Medical Punishment Stories

47,440 results
Orientation
Length
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Infinite Scroll

Live to Please...

by KiryusAna on Jan 21, 2020
BDSM

My waking up to a warm sunshine was a special occurrence in Master's room, as the curtains are usually closed, keeping the room dark until I were to open them to awake my Master, however, today was different... because I forgot to close them the night before, due to... well... activities spontaneously sprung on me by Master... I stretched out a little on t...

Transsexual Sex Slaves

by Otaku_Apologist on Jul 15, 2020
Transgender & Crossdressers

With a blank expression, she wept. The cock had a pulse. That pulse echoed from the hips to the shaft to the mushroom head and into her ass. She was a newborn dick girl, and she felt the soft, hard skin of her partner's cock dig into her cum-moist boypussy. Her tunnel was fully lubricated by sweat and foreign jizz. The erect arousal probing her stomach reach...

Miss Guided Pt. 05

by MissMarianne on May 6, 2019
Transgender & Crossdressers

We had a lovely dinner after which Donna walked us back to the new apartment. I decided to make us some coffee while Donna and Charlene had a conversation in the dining room. I could hear everything they were saying. "So, Charlene, Susan has told me that you have been a very bad girl. You were very naughty and need to be punished she said. I am very disa...

Undercover Mistress Pt. 02

by nexomorph on Dec 2, 2019
BDSM

The first part was a bit raw. Sorry, I rushed it a bit. Read it if you want the plot. In this part I cut to the main thing. The series will contain all kinds of BDSM stuff and fetishes Have fun! *** I was in front of woman of my dreams. Aurora. Mistress Aurora. In black corset, garter belts, stockings, black thong, glassy high heel platforms, oriental hair...

Redemption

by CharliMac on Oct 5, 2020
BDSM

Motherfucker. I sit and fume silently as the chaos of the school during lunchtime continues around me. I cannot believe that bastard got the better of me. As the two probationers in the department we should have been partners, working together to make it through our first year of teaching. But no, after the first couple of weeks when the head of the departme...

A Duet

by CharliMac on Sep 28, 2020
BDSM

I parked the car and glanced guiltily around me, but the street was empty. There was still a long line of terraced house right alongside me, with countless dark windows that could be hiding a watching face, but I wasn't going to disobey instructions. I'd learned that lesson. Shimmying my skirt up my hips, I tugged my panties down and off, then stuffed them i...

Pleased to Meet You Ch. 03

by Jackobin on Oct 6, 2020
Mature

[This chapter will make much more sense if you read chapters 1 & 2 first. This is only my second story here at Literotica. I have posted it in Mature, but it could also have been posted in Fetish, BDSM, or Romance. Obviously, it has a range of themes. Everyone in this story is well over 18.] The shy little widow from next door craves punishment and it is pr...

Ebb Tide Ch. 01

by FinalStand on Sep 19, 2017
Sci-Fi & Fantasy

Editing magic performed by KJ24 and Shyqash, plus contributions by the regular gang of brigands and neer-do-wells. Ebb tide: The period between high water and the succeeding low water. This tale is an espionage fantasy under assault by reality. The 'hero' of this tale might be considered a Libertarian, though the label means nothing to him. He is not comp...

Service Provider Ch. 14-23

by IdeeFixee on Sep 19, 2017
BDSM

Chapter Fourteen — Sunday School When she'd gone to Mass as a teenager on the old Headmaster's orders, Janice had been struck by the appearance of the Father leading the service. He was tall and rough looking, with large, craggy features and recessed but gleaming dark eyes. He had also noted the presence of the gorgeous, sensuous young brunette sitting in t...

Sins of the Father

by Averagejoe1992 on Jul 15, 2020
Novels and Novellas

Dear Readers, Firstly, this is a resubmission. This story was first posted under 'Romance,' as a celebration of exceeding 500 followers on Literotica. Despite the fact this story, at its core is about two people who fall in love (and have lots of sex), it was not well received. A rather vocal but small group of people made it their business to not read the...