Crossdresser Caught Stories Stories

187,637 results
Orientation
Length
Source
Infinite Scroll

Sarah Wore a Bikini to the Hot Tub

by SarahCD on Feb 11, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more detail and corrected some...

Michele and Buster: A Tranny Tale

by MicheleNylons on Sep 14, 2017
Illustrated

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

Discounted Carpet

by Leigh_216 on Jul 31, 2019
Transgender & Crossdressers

My name is Leigh. Well my girl name, I am a cross-dresser. I just feel right to me and I guess that is how I am. All my stories are based on truth; but the places and names have been changed. Friday night and I was ready to hits this clubs but I needed to stop at my Aunt's old house on the east side of town first. Long story short: The family was selling it...

Miss Khandie Ch. 03

by SweetNightingale on Sep 16, 2017
Transsexuals & Crossdressers

(Dear readers, sorry it's taken so long to post this next part, I'm busy with RL shit. Feed back welcome, please please please tell me what you think!) Xoxo Nightingale [1] Alright, so we all know that whatever happened between Frank and I...Will never happen again....right? I love Tanya, not Frank. I hope you all know that. We also know that we were ma...

Michele Nylons' True Stories Ch. 02

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

In part one of True Stories I discussed how my transition from part time panty wearer to part time Transvestite came about. I also told the true story of my first time with a Transsexual prostitute. In this instalment I have decided to leap ahead to the present and tell you a true story that occurred only last week; that is July 2006. I am a part time Trans...

Driving Her Home

by bored_doe on Sep 16, 2017
BDSM

Alan smiled at the perky blonde college student in the passenger seat of his sedan. "So Catelyn, have you figured out what your major is going to be yet?" "Mister Denny, are you wearing makeup?" It wasn't a question, it was a challenge. Her brown eyes watched him without flinching, waiting to see how he'd respond. The question was so unexpected, it knifed...

The Glass Door

by JackOLantern on Oct 16, 2018
Fantasy

((Author's note: I have made this story open to the public. I encourage people to post their own chapters and threads. If you are a potential writer want an idea of how the mirror works, read the first handful of chapters in my main thread to get an idea. You are under no obligation to make it function in the same way unless you want to, however. Have fun wi...

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Home in the Hills Pt. 01

by ValoryG on Dec 10, 2019
Transgender & Crossdressers

All names and characters in this story are fictional and have no connection with any actual person living or dead. ***** Jonathon Worley is in his sophomore year at Onanoma State University, majoring - at least for the time being - in art history. He's the third child in his family, and after his parents paid for the first two to go to college, there was...

Kasey's Confession Ch. 03

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

The morning after Mike and J.J.'s visit I woke up feeling a lot of strange and conflicting emotions. On the one hand, I felt a sense of relief in knowing that Mike wasn't going to continue to visit and want me to suck his cock. On the other hand, I felt like I'd just been dumped, but feeling like I'd been dumped by a guy was something I'd never imagined feel...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...