Submissive Sissy Stories

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The Slave and the Sissy Ch. 05

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

Ayesha was not to be denied; slave was rampant after witnessing the erotic antics of the maids, and was anxious to please Ayesha quickly, so that he may watch over Pepper; she was so soft and vulnerable. Slave's cock rose quickly as he sniffed at the gloriously rich scent of the dusky beauty's thong. She smiled with a sense of admiration as he licked and lap...

His Sissy Bitch Ch. 01

by keptsissy on Sep 26, 2017
Transsexuals & Crossdressers

It started after a transvestite walked into the bar. Sounds like the start of a bad joke but it's not, we were in a party bar after work, me and my boss. My boss and I were having a drink after work; he was more than a little high. An obvious cross dressed man with several friends came in and sat at the bar. 'She' was very cutely dressed, stylish and sexy. M...

Sissification 101: Ch. 06

by silkstockingslover on Sep 28, 2020
Interracial Love

Sissification 101 Ch 06 Summary: Eric gets fucked by BBC for the first time; Joan gets black pussy. 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...

Sissy_World 02

by JDBones on Sep 14, 2017
Transsexuals & Crossdressers

John Maxwell hummed under his breath as he wiped down the counter tops of the kitchen, cleaning up before his Husband got home. Dinner was ready and waiting on the stove for her whenever she got home from work. He was petite, standing at four foot five, and slender though lightly toned. He had long ash blond hair that fell past his well rounded, juicy ass a...

My Husband a Pornstar Ch. 04

by gtanya on Mar 21, 2018
Transsexuals & Crossdressers

Chapter 4: Conclusion Here is a small brief of what has happened till now: My fairy husband had been seduced by a strong man at home and then had agreed to be a sissy pornstar. Fairy new master had trained him as a sissy to perform in a gay movie without his knowledge that he was making a sissy trainer porn movie the whole time. I found out and threatened...

Chronicles of Heather Maureen Ch. 09

by HeatherMaureen on Sep 16, 2017
Transsexuals & Crossdressers

Final Exam While I was waiting in bed last night for George to join me he had gathered up my clothes and purse then locked them in my car to make sure I'd spend the day with him. His clothes would fit me like a tent and his wife's merely like a pup tent so they were no help. I resigned myself to staying here and inside for the day. He made breakfast for...

Our Sissy Slave

by purekink on Sep 25, 2017
Transsexuals & Crossdressers

Let me remind you how you came to be in this situation before you refuse. I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a...

Welcome Home, Ma'am

by Miss_Ds_slave on Sep 12, 2017
BDSM

He had been waiting his whole life to find someone like her. He had almost given up any hope that there was someone out there who could give him what he so needed. He had met a few women over the years that had been willing to try and give him what he desired, but it was usually just something they did for him, not something they enjoyed for their own pleasu...

Ian's New Job Ch. 02

by SatinSlip on Dec 10, 2018
Fetish

Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex, crossdressing, and humiliation. ********** Wendy wore the shortest skirt she owned. A blue, pleated thing that stopped a few inches short of her knees. Underneath she wore red lace panties Ian had bought her for valentines a couple years ago, an...

Daddy's Sissy Staircase Ch. 01

by SissyLoniOR on Sep 28, 2020
Transgender & Crossdressers

I've cleared my calendar for the afternoon and going to be spending this time with my fwb Daddy. On the drive over to his place, it got me thinking, he and I have been FWBs for a long time, and this story is an attempt to chronicle how I went from being a newbie sissy wannabe to his addicted, shameless cock slut. This is my first submission ever here; I hope...