Crossdressing Punishment Stories

32,309 results
Orientation
Length
Source
Infinite Scroll

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...

Forbidden Codex

by TheCanadian on Aug 30, 2018
BDSM

You’ve got a freind named Denise, with a strong interest in the supernatural--something you have in common. At times, it seems she has a crush on you, but you’ve been friends for years. Besides, Denise was just older than you by enough that you figured she didn’t think of you that way. One afternoon, you knocked on Denise’s front door. When the door opened,...

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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...

My Sexual Fantasies

by Submissive Timmy on Sep 16, 2017
Letters & Transcripts

My Sexual Fantasies (OD Repost) I wrote this in November 2002 for my online journal on Open Diary. I'm posting this simply to have something posted. I do intend to actually write eventually. ***** I have a penis. Isn't that amazing? I also have two testicles. The flu had a stranglehold on them and killed my sex drive. But, I've since driven the flu off wi...

Guildmates Ch. 02

by TGDIB on Jun 15, 2020
Transgender & Crossdressers

(What is this, a crossover episode? Sorry for the delay and any lacking quality, been super busy. Thanks everyone for reading After the compelling argument Damon had made the night prior, Asa decided to indulge him and give things a shot. At the very least, the sizeable sum he had been provided was enough to keep him going for a while. He called into work,...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...