Becoming A Sissy Stories

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by thetoy on Sep 12, 2017
Fetish

My wife and I over the years had developed a relationship between Domina and submissive sissy that was utterly grounded in love. Indeed, that was the only thing that had allowed us to go as deeply into the perverse and bizarre as we had. She had a marvelous ability to anticipate just what I would be able to stretch to reach. I trusted her absolutely and deli...

I Learned My Lesson Well Ch. 03

by Angelscuck on Sep 2, 2017
Exhibitionist & Voyeur

Well the weekend had arrived. My Fiancé, Angel, had given me a complete makeover at the salon. I looked ridiculous in my maid's costume with full makeup, heels, stockings, garter belt and leach with collar. She looked amazing with her slutty makeup, hair worn up and completely naked under her trench coat. We were on our way to her gangbang. Her black maste...

AliExpress and Sissy Downfall Pt. 07

by His_fag_wife on Apr 9, 2018
Transsexuals & Crossdressers

Please for goodness sake don't read this story if extreme use of submissive males by dominant males and dominant females offends you. This is pure fantasy and at the darker end of the spectrum of stories on Literotica, please do not read if this is not your sort of thing. Otherwise I hope you enjoy the spiral of depravity. ***** Charlie was alone in the ro...

Movie Night

by lavskye on Sep 1, 2017
Group Sex

Samuel pulled his keys from his pocket and fumbled with them. He found the key just as he approached his vehicle. He opened the door, climbed inside, and started the engine, fiddling with the radio as he pulled away from his parking space. What a day it had been. His neck and shoulders ached from being so tense all day at the office and he was glad to be goi...

Sissy Girl Forever Pt. 02

by sissymissyct on Sep 18, 2017
Transsexuals & Crossdressers

No going back now. Mistress was going to be certain that there would be no turning back for me. Over the next few weeks she made certain that I used my hormone cream daily. No my breasts haven't started to grow yet but I could notice some slow down in hair growth. My male wardrobe seemed to be dwindling, with more camis, blouses, soft pullovers and ladies p...

Humiliated Sissy Husband Ch. 05

by rik581 on Nov 16, 2020
Transgender & Crossdressers

Max and Tonya walked in the front door after a morning outing in which Max spent the entire time complaining about wanting to go home. Max stood there wearing a little girls dress and high heels, with his wrist tied to his upper arms and hanging limply near his shoulders. His shoulders, waist and legs strapped extremely tight to the pole. They needed to be...

Black Cuckolding Journey Trois

by Samuelx on Sep 11, 2017
Transsexuals & Crossdressers

Salutations, my friends and devoted readers. Wanda Philogene here. Your favorite Haitian dominatrix, taking the beautiful City of Brockton, Massachusetts, by storm. Ladies and gentlemen, I have some good news. I've dumped Sean Prescott, my favorite white dude, on account of him becoming possessive of me. Sean and I were cool, and we had some fantastic sex, b...

Halloween Pool Party Pt. 06

by sissymissyct on Sep 14, 2017
Fetish

I was exhausted and slept until 5pm when I was awakened by a gentle kiss from Miss Annie. She took off my headphones and rocked my shoulder a bit. "Come on my sweet sleepy sissy, it's time to get you up and about. We have a fun evening planned for you baby girl". I rubbed the sleep from my eyes and saw Miss Annie's beautiful face looking down at me. "lets ge...

Becoming a Sissy Maid & Slut Vol. 03

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Seven: Another Day in Chantel's New Life. It's 7:30am and the alarm clock goes off. I awake to my first morning in my new sissy slave home and life as a sissy maid and slut. I get out of bed, stretch and strip nude for my enema and shower. My butthole still hurts from last night's gang rape session, but I won't protest, nor do I really wish too. In...

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...