Sissy Strapon Stories

8,068 results
Orientation
Length
Source
Infinite Scroll

Sissy Whore Pays the Rent

by FrillyMaid on Sep 15, 2017
Transsexuals & Crossdressers

I walked in from the rain, and was confused by the silence. Normally my Mistress would be sitting in the living room with a glass of red wine and her favourite show on, but instead the room was empty and silent. I walked to the kitchen and saw a note on the worktop. It said simply "wear the clothes in the bathroom and come upstairs". Walking to the bathroom...

Sam's Story Pt. 09

by Shadykingcolor on Jul 6, 2020
Fetish

As I sat in the basement...the dungeon, contemplating my new life as "Trisha." Mel's anger. She knows about Cassie. How my life is forever changed, I ask myself "was it worth it?" The door creaks open. Someone begins to descend down the stairs. It's Cassie, holding a cup and saucer. "Tut tut tut, Pet. Who's been a naughty little sissyboi." She purrs while...

Training Him to Take Dick Ch. 01

by magic_tantra on Sep 19, 2017
Fetish

Training My Stud Boyfriend to Take Dick! Ch. 01 My name is Belinda I am a college coed who loves sex with both girls and guys. I am a hot brunette with long black hair down to my butt crack with ivory white skin and piercing blue eyes. I have a nice shapely body and love my real 36 C breasts with strawberry sized nipples. I have a clitoris that protrudes fr...

How I Met My Wife

by Godscountry on Sep 13, 2017
Transsexuals & Crossdressers

When they ask, I tell people that I met my wife on the internet. I'm sure they assume it was on a dating site. But the full story is much more interesting, how she came to own me and how I came to worship her as my wife. I'd been single off-and-on for a long time. 28 years old. I had a decent job in engineering. I've had a few good girl friends, but nothin...

The Huntress is Also a Mistress

by Dazzle1 on Jan 16, 2019
BDSM

"Are you sure this makes sense, Jack?" "What are you worrying about, Tristan?" His large muscular friend asked. "We are in the middle of nowhere," Tristan who was much smaller but still in good shape. "We could have hit 3 houses in town, instead of hoping there is stuff here." "Ya, but this rich bitch should have a lot of stuff here. And no cops." The li...

How I Became A Cross Dresser

by dirtyjoe69 on Sep 16, 2017
Transsexuals & Crossdressers

Hi my name is Ted and one of the most embarrassing days of my life became a day that I will cherish forever. It opened my eyes to a whole new world for me and my wife. I am a totally straight man that has been married to my loving wife for over ten years and let me tell you I was as surprised as anyone would be by what happened. The day started out like any...

A Model for CC's

by Fibaro on Oct 5, 2020
Transgender & Crossdressers

(This story was requested by one of my readers. This is a stand alone story, but reading "Neighbourhood Terror to Sissy" first is advised as this story takes place in the same universe.) Intro Victor was just a regular guy down on his luck. A month ago he still had it all, a beautiful girlfriend, a nice apartment and a decent paying job working for an acco...

X-Change

by Noah_Peal on May 15, 2015
Miscellaneous

Pills Pink pills change males to females. Blue pills change females to males. Purple pills (X-Trans) change males or females into transgenders, can be combined with pink or blue. X-Change (Formula subject to change) Acquired from unlicensed "street" vendors. Changed (defective/in testing) formula. Cheapest. High pregnancy risk. Can lead to mental a...

Open in Reader

A Toy Party Story

by lushusboobs on Sep 11, 2017
Transsexuals & Crossdressers

Toy Party Story Recently I met with a person whose sole desire was to be fully dressed and transformed for me. We spent quite a bit of time on the phone discussing why feminization was such a powerful fantasy for him. He explained that he felt so vulnerable and powerless as a woman and that it was exactly the opposite of his everyday life where he held mu...

You're My Bitch Now Ch. 10

by nikkiesilk on Dec 31, 2018
Transgender & Crossdressers

Rick had closed his eyes as he began to lick the girl's toes, but he opened them again as he felt a tug on the collar. Looking up he saw Rhona had passed the lead to the Asian girl who was pulling him towards her, She had spread her legs wide and he could see her pussy glistening in front of his eyes. She wrapped the lead around her fist and pulled his head...