Crossdressing Punishment Stories

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Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

Becoming a Sissy Maid & Slut Vol. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Title: How I became a Sissy Maid and Slut for a Dominant Master. Preface: I would like to begin by thanking all who will read my story here. This is a sissy story based on many thoughts I have imagined, many times throughout my life. These erotic thoughts have been enjoyed for a long while in my life. Like many sissy girls, stories like the one I will wri...

The Holiday Pt. 01

by mandiejune on May 16, 2018
Transsexuals & Crossdressers

My name use to be Frank its now Helen sissyslut and I was surfing web looking at crossdressing sites on my computer when this holiday competition came up. For some reason may be my wife had left me after finding me dressed up like a hooker! I decided to enter the competition not really expecting to winner a free 4 weeks holiday in South of France. Two weeks...

An Intimate Caning?

by deference on Nov 26, 2017
BDSM

An oxymoron is said to exist when two words are used whose meaning does not seem to fit together such as jumbo shrimp or government intelligence. No doubt, the words 'intimate caning' would also fit this definition. However, while a majority would view corporal punishment and domestic discipline as either sadistic or sexually deviant, a minority have found i...

Be My Bitch

by purekink on Aug 20, 2019
Transgender & Crossdressers

I'm so glad you agreed to be my slut – I've been searching for a crossdressing hussy I can train to be my personal tart for some time now, and I'm certain I can teach you to fit the bill. I understand your fantasy is to be dressed as a sexy sissy and have your manhood and your cherry fucked right out of you. This pleases me, as I enjoy nothing better than u...

Abigail's Slave Ch. 02

by randomer555 on Sep 25, 2017
BDSM

Joe laid on the bed, waiting. Abigail had been gone for a couple of minutes now and the suspense was killing him. Just then, he heard Abigail and whoever had just arrived talking. Joe recognized the voice as Abigail's friend Jackie. He wasn't very surprised that Jackie was dominant; when Joe saw her, she had been very domineering towards her boyfriend. Abig...

Forced Crossdressing Stories

by Dayeandknight on Feb 1, 2018
Transsexual

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't yo...

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Lydia Ch. 04

by femmed on Sep 13, 2017
BDSM

Note: Part 4 is short, but it came to a natural stopping point. I am working on part five. * With that, Jen walked me back over to the side of the bed and had me kneel down. She tied one hand to each bedpost, then sat lightly behind me. Even through her jeans, I could feel the warmth of her ass against the back of my knees. "I know, this isn't exactly wha...

From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

Integration Ch. 01: Discovery

by takingitupthechutney on Apr 21, 2020
BDSM

Gavin grabbed a wet wipe. He went to pass it to Donna, but at the last second decided to wipe her crotch for her. "Thanks," she said with a grin on her face. "No one wants to lie in a wet patch after sex. Well I mean some people are probably into that, but that really doesn't do it for me. Either way it helps keep the sheets clean." Gavin giggled. "So what...