Nylon Stockings Crossdressing Stories

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Orientation
Length
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Infinite Scroll

The Awakening Ch. 04

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

Part Four – Michele Returns The woman is slim. She is wearing a cerise satin blouse, black leather skirt and black high-heeled pumps. Flesh-toned fully-fashioned stockings sheath her long well defined legs. She is wearing a blonde bob, her bangs direct your gaze to heavily madeup eyes, and she's wearing glistening ruby-red lipstick. She is mature but sexy...

It All Started When...

by crashmatt on Oct 24, 2018
Transgender & Crossdressers

It all started when... well, perhaps that's not a great way to start. It's difficult to say exactly when it started, or perhaps even what "it" is. For the purposes of this story "it" relates to an episode at Halloween, yes I know, another Halloween story. But, you see, in the UK Halloween isn't the event that it is in the USA, and crossdressing for Halloween...

Mistress Chantel, Tranny Dominatrix Ch. 12-13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twelve: Another Play Day Work Day at Our Studio. I arrive at my studio dressed for another day of fun and exciting dominatrix work. I park my "Plum Crazy Girl." step out in my red leather thigh high boots over my black sheer pantyhose. On my feminine looking body is a red leather form fitted mini dress with loose pleated, A-line skirt barely coverin...

Maid to Order Ch. 06

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Michele and Bill talked late in the night stopping whenever their lust for each other overtook their need to converse. Arrangements were made, compromises reached and finally a mutually beneficial arrangement was entered into. "Ok Bill let's call it a night and tomorrow we give our plan a try," Michele said yawning as she stood. Her maid's uniform was quit...

Crossdressing, Piss and Sex

by Lovinhose on Apr 14, 2020
Transgender & Crossdressers

This is a work of fiction, a fantasy that I would love to come true. It also contains 'pissing' (aka 'watersports'), crossdressing, and a crossdressers sex with men, so if you are not into these subjects, this story might not be for you, you have been warned. Also, comments are welcome, but please note, I'm NOT a professional writer, if I was, I wouldn't be...

Matt Becomes Mattie Ch. 01

by clarepanties on Sep 11, 2017
Transsexuals & Crossdressers

Part 1 It was 2006, a day in April; I can't remember exactly the first day of the rest of my life begun but begin it certainly did. And for my wife, Joanna, it also meant a massive change. I was back in England from a business trip to Canada, to Vancouver to be precise, and I had been back four days since being over there. It was a business trip but Vanco...

Fun with a Cherry Popper

by Floydman1 on Jul 2, 2018
Transsexuals & Crossdressers

Quitting time couldn't come fast enough. As soon as I had seen the notification of delivery, I couldn't concentrate on anything but what was inside the box, waiting for me at home. Finally! I was legal as I drove home, but barely. I had just managed to duck a conversation that was guaranteed to take at least an extra fifteen minutes. While I didn't brazenly...

Exploring Sexuality: A Pegging

by silkstockingslover on Sep 25, 2017
Anal

Summary: Husband is pegged by sister-in-law with wife's permission Note 1: Thanks to Robert, goamz86 and Wayne for editing. Exploring Sexuality: A Pegging I was almost in the city when my cell rang. I glanced at it and saw it was my sister-in-law Sabrina. I sighed. I loved Sabrina, but since her divorce she had been as exciting as a Nicholas Sparks mov...

Disgraced Fiancee

by rik581 on Sep 16, 2017
Transsexuals & Crossdressers

"OMG, Laura please, don't make me do this," Dave pleaded one last time as it was now time to stand before her entire family and beg their forgiveness for his sexual indiscretions. She straightened the dress he was wearing, then adjusted his earrings. "No Dave, the talk is now over. You will perform this embarrassing act for me, and ask my family to forgive...

Caught en Femme

by RisqueRavisher on Sep 12, 2017
Transsexuals & Crossdressers

This is the very first story I've written and uploaded here. I'm sort of nervous because it's probably not the best. Don't forget to rate and whatnot. Give me feedback/tips on things to improve on. I'm always looking to improve. Anyway, enjoy xx ***** "I'm going to be home a little bit later, babe," my wife, Annie, called from the alcove. "I'm going out wi...