Sissy Maid Stories

19,946 results
Orientation
Length
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Infinite Scroll

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...

Replaced Ch. 02

by chas19839 on May 23, 2018
Fetish

I wasn't anywhere close to having the house where I wanted it when I heard the crunch of tires on gravel in the driveway. Vince and my family had been gone for over three hours. They must have gone for a walk or maybe shopping after lunch. It was such a strange sight seeing the four of them walking from the car to the house. It felt surreal. I opened the do...

Sissy Auction

by davine on Sep 26, 2017
Transsexuals & Crossdressers

Authors note: this story is a fill in while I get over a block with the fifty shades part three. I also need to revise part two of sissy downfall as Literotica rightly pulled it due to excessive violence. I wish this story was autobiographical. It's not but has some elements of truth in it. I hope you enjoy reading it. I love feedback; even negative. All cha...

Miss A's New Play Thing Pt. 04

by Pornenthusiest on Mar 2, 2020
BDSM

Recap: Miss A had just finished a luxurious bubble bath and was returning to her slave who was chastised and gagged with her pantie hose and a ball gag, with Miss A's wetted panties draped over his nose. Locked away in her dungeon, after an arduous breath control play session, her slave was spread wide at the ankles with a spreader bar, bent at the waist wi...

Becoming a Sissy Maid & Slut Vol. 14

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Three: Sissies at Work, Sissies as Sluts at the Farm. 4:00am and the alarm clock goes off. We three sissies must wake and begin our day of long, hard labour of degrading sissy maid and sissy slut work. Off comes our sleeping lingerie and soon three naked with only our chastity devices dangling on our sissy dicks we must quickly and together s...

Developing Emma Ch. 03

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

As Kurt caressed Emma's sweetly pronounced bottom, she realised she had never felt so feminine before, despite her newly freed cock standing stiff in nervous anticipation. She looked at the powerful male and the leering male audience; the few females there would now witness her being used as a woman. Kurt's large stiff cock rubbed against her belly as he mov...

Melody the Maid

by nohbdy88 on Sep 14, 2017
Transsexuals & Crossdressers

Melvin had been out of work for six months now. After being let go from his previous job, he had promised his wife Susan he'd find new work soon, but soon fell into lazily living off of Susan's income. At her request, Melvin had started helping out with the housework even more. One day, a package arrived in the mail for Susan. "Honey, I have a gift for you...

Jerry becomes Jill Pt. 05: July 4th

by gasissynora on Apr 27, 2020
Transgender & Crossdressers

Jerry becomes Jill: Part 5: July 4th Week End This is the fifth part of my story about how I became Jill. After having started female hormones, Jill is introduced to group play by Mistress Rikki. The Fourth of July is on Monday and that Thursday evening at dinner Mistress gives me some information about the holiday weekend. She says, "Tomorrow you are done...

First Time Cuckold Ch. 05

by Angelscuck on Sep 14, 2017
Fetish

Oscar started sucking my well fucked pussy with great zeal, licking up all the cum that Jordi had deposited. Jordi's cock was so big and thick that it had left me quite sore and Oscar's attentions were both soothing and stimulating. After about an hour and four orgasms, I reached the conclusion that I really enjoyed being sucked to being fucked. Oscar looke...

Maid on Boxing Day

by Belongs2Beth on Sep 14, 2017
BDSM

Authors note: This story is an immediate sequel to my first story "Carol's Christmas". The events of this story deal with the younger man named Marcus who Mrs. Carson initiated into the mysteries of sex and submission in "Carol's Christmas". * Marcus was sweating bullets as he rang the door. He burned for Mrs. Carson...Mistress Carol...and needed to be wi...