Buttplug School Stories

106,026 results
Orientation
Length
Source
Infinite Scroll

My Gay Ex-Roommate Pt. 03

by 1077ad on Jun 19, 2018
Novels and Novellas

Over the next week, my brain kept exploding a little when I remembered what I had done at Alan's place. It was a huge distraction as the feelings, smells, and tastes flooded back in and pushed everything else out of my mind. I was surprised that while there was a sort of awkwardness about it, I didn't feel conflicted or ashamed or hung up that I'd had sexual...

Liquid Shower

by michaelhunt on Sep 14, 2017
Fetish

Collette and I hadn't participated in any scenes with Jeff & Rebecca or Lisa & Scott for a while. The kids had been a handful lately and our parents always seemed to be too busy to babysit them. We were having plenty of straight sex almost every night but there was no spontaneity to it. It was too mechanical, too planned. Collette surprised me one night rec...

The Party's Ripe for Caning Ch. 04

by lesliejones on Sep 19, 2017
Fetish

This story does involve bodily functions and humiliations so those offended by these topics should read no further. All characters are 18 or over. ***** Linda Crawford noticed that student behavior in her classes—both the majority, which were all boys, and the one all-girls class—seemed much improved of late with all pupils very careful to avoid being seen...

London

by motacilla on Sep 2, 2017
Fetish

I must remember to bring a schoolgirl outfit to London... Hmm.. I could wear it and we could take a walk through the city. Buy ice cream, maybe? Can you imagine that? Me and you walking... I would make sure to bend over at every opportunity to show u the color of my knickers. Hm... Maybe I'd wear a buttplug... And tell you as I eat the ice cream just how...

Kinky Secrets Ch. 24

by pvclook on Sep 26, 2017
Toys & Masturbation

When Mary woke she found the dildos had shrunk back to their normal size and the hands were loose. Pulling away from her Daddy Lover she easily slipped off the anal plug and dildos. The groping hands nipple shields also came away. Looking down her body her clit was still huge and it seemed to have grown due to the rough treatment. Thinking back she couldn'...

I Secretly Recorded My Boyfriend

by sdiwantit on Nov 20, 2018
Toys & Masturbation

As I set up the nanny cam in the back room my pussy tingled in anticipation to what I might catch my boyfriend doing on video. It was Wednesday and I had to go on a business trip until Saturday. I packed all my usual business attire and the essentials and at the last minute I tossed a small vibrator in my bag. Who knows if I'll even get any time to myself...

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...

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...

CD Asst. Secy. Ch. 01: End and Start

by cdtycoon on Apr 22, 2020
Transgender & Crossdressers

All the characters in the story are above 18 years of age. INTERNSHIP ENDS HERE On Monday; 9th December, as usual, I woke up at 5:00 a.m. as it had become my routine even though my alarm is still set for 5:30 a.m. anyway I got up and took a nice cold bath from head to toe and came out wearing towel at my chest. Then I went to get dressed in my white drive...

Punished Asian Shoplifter Ch. 02

by asianspankee on Sep 15, 2017
Fetish

"Good," you say, "let me give you some more details so that you know what to expect. The duration of your punishment will be a total of 10 weeks, starting now. After today's punishment, you will return here once a week for your next 9 lessons. They will be progressively more painful and humiliating for you." An uncontrollable shiver sweeps through my slim b...