Crossdress Brother Stories

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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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Taste of Temptations

by satoshy12 on Sep 29, 2020
Fan Fiction

The Sinful Tastes This is the tale of Prince Arlan Baratheon. Arlan Baratheon is the Son of Cersei Lannister and Robert Baratheon, with the classical Baratheon bright blue eyes and the Lannister Golden Hair. He was a normal person who had landed in Westeros and with defective magic he had just enough control about his magic to increase his reflexes, strengt...

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Confiding in My Hairdresser

by Leighharding on Dec 19, 2018
Transgender & Crossdressers

I've always had a great relationship with my hairdresser, Mary. She'd been cutting my hair for years and we probably shared a few more details than we should about sex, she made me laugh at some of the naughty stuff she'd been up to! On occasion around a year ago, she came to the new house that I'd just moved into with my girlfriend to cut my hair. The cha...

A temporary wedding

by Amira on Apr 22, 2025

Amira was fiddling with her niqab, which was constantly getting caught by the wind. She still didn't like to wear it, as the black garment blocked her vision. She could see only through a tiny slit, unlike the hijab she more preferred. But she was forgetting more and more that she wore it after some minutes. Now outside, Ahmed pointed out that she had to use...

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Learning to Crossdress Pt. 02

by crossdressme70 on Sep 15, 2017
First Time

Since relating my "First Experience" to you, I have been re-playing it over and over, in my head, and realise how fortunate I was to meet a lady who wanted to indulge her fetishes with me, and established my desire to crossdress. As I left off, she had me wearing her silk panties, with her kneeling across me, my hands sliding up and down under her half slip...

Sissy Truth or Dare

by BimboBarbie on Dec 23, 2017
Transsexual

You wait nervously outside the front door of Samantha's house, your heart pumping as you still can't quite believe your luck. Just a small, nerdy guy like you being invited over to the most popular girl at school's house! Finally gathering up the courage as you tentatively press the doorbell, hearing the sing song chime through the door. A whole minute passi...

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Fulfilling all My Fantasies Ch. 01

by classmate1119 on Apr 23, 2019
Transgender & Crossdressers

"Last chance to change your mind, Cristi," Jalen said. "It's probably the most outrageous one so far! Not that I'm worried, of course, but you never know what else might happen... " I reapplied my lipstick in the reflection of the club's glass entrance. "Hey, we spent too much time preparing for this. Don't back out on me now, Jalen!" I threw him a coy smi...

Barrack Room Betty Ch. 03

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Three -- Michele's Story The four Wrens of Collins Division woke at 'call the hands' at 0640. Doris had got out of bed at 0600 to prepare breakfast and was in the galley. She'd tried her best to do her makeup and dress like a Wren but she still looked like a 'scranbag'; not that it mattered, in the steam filled, greasy kitchen. Her hair was matted...

Vacation with Aunt

by Alice Dragonslayer on Mar 19, 2018
Transsexual

Hello, you are 18, semi long black hair, feminine build, shy and submissive. You visit your Aunt Katy (looks like Katy Perry) for the summer. She may or may not have a daughter. She has a very feminine house and has a pink car. She dresses pretty hot. Her breasts are perfect and she's in her 30's. She doesn't have a husband and stays in an apartment with one...

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Summer at Auntie's

by BimboBarbie on Dec 18, 2017
Transsexual

You stumble off the plane and into the airport with your legs feeling like jelly having been seated for a few hours, heading down to the conveyor belt to collect your suitcase. Watching as a few familiar people you recognize from the flight all come and go, collecting their bags happily and leaving while you remain growing increasingly worried. Eventually it...

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