Training the Sissy Virgin: Crossdressing Virgin

By Scarlett Steele

It was time to fulfill his end of the bargain and strutt his sissy persona across the crowded shopping mall.

The sissy virgin rummaged through the bag of women's clothes shaking his head in astonishment. It was mere hours ago when David had sought the services of a high class escort to finally lose his cherry.

But his choice of escort had led him down an unexpected journey.

Lexi skillfully concealed her two sides, playing the role of a sensual submissive escort at times, and at other times.She unleashed a dark and dangerous side as she transformed into a cruel and dominant dominatrix, teasing and tormenting the unfortunate males caught in her web of pain, punishment and humiliation.

The stunning escort learned of the virgin’s crossdressing and chastity fantasy during their first dinner date together. The mere thought on flaunting her naked body in front of the virgin, before cruelly locking him in a steel chastity cage and forcing him to dress himself in her underwear awoke her hidden Domme.

And as the evening progressed, the cruel and sadistic side of Lexi paraded the naive virgin around, forcing him to seal himself in a painfully restrictive chastity cage and donning her pink underwear, tending to the Domme’s pleasures.

And once she had stripped him of his dignity, Lexi left her male client naked and stranded in the alleyway behind the hotel with a bag of her clothes and her a number scrawled on a piece of card. .

Bruised, humiliated and feminized, David remained the naked virgin he was at the start of the night. His cruel mistress has dumped her used clothes in a bag black with instructions to dress himself in her pink underwear, short white skirt and pink high heels and then to call her.

The sadistic Mistress assured David she would eventually relieve him of his virginity. But first he would need to earn the right to be released from his steel chastity cage in order to free his arousal.

And in order to prove his worth, David’s first task was to dress up as a mature schoolgirl on her way losing her own cherry and parade her sissy ass across the crowded shopping mall.

• Language: English
• Publisher: Scarlett Steele
• Release date: Jul 22, 2017
• ISBN: 9781370996018

Scarlett Steele

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All Right Reserved © Scarlett Steele 2017

All rights reserved. No part of this publication may be reproduced, distributed, or transmitted in any form or by any means without the prior written permission of the author, except in the case of brief quotations embodied in critical reviews and certain noncommercial uses permitted by copyright law.

Individuals on the cover are models and are used for illustrative purposes only.

Authors note: All characters in this story are 18 years of age and older. This is a work of fiction, any resemblance to real live name or events are purely coincidental.

Be aware: This story is written for, and should only be enjoyed by, ADULTS. It includes explicit descriptions of intense sexual activity between consenting adults. Said activities include, but are not limited to female domination, pegging for the first time and a busty young women taking a man on the ultimate ride he will ever experience.........

Note that this work of fiction resembles a fantasy world, all events taking place are a result of a role play amongst all parties and all parties are fully consenting adults.

This ebook should be purchased/borrowed and read by adults only.

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Crossdressing Virgin

The cold snap dug its vicious claws into David, piercing his naked skin. The virgin shook himself awake, his body shivered involuntarily as the unrelenting cold encapsulated the rest of his trembling body.

Fuck David muttered incoherently under his breath desperate to shake the sleep out of him.

The naked male scanned the dark alleyway regrouping his senses, his memory stirred awake, desperately trying to recall the events which led to him stripped naked in a dark and cold alleyway. A sharp twinge between his legs tugged his attention towards his groin, he peered down and noticed his cock was trapped inside a small silver cage, his ballsack hung loose from the device but it appeared his cock was securely locked.

David lifted his package up cradling his swollen testicles and trapped cock and observed the device sealed around his manhood. A small padlock was thread through the chastity cage preventing unauthorized access.

Lexi David whispered to himself as his mind became refuelled of the memories from the night before.

David smiled as he cursed his predicament, he was a virgin who as the age of twenty two was desperate to pop his cherry in style. He had secured the services of a busty young blonde with whom he planned to wine and dine before surrendering his virginity to. However, the plan had strayed from the course David had imagined. The escort, Lexi doubled as a Domme, she had teased and strung David along carefully prying out valuable insights from the virgin’s fantasies and dark fetishes. And once she learnt David had secret desires to submit himself to females, surrendering his manhood to chastity and his admiration for women's clothes. She had taken full advantage of this information.

In a crowded restaurant, Lexi has slipped under the table, yanked her client's virgin cock out of his trousers and locked him securely inside a small and tight silver chastity cage. The seductive Domme dangled the key to the chastity cage at the crest of her cleavage teasing David to wear her moist black panties under the table at the chance of release. David hesitantly obliged as he robed his trapped cock inside the escort’s panties.

David had expected his throbbing cock to be unleashed once the couple made it back to the pre-booked penthouse suite, but the desperate virgin found the escort’s desires for anal sex were different to his. Once the couple had stumbled back to the hotel room, Lexi forced her client to worship her ass, slipping his tongue deep inside her anus as he tongue fucked the darkest parts of her ass. She coerced him to wear the remainder of her underwear while blindfolding him with her own panties, and when David’s sight was momentarily blocked, she introduced the virgin to her huge black strapon.

The innocent virgin had surrendered his submissive body to the escort’s dominant body as she ripped his anal cherry out from under his nose in full view of the hotel room camera recording the events.

David smiled as his mind raced back to the moment following immediately after the escort had torn through his anal virginity. He smiled fondly as the memory of the escort thrusting her knee into his crotch, pulverizing his tender testicles. She had hurled his sore torso into the alleyway, stripped him of his clothes and belongings and disappeared.

David looked around squinting as he struggled to make out a small black bin bag to his left, the sun was rising in the far distance and the threat of the world walking up and walking across the streets, peering into the alleyway stroked David masochistic desires. He slipped his hands between his legs and gently massaged his balls, the large orbs still ached from the brutal attack mere hours ago. David smiled to himself. He knew deep down inside he was still a virgin, the escort he had booked to pop his cherry with him had strung him along and humiliated him but beneath the layers of his masculinity, the virgin was pleased the escort had violated his ass and feminized him in front of the cameras.

The sissy virgin’s cock strained against the confines of the tight cock cage, desperate for releases as it sniffed the fresh air. David noticed the a white sticker on the black bin bag with the words ‘OPEN ME’ scrawled in pink , he dragged the bag closer to him and tore open the top.

The cold