Sissy Anal Training Stories

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Infinite Scroll

Wife Left Me so I Could be a Girl

by TammyPanty on Jul 10, 2018
Transsexuals & Crossdressers

I Am The Girl My Wife Did Not Want As the only child of a single mother I grew up around all things feminine. Having lingerie and stockings drying in the bathroom was normal for me and I always loved how pretty the full cut nylon panties and slips with tons of lace looked. I lived at home with my mother until she unexpectedly passed away when I was 23 year...

Candi's Conversion Ch. 02

by CandiCumminz on Sep 12, 2018
Transsexuals & Crossdressers

Please read chapter 1 first. - We join Candi, dressed to the nines as a sissy princess, sucking on her lipgloss tube and dancing like a slut. Her wife and her friend have just walked in on her, rubbing herself to orgasm. She's in for it now... - "What the fuck is happening here?" My wife stammered in disbelief. Her company, a friend named Lucy who I'd m...

Appointment by Card Only Ch. 03

by Sputnik57 on Sep 17, 2017
BDSM

Bruce panted in a mixture of fear, disbelief, and anticipation, his balls and anus tingling as he was gently tugged by the leash up the stairs; the beautiful mature form of the woman before him keeping his cock rock hard. Wicked smiles from passing madams and clients alike fell on the couple, but Bruce was oblivious to everything else but his superbly domina...

Getting Nailed

by jbirdman on Sep 25, 2017
Fetish

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), cross-dressing (CD), mild bondage, Trangender (TG) and a few other fantasies of mine. I hope you find it entertaining, but if you might be offended, stop reading and do something e...

My Husband a Pornstar Ch. 03

by gtanya on Mar 20, 2018
Transsexuals & Crossdressers

Please read the previous two stories to fully understand and enjoy this chapter. If you don't want to read them, here is a brief description of what has happened till now: *** My husband was conned by me into exploring his sexuality and he finds out that he is bisexual. He also agrees on being a porn-star to earn a hell lot of money for us. After shooting...

Madame Jenoix

by Candour on Sep 26, 2017
Transsexuals & Crossdressers

Chapter 1 --------- A young looking and slight 18-year-old boy sits outside the Headmistress's room, obviously feeling anxious. His legs kick back and forth under the chair and he keeps looking up at the door. His uniform looks unkempt, like he has just thrown it on after Games. After some long, countless minutes elapse, he hears a loud, slow "Come!" from...

Recruiting of a Sissy Maid Ch. 01

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

[Welcome to my next story. This story has become a little different in how I planned to write it as compared to my previous stories. It has been fully written up already, as of this first uploaded chapter. Doing it this way allows me to better proof read and adjust for future chapters before uploading each. I will submit uploads on a regular basis for my rea...

The Wedding Ch. 04

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 4 -- Teaching, Teasing and Testimonials... I was a little stunned and leery after reading my version of this contract which wasn't all that different from Patti's... From changing my name to rescinding my rights to wear male clothing while in the employment of Darren and Carol -- or Ma'am and Sir, and also, not to f...

Behavior Modification Institute Ch. 10

by NancyPan on Sep 12, 2017
Fetish

Although I continue to receive some demeaning and aggressive comments, most feedback has been positive. I appreciate all who enjoy this story, as we share similar fetishes. If you are not interested in FemDom, male feminization, and sexual humiliation, do not bother to read this series. ***** I was standing with my petticoat and the skirt of the maid's uni...

Sissy Training Vol. 01

by depositdutchess on Nov 27, 2017
Fetish

Being feminine is taught. Correcting your nasty masculine behavior with feminine manners and class is what you need. Being a sissy is your new reality. I am going to make you the pretty little girl you have always dreamt of being. You need to be taught ho live your every day life properly. You can only dream of being as sexy, girly and attractive as a real w...