Toilet Sissy Stories

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The Training of Sissy Paula Ch. 4

by submissive~pet~ on Sep 14, 2017
Fetish

Mistress Carolyn Found the biggest cock she could find. He had to be 16 inches and his cock was fatter than my wrist. He told Mistress it takes him around 4 hours to cum. Mistress told me she would not make me try to swallow his big cock, but it would be visiting my asshole that night. I was dressed in my red velvet mini, no panties, silicon breast as big a...

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...

Caught in the Toilet

by Dennis_St_John on Sep 14, 2017
Transsexuals & Crossdressers

Kneeling on the floor beside the toilet, dressed in lingerie and wearing pink lipstick waiting for the door to open, my mind kept going around in circles to what led me here, wondering if I could have done anything different to prevent it. I remembered sitting on the toilet earlier today looking at my bright pink nylon and white lace panties, resisting the...

Mistress Commands Me in the Office Pt. 03

by Tracy69 on Dec 3, 2019
Transgender & Crossdressers

First a little clarification, if you've been reading parts one and two (I hadn't kept this quite straight up to this point). Here are the correct character names: Bob, or Robert, or Dick (or whatever my mistress decides to call me): Me Rick: My boss Brad: An office co-worker Rod: Office co-worker in an adjacent cubical, very buff, quite manly Wilson: Of...

Recruiting of a Sissy Maid Ch. 02

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Two: Onto Her Training and Breaking Down. The feeling of fear and dread falls over Chantel as she sits on the flimsy bed in what is for now her prison cell. Totally alone and isolated except for the fact that Mitch and Nate Burrows will lord over her as they orientate, train and ultimately break Chantel from a fantasy sissy to what will be a living...

Another Seedy Bar

by Stillherer on Sep 16, 2017
Transsexuals & Crossdressers

I carefully peek into the dark smokey interior of the rather seedy bar You have directed me to. A rush of gratefulness tingles my skin as I see that You are sitting there. Impishly I slowly saunter up to Your table giving You and all the others ogling my lithe body in my sexy outfit a show. I smile seductively, coyly dropping my chin waiting for You to offer...

Neighbourhood Terror to Sissy Pt. 17

by Fibaro on Feb 3, 2020
Transgender & Crossdressers

Chapter 19 The drive back home was pretty uneventful, Lisa just sat behind the wheel smiling ear to ear. She had had an awesome day so far, making out with two gorgeous women and now she would spend some quality time with her sissy boyfriend. Marcy was very worried about that quality time. She hoped for sure that it wouldn't involve that dildo going up her...

The Prostate Exam Pt. 03

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 pushing back against her finger, his female doctor had decided to test just how submissive he was. She gave him the option to back out if he didn't want to go any further, but she told him that if he did want to go furth...

Auntie Jean Drummond Lloyd Ch. 4

by Sissy Adele Howells on Aug 31, 2017
Fetish

The final humiliation by Auntie Jean Drummond Lloyd was reaching its very kinky conclusion. I was looking really cute in Karen Lloyd's pink pyjamas. I could smell Karen's perfume and bodily juices on them. Karen had even left her shit stains in the ass part. I was now paraded in Auntie Jean's bedroom. Kimberley Holmes, laughed at my blushing face. Her black,...

Mommy's Boy? Ch. 02

by yr_sissy_toy on Sep 13, 2017
Transsexuals & Crossdressers

I skipped home from school, an expression of the giddy joy I'd felt for the last week. I'd gone from a pansy boy who got teased after school to my mommy's special sissy, who was swathed in the finest femininity the moment I got home. It was delicious, intoxicating even, and I was almost bursting with joy. I'd learned so much in the last week! I could slip i...