Crossdress Wife Stories

121,268 results
Orientation
Length
Source
Infinite Scroll

How I Became Sissy Willow Ch. 02

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

"Now the preliminaries are over, and it's time for the entertainment part of our evening!" That was what Fern, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Jason. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completing the transformation. Fer...

A Weekend Getaway To Crossdress In

by crypticguy143 on Sep 13, 2017
Transsexuals & Crossdressers

Hi All, I am 32 years old married guy without any children living in California. I believe I have had the bisexual urges since my early childhood. But I somehow developed a new fantasy to cross-dress in last couple of years. Since then I have been thinking about it pretty much all the time and been trying to explore it. Couple months ago my wife went out w...

Michele Nylons' True Stories Ch. 04

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

This is a continuation of my True Stories series, where I tell my readers about my real life adventures as a part time Transvestite. In this instalment I will tell you about my most recent encounter; my first encounter for some time, and also for me a milestone; my first time out and about dressed as a Transvestite. This is the story of my latest encounter,...

In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...

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...

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...

Maid to Order Ch. 02

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Mick had been shit unlucky. He had driven over sixty miles on the day she bought all of his girly accoutrements. He had even stayed overnight, confident that she wouldn't run into anyone that he knew while he was shopping. But, as has been said, he was shit unlucky. Of all the people in the world who happened to be in the same city, shopping in the same sho...

My First Time

by sexyctcd on Sep 18, 2017
Transsexuals & Crossdressers

As the rain pelted down on the roof I sank into the warm water of the bubble bath. I couldn't believe my luck. I was all alone in the house and now the rain had given me a day off as well. Just as I lay back against the tub my phone beeped a text from my wife. She had met her mom and they were on their way to the city for the day. I stretched out my long leg...

The Awakening Ch. 01

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Part One -- The Woman In The Mirror Dark; then light; my eyelids flutter. "Can he hear us?" a woman's voice. Dark; then light. "He's still comatose; but he's improving," an authoritative male voice. Light; now dark, the dream returns. I'm inside the mirror but I can't be seen. I try to reach through the glass but I can't. I try to speak but I am mute....

Inaugural Crossdress Sexfight

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

Hi everyone and welcome to the Crossdressers Sexfight League (CSL). My name is Dani and I'm the primary author as well as a regular participant in the league. The league title says it all. It's an erotic sexfight wrestling league for crossdressers of all ages where the loser is forced to service the winner of each match. It takes place in living rooms, bedr...