Sissy Maid Chastity Stories

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Orientation
Length
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Infinite Scroll

Rubymoon Private Asylum Pt. 04

by Tombescent on Sep 14, 2020
BDSM

The patient had been in the custody of Rubymoon for a little over four months. It had been some time since anyone had thought of it as "Dr. Smith". A C note had played hours ago, indicating the patient should be still. It knelt in the center of the room, staring blankly, not daring to so much as scratch an itch lest it provoke the buzzer. The patient was a...

Sissy Chantel, New Reality Ch. 09

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Nine: It's Friday, I Have a Full Shift to Pull Today and Tonight. At 7:00am sharp we are all waken up. This is our daily wake up call and soon sissy Traci as our dorm room's head sissy maid has us all up and ready to go to our morning routine which will be a group enema, group shower, shave face and when need be the rest of our body hair then to do...

To the Manor Bound Ch. 01

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

[Hey, just to be forewarned, this story focuses heavily on forced feminisation including aspects of BDSM and non-consent, so if that's not your thing this might not be the story for you. I also feel the need to point out that I don't agree with any of Lord Madison's political views: this is porn, not polemic. With that said, I hope you enjoy it!] Chapter 1...

The Captive Prince

by PrinceCai on Apr 3, 2020
Fantasy

Marcus was reading in bed when his kingdom fell. It was over an hour past his bedtime, but the young prince wanted to stay up and finish his book by candelight. It was way too exciting a story to put down, all about a brave and noble lady knight who saved a peasant boy from the clutches of an evil sorceress. He had his heart in his mouth at the thrilling act...

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A Jamaican Vacation Ch. 04

by sissyashley4bbc on Dec 24, 2019
Transgender & Crossdressers

Rebecca studied me up and down. "What happened to you?" She asked. "I...uh...I..." Ty cut me off, "you look like you are in shock Rebecca. Let's fix you a drink and I'll explain everything to you." "Make it a double," she said as Ty started to make her a screwdriver. He handed her the drink, grabbed a joint, and ushered us outside. Rebecca sat down...

Caitlin and Mistress Vicky Ch. 03

by Jemina004 on Sep 19, 2017
Transsexuals & Crossdressers

I was sitting nervously in front of the mirror in the newly decorated guest room. Chad was set to arrive in half an hour. My wife was getting ready in what was for now our bedroom. She had told me to dress up for the occasion, though I was still to wear my maid's outfit. I opened my jewelry box and tried to decide how to accessorize. I selected a lace choke...

Revealed to My Roommate Ch. 01

by gaildaniels84 on Jan 6, 2020
Transgender & Crossdressers

Paul watched the clock on the office wall with rapt attention. He'd finished his work hours ago, the truth was doing the minimum at this dead-end office clerical job didn't take more than a couple hours of hard work a day, and since then he'd tried everything to distract himself. He'd been to the water cooler a suspicious number of times, taken several bathr...

Lace and Love Ch. 02

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Dan had a quick shower, brushed his teeth, and after giving himself an enema he started the process of becoming Alice. He stepped into their bedroom and opened the small walk in closet revealing men's clothing for him and Jake, Jake's old uniform from the marines, some various camo and tactical clothing Jake wears for his firearms training business then came...

Truth or Dare Takes a Turn Pt. 01

by Cutiepie183 on Sep 14, 2020
Transgender & Crossdressers

I'm sitting at home on summer break, just a few weeks after graduating high school. I hear my phone buzz and glance over to take a look. I can't believe what I'm reading! "Luke Elwood has invited you to his event: graduation celebration party tonight at 8pm." You see I was never really one of the cool kids in high school - I never really had any friends but...

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...