Male Maid Training Stories

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Orientation
Length
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Infinite Scroll

Lady Bird

by N_Deavours on Sep 15, 2017
Fetish

A man is ordered to present his charms to a wealthy woman. "Excuse me Ma'am." "Yes?" Even though he was enormously agitated by the sudden turn of events the strong suppressant still worked efficiently, allowing for only an indistinctly red shade to be visible in his handsome face, noticeable only by the most attentive of aficionados. Only moments ago his...

Saleria Tales - The Bodyguard

by Zalminen on Sep 12, 2017
Sci-Fi & Fantasy

Taking one small sip from his waterflask Rasan tried to ignore the conversation of the two women sitting at his table. Once again his eyes scanned the surroundings. The common room was nearly empty, only a couple of travellers debating about their next destination and a group of men shooting dice and telling dirty jokes. Still, appearances could be deceiving...

The Slave Ch. 01

by jim313 on Sep 12, 2017
BDSM

I trembled with anticipation as I searched my pocket for the key to the postal box. I could see a small pink envelope with feminine handwriting through the window and couldn't wait to get at it. It had only been five tortuous days since I answered that ad but it seemed like months. As I opened the box, I clearly remembered the ad, "Male slave wanted by supe...

Twist

by Seurat on Sep 12, 2017
BDSM

Once, long ago, I got fed up with the way femdom, forced transgender, and loving wife stories with BDSM basis ended; they had grown very predictable. In fact, a few authors had posted short lists of vignettes which, unintentionally, encompassed all of the common endings which I had grown to abhor. My own list, a response to the predictability of those storie...

Sissy Chantel, New Reality Ch. 10

by Sissy_Chantel on Sep 15, 2017
Transsexuals & Crossdressers

Chapter Ten: My First Saturday and Sunday as They are Special Days For Us. "Wake up girls." as sissy Traci calls out to us. We all rise from our sleep and another day in our sissy maids, sissy sluts lives begins. Just like in the previous days starts we spend our time with a morning enema, shower, shave and makeup. We get dressed but not in any maids out...

Maid to Order

by dreadknots on Jul 30, 2019
Transgender & Crossdressers

Hi! Another story! Yay! This one is a little softer, in the same vein as The Girl Inside. If you're looking for hard fuckin', this might not be for you. Definitely for folks who focus more on the crossdressing aspect and bois kissing bois. This is told in the 2nd Person too, and assumes you are a boy at the start. Just a heads up! Anyways, please enjoy a bri...

Ella's House of The Way Forward Ch. 06

by Sputnik57 on Sep 18, 2017
BDSM

Gray had a stiff erection as he witnessed the transformation of submissive male to a more than passable female; it was not the transsexual form that excited him, so much as the crushing dominance of the women in their complete remodelling of the male persona, and the profound pleasure they showed in destroying the will. As Elsa whimpered like the girl she no...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

Ella's House of The Way Forward Ch. 03

by Sputnik57 on Sep 18, 2017
BDSM

Will was in a strange trance-like state as he was led from the assessment room; he was told to put his trousers and shirt back on, he did so; he was told to go with the lady outside who had been summoned by bell-pull, he did so; he was told to strip again whilst overseen by three stern women in the bath-house, he did so. Will had not been imprisoned, but fel...

Crossdresser Gets Found Out Ch. 03

by leathertanya on Sep 16, 2017
Transsexuals & Crossdressers

This story is fiction and is written for my pleasure and any comments or suggestions that anyone would like to make. Any suggestions through the link below. I adore the feel of leather, rubber, pvc and anything silky so it was no surprise to me that at an early age I liked the feel of certain female clothing. I am a perfectly straight male but my fantasie...