Tail Plug Maid Stories

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Orientation
Length
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Infinite Scroll

GTO - The Beginning Pt. 04

by GTO_Racer on Apr 3, 2018
BDSM

All characters are over 18 years old. This story is about how Gail became the seductress she is. I really encourage you to read my first story "GTO" to understand fully who Gail is as I spent much more time on her background there. This story takes place at the beginning of summer between her Junior and Senior year of high school. As you read this, please...

Sissy Dust Pt. 02

by Sissyhalo on Jun 4, 2018
Transsexuals & Crossdressers

*Before... "Spencer you don't have to pay me now I got off like four times, that's never happened to me." "I do, we had a deal and you missed fares and tips." He actually smiled at me. "Okay but under protest." I stepped up and kissed him my first kiss with anyone ever and Steven kissed me back and it became really passionate. We actually kiss walked to...

Sissifying Addictions

by Sissyhalo on Nov 25, 2017
Transsexuals & Crossdressers

They say you're born gay, they say you can't catch gay, that you can't be made into something you don't want to. That somewhere deep, deep down you really want it. It's somewhere in between and none of it either. It's actually so much like dominatingly slick, sinking, drowning...so very like that first time you sink into sweet sissy ass. It started for me...

Tommy's Further Adventures

by lsa3 on Sep 13, 2017
Fetish

A few weeks after the get-together with Margaret and Tommy, Scott called and asked Margaret if she wanted a sling. He explained further that it was a brand new one that a friend of his bought and couldn't install. Scott thought that the archway separating the bedroom from the closet/dressing area would be perfect for it. He offered to do the installation,...

Hotel Room

by nickitaylor on Sep 17, 2017
BDSM

I suppose the thing about temp work is that you never know what you're going to do next. Well, once - not too long ago - I got a strange job at a hotel. They were going to go for some kind of accreditation and find out how many stars they could put on their sign - you know the kind of thing. Well, to get their stars the rooms needed to be up to a certain sta...

My Initiation

by lockedupslut on Sep 13, 2017
Transsexuals & Crossdressers

(This story is a work of fiction. If you don't like erotic stories that contain cross dressing, heavy gay themes and water sports please just don't read it. Thank you.) * I was determined. This weekend it would happen. I would loose my gay virginity and complete manhood. The hard way. Tonight would change everything. Until now I've never had sex with a ma...

I Saw What She Did

by Scorpio44 on Sep 19, 2017
BDSM

[Sometimes a masochist meets the perfect sadist. This story is about how these two found each other. Your comments and votes are encouraged.] * She saw it coming. I was watching the people on the platform waiting for the train when I saw the man running. Twenty-five feet behind him a cop was running, trying to catch him. The man looked back at the cop and...

Curious WM 30 Ch. 05

by 0ra11yfix8ed on Sep 16, 2017
BDSM

Disclaimer: If you are offended by gay sex or curious old men or dominant women skip this story. Reading the earlier installments is necessary to make any sense of the story. If you can offer help improving my writing or this story please comment, any constructive criticism is appreciated! I sat in my car trembling with excitement. I wanted to stroke myself...

Fasten Your Seatbelts

by addictedtonylon on Sep 17, 2017
Loving Wives

Thanks to Lustyleader for her editing of the story, she was a great help. This account is fictional and the persons in the pictures did not participate in the events below. +++++++ "We're going to Antigua" my husband, John, told me a few weeks ago. It was time for vacation and some time away from the kids and his stressful job. My husband is a business exe...

Behind the tapestry Pt. 06

by johnpassion on Oct 7, 2019
BDSM

The king led her out of the room and to the bath. With gentle and loving hands he bathed her. The cool water refreshed her and soothed the many stripes that she wore. After drying her, he applied a soft scented oil that soothed her skin once it was applied. Their walk down to breakfast was silent. She had wrapped her arm within his and held her head on his...