Buttplug Punishment Stories

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A Virtual Change in Behavior Ch. 02

by AimeeDaze on Oct 9, 2017
Transsexuals & Crossdressers

When I came back around I could see light. It took my eyes times to focus, and when they did I realised I was looking up at Jeff's bedroom ceiling. I was still groggy as hell, like I hadn't slept in days, even although I knew I had. I tried to move again, but my arms were still bound. I could move my legs though and I stretched as best I could. I felt the si...

Crossdresser's Private Gloryhole

by kccrossdresserleslie on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story, I am a crossdresser and this is the story of a wild wild night! HI. My name is Leslie, I am a very dedicated crossdresser. I have to live as a male by day because of work. At night I usually get home pop open a beer and pop a buttplug in my juicy hole, get on the computer and watching some dirty naughty things until I just have to dres...

Celebrity Summer School Ch. 06

by DarkSwordsmanReturns on Apr 20, 2020
Celebrities & Fan Fiction

Friday, July 24th, 2020 Amy Adams opened the door to her Room 69K and stepped inside. The room was already half full, as it often was upon her arrival. Miss Adams had been teaching Anal 301 to her third year students since the start of the month, and it had taken the redheaded actress less than half a session to learn that her class of seniors were spilt i...

Gina Ch. 07

by Tommy1982 on Sep 16, 2017
Anal

I woke up with Gina's mouth on my cock. My dick had gone soft and slipped out of her ass during the night and, since she missed my cock, Gina had decided to suck it back to life again. "Good morning, lover," she said with her mouth full of my cock. "Good morning," I replied smilingly and grabbed her hair. I guided her movements on my cock with a firm grip...

Steve to Stevie to ?? Ch. 06a

by gbr2004 on Sep 13, 2017
Fetish

Ms Storm has videotaped me begging to suck her cock, and sucking it, and letting her cum in my mouth. I have been informed that if I don't do as told, everyone close to me will see a copy of the tape. I had been made to dress rather fem and go back to the gay lounge and hang around with some sissy fag boys. I even showed off for other men and let them watch...

A Story

by Master of Shadows on Sep 13, 2017
BDSM

I am sitting in my chair thinking of the punishment I have planned. I look at the clock. Five minutes till five pm. I told my sub to be here at five. I laugh as I look up and see her car pull up. I hear her knocking on the door at 4:57. I let her wait until five, before I tell her to come in. “May, lock the door before you enter this room!” I call out. I h...

Experiment 239 Ch. 07

by AmethystMelange on Dec 2, 2019
BDSM

"Tony, may I please suck your cock?" Anthony put his newspaper down, glancing up in bemusement. Sure enough, before him stood Sophie, unsteady and shaking in her unforgiving ballet boots. A faint sheen of perspiration beaded on her forehead, a most pleasing display of the toll the exertion was taking on her. Her green eyes were wide and pleading, and she ha...

Brett's Transformation to Brenda Ch. 02

by tinycuck84 on Sep 16, 2017
Transsexuals & Crossdressers

I opened my eyes slowly and yawn after a long sleep. I tried to move my feet to get up, but they are still tied to the bed posts. I tried moving my arms and I noticed they are tied to the headboard posts. My eyes widen as I feel my naked body underneath the bed sheets remembering the night before. I tried to wiggle loose, but there is no use as I am complete...

The Story of N Day 04-05

by shortonreality on Sep 14, 2017
Fetish

Background: this is a story about an advanced robot and AI, called N. This adventure takes place while my wife J is away on a long vacation. N is turning me into a cum slave. A few things that have already happened: 1) She has installed a nervous system interface that enables her to transmit sensations from various devices as though I were feeling them myse...

Husbands Panties Lead to a Surprise

by jennycnnn on Sep 13, 2017
Fetish

This weekend actually took place about 4 months before Steve's business trip to Las Vegas. It was suggested by someone on Literotica who likes to read about the panty play that my husband and have enjoyed together for almost the last year. This all started with a funny idea and a single pair of panties I bought Steve on a shopping trip together and it has tu...