Crossdressing Chastity Stories

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Sweet Treat

by SaucyMasquerade on Sep 14, 2017
Transsexuals & Crossdressers

I As the water streamed across the window pane, I watched Jayne pull her coat tight, dashing from the car, through the torrential rain into the house, cursing the British summer in all its soaking glory. "Steve," she called, as she hung up the coat to dry, "I've an invite here, to a fancy dress party, Helen is holding on Friday" "I'm in here," I called...

Work Day, Fun Day

by manatdawnrise on Mar 28, 2018
Transsexuals & Crossdressers

Showering for work, I look down at my chastity bound cock, still struggling to come to terms with the events of the weekend. A sense of relief washes over me. The relief found when a lifelong secret had been broken. I was no longer wracked with guilt of my crossdressing dark side. No, I was now liberated in mind yet bound in a physical sense. My wife had a p...

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...

What Craigslist Got Me!

by SissySlutPrincess on Oct 13, 2017
Transsexuals & Crossdressers

I had been crossdressing and playing by myself for years. A simple fun way to pleasure myself and satisfy my love for all things girly. I just needed more being from a small Ohio town made it tough to actually find someone to share this leisure with. Everyone knew everyone so no one wanted to get caught, but me! I decided to check out Craigslist. I posted a...

Lace and Love Ch. 01

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Daniel Sohn let out a sigh of relief as he finally finished met his deadline for a computer company who had hired him to write a program for them. The twenty five year old Asian man was an expert at programming and software design and was hired regularly by various corporations to write code for them. He was so good he could do it all from his home which he...

Crossdressing Confessions Ch. 04

by EvelynWilde on May 13, 2020
Transgender & Crossdressers

I roll over, back under my sheets right after I read her promissory message. I changed back into boxers in a fit of shame after coming home last night. Still the thrill of that night lingers like a lead weight on my chest, making my breathing shallow and constricted. The sensation resurrects the memory of her hand holding me down against the mattress, the sh...

Just Look at Me Now Ch. 05

by GFfan on Sep 14, 2020
Transgender & Crossdressers

ACT ONE: PARTY PREP "If the item is defective, you can return it for a full refund, but no, you cannot return it if it's simply too big. I'm sure you can understand why." This was the saleswoman's reply to the question I had been instructed to ask about an item Jude and Becky had assigned me to buy. "I doubt that will be a problem though," the clerk, Felic...

A Fantasy with Lisa

by chastityfan on Sep 13, 2017
Fetish

I met Lisa for the first time just after finishing a workout at the local gym. Over the next few weeks we ran into each other on a regular basis and ended up going to out for a few pints. Spending time together eventually put us in bed together and we decided out relationship was best left as a friends with benefits situation. Over time we discussed each oth...

Where did My Damn Key Go Pt. 03

by PascalSage on Sep 24, 2019
BDSM

Four days; I've dealt with four grueling days of not being able to touch myself. Jesus, how can anyone even do this with out even going insane?! Ever since I crossed paths with that dominating bimbo, my entire routine had changed. And to be honest, I was surprised at how much sex was in my life. From the moment I woke up to the second I crashed and fell asle...

Life and Time of Lady Vargos Ch. 18

by rik581 on May 21, 2019
Transgender & Crossdressers

Chapter 18 "Changes upon Changes" Martin rolled over on his side hugging his pillow trying desperately to fall asleep. Though the curlers that Leanne had tightly wound in his hair for the night were very uncomfortable and trying to position his head to sleep in them was exhausting, it was the events of the day weighed heavily on his mind and kept him awake...