Sissy Maid Toilet Cruel Wife Captions Stories

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Truth or Dare Sissy

by maxy007 on Sep 12, 2017
Transsexuals & Crossdressers

It was your usual high school gath. At the time I was just an innocent 18 year old enjoying life with some friends. My name is max, and this is the story of how a small 20 person gathering turned me into a sissy. It was mid-year of the final year of high school, and my friend Isabel was holding a gath on Saturday night. It was a welcome break from study, a...

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...

Mistress Monique

by bleedndkn on Sep 25, 2017
Fetish

I met Monique at a show. She wore a tight black dress, dark eyeshadow and was by far the hottest girl at the venue. I didn't have a chance. A mutual friend introduced us and I became immediately enraptured with her and in the days to come would constantly think about how to spend more time with her. Then, after an evening with Monique and mutual friends at...

Bootlicker

by GoddessVictoria on Sep 25, 2017
BDSM

BE CAREFUL WHAT YOU WISH FOR. He remembered that later, much later but by then it was too late. By then every semblance of masculinity had been totally stripped away from him. He was no longer master in his own home. How could he have been so foolish? Had there been a part of him that hoped she would find out? He had been so careful, smug even. Why shouldn...

A Perverse Plan

by Candyboi on Sep 25, 2017
Transsexuals & Crossdressers

It started off with little things, small suggestions, that quickly snowballed into perversion. My wife Carla, who for the first decade of our marriage displayed little interest in kinky sex games became a hot wife virtually overnight with total control over me... Carla is 44, has a very curvaceous ass, 34DD tits, and works as a doctor at the local hospital....

From a Husband to a Dutiful Sissy Ch. 04

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

A quick note about this chapter. It runs a tad long as I want it to really set things up for Chantel's future, not just some sissy maid for her now Mistress wife, as cool as that can be, but to develop a more varied sissy, crossdressing, maid and slut story. I hope it works for my readers. ***** Chapter Four: Moving on to reinforcing my new lifestyle Satu...

Humiliated Stable Sissy Pt. 02

by SissyTwinkleToes on Oct 5, 2020
Transgender & Crossdressers

I woke up exhausted at the crack of dawn to Fairy Godmother obnoxiously clicking her fingers next to my ear. I minced downstairs, still locked into my ultra prissy outfit (where was the key?) and my totally exposed diaper, already damp from last night. I shuddered as Fairy Godmother ordered me out into the back garden, where I stood and curtsied to the risin...

Helping Jess Pt. 05

by mski on Sep 25, 2017
BDSM

I slept well that Sunday night which surprised me, though I guess I was probably exhausted. I woke up with my normal hard-on a bit before 5am, well it would have been a hard-on but for the cage. My penis was certainly trying. I never found it an uncomfortable feeling, just frustrating that there is no ending and I could not jerk off, and now who knew what wa...

Ultimate Sissy Weekend Ch. 06

by SissyTwinkleToes on Feb 4, 2020
Transgender & Crossdressers

Susie wonders if she'll ever get used to the horn honks. The gasps. The shouted comments. The whispers. The cruel laughter. She is stood with her sissy sister, Tinkerbell, in her pink OTT sissy dress she's been trapped in for over two days now, on the corner of the bad neighbourood where she now lives. It's 7:45, and she's been stood in public for almost two...

Sissy's Decline into a Slut Pt. 01

by Sissy_Chantel on Sep 13, 2017
Transsexuals & Crossdressers

Hi, readers, here is a new hopefully erotic story series of a sissy's decline to that of playing a sissy slut and then without her knowing soon to be a enslaved sissy maid and slut, featuring your sissy girl Chantel. Enjoy... ************************ Chapter One: Sissy Crossdressing Play Time. I'm sitting inside my car, it's late, a faint drizzle falls a...