Crossdressing Wife Stories

121,758 results
Orientation
Length
Source
Infinite Scroll

A Wife's Surprise

by Aprilsdays on Jul 3, 2019
Transgender & Crossdressers

April's Amazing Day So, my story starts like most of us crossdressers, finding moms lingerie in the clothes hamper as a pre-teen and of course putting things on while getting those first feelings of excitement, sexiness, and that surge of adrenaline. Every day I became consumed with hoping against hope that when I arrived home, no one would be around so tha...

Jailhouse Faggot

by nancyvasquez on Oct 14, 2017
Anal

Before I got sent to the joint I spent over 6 months in county jail. The jail was old and they had old fashioned cells with bars. The cells were small, 4 bunks in each cell. I had never been in jail before and I was scared and it showed. I was young, slightly built, and timid as hell. The cellblock I was housed in was on the 4th floor. There were two sides...

Best Camping Trip Ever Ch. 01

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

*This is a fictional work based on a fantasy of mine. Hope it comes true, and hope you enjoy.* ***** I love camping! I mean I really love camping. I also love crossdressing. And sex. With men. Yeah. I live for all the above. I have also begun to get a little more bold as the years go by. I wear tights or pantyhose under my jeans everyday, even during the s...

This to Keep Me Quiet Ch. 01

by MicheleNylons on Oct 5, 2020
Transgender & Crossdressers

Chapter One - It's Not Right Uncle John, For All Sorts of Reasons Author's Note: This is a little two-part tale similar to my early stories. It has all the trappings of a Michelle Nylons story: a little incest, a little blackmail, a lot of sex and a surprising ending. I hope you like it. Crystal Palace sat at the bar watching Melanie Starr singing The Cryi...

Special Girls

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

We get together every Thursday at lunch. Our friend Emilio loves having us, tells us we add some glamour to the place. His little restaurant is popular enough that we're lucky to have a standing reservation for luncheon late in the week. Should one of us be absent, we buy her meal and wine anyway else Emilio glare at the empty seat. Ricki is our waitress, a...

Rm 209: First Sex as a Crossdresser

by MelissaMwaz on Sep 16, 2017
Transsexuals & Crossdressers

This is a TRUE STORY. I've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a kid and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-...

Adventures after Dark Ch. 01

by classmate1119 on Sep 16, 2017
Transsexuals & Crossdressers

-Author's note- I started crossdressing in my teens, but coming from conservative South-east Asia, it was definitely my darkest secret for many years. I would often dress in my mother's dresses, and put on her makeup when I was home alone, but I stopped crossdressing when I moved away to start college. When I won a scholarship to study in the UK, I did no...

Erika's Story Ch. 03

by Quantarx on Jan 22, 2020
Transgender & Crossdressers

This is the third part in Erika and Mary's widening exploration of crossdressing, if you have not read the first couple chapters I encourage you to go back and read those first. also, thanks for the feedback I have received and please continue to rate and leave feedback and comments so I can continue to evolve as a writer. *** I lay in bed with my loving...

Secret Lives Pt. 01

by WildDaisy85 on Dec 12, 2017
Transsexuals & Crossdressers

This story is completely fictional. All characters are willing participants in all activities and similarities between other fictional characters is unintentional. I hope you enjoy the story and welcome all feedback. This is my first time writing so expect there to be a few mistakes. Thanks and I hope you enjoy reading this story as much as I did writing...

Kasey's Legs

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

I had been crossdressing for close to ten years. It started as a Halloween costume gag where I shaved my legs, put on a cheerleader outfit and wore a scary mask. After I kept getting compliments on how good my legs looked I continued shaving them and experimenting with dressing in a variety of women's outfits, skirts, high heeled shoes, panties and bras. It...