How To Fuck A Sissy Stories

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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...

Sissy Chantel, New Reality Ch. 07

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Seven: At 'The Agency' and I'm Off to a New Start In My Sissy Life. "Girls this is your new dorm mate, Sissy Chantel." one of the security staff says. The other staff member adds, "You shall take her into your group, help her set up her things and then take her around on a tour of the facilities and such. Report to the office after doing so, OK?"...

Sissy's Decline into a Slut Pt. 04

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Six: Chantel's Decline is Achieved, Owned by a Black Master as his Sissy Maid and Slut. I cannot believe at what is happening to me here. Master named Gage is about to purchase me and place me into slavery as his sissy maid and sissy slut. I am near in panic, I want to run away, get into my car and drive for the safety of my home. But I know this wi...

Cockland Island Pt. 05

by Sissyhalo1 on Feb 3, 2020
Transgender & Crossdressers

Waking up like that I think my brain wanted not just more but to place everything that happened to me in an order that I could handle. So deeper into sissyness it was. Playing with my butt plug until I was edging myself and losing myself in it. Abby showed up. Rolled a joint and watched me. "C'mon Nikki, up, let's get you fed and working out." It was h...

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...

Sissy's Decline into a Slut Pt. 03

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Five: Oh, Oh, Things Look to Begin to Radically Change for Chantel. Well another week has passed by, it's Friday evening and tonight I have to go back to the rest area to hook up with Barry and Ralph as they instructed from last Friday after having me suck their cocks. They promised me that they will fuck me tonight and share me with even more men....

The Prostate Exam Pt. 05

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

Since giving himself away in his first prostate exam to his Dominant Doctor Megan he had been prepared for use by an old Master, now Sissy was on her way to be used. Sissy was breathless as she read the text from Master V, she looked around the small airport to make sure she didn't know anyone, whilst she was looking at her texts. Thank goodness she didn't....

From a Husband to a Dutiful Sissy Ch. 06

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Six will compress time a bit more forward in moving the story through time. It will be set two months forward from the original start date of the story in Chapter One, when Helen found out her husband Phil enjoyed crossdressing and fantasized about being sissy maid and a sissy slut. It all picks up with bit of recollecting from Phil who is now Chante...

Sissy Chantel, New Reality Ch. 11

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Eleven: Sunday Fun Well now that our Masters and Mistresses have left us here in the locker room, with all twelve of us sissies now freed from our chastity, our sissy dicks are getting quite hard. We have been allowed a period of sissy sexual freedom. For the next 45 or so minutes we are to engage in a sissy orgy to relieve our pent up sexual desire...

The Prostate Exam Pt. 08

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read on unless extreme sissification and forced gay and bi scenes, watersports and cum eating, really flick your switches. I don't want to offend anyone so thought this comment might help. ***** It'd all started with a routine visit to his Doc for a simple prostate exam. His Dominant female doctor had pushed her finger just into his ring and...