Tail Plug Maid Stories

54,794 results
Orientation
Length
Source
Infinite Scroll

Sissy Maids & Sex Slaves Ch. 01

by RickyRooster on Sep 13, 2017
Fetish

Reader Notes This is a fantasy story patched together from a series of e-mails I have sent to a very sexy lady. She loves bisexual men and she loves men who wear panties. She is dominant but in a very genteel way, if that is possible. It's told and written in a different style than I usually employ. I feel this style is rather staccato, telling her what w...

Ace Li's Adventures in Pornland 04

by assco on Sep 11, 2017
Sci-Fi & Fantasy

CHAPTER VII A MAD SEX PARTY AS ACE LI wandered through the wood she thought about Yakubutsu Katapira's vice and whether she oughtn't to follow it pretty soon. The sun shone through the trees and dried her arms and legs, though her hair was still wet from Redi Obasan's pussy juice and her blouse still clung to her little tits. (And if that means nothing to...

Maid Service Ch. 03

by grgy56 on Sep 12, 2017
Transsexuals & Crossdressers

I love that feeling of putting on fresh, crisp, lacy panties. They hug my bum so nicely giving me a beautiful curvaceous rear. Well as beautiful and curvaceous as a guy's bum could be. No matter how much I tried, I could not get that firm, round butt like Laura has. Anyway, I had just finished cleaning the house for Laura. I took a long shower and carefull...

My Sissy Life

by snorn on Nov 26, 2017
Transsexuals & Crossdressers

I love being a sissy. I have been in permanent chastity since 27 Sep 2016, and am loving it. I have sissy training rules that are focused on keeping me doing the household chores and training me to be rented out as a cheap sissy whore/maid, a list of sissy motivational sayings which I listen to on repeat whilst doing nightly chores, and service rules for th...

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...

Special Occasions

by Slovdave on Mar 26, 2019
BDSM

By: Slovdave. From original ideas by: Maria. Julia appraised herself carefully in the full-length mirror. She had reverted to her natural dark brunette hair. For these occasions, she liked a certain truthfulness. In her early thirties, slim and toned, she possessed a striking figure even without the current outfit. Her eyes were a light hazel, flecked wi...

Trixie's Chastity 01

by trixie47cd on Sep 19, 2017
Transsexuals & Crossdressers

Part 2: Trixie learns his new role. Since my wife came home early and caught me masturbating in women's frilly lace 2 month ago, so much has changed. She has taken control of my life since I begged her not to spread the story and pictures of my humiliation around town. After I made the choice of submitting to her feminization training, there really was no...

Girl's Night Pt. 03

by DifferentBreed on Sep 14, 2017
Fetish

Fisher climbed the stairs slowly, wary of the quiet that hung over the upstairs. As he hit the landing a soft moan emanated from the bedroom and his heart raced as he entered the doorway. There, framed in the soft light of the bedroom lamps, was Sophie kissing another woman. Her crisp white shirt was unbuttoned, exposing the top of her supple breasts, and gi...

At Her Disposal Ch. 01

by Sputnik57 on Sep 15, 2017
BDSM

He had remained a bachelor, blaming the rigours of his working life which had often seen him travel to the corners of the British empire on business as the reason for not taking a wife, in response to those who cared to ask. The real reason for Henry Trent remaining single at nearly 50 - he being a more than reasonably well off Victorian gentleman, fit and a...

March Madness Ch. 09a

by jbirdman on Sep 13, 2017
Transsexuals & Crossdressers

This story is not intended for children and if you are not old enough to read sexually explicit material, go away. This story features some elements of female domination (femdom), teasing & denial, chastity training, mild bondage, creampies, cuckolding cross-dressing and a few other fantasies of mine. I hope you find it entertaining, but if you might be offe...