Nylon Stockings Crossdressing Stories

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Infinite Scroll

The Transvestite Stalker

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

The man sat at a corner table in the coffee shop surreptitiously eyeing off the woman sitting on a stool at bar. She was dressed in a navy blue suit; her jacket was open, revealing well-formed breasts swelling her white satin blouse, which opened to the second button so that a hint of lace bra was displayed. Her legs were crossed and her skirt had ridden up...

My First Time Dressing Ch. 02

by ChrissyCD on Sep 16, 2017
Transsexuals & Crossdressers

This is a continuation from my first story where I bought and completely dressed in women's clothes and started my transformation into a crossdressing slut. Chrissy's First Real Cock After my first night dressed up like a girl I started to wear panties and thigh highs under my pants when I went to class or anywhere for that matter. I couldn't get over the...

Rm 209: First Sex as a Crossdresser

by MelissaMwaz on Sep 16, 2017
Transsexuals & Crossdressers

This is a TRUE STORY. I've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a kid and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-...

The Photographers Assistant Pt. 02

by panty_wearing_sissy on Nov 13, 2017
Transsexuals & Crossdressers

If you are under 18, please stop reading and delete this document immediately. This story is pure fantasy. It does not relate to any real events, either past, present or future, and is only suitable for persons over the age of 18 mature enough to understand, and distinguish the difference between fantasy fiction and real-life. ***** Jake didn't remember e...

Twenty-One More Questions

by silkstockingslover on Jan 1, 2019
Reviews & Essays

Summary: Jasmine responds to the most frequent questions asked by readers. Thanks to: Tex Beethoven, Wayne, and Robert for editing this essay. This isn't really a sequel, although it's a second part, as it addresses questions I didn't answer in 2017's Twenty Questions. 21 More Questions After 2017's 20 Questions, I received many more questions. I have n...

Passion over Lust

by sarahchica96 on Sep 5, 2018
Transsexuals & Crossdressers

Introduction I' am living the dream, the dream of maintaining the balance as a regular straight guy and my bisexual crossdressing side Sarah. The 4 years of hard work at University started paying dividends, I landed a job as a legal advisor for one of the top businessmen in London Mr Hayat. My job paid well which enabled me to buy a studio apartment via a...

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...

Maid to Surrender

by CarrieQ on Sep 16, 2017
Transsexuals & Crossdressers

When Mr Hastings first phoned me, I had no reason to think he was anything other than an ordinary client. I mean, so what if he asked me to turn up dressed as a chambermaid? That was one of the options mentioned on my business card. Transvestite maids have always been popular... My maid's outfit was the flimsiest kind; really just a cheap black mini-dress w...

My Seduction into CD'ing & Gay Sex

by pantycladlad on Sep 18, 2017
Transsexuals & Crossdressers

MY SEDUCTION INTO CROSSDRESSING & GAY SEX It all started out easily enough. Mr. and Mrs. Ferguson had been our neighbors for many years. Their backyard abutted our backyard, a bit at the side of the end, so contact was frequent but not too much so. They socialized with different friends, maybe because my parents were younger, but were certainly nice neighbo...

What is Going On?

by dontholdyourbreath on Sep 13, 2017
Transsexuals & Crossdressers

This story is dedicated to Ms. Karen-Anne Brown and all the amazing Nifty transgender writers who wrote mind control stories back in the 90's. I grew up reading Nifty stories and always loved the mind control category so I felt compelled to try my hand at it. I hope I did all the great writers who have come before me a little justice. Please also check out m...