Crossdressed Stories

155 results
Orientation
Length
Source
Infinite Scroll

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...

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...

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...

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...

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...

Sissyhood of Travelling Panties Ch. 01

by daddyslittlebitch on Sep 14, 2017
Transsexuals & Crossdressers

Chapter 1: Alex A pair of red satin panties lay on the bed. They were boyshort style with little red lace bows above the crotch. Very sexy and very slutty. Helen ran her fingers along the soft, smooth material. She was dressed in a black lace garter belt holding up thigh high stockings, her large, round breasts, still firm at the age of 45, stood out naked...

David's New Experience

by zxsgxwlp on Sep 13, 2017
Transsexuals & Crossdressers

It was a hot summer's day and David was taking a shower. He was alone in the house and was taking his time washing his tall, athletic body. Once the shower was complete, David dried himself off and tied the towel around his waist. He walked across the landing to his room and made his way to his cupboard. As David moved thorough his room, he heard a noise beh...

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...

Just Look at Me Now Ch. 03

by GFfan on Apr 13, 2020
Transgender & Crossdressers

Eager as I am to tell you about my first crossdressed Halloween with Jude and Becky, I must save that for a later chapter and fill you in on some major developments that occurred as my first summer of feminization ripened into autumn. Surrounding these landmark events were patterns of submission we had established early on. I wore panties 24/7, and I shoppe...

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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