Caught Cross Dressing Stories

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Holly's First Night Ch. 04

by Queen_Holly on Oct 29, 2018
BDSM

This is a continuation from Holly's First Night Ch.03. I woke needing to go to the toilet. As I moved to throw back the quilt so I could sit up I groaned involuntarily; my shoulders hurt like hell, but there was a very pressing need to get to the loo pretty quick. I was in Zoe's bed, but she wasn't there. I made it to her bathroom and sat on the toilet, th...

Room 139--01

by TomCarter on Sep 15, 2017
Transsexuals & Crossdressers

Summer was coming to a close as Wendy prepared for her first semester at U of I. We had grown close, and I was feeling torn as her departure date neared. I realized there was a very good chance she would disappear into the milieu of college life and that our relationship would fade. And I didn't want to stand in her way. But my relationship with Wendy wa...

Freddie Becomes a Cross-Dresser Ch. 03

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

I walked over to the lingerie section. There was a woman, an employee, who was bigger than me straightening the merchandise. I tried to move to wherever she wasn't but she had radar as to where my next move was going to be. "May I help you," she said with that tone to her voice and an icy stare in her eyes. I really didn't want her help, but I felt that I h...

Kathryn Errs Again

by EddieTheBastard on Jan 22, 2019
BDSM

It was the first time they'd been together when she'd been due on and feeling this bad, aching, anxious and with painful cramps, she'd tried to get him not to come over, but telling him she felt so unwell had been a mistake and he would hear no more from her. She hadn't wanted him to see her, she felt a mess and had scrambled to make herself presentable, a b...

How to Write Realistic Transsexual Characters

by TGirlNerd on Sep 1, 2017
How To

Table of Contents [1] Introduction: [2] Who are transsexuals? [3] Who are cross-dressers and transvestites? [4] What are cross-dressers and transvestites like? [5] How can I relate to my transsexual characters and get into their heads? [6] What terminology should I use? [7] What terminology should I avoid? [8.1] What do trans women look like naked?...

Lauren and Carl Ch. 03

by clarkoverns on Sep 19, 2017
Loving Wives

Chapter 3: Lauren in the Play I learned later on that my wife's experiences with Carl had left her much more emboldened about teasing other guys. The next time this happened was when she auditioned for a play at the local community theatre. Lauren had been a drama nerd in high school, but hadn't been in a play since then. She was really excited when the t...

Dressing Up for New Years

by dirtyjoe69 on Sep 16, 2017
Transsexuals & Crossdressers

My wife and I attended a costume party every year to celebrate New Year's Eve. This year we decided to cross dress with her dressed as a man and me dressed as a woman. I put on her sexiest silkiest garments and she put on one of my nicest suits complete with a fedora. We had a blast at the party, drinking and dancing we were both so passable in our outfits...

An Unwelcome Visit

by BabyPink on Sep 16, 2017
Transsexuals & Crossdressers

It had been over a year since I had split from my boyfriend, Rick. We had a terrible row in which he had accused me of seeing another man. He walked out, never to return. I had tried to give up wearing girls' clothes afterwards in an effort to become a 'normal' person and to try to blot out some bad memories, but the desire was just too strong. I had got bac...

Street Fair

by Rocket19 on Sep 25, 2017
Fetish

Today is the big day, the day you have anticipating for months. You have been a slave to your master for almost a year and several months ago he announced to you that you would be the star attraction at a live bondage and discipline show. He did not immediately tell you where but exactly four weeks ago he let you in on the secret, it would be at the Folsom S...

Age/Sex/Location

by LeanneSinclair on Sep 14, 2017
Humor & Satire

The scene: a text-only cybersex chatroom. "MistressLisa" has just invited "bi_curious_debbie" to a private chat. The following conversation ensues. MistressLisa: Hi, how are you? bi_curious_debbie: fine thanks, you? MistressLisa: Good thanks. A/S/L? bi_curious_debbie: Sorry i'm new here. Whats ASL? MistressLisa: Age/Sex/Location. bi_curious_debbie: Oh...