Boy "butt Plug" Chastity Literotica Stories

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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...

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....

Three Tests

by Switch90 on Sep 25, 2017
BDSM

Like all of my stories, this was originally an email to my wife. Hope you enjoy how I get out my sexual frustrations. ***** I'm on my knees, naked accept for my chastity device and a collar around my neck. You're wearing knee high boots, black panties, and a corset. It's Friday night and you told me that if I was good this weekend I'd get a chance to cum....

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...

Slave Immigrant Ch. 22

by OldGuy1026 on Sep 14, 2017
Sci-Fi & Fantasy

After receiving a cloned body I immigrated 127 Light Years from Earth to Free Skyes. Unfortunately I had to work and pay for that cloned body and I had very few skills a high tech society could use. So it was either I become an Unskilled Labourer or a Sex Slave. I guess Human Recourses had me figured out correctly. All those years in BDSM chat-rooms and webs...

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...

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...

Family Chastity Story Ch. 04

by antares34 on Aug 13, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. ***** My girlfriend Christina has been staying with me for the past sev...

Feminizing First Step Ch. 05

by antares34 on Mar 30, 2020
Transgender & Crossdressers

This is a work of fiction. The events described here are imaginary; the settings and characters are fictitious and are not intended to represent specific places or living persons. All characters are age 19+. Chapter 5 Today began like any other. I awoke in my bed with my wireless earbuds still in my ears. The sissy hypnosis audio track was gently playing...

Detective Slave Ch. 02

by slaveboy6 on Sep 17, 2017
BDSM

Lying on my side in the cage, i heard light footsteps on the wooden stairs. The wire door was opened, and I felt the leash being attached to the ring in my leather collar. "Out slave!" Mistress Black Canary commanded. While on my hands and knees, i was forced like a puppy dog to follow Her. The dark-skinned lady led me to where i'd shot my load onto the ti...