Crossdresser Chastity Stories

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Sarah Meets a Buddy

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I posted a listing on Craig's List for a "cum buddy". I explained that I am a crossdresser and that I wanted to find a regular sex buddy. No commitment, just sex. I love to get on my knees to give a blow job. I had several replies. One was local and sounded promising. I don't rush into meeting with a total stranger. First I always exchange a few emails and m...

Parking Area 2 Miles

by Lovinhose on Sep 15, 2017
Transsexuals & Crossdressers

Prior to writing this next installment in my awesome sex life as a bisexual crossdresser, I thought I had already written about all of my worth while, true life experiences, but I had actually forgotten about this one. It happened in, I believe, 2008, during the end of the summer. I was driving my truck. I am a truck driver by trade. Three hours and a co...

Crossdresser Crosses Over for Good

by TVTrishCD on Jun 8, 2020
Transgender & Crossdressers

I certainly allowed myself be conned! So, I had a problem with my turn signals on my car back in early January. I was pretty sure it was the turn signal switch, but not sure. There is a site where sex ads are very prevalent. In the CD section it's mostly hispanic, and oh do the latino boys just LOVE us white cd's!! They are very relentless in their pursuit o...

Lucy's Revenge Ch. 06

by Cynthia_D on Sep 18, 2017
Transsexuals & Crossdressers

Final Chapter It was Friday night after a very long week of being humiliated. I had a couple of cocktails to calm down after my latest forced outdoor adventure - being exposed to numerous people while crossdressed. The phone had rung and I made the mistake of answering it thinking it was my wife who was due home that weekend. But the caller wasn't my wife i...

Sleeping Beauties Ch. 07

by MicheleNylons on Dec 16, 2019
Transgender & Crossdressers

Chapter Seven -- Heads or Tales Penelope, Silvia and Bradley arrived at Ellen Wright's house to find the scene of crime team and medical examiner in attendance. They put on the Tyvek over-boots, hair coverings and latex gloves and entered the house being careful to tread only on the matting laid down by the CSI techs. Bob Tanner met them at the door to the...

My Wife, My Tormentor

by Sissyjackie2008 on Sep 16, 2017
Transsexuals & Crossdressers

I am excited by the . One of the most humiliating experiences I sufferer was caused by my first wife. I had been a crossdresser since I was little. Actually my mother started me when she dressed me as a girl for Halloween. When at 7 I started to protest, She said she had no daughter and once a year I could let her have fun. I could never refuse her so I re...

Sarah's First Time Out Dressed as a Girl

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

During my collage days, my girlfriend and I were at different universities but they were only an hour apart by direct train. Normally I went to visit her for weekends. I loved her place, Oxford. They did great lunches on Sunday's. Full roast dinner with wonderful roast potatoes and all you can eat. For a broke, starving student this was a wonderful treat....

Mia More

by seams_straight2me on Sep 16, 2017
Transsexuals & Crossdressers

It was 5 days after my very close encounter with Mia. I was still on very high spirit after meeting her, and fucking her. I could think of nothing else. We kept in touch via text messages and phone calls. She was "on location" for some photo shoot. One less about fashion and more about horny transsexuals having very sexy fun. She sent me a few pictures of...

Man in the Mask

by MiOtroYo on Sep 16, 2017
Transsexuals & Crossdressers

Mel was sitting on the corner of the cheap hotel king-size bed. Aroused, nervous, simply scared by the whole story, he still wanted it to happen. Once a lifetime dream, now a striking reality -- it was all here, from the remote sound of the cars passing by to that filthy, nasty smell of the motel building... "Hi, my name is Melinda. I am a young closet cros...

Jessica Ch. 01

by jac0879 on Mar 18, 2020
Transgender & Crossdressers

It was a familiar ritual by now. I plugged the drain of the tub and turned on the faucet to draw a hot bath. It was really a pain keeping my body hair tamed, it grew in dark and quickly but I was determined. As the water ascended in the basin, I stripped my clothes, stood in front of the sink and grabbed a razor. I quickly dispensed of every last trace of st...