Butt Plug Chastity Stories

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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...

Gimp and Pup

by felixkatz on May 22, 2019
Fetish

It was a fairly normal encounter during fetish weekend: Two masters sitting at the bar and chatting, their subs on leashes behind them. In this case, one of them had a rubber gimp on his leash, hands chained behind its back, a gas mask with darkened lenses obscuring its features. The other one had a rubber puppy sitting at his feet, hands locked in rubber pa...

Feminizing First Step Ch. 04

by antares34 on Dec 10, 2019
Transgender & Crossdressers

(All characters are age 18+) It has been months since my mom and therapist started my sissy transformation. So many changes have happened! Shortly after placing me in a chastity device, they revealed to me that the "male hormones" I thought I had been taking were in fact just the opposite -progestogen and testosterone blockers to be specific. To be honest...

Danni Ch. 03

by Coder3445 on Apr 21, 2020
Transgender & Crossdressers

Authors note I know it's been a few months since the last Danni came out and I am sorry for making those who want to read wait for so long. With that being said the reason for it is that I meant to write it but suffered from writers block at the time and eventually forgot about it. However I hope this does Justice as I tried to make it longer without sacrifi...

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...

How Chastity Changed My Life

by ronron1818 on Apr 22, 2020
Fetish

My name is Mary and I am 45 years old. I am ok looking, nothing that spells out sexuality in any obvious way. My life changed dramatically last year when my husband Mike started to work as an accountant for an all female sex toy company; that is owned and managed by Lisa who is a very sexual and sexy young lady. Lisa is 26 years old; tall and thin. She ha...

No Limits

by unfettered on Sep 17, 2017
BDSM

My master wakes me with a fist in my hair and drags my mouth to his crotch. It's still dark outside. I know my role here; I pull his soft cock into my mouth and begin to suck. He quickly comes to attention in my mouth and I keep sucking, drawing out master's first load of the day. I swallow, savoring the taste. His cum is like honey on my tongue. It sustains...

The Office Boy Ch. 06

by Aussie Worm on Sep 25, 2017
BDSM

Jenny stood naked in the centre of the dungeon, her wrists restrained to the ceiling forcing her to stretch and place all her weight on her toes. Her plastic chastity belt and bra that she had worn for past month had been removed and it wouldn't be needed again. Jenny's eyes were also taped shut and a blind fold placed over that so she couldn't see a thing....

The Set Up Pt. 02

by undermythumb10 on Sep 15, 2017
Fetish

This is the continued story of my life as a sissy and is a continuation from part 1 The Set Up. ***** As I mentioned I am sat tied to a chair with my stepdaughters panties placed so the crutch is over my nose, it's a long story which started when I met and married my wife now Mistress some six months ago. I am now a total submissive sissy cum slut for my...