Sissy Bondage Stories

20,137 results
Orientation
Length
Source
Infinite Scroll

Young Crossdress, Meets His Daddy

by Sliver02 on Sep 1, 2017
Transsexuals & Crossdressers

Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very open marriage, but there are few things she does still not k...

Smoking Blues

by sissymissyct on Mar 26, 2019
BDSM

"Hey Bren," called my assistant Sarah. The home office called while you were out smoking. You Better call Mr. C back. He didn't sound happy!" "Okay, thanks dear. I will call him back straight away," I replied as I headed to my office. As I was opening my door Sarah continued. "You know, you really have been taking a lot of smoke breaks lately. We are all co...

A Sissy's Forced Gangbang Pt. 02

by sissy77 on Dec 8, 2017
Transsexuals & Crossdressers

This story is a continuation of the part one of the series under the same title. If you haven't read part 1 already, I highly recommend you do so before reading this part. ***** After snapping out of harsh daddy's words and contemplating what more humiliation was planned out for me, I lifted my head off the bed and was welcomed to the sight of big daddy's...

Starlit Petal Ch. 01

by Certeis on Mar 21, 2018
Transsexuals & Crossdressers

NOTE: this story is an original setting, but anything you need to know is discussed in the story text. *** 'Swshh' 'swshh' 'swshh' Petal's legs moved back and forth rhythmically, the nylon stockings rubbing against each other at every pass. They were dangling in the air above him as he laid on the padded bench and read a book. Well, pretended to read it, a...

Making Francesca Ch. 05

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

It seems that I finally have gotten the time to finish posting this story. If you have not read the first four chapters, I highly recommend it as the story will make much more sense. Enjoy. As he sat there on the thin mattress, pondering his new outlook on life, Justin appeared with his supper. Justin opened the door to the cell and placed a folding chai...

Internet Meeting

by Stillherer on Sep 16, 2017
Fetish

We met on the net. How modern. He was shy and nervous, very much like I was though if anything even more cautious. Being a closet cross dresser with a life outside my apartment door my main aim was discretion and major fear -- discovery. Charles appeared to be perfect for my yearning to fulfill my fantasies and spice up my solo adventures. We chatted online...

Behavior Modification Institute Ch. 09

by NancyPan on Sep 12, 2017
Fetish

I want to finish the story since I have some avid readers and I don't want to leave you "hanging," so to speak. However, I've noted a significant drop in the number of votes and the rating of the last couple chapters - so if you want to encourage me or have constructive suggestions, please vote and/or leave a comment. ***** Confined to the cage and in tot...

A Weekend Away Ch. 02

by SluttyChrissy on Sep 14, 2020
Transgender & Crossdressers

Author's Note: Thanks for all the kind feedback & comments on chapter 01. This chapter does a lot to set up the rest of the story, so there isn't a ton of sex. Please hang in there with me and there will be much more sex in the chapters 3-?? I hope this one is sexy enough to keep you interested! ---------------------------------------- I'm not sure how lon...

To the Manor Bound Ch. 02

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This is part two of a series; you'll probably need to read part one to get a grip on what's going on. As with the first part this focuses on forced feminisation including aspects of BDSM and non-con, so if that's not your thing, now would be the time to leave. Chapter 2 -- The Next Day Peter was barely able to find a second's worth of sleep that first nigh...

Pat's Panty Slave Ch. 01

by Sissyfreak on Sep 12, 2017
Transsexuals & Crossdressers

This is a fantasy story of mine. I am a 35 year old man with a wife and 2 kids who, for some reason or other, feels the need to dress up once in a while, in my wife's sexy underwear. Whilst "dressed up" I tend to fantasise about numerous things, one of which I will share now. It starts with me returning home one day after dropping my wife and the children...