Crossdresser Caught Stories Stories

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Infinite Scroll

A Dream Come True - The Adult Theatre

by Lovinhose on Apr 14, 2020
Transgender & Crossdressers

The following is a work of fiction and contains crossdresser sex. Hope you enjoy. I welcome comments and feedback, but please note, I'm not a professional writer and I do it for fun and for my readers. My style may differ from others, but it's mine. ********************************************* A Dream Come True-the Adult Theater We have a local adult the...

My Name is Raquel Ch. 10

by Raquels_Panties on Apr 13, 2020
Transgender & Crossdressers

My name is Raquel and I'm a crossdresser. As my profile indicates, I have been a passive reader of Literotica for at least 15 years. During that time, and even before then, I wrote and rewrote Raquel's stories over end over in my head. If this is your first encounter with Raquel, I encourage you to go back and start at the beginning to understand her stor...

What Just Happened? Ch. 02

by annie_00 on Sep 12, 2017
Transsexuals & Crossdressers

02 – Am I a pervert? When we got home it was late in the afternoon. We had been gone all day, first to the salon, then shopping, lunch, drinks and the crossdresser store. I was tired but felt very sexy under my clothes. I did not want Beth, my step sister, to know that I totally enjoyed the experience today. I thought that she would think I am perverted. A...

How I was Forced Out of the Closet

by gtanya on Apr 4, 2018
Transsexuals & Crossdressers

I was again dreaming of the night I would lose my anal virginity. It had been such a constant since last 3 weeks. I had been talking to a beautiful CD named Rachel since last 6 months and with the thought of meeting her in person, I had planned a vacation to China where she was living. The only problem that I had here was I was going to be on the vacation wi...

Forced Entry

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Danny sat at the bar of the Holiday Inn nursing his fourth double scotch, espousing to the man beside him the reasons why his company was the best designer and distributor of accounting software in the world. Danny was a large man in his forties and was running to fat. He was dressed in a travel-weary navy-blue business suit, a crumpled white shirt now open...

Ash's New Life Ch. 01

by maidashley69 on Sep 15, 2017
Transsexuals & Crossdressers

Hello readers my name is Ashley, I am a twenty year old crossdresser. I started dressing around the age of twelve. This is one of many stories I have written. Some parts are real some are fake, I'll let you decide which. Enjoy. My story begins very normally, one Saturday night some friends and I met up at a local alternative lifestyle club in town. We had...

Aphora's Mission Ch. 06

by ValoryG on Sep 15, 2017
Transsexuals & Crossdressers

By all accounts, we were saying a final goodbye to Earth. Even though I wasn't close to my parents (my father a doctor and my mother a marketing professional) I figured my mother would miss me. And I would miss them somewhat, especially at Thanksgiving- and Christmas-time. We six didn't see ourselves as the homesick type, and I personally hoped that Aphor...

The Girlfriend Ch. 01

by nikkiesilk on Mar 26, 2019
Transgender & Crossdressers

"It looks like Sam has a girlfriend at last." "Huh, what?" My attention was fixed on the rugby on the TV and I really wasn't paying attention to my wife. "I said, numbnuts, that a giant sinkhole has opened up in the high street and swallowed the pub and all the customers." "Oh, OK." Rolling her eyes, she said, "What did I just say?" The game was on a kn...

Sarah Helps Clean Out a Garage

by SarahCD on Mar 11, 2019
Transgender & Crossdressers

A friend of mine, Sandy, asked me if I would come over next Saturday and help her clean-out her garage. I had known her for several years and her husband had just left her and so, when she asked me for help, I could hardly refuse. In addition, she is cute and I cannot imagine why her husband would leave her. On Saturday, I went to her house. I only ever we...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...