Crossdresser Lover Stories

78,804 results
Orientation
Length
Source
Infinite Scroll

A Crossdresser's Night In The Park

by cdtiffanymd on Oct 5, 2020
Transgender & Crossdressers

A Crossdresser's Night in the Park cd, bdsm, con, mm, anal, oral, toy Last night I was online in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with...

Sex Ed

by britneyfan on Sep 13, 2017
Transsexuals & Crossdressers

My husband and I had quite an open marriage. We were both fairly sexually adventurous and this was reflected in how we both considered it to be ok for us to be going out and sleeping around provided we were completely honest about it and came home and told the other one all about it. In fact, after a while, we found that this recounting of our bedroom exploi...

My Story of Degradation

by Philippasubmaid on Aug 28, 2018
Transsexuals & Crossdressers

A Story of Degradation. This story involves BDSM and crossdressing, change of lifestyle and full submission both mentally and physically. If this is not for you feel free to read elsewhere, please. I was 47, just divorced for the second time and for the first time in years able to be myself and enjoy what I wanted to do in my own time. I should explain...

Sarah Shared the Hot Tub and Sauna

by SarahCD on Feb 26, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more detail and corrected some...

Lauri's First Adventure Pt. 01

by stockingsofsilk4me on Feb 12, 2019
Transgender & Crossdressers

Micha and I met in the early days of Yahoo chat, when finding explicit chat rooms was easy and there were plenty of fun people online. I'm Lauri, or more formally, Lauren Carruthers, a name I chose to match my desired feminine persona. Now in my mid-40's, I've been crossdressing since my early teens. Micha and I met online and chatted for almost a year and...

Allie and Martine and Melissa

by chloevargas on Oct 5, 2020
Transgender & Crossdressers

(A Continuation of Allie and Martine) Robby, Shelly and the cop came in. Martine walked into the living room stark naked and obviously comfortable with that state. Martine and the Sergeant obviously knew one another. The cop walked over to her, the equipment on her belt jangling, and the two women embraced and began a kiss that made their bodies look as i...

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...

In from the Rain Pt. 02

by dreadknots on May 21, 2018
Transsexuals & Crossdressers

Well shucks! I got some positive feedback from the first entry, and a couple people were even nice enough to comment asking for another one! Let it be said that I'm not above placating the masses. By which I mean cute crossdressing smut. A little bit shorter than the first one, but I don't really have to introduce the characters too much this time. Don't wor...

Forced to Dress

by married40scouple on May 11, 2020
Transgender & Crossdressers

"Can I have two rum and cokes, please?" The sexily dressed, long-legged, thin brunette asked the bartender, speaking in a deep tone. "Lose a bet?" I asked the crossdresser who sidled up to the bar and order the drinks. "I don't want to talk about it." He replied in a husky voice. "At least you look real good." I smiled at him. "She dressed me up. I have...

Finally a Princess Pt. 02

by fireandlace0533 on Sep 14, 2020
Transgender & Crossdressers

Part two of a crossdresser who loves Disney who has come out to his wife while on a Disney Cruise. New experiences and adventures are ahead. Finally a Princess (Part Two) I woke the next morning around six thirty which was a little late for me. I laid in bed and thought about what had happened yesterday. I had actually spent time in front of my wife Sarah...