Nylon Stockings Crossdressing Stories

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Forced To Have Sex As A Girl

by TammyPanty on May 11, 2020
Transgender & Crossdressers

Forced To Have Sex As A Girl My wife and I were married for over 45 years. She was eight years older than me and one evening during our 30th year of marriage after we had finished having sex she told me sexual intercourse was not something she enjoyed doing as it was uncomfortable for her and she would prefer if we just stopped doing it completely. I was a...

On Strike!

by thrillerauthor on Sep 16, 2017
Transsexuals & Crossdressers

© 2004 by Thrillerauthor I got the idea while listening to the news on the radio, during another grinding commute home from the big city. It seemed a couple in Florida had gotten so sick and tired of their spoiled, neglectful children that they were camping outside their house in beach chairs, refusing to go back to being parents until their brats knuckled...

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...

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...

So You Want to be a Nurse? Ch. 06

by MicheleNylons on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six - Retribution 'Dr Stephen Mortlock esq' the card read followed by his phone number and his work address in a suite of offices used by medical specialists. The folded piece of paper attached by a paperclip read: 'Be there at 7PM sharp. He likes the nurse uniform so wear it and get dressed before you go. Go there and back in a hire car; Polly wi...

My First Time as Sara... Pt. 01

by Sexy_SaraCD on Sep 18, 2017
Transsexuals & Crossdressers

I changed names only to protect them. These stories represent a fully non-fictional account of how I became me. All stories and people are real. Enjoy them. ***** I only knew Steve as my landlord. To be exact, Steve was the only son of the two people that owned the small apartment complex I am currently living in as of right now. My reason for moving he...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

Biker Bitch Ch. 01

by MicheleNylons on Dec 21, 2017
Transsexuals & Crossdressers

Chapter One: Cassie Cassie woke up feeling hungover, hungry, thirsty, beaten and abused. She was still chained to the billiard table in the Beasts of Burden Motorcycle Club clubhouse. She rubbed her ankle where the chain was manacled to her leg. Her nylon stocking had worn through and her skin was red and bleeding. Had it really been four days? Cassie s...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

Alex Struggles to Accept who He Is

by Shy_n_bi on Jul 29, 2019
Transgender & Crossdressers

Alex never thought he'd be living in this moment, a desire that he kept buried ‎deep within for his entire life and now a near reality! His eyes locked on her every move as his heart raced like he had never felt it race before and the battle between pleasure and guilt had all but began leading from his mind to the pit of his stomach! There he was, nervousl...