Caught Cross Dressing Stories

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Orientation
Length
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Infinite Scroll

Lisa, A Story From A Male Admirer

by RubberBudcus on Sep 16, 2017
Transsexuals & Crossdressers

This story is based on the truth and real people. It all started in a routine sort of a way. Well, routine in a Literotica sort of way really! Let me explain. I am a lifetime fetishist. Male, 63, heavy build and hairy to gorilla standard. I experimented at an early age with wet clothing and kept at that converting to female attire through two marriages, tw...

Caught Cross-Dressing!

by StephanieSeymour on Sep 13, 2017
Transsexuals & Crossdressers

I was on the bed with a vibrator jammed up my ass and my girlfriend's bra strapped to my chest when she came home early from work. She caught me scrambling for the remote to turn off the cum shot porn I had playing on the TV. "What the fuck?" she asked. "Fair question," I said. I rolled off the bed and did my best to play it off. But as my mind reached f...

Black Mistresses For Black Sissy

by Samuelx on Aug 18, 2017
Fetish

A lot of Black women in the world of BDSM consider themselves dominant, which is fine, but they seem to cater exclusively to White male submissive types. I take my clients anyway they come, since I am a professional dominatrix. I do enjoy playing with Black men, though. Unlike White subs, the brothers always make you work for it. My name is Shana Drummond an...

The Best Game

by starrkers on Sep 17, 2017
Loving Wives

Janey was taking a break from her shopping when she first saw him. He was tall, dark and handsome, of course, why else would she have noticed? She was sitting at a sidewalk table of the local cafe, deciding where next to spend Arnold's hard earned cash when he sat at the next table, perfect jeans moulded to his perfect arse, eyes tantalisingly hidden behind...

Fun With Friends

by HighHeeledHoney on Sep 11, 2017
Transsexuals & Crossdressers

This story is a work of fiction, although some of the facts within it are true! Thanks to kjplotts for helping with the structure of the story. I am a 28 year old single heterosexual male who happens to enjoy cross-dressing. It started with the desire to wear high heels and after that developed into pvc, leather, latex...anything slutty to be honest. Th...

You Can Always Say No Ch. 01

by AngelCherysse on Sep 25, 2017
Fetish

I have always considered myself a liberated woman. Rising through the business ranks to become a Vice-President at a major media consulting agency was just one of many goals I set, then met. I don't see any conflict between that and being a 'girly-girl'. I'm not ashamed to admit; I have used my raven-haired beauty and generous natural charms to advance my ca...

Influential Factors! Ch. 02

by gummidurango60 on Sep 12, 2017
Transsexuals & Crossdressers

The alarm rang and I woke tired, thoughts of last night put a smile on my face. Finally, I don't have to hide my cross-dressing from Jill any longer. I jumped out of bed, took a shower, and toweled off quickly. When I reentered the bedroom I noticed Jill had laid out some clothes for me on the bed with a note. It read, "Prepare for a day of fun!" I had...

The Making of a White Sissy Slut

by AfroerotiK on Sep 18, 2017
Transsexuals & Crossdressers

When he replied to my ad online, Steven said he was an attractive, 30-something, successful white man who was willing to explore the wild side. When we met in person, I was more than a little bit disappointed. Attractive was a stretch of the imagination and I told him so right off the bat. He acted as if I'd said something to offend him and responded by sayi...

Chrysalis of Kirsten Ch. 01

by kirstensubts on May 7, 2019
Transgender & Crossdressers

My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transgender slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been changed. This is who I am. A special thanks to Shy Girl Whore for her help with polishing this story!...

A Mistress' Blog: A Day in the Life

by CastleDJK on Sep 14, 2017
BDSM

9:30 AM: I awaken as I do every morning...to the soft sounds of classical music and my arms wrapped around my female sub, Sleepy. I don't like to sleep alone. I like to have someone to hold on to...to be my teddy bear...to squeeze and to cuddle. She is soft and warm and naked and I always seem to wake up with my hands clutching her tits or my head nestled be...