Male Maid Training Stories

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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...

At Her Disposal Ch. 01

by Sputnik57 on Sep 15, 2017
BDSM

He had remained a bachelor, blaming the rigours of his working life which had often seen him travel to the corners of the British empire on business as the reason for not taking a wife, in response to those who cared to ask. The real reason for Henry Trent remaining single at nearly 50 - he being a more than reasonably well off Victorian gentleman, fit and a...

Ella's House of The Way Forward

by Sputnik57 on Sep 18, 2017
BDSM

As the year 1880 wore on, Gray's urges toward women of a certain disposition grew stronger. As the owner of a modest drapery shop just off the Strand, he was fortunate in one sense to in contact with many women, though this did not help what he viewed to be a very unnatural desire; whilst the two younger male assistants at the shop discretely displayed their...

The Club Pt. 06

by RubberBudcus on Sep 16, 2017
Transsexuals & Crossdressers

Chapter 10 What's in a name? I think I must have slept literally as I fell on the bed. As you know there are no clocks here at FemsRace and time passes according to your whims and pleasures. I awoke laying demurely on the bedclothes but cursed my luck that my blouse and skirt would be creased. I rose and checked in the mirror. Sure enough, my skirt and bl...

And So to Bed

by mshsrfc on Aug 18, 2017
Fetish

The Original. Dear Sir.--The year 1886. The scene, a fashionable drawing-room. The time, 9 p.m. A tall, graceful woman, and a pretty girl of 18 or 19, are reading the latest fashion news. Looking at the clock. The elder of the two says, "Come, dear; It is time to dress for bed." One readily imagines the outburst of merriment with which the modern flapper...

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...

March Madness Ch. 03

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...

Sissy Chantel, New Reality Ch. 09

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Nine: It's Friday, I Have a Full Shift to Pull Today and Tonight. At 7:00am sharp we are all waken up. This is our daily wake up call and soon sissy Traci as our dorm room's head sissy maid has us all up and ready to go to our morning routine which will be a group enema, group shower, shave face and when need be the rest of our body hair then to do...

Slavery Begins at Home Pt. 03

by Wifeowner on Nov 2, 2020
BDSM

***AUTHOR'S NOTE; Semi-consensual depravity ahead. This story contains elements of coercion as the two slaves are ordered to assume their new roles in a most unconventional household. Boundaries are tested and egos are broken. But they all live happily ever after.*** The slave named Cum Hole waited patiently for his master to fuck him. After assuming the...