Crossdressing Maid Stories

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Infinite Scroll

Sarah Gets to Write Her Own Story

by SarahCD on Jan 6, 2020
Transgender & Crossdressers

If you are an adult, looking for some kinky fun, live in the San Francisco peninsula and would like to star in a re-enactment of one of my experiences, contact me. My experiences here show what I like to do. We can write our own scenario and then act it out. I'd love to help you make your fantasy a reality. Now for my latest adventure, I found a Classified...

From a Husband to a Dutiful Sissy Ch. 04

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

A quick note about this chapter. It runs a tad long as I want it to really set things up for Chantel's future, not just some sissy maid for her now Mistress wife, as cool as that can be, but to develop a more varied sissy, crossdressing, maid and slut story. I hope it works for my readers. ***** Chapter Four: Moving on to reinforcing my new lifestyle Satu...

Laundry Date

by Rallynoangels on Nov 27, 2017
Fetish

This story contains light femdom, humiliation, and crossdressing themes. All characters are 18 or older. ***** She did enough housekeeping at work, and now her Friday was taken away from her because of even more cleaning. Four year degree and what did she get out of it? A stereotypical maid's salary at a hotel that paid just enough for her to live in a ru...

Jolene's Momma Pt. 02

by ValoryG on Oct 6, 2020
Transgender & Crossdressers

After Brandi left, after I had willingly signed my privileged life away, I also had some nagging fears. Like, would Jolene be able to carry out her role, since she was usually so sweet and caring, and she usually gave in to what I wanted? Or would she take after her mom and become a merciless taskmaster and sadist whom I would hardly recognize? After we ha...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...

Staying Together

by komrad1156 on Sep 12, 2017
Transsexuals & Crossdressers

"I'm not sure further sessions will be of much use to either of you. After seeing both of you twice of week for two months, neither of you is any closer to resolving your concerns than we were when you first came to me." Dr. Nelson was good. She had the ability to examine a problem, bound it, and then dissect it into smaller pieces. She'd done that with bot...

Recruiting of a Sissy Maid Ch. 09

by Sissy_Chantel on Oct 31, 2017
Transsexuals & Crossdressers

Chapter Nine: Things Begin to Change for Chantel. Morning time, Chantel awakens and takes a moment to realize where she is and all that has happened. She sits up in the bed and looks over and sees Carl Luftgrin, her mind balances between the thoughts of a wonderful date last night with Carl and knowing this man as her Master owns her. Her mind battles these...

Becoming a Sissy Maid & Slut Vol. 02

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Four: My Arrival and a New Start to Full Time Sissy Life. I awake about 7:30am, groggy as I only had a floor to sleep on with a thin blanket, I rub my morning eyes as I sit up and see the black, satin, maids dress on a hanger, as if it was calling me to put it on. I soon realize my new predicament and smile. I had to take off the pair of pantyhose,...

An Ever Changing Story

by Helenthemaid on Sep 16, 2017
Transsexuals & Crossdressers

Caught Out and Permanently Punished I was wearing a ultra short black leather mini skirt, a tight leopard print low cut top, which revealed my cleavage entrapped by my pink lacy bra (with matching panties). The straps of my 6 inch leopard stiletto heels were securely padlocked around my ankles. Recently I had been often going to the local park dressed in...