Crossdress Brother Stories

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Inaugural Crossdress Sexfight Ch. 02

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

CXSFL – Match 2: Dani vs Jamie With my first match under my belt, albeit a humiliating lopsided loss, I felt better prepared and even more excited to try another match. I was hoping to be on the giving end for my next match and felt I had learned some valuable lessons that would increase my chances of getting a win. Although it's difficult to complain about...

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

Lady In The House Ch. 14

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

After the warden left my cell my mind was racing. Why were they bringing my sister here to visit? How was I going to remove my makeup and nailpolish? What was I going to do about my semen-stained clothing? I heard the keys rattle in the lock of my cell door and Steve strolled in. "Well Michele it look's like you are starting to behave. The warden seemed ha...

Magic Panties Ch. 03

by nolfon1 on Sep 12, 2017
Transsexuals & Crossdressers

This story is a work of fiction, all characters are fictional and obviously the events are fake. You may reprint this as needed, just give credit to the author. If any differences occur between continuity, accept the one you like better as truth, and enjoy! * For those just joining us, let me recap, my name is Rachel...er, Roy, yeah let's go with Rachel, a...

My Chastity Story Pt. 01

by Digger66 on Oct 3, 2018
Fetish

[Massive re-write of this story. Good feedback. I flushed out the character's motivations.] * It all started because I jerk off too much. Every night, I would retreat to the basement after my wife, Kate, would go to bed early. Both of us are in our mid-forties. I often asked for sex, but my wife complained that I was never any good at it. She always said t...

Maid to Order Ch. 03

by MicheleNylons on Oct 13, 2020
Transgender & Crossdressers

Michele lay on her bed sobbing. She felt confused and defiled. Michele's alter ego Mick had spent many years in the army, he knew how to fight and would never allow himself to be coerced or forced into doing anything he didn't want to. But when he transformed into Michele, all of his resilience training and self-defence mechanisms seemed to have disappeared...

How I Became Sissy Willow Ch. 02

by willow619 on Sep 12, 2017
Transsexuals & Crossdressers

"Now the preliminaries are over, and it's time for the entertainment part of our evening!" That was what Fern, my wife, said to me as I lay on the bed after I had been fucked by our newly mutual lover, Jason. I was dressed in pink panties, bra and slip, and a floral sundress. A blonde wig with long curls was on my head, completing the transformation. Fer...

Barrack Room Betty Ch. 04

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Four - A Night at the Flicks Michele was confused; she didn't like Leading Recruit Jason Jones one bit, he was a bully but he was also handsome, strong and actually quite intelligent. She knew he had a thing for her as soon as the Leading Recruits made the grommets crossdress, and of course last night he had ejaculated in his pants when he was span...

Inaugural Crossdress Sexfight Ch. 03

by danidhotcd on Sep 16, 2017
Transsexuals & Crossdressers

The third match of the season matched me up against another rookie that shared the same name as me. Dani had read my stories on the internet and enjoyed some of my photos on Flickr and wanted a match with me. I guess it would seem pretty enticing as I'm sure he was noticing that I was seemingly now a jobber. I had seen Dani's photos on Flickr as well and we...

A Weekend Getaway To Crossdress In

by crypticguy143 on Sep 13, 2017
Transsexuals & Crossdressers

Hi All, I am 32 years old married guy without any children living in California. I believe I have had the bisexual urges since my early childhood. But I somehow developed a new fantasy to cross-dress in last couple of years. Since then I have been thinking about it pretty much all the time and been trying to explore it. Couple months ago my wife went out w...