Crossdress Brother Stories

44,291 results
Orientation
Length
Source
Infinite Scroll

Dream Prom Date

by Zelonkarac on Sep 26, 2017
Science Fiction

It is that time of year again, Prom season. But this year is different, this is the Senior prom that will change everything. Sadly the only thing missing for someone is the actual prom date. Who is the protagonist or victim? (Dear reader, as you read this story please remember that if you like any of the chapters that you read please take a second to click &...

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Forced Crossdressing Stories

by Dayeandknight on Feb 1, 2018
Transsexual

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't yo...

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Internship

by nimt on Jul 12, 2018
Transsexual

An internship was compulsory as you approach the final year of your high school. The school believes in providing students with the opportunity to gain valuable practical experience by learning from the industry of tomorrow directly. You went for several interviews and only successful candidates get notified. In the events that the none of the companies pick...

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Second life of Emily

by Alexia Wright on Jun 3, 2015
Fetish

I have always wanted to get fucked by another man. Being 5'6" and weighing little over 60 kilos, my effeminite and near hairless body bore no signs of an able bodied alpha male, so i decided to explore my inner girl since my mother and sister are the only people i live with. It started with simple things, like my sister's school clothes, then her under...

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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...

Girls Club Ch. 01

by ValerieMay on Mar 7, 2018
Transsexuals & Crossdressers

I stood by the bedroom window, letting the morning sun shine bright lines across my face. I closed my eyes and inhaled deep through my nose as the hazelnut flavored steam from my coffee reminded me of when everything was so ordinary. Ken was still in the shower and I wondered how he would like seeing me in my new XL knit sweater without any pants or underwea...