Crossdress Brother Stories

44,291 results
Orientation
Length
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Infinite Scroll

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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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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New Student (CMNF/CFNM)

by ewong on Apr 1, 2021
Exhibitionist & Voyeur

Avery Williams sat in the Dean's office. It was 9 in the morning on Sunday. Classes would begin the following morning, and having arrived a day late, Avery missed out on all the orientation presentations. "It's nice to meet you in person, Avery. How are you this morning?" The Dean asked. "Um..fine I guess?" Avery replied. "Good. Now,...

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Stuck at an All Girls Reform School

by Therock99 on Jul 12, 2018
Fetish

"John Doe to fit in with normal society, you have been sent to a reform school to make sure that your troublemaking ways are dealt with before they get out of hand. As normal failure to go to the pick up point for your school will result in a warrant being issued and a ten year jail sentence will be issued to you. We understand that this may seem unfair...

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Die Mädchenschule für Jungen

by Redboom on Feb 12, 2020
Transsexual

In einem kleinen Café: Verträumt blick Leon in den großen Spiegel auf der anderen Seite des Raumes. Das Spiegelbild zeigt zwei Damen in den Enddreißigern, eine junge Dame Anfang zwanzig und ein hübsches Mädchen gerade achtzehn Jahre alt geworden. Zumindest sieht sie aus wie ein hübsches Mädchen: Eng anliegendes dunkelblaues Chiffonkleid mit locker über die S...

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Princess of Lustria

by Amylili on Feb 7, 2021
Fantasy

The great holy kingdom of Lustria is a large and prosperous nation, freshly victorious of a long lasting war against the forces of the Shadowlands where it set itself as the most powerful force of the northern continent. Its capital Lewdale, was founded centuries ago at the merging point of two large rivers and became a growing center of trades. From his fam...

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Lady In The House Ch. 12

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

"Hang on a minute Carmel; I've got an idea," Steve exclaimed and sauntered over to where I lay curled up in a snivelling ball, may face covered in semen mixed in with my heavy makeup; my clothes dishevelled. "Lift that bitch's face for me," he said as he played with his cell phone. Carmel came over and helped me to my knees. I knelt there with my face hung...

Sissy life

by Kaori_chan on Jan 21, 2021
Fetish

So Ive always had this fetish. I love wearing panties. My name is Jake and Im a twin with my sister Jane. Ever since I was young I would sneak into the laundry room and wear my sisters panties. Being twins, we were always around the same size. She always had the cutest underwear. It was pink, frilly, and sometimes had cute designs all over them. My fetish de...

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