Sissy Maids Stories

10,558 results
Orientation
Length
Source
Infinite Scroll

Sarah went to Work at a Hotel

by SarahCD on Dec 19, 2018
Transgender & Crossdressers

By now, I had been working as a maid in a hotel for a few weeks. It was an LGBTQ friendly place and so I got to wear my French Maid's outfit while working. I loved walking around being seen dressed as a girl and not just dressed as a girl but wearing a sexy maids outfit. I knew that my suspender straps showed and I loved to show glimpses of my panties. The p...

Mommy's Boy? Ch. 03

by yr_sissy_toy on Sep 13, 2017
Transsexuals & Crossdressers

I minced into the kitchen in a new dress, feeling terribly nervous. My small pink butt plug added somewhat to my wiggle, reminding me at every step that sissies need constant training. I brushed my hands against the skirt of my princess dress one more time, smoothing out again all the wrinkles that my imagination created, and again touched the hair of my wig...

Bird of Prey Ch. 05

by Sputnik57 on Sep 11, 2017
BDSM

Gordon watched the pencil-skirted Penny strut into the house with her attaché case, drop this into a chair and strip. She smiled broadly as she returned across the lawn, naked, as though this were routine. Gordon's back stung like hell but his cock rose as even the scent of the three naked women took control of him now. The assertive blonde smiled down at th...

Transforming Brent Pt. 04

by sissymissyct on Dec 2, 2019
Fetish

In the morning I showered and dressed casually as directed by Mistress Wendy. My new black skinny jeans and a plain blouse with light day make up and my cork wedges. Some jewelry and my handbag and I was ready. Mistress wore leggings and a tunic top with her long hair tied up in a bun. Wearing flats, she was still much taller than me. We had a light breakfa...

Dr. Hottie's Story

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

Stuck in my office again. Tired, stressed, hungry, a little bored...I hate admin. Working as a doctor has its rewards. But the long hours and endless paper-work are not one of them. Hubby, though he's patient and understanding, is getting increasingly frustrated. It's affecting our intimacy - especially our sex life which is now frequently no more than once...

While You Were Away Ch. 02

by SweetsFW on Sep 16, 2017
Transsexuals & Crossdressers

I felt like a pig shat in my head. A bastard of a big who stole the moisture from my mouth while he was at it. My body slowly, groggily, reminded me that this was a hangover. For a moment I hadn't a clue where I was - I had planned to go home last night. I rolled over to check the time, and it was the jabbing in my ass that reminded me. Mortified I pulle...

FILF (Fathers I'd Like To Fuck) Ch. 03

by Angelscuck on Sep 17, 2017
BDSM

A couple of weeks had passed since our last adventure and I decided it was time to further Sandy and Shelly's sexual education. They had called me several times during the last week and I knew they were anxious to have their next lesson. This time I had planned something very hot. While teaching gymnastics at the alternative high school several years ago...

The Life and Fantasies of a Sissy!

by gasissynora on Nov 6, 2018
Transgender & Crossdressers

The following story is partly true and partly fiction. The names have been changed to protect the guilty. I hope you enjoy the story as much as i did living parts of it and wishing i had lived the rest of what is here. ***** A number of years ago i saw an ad from Mistress Kay and was fascinated by what i saw and read. After thinking about it for a while i...

Mark to Mary Ch. 01

by trannyslut on Sep 16, 2017
Transsexuals & Crossdressers

It was about 8 a.m. Friday morning when I pulled up to the house and turned off the car. I checked the address and was sure this was the house. This was the house of Mistress Amanda. I had been talking to her for several weeks and had agreed to be her sissy made for the weekend. It was a secret fantasy of mine that I had kept hidden for years. I was so lucky...

Hotwives Ch. 02

by Donna Williams on Sep 16, 2017
Transsexuals & Crossdressers

HOTWIVES II by Donna Williams ((Read the first part of the story in "Hotwives" first)) I was now a hotwife, Vicky was a pseudo hotwife, and John was a sissy, cock sucking cuckold. Everyone got what they wanted, if not more! * * * Once John had fallen asleep, Dave and Rick left as we had planned. When John woke that morning, he found me in the shower. "You...