Crossdressing Friend Stories

142,454 results
Orientation
Length
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Infinite Scroll

Sarah Helps Clean Out a Garage

by SarahCD on Mar 11, 2019
Transgender & Crossdressers

A friend of mine, Sandy, asked me if I would come over next Saturday and help her clean-out her garage. I had known her for several years and her husband had just left her and so, when she asked me for help, I could hardly refuse. In addition, she is cute and I cannot imagine why her husband would leave her. On Saturday, I went to her house. I only ever we...

Fetish Life

by Kinkyguyohmy on Apr 20, 2020
Fetish

You wake up just as the alarm on your phone blasts a corny jingle right into your ear. You lazily stretch, pull your covers off your body and slowly rise from your bed. You meander over to the mirror that hangs on your door and look at your reflection. A teenage boy with light brown hair, glowing grey eyes and an average build stares back at you. You smile....

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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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Your Waitresses

by weluvhose on Sep 15, 2017
Transsexuals & Crossdressers

We have not submitted anything for almost a year as daily life as certainly been in the way for ALL of us. My wife and I decided this one would be a slight change to the previous submissions. It is all fantasy but we both would enjoy bringing this one to "true" life if ever possible. Enjoy and we always welcome any comments!...

Sweet Alice Returns

by Akito01 on Sep 13, 2017
Transsexuals & Crossdressers

After the night I previously described to you with Sweet, it naturally occurred to me to wonder if he had seduced other men in a similar manner. It may seem silly or naïve, but I honestly had no idea. With some sly delight, this is story Sweet told me. Naturally, to preserve the identity of all involved, I will continue to refer to Sweet as exactly that. He...

Men and Women Cannot Be Friends

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

"If this is what you want," she said, her tone even and controlled. I could tell she was disappointed. Perhaps she'd dreamed of a relationship or she'd fantasized of an emotional connection with me. She'd never hinted or remotely seemed interested. I thought she was happy with being friends. My few fumbling attempts to offer something more were rebuffed po...

The Bio of a Masturbator

by Chatomana on Sep 18, 2017
Toys & Masturbation

Disclaimer: Although this is a work of fiction, some parts contain actual facts and events. The author can not and will not be held responsible for any injuries that may occur if the reader tries to reproduce of these events. The author holds all copyrights to this story, printed and/or digital. Prologue This story is not about love, nor about romance, or...

Stockings & Stalkings Pt. 01

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Giselle applied the clear topcoat to her ruby-red lipstick; she pursed her lips as she looked at her reflection in the mirror. "There; finally finished," she smiled to herself. It had taken Giselle nearly one hour to transform from 'Gary', her male alter-ego, into Giselle, the hot transvestite staring back at her from the mirror. She smiled to herself as s...

First Time Cross Dressing

by fethishboy on May 1, 2003
Fetish

Lisa Smith was always a bit spoiled. She was a sexy and teasing little minx. She was 22 years old with a smoking hot body. She loved to tease and be treated like a princess. She acted all sweet and pretty but she had a wild side. She loved to control men. She loved to make her buy her stuff. She loved to cock tease. She made a lot of money on it. She loved t...

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A New Start

by Stoked Flow on Jun 20, 2020
Transsexual

You spent most of your time at home playing video games and browsing the internet. You decided to take it easy after high school before deciding college was right for you. That was a couple years ago and now you sense a growing frustration within your mother. One afternoon after dinner, you found yourself suddenly sleepy and crashed onto the sofa. Your next...

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