Crossdressing Maid Stories

15,364 results
Orientation
Length
Source
Infinite Scroll

Dressed To Please Kate

by jealouscuck on Sep 25, 2017
Transsexuals & Crossdressers

My name is William Michael. I go by Bill. I know, stupid way to start a story. My wife is Caitlyn and goes by Kate most of the time. You will see why I started with names. Kate is thirty and I am thirty-one. We had been married three years when all this started. Kate is a very perky brunette, five-four, about 130 lbs. She has very little body fat and is athl...

Erika's Story

by Quantarx on Jan 20, 2020
Transgender & Crossdressers

My name is Eric and I have been into crossdressing as long as I can remember. The feel of sexy silky woman's clothing has always been a real turn on for me. I honestly couldn't tell you when it started, but I can tell you it has progressed over the years. I have gone through my "pink Fog" phases where I would buy sexy clothing, only to be filled with shame a...

From a Husband to a Dutiful Sissy Ch. 11

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

The way this chapter turns out to be, I suggest one may need some tissues... Don't say I didn't warn you. ***** Chapter Eleven: Jack and Chantel, Life's Ups and Downs. I wake up to another new and exciting morning, It's cold out but sunny, Fall is soon moving to Winter. Out of my nightie and into the shower I am invigorated by the warm water. Getting out...

Changeling Ch. 05

by Michael142 on Sep 19, 2017
Fetish

Continued from Chapter 04, and concluded in this Chapter. Scene is in the townhouse, after David plays maid to Donna and Brenda. Donna and David are alone in the bedroom. ***** David dresses as my maid for a party. David and I made love long and ardently last night with lots of kisses and touches, giggles and intimate talk, and of course ... fucking! W...

Jeff Crossdresses More & More

by TurningintoCD on Sep 12, 2017
Transsexuals & Crossdressers

My name is Jeff. I date girls every now and then but I always masturbate about dressing up as a hot chick and seducing a hunky guy. My biggest turn on is putting on women's clothes and makeup. I never really had a chance to explore it much when I was growing up. In college I had a secret stash of 1 stick of lipstick, and when I felt really dangerous, I wou...

Escapism: The Modern Man

by chasingrisque on Sep 13, 2017
Transsexuals & Crossdressers

*Synopsis: 25, in and out of relationships and one-night-stands. In debt, slightly overweight, unfulfilled at work and in life. Sick of his friends and routine, Alex accidentally reawakens feelings he has not had for a long time. Think Trainspotting for sissies - American Psycho without the violence and lot more lace, lip-gloss and high heels.* ESCAPISM:...

Passion over Lust

by sarahchica96 on Sep 5, 2018
Transsexuals & Crossdressers

Introduction I' am living the dream, the dream of maintaining the balance as a regular straight guy and my bisexual crossdressing side Sarah. The 4 years of hard work at University started paying dividends, I landed a job as a legal advisor for one of the top businessmen in London Mr Hayat. My job paid well which enabled me to buy a studio apartment via a...

Ms. Rhonda's Finishing School Ch. 02

by hollygurl29 on Aug 20, 2018
Transsexuals & Crossdressers

DISCLAIMER: All characters in this and any additional parts of this story are all over the age of 21. This tale involved crossdressing and BDSM. If these subjects do not interest you then I wish you well and hope you find a story on the site which you will enjoy. If you choose to read this tale then I thank you in advance for doing so. When you have finish...

The Futa next door

by Abusedbyfuta on Jan 11, 2019
BDSM

You have lived in the same l cul de sacyour entire life. It's not a bad place to life, very much a part of suburban America. It's just not very exciting. You live in a large White House that looks the same as all the others on the street, probably a ploy by the developer to keep costs down. Every day you see the same boring neighbors, have the same boring ro...

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Sexual Scenarios

by zig322 on Dec 7, 2019
Fan Fiction

What we have here is a series of sexual scenarios from anime, cartoons, comics, tv shows, video games, movies, and even some original ideas. These scenarios will involve: spanking, ENF, forced feminization and crossdressing, foot fetish, tickling, LGBTQ, mind control, incest, any other perverted thing anyone can think of, and of course sex (consent or non-co...

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