Crossdressers Chastity Stories

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My "Uncle" Caught Me in Pantyhose! Pt. 04

by JHouston on Sep 12, 2017
Transsexuals & Crossdressers

Continued from: https://www.literotica.com/s/my-uncle-caught-me-in-pantyhose-pt-03 I was left in the shower alone to contemplated everything that had just happened. This was surreal. I just lost my virginity! The experience had been a strange mix of horror, pain, eroticism and pleasure. My insides and my jaw were sore. I had bruises on my hips where Rob...

Fair Is Fair Ch. 03

by bgdddy_2000 on Sep 18, 2017
Transsexuals & Crossdressers

This is a story about crossdressing and bi sexual experience involving male on male contact. If you don't enjoy this kind of story, why would you read it. The following weekend I was once again in drag, but this time my wife was wearing a very similar outfit in white. She looked stunning as we knocked on the door to our friend's house. Short skirts, tigh...

Not My Fault

by Myxy on Sep 19, 2017
Transsexuals & Crossdressers

Look, it wasn't my fault. I was over at my sister Sally's house; she was having a party that night, and I, as usual, was there early to help her with her outfit. I know that makes me sound kind of girly, but whatever, it just shows that she values my opinions! Anyways, I had come over straight from the gym (I'm not what you'd call bulky, but I do keep in sh...

The New Colleague

by hullguy20 on Sep 16, 2017
Transsexuals & Crossdressers

This is my first submission. I took quite a bit of time on it so I hope you enjoy it. Also it is quite long so get comfy. xxx DAY ONE. The alarm burst into life and so did the pain.I checked the time, it was 8.20. Shit! First day of semester and I was gonna be late. I had a quick shower and drove off to the University. The previous night I added the finish...

First Time with a Shemale

by BigAndy922 on Sep 13, 2017
Transsexuals & Crossdressers

I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we say... party favours. I liked my share of porn, and as I had...

Defining Gabriel

by Lacessor on Sep 14, 2017
Transsexuals & Crossdressers

This is a sequel to Finding Gabriel. I am hoping it stands on its own, too. ~~~~~~~~~~ Gabe stared at himself in the mirror. "I can't do this." Dani came up beside him. She was wearing a cute little blue sundress, her brown hair flowing loose down her back. Pretty and femme and graceful, like a dancer. "Why not? You look amazing." Gabe frowned. His eyes...

Best of Both Worlds Ch. 02

by Hippoid on Sep 13, 2017
Transsexuals & Crossdressers

The first chapter of Best of Both Worlds told how I got to know my shy blonde classmate Robyn, and discovered to my delight that she had a fully functional little cock, and described how we spent our first night together. So, maybe read that first. I thought this would be a single-episode story, and much appreciate the reader who said s/he got off on it so...

Kim & Laura

by bestower on Sep 15, 2017
Transsexuals & Crossdressers

Kim had been at University of two months before anyone knew about her secret. To all normal appearances she was a perfectly normal girl, small and cute with jet black hair and a sweet well defined face. Her legs were smooth and thin and these were often laid bare below tiny denim mini-skirts which highlighted her firm rounded arse. She sported a pair of lus...

Don Juan With A Twist

by lushusboobs on Sep 16, 2017
Transsexuals & Crossdressers

A Celebration Stephanie thought that Halloween was the most romantically delicious of the holidays. She celebrated every year since her 21st birthday by going to a costume ball, picking up a masked stranger, and letting things happen as they may. Not knowing who was behind the mask was more exciting than opening a birthday present. There was something abo...

Lattés and Logic Pt. 01

by LostOnTheRoad on Sep 14, 2017
Transsexuals & Crossdressers

I was feeling pretty good about myself, and I have to say, I looked pretty good too. I had just come from yoga, and as I stood in line at the Bar Italia, I felt I had a glow. The stretching had released all the right endorphins, I was thin and Rubenesque in all the right places, and my ensemble was cute with the right amount of sexy. Now I was going to treat...