Pantyhose Crossdressing Stories

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Infinite Scroll

Pretty in Pink

by jealouscuck on Oct 8, 2019
Fetish

I always remember thinking how bland men's underwear was compared to women's. In the animal kingdom, the male usually has the prettiest colors. Not so in people. I suppose traditionally, men's underwear is supposed to be functional while women's are fashionable. I was a late maturing kid. I was probably about two years behind some of my classmates. When I d...

Halloween Party Aftermath

by Sabnock on Oct 19, 2020
Transgender & Crossdressers

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy...

The Devil You Know Ch. 02

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Brian Davies sat at his desk struggling with his conscience as he remembered what had occurred the previous evening at Mike Harris' house. He didn't think of Mike as a man in drag; he thought of Mike as the uber-sexy transvestite Michele Nylons. But the outcome of his visit to Michele's had not turned out as he planned it; he had taken liberties with Michele...

Recruiting of a Sissy Maid Ch. 03

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Three: Training Done, Chantel is On Her Way. Waking up back in her cell, Chantel finds that her days being trained, orientated and broken off will here with the Burrows brothers are wrapping up. Mitch enters her cell and has her come back out and back into the house with him and Nate. Mitch says, "Well Chantel, time has come for us to part our ways...

Dressed for Disaster: The Prequel

by thrillerauthor on Sep 14, 2017
Transsexuals & Crossdressers

Dressed for Disaster: The Prequel Pat Summers put his suitcases on the bed, and made a quick survey of his room. He noted with approval the full-length mirror on the back of the closet door, and he poked his head into the bathroom to inspect the bathtub and vanity. Not overly luxurious, but they would do. First things first. He opened his computer case and...

Crossdresser Husbands Left Alone

by ColorfulFantasies on Sep 12, 2017
Transsexuals & Crossdressers

Once my wife, Jessica told me she wanted to see this new opera play. I told her I didn't want to, but she wanted it so badly, that I told her to watch it with one of her art-loving girlfriends. She said: -I will ask Amy, then. -When do you want to go? - I asked. -Tomorrow night. -There will be match tomorrow night. I think it will be a very good match....

Yeliza Awakens Pt. 01

by Yelizaveta on May 11, 2020
Transgender & Crossdressers

First of two, hope you like it. Based on real experiences. Part 1: Morning excitement Early on a Saturday morning, he came out of a gentle sleep. He was giddy. As he had been every time. This time was special however, this time he had done the most preparations ever for this event. His legs and pubic area rigorously shaven the night before. His clothes fe...

I Ventured Out.....Oh My!

by amygurl on Sep 15, 2017
Transsexuals & Crossdressers

On the surface I appear to be just a normal average clean cut guy. But internally I am a very conflicted person not really knowing who I am. I'm small in stature standing only 5'6" and weighing 130 pounds and while this led to much ridicule growing up it has been a blessing of sorts in my adult life. You see one of the conflicts in me is my desire to be a wo...

Recruiting of a Sissy Maid Ch. 14.5

by Sissy_Chantel on Dec 16, 2017
Transsexuals & Crossdressers

Readers, I am adding another quick short story of tranny girl Bailey hungry for men and cock. Inserting this story between Chapters 14 and 15 of "Recruiting of a Sissy Maid". I hope you all enjoy it. ***** Title: Another T-girl Bailey out and on the Prowl for Men and Cock Story Friday night, I've been feeling a desire to dress up as Bailey all fucking day...

Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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