Chastity Training Stories

41,592 results
Orientation
Length
Source
Infinite Scroll

Secrets of the Deep Ch. 06

by Lady Malachite on Sep 15, 2017
Sci-Fi & Fantasy

Lena dropped out of the helicopter and glided down and into the crowd, landing softly, despite dropping some thirty meters, though her large bare breasts whacked her in the face as she crouched to dissipate the momentum. Everywhere around, there were piles of flesh and blood, the likes of which were rarely seen outside the most brutal of televised massacres...

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...

Mistress Di

by justincbenedict on Sep 14, 2017
BDSM

Di gently stroked Trent's dick with her red nails. "You like that, Trina, you little bitch?" she whispered softly in Trent's ear. "Mama may want you to go suck some dicks for her later worthless little tranny-bitch." She lay next to Trent in her low cut blue velvet embossed chemise and scalloped lace trim. Trent, for his part was wearing pink stockings and...

A Slave Trainer Ch. 04

by HisSexKitten0908 on Sep 26, 2017
BDSM

Chapter 4 Another scream rips from the slave bound in front of me. The electric prod is sticking out of her ass, now turned off. I reach around her body, fingering her wet pussy. I step away from her, raise my arm, and let the whip fly. It streaks through the air, and with a crack lands on the slaves stripped back. Two, three, four times, I lash the whip, w...

The Playhouse

by LordJim on Sep 17, 2017
BDSM

The last few years have been a tumultuous ride as I begin to look at growing older. I suppose it's time I pass on some wisdom, perhaps, but frankly, passing on some stories of adventures seems just as profound to me! But these are not stories of mountain climbing or travels, unless you count explorations of kink to be 'travels'! Inheriting money changes eve...

First Time for Daddy's Girl

by JennaJay919 on Dec 17, 2018
Transgender & Crossdressers

I had been talking to him for a while now. This man. Daddy. Somehow the constant barrage of pornographic images and sissy hypnosis had taken a hold of me and brought me to the point where I had actually begun to develop a relationship with a man. I had never thought of myself as gay, or had thoughts about men. I was the typical A-student, moderately athleti...

Mistress Starla Proves Her Point

by justincbenedict on Apr 16, 2018
BDSM

Porky was weeping bitterly, and at the same time, his dick was straining, and quite excited. Who was this girl? Starla was his friend Spalding's cousin, and he'd seen how she enslaved him--Olivarius, the school's intramural lacrosse coach had told Porky that Starla had taught him how to suck his own dick... Several young women of Porky's acquaintance foll...

Star Wars Imperial Prostitute 3 Ch. 02

by HandcuffGirl on Sep 12, 2017
Celebrities & Fan Fiction

Authoress's notes: This is the fourth part of the story of Jaina Solo's transformation into Imperial Prostitute SX-51472. To summarize the story so far. . . After Jedi Knight Jaina Solo kills her twin brother, Darth Cadeus, she leaves the Galactic Alliance for the Empire, with her sometimes lover Jag Fel. Jag has just been made High Moff of the Galactic Emp...

Star Wars Imperial Prostitute 0 Ch. 07

by HandcuffGirl on Sep 12, 2017
Celebrities & Fan Fiction

Authoress's notes: This story takes place very soon after the end of the Second Galactic Civil War. It is a prequel to Imperial Prostitute SX-51472. Thanks to meathead96 for editing this entire story for me. Star Wars: Imperial Prostitute SX-51472 ZERO Chapter 7 of 8 A few days after realizing that she is SX-51472. . . "Hi Chief," Seventy-Two said with a...

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...