Crossdressing School Stories

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Smoking With Friends Ch. 01

by jjww100 on Sep 16, 2017
Transsexuals & Crossdressers

The phone on my nightstand rang and I groaned as I grabbed it and looked at who was calling. It was Benny and I answered it. "Hello". "Yo Justin, I got $250 worth a weed! You need to come pick us up so we can smoke it!" "Just Wait. Who are you with?" "I'm chilling at McDonald's with Matt and Vic." "Okay, I'll be there in twenty minutes." I hung up, qui...

Sarah Was Caught Masturbating

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

After collage, my girlfriend's best friend and I found ourselves working in the same town and so we decided to share an apartment. Her boyfriend had another year to go in college and my girlfriend worked in a different city. I loved living with her; we became the best of friends; just friends but very close. We cooked together every evening and watched TV....

Sissy Escape

by Haley_Hazel on Sep 26, 2017
Fetish

You are John Doe An average man, not too young, not too old. You have zero money, no car, no girlfriend... Basically a real loser. You live in a dive apartment downtown. It's not a great place to live, but it's home. Everything you need is right nearby. Groceries, Bar, Restaurants, it's near a park, and there's even a porno shop down the road. Because it's d...

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Real Life: The RPG

by Katnaace on Nov 25, 2019
Fetish

Having logged in, you get to the biggest question of all - who are you going to play? It's not like this is a big deal. You can just create your character and be on your way.What's next? Danny Hopkins - Dude with a sister Lydia Onava - Widow waking up in an unknown place Claude Rogers - On his way to visit his Aunt Henry Wells - Protesting H20 What's next...

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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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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...

By the Grace of Guile

by komrad1156 on Sep 14, 2017
Transsexuals & Crossdressers

*Author's note: Several years ago, I read an interesting book by author Loyal Rue, a professor of Religion and Philosophy at Luther College, called By the Grace of Guile. An excerpt from one review says this: "For people who are troubled by a world increasingly filled with the sweet-talking duplicity of politicians, preachers, advertisers, and sundry huckste...

Life and Time of Lady Vargos Ch. 01

by rik581 on Oct 3, 2018
Transsexuals & Crossdressers

I am in the process of reposting my stories. *** "The Life and Times of Lady Vargos" is the second book of the Martin Hastings adventures into a life of forced feminization. This story follows the feminization and marriage of a reluctant young man as he is forced to accept his fate as a male/bride, in a same sex marriage, arranged by his family. This stor...

Perfection

by ValoryG on Apr 23, 2019
Transgender & Crossdressers

It all starts, innocently enough, when Joanna's looking for a dresser. On one hand, she can just go to a big box furniture retailer and get an inexpensive, functional one that looks decent (and build it, of course). Or, she can browse around online and find a new or used one with a more elegant pedigree. Joanna, by the way, is a very practical, elementary s...

A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

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