Cheerleader Crossdressing Stories Stories

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Masculinity Lost

by Cdslavejessie on Apr 29, 2025

Introduction: Hi yall! This is my first attempt at a story so I would love and appreciate any feedback! I’m making this up on the fly so I’d love thoughts and ideas on how we can really humiliate young Danny Stewart! I prefer my stories be based in reality (crossdressing, padding for breasts and hips, hormones and surgery vs magic or scientific machines) and...

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Kasey's Confession Ch. 15

by KaseyLegs on Sep 12, 2017
Transsexuals & Crossdressers

Dr. Duckworth, who looked just like the crazy shrink Gary I'd met while apparently imagining myself as a prostitute, had apparently been consulting with Dr. Bennett and others during my coma. He was very interested in the psychological effects that being in a comatose state for an extended period of time had on a person. When he informed me that he was willi...

Forced Crossdressing Stories

by Dayeandknight on Feb 1, 2018
Transsexual

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't yo...

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Crossdressing Stories

by Dayeandknight on Apr 29, 2025

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't yo...

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Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

Kasey's Legs

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

I had been crossdressing for close to ten years. It started as a Halloween costume gag where I shaved my legs, put on a cheerleader outfit and wore a scary mask. After I kept getting compliments on how good my legs looked I continued shaving them and experimenting with dressing in a variety of women's outfits, skirts, high heeled shoes, panties and bras. It...

Mistress Chantel, Tranny Dominatrix Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Prefix: Welcome to my next erotic story. This story will be written from the point of view of a Transvestite Dominatrix. It is a new twist in my mindset as I normally identify as submissive and as a sissy maid and slut to a dominant Master. It's my 'kink' but I have danced around in my mind a story from a position of Chantel being a true Transvestite Dominat...

The Many Tales of Crossdressing.

by Whiteskorpion on Apr 22, 2025

This story is open to anyone who wants to write a crossdressing story, it doesn't matter if it's an original story or a fanfiction. Please respect Chyoa's rules, so ****, underage sex (younger than 18 years old) and **** **** are not allowed. I would like to keep this story as organized as possible. For example, if you're writing a fanfiction, before you rea...

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Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

The Naked Bleached Blonde "Sissy Barbie Bimbo"

by Crissy on Apr 22, 2025

Did You Know? According to a study conducted on 293 female college students at the State University of New York in Albany, exposure to semen can lower symptoms of depression. And it’s mighty healthy: One teaspoon of semen contains over 200 proteins and several helpful vitamins and minerals including vitamin C, calcium, chlorine, citric acid, fructose, lacti...

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