Caught Crossdressing Stories

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Just a Girl

by katie_risita on Sep 18, 2017
Loving Wives

My name is Frank. OK, it WAS Frank, until recently, when things...changed. Now, more often than not, I answer to Katie. I know, I know. Yes, I am a guy, technically, but, well...to explain, it's gonna take a story, a loooong story...but not a boring one, I promise! I am a 33-year-old guy from Long Island. I have always been overweight, not great-looking, s...

Caught Out at Work

by alexis19901 on May 12, 2020
Fetish

For those of you who have read the stories that I've already put on, you will already know a bit of my back story, but for those of you who are reading a story of mine for the first time, I will give a bit of background in the intro. WARNING - This story contains m/f, pegging and some crossdressing. So, for those of you who aren't aware, I've taken to wr...

Caught by my Daughter and Wife

by rickiee_2002 on Sep 12, 2017
BDSM

It was Saturday morning and I heard the door to the garage close. My wife and daughter had just departed for a weekend in New York City. I was excited for them because they need some girl time together. I call her my daughter, but she is actually my step daughter and had just turned 21 years old on Friday. The two of them got along like oil and water ... the...

Sissy Slave

by mikedoreilly1973 on Nov 24, 2018
Fetish

It was late friday night, and Mike had just gotten home from work, he was tired and filthy from work and decided to take a much needed shower, he went to the bathroom and noticed the door was slightly ajar, he peeked inside and saw his 18 year old daughter Samantha taking a shower. Samantha was his daughter from his previous marriage which had ended badly wh...

Marion's reTurn Ch. 02

by jomar on Sep 13, 2017
Fetish

If crossdressing and male-male sex isn't to your taste, please back out and try one of my other stories. Also, the action here is not safe sex, but this is fiction, after all -- pretend. ********** I stopped at the door and ran my hands down my sexy little black dress, pressing the wrinkles out. I felt the tug of my ebony earrings as I looked down and saw...

Donny Gets Caught!

by RisisWrites on Apr 22, 2025

His heart thundering in his chest, Donny pressed the upload button and almost immediately the door to his room slammed open and his step-sister Nadine stood in the doorway. “Sprung!” she yelled victoriously, holding her phone up to show Donny the picture he had just uploaded to what he thought had been his ‘secret’ social media account.’ “Nadine! Um- it’s no...

Camping Out

by Sexyleggs on Oct 31, 2018
Anal

To begin with. I had been turned out and was actively crossdressing and being used by my older cousin. My cousin is best described as a football star, jock. Over 6 feet tall and solid steel! I'm younger, short, and as always, small. I'm slender, tan, and have great legs. His description. He caught me in panties playing and used this to blackmail me and t...

Sissification 101: Ch. 01

by silkstockingslover on May 4, 2020
Fetish

Summary: Straight guy is caught watching sissy porn and...Note 1: Thanks to Eric who requested and helped plot this lengthy story. Note 2: Thanks to Tex Beethoven and Robert for editing. Note 3: All characters are at least 18 years old. Sissification 101: Ch. 01 1. MY SISSY CURIOSITY I've always liked nylons. I grew up when they were still popular and...

Marion Turns Me Out Ch. 02

by jomar on Sep 13, 2017
Fetish

If gentle femdom, crossdressing, strapon and male-male sex isn't to your taste, please back out and try one of my other stories. And let's imagine this is set in a world where unprotected sex is safe. ********** It was looking to be a glorious day. Marion and I were on vacation in the tropics at a five star resort. We started the day with Marion touching u...

Stacy and Matt

by mattpantyhose on Jan 28, 2020
Fetish

Matt's bliss ended almost as soon as it had begun. The girl he had met and who not only was pretty and smart, but also enjoyed his crossdressing decided that career was her priority after merely few weeks of their relationship; the two broke up as she moved to a different distant city. Matt still had a good job, amazing boss and sympathetic co-workers, but d...