Anal Plug Punishment Stories

80,193 results
Orientation
Length
Source
Infinite Scroll

Vera's Pet Ch. 01

by Terrin2 on Sep 13, 2017
BDSM

Brian was nervous. He was going to see her again after two years and he remembered that when they parted it was not in friendship. Well, this meeting was just business, but Brian couldn't help feeling a thrill. He didn't know how he was going to hold his ground in face of that woman. He had always been scared of Vera and his own fear had always excited him....

Mistress Has a Business Trip

by Bondage_Ben on Sep 14, 2017
BDSM

"I'm just really stressed," I told my wife over the phone as we talked at the end of the day. She was in a hotel for the week, working out of town, and I was back at home, working as usual. We had talked extensively about her work for the day, and she had asked how my life was. "Is that so?" she asked. "Yes it is, sweety," I said, a little bummed. "Well,...

Making Francesca Ch. 05

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

It seems that I finally have gotten the time to finish posting this story. If you have not read the first four chapters, I highly recommend it as the story will make much more sense. Enjoy. As he sat there on the thin mattress, pondering his new outlook on life, Justin appeared with his supper. Justin opened the door to the cell and placed a folding chai...

The Dentist Ch. 1

by swtncute2 on Sep 13, 2017
BDSM

This is a story straight from my imagination. Any correlation between the players in this story and actual people is purely coincidence. Enjoy J * * * * * The date is March 18th. Arianna looks to her calendar to see what appointments she has scheduled for the day. "Lets see here, Board meeting at 9am, what a way to start the day…ugh! Finance at 11am, tha...

The Assignment

by Miyelo Ina on Sep 12, 2017
BDSM

I put the car in park, turn the key to shut off the engine and take a deep breath to compose myself. The butterflies in my tummy refuse to go away though. Half of my mind is standing off to the side screaming, "What are you doing, girl? AH! Go home where it's safe!" But the other half is loving the anxiety I feel, craving more, craving to be in your presence...

Discovering Virtue

by MasterTiberius on Sep 14, 2017
BDSM

A story for ruby. In order to know virtue, we must first acquaint ourselves with vice. - Marquis de Sade Ruby gently slid on one of her black stay up stockings and smiled, reflecting on what she thought might transpire this evening. She was going to meet Tiberius for, what he had indicated, an evening of adventure. She had received her instructions in an e...

Teach Me a Lesson Ch. 01

by Anaribrady on Jan 20, 2020
BDSM

You set up the rules and I agreed to them, even signed my name to them to make sure we both understood that my agreement was 100% consensual. These rules were set up so that I can learn to control my bratty behavior, my impulsiveness, my rude behavior. I need, desperately need, to have boundaries and, more importantly, have those boundaries enforced. 1. I...

Slave Immigrant Ch. 05

by OldGuy1026 on Sep 15, 2017
Sci-Fi & Fantasy

As we last left off I finally got my citizenship authorization; and talk about bureaucracy, it too all of a minute for everything to be electronically processed. The company was holding all of the belonging patrons had purchased for me as gifts, and an identification ring slash debit card. I didn't have any credit, but an active bank account recognized on al...

A Touching Tale of Hardcore Anal

by lourdez01 on Sep 25, 2017
Anal

You're going to make me take a cab from the airport wearing a short, black skirt, black garters belts, ruffled panties, and pigtails. I'm going to walk into your house and find you on the couch, but you're going to tell me I can't touch you because we're going to play a game first. My short skirt is barely going to cover my beautiful, round ass, and my large...

Damn Panties

by renee00 on Sep 15, 2017
BDSM

I was sitting across a table booth from you while we're out at dinner, and you knew that I was wearing panties. You saw them while helping me in and out of your tall truck – my dress had slipped up and you got a quick glance of black lace between my smooth caramel thighs. The panties were sexy, but they were still hampering your access to me nonetheless. I k...