5 Days Captive Sissy Stories

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The Executive

by Bootfrau on Dec 24, 2019
BDSM

The Executive: or, How to Break a Slave in Seven Days * * * MONDAY. "Jesus Christ, lady," he choked. "Is that thing real?" I blatted the stun gun just under his nose. He recoiled, scattering papers across his desk. "Look, this is a business. You can't just come in here and--" "Kidnap you? Why yes, yes I can. In fact, you've been asking for it for month...

The Slave and the Sissy Ch. 02

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

Ella took the chain from their collars when they reported to her, together for the first time, in the morning. Pepper's eyes were exceptionally bright this morning, and slave looked full of vigour and ready to carry out any command that befell him without the slightest hesitation. Pepper gripped his hand tightly, lest she should suddenly wake from this beaut...

The Society Ch. 04

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

I have a little explaining and an apology to make. The last installment of The Society, called The Society part 4 was uploaded by mistake. If you are following this story you will find that the first part of this installment is very similar to part 4. Please take this story for what it is, parts 1 through 3 and then followed by this installment, part 5. Sorr...

Appointment by Card Only Ch. 06

by Sputnik57 on Sep 17, 2017
BDSM

His landlord was not best pleased when Bruce announced his immediate departure, but was happy to hand him a bill requesting three months rent in lieu of his vacation without notice. He packed his laptop and the few items of decent clothing and sparse possessions into a sports bag and slung it into his car, then drove back to the house, his mind racing; he co...

Eve Quest Pt. 02

by JJ Neal on Sep 19, 2017
Transsexuals & Crossdressers

Chapter 6 I tossed and turned all night sleeping for short periods, but afraid I would oversleep or that the clock wouldn’t go off. About 4:30 I got up. I reasoned I’d need some extra time anyway so I got started. I sat on the toilet thinking about my douche. Somehow a douche seemed so much more acceptable than an enema. I tossed my gown on the bed and fill...

Husband, Drop to Thy Knees! Immediately! Ch. 01

by Ashesh9 on Mar 7, 2018
BDSM

"Husband drop to thy knees!! Immediately knave, dost thou comprehend???" her right hand shot out & expertly boxed the ears of the blond, blue eyed Greek God standing deferentially to Her Majesty's left!! Without demur he smoothly dropped to his knees at his Sovereign's Royal Command!! The vast assemblage watched the spectacle appreciatively: male phalli th...

Hubby Drop To Thy Knees! Ch. 01

by Ashesh9 on Sep 17, 2017
BDSM

CH1. : HUSBAND, DROP TO THY KNEES!!! IMMEDIATELY! "Husband drop to thy knees!!! Immediately knave, dost thou comprehend???" her right hand shot out & expertly boxed the ears of the blond, blue eyed Greek God standing deferentially to Her Majesty's left!! Without demur he smoothly dropped to his knees at his Sovereign's Royal Command!!! The vast assemblage...

I Get Married

by hotdaddy9 on Mar 7, 2020
Transsexual

It is such a romantic day. Just right for some me time. I am getting married to myself today. I needed to shower. I had a terrible week at work. My boss was her typical self; bitchy, paranoid and touchy-feely. She actively questioned my manhood, my cock size and whether I had what it took. I would quit but for the fact that I am paid so much. I got home and...

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Aztec Art - The Path to Submission Ch. 05

by Sputnik57 on Dec 23, 2017
BDSM

Lloyd squirmed at the pole in a strange blend of discomfort and sexual euphoria, on an image flickering to life upon the screen before him, his mind fast reclaiming its lucidity from the waning drug. He fought with his own conscience as that lucidity only served to heighten his arousal, his boning cock betraying the undeniable pleasure that had been awoken b...

Getting Married

by hotdaddy9 on Mar 17, 2020
Transgender & Crossdressers

It is such a romantic day. Just right for some me time. I am getting married to myself today. I needed to shower. I had a terrible week at work. My boss was her typical self; bitchy, paranoid and touchy-feely. She actively questioned my manhood, my cock size and whether I had what it took. I would quit but for the fact that I am paid so much. I got home...