Sissy Slut Captive Stories

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The Capture of Sweet Pussy Ch. 03

by SirStroker88 on Sep 17, 2017
BDSM

Chapter 3 – Donna's Story 'Damn Sid, you're right, she is a beautiful sight." Donna was looking down at Pam Martini, the bitch she knew from the office. What she saw now was a frightened young lady on all fours wearing nothing but a collar and a blindfold. She was leashed to a whipping post and quietly sobbing to herself. Donna knelt and stroked Pam Sweet...

Dani's Night Out

by Jemina004 on Sep 26, 2017
Transsexuals & Crossdressers

Danielle Winona was very nervous. Maybe it was because he was standing outside the door of a strange man's house at night in a mesh top, tiny skirt and thong panties. Maybe it was because he had just rang a stranger's doorbell and he had no idea of what awaited him inside. Whatever it was, and whether he enjoyed it or not, Dani had to be as pleasing and sexy...

The Prostate Exam Pt. 04

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by not being able to resist pushing back against her finger, forcing her finger deeper into asshole. At that point his female doctor had decided to test just how submissive he was. She gave him the option to back out if he...

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 Unsuspecting Candidate Ch. 02

by missvicky53 on Sep 11, 2017
Fetish

Part 2 Helen continues Mike's training, this time in a French Maid's uniform The aftershocks of his climax were still coursing through his body as I teased him. "Did you have a nice cum, sissy?" I cooed at his still bound form. "Do you want me to release you now?" "Yes, please," he replied. "I'd like to get dressed now." "And get dressed you shall," I tea...

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...

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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Jacki's Journey into Sissyhood Pt. 03

by jacki697 on Sep 18, 2017
Transsexuals & Crossdressers

This is the 3rd installment of the Jacki's Journey series. I'd like to thank those who were nice enough to add comments and feedback on the proceeding stories. I'll try and keep them cumming. ***** I had a couple days to evaluate Steve and Laura's offer and I was no closer to a decision than I had been. I went back and forth on the verdict. How was I goin...

The Sissy and the Pet

by Detailed_Dominant on Sep 18, 2018
BDSM

I sipped my drink and let my eyes dart back and forth between my phone and the entryway. I hadn't wanted to risk being late, so I tried to make sure to arrive 10 minutes early. Maybe I had just estimated the traffic wrong, maybe I had just been more eager for this meeting than I was prepared to admit to myself. I showed up almost 40 minutes ahead and schedul...

Sissification 101: Ch. 04

by silkstockingslover on Jul 14, 2020
Transgender & Crossdressers

Sissification 101 Ch 04 Summary: Eric sucks his first BBC in a threesome with Joan. Thanks to Eric who requested and helped plot this lengthy story. Recap so far: Sissification 101 tells the story of Eric, a mid-30s Asian, who has been hiding his sissy side curiosity for years until he is caught in pantyhose watching hypno-sissy porn by his...