Maid Chastity Stories

20,460 results
Orientation
Length
Source
Infinite Scroll

Ultimate Sissy Weekend Ch. 06

by SissyTwinkleToes on Feb 4, 2020
Transgender & Crossdressers

Susie wonders if she'll ever get used to the horn honks. The gasps. The shouted comments. The whispers. The cruel laughter. She is stood with her sissy sister, Tinkerbell, in her pink OTT sissy dress she's been trapped in for over two days now, on the corner of the bad neighbourood where she now lives. It's 7:45, and she's been stood in public for almost two...

Tessa's Gambit

by Etaski on Feb 4, 2020
Humor & Satire

Co-Authored by Chimera46 and Etaski Lady Tessa Du'Witt lifted the dark shred of mourner's veil which was to pass for clothing. She compared it with the matching small pants which would bunch up in the valley of her backside. A shiver touched her, though she held her voice steady and brave. "And this shall somehow entice him beyond laying my body bare in hi...

The Hostess

by justincbenedict on Dec 25, 2019
BDSM

Carmine shook his head as he looked at the host of Prometheus Fishbein's birthday, Fish himself. What the hell? Angel had thrown Fish this uh, bash, but when Carmine had walked in, he'd seen Fish kneeling naked on the floor, wearing a pink ribbon around his dick. On Fish's chest hung a sign, suspended with twine that said "SMALL PENIS BIRTHDAY BOY". The...

Behind the tapestry Pt. 07

by johnpassion on Oct 7, 2019
BDSM

They emerged from their bed chamber about noon time and headed to the dining room. Lunch was being prepared and they released each others hand and went around the room greeting people. As they neared their chairs, the king stepped up and pulled the queens chair back, kissed her neck and said something softly in her ear. "I do." She replied softly and looked...

The Adventures of Ellesbeth Ch. 04

by Justliz69 on Jan 20, 2020
BDSM

Alicia walks into the parlor where I am waiting. She approaches me and gives me a nice tender hug and looks me in the eye. She then leans forward and kisses me on the lips. I inhale sharply as I feel her lips, the kiss is electrifying. It takes maybe a half a second before I start kissing her back. She pulls back smiling, knowing she has broken down that fir...

Alternatum

on Apr 22, 2014
Fetish

"Fancy long naps, yeah?" A sudden voice shatters the tranquil noiselessness of the atmosphere, pulling you away from your deep sleep and back into consciousness. Looking around, you see that you're in what appears to be an abandoned warehouse as various crates and boxes are scattered throughout the area. You're seated in the center of the building...

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From Friends to Lovers Ch. 20

by neruval442 on May 12, 2020
BDSM

The weekend rolled round again, and Beth glanced at me across the breakfast table. "Can we spend some time on planning the wedding today?" "Oh wow, Beth," Sarah breathed, "this is going to be amazing." She leaned to whisper in Beth's ear, and Beth nodded, glancing at me. "Definitely." "I promised to give you some venue suggestions, didn't I," remembered S...

Chloe's First Taste

by slowburn603 on Jun 9, 2020
Group Sex

The following story is true. The names have been changed to protect the devious. The Friday night party was a staple at our house that occurred nearly every week. It was a phenomenal way for my wife Chloe, I and our friends to blow off some steam from a tough work week. Most of our group are military, most in their early 20s so the parties were loud and hi...

The Assignment Ch. 08

by Satan_Chey on Jun 2, 2020
Novels and Novellas

Chapter 8: ---reality--- I killed her best friend that probably makes me an asshole, but Jackson is a fucking serial killer not a pussy who'd just let someone ruin his relationship. "Fuck it, "I mutter clicking save on the document before closing it and getting up from the desk where my laptop is sitting. I walk passed the unfamiliar bed and walk towards t...

Sharing

by Lady_Natalia on Jul 13, 2020
BDSM

"Come on sweetheart, put on the maid outfit I got you. You will look so hot in the thigh high stockings, corset, and tutu," my husband cooed. We have been married a long time and have been experimenting in the bedroom and out. I have found that I am a submissive and love when my husband, Jake, ties me down, gags me, etc. I'm not into humiliation or pain, e...