Crossdress Stories

204 results
Orientation
Length
Source
Infinite Scroll

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...

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...

Biker Bitch Ch. 01

by MicheleNylons on Dec 21, 2017
Transsexuals & Crossdressers

Chapter One: Cassie Cassie woke up feeling hungover, hungry, thirsty, beaten and abused. She was still chained to the billiard table in the Beasts of Burden Motorcycle Club clubhouse. She rubbed her ankle where the chain was manacled to her leg. Her nylon stocking had worn through and her skin was red and bleeding. Had it really been four days? Cassie s...

A Wife A Little To Understanding

by felicia_rene on Oct 12, 2020
Transgender & Crossdressers

Present day: We arrived at the 'Sissy Salon' which was a covert sex club for downlow gay wealthy men and lesbians. As his agent and pimp I collected all his performance fees. I walked into the 'Sissy Salon' to make sure that everything was in place so my sissy husband could perform. Then I went to his dressing room to make sure everything I requested for me...

A Dress Up Party with the Girls

by bigrusker on Sep 12, 2017
Group Sex

I stood there in the mirror, contemplating what I was about it do. Do you have what it takes to do this? I asked myself. At this point, it didn't really matter. I could hear the four giggling girls downstairs and despite only having arrived a few minutes ago I knew they had started the party quite a while ago and had already had a fair amount of wine. But t...

Lady In The House Ch. 12

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

"Hang on a minute Carmel; I've got an idea," Steve exclaimed and sauntered over to where I lay curled up in a snivelling ball, may face covered in semen mixed in with my heavy makeup; my clothes dishevelled. "Lift that bitch's face for me," he said as he played with his cell phone. Carmel came over and helped me to my knees. I knelt there with my face hung...

Inaugural Crossdress Sexfight Ch. 04

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

The league's first tag team match featuring another newbie. Participants Dani Davis (me): Record 1-3 Jamie Play: Record 1-0 vs Dani Delights: Record 1-1 Mandy Spencer: Record 0-0 After hearing about our club, I was approached by a new gurl, Mandy, who had the body to fit right into our league. She was a rookie, but was interested in a tag team match after...

Secret Lives Pt. 03

by WildDaisy85 on Jun 19, 2018
Transsexuals & Crossdressers

This is a continuation to Secret Lives Pt 2. I highly suggest reading the previous chapters as they set the stage for this part. This part is more of a development chapter and some readers may find it lacking in the sex department, but I feel it is important to the overall tone of the series. I appreciate the feedback and please keep it coming. I am also lo...

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....

Kasey's Confession Ch. 14

by KaseyLegs on Sep 14, 2017
Transsexuals & Crossdressers

Lying in the hospital bed, hooked up to monitors and who knows what else, I just stared out in shock. It was to be expected, they said, as they explained I had been in a coma for a very long time. What they did not know was that the source of my confusion ran much deeper than just waking up disoriented after a long time "away." I had absolutely no idea who...