Sissy Anal Training Stories

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Infinite Scroll

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

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...

Being Holly

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Okay like right off I want to make it clear it's Holly now and forever. Holt's fucking dead and I'm killing anything that's left. And that's a damned good thing. See Holt was an asshole, I...he...that person I was...I was raised by an asshole. My dad and he wasn't a nice guy. He was a jock, he was a mean jock raised by worse my grand dad. Holt was part...

Sissy Boy Secretary Ch. 06

by Hotenuf4u on Sep 19, 2017
Fetish

When we got to the car Elaine said, "This won't do, you are missing something Sissy Boy. Kneel down here," as she pointed to a place just behind her car. I immediately knelt down, hoping no one would see. "Lisa my little Slut, remove your stockings and garter belt," it wasn't a question. As Lisa was getting done removing the items, smiling at Elaine as she...

Neighbourhood Terror to Sissy Pt. 12

by Fibaro on Sep 9, 2019
Transgender & Crossdressers

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** Chapter 14 On Monday morning Mark got woken up rather roughly. It was only 7:30 am, but his phone was going off loudly. Confused he picked it up to see who would call at this ungodly hour. Nerves instantly struck him when he saw his girlfriend's caller ID pop up. What ha...

Handyman Pt. 04

by lovedart54321 on Sep 28, 2020
Transgender & Crossdressers

I started my new job and was forced to focus my attention on learning a new field, with a strong understanding of chemicals, working around food, thorough site inspections, paperwork, etc. As much as I wanted to focus on Tony, Gina, our home, and the new living arrangements, I also didn't want to mess this up. I knew Tony had put a good word in for me, and I...

Training of Mistress' New Sub Day 01

by naughtyboy082 on Sep 19, 2017
BDSM

As Mistress Sharon has requested, a written story... THE FIRST MEETING MISTRESS SHARON sends out a late night text that her new submissive has been waiting for anxiously all week long as he sought to prove his obedience and worthiness. "Congratulations, sub! You have successfully completed your probationary period...official training begins in the morning...

Dr. Gaylove Pt. 01

by switchhitter420 on Sep 13, 2017
Transsexuals & Crossdressers

Dr. Gaylove, or How I Learned to Stop Worrying and Love the Black Load Pt. 1 ***** As I came back up for air, gasping and gagging and spitting all over the 10", stiff, glistening black cock in front of me - standing erect and proud for the whole world to see like a dark pillar of dominance, a symbol of manhood and all that is virility, dripping potent see...

Master and Four Subs

by totk6432 on Apr 17, 2018
Fetish

This is a fantasy written by myself for fun. It contains spanking, humiliation and fetish; if this bothers you please seek other authors. All characters are 25 years old or older. ======= The rule is simple: I ring the doorbell and let myself into Master Daddy's house. Susan, my 25 year old personal assistant, is with me. She is in charge of me at work. Sh...

French Lessons

by lipsticked on Sep 13, 2017
Fetish

I first saw the ad on the internet. The website was a listing of Dominant Women on the West Coast. Since I live in Los Angeles, I was checking out the pictures and information on local dominants. The one that caught my attention was unique. Madame Darcy was based in Paris. Her ad stated that she traveled to Los Angeles frequently and had family here. She re...