Sissy Maid Spank Stories

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Infinite Scroll

Becoming a Sissy Maid & Slut Vol. 13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twenty Two: Satin, Ruffles and Lace, Sissy Maids contracted out to Work. Monday morning and I arise as typical at 7:30am, enema, shower, shave do my makeup and put on a maids dress for the day. Today it's back into a black satin one. Master told me though to put on black back seem pantyhose for today which I dutifully do and make sure the seems are...

Sissy Maid Son Pt. 01

by Robyn228 on Jul 16, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18. ***** Peter walked into his house, feeling excitement clenching in his stomach. He's been pa...

The Slave and the Sissy Ch. 05

by Sputnik57 on Sep 12, 2017
Transsexuals & Crossdressers

Ayesha was not to be denied; slave was rampant after witnessing the erotic antics of the maids, and was anxious to please Ayesha quickly, so that he may watch over Pepper; she was so soft and vulnerable. Slave's cock rose quickly as he sniffed at the gloriously rich scent of the dusky beauty's thong. She smiled with a sense of admiration as he licked and lap...

To the Manor Bound Ch. 02

by Nikki258 on Sep 26, 2017
Transsexuals & Crossdressers

This is part two of a series; you'll probably need to read part one to get a grip on what's going on. As with the first part this focuses on forced feminisation including aspects of BDSM and non-con, so if that's not your thing, now would be the time to leave. Chapter 2 -- The Next Day Peter was barely able to find a second's worth of sleep that first nigh...

Becoming a Sissy Maid & Slut Vol. 08

by Sissy_Chantel on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Fourteen: Chantel Learns a Lesson. Another bright and early morning for me. Another busy day ahead as a sissy maid and later on as a slut. What plans Master has for me as a sissy slut tonight, I don't know, but I'm sure it will be exciting, with lots of creamy cum for me to taste and swallow as well as good for hard core butt fucking. I'm already ge...

Mistress Chronicles Ch. 03

by MistressMtoyou on Sep 25, 2017
Fetish

Title: Decision time Background/update Even if you've been following the last couple of stories about my subject, Muffin, you might want to read this background as there are a few new points of note. Muffin is slightly heavyset, 36 years old, about 5' 7" and 160 pounds. He is quite submissive and seems to be aroused by a number of fetishes, but he professe...

Sissy Prince: Origin Ch. 01

by SatinSlip on Feb 6, 2018
Fetish

Prince Oliver skipped through the castle garden. He loved the green and the flowers. He was nineteen and yet to be married. In truth his parents had coddled him as a boy. He knew his numbers and letters. He knew how to run a castle and a kingdom. On paper anyway. But he would never be a warlord. Never be a brave leader of men on the battlefield. His gold...

Recruiting of a Sissy Maid Ch. 05

by Sissy_Chantel on Oct 11, 2017
Transsexuals & Crossdressers

Chapter Five: Chantel Settling in with Her other Sissy Girls "Congratulations Chantel." as Maid Penny tells her today is her 3rd. month anniversary at The Jade Maid Club as they are sitting at the breakfast table with the other girls. Other girls also congratulate Chantel as well. Chantel replies, "Oh thank you all." As the girls eat their breakfast befo...

Young Master Ch. 03

by smittysimon on Sep 19, 2017
Transsexuals & Crossdressers

"That's a good little, sissy. I told you that you could take the whole thing." I feel a sense of ashamed accomplishment as her smooth balls rest on my chin and I smell her intoxicating mix of pomegranate and a hint of musk as my nose crushes into her flawless, taut torso. This was the last time. It had to be. We couldn't keep sneaking around waiting for a ch...

50 Shades Of Pale Pink Sissy Ch. 02

by davine on Sep 11, 2017
Transsexuals & Crossdressers

All characters are over 18. It's Thursday. Waking up I'm still miserable. I can't bother to look after myself. I'm dirty and bedraggled in old track pants a tee shirt. After I manage a coffee and toast I decide to check my computer. First I check my bank account and I'm astounded to find that there is twenty thousand more than I expected. I check my ema...