Tail Plug Maid Stories

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Orientation
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Infinite Scroll

JoJo Becomes A Maid Man

by polishjoe on Sep 12, 2017
Transsexuals & Crossdressers

To see JoJo in her maid outfit, please visit my profile and remember to vote so I know you love me. Remember this is just a fun story about JoJo adventures. I want to thank the unnamed e mailer for the story idea. It all began when Mistress Del said she and David were going on an extended vacation and would be gone for 2 months. Although I was sad at their...

The Erotic Resort Ch. 02

by johncitizen on Oct 13, 2017
Erotic Couplings

Time had been going by since Liz and I had booked or holiday to The Erotic Resort in the Maldives. Liz had finished work a couple of days ago while today was my last day as it was a Friday as we were leaving to go tomorrow. I was tying up so lose ends in the morning when Ben came into my office and suggested we go out for lunch and have some beers down at th...

Simon's Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

Simon’s Sluts

by Ellyce on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One – Wake Up Call The alarm went off and I groped for the "snooze" switch out of habit. Then I remembered that I had day maid duty today and sleepily rolled out of bed. Wandering into the bathroom, I pulled the shortie nightgown over my head and observed myself in the full-length mirror starting at my red-painted toenails. My gaze wandered up my sh...

Future Mother-in-Law is My Mistress Ch. 02

by gregorymike40 on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next day much the same as the day before, although maybe not as nervous. I sent Lindsey off to work and got showered. I went and got the panties out of my sock drawer. As I picked them up my penis started to get erect. I did my best to get them on dealing with my erection. I knew Nadine might think something was up if I didn't show up with a hard...

Burden and the Beast

by a real jrkoff on Sep 16, 2017
Fetish

The Purchase- Milton Winker was drenched in sweat. The droplets trickled slowly over his wide, hairy belly and tickled their way down to nestle in his coarse wiry pubic hair. A wide single leather strap bound his large balls and forced them down from the base of his penis. He was a young man- only 21, and he was built like a pig… fat and hairy. His whole bo...

Candi's Conversion Ch. 03

by CandiCumminz on Oct 3, 2018
Transsexuals & Crossdressers

Please read Parts 1 & 2 first. - Candi has had a long night and tomorrow she begins her sissy life properly. First thing? Shopping of course! - I hadn't slept well. I'd gone to bed horny and frustrated, and Lucy's screams of ecstasy in the other room weren't helping. Just as I'd got to sleep, a few hours after I'd crawled into bed, a loud phone notif...

My French Maid

by LewisCrane on Jun 10, 2019
BDSM

You come over to my apartment. wearing a long coat. You're there to clean. You're nervous. I'm sitting at my desk, going over some paperwork. I'm wearing a suit with no tie. I speak only Russian- no English. You know I am very rich, and that you must do anything I ask. I gesture for you to remove the coat. Underneath it, you're dressed in the outfit I dema...

New Life.

by mally01 on Apr 3, 2021
BDSM

((Ms Christine Hewson former owner of her own mansion,disgraced and blackmailed to either be publically humiliated or to serve as a maid in her former home. The company she was CEO is now under the control of Cheryl Murphy her former personal assistant. She had been submitted to many humiliations during her blackmail and it was all documented. Now she finds...

Open in Reader

The Harem Slave Ch. 12

by naughtybabygirl on Sep 19, 2017
Fetish

The maid appeared to lead the two girls upstairs. Donning their matching robes, the two ran off arm in arm, giggling like schoolgirls. Exhaling a stream of smoke, the Master watched them go. "Sexy little things, aren't they?" Eric took a drag off his cigarette. "Like nothing I've ever seen before in my life," he murmured. Then, exhaling: "You're a lucky man...