Crossdresser First Time Stories

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Infinite Scroll

How I was Forced Out of the Closet

by gtanya on Apr 4, 2018
Transsexuals & Crossdressers

I was again dreaming of the night I would lose my anal virginity. It had been such a constant since last 3 weeks. I had been talking to a beautiful CD named Rachel since last 6 months and with the thought of meeting her in person, I had planned a vacation to China where she was living. The only problem that I had here was I was going to be on the vacation wi...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

What Just Happened? Ch. 02

by annie_00 on Sep 12, 2017
Transsexuals & Crossdressers

02 – Am I a pervert? When we got home it was late in the afternoon. We had been gone all day, first to the salon, then shopping, lunch, drinks and the crossdresser store. I was tired but felt very sexy under my clothes. I did not want Beth, my step sister, to know that I totally enjoyed the experience today. I thought that she would think I am perverted. A...

Rest Stop Romance Ch. 01: Pilot

by Dark_Rose90 on Sep 15, 2017
Transsexuals & Crossdressers

~The following is entirely fictional and just a fantasy of mine. Any likeness to actual persons or events is unintentional and coincidental. Also, this is just a Pilot. If the story gets enough positive feedback, I'll continue it on a regular basis.~ My name is Rosalie or just Rose for short. At least it is when I'm dressed up like a 20 year old college gi...

Sarah Meets a Friend

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I posted a listing on Craig's List for a "cum buddy". I explained that I am a crossdresser and that I wanted to find a regular sex buddy. No commitment, just sex. I love to get on my knees to give a blow job. I had several replies. One was local and sounded promising. I don't rush into meeting with a total stranger. First I always exchange a few emails and m...

Dad My First Lover Pt. 01

by sarahchica96 on Sep 16, 2017
Transsexuals & Crossdressers

Introduction I'm Sarah a 20 y/o closet Bisexual crossdresser, 5ft 6 , slender body I achieved by working out a bit. I love dressing up in short skirts, dresses, heels, typical lingerie and I have a fetish for the Naughty Secretary look. Main story starts here I had come back home from college for the winter holidays. It was just dad and me at home since...

Crossdresser Crosses Over for Good

by TVTrishCD on Jun 8, 2020
Transgender & Crossdressers

I certainly allowed myself be conned! So, I had a problem with my turn signals on my car back in early January. I was pretty sure it was the turn signal switch, but not sure. There is a site where sex ads are very prevalent. In the CD section it's mostly hispanic, and oh do the latino boys just LOVE us white cd's!! They are very relentless in their pursuit o...

Crossdresser Evolution Ch. 06

by pantyhigh on Aug 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's panties. Recap - Crossdresser Evolution - Ch 02 - Getting my wi...

Parking Area 2 Miles

by Lovinhose on Sep 15, 2017
Transsexuals & Crossdressers

Prior to writing this next installment in my awesome sex life as a bisexual crossdresser, I thought I had already written about all of my worth while, true life experiences, but I had actually forgotten about this one. It happened in, I believe, 2008, during the end of the summer. I was driving my truck. I am a truck driver by trade. Three hours and a co...

Sarah Meets a Buddy

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

I posted a listing on Craig's List for a "cum buddy". I explained that I am a crossdresser and that I wanted to find a regular sex buddy. No commitment, just sex. I love to get on my knees to give a blow job. I had several replies. One was local and sounded promising. I don't rush into meeting with a total stranger. First I always exchange a few emails and m...