Castrate Sissy Stories Stories

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Mommy and Goddess

by force_transitioned on Sep 12, 2017
Transsexuals & Crossdressers

Andrew never saw the noose. He was uncomfortable around his new mother in law - his wife's new step mom. And rightly so - he was, after all, going through the woman's intimates since the day she entered their lives, some two years ago, shortly after the marriage. Had he overcome his guilty reaction, he may have noticed a recurring theme in their conversa...

Cuckolding Sindy Ch. 02

by SindySuxALot on Sep 13, 2017
BDSM

Sindy listened intently over the intercom as Lucy was in the other room with her dates. The moans and groans were constant as her Mistress orgasmed repeatedly. It always turned Sindy on immensely to hear her Mistress with other lovers. She sat in front of the computer with her largest vibrating plug inserted in her ass and watched the sissy on the computer m...

Miss Annabelle Ch. 02

by Timewarp10 on Oct 16, 2018
BDSM

As Annabelle's first term at University drew to a close, I had become her slave: cleaning floors, laundry, ironing, cleaning her shoes, making her bed, sorting her clothes and other household chores. Each day was filled nonstop with toil, from early morning to late night, stopping only when she had gone to bed to sleep, and even then I would have to be alert...

Simon Sissy Slave Ch. 04

by Timewarp10 on Aug 20, 2019
BDSM

Simon staggered in for work the day after the slave auction, his body stiff and sore. Mr Berne and the others in the post room were shocked to see the sissy's bruised and lacerated buttocks. Barry's stiff cock betrayed his feelings; whipping and torture excited him. His sadistic nature relished the thought of thrashing Sissy senseless. Sissy was his fuck t...

Simon Sissy Slave Ch. 03

by Timewarp10 on Jul 30, 2019
BDSM

Mr Berne watched with satisfaction as the sissy paraded in the post room. Sissy walked gracefully in high heels. His ballet training made it easy. He knew how to walk like a woman. He had practiced, and he could walk with a book balanced on his head. It gave him poise, and the high heels gave elegance to his calves. The skirt was short enough to look slutty,...

End Scene

by felicia_rene on Sep 28, 2020
Transgender & Crossdressers

This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy Description: When a rich wife discovers that her husband married her for her money and to add insult he turned out to be gay. ROLL CAMERA My rich wife had me over a barrel after finding out about my affair with my handsome boy toy assistant. She took a...

Family Chastity Story Ch. 03

by antares34 on Jul 30, 2019
BDSM

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My gimp son and I have settled into a routine. Permanent chastity with monthly releases. These releases occur on the first day of every month. I...

My Toy Nancy Ch. 02

by NiceNastyMann on Sep 19, 2017
Fetish

I wake up, sunlight streaming into the bedroom windows. I check the time – it's late morning. Good thing it's Saturday. I look across the bed and see Nancy, she's still asleep. Well, let's see if I can awaken her. "Nancy, time to wake up." I watch as she opens her eyes, and I don't catch that neutral emotional state any longer. In fact I'm catching a lot of...

Ballbusting scenarios

by NeedMoreBallbusting on Jul 27, 2020
Fetish

This will be a place for all my stories where you can pick and choose which ones you like. All the stories will have ballbusting in them. Will be trying to add new chapters often. Also if you are going to add a new section to the story or a story branch don’t stop after one but continue to put more and finish. What's next? Roshambo Home invasion Ballbustin...

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Casey's Submissive Journey Pt. 13

by corduroysissy on Aug 1, 2018
Transsexuals & Crossdressers

Since Susan had been treating him so nicely, Debbie suddenly felt a little strange when she abruptly walked out. Seeing the confusion on his face, Maxi said. "Don't worry Debbie she has things to do, she'll be back when she's ready to cum again." She slowly smiled. "Oh my, how amusing. Did you think you two were girlfriends now?" She chuckled. "Sorry siss...