Crossdressing Friend Stories

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Orientation
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Me & My Wife Are Sisters Now Ch. 01

by gayindia1980 on Sep 16, 2017
Fetish

Hi I am Ravi, 28 year old from Delhi 5.8, slim, hairless and minimal facial hairs. I am married for 3 years, my wife Shivika is 24, 5.4, slim and beautiful. I was in crossdressing since my school days. I use to wear my sister's and mom's clothes when nobody used to be at home. In 12th class I lost my virginity to a college guy whom I met online but that anot...

Forgiving Wife Pt. 03

by manatdawnrise on Feb 1, 2018
Transsexuals & Crossdressers

The night was still early but with the combination of travelling, drinking on an empty stomach and the emotion of talking about my interest in crossdressing, I was exhausted. I suggested going to bed to which Mandy agreed. I stood behind her brushing my teeth wondering what was going to happen now my sordid secret was out. I caught Mandy's eye in the mirro...

Danielle's First Meeting

by CDDanielleNNJ on Sep 12, 2017
Transsexuals & Crossdressers

DISCLAIMER: This story involves sexual situations between one or more cross-dressers or adult males. If this offends you, please leave. Otherwise, please enjoy this fantasy of mine. Please post wherever you feel and share with your friends and loved ones. All I ask is that my e-mail address remain in place, as I am the sole creator/author of this work. All c...

Office Secret

by bullockhall on Sep 11, 2017
Transsexuals & Crossdressers

I am a bisexual male who enjoys crossdressing in private. Nobody in my office knows my secret, and I planned to keep it that way. Suits and ties during the week, lingerie and stockings on the weekend. Lately I've begun wearing panties under my suit to enjoy the feeling all day. When I woke up this morning I was feeling naughty. It was Monday morning. I'd b...

A Demon's Revenge

by SnoopWorg on Nov 20, 2020
Fantasy

Prologue When Aron Steelside began adventuring, the golden years were already past. Almost all the High Demon lords had long been defeated by the heroes of old, whose statues now resided in the cities they had made safe. There was still some money to be had clearing out nests of goblins and protecting smaller villages from bandits, but fame was a pipe dream....

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Sweet Alice

by Akito01 on Sep 13, 2017
Transsexuals & Crossdressers

It is typical in these sorts of confessional stories to change names to protect the innocent, but in this case the concept of 'innocence' barely applies. That said, I will refer to my friend here as Sweet. If you're old enough to remember the singer Matthew Sweet, then hopefully it won't seem too odd to call him that. I think the gender ambiguity of that nam...

Pokeslut

by AzorAhai on Apr 6, 2019
Fantasy

Introduction to Pokeslut: Pokeslut is an alternate universe to the Pokemon games we all know and love but with a twist, the women in this Pokemon universe are not seen as equals to their male counter parts and often if a female trainer loses in battle they must pay the trainer in either sex or cash. It varies from person to person, some guys will just let yo...

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Schoolgirls and Schoolboys

by JDBDS on Sep 16, 2017
Transsexuals & Crossdressers

(Disclaimer: This is a true story.) This is a story about myself, my girlfriend Shannon, and one really, really hot crossdressing dude. Or girl. A note--I would describe myself as a straight guy, while she would describe herself as 75% straight or so. The story begins back in December or so. Shannon and I are both in our early twenties, we've been dating f...

To Be, or not To Be; Fucked

by JakeInalake on May 29, 2020
Fetish

Gabrielle was far from below the average highschool boy standards of excellence. For starters, he was way shorter than any boy he knew, he was a stout 4 foot eleven inches, making him even below or barley on par with women. He was very curvy and feminine growing up as well, attempting many sports like track or swim had only decreased his hope in attempting t...

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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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