Strapon Sissy Maid Stories

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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...

Miss A's New Play Thing Pt. 03

by Pornenthusiest on Dec 2, 2019
BDSM

Alex, the 23 year old virgin, had just left his first session with his new Mistress, Miss A. He left chastised, blackmailed and with a new obsession with feet. Chapter One: The Envelope Alex had gotten on the bus, it was his first time in public wearing his chastity cage and he was very self conscious about it. He thought he could hear the lock click agai...

Miss A's New Play Thing Pt. 04

by Pornenthusiest on Mar 2, 2020
BDSM

Recap: Miss A had just finished a luxurious bubble bath and was returning to her slave who was chastised and gagged with her pantie hose and a ball gag, with Miss A's wetted panties draped over his nose. Locked away in her dungeon, after an arduous breath control play session, her slave was spread wide at the ankles with a spreader bar, bent at the waist wi...

Mistress Natasha

by maidevie on Sep 26, 2017
BDSM

The soft black and chrome leather bustier pushed Natasha's breasts upward to astonishing heights; the mounds of soft flesh trembled with every step that she took. John sucked in a deep breath as she walked towards him. She was truly a Goddess. Her legs were on display in black thigh high vinyl boots, the heels of which had to be at least 6 inches high and de...

Mistress Monique Pt. 02

by bleedndkn on Sep 25, 2017
Fetish

This wasn't even my fantasy, I thought as I purchased the clamps, butt plug, heels and maid dress online with expedited shipping. The next day I brought the items in a backpack to Mistress Monique's apartment while she was at work. I put everything on then placed the butt plug in my ass and tightened the nipple clamps painfully so they wouldn't fall off, th...

Unexpected Encounter Pt. 01

by cddream on Mar 6, 2018
Fetish

It was a week night and I received a text from an ex girlfriend I haven't talked to in 2 years. I stared at my phone in surprise when I see her name pop up. My heart kinda skipped a beat and I opened the text anxiously. It was from Molly, she was the first girl I exposed myself to. She knew all my secrets and kinks from our past together. The text simply re...

How I went from Domme to Slut

by Ms_Allison on Dec 7, 2017
BDSM

There are times in your life you wonder how you ended up where you are and today was one of them for me. I'm sitting here in a long satin robe in a very un-ladylike position with a bag of frozen corn pressed between my ass cheeks. Why corn? Because it molds pretty well into the space where you most need it and I need it against my very sore ass. First let me...

How I went from Domme to Slut Ch. 05

by Ms_Allison on May 29, 2018
BDSM

Over the following few months from my first night waiting tables at the club things continued and amber and I fell into a comfortable rhythm with things. The first Friday of the month amber would wait tables during "men's night" and on the third Friday of the month I would wait them for the Ladies. When amber waited tables I was typically dressed in somethin...

Helping Jess Pt. 03

by mski on Sep 18, 2017
BDSM

Sometime in the morning I woke up with Jess on top of me giving me a good morning kiss. 'Wakey wakey sleepy head!' she said with a huge smile. I grinned back, it was a nice way to be woken and she looked as gorgeous as ever in her red silk chemise. I started to get aroused but my penis was always going to lose the fight against the chastity belt. I grimac...

Adventure Night Ch. 01

by Pghwriter on Sep 17, 2017
Fetish

"Yes, Mistress, I understand." In truth, I didn't really understand. I didn't understand how it was I'd gotten myself into this position, but every time She spoke, I listened and did precisely what I was told. "That's a good slut," She said into the phone, and then it went dead. I sighed. Not even a "goodbye." As I drove home from work, I realized that I...