Caught Crossdressed Story Stories

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Life and Time of Lady Vargos Ch. 01

by rik581 on Oct 3, 2018
Transsexuals & Crossdressers

I am in the process of reposting my stories. *** "The Life and Times of Lady Vargos" is the second book of the Martin Hastings adventures into a life of forced feminization. This story follows the feminization and marriage of a reluctant young man as he is forced to accept his fate as a male/bride, in a same sex marriage, arranged by his family. This stor...

Lady In The House Ch. 06

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

From Part V Harry leant over me and kissed me full on the lips. "That was worth every penny; you are one hot nurse," he laughed. Harry grabbed a handful of my clean white skirt and wiped his cock on it. The silvery gleam of semen and KY jelly stained the fabric; there was also a faint trace of blood. Harry hitched up his pants and made for the door, tigh...

Lady In The House Ch. 08

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

"You!!!" Eddie screamed through the bars, then laughed. "Well done girls, quite a show, I really enjoyed that; and so did Michele obviously," he said snickering and pointing at the tent in the front of my skirt caused by the bulge of my slowly diminishing erection. "Ok fun's over; now get the fuck out of here while Mabel cleans the joint up for tomorrow ni...

Life and Time of Lady Vargos Ch. 14

by rik581 on May 15, 2019
Transgender & Crossdressers

Chapter 14 "Friend or Foe" Martin sat on the bench with Darren in the garden trying to determine how this young man was going to take advantage of this situation for his own gain. What was his angle? Martin now believed that everybody had a reason or was being rewarded in some way for being near him. Martin wasn't sure how to approach the man. He hadn't...

Chance Meeting on eBay of All Place

by Leighharding on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story of a chance meeting which has turned out to be really rather amazing and surprising. ***** I was trolling eBay for some underwear to buy when I happened on a rather large lady selling some used kit. I messaged her to ask specific sizes and she responded straight away asking if it was for me. Normally I would deny that I was buying...

The Hermaphrodite's Curse Ch. 10

by Cleophila on Sep 12, 2017
Novels and Novellas

PART TWO - CAMBRIDGE - 3 - "What do you know about Hermaphroditus in graeco-roman mythology?" Professor Cavendish asked. "I know the poem," Saphy replied, quoting, "'Lift up thy lips, turn round, look back for love, blind love that comes by night and casts out rest.' 'To what strange end hath some strange god made fair the double blossom of two fruitless...

The Life of Janice

by Kim_Oh_No on Sep 13, 2017
Transsexuals & Crossdressers

When she died, I was lost. Drifted in a haze of sorrow. I don't remember when it first started, but I would take a piece of her clothing to bed with me to find comfort, to help me sleep. A scarf, a dress, a shirt she used to wear. It did bring comfort, a way to deal with the loss. I don't remember when I started wearing the clothes, only that it felt be...

Crossdressed by Hot Girls

by tgirlchrissy on Sep 16, 2017
Transsexuals & Crossdressers

While I was a senior in high school I had an experience I would never forget. I had a group of girls that I called my "Ladies" and I was always close with them, I even hooked up with 2 of the 6. One summer night there was going to be a party and they were all going so me and a couple of my friends were going to go too. Earlier that day I was hanging out with...

Stranger Fuck

by hfernandez1983 on Sep 13, 2017
Transsexuals & Crossdressers

It's been a while since I have written something. It's mostly because I have felt so uninspired and didn't know what to write. My main fantasies these days revolve around a man crossdressed while he is pegged by a woman who likes to dress as a man. My last story series Jenny & Mike got a decent reception and I wanted to write more. But like I said, I've...

Sissy life

by Kaori_chan on Jan 21, 2021
Fetish

So Ive always had this fetish. I love wearing panties. My name is Jake and Im a twin with my sister Jane. Ever since I was young I would sneak into the laundry room and wear my sisters panties. Being twins, we were always around the same size. She always had the cutest underwear. It was pink, frilly, and sometimes had cute designs all over them. My fetish de...

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