Pretty Little Sissy: Pretty Little Sissy, #1

By Clea Kinderton

Taylor always knew he wasn't like other boys. While other boys were out playing football, Taylor was trying on pretty dresses and learning how to apply makeup. But Taylor's shameful crossdressing secret has just been exposed by the one man whose judgment he fears the most: his old schoolyard bully, Randy.

In a surprising twist, Randy has decided he wants to help Taylor come to terms with his true sissy identity ... and train him in the skills he'll need to perform his new role...

This 12,000 word (38+ page) erotic short is packed full of explicit, erotic genderbending feminization training, D/s play, short skirts, thigh-high stockings, and lace panties.

• Language: English
• Publisher: Red Lamp Press
• Release date: Jun 16, 2016
• ISBN: 9781533702012

Clea Kinderton

I've always had a wild imagination. I love fat fantasy novels, B movies, comic books, and scifi. But I also love romance and sex and you'll find plenty of both along with heaps of humor, mystery, and suspense jampacked into some of the hottest, hardest, kinkiest stories you may ever read. Strap yourself in, it's going to be a wild ride. I'm always interested in hearing what you have to say and welcome suggestions. You can contact me at [e-mail] and follow me on Facebook: https://www.facebook.com/CleaKinderton/ and Twitter: https://twitter.com/CleaKinderton.

Book preview

Pretty Little Sissy

Pretty Little Sissy, Volume 1

Clea Kinderton

Published by Red Lamp Press, 2016.

This is a work of fiction. Similarities to real people, places, or events are entirely coincidental.

PRETTY LITTLE SISSY

First edition. June 16, 2016.

Copyright © 2016 Clea Kinderton.

ISBN: 978-1533702012

Written by Clea Kinderton.

Table of Contents

Title Page

Copyright Page

Pretty Little Sissy

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Further Reading: Strange Tides

Also By Clea Kinderton

About the Author

Taylor looked at himself in the mirror and frowned.

He turned around, looking over his shoulder, and gave his butt a little wiggle. The tightness of the dress only seemed to emphasize how small his ass was. He turned to the side and examined his silhouette, sucking in his stomach to make himself beanpole skinny, but it just wasn’t right. It didn’t make his butt look any rounder.

He was built like a boy. Flat as a surfboard. He had no boobs and no butt.

Taylor sighed.

Maybe if I stuff the bra more, he thought.

He grabbed another pair of his sister’s socks and reached inside the top of the dress, stuffing one sock in each cup of his sister’s bra. He adjusted the bundle of socks in each cup, trying to give them a nice round shape, and checked himself again in the mirror. He pulled his long, thick brown hair out of the way, draping it down over his back.

Better, but still not good enough.

Taylor’s shoulders slumped. All he wanted was to look good in a dress. Was that so much to ask?

He peeled off the dress with a huff and tossed it on the bed. His sister wouldn’t be home for hours, so he still had plenty of time to tidy up.

He looked at himself in the mirror. He was still wearing the bra and a pair of his sister’s black lace panties. The panties were tight and did a good job holding his penis up snugly between his legs. He was glad that, if nothing else, he had a very small cock and balls. At least they didn’t get in the way when he wore his sister’s clothing. He was also wearing a pair of his sister’s black stockings and black strappy heels. He was glad his feet were the same size as hers. He really liked the way the stockings and heels looked together and wanted to find something that went with them.

He went to the closet and took another look at his sister’s outfits. He found a black ruffly dress that he hadn’t noticed before, stuffed behind some old jackets. He took it out, pursing his lips thoughtfully. It looked awfully short. He was dubious about finding anything that would look good on him. Still, it wouldn’t hurt to try.

He raised the dress over his head and wriggled inside of it. Getting his arms through the sleeves was no problem; he had skinny little arms just like a girl. In fact, he was almost exactly the same size as his sister. Her clothes were a little tight in places — especially across the shoulders — but he could wear them without stretching them. Which was a good thing for him, because otherwise she probably would have noticed.

Crossdressing had been Taylor’s secret, guilty addiction for as long as he could remember. He’d been caught once by their mother when he was younger and since then he’d gone to great lengths to conceal his habit. He didn’t even own any women’s clothing himself, but restricted himself to what he could find in his sister’s — and occasionally his mother’s — wardrobes.

Taylor pulled the dress down over his hips and then as far down his thighs as it would go. The dress was really short. It barely covered his ass, and left a good deal of skin exposed between the stockings and the bottom of the dress. Taylor was glad he’d never grown any hair on his legs above the knees. The dress was too short