Buttplug School Stories

106,026 results
Orientation
Length
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Infinite Scroll

New Roomie Pt. 01

by Baulpocuse on Jan 20, 2020
Toys & Masturbation

This intends to be a multi part story of how my girlfriend's friend (Rachel) turns out to be an anal slut and our numerous adventures together as she becomes our roomie for six weeks. This story contains anal play, assfucking and cheating. If you're under 18, please close this site and leave. Note: This is my first story ever written and English is not my f...

Casting - Wonder Woman - Tape 04

by Rmcbar on Aug 24, 2020
Celebrities & Fan Fiction

All characters are (of course) over 18. This is fantasy, fantasy is legal. I apologise for the long silence, I hope to return to more regular posting. I hope you'll like this new instalment. *** Tape #4 - Kaley Cuoco Birth: November 30, 1985 Height: 5'6" Weight: 126 lbs Breast size: 32C Qualification: Getting the job of casting director on Wonder Wo...

Watching Ch. 04

by Longe on Sep 26, 2017
BDSM

Bound as she was Lexi could barely move. Despite the challenge, she did her damnedest to move her hips back to meet my thrusts forward. I made certain to keep my thrusts nice and slow and steady, which only frustrated the glowing red beauty. When she tried to hop on her free leg to get my cock deeper into her pussy, I pulled my cock out until just the tip o...

Having Sex the Greek Way Ch. 02

by Fereniki_Alexandrou on Dec 24, 2019
Anal

The following story is based loosely on true events, but some details have been altered for the sake of this retelling. ***** I woke up in bed with my boyfriend Joseph lying next to me, still asleep. Sunlight was pouring in through the sheer curtains that covered his bedroom window. I looked at Joseph's alarm clock, which was sitting on a small table by th...

A Virgin Trans Girl's Mission

by thehuntsman-king on Aug 24, 2020
Transsexual

On many levels, Eleanor was very proud of herself. She had just graduated high school, with a strong GPA and class ranking, a partial scholarship to a good university and several extracurriculars. She'd done this while figuring out her gender identity, figuring out coming out and hormones and all the other often embarrassing and difficult details that came w...

Open in Reader

A Second Night

by Phased13 on Sep 2, 2017
Fetish

The key card slipped through the door reader and we heard the click of the lock disengaging. I turned the handle and we walked into the room, tossing our coats into the closet. I quickly take off my shirt and sit down on the bed to unlace my shoes as you take your shoes off beside me, setting the bag next to the bed. We both sit up, look into each others eye...

Glass in the Ass Ch. 02

by Pink Sugar on Sep 19, 2017
Toys & Masturbation

Lying on my bed, I watched my soft tits rise and fall abruptly as I breathed heavily... the visual remnants from my previous mind blowing anal orgasm. Amazingly, my clit was still swollen, unsatisfied and aching. Still, I was too stunned and content to move and my mind started to wander. Recently I was shopping at Macy's and stumbled across a huge sale in t...

Making Holly

by Sissyhalo on Sep 19, 2017
Transsexuals & Crossdressers

My name's Jamie and I moved back to my hometown. I had a lot of bad memories here and most of them stemmed from being bullied in high school and a lot of that came from Holt Thompson. A loud mouthed jock in school he was the center of the basketball team and really, really arrogant. I was a geek, a comic kid and dungeons and dragons kid and all that stuf...

Being Holly

by Sissyhalo on Sep 13, 2017
Transsexuals & Crossdressers

Okay like right off I want to make it clear it's Holly now and forever. Holt's fucking dead and I'm killing anything that's left. And that's a damned good thing. See Holt was an asshole, I...he...that person I was...I was raised by an asshole. My dad and he wasn't a nice guy. He was a jock, he was a mean jock raised by worse my grand dad. Holt was part...

Meeting With A Strapon Mistress

by tyler777 on Sep 13, 2017
Fetish

We meet in the bar of my hotel. You are elegantly dressed in skirt, blouse, stockings and high heels. I notice your cleavage and your breasts pressing against the blouse. We sit down at a table and order some drinks. After a minute you reach into your bag and give me something wrapped in plastic. You instruct me to go into the men's bathroom and insert the...