Crossdressing Wife Stories

121,758 results
Orientation
Length
Source
Infinite Scroll

Cindy's Panties

by secretanon on Sep 13, 2017
Fetish

I am around 24 years old and I have always enjoyed wearing panties. I think the feminine feeling of it all really turns me on. At a young age, I discovered masturbation from cumming on my mothers panties after deciding to be bold and try one out from curiosity. I was never able to fufil my love for panties, being in a house full of males, so I never had a si...

The Doctor's Appointment

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

My wife Jo had been suffering with a bad back for weeks. She works as a doctor and many of the procedures she has to carry out on patients require her to stand up for hours at a time. A couple of moths ago she fell off a horse on an activity holiday we were on. And she's never fully recovered. Urged on by my insistence to get her back checked out properly...

Trading

by WFEATHER on Sep 16, 2017
Transsexuals & Crossdressers

"I have an idea, honey," my wife began in a tone which suggested that she had a sexual idea which she wanted to try. That was how we had begun breath play, with me strangling her with the belt of her favorite robe while I made love to her. That was how we had begun experimenting on occasion with bondage, discovering how she enjoyed being teased while restrai...

Confiding in My Hairdresser

by Leighharding on Dec 19, 2018
Transgender & Crossdressers

I've always had a great relationship with my hairdresser, Mary. She'd been cutting my hair for years and we probably shared a few more details than we should about sex, she made me laugh at some of the naughty stuff she'd been up to! On occasion around a year ago, she came to the new house that I'd just moved into with my girlfriend to cut my hair. The cha...

Perfection

by ValoryG on Apr 23, 2019
Transgender & Crossdressers

It all starts, innocently enough, when Joanna's looking for a dresser. On one hand, she can just go to a big box furniture retailer and get an inexpensive, functional one that looks decent (and build it, of course). Or, she can browse around online and find a new or used one with a more elegant pedigree. Joanna, by the way, is a very practical, elementary s...

Sissy Crossdresser Needs to Please

by Interested4L8R on Dec 11, 2018
Transgender & Crossdressers

My wife is out shopping. I have just a couple of hours to indulge my fantasy before she returns. Yes, that fantasy. The same fantasy you have. The one in which I open my wife's closet and decide what clothing of hers I'm going to wear. I want to dress up. I want to dress up for you. And my little smooth, shaved cock is quivering in anticipation. What will I...

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...

The Awakening Ch. 03

by MicheleNylons on Sep 13, 2017
Transsexuals & Crossdressers

Part Three - The Cost of Doing Business The woman is slim. Mauve satin blouse, navy-blue skirt, black high-heeled pumps. The hem of her skirt teases the backs of her knees. Taupe stockings with black seams. She's attractive; heavily madeup and her black bob is obviously a wig but of good quality. She falls to her knees and smiles. A faceless man approaches...

Evolving Sex Life Pt. 01

by slavecaro on Jul 14, 2020
BDSM

This story is part true but if chapters progress, it will evolve to include pure fantasy. It is about a husband and wife married for several years. The sex at the beginning is rare and boring for both. It will include many kinks but is starting out as wife humiliating a husband, denying him intercourse, and long nails. It can go a lot of places from here bec...

Confession

by holukukkar on Dec 10, 2018
Transgender & Crossdressers

Hello Everyone, This all started when I was 18 years old. Just like any other 18 years old boy I was browsing through the porn website for some porn to watch when I came across a crossdressing video in which the man was forced to wear female clothes, accessories and makeup and then treated as slave to do household chores and then fucked in ass by strapon....