Sissy Maid Fiction Stories

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Pinky the Sissy Maid

by Pinkytoes66 on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: All my stories are pure fiction, unless otherwise noted. Any similar events that may have occurred are purely coincidental. ;) This is part 2 of my current series. Part 1 was "Pinky's First Shopping Assignment". I've yet to decide on a title of the series and am open for ideas. Thank you. *********************** A few days after I completed...

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...

Sissy Maid Son Pt. 03

by Robyn228 on Oct 21, 2019
Transgender & Crossdressers

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 stood there looking at the black stilettos, with so many questions on his mind. He wondered why his brother would ever own stilettos, much less why their mothe...

The Valentine Surprise

by rogkw99 on Sep 16, 2017
Transsexuals & Crossdressers

(This is not fiction or fantasy. It is a true accounting of what happened to me last Valentines Day. Even if you think it is fiction, I think you will enjoy it. I would enjoy it if it were about someone else and not me!) I can't help but think of Valentine's Day last year, a day that forever changed my life. In the weeks leading up to that day my wife Ama...

Sissy Maid Son Pt. 02

by Robyn228 on Jul 18, 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 wept on his mother's bed feeling violated and abused. The maid uniform still on...

She Forces Me into Cuckoldry

by hismasterdivine on Sep 25, 2017
Loving Wives

This is my first fiction and features many aspects of cuckolding and BDSM. Forced feminization, spanking, body worship etc play a part in this tale, where a deluded subby boyfriend's thoughts run riot. If the story is a success, I might write a follow up, particularly due to its frustrating climax! ***** Dominant girlfriend wants a black lover, deluded b...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

Sarah Worked at a Football Party

by SarahCD on Jan 7, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences, my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected som...

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...

Rise of the legondery sissy

by monkey17 on Sep 1, 2018
Fan Fiction

Jamie Sonozaki awoke to the sound of hs alarm clcok. Standing at a hight of 5'2" with an hower glass shaped figuer. His messy blond here in a poni tiale and doe green eyes set into a hart shpaed face, maid him look like quit the fukcalbe girl. ONly he was not a gilr. The lack of boobs and a pussy prothed this. thoe to be fere his dick was only 3 inchis...

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