Crossdressers Chastity Stories

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Allie's Encounter on Craigslist

by allycd on Sep 13, 2017
Transsexuals & Crossdressers

Let me start off by saying this is a 100% true story. I know there's some that will try and pretend to be real but are in fact not. There's no real way for me to prove it, but nonetheless I just wanted to share my experience. About a week ago I posted an ad on craigslist "19 y/o Asian CD looking for a dominant top", asking for their pictures and stats. Aft...

Her Male Wife

by Zippeduptight on Nov 6, 2018
Transgender & Crossdressers

Sometimes I wonder how I got into this mess. The answer is obvious but it usually comes during the day when I pee. Carla's orders are to sit when I pee. I lift up my skirt, and tuck the exposed chastity device down, and relieve myself. Just like now. The shiny pink pvc sissy maid outfit she bought for me is locked on at the neck. I stand up and flush walking...

Forgiving Wife Pt. 02

by manatdawnrise on Jan 14, 2018
Transsexuals & Crossdressers

"Tonight just got more interesting" I said. "Oh, you don't even know the half of it yet," she beamed. Taking her drink to her lips like nothing had happened. Urges pulsed through me yet I couldn't do a thing here. Putting it simply, I needed to get her home, I needed her, my restricted erection felt unusual yet pleasurable . Finishing our drinks, we left...

First Time for Daddy's Girl

by JennaJay919 on Dec 17, 2018
Transgender & Crossdressers

I had been talking to him for a while now. This man. Daddy. Somehow the constant barrage of pornographic images and sissy hypnosis had taken a hold of me and brought me to the point where I had actually begun to develop a relationship with a man. I had never thought of myself as gay, or had thoughts about men. I was the typical A-student, moderately athleti...

A Sissy Fantasy

by Sissy_Jeanette on Mar 30, 2020
Transgender & Crossdressers

My darkest fantasy has come true. I'm now a slave to a dominant couple. My ex-wife and her new boyfriend have taken me in, and in return I am dressed as a girl always and their maid and sex slave. Frilly panties, stockings and skirts, babydoll t-shirts, and a blonde wig are parts of my new uniform. Also I now wear a stainless steel chastity cage now encasing...

Simon's Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

Simon’s Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

The Roommate Pt. 12 - Miranda

by ValoryG on Sep 19, 2017
Transsexuals & Crossdressers

Chastened, Josh/Lori nursed her wounds for days, and little was said between her and Miranda, except when the dominant asked how Lori had opened her chastity when with Cassie. "I bought a master key on the Internet," answered Lori brightly. "Actually, my penis is getting a little irritated by the plastic over such a long time." "Give me the key. It obvious...

Sissy, Hypnotized

by Slipperylock on Apr 8, 2019
Transgender & Crossdressers

It had taken six months to get to this point. As I stepped out of the bathroom, I caught sight of myself in the full-length mirror, and shivered. I was shaved below the eyebrows, hairless and smooth, except for a cute landing strip above my locked chastity cage. Other than the cage, I looked like a thoroughly average 21 year old boy, my small and skinny fram...

Lock Your Phone

by Iamasissy on Sep 15, 2017
Transsexuals & Crossdressers

I am a sissy and I love it like most sissies I dream about belonging to a man to be owned by him. I fantasize about being outed and being forced to become a transsexual. I put out adds on craigslist NY looking for a Master. I take lots of pictures dressed, I take videos dressed saying my name is Karen I am a sissy and I want to become a transsexual for a rea...