Indian Crossdress Stories

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What if...

by protoborg on Dec 5, 2015
Miscellaneous

You stand looking about yourself. There is nothing but white in all directions. Nothing but solid, unending white as far as the eye can see and probably further than that. There is light or there isn't. The vast whiteness of the place you find yourself in makes it very hard to tell. The only thing you can be sure of is that you are standing naked in a seemin...

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Chance Meeting on eBay of All Place

by Leighharding on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story of a chance meeting which has turned out to be really rather amazing and surprising. ***** I was trolling eBay for some underwear to buy when I happened on a rather large lady selling some used kit. I messaged her to ask specific sizes and she responded straight away asking if it was for me. Normally I would deny that I was buying...

The Elephant in the Room Ch. 01

by MicheleNylons on Apr 3, 2018
Transsexuals & Crossdressers

Author's disclaimer: I am not a fan of 'Sissy' stories. Some crossdressed bloke dressed in taffeta and crinolines, frilly knickers, with blonde ringleted girly-girl hair being dragged along on a leash by some leather-clad dominatrix Mistress who forces him to be her sissy, spanking him and finally sticking a big plastic cock up his arse is not my forte. Tha...

I Dress Up and Fuck My Friend Pt. 01

by tgirlchrissy on Apr 3, 2019
Transgender & Crossdressers

So last summer I was left home alone for a weekend while my parents were at a wedding. I was bored so I had my friend come over. I usually crossdress and masturbate in my sisters clothes while I have an empty house. Me and my sister are about the same size but she is curvier. She is also at college so I dress whenever I want. So me and Kyle sat around and wa...

My Sexual Fantasies

by Submissive Timmy on Sep 16, 2017
Letters & Transcripts

My Sexual Fantasies (OD Repost) I wrote this in November 2002 for my online journal on Open Diary. I'm posting this simply to have something posted. I do intend to actually write eventually. ***** I have a penis. Isn't that amazing? I also have two testicles. The flu had a stranglehold on them and killed my sex drive. But, I've since driven the flu off wi...

Jessica Find Her Way To "The Gym"

by DCJessicaCD on Sep 16, 2017
Transsexuals & Crossdressers

My name is Jessica and I've been a crossdress most of my life. I'm about 5'11", leggy and really cute. I've long reddish brown hair and I usually am able to fit into a size six. One time I got the chance to be alone for the weekend so I had to find a way to amuse myself... Didn't find any luck on the chatlines...so I got up enough nerve, packed my stuff (...

The Late Night Walk

by Lovinhose on Sep 16, 2017
Transsexuals & Crossdressers

This story is fiction. It did not happen...but I wish it would. It's been a while since I've written anything, but as it's been a while since anything real has happened, I wanted to add another story to my 'collection'. Thank you all who've replied with positive, encouraging words. This is for you. One more little 'disclaimer'...this story is a fantasy about...

Crossdress Flash Adventure

by iwant2suckabig1 on Sep 16, 2017
Transsexuals & Crossdressers

My job involves a lot of travel which lends itself to keeping the risk of this kink as low as possible. I'm often in strange cities where no one knows me. This particular experience took place on a visit to a city in Southern California. My hotel was in an affluent section of town but during my exploration of the neighborhood I discovered that there was a l...

Dorm Floor Bitch v. 04

by GirlyCumslutBoy on Sep 16, 2017
Transsexuals & Crossdressers

CONTINUED FROM DORM FLOOR BITCH V3 After that night, when I had gone into the guys room and he had fucked my ass, I had an inspiration. I had laid under his bed, cum leaking out of my asshole, my own cum coating my chest, as the guy who had just fucked me rammed his cock into his girlfriend. I found it so erotic, I had almost passed out...her moans of pleas...

Encounters of a Crossdressing Slut

by KAshton on Sep 16, 2017
Transsexuals & Crossdressers

This is an introduction to my crossdressing experiences, touching upon highlights along my journey. I will write more about these, and other encounters in detail, in time. These really are all true stories, no embellishments whatsoever. I had always been fascinated with women's clothing, specifically tights (pantyhose) and anything silky and sheer, like sli...