Ch. 02

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Two: If One was Fun, Two will be Better. Late night I get a call and I look to see that it is my new Master. I answer, "Hello Master Camron, how may I help you?" "Bitch ass sissy, I am gonna need you here tomorrow morning, by 10:00am." he excitedly replies. I reply, "Oh, ok I guess I can make it to your home tomorrow morning Master." "You God Dam...

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

Me & My Wife Are Sisters Now Ch. 02

by gayindia1980 on Sep 16, 2017
Transsexuals & Crossdressers

This story is in continuation of my last story Me & My Wife Are Sisters Now Ch. 01 ***** Next morning, we both slept quite late then our usual time, I don't know about Shivika but I was still feeling cum inside my ass. Last night my wife, Shivika was fucked by 2 sexy men in a 3some and then one of them fucked me really hard. Shivika woke up around 9:30 an...

Caught in Panties & Dominated Ch. 04

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

Cast Tracy -- me Tracey -- me, dressed en Femme Rick - head of security at work, had just caught me masturbating at work, dressed as a woman Ken - my roommate My ass was so sore. But he hadn't fucked me. Not yet... Earlier that night Rick made me his bitch. He took my sissy, lipstick-painted mouth, with his cock. He'd commanded my mouth, and he'd fill...

Steve to Stevie to ?? Ch. 07

by gbr2004 on Sep 13, 2017
Fetish

I had returned to work after my first nite with Ms Storm. The night she turned me from a young man to her slave. Ms Storm had came to my work place and had talked to my boss for a long time but I don't know what she told her but my boss, Ms Hunter, had talked to me like never before. Then I had been ordered to return to Ms Storm's house that night. Upon arri...

Miss Guided Pt. 03

by MissMarianne on Apr 9, 2019
Transgender & Crossdressers

That evening I went to dinner at Donna's house. Donna opened the door and was beautiful in her little black dress. She wore impeccable makeup, stiletto heels, black nylons. I felt like a frump in my plain outfit. She explained that her husband Mary Lou just got home from work and was upstairs changing. We talked and drank daiquiris for about a half hour...

Subliminal Obsessions Ch. 03

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

*Before... She shows me our profits and stuff...and stuff meaning gifts with cash transfers and e-notes sent for who. I'm floored, literally floored I've never had this much money in my life. I'm not rich but holy fuck...I can...I just sit and stare and look at the screen. "What are you going to buy first Nikki?" "Bills, bills and some savings but the r...

Black Cock Smoking Sissy Slut

by Lisa_Fuckslut on Sep 14, 2017
Transsexuals & Crossdressers

I left the club early. No luck tonight in getting my ass laid. Where were all those hot young studs with their big swinging penises and cum-filled balls when you need them? I had dressed in my sluttiest gear. 6 inch 'fuck me' heels, fishnet stockings and a tight little leather dress. Heavy makeup. Long, thick false lashes to flutter at the boys. Long, sexy,...

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...

Dreams

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

"Hey! Hey! Wake up, wake up!" "What? Jo, what is it? What's going on?" "I think you should be telling me that!" "I don't understand." I was slowly coming round now, But I was still mystified as to why my wife had woken me at 2 a.m on a Saturday morning. "Erm your cock is as hard as nails and you were waving your ass in the air," Jo said, starting to laug...