Crossdress Brother Stories

44,291 results
Orientation
Length
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Infinite Scroll

Caught My Husband...in Lingerie

by TheGenderBender on Sep 16, 2017
Transsexuals & Crossdressers

I had been away on a spa weekend with my girly friends so was going to surprise my husband by arriving home 4 hours early. He had been so happy for me to spend two nights in a luxury spa hotel I had to repay him the favour, and I knew just how to do it. I crept slowly into the house, and by the sounds of it he was upstairs in our bedroom, probably doing som...

Caged!

by yvetteinpanties on Jun 19, 2018
Transsexuals & Crossdressers

I was a late blooming sissy. Like most sissies-to-be, I had early incidents of trying on my sisters clothes and enjoying the way they felt, but I always viewed myself as a heterosexual who just liked to imagine stroking a nubile female underneath the lingerie I was wearing. It was much later in life that I took the serious turn from being a heterosexual cros...

Sissy Academy

by Cynthia Sissy on Jan 2, 2019
Transsexual

(feel free to message me about anything! I'd love to hear from my readers :)) The alarm beeps away as you groan at the sound of it. A cool breeze rustles the curtains, letting the sun peek through. Pushing your hair to one side, you check the time. "Oh, it's still early," you say, pushing the sheets away to reveal your blue satin panties and chemis...

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Curse of the Living Clothes

by calx86 on Jan 8, 2020
Fantasy

There are several stories out there involving living clothes but I want to leave this open to allow many collective authors to be as creative as possible. For example, you can write a story about clothes simply coming to life and stripping their wearer, leaving them nude and embarrassed or maybe the living clothes forces someone to wear them and turns them i...

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Relax

by BoredTBDL2 on Jan 7, 2021
Fetish

“Jesus man, that’s a lot.” Mike stared at the old metal table between you two in the middle of his backyard patio for what felt like several minutes. You couldn’t blame him for taking his time though; you two were just gonna meet up for drinks, but the alcohol had other plans, and now you feel like you need to pay your friend for being your therapist. “I don...

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Just a Normal Couple

by Feinux on Sep 25, 2018
Transsexuals & Crossdressers

To the untrained eye we look like just another normal couple walking down the street. Beautiful girl with a handsome guy, both smiling and laughing, holding hands with each other. But if you were to look a bit closer you would realise not all is as it seems. You see, my name is Paul and I am the beautiful girl. My girlfriend's name is Sarah and she is the ha...

Lingerie Does Make the Man Ch. 02

by lingerielover on Sep 16, 2017
Fetish

If you had read my last story you would know by now that I love to wear women's lingerie. I no longer wear guy underwear except when I go to the doctor, I only wear panties. It doesn't matter what type of panties as long as they are either silk or lace, no cotton ones for me. My wife is some what supportive, but she doesn't fully approve either. We have been...

Stockings & Stalkings Pt. 02

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Part II - An Unwelcome Visitor When Giselle got home she showered immediately, washing away her makeup and scrubbing at the tops of her thighs where Steve had deposited some of his seed. She had seen the whitish-silvery deposit dried on her legs above her stocking tops, which were also stained with semen. She had half a mind to throw them out as she had...

Life and Time of Lady Vargos Ch. 01

by rik581 on Oct 3, 2018
Transsexuals & Crossdressers

I am in the process of reposting my stories. *** "The Life and Times of Lady Vargos" is the second book of the Martin Hastings adventures into a life of forced feminization. This story follows the feminization and marriage of a reluctant young man as he is forced to accept his fate as a male/bride, in a same sex marriage, arranged by his family. This stor...

A New Direction Ch. 01

by MyUncensoredSelf on Sep 15, 2017
Transsexuals & Crossdressers

I was nervous when I texted my wife that morning. She'd gone to the shops and I asked her to buy me some nylons. She knew I liked to crossdress and we'd even fooled around once while dating with me in a leopard print stretch leotard and my breast forms. She'd loved it that time and it was one of the horniest weekends we had together. But since then things ha...