Sissy Fucked Stories

161,189 results
Orientation
Length
Source
Infinite Scroll

This is What I Want

by bisissystephenie on Jan 22, 2020
Fetish

My wife Pam has started going out for a "Girls Night Out" and this time she came back a little tipsy. And very late! She knows how I love to give oral sex to her and she hardly ever says "No". We went to the bedroom and she laid back on the bed. I got in my position, on my knees and between her legs. I started kissing her knees and going up. She stopped m...

My Strapon Fantasy

by libertinaXx on Sep 19, 2017
Transsexuals & Crossdressers

I woke up in the middle of the day and smiled; my girlfriend had gone to work a few hours earlier and promised me a really good time when she got back. I ran upstairs to shower and make sure I was hairless before getting ready for her. I wandered into her room to dress for her arrival. I found a purple sheer thong and matching bra in her underwear draw that...

Megan's Bitch

by magicrub on Sep 14, 2017
Fetish

"Why are your clothes still on?" demanded Megan as she smacked her bitch across the face. "I'm sorry Mistress..." bitch replied before being sharply smacked again. "I did not give you permission to speak bitch!" replied Megan. "Besides, a Mistress does not have a cock like this one! Does she slut?" "No Mistr..err Master?" replied the bitch, starring at t...

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...

Sissy's Decline into a Slut Pt. 02

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Three: Another Exciting Night as Sissy Slut Wannabe. Well about a week has gone by since I bought the dildo, wrist cuffs, ice lock and the lubricants at the adult sex shop. Dressing up as a sissy maid or a sissy slut everyday at home and learning how to use the dildo first with my mouth and trying out the flavoured lubes for added pleasure, but most...

The 19th Hole

by skywayscribe on Sep 12, 2017
Group Sex

Sissy and Michelle were having lunch downtown Minneapolis when Michelle starting asking Sissy how Chuck was at fucking .... Sissy got wet then and there and told Michelle, "If you only knew...." Who knew that would be the beginning of a fabulous experience for Chuck ... and Michelle ... and Sissy. Michelle and Sissy continued their afternoon downtown girls...

Tales of Sub Asian Sissy Ch. 01

by subASIANsissyJADE on Apr 3, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** (I'm new here and this is my first post! I'd soooooo love to hear any feedback, questions, or comments! Many thanks, xxx, Jade) ***** I wore exactly what he demanded - he told me to dress like a regular girl... he told me he had nosy neighbors and, being a married man, he...

The Domme Club: The Fucking

by NancyPan on Sep 14, 2017
Fetish

This story will likely be most enjoyable if it is read after reading The Domme Club and one or two other stories in the series (for background of Tom and Monica's relationship and how Tom has previously been humiliated in front of the Domme Club.) Respectful comments are appreciated. ***** Mistress Monica left Tom the standard list of chores to do while s...

Black Sissy For Black Dominatrix

by Samuelx on Sep 1, 2017
Group Sex

As a Black mistress, I totally love it when my Black male Sluts dress up for me. Gleefully I slid my strap-on dildo into Reginald/Slut Gina's ass while spanking him and cussing him out like the bitch he is. The big Black dude is now wearing a frilly pink dress, red panties, stockings, and a wig, and his ugly mug is well-made up. Transforming macho Black truc...

From Her Ex-Boss to her Bitch Pt. 04

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

This story contains extreme fantasies of Fem Domme, watersports, cock sucking, forced bi, if these aspects are likely to upset you please do not read on. ***** Pete had been taken in by Rachel his ex-employee, encouraged along the way, with a little titillation, a lot of flirting and confessions of her bisexuality. She'd used her submissive Claire to help...