Crossdress Stories

204 results
Orientation
Length
Source
Infinite Scroll

Friends with benefits

by Kashman007 on Jun 27, 2020
Mature

Sam and Andy had been going steady for about a year now and they loved each other deeply. Both felt that they had found their soulmate. This evening they were walking back home after watching a movie with Sam’s friend from childhood, Beth. They turned into an alley that was a shortcut between the Main Street in town and the street where they lived. Although...

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The twisted DM

by Nobody567 on Nov 21, 2019
Fantasy

Authors notes: please like and comment my stuff I desperately desire your feedback and approval. I am new at this and recently redid the intro hope you like it. A being beyond space and time whose goal is to torture, torment, pleasure and change his players in ways that you cannot begin to fathom for his entertainment and pleasure. He sits at multiple tables...

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Grab Bag Transvestite Story

by MicheleNylons on Sep 16, 2017
Transsexuals & Crossdressers

I am a part time transvestite, who, if I do say so myself, looks quite attractive when dressed as a woman. It has taken me years to become adept at makeup and being capable of selecting sexy clothing that is in my size and that suits me. I have also had a number of lovely encounters with other TVs and male admirers. You can read my True Stories on this site....

Disgraced Fiancee

by rik581 on Sep 16, 2017
Transsexuals & Crossdressers

"OMG, Laura please, don't make me do this," Dave pleaded one last time as it was now time to stand before her entire family and beg their forgiveness for his sexual indiscretions. She straightened the dress he was wearing, then adjusted his earrings. "No Dave, the talk is now over. You will perform this embarrassing act for me, and ask my family to forgive...

The Woman Next Door Pt. 01: We Begin

by jableabee on Mar 9, 2020
Transgender & Crossdressers

Do not ever doubt that your life can change in a moment. Mine did. And oh so much for the better. All it took was a knock on the door. On Saturday mornings I take care of my chores: some cleaning, the laundry, shopping, the usual tasks. I'm generally done by noon and then it's time to transform myself into "Barbara", my feminine self. I'll shower, shave, do...

An influential Dare

by femboyslut122 on Apr 20, 2015
Fetish

As a college student most of Kyle's time was spent in class or doing work for class. He knew that others found a better balance, or lack thereof, between class work and a social life. Because of this Kyle always looked forward to the last Saturday of each month. He and his friends would get together once a month to catch up and dick around while playing tabl...

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Trapslut

by Alexia Wright on Aug 20, 2015
Fetish

Today is the day. Your erotic crossdressing blog videos have earned you your first practical job as an escort. Being the famous online sissy slut Annie, you used to pay the bills selling your horny pictures and masturbation videos to guys on the Internet. You got out of bed, still in your pink babydoll nightie complete with a baby blue thong and head for the...

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A Sissy Story

by PinkRebecca on Feb 21, 2020
Fetish

You always were a normal boy growing up, weren't you? Played some sports, although not to an extent where you stood out anywhere or made any teams. You had a normal friend group, as far as you knew atleast. You liked girls, like most of the boys around you, although you lacked the curage to talk to them. Well not to talk to girls in general but in a romantic...

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Miss Identified

by Dayeandknight on Sep 7, 2008
Transsexual

Your sister Sara is out of town this week at a big science convention and she has entrusted you to look after her house while she's gone. Sara has always been a big nerd when it comes to electronic gizmos and computer stuff. She’s the only one you know that could get excited over a whole week of droning lectures on astrophysics or whatever they talk about du...

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Haunting, Isn’t It?

by Dayeandknight on Apr 12, 2009
Fetish

It was a dark and stormy night, but isn’t it always with these sort of tales. The rain was coming down hard as three young guys try to make their way home. Alex, Sam, and Zack where on their way back from a swim meet that ended with them not only losing, but coming in last. Maybe the other teams where just better, maybe they need to practice more but what ev...

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