Caught Cross Dressing Stories

192,094 results
Orientation
Length
Source
Infinite Scroll

Daddy Jack Pt. 02

by RoryOmore on Dec 17, 2018
Transgender & Crossdressers

"Oh my God, look at you, Jack," Melanie declared as soon as I let her through the door. My first thought was that my boner was sticking out the flap of my boxers. The sudden interruption had reduced it to a semi, but it could easily be drooping out. I tugged on the T-shirt I'd hastily pulled on, but it didn't reach very far past my waist. "Hi, Melanie," I...

Internet Meeting

by Stillherer on Sep 16, 2017
Fetish

We met on the net. How modern. He was shy and nervous, very much like I was though if anything even more cautious. Being a closet cross dresser with a life outside my apartment door my main aim was discretion and major fear -- discovery. Charles appeared to be perfect for my yearning to fulfill my fantasies and spice up my solo adventures. We chatted online...

One Fine Day

by TomCarter on Sep 16, 2017
Transsexuals & Crossdressers

This is the story of my first date with Wendy in the summer of 1981. It is a prequel to 'Room 139', which takes place on Halloween of that year. The sex takes a back seat to the story, but hope you find something in this regardless. ************************************************** "Do you wear girl's underwear?" The question caught me off guard. Wend...

The Bridge of Thighs

by buck_maelstrom on Sep 13, 2017
Erotic Couplings

The Bridge of Thighs: Naked and Voluptuous in Venice by Buck_Maelstrom, M.D. and Miss Manners with a Whip Mia glanced down her shapely legs at her espresso kid leather t-straps with three-inch heels and wondered if they were the most practical choice for wandering through the streets of Venice. With delicate steps, she traversed the uneven stones of Ca...

Basketball Crossdresser

by Cute Little Thing on Sep 14, 2017
Fetish

This story is about an athletic but small man who has fantasized about cross dressing from an early age. When his wife finds a strange number on the phone bill, she calls the number and has a conversation with his phone mistress. What follows contains blackmail, humiliation and of course - sex. If sex and crossdressing offend you, or if you are underage, ple...

The Trainer Ch. 01

by ADjann on Sep 17, 2017
BDSM

[[ This is the first in what will hopefully be a long running series about the slave trainer, Alexander D'jann and his girls and boys. As with most stories I write, this is intended to be linked with a song. In this case you should check out Preach and Pervert by KMFDM as the companion music ]] The Catholic 3 slept the sleep of the contented, that was the...

Sissy Finds a Friend

by Quietoldie on Apr 10, 2019
Transgender & Crossdressers

Andrew likes to wear women's clothes in the privacy of his home. He finds he's more comfortable dressed as a woman, and wearing frilly clothes makes his cock stiffen up nicely. He's been married to Wendy for ten years now. She discovered his fetish by accident six months ago and has come to accept his need to cross dress. When she returned home early one da...

Fixing The Car

by pup12 on Sep 16, 2017
Transsexuals & Crossdressers

I had been cross dressing since I was about 10 years old, I'm now in my thirties and this story is about my first encounter with another man. It all started one day when my wife would be out for the day and I had settled down to surf the net looking for transgender sites, I was only dressed in a black lace garter belt, black hose and high heeled black pumps....

Silky Stockings

by dirtyjoe69 on Sep 16, 2017
Transsexuals & Crossdressers

I can't remember the first time I put them on but I have come to love the feeling of silky stockings as I pull them up my long legs. It doesn't stop there either. After I first started wearing ladies stockings I took it even further. I know love wearing bras and panties as well. I just love how soft they feel on my body. My cock always responds in full forc...

Benns Feminisierung

by Racsomann on Apr 6, 2020
Amateur

So richtig Lust hatte Benn nicht auf den Geburtstag seiner besten Freundin. Sonnst waren nur Mädchen eingeladen. Aber er mochte Lisa, also ging der 18 Jährige am Freitagabend auf die Übernachtungsparty.What's next? Die Charaktere Aller Anfang ist Schwer What's next? Die Charaktere Aller Anfang ist Schwer...

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