Crossdressing Aunt Stories

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Disgraced Fiancee

by rik581 on Sep 16, 2017
Transsexuals & Crossdressers

"OMG, Laura please, don't make me do this," Dave pleaded one last time as it was now time to stand before her entire family and beg their forgiveness for his sexual indiscretions. She straightened the dress he was wearing, then adjusted his earrings. "No Dave, the talk is now over. You will perform this embarrassing act for me, and ask my family to forgive...

Girlboy Diary Day 01

by Hartford on Sep 16, 2017
Transsexuals & Crossdressers

Day 1 It might never have happened if my aunt hadn't caught me wearing girl clothes at the mall, clothes plus a wig and make up. How she knew it was me is a mystery because I can pass like nobody's business. Hate to brag but it's a fact. Anyway, my aunt followed me, got some still photos and video on her blackberry, and showed it to Mother. I found out six...

[The misadventures of K-T]

by TheDespaxas on Apr 22, 2025

foreword This is a transfer and continuation of my "what if katie was a boy named K-T instead?" branch on the awesome story https://chyoa.com/story/The-Humiliation-of-Katie.10376 since this part of the story flips around and has a boy being stuck naked, bottomless and in various embarrassing or exposing situation, I decided to make it a standalone...

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AlabamaNan: Me, Myself and....OH MY

by AlabamaNan on Sep 14, 2017
Transsexuals & Crossdressers

This tale of voyeurism and self-satisfaction happened really early during the days of my transformation from Nathan to Nancy. I had bit the bullet and gone home to my unaccepting family in Alabama for a summer. The stay was made bearable by the fact that my sister Karen was 'renting' the empty trailer on my mom's property and had 'her own place'. Upon arri...

Grab Bag Transvestite Story

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

I am a part time transvestite, who, if I do say so myself, looks quite attractive when dressed as a woman. It has taken me years to become adept at makeup and being capable of selecting sexy clothing that is in my size and that suits me. I have also had a number of lovely encounters with other TVs and male admirers. You can read my True Stories on this site....

The Marriage of Martin Hastings Ch. 17

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Martin sat alone in a small interrogation room. The large wood table with the two empty chairs on the opposite side of the table were all the furnishings in the room. The humiliation Martin had suffered as he was brought through the police station, the giggles, sneers and staring were still fresh in his mind. Though he was told he was not under arrest, he fe...

Agnes Dourville Ch. 18

by ValoryG on Dec 22, 2017
Transsexuals & Crossdressers

I am lucky, very lucky. Sometimes I think I have a little guardian angel sitting on my shoulder (on my bra strap) leading my life down lucky lanes that ultimately lead to good things - good things I really don't deserve. I'm going to skip through a lot of time now. It's time to draw my story of a young lad, or young lady, to a close. Both Sharon and I att...

Sissy Maid to Be... Ch. 03

by missjennymaid on Apr 8, 2019
Transgender & Crossdressers

I would recommend reading the first chapters to get to up to speed on the story, but if you want to start in the middle... Jeremy: A married crossdresser who loves to live out his crossdressing fantasies with his supportive wife. Lizzy: Jeremy's wife who participates in his sissy maid desires every other Friday when they have the place to themselves. Jere...

The Bio of a Masturbator

by Chatomana on Sep 18, 2017
Toys & Masturbation

Disclaimer: Although this is a work of fiction, some parts contain actual facts and events. The author can not and will not be held responsible for any injuries that may occur if the reader tries to reproduce of these events. The author holds all copyrights to this story, printed and/or digital. Prologue This story is not about love, nor about romance, or...

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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