Crossdress Stories

204 results
Orientation
Length
Source
Infinite Scroll

Home Helping Hands

by Kashman007 on Jun 28, 2020
Erotic Couplings

“Hey Andy, what about this one!” John threw the paper to Andy who was slumped on the sofa watching daytime TV. “What am I looking at?” “The wanted ads – somebody wants a home help” Andy sighed. “Oh great – basically a cleaner. That’s not gonna go far to getting a deposit for my own place, is it?” “No – look at the ad. It says the job is 7 days a week, so the...

Open in Reader

Caught by my Daughter and Wife

by rickiee_2002 on Sep 12, 2017
BDSM

It was Saturday morning and I heard the door to the garage close. My wife and daughter had just departed for a weekend in New York City. I was excited for them because they need some girl time together. I call her my daughter, but she is actually my step daughter and had just turned 21 years old on Friday. The two of them got along like oil and water ... the...

The Girlfriend Ch. 04

by nikkiesilk on Apr 17, 2019
Transgender & Crossdressers

"Well, what do you think, Joe? Do I look cute?" He winked at me. "Don't look like that, I'm only teasing you. Come into the kitchen, I haven't finished cooking yet. Open that bottle of wine and pour us a glass. Glasses are over there in the top cupboard." I didn't know what to do. Seeing Sam dressed as a woman had really startled me. I hadn't expected him t...

Walk a Crooked Milf Ch. 03

by MicheleNylons on Nov 16, 2020
Transgender & Crossdressers

Chapter Three - Relax and Take What I Am Offering You Three weeks of agony... that's what Mrs Cashmore put me through. She didn't invite me over and she refused to see me or to answer my calls. Worse, she seemed to spend more time outside than usual, deliberately teasing me; dressed provocatively and ensuring that I saw her. She knew I was watching her and...

Transvixen Tranny Rock Band Ch. 01

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Chapter One: Panti and Cherri Pops Panti's red nailpolished finger lazily circled the glans of Cherri's erect penis through Cherri's gauzy nylon pantyhose gusset. Preseminal fluid seeped from Cherri's palpitating member and darkened the sheer nylon. Cherri's white satin panties were bunched around her thighs and she bucked and heaved as Panti gripped Cherri...

Life and Time of Lady Vargos Ch. 08

by rik581 on Mar 26, 2019
Transgender & Crossdressers

"Lies, Truth, and Innuendo" Martin was pressed into attending to his duties that week as Lady Vargos. With little or no manly pride left to swallow or cling to, he performed his daily routines dressed as a woman, both publicly and privately. Each day seemed to bring more heart felt shame and humiliation into his life as he stepped out and displayed his ema...

A Dirty Little Theory

by bigrusker on Jul 30, 2019
Transgender & Crossdressers

I have a theory. Or maybe I'm just trying to justify how it came about, but for now let's call it a theory and stick with that. Capiche? Excellent. Glad you're on board. Now, as I said, I have a theory, and it goes something like this: if you marry someone that's of a similar size, eventually you end up wearing their clothes. I think most of the time it ha...

Mistress Chantel, Tranny Dominatrix Ch. 03

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Three: My Saturday Meeting with Kerri. Well another busy but fun week for myself as Mistress Chantel begins to wrap up. It's a bright, sunny Saturday morning about 7:30am. My typical femme routine is to shower, dry off, moisturize with fragrant, moisturizing cream then to shave my face. Luckily for me in recent months I have begun to use a beard ret...

Whores And Pimps Ch. 01

by MicheleNylons on Sep 12, 2017
Transsexuals & Crossdressers

Malcolm was a middle manager in a small business in a large city. Malcolm led a pretty boring life; he in his forties, single, devoted to his work, he liked to keep himself fit, all of his family lived interstate except for his older sister who lived nearby, and he led a quiet social life. Malcolm had a few girlfriends over the years but never anything serio...

Being Sarah

by Alex_Lockheed on Sep 25, 2017
Transsexuals & Crossdressers

Please note, this is a story about a male-to-female crossdresser. It includes themes of bisexuality, dominance/submission, embarrassing erections, anal play, cunnilingus and cum-eating. If you like that, awesome. If you don't maybe it's time to check another post. You can't say I haven't warned you ;) **** There are many difficult decisions I've had to ma...