Sissy for the Strict Headmistress: Femdom and Forced Feminization Book 1

By Charlie Quinn

When burly tradesman Tyler finds some schoolgirl's clothes hidden away at the empty school he’s working on, he can’t resist dressing up and exploring his secret sissy fantasies. But the strict Headmistress catches him in the act and punishes him in a most unexpected way – forced to fully feminize, he is spanked over her desk and made to satisfy both her and himself. But who’s enjoying it more – the hot but stern Headmistress, or big, butch Tyler, all dressed up as a girl? Explicit
12,000-word story with forced sissy feminization, CFNM, erotic humiliation, spanking, JOI, a submissive male and a very dominant woman. Enjoy as a standalone novella or read as part of the 'Femdom Feminization' series. All characters 18+

• Language: English
• Publisher: Charlie Quinn
• Release date: May 26, 2022
• ISBN: 9781005562922

Charlie Quinn

Charlie Quinn writes all kinds of femdom stories, including dominated husbands, willing male slaves, sissy men, and submissive boyfriends. They all adore and serve their Mistresses, as they are taught to obey and please the women in their lives. Find stories of male chastity, of dominant futas, of feminization, of first time gay encounters, of punishments and teasing, denial and service, all between the pages of Charlie Quinns books. Check out the audio and paperback versions too!

Book preview

‘Sissy for the Strict Headmistress’

Sissy Book 1

Explicit Femdom Humiliation, Forced Sissy Erotica

By Charlie Quinn

Copyright 2022 Charlie Quinn

Published by Charlie Quinn at Smashwords

Smashwords Edition License Notes

This ebook is licensed for your personal enjoyment only. This ebook may not be re-sold or given away to other people. If you would like to share this book with another person, please purchase an additional copy for each recipient. If you’re reading this book and did not purchase it, or it was not purchased for your enjoyment only, then please return to Smashwords.com or your favorite retailer and purchase your own copy. Thank you for respecting the hard work of this author.

Find more Charlie Quinn Books at Smashwords

Table of Contents

Chapter 1

Chapter 2

Chapter 3

Chapter 4

Chapter 5

Chapter 6

Chapter 7

Chapter 8

Books by this Author

Chapter 1 Prologue

Miss Henderson took Tyler’s hand and led him to the large carved dark wood wardrobe that stood against one wall.

She opened the door to reveal a full-length mirror on the inside of its door.

She stood him in front of it and made him look at himself.

Tyler couldn’t believe what he was seeing.

He looked girlish and sexy with his short skirt grazing the top of his stockings, his tight blouse the hint of a bust underneath, and the red lipstick giving his face a decidedly feminine look.

In the dim light of the office and the slight blurriness of the antique mirror, he could ignore the details- his broad shoulders, his hairy legs, his stubble.

He just focused on the soft sway of his skirt as he turned and looked at himself, on the way the bust seemed to give him a waist too, changing his profile, and on how full and glossy his lips looked.

He looked good.

Miss Henderson reached under his skirt.

Her fingers fastened around his throbbing cock.

He gasped in shock. She was touching him. She was squeezing his dick. He could almost come, just from this touch. He stared wordlessly at her. Was she going to make him come right here, right now?

Oooooh. He let out a faint, strangled moan, unable to help himself as her fingers tightened on his shaft and the soft fabric of the panties pulled tight across the head of his cock.

You’re turned on by this, aren’t you? she said, in a fierce whisper.

Yes, he squeaked out, only able to think about coming, or trying to stop himself from coming as her fingers held him tightly.

You’re a bad girl. A very bad girl.

She squeezed him harder and almost seemed to stroke him, rubbing the pale blue silky satin of his girl’s panties against his cock before letting go.

Bend over my desk, she snapped.

He was so dizzy with excitement, so full of the desire to come that he didn’t even think about it. He bent over, resting his chest on the broad expanse of her desk.

I’ll have to punish you for this, she said.

Chapter 2

Tyler was in a bad mood again.

His apprentice was off sick. Hungover, more likely, he muttered to himself.

And he had to find the fault in the electrics that kept tripping out an entire wing of Windsor Grange, a grand old building which housed the boarding school.

Fortunately, it was the middle of the long summer vacation, so the school was deserted.

While he