Butt Plug Training Stories

119,106 results
Orientation
Length
Source
Infinite Scroll

From Stephen to Stephanie Pt. 05

by nikkiwest101 on Sep 12, 2017
Transsexuals & Crossdressers

Chapter one The preparations for my wedding proceeded apace, I was never allowed to see my wedding dress and was kept hooded during all of the fittings for it, these fittings were numerous and each time the skirt was made tighter, I wondered how on earth I would be able to walk in it. My training in every area increased, my voice coach visiting daily, my co...

Breaking Drake Ch. 10

by TheDragoness on Sep 15, 2017
Novels and Novellas

*** Author's note. This intro to this chapter is mostly story building. This is so that the powers Raell and future character have makes sense. I am limiting the background information, but if you want more information, message me. Thanks!*** Drake stayed curled up, sobbing softly, for a few more minutes. He was filled with self-pity, wishing to have his...

jenny Trains Her 'Slut-sis'

by slutty_jannelle on Sep 14, 2017
Transsexuals & Crossdressers

Although each story will stand on its own, the reader will enjoy the series more in sequence: "jenny's Education," followed by "jenny Gets a 'Sister." It seemed like she'd just gone to sleep when jenny shook Kay awake. "Time to get up, girl, We've got a big day ahead. Lots to do," jenny said, unceremoniously pulling the blanket off. Instinctively, Kay...

Hailey's Journey Ch. 07

by nanmar on Sep 14, 2017
BDSM

The rest of Hailey's week was similar to her second day, except for changes in costume. She wore a Playboy Bunny outfit, or leather corsets or short little cheerleader outfits, and carried out her dusting and serving duties. As long as she obeyed him, she got her reward in the night, when he would give her a nice warm, scented bath, massage her tired body, a...

Sara and Charley's Journey Ch. 03

by Steve1613 on Sep 12, 2017
BDSM

It was a week before they had a chance to play again. The intervening days had been long for both of them. She had had to get a proposal out and had worked 12 hour days all week long. He had been tied up in the evenings working on fixing up a home office for both of them. But now it was Saturday. They had both slept very well and woken up late. Actually, he...

The Slave Traders Pt. 02

by jamtby on Jan 16, 2019
Transgender & Crossdressers

Once reaching a small building outside the palace, my transformation started. The first thing was a hormone shot to start the change. Secondly, I was given women's clothes and told to wear them always unless ordered otherwise. Finally, I was ordered to sit when I peed. Further instructions and laser hair removal would soon start. I was given a western woman'...

Domina Katarina Goes Shopping

by pbs444 on Sep 17, 2017
BDSM

Several days ago, there was an e-mail in my inbox. It was of course from my Domina, Katarina, because the e-mail account is for her exclusive use, when she wishes to communicate with me. Because I am her sissy slut, and from time to time she finds ways for me to prove my usefulness to her. The e-mail read: "Hello, sissy slut, I have decided I wish to go...

Living With My Plug: First Week

by margaret_jenkins on Sep 19, 2017
Fetish

I slept long and sound that night, exhausted from the physical and emotional effort of the day. In the morning Lauren came to my room and got me up. She commanded me to show her that I was still wearing my panties in bed, and then remove them so she could inspect them. I was relieved to see the plug had prevented and escape from my bowels – the rear was pris...

Birthday Present Pt. 05

by donnaallure on Sep 18, 2017
Transsexuals & Crossdressers

Her Side I leaned back from the computer after reducing the cam image to fit in the lower corner of the screen. I was so happy with the way that Victoria had come back to life in her office. I could tell that Vic was really hooked on the feelings that women's clothing gave to him. I was still amazed at the turn everything had taken from the moment I had dec...

Welcome to Rolennia Ch. 02

by DrSqueaky on Sep 19, 2017
Erotic Couplings

I watched as Simma expertly wheeled the mouse around the spreadsheet, my hand resting lightly upon her shoulder next to a cascade of red hair. I had been working for three months now at the headquarters of Systems International in Yevczich, the capital of the small eastern European republic of Rolennia. Simma was my secretary—in fact she was the main reason...