Indian Crossdress Stories

8,976 results
Orientation
Length
Source
Infinite Scroll

Inaugural Crossdress Sexfight

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

Hi everyone and welcome to the Crossdressers Sexfight League (CSL). My name is Dani and I'm the primary author as well as a regular participant in the league. The league title says it all. It's an erotic sexfight wrestling league for crossdressers of all ages where the loser is forced to service the winner of each match. It takes place in living rooms, bedr...

Young Crossdress, Meets His Daddy

by Sliver02 on Sep 1, 2017
Transsexuals & Crossdressers

Well I am 28 year old male, not in best of shape. I can still run a mile in under 15 minutes, and I work 3 to 4 times a week. I try to stay in shape a little bit. Well that is enough about my physical appearance. I am also married to very beautiful wife, who I love more then the world. We have very open marriage, but there are few things she does still not k...

That's What Friends Are For Ch. 03

by TurningintoCD on Sep 15, 2017
Transsexuals & Crossdressers

I didn't know what to do about David. He was my best friend and after years of teasing me, he had opened up a pandora's box of getting me to crossdress. Now I'm supposed to go as his date, as Angelina Jolie, but the host of the party, Ben, a real gentleman, wants me too. I wish I could be Ben's date, but I don't know how to escape from David's grip. "Alliso...

The Project Pt. 01

by Chloecrownofthorns on Sep 16, 2017
Transsexuals & Crossdressers

Dee's bedroom lit with a dim blue glow from her smart phone. Her nailed finger swept up the screen as she scrolled the strictly platonic listings. "Boring, boring, spam, fake. Can anybody complete a sentence on here!?" she thought. She was just about to give up when she read the headline, "Mess around with gender roles..." As she read the post, she smirk...

Seducing Jay at a House Party

by vhunt on Sep 16, 2017
Transsexuals & Crossdressers

Ann seemed pretty happy with the party she threw for her birthday. People were mingling in her garden, talking and laughing while they fought summer's heat with beer. I didn't know many of Ann's friends - in fact, the only face I recognized at the party was her own, but I knew she kept company with mostly single people and any of her gatherings resembled mor...

Learning to Crossdress Pt. 04

by crossdressme70 on Sep 15, 2017
Mature

I was now totally dressed, in 4" open toed sandals, with black seamed fully fashioned stockings attached to the garters of a tight fitting waist cincher, wearing an underwire long-line support bra with "Pad inserts" that pushed to give me a cleavage. My makeup was incredible, with blue eye shadow, long eyelashes, and heaps of lipstick, and I was wearing a...

Learning to Crossdress Pt. 01

by crossdressme70 on Sep 15, 2017
Mature

I am a "Closet-Crossdresser" - something my wife would not accept, but a secret I indulge in whenever she is out of the house for a while. This is my story of how a beautiful older lady, who had a "fetish" for lipstick, nylons, high heels, and lingerie, introduced me to the pleasures. It was the late-1980's, we had just moved from a small town in the UK, t...

Barrack Room Betty Ch. 02

by MicheleNylons on Oct 8, 2019
Transgender & Crossdressers

Chapter Two – Wren Division Ho! The four Leading Recruits were hungover and hungry and in the grey dawn and cold bleak light of day they weren't sure that their prank was really worth it. They entered the cabin and found the four 'Wrens' stood at attention and immediately began to break down in laughter. "Of my fucking god you guys look stupid!" Jean Burge...

Girls Club Ch. 01

by ValerieMay on Mar 7, 2018
Transsexuals & Crossdressers

I stood by the bedroom window, letting the morning sun shine bright lines across my face. I closed my eyes and inhaled deep through my nose as the hazelnut flavored steam from my coffee reminded me of when everything was so ordinary. Ken was still in the shower and I wondered how he would like seeing me in my new XL knit sweater without any pants or underwea...

Inaugural Crossdress Sexfight Ch. 03.5

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

After losses to Tommi, Jaimie and Dani, it didn't take a genius to realize that I had become the defacto jobber of the Crossdressing Sexfight League (CXSFL). There wasn't a cock among them that hadn't been in my mouth or ass at some point and if we had kept standings, I would have been in dead last place. Unless I wanted to accept my jobber role within the l...