Sissy Hair Stories

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Orientation
Length
Source
Infinite Scroll

Mr Derrek

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

The room is filled with the sounds of sex emanating from the wide screen tv. On screen a sylph of a gurl is on display all fours on a small low table surrounded by a sea of men in various stages of undress. The slim smooth skinned gurl is dressed in a short flared skirt that frames her sweet ass beautifully in layers of ruffles and lace with her pretty match...

Prankster Ch. 10

by Paris Waterman on Sep 15, 2017
Group Sex

Copyright © 2007 Many thanks to "Techsan" for graciously giving his time and effort to me in editing this and other stories of mine in recent months. As always, I appreciate your excellent support, thanks again, Techsan. Chapter 10 After letting the girls out of the van and escorting them into the warehouse, Tony made a couple of calls to old acquaintan...

Sissy Slave Fantasy

by tinkerslut on Sep 13, 2017
Transsexuals & Crossdressers

A fantasy written to my mistress.. Sissy kneels before you, her eyes down, waiting on your pleasure. Sissy is wearing frilly panties with a matching bra, thigh high black lace stockings encase my legs. The red dress barely covers her smooth bottom. The high heel shoes, locked on my ankles, crossed behind me. I can't speak because of the ball gag in my mouth...

Straight Guy Gets Some "Strange"

by nancyvasquez on Oct 15, 2017
Interracial Love

The Negro saw the bright lights across the street advertising the adult bookstore. He felt a stirring in his groin and he pushed down on his cock. He could use a jerk off session, he hadn't cum in a few days. It was a very warm night, and the rain had stopped, leaving the smell of wet asphalt in the air He went to the counter. "How much to go in the back?"...

Sissy Crissi Ch. 03

by sissycrissi on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 3 -- Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upwa...

Ultimate Sissy Weekend Ch. 03

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Before today, Susie had only ever spanked herself. Nothing could have prepared her for the 220 spanks she'd received earlier, her first serious sissy spanking. Still her butt burns, even in its new pink poofy diaper. And now it's joined by fresh welts and lines on her inner thighs from the cruel canings of the redhead's ruler, as she happily decorates the tw...

Panty Posers Ch. 06

by EROTICbearscribe on Oct 19, 2020
Transgender & Crossdressers

We entered our building and bumped into our downstairs neighbor Jerry. He was taking his trashcan back to his apartment. He set it down at the landing and gave us each a good look. He wasn't at all phased by our appearances. "Little early for Halloween, isn't it...boys?" he asked. We both were fully aware Jerry knew we were sissies. It was fairly obvious...

The Vacation from Hell Pt. 01

by JamesMiehoff on Nov 27, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

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...

Turned So Totally

by gbr2004 on Oct 8, 2019
BDSM

It was our first actual meeting. We had emailed back and forth about what we were both looking for and found we had similar interests. He wanted to take a straight acting guy, take his masculinity away and turn him into his submissive sissy bitch. That is what I had been thinking and fantasizing about continually but could I actually do it? From our email ex...