Crossdressing Punishment Stories

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Master's Degree in Crossdressing Ch. 02

by wifetoy on Sep 16, 2017
Transsexuals & Crossdressers

This confession is the second chapter of a follow up series to my earlier series "College Crossdressing Confessions." My wife forced me to make those confessions detailing my shameful addiction to wearing panties, pantyhose, and other girly intimates, and my panty pilfering ways in college. While I was making those confessions to the public for the first tim...

My Secret Revealed Ch. 02

by jealouscuck on Mar 14, 2018
Transsexuals & Crossdressers

My wife had accidentally found panties in my travel bag. Even though she was not trying to discover anything hidden in my bags, the deed was done. I explained the beginning of my panty fetish. (Chapter 1). What she objected to was my keeping part of my sexual preferences a secret. The trouble came from trust issues. After a trip out of town and us finally be...

The Transition Ch. 01

by Quantarx on Jun 8, 2020
Transgender & Crossdressers

Greetings and thank you so much for choosing to read my story. This is intended to be a multi part series so bare with me as I try to develop the characters and lay down the backstories. As always, Your feedback is always essential in the development of the story going forward. Please leave a comment down below * I Had been Married for about eight years w...

Ugly Duckling to Sissy Princess Ch. 02

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

(Continued from Part 1) My girlfriend, Carol, and I made love to each other about 2 times per week. She was also getting fucked on a regular basis by her jock fuck buddies. I never asked how many guys she was hooking up with on the side, but, I guessed it was at least five, because there were five jocks that she tutored on a daily basis. She put on skimpy c...

Several Stories from Somewhere Else

by Freyasbearn on Mar 11, 2018
Fantasy

This is the landing page that will take you to the several stories re-archiving here. I am also using this section for new stories with the same themes as my other stories. That way I don't have twenty different stories all over the place that cover the same stuff. You can get it here. If you want to add on, or take a story a different way-- please, please d...

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Fulfilling all My Fantasies Ch. 01

by classmate1119 on Apr 23, 2019
Transgender & Crossdressers

"Last chance to change your mind, Cristi," Jalen said. "It's probably the most outrageous one so far! Not that I'm worried, of course, but you never know what else might happen... " I reapplied my lipstick in the reflection of the club's glass entrance. "Hey, we spent too much time preparing for this. Don't back out on me now, Jalen!" I threw him a coy smi...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

Encounters of a Crossdressing Slut

by KAshton on Sep 16, 2017
Transsexuals & Crossdressers

This is an introduction to my crossdressing experiences, touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever. I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like sli...

Trapslut

by Alexia Wright on Aug 20, 2015
Fetish

Today is the day. Your erotic crossdressing blog videos have earned you your first practical job as an escort. Being the famous online sissy slut Annie, you used to pay the bills selling your horny pictures and masturbation videos to guys on the Internet. You got out of bed, still in your pink babydoll nightie complete with a baby blue thong and head for the...

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Your Waitresses

by weluvhose on Sep 15, 2017
Transsexuals & Crossdressers

We have not submitted anything for almost a year as daily life as certainly been in the way for ALL of us. My wife and I decided this one would be a slight change to the previous submissions. It is all fantasy but we both would enjoy bringing this one to "true" life if ever possible. Enjoy and we always welcome any comments!...