Cross Dresser Stories

60,464 results
Orientation
Length
Source
Infinite Scroll

My Accidental Orgy

by usmclass on Sep 16, 2017
Transsexuals & Crossdressers

If you don't enjoy stories about oral sex, transwomen, sissy sex, or orgy situations, then you need to check out the Reader's Digest website, because that's all here, and a bit more. ***** Hi! I'm Cassandra. Growing up in the 60s and 70s (in an Alaskan logging camp no less) I became very familiar with men's magazines and Penthouse Letters. Before I move...

Slip into Ownership

by Confusedjerry on Dec 25, 2018
BDSM

I wrote this originally just for me to document and understand my slip into the total loss of control of my own life and being owned body and mind by one person, my Mistress. However I have decided to publish it, please bear in mind this is 100% true and is a work in progress. If I get a good response I will add to it as I write it. *** For her protection...

Three Day Husband

by suegsusan on Sep 14, 2017
Loving Wives

Margaret and Jim had been married for ten years and their sex life was almost non-existent. It had never been very thrilling at the best of times. Despite this, they have a pretty good marriage. They love each other and they really care about each other. There's something you need to know about Jim. He is a closet cross dresser. That is, He gets a great dea...

Hot Sex Instead of Dancing Ch. 17

by SusanJillParker on Sep 16, 2017
Fetish

Please give me the support of your vote. * Walter shows Tiffany his extensive women's shoe collection. "I'm sorry I mentioned my stripper clothes," she said with sadness. "Maybe some other time. I'll bring out all of my bras and panties for you to see them, touch them, and sniff them another time," she said with a laugh. "Okay?" No doubt she was kidding...

Halloween Cross-Dressing Bash Ch. 06

by BOSTONFICTIONWRITER on Sep 14, 2017
Transsexuals & Crossdressers

Gloria left the store in the capable hands of her store manager, Sharon. After paying for his purchases, with Gloria giving Bob a very generous and unexpected 20% discount, Bob followed her car home in his pickup truck. He was just as excited to maybe have a sexual affair with her as he was with the thoughts of trying on the clothes he just bought. They sto...

Cross Dresser Dominated Ch. 01

by johnfell69 on Sep 16, 2017
Transsexuals & Crossdressers

I never knew his name. I did remember him, however. He had the thickest cock I have ever seen and probably will ever see. To say it was beautiful was an understatement. It was majestic! Let me backup to the ad I placed on the internet. Where do I start? Well, I have to confess to everyone my deep desire, no, my deep fetish, about wearing women's clothing....

His Sissy Bitch Ch. 01

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

It started after a transvestite walked into the bar. Sounds like the start of a bad joke but it's not, we were in a party bar after work, me and my boss. My boss and I were having a drink after work; he was more than a little high. An obvious cross dressed man with several friends came in and sat at the bar. 'She' was very cutely dressed, stylish and sexy. M...

Diary of a Cross-dresser Ch. 01

by Adikon79 on Sep 16, 2017
Transsexuals & Crossdressers

This story is based on my own personal experiences and any comparison or similarity to anyone else's story, experiences, or copyrighted material is purely coincidental. This story contains adult material and language and should only be read by those legally permitted to do so. The story within is the copyrighted material of the author and should not be redis...

Influential Factors! Ch. 04

by gummidurango60 on Sep 16, 2017
Transsexuals & Crossdressers

The next morning I awoke wondering why I was still in my dress. I looked at my cell, which I also used as an alarm clock, and it was all ready eleven am. I thought for a second... and figured if I was still in my dress I was still in makeup. I got up, sat at my vanity and cleaned up my face then got up to go take a shower. My cell began to hum; it was a text...

Meating Samantha

by Funnbunnies on Sep 16, 2017
Transsexuals & Crossdressers

It had been almost two years since my first experience with Dave. That was the first time a man had sucked my cock. It was the first time I had touched another cock and the first time I had sucked a cock. That day was the birth of a new me. I no longer was a homophobe. Although, I did not look at men the same way I looked at women. I did not lust after them....