Maid Outfit Stories

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Orientation
Length
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Infinite Scroll

Maid for her Pleasure

by grgy56 on Sep 17, 2017
BDSM

It took me all morning to thoroughly clean the house as Mistress desired. It sparkled as the bright sunshine beamed through the windows. Mistress always preferred me to be properly attired when I do maid work. Mistress was generous enough to allow me to purchase a French maid outfit. The top part of the dress was a form fitting bodice laced up while the sk...

Magic Dress - Diana Pt. 01

by SlightlyRude on Apr 23, 2019
Transgender & Crossdressers

THE BEGINNING Shit! I thought. Oh fuck! Buggeration! Damn and fucking blast! Here was I a happily married man, standing in a dress. A real woman's dress. And I liked it. I really liked it. It was fucking wonderful! "Oh," I said. "What was that?" said my wife Gwen, just adjusting her moustache. "It's surprisingly comfortable," I answered weakly. "Hmn,"...

The French Maid

by lovinlife0828 on Sep 13, 2017
Erotic Couplings

It had been a busy Saturday morning at work, and I was looking forward to getting home. You see, Saturday is the day that the maid cleans the house. I like to watch her as she goes about her duties, and today would be no different. I do have one rule though. I do require that the maid wear a French Maid Uniform. I find it very erotic to watch her flitting ab...

From a Husband to a Dutiful Sissy Ch. 05

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Five: I'm going to be more than just a sissy maid. Waking up Sunday morning, I sit in my bed and think about my slut duties last night at the rest area. I get into the shower and it all floods back to me as I shower, then dry off, moisturize and get back to my maids quarters and do my makeup, put on my bra, panty and maids outfit, black one today wi...

The Chair Ch. 21

by Rickd_1960 on Sep 16, 2017
Group Sex

Her birthday was quickly approaching and he had yet to come up with the perfect present. This was difficult because he continually showers her with gifts, not just on special occasions. But he wanted her birthday to be special. After all the pleasure she had brought him over the past several years, first as one of his favorite dancers, and then as his muse,...

Two Girls In Sexy Outfits

by Stusion on Sep 13, 2017
Group Sex

Special thanks to Ruthie_272 for editing my first story. Many thanks! ***** Megan and Nicole are two very lovely girls I know. Megan is my darling girlfriend which we have been going out for about two years. Nicole is Megan’s best friend from High School, very friendly and happy person who is currently single for a few months now. The girls are very n...

All Right I'll Do It Ch. 03

by LaurenWestley on Sep 15, 2017
Transsexuals & Crossdressers

(Authoress Note: of course all disclaimers are still in place regarding characters etc., except for one small truth since so many readers have asked me to answer this question. Many of the things I've written about I did at some point in my life. There are more characters in these stories and events never happened such as these stories. I am also sorry for e...

The Ant Woman Ch. 10

by DreamerByTheDiamonds on Aug 21, 2019
Sci-Fi & Fantasy

The Sunlight Temple was an appropriately bright place. The supporting beams and columns were blood red, but the many roofs had blue and yellow colors. The walls were white with thin carvings of trees, flowers, birds, and dogs. Gentle, sweet incense was burning as the Empress Dowager and Wen knelt before a statue of an elven god and silently prayed, holding p...

Caught

by ImpureChastity on Sep 13, 2017
Transsexuals & Crossdressers

I had been planning my downfall for weeks. Putting together the right outfit, working out the best place to be in the house, practicing my lines to appear convincingly surprised, everything was lined up perfectly. For a few months the relationship between me and my fiancé, Janice, had been just a little kinky. She had cottoned on to my submissive tendencies...

Anything For You Ch. 3

by LR on Aug 31, 2017
Fetish

It was now three days after the first night with April/Jim. I was still not sure how I felt about that encounter. It is not every day that a teacher has sex with a 19-year-old she-male former student. Especially one that basically blackmailed me into doing it. I have to admit though, by the end of the evening I had enjoyed our sex filled night. April had lef...