Indian Crossdress Stories

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Rough Rider

by bootwhore666 on Sep 16, 2017
Transsexuals & Crossdressers

After my sexcapades in Amsterdam I had such a thrill from playing dressup and just getting fucked silly. Summertime came around and I was on vacation and still in Paris. So I decided to do something similar to my weekend in Amsterdam. But where? I decided to go to Spain. I got a train ticket to Sevilla and decided I would do the same thing I did in Amsterdam...

Michele Nylons' True Stories Ch. 04

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

This is a continuation of my True Stories series, where I tell my readers about my real life adventures as a part time Transvestite. In this instalment I will tell you about my most recent encounter; my first encounter for some time, and also for me a milestone; my first time out and about dressed as a Transvestite. This is the story of my latest encounter,...

Why I Crossdress!

by readtaboo on Dec 12, 2018
Transgender & Crossdressers

Oh thank god! I hadn't heard from from him in three days and was beginning to think I'd blindsided and lost him altogether. When the phone rang, I lowered my voice to a whisper, "Patrick?...I'm home...yeah, I'd like to see you too!" More than you know. We simultaneously decided that mixing a quick drink was the single greatest idea either of us had conceiv...

What Just Happened? Ch. 03

by annie_00 on Sep 12, 2017
Transsexuals & Crossdressers

03 – Lessons I followed Beth downstairs to the living room being careful not to fall in my new marabou heels. It felt odd but enjoyable as my new breast forms were bouncing in my bra. It was also embarrassing walking around as a girl in front of my sister. I liked the security of no one knowing I liked to crossdress when I was alone, but after today, too m...

Barbie's BBC Beginning

by jacki697 on Jun 9, 2020
Transgender & Crossdressers

I had always been curious about men. I had always wanted to experiment but alas I was way too scared of being "gay" to ever follow through on any of my urges. Chalk that one up to 18 years of living in a conservative Christian community. Instead I left my sexual urges to the alone time I had to indulge in my other fantasy of crossdressing. I loved the thrill...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...

Husband's Transformation Ch. 02

by Prematurelimphubby on Jul 3, 2019
Transgender & Crossdressers

Brett woke up the next day with the sun shining in through their bedroom noticing his wife wasn't in the room with him. He stepped out of bed, put his panties from last night on and walked downstairs for coffee. He saw a note on the counter. "Good morning Britt, I had to run and get a few things from the office. I should be home soon. Take a relaxing ba...

Michele and Buster: A Tranny Tale

by MicheleNylons on Sep 14, 2017
Illustrated

This is the continuation of my True Stories series, where I tell my readers about my real life adventures as a part time transvestite. In this instalment I will tell you about Buster, an admirer with whom I have I met up with a number of occasions. I warn you now that the story contains graphic sex, use of alcohol, mild bondage, use of recreational drugs and...

Stockings & Stalkings Pt. 02

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Part II - An Unwelcome Visitor When Giselle got home she showered immediately, washing away her makeup and scrubbing at the tops of her thighs where Steve had deposited some of his seed. She had seen the whitish-silvery deposit dried on her legs above her stocking tops, which were also stained with semen. She had half a mind to throw them out as she had...