Training Sissy Stories

41,670 results
Orientation
Length
Source
Infinite Scroll

Developing Emma Ch. 02

by Sputnik57 on Sep 19, 2017
Transsexuals & Crossdressers

She awoke to the sickly smell of a woman's perfume; the silky stockings were still there, but Emma was now naked apart from a chiffon negligee, her hands bound behind her back. The voice of the woman broke the silence. "Hello again 'Emma'; that's a very pretty name you've chosen for yourself, we shall soon have you worthy of being Emma, and you'll soon know...

Turning into His Toy Ch.02

by vaultdweller111 on Sep 13, 2017
Transsexuals & Crossdressers

I couldn't believe what was happening. I am on a plane flying from my home state of Ohio to Los Angeles to meet my new owner. It started when I met him on a gay chat room and told him I wanted to become a feminized sissy slut. We talked and before I knew it he sent me tickets to fly to California. I left my home in the middle of the night and left my parents...

Sissy Boi

by DrLuverotica on Sep 12, 2017
Transsexuals & Crossdressers

COFFEE "Thanks for me, Raquel, I'm at the end of my tether and I don't know what to do with Dan anymore." I was meeting Raquel, one of my colleagues for coffee. She knew I was struggling with my husband, but didn't know the problem was in the bedroom. "That's alright, Jo. My pleasure." "Look what I've got to share with you is deeply embarrassing, so I beg...

Miss Guided

by MissMarianne on Mar 12, 2019
Transgender & Crossdressers

My name is Susan and my husband Charles, we are both 25 years old and have been married for one year. Recently Charles has been very depressed and He lost his job when the company moved to Malaysia. Lately his performance in bed has been sub-par and , in fact, he can't get it up most of the time. We feared he was becoming impotent but the doctor said the pro...

From Her Ex-Boss to her Bitch Pt. 07

by His_fag_wife on Sep 25, 2017
Transsexuals & Crossdressers

Please do not read this story if fantasy is not your thing. This has scenes of outrageous levels of forced sissification, forced bi and gay scenes, watersports and general humiliation and degradation. It's just pure fantasy and includes some hypnosis. Some readers find these stories too full of fantasy, in which case please just don't read it. It had all st...

Joining the Ranks of Lady Bois

by eviltwin52 on Sep 14, 2020
Transgender & Crossdressers

This is a story about one man's transformation from loving husband to lady boi. His evolution began with a colleague leading him to an aggressive indoctrination. The journey takes him from the safe confines of a married Caucasian heterosexual male to celebrating his new life as Black cock loving lady boi. On a side note I have chosen to turn off the anonymo...

The Prostate Exam Pt. 04

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by not being able to resist pushing back against her finger, forcing her finger deeper into asshole. At that point his female doctor had decided to test just how submissive he was. She gave him the option to back out if he...

John Meets Sandra Ch. 5

by eeric on Sep 16, 2017
Interracial Love

If you have the time you can e-mail me and tell me what you thought. ***************************************** It has been a few months since I asked Sandra to marry me and she said yes. It was late in the afternoon and Sandra was getting ready to go to her bacholarette party. I didn't have that many friends so I wasn't having a stag party. When Sandra c...

Under Mommy's Direction Ch. 05

by MommysHypnoSissy on Apr 13, 2020
Transgender & Crossdressers

The rest of Jaime's day had been a whirlwind of tasks and chores to complete before his Mother got home. His online Sissy Trainer, who demanded that he refer to her as 'Mommy', had given him a myriad of tasks. First it was cleaning up his Mother's bed and sexy toys, putting everything back how he had found it. Then it was back to his room to dispose of his b...

To the Manor Bound Ch. 04

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This probably won't make too much sense unless you've read the other chapters first. Like the other chapters this includes forced feminisation, BDSM, and non-con, so it might not be your cup of tea. Regardless, do comment and email me to let me know what you think, or just to say hello! ***** Chapter 4 - Five Weeks After Transformation Peter held the d...