Halloween Crossdress Stories

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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...

My Sister's Boyfriend

by KinkyPotato on Sep 13, 2017
Transsexuals & Crossdressers

I never considered myself to be gay or anything like that, but my first time was with my sister's boyfriend. It happened a week ago now. I was at home alone, parents away on vacation, and my sister gone on business. These times were fairly common, so I would use them to indulge in a little habit I had. I liked to crossdress in my sister's clothes. Nothing se...

Secret Lives Pt. 01

by WildDaisy85 on Dec 12, 2017
Transsexuals & Crossdressers

This story is completely fictional. All characters are willing participants in all activities and similarities between other fictional characters is unintentional. I hope you enjoy the story and welcome all feedback. This is my first time writing so expect there to be a few mistakes. Thanks and I hope you enjoy reading this story as much as I did writing...

Alone Time

by bullockhall on Sep 14, 2017
Transsexuals & Crossdressers

I walk up the steps of the old Victorian house where I live and slide my key into the lock of my door. I smile. It is Saturday. My day. The day I get to dress up, explore my feminine side. I enter the house and drop my keys into the bowl by the door. My roommate, Jack, walk into the living room with a sandwich and a beer. He picks up the tv remote and sees m...