Whore Training Stories

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My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Proud No More Ch. 04

by Red_Anticius on Jun 19, 2019
Celebrities & Fan Fiction

Chapter 4: Archmage Subjugated Jaina Proudmoore could no longer keep track of the days that passed. Time blurred as one session with the Pride Breaker blended with the next. In between her so-called training, she was given 8 hours to rest. But all too soon, she would be brought before the dreaded goblin tech again, and forced to take it up the ass for anoth...

BDSM Training B&B

by MasterTJ on Sep 26, 2017
BDSM

My wife Courtney and I had no idea when we purchased the "Weekend Slave Training Course" at the Chateau de Sade that our relationship and lives would never be the same. Courtney and I were both in our early 30s, and had had a relatively happy marriage for five years. But after a few years, our sex life--always pretty vanilla--had become predictable and ver...

Initial Meeting

by Chrissy1066 on Sep 13, 2017
BDSM

As Missy was doing some soul searching after her relationship ended, she came across this gentleman that intrigued her. She not only noticed his nice physique but also something in his eyes, which she wanted to know more about him. She proceeded to email him and simply introduce herself. After a few emails and then talking on the phone the two agreed to me...

The Prostate Exam Pt. 07

by His_fag_wife on Sep 18, 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. After he'd given away his naturally submissive tendencies by pushing bac...

Zindy's Training

by slavegirlzindy on Sep 12, 2017
BDSM

My slave name is zindy, and my Master's name is Jeff, I call him Master. My first night of training was difficult but not unbearable. We had never tried Domination before, so we tried it our own way. When I came home one evening he took me to the bedroom, I knew what to expect we had e-mailed each other all day, and I was already dripping wet just from the t...

Welcome Home My Master

by MastersPrizedPossession on Sep 26, 2017
BDSM

Friday afternoon had me showing up at the airport, looking like a very expensive call girl. Heavy makeup, blonde hair long and flowing as he likes, short black skirt, white button up blouse, slightly too unbuttoned, my red and black half bra easily seen, my pierced nipples even easier to be seen through the white material. Black fishnet thigh highs and some...

First Time Sissy - The Bike Path

by Phillysissylexi on Jun 15, 2020
Transgender & Crossdressers

My roommates had gone away on a trip for a week, so I had the house to myself for a few days. I had been waiting for a moment like this. As soon as they left I went to my closet to find all my girly clothes, toys, makeup, heels, and lingerie. I couldn't contain myself. I was so excited to turn myself into a sissy. I turned on some sissy hypno to listen to wh...

Sharing The Puta Ch. 04

by MosheDovit on Jun 25, 2019
BDSM

"Good Slut! See how obedient this cock can be with the proper training! This slut can win many races for his lucky new owner. Who will start the bidding?" The audience of female buyers gathered closer after my performance on the milking table. Heather buckled a wide leather collar around my neck, clipped a short chain leash to it and pulled me forward. I cr...

Reinforcement

by skinnysailor on Jun 19, 2018
BDSM

I feel so elegant and sophisticated. My red hair has just been styled. I'm wearing my sexy spiked heels with the rhinestones that bring me up to five foot four. My shoulder-less red velvet gown is hugging my trim body to just above my knees where it flares out so dramatically to my ankles. My diamond necklace, pendulum earrings and two diamond bracelets, one...