Pantyhose Crossdressing Stories

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Infinite Scroll

The Hitman Wore Heels

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

The well dressed man looked with disgust and loathing at the bum rummaging in the dumpster in the dark alley. Tony 'Tough Tony' Provalono had just left Scalini's, one of the best restaurants in New Jersey, where he had tipped the waiter more money than the hobo was likely to see in his lifetime. Tony was dressed in Armani; the gorgeous woman beside him in Pr...

Gordy Gets a Skirt Ch. 02

by KristaMorane on Feb 10, 2020
Transgender & Crossdressers

I wish to thank Mike Lair for feedback, discussing ideas with me as my editor. *** As expected another box arrived before the weekend making him the proud owner of four bras and six panties all free samples from his employer, the lingerie leader, Maidenform. Free in exchange for wearing them daily and giving feedback on fit. He was tricked into the runway...

A Special Night, Laci's First...

by Sissy_Chantel on Nov 27, 2018
Transgender & Crossdressers

Prologue: My name is Lawrence, I'm a young 40 something widowed white male, living a heterosexual life. However I have my feminine side, her name is Laci and as such I am a transvestite. I have preferred the long classical term of transvestite for a genetic male who dresses in women's clothes. But crossdresser also works as well. As a transvestite in my fu...

Mistress Chantel, Tranny Dominatrix Ch. 04

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Four: Chantel Hams it up with Kerri and Friends. Beep, beep, beep, my alarm clock goes off. Lying under my fluffy covers and on my satiny bed sheets, face mushed half buried in a pillow I awake, glance at that damn clock and see 9:00am. It's Sunday and I do not have to be up at any specific time but I do not really like sleeping in as I feel it wast...

My "Uncle" Caught Me in Pantyhose! Pt. 04

by JHouston on Sep 12, 2017
Transsexuals & Crossdressers

Continued from: https://www.literotica.com/s/my-uncle-caught-me-in-pantyhose-pt-03 I was left in the shower alone to contemplated everything that had just happened. This was surreal. I just lost my virginity! The experience had been a strange mix of horror, pain, eroticism and pleasure. My insides and my jaw were sore. I had bruises on my hips where Rob...

Pillow Talk Ch. 01

by MicheleNylons on Sep 11, 2018
Transsexuals & Crossdressers

Chapter One - Half n' Half Michelle Clooney stood on the windy cold street corner; it was gloomy, with most of the streetlights either deliberately broken to mask the street crime or simply blown and not replaced by a City Council that was going broke. The flickering neon signs of the titty-bars, greasy spoons, porno palaces, and sex shops reflecting off th...

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...

College Crossdressing Confessions Ch. 04

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

My wife's control over me insures that I have no secrets from her no matter how depraved my hidden desires. This is the fourth in a series in which I confess my past experiences as a panty thieving college cross dresser. I have changed some of the names, but the rest of the confessions are, sadly, true. Please read the first three installments for context....

My First Time Dressing Ch. 01

by ChrissyCD on Sep 16, 2017
Transsexuals & Crossdressers

This is the first of hopefully many stories to come. This one may be a bit boring and lacking the hardcore fucking and sucking so many of you are used to. I feel the need to tell it because it will give some background to the rest of my stories. For the most part I will send them in chronologically from my younger days to present day as a undercover crossdre...

My "Uncle" Caught Me in Pantyhose! Pt. 06

by JHouston on Sep 16, 2017
Transsexuals & Crossdressers

"You will make a hot little sissy in those heels and dress." said a man's deep voice behind me. I was startled. I was shopping alone in a boutique and adult novelty store near my new rented apartment. I had just moved in two weeks ago to be closer to my new college, and, I was picking out a few sexy outfits for crossdressing fun. I turned around to see a t...