Crossdressing First Time Stories

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The Marriage of Martin Hastings Ch. 17

by rik581 on Sep 14, 2017
Transsexuals & Crossdressers

Martin sat alone in a small interrogation room. The large wood table with the two empty chairs on the opposite side of the table were all the furnishings in the room. The humiliation Martin had suffered as he was brought through the police station, the giggles, sneers and staring were still fresh in his mind. Though he was told he was not under arrest, he fe...

Brat Boys Punished

by humiliationstation on Feb 29, 2020
Miscellaneous

In this story you play as a series of boys.What's next? Martin, a 22 year old goth Albert, a 19 year old library assistant What's next? Martin, a 22 year old goth Albert, a 19 year old library assistant...

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A Transvestite Odyssey

by lynntg0444 on Mar 18, 2020
Transgender & Crossdressers

I like playing a girl, but it's complicated. I have always been more attracted to women than men, and had many relationships with women including two marriages. As a young man I had several sexual experiences where I played a feminine role. Wearing girly things was a real turn-on for me, and it seemed to make it less queer for us both. I would later learn th...

Gender Change: Magic Closet

by Zekar on Jan 26, 2017
Fantasy

There is magic in the world. Narnia was just the tip of the iceberg when it comes to the magic that a wardrobe or closet can do. You find yourself directly in the crosshairs of such a magical encounter. Whether malicious or benevolent, that is up to you... This is merely the introduction to a much more interesting tale. (Dear reader, if you like this story a...

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A Humiliated Tomboy

by humiliationstation on Feb 19, 2020
Exhibitionist & Voyeur

Alex sat on her bed, playing video games. She was a cute high school senior in a baggy hoodie and basketball shorts, her orange hair cropped at her shoulders. She was sucking at her braces in concentration when she was interrupted by a knock on her bedroom door.What's next? Claire, her bully Her best friends Nate and Jane What's next? Claire, her bully H...

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A Taste Of Lace

by AdamZasse on Sep 13, 2017
Transsexuals & Crossdressers

By Adam and Evie Zasse The authors would like to extend our thanks to volunteer editor 'Larry in Seattle' for his help in proof reading this story and for his insights and suggestions I've never been into crossdressing. Oh sure I swiped a few pairs of panties from my mom over the years. But they were only something to wrap around my dick when I jerked o...

Submission

by Domestic on Sep 24, 2019
BDSM

Your name is John Doe. Where this story takes you is up for your decision. You can choose your gender, you can choose your significant other. But after that, you will lose the ability to choose. You will become obedient, like you know deep down you should be. Ready? Pick one, and begin. NOTE: {[email protected]}It is highly recommended that you play thi...

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Sweet Treat

by SaucyMasquerade on Sep 14, 2017
Transsexuals & Crossdressers

I As the water streamed across the window pane, I watched Jayne pull her coat tight, dashing from the car, through the torrential rain into the house, cursing the British summer in all its soaking glory. "Steve," she called, as she hung up the coat to dry, "I've an invite here, to a fancy dress party, Helen is holding on Friday" "I'm in here," I called...

All I Want for Christmas, Is You! Ch. 01

by grgy56 on Dec 17, 2017
Transsexuals & Crossdressers

"Open mine first!" Cheryl gleefully shouted as she handed me a beautifully wrapped Christmas present. It was a cold, crisp, white Christmas morning. But much later in the morning than I would usually get up for Christmas. For some reason, I slept in regardless of my excitement to open the presents under the tree. As a kid, we would open our gifts on Chris...

A Night Drive

by 13feathers on Oct 3, 2018
Transsexuals & Crossdressers

My heart was pounding; my parents had finally, finally, left. On date night, they might be out of the house for four hours, maybe more. It was more than enough time for what I had planned. They were standing by the curb, smiling as I waved to them from the veranda. As they took off and drove, my body quivered with the thought of what I'd do next. The secon...