Sissy Maid Spank Stories

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My Father, The Maid

by SissyOona on Oct 16, 2018
Transgender & Crossdressers

I thought it was really weird when I received the random text from my step mother, even though I had known her for most of my adult life as my father's new wife we had never really been close. Hell, for that matter I had never really been close to my father either, he was always pulling long hours at the office when I was young, so he was never around. Nowad...

Girl's Night Pt. 03

by DifferentBreed on Sep 14, 2017
Fetish

Fisher climbed the stairs slowly, wary of the quiet that hung over the upstairs. As he hit the landing a soft moan emanated from the bedroom and his heart raced as he entered the doorway. There, framed in the soft light of the bedroom lamps, was Sophie kissing another woman. Her crisp white shirt was unbuttoned, exposing the top of her supple breasts, and gi...

Erin Ch. 15: Perfect Sissy Cuckold

by Graves94 on Nov 16, 2020
Fetish

Erin Ch. 15: A Perfect Sissy Cuckold By Jonathan Quincy Graves {Note: This is the fifteenth in a multi-part story series cataloging the progressive evolution of a relationship between a dominant woman who provides leadership and discipline for her husband. Each installment can stand alone, but they read much better if you start at the beginning. Go to: Eri...

The Holiday Pt. 01

by mandiejune on May 16, 2018
Transsexuals & Crossdressers

My name use to be Frank its now Helen sissyslut and I was surfing web looking at crossdressing sites on my computer when this holiday competition came up. For some reason may be my wife had left me after finding me dressed up like a hooker! I decided to enter the competition not really expecting to winner a free 4 weeks holiday in South of France. Two weeks...

Girl's Night Pt. 02

by DifferentBreed on Sep 14, 2017
Fetish

Fisher was upstairs, making the bed when he heard the front door opening, signaling Sophie's arrival home. He looked down at the list on her dresser, frowning. He had not completed four tasks. He reapplied his pink lipstick and kissed the paper above the words "make bed with gold satin sheets" as he was instructed. He then scurried downstairs, incomplete lis...

Intervention

by Angelscuck on Sep 13, 2017
Transsexuals & Crossdressers

My fiancée's girlfriends were becoming a little apprehensive about the changes Angel was exhibiting since we had started dating. They had noticed her attire had become much more suggestive, and her make up more severe. There were other changes too. She was now sporting a tattoo on her right shoulder, an angel/mermaid holding a heart with my name on it. Sh...

Black Sissy For White Queen

by Samuelx on Sep 16, 2017
Interracial Love

I feel so damn great as I slide my strap-on dildo deep inside Ramon Jones. The six-foot-tall, skinny Black guy looks absolutely gorgeous in a bright pink dress, white pantyhose and high-heeled red shoes. His face is perfectly made up, rouged and his makeup and lipstick are applied nicely. The fuzzy black wig he's wearing only adds to his decidedly not so mas...

Mistress's Party Entertainment

by sissyapril on Sep 15, 2017
Transsexuals & Crossdressers

My Mistress was entertaining her sister Lady Brandi and her friend Lady Alexis in the living room and watching a Mistress dominate and humiliate a couple of her sissy slut males on DVD. The ladies were drinking wine as I was attending to the dishes after serving them dinner. I was wearing a French maid's uniform with black patent leather pumps and fishnet st...

Sissy Slut Boy

by SissyBoiToi1 on Jan 2, 2017
Fetish

You wake up in your bed, in your attic bedroom. You sigh, not wanting to get out of bed. But then, you realize 2 things--one, your alarm clock didn't go off, you overslept! You have 5 minutes to get to the bus! And two--your bed is soaked in warm, smelly liquid. Did you wet yourself? (Just a note: The "catch the bus" route leads to diaper-related c...

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Girl's Night Pt. 04

by DifferentBreed on Sep 14, 2017
Fetish

"You want to cum too, don't you bitch?" Sophie said. "But pleasure is only reserved for Mistresses and Dommes. Not sissy whores like you." Sophie looked down at him, grinning evilly, turned on by the lips descending her body and the sight of him kneeling there in sexual servitude and agony. She let her hand fall lightly on the back of Jenny's head as she fel...