Cross Dresser Stories

60,464 results
Orientation
Length
Source
Infinite Scroll

Dark Genie Ch. 01

by MaximumPotential4vr on Sep 11, 2017
NonHuman

I went straight to my room the moment I entered the house. No pit stop to the kitchen, no crashing on the couch and seeing what was on some of my favorite channels, just a beeline to my room and right onto my bed. In my opinion, there was almost nothing better than being covered in the warmth of your blankets. I was already drowsy before I got in bed so the...

College Crossdressing Confessions Ch. 04

by wifetoy on Sep 11, 2017
Transsexuals & Crossdressers

My wife's control over me insures that I have no secrets from her no matter how depraved my hidden desires. This is the fourth in a series in which I confess my past experiences as a panty thieving college cross dresser. I have changed some of the names, but the rest of the confessions are, sadly, true. Please read the first three installments for context....

Influential Factors! Ch. 02

by gummidurango60 on Sep 12, 2017
Transsexuals & Crossdressers

The alarm rang and I woke tired, thoughts of last night put a smile on my face. Finally, I don't have to hide my cross-dressing from Jill any longer. I jumped out of bed, took a shower, and toweled off quickly. When I reentered the bedroom I noticed Jill had laid out some clothes for me on the bed with a note. It read, "Prepare for a day of fun!" I had...

Virgin Beauty Nude n Bedroom Window

by Alluring_Crimson_Shifter on Sep 14, 2017
First Time

Amari a young virgin coed looked at herself in the mirror. She loved the color of her skin like a beach tan, with a slightly olive taint. Her lips were a precious natural pink. Her small dark nipples were slightly puffy with a point. Her breasts were small but firm. Her black hair matched her black pubic hair. Amari turned so she could study her side profile...

A Tale of Revenge Ch. 03

by Daniellekitten on Sep 14, 2017
NonHuman

It seemed as if I stared at that card for hours. I knew every crinkle in the cardboard, every stain on its surface. I closed my eyes and saw the cold blackness of the font which was much better then what I could have seen considering the evening I'd just had. How could I have known that the vampire would be in that alleyway? Or that she would be planning on...

Chrysalis of Kirsten Ch. 01

by kirstensubts on May 7, 2019
Transgender & Crossdressers

My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transgender slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been changed. This is who I am. A special thanks to Shy Girl Whore for her help with polishing this story!...

Changes Ch. 02

by sublocked on Sep 25, 2017
Transsexuals & Crossdressers

Notes to Reader: (1) A lot of this is fiction; much is fact. (2) Cross dressing in marriage is a difficult situation; acceptance of it comprises three entities: husband, wife, couple. (3) Nobody CHOOSES to be a cross dresser, so please don't demean yourself (the reader) by macho dismissal and criticism. Lawyers, plumbers, truckers: anyone can be one. Most...

Dressing Up For My Wife

by dirtyjoe69 on Sep 13, 2017
Transsexuals & Crossdressers

My wife and I had a bet on the football game that pitted our two rival teams against each other. It was a horrendous day for my team and hers slaughtered mine 31-0. It was the same bet we always have with each other. It is a bet where no one really loses because it ends up with us having wild kinky sex. On earlier bets we have had, she has had to let me fuc...

Chrysalis of Kirsten

by KirstenEclipse on Mar 23, 2019
Transsexual

Date: March 22, 2019 Author: Kirsten Addison Subject: Chrysalis of Kirsten Chapter 1 By KirstensubTS My name is Steven aka Kirsten. This story is about how I went from a closet cross dresser to becoming a full time transsexual slave. This story is mostly true, based on my journals with dramatic license to make it more exciting and readable. Names have been c...

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Steph's Big Night

by Leslie on Sep 1, 2017
Group Sex

Kevin had been in the bathtub since 4PM, and Leslie went to check on him. He had shaved his body, perfect for the evening to come. At this point he was just relaxing, his semi-erect cock lying on his firm stomach. Leslie couldn't help but feel aroused as she watched Kevin. She cared so much for him, and for his feminine side. They had been dating for two yea...