Caught Cross Dressing Stories

192,094 results
Orientation
Length
Source
Infinite Scroll

Cross Dresser Flashing for Nude Day

by SuperHeroRalph on Sep 16, 2017
Transsexuals & Crossdressers

This is a Nude Day contest story. Please vote. * Having fun flashing the sexy, pretty neighbor his pantyhose clad cock on Nude Day James, a cross dresser, had some sexy flashing fun planned for Nude Day. Taking a long sensual and sensuous bubble bath first, wanting to look pretty, feel sexy, and smell divine, he took his time getting ready by shaving, wax...

Her Doll Ch. 01

by WickedDoll on Sep 16, 2017
Transsexuals & Crossdressers

'What would you like, girls?' Quietly amused, I smiled at Samantha who eagerly gave our drink order as we settled into a corner booth at one of his favorite alternative lifestyle bars. Or should I say her. No difference. Sam was Samantha during the weekend and I was accepting of his chosen uniqueness. As long time friends, I knew it pleased him when he was...

Freddie Becomes a Cross-Dresser Ch. 02

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

I walked in the store and continued over to an area where there weren't too many women. Even though I wanted to cheat and buy a pair of jeans, I figured that I'd have to wear a dress to experience the real effects of cross-dressing. There, that's another insight. Cross-dressers probably, I'm thinking as I wrote my thoughts in my notebook, would rather wear d...

Do You Know A Cross-dresser?

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

Trans-genderism: Cross-dressing I never considered writing a story about cross-dressing until I was confronted with it. I just recently found out that a friend of mine who I have known for several years is a cross-dresser. He's a good guy, a family man, is married with kids, and, by all accounts, appears normal. Whatever that means? Yet, what is normal? Am...

The Transvestite Divorce Transcript

by desireethtttv on Aug 1, 2018
Transsexuals & Crossdressers

We begin with the plaintiff, the woman of the marriage of 33 years, from hereto within known as Mrs. S. Verses the transvestite husband we shall call Desiree. Mrs. S Attorney (referred in future testimony as AFM: Please state your reason for the divorce proceedings, if you please Mrs. S. Mrs. S: I wish to divorce my gay transvestite husband due to the lack...

Changes Ch. 02

by sublocked on Sep 25, 2017
Transsexuals & Crossdressers

Notes to Reader: (1) A lot of this is fiction; much is fact. (2) Cross dressing in marriage is a difficult situation; acceptance of it comprises three entities: husband, wife, couple. (3) Nobody CHOOSES to be a cross dresser, so please don't demean yourself (the reader) by macho dismissal and criticism. Lawyers, plumbers, truckers: anyone can be one. Most...

Hot Sex Instead of Dancing Ch. 17

by SusanJillParker on Sep 16, 2017
Fetish

Please give me the support of your vote. * Walter shows Tiffany his extensive women's shoe collection. "I'm sorry I mentioned my stripper clothes," she said with sadness. "Maybe some other time. I'll bring out all of my bras and panties for you to see them, touch them, and sniff them another time," she said with a laugh. "Okay?" No doubt she was kidding...

Could It Happen Again?

by mumblegooseegg on Sep 17, 2017
Loving Wives

This story is dedicated to those readers who liked "It Has Only Happened Once," a previous story of mine, and especially those who documented their positive feedback: RyeandGingerAyle, bruce22, johnnyjay85, HappyWife85, Grayhair61 and Bill (via email). Thank you, all of you! Here is a happy sequel to the saddish ending to that story, with my wife Linda losin...

Freddie Becomes a Cross-Dresser Ch. 01

by BOSTONFICTIONWRITER on Sep 16, 2017
Reviews & Essays

I was determined to write a transsexual and/or cross-dressing story for Literotica's 2008 Survivor Contest. I thought that I had written a cross-dressing story when I wrote Do You Know A Cross-Dresser, Ch. 02, but that was placed in the Reviews and Essays Category. Then, I thought that I had written a transsexual story when I wrote Transsexual Sex with Vinni...

The Psychosexual Motive in Writing

by Da_Vida on Sep 16, 2017
Reviews & Essays

I have been a writer all of my life. My employment as an adult has, to a large extent, depended on my ability to get published, which I suppose makes me a professional writer. In addition to writing, I've also served as a consulting editor for a number of publications. I am no stranger to the written word. The motives for writing erotic fiction no doubt va...