Maid Outfit Stories

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Dick Size Bet

by alexmuntz109 on Apr 28, 2020
Transgender & Crossdressers

It was a Saturday, and I had nothing better to do than lay in my bed in my dorm room, watching TV. Suddenly, I heard a quiet knock at my door, which I initially ignored, until the quiet knocking turned into banging. Lazily, I got off my bed to answer, and was greeted by my friend Sam, who I had been regularly hanging out with since the start of the year....

From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

Holly on the Clock Ch. 01

by Moxon4 on Sep 13, 2017
Transsexuals & Crossdressers

Holden had become accustomed to being the woman of the house. He had always been very neat and clean, and didn't mind cleaning the house for his wife. It was a Friday night, and he was already in his maid outfit and feeling like Holly, his alter ego. The outfit had frilly lace edges and white stockings with black heels that were now 4" high. Tricia came home...

Gone Fishing

by tgirl_Mary on Sep 12, 2017
Transsexuals & Crossdressers

The divorce was not going well for me. Caroline got the house and the car and a most of our money. Worse than that was how she manipulated the whole thing. She told me, "You're a pathetic excuse for a man Carl. You never could satisfy me. Size does matter and you are sadly lacking. I always faked it with you. The other guys I fuck are all bigger than you and...

Polish Maid

by johnnysdirtysecret on Sep 19, 2017
Transsexuals & Crossdressers

'You want to get tips,' I explained to Marek, our Polish cleaner, 'You should be more a maid more like her.' Across the street was a girl of about 19, dressed in a fancy dress French maid's costume stumbling home, presumably from a party the night before. She was dressed in a tiny black dress, low cut with a short skirt, white apron, stockings and heels. M...

A Christmas Tail Ch. 03

by Angelscuck on Sep 13, 2017
Transsexuals & Crossdressers

The following story is written by my wife Angel. It is her view of the slave auction night plus my night as her slave and what she made me do. As I rode home in our car that night, a bit dazed, and reflecting on what the hell had just happened, I was surprisingly pleased with myself. I really had showed, mostly to myself, but also of course to my husband...

The Spanking Couples CFNM Party

by reddbunnz on Sep 17, 2017
BDSM

Chapter One: Two days after one of the monthly Spanking Parties, Debbie and Marion were sitting in Marion's home office discussing their sexual appetites. Both were dressed as normal when relaxing in one of their respective houses. Both had casual clothes – for them, at least. Both sported normal, everyday bras and tops, but were butt naked below the waist...

Devoted Cuck Ch. 02

by cuckyfucky on Dec 18, 2018
Fetish

This is Chapter 2 of my ongoing series. Chapter 1 can be found in my profile. ***** I was cleaning the kitchen in my sissy maid outfit when the phone rang. Seeing it was Lina, my wife, I immediately picked it up. "Hi cucky, are you finished with your chores?" she asked. I could hear music in the background and so I knew she was still at the club. "Yes L...

Bobby and Abby's Amazing Adventure Ch. 07

by emelle78 on Nov 4, 2019
Transgender & Crossdressers

I stayed with Ted in his hotel that night and got home mid-morning, after Abby and Clark had left for work. Just as I got home the phone rang. "We got the job!" Abby screamed into the phone. "Yes!" I cried out. "Congratulations!" Abby told me that Ted received three almost identical offers, but 'Bobbie' made the difference. "You were the key, baby!" sh...

A Bet is Maid

by jerrycross on Sep 18, 2017
Transsexuals & Crossdressers

Well let me begin, by starting to tell you on how I got myself into the mess that really changed up my marriage. I was doing nothing really, just playing some video games and lounging around. As my wife Angie was buzzing around the house, I could tell she was getting a little fed up with me just laying around. Our playful relationship has always been great a...