Castrated Sissy Maid Stories

20,513 results
Orientation
Length
Source
Infinite Scroll

Jim and the Virgin Maid of Honor A

by barnabus on Sep 12, 2017
First Time

(M/F, reluctance, consensual sex, romance, first time, virgin, m/f) SUBJECT: The best man and the maid of honor connect the night before the wedding. WARNING: This is an adult story, containing graphic depictions of sensitive material of a sexual nature. If you find such material offensive or are underage, do not read further, but please bypass this s...

Humiliation with a Tail Plug

by myoddnewlife on Sep 18, 2017
Exhibitionist & Voyeur

Hello everyone, in case you didn't read either of my last entries here's a little back story on me. I am a very shy 27 year old woman; I am 5'2" and 105 lbs. My bra size is 34C, and I have shoulder length reddish brown hair. Up until about 4 months ago I have had a very normal sex life, no one had even seen me naked until I was married (yup virgin bride). In...

Unlocking Tally Ch. 01

by NerdyNymph on Sep 12, 2017
Toys & Masturbation

"Tally, you okay out here?" It was an understandable question for Claire to ask. She and the rest of my friends were inside the hotel room, talking and laughing up a storm, while I was standing outside on the balcony. It's not even like I had a decent excuse for doing so. The barren landscape of my tiny desert town didn't make for much of a few. Besides, I...

Back to the South Ch. 02

by eeric on Sep 25, 2017
Interracial Love

An hour later, Deena woke up sweating from the 80° degree heat. So hot... Deena got up, her sweat had soaked her nightgown, and her naked body was now clearly visible through it. She walked over and opened the window, and as the humid air gently breezed onto her face, she heard some moans coming from the side of the house. Down by the side of the porch, b...

Kate Haunted Manor House Ch. 01

by ZachDocEight on May 7, 2019
Erotic Couplings

Kate closes the term with a new submissive recruit Author's note: I have been writing adult stories for about 10 years so have a big backlog to share. But the recent Gothic story challenge brought out this story from me that had to be written. Readers should enjoy each of the four parts. I will publish subsequent sections about every fortnight. Constructiv...

La Contessa Ch. 25

by SlaveNano on Dec 18, 2018
BDSM

Chapter 25: The Carnevale Ball All is prepared. The guests have finished their banquet and file into the ballroom to wait in excited anticipation for their host's appearance. We follow them to take up our allotted positions, still dressed in the silk cloaks and peacock, phoenix, and swan masks. I'm excited. I've heard much about the palazzo's ballroom, and...

The Rose Diaries Ch. 21

by RoseB on Jul 16, 2019
Transgender & Crossdressers

Disclaimer and Notes: The Rose Diaries is an incredibly dark story focusing on forced (heavy emphasis on "forced") feminization of a completely non-compliant individual. There are elements of non-consent, violence, and dark subject matters. In addition, this story depicts dysphoria, dissociation, and general depression. I hope you do enjoy this chapter if...

You're Nobody ... Ch. 08

by Grouchojim on Sep 14, 2017
Erotic Couplings

Chapter 8 It took a week, but Sylvia came up with the money. Don't ask me how, but several of the photos turned up on the prosecutor's desk and Compton's lawyer's talked him into copping a plea that would see him serve ten years before any parole would come his way. When Klugman saw Johnny sneaking Haley into his room one evening, he was ecstatic, and rus...

Chloe's Sex Lessons Ch. 16

by Bodington on Sep 15, 2017
Novels and Novellas

When William Scott Hamilton was one week old, Randy reached a decision about where his life was going. It dawned on him that it was truly illogical for him to deliberately impregnate Chloe without marrying her. It was especially illogical considering that he could not think of any downsides to marrying her while there was a plethora of upsides. He came to re...

Aprons For Gayle Ch. 08

by Addicted2Writing on Sep 26, 2017
BDSM

AUTHOR'S NOTE: I wanted to thank y'all for your votes and comments. It tweaks my heart that so many of you are enjoying this as much as I am writing it with Scooter. SCOOTERS' NOTE : Thank you, shysub, for your concern as to my well being. It is much appreciated. Unfortunately, care in the community deemed me unsuitable and the local pharmacy is out of vali...