Schoolgirl Spanking Stories

28,832 results
Orientation
Length
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Infinite Scroll

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...

Red Shoes

by lady_k2 on Sep 16, 2017
Fetish

My ass is on fire. I am being punished for buying shoes without permission. I know he loves spanking me, and the shoes were really an excuse, and I am glad to be able to give him pleasure in this way as much as in any other. But oh I wish he wouldn't do it so hard! He has been spanking me now for about five minutes, and I have already begun to cry. I quickly...

Spank Me

by Goldeniangel on Apr 3, 2019
Fetish

Authors' Note: This is a rough spanking story involving anal sex. Enjoy! ---------------------------- Hannah shivered as she walked down the hallway to the Headmaster's office. She was a horny little slut and she often got in trouble... ever since the very first day that she'd arrived at the all girl's school at the tender age of 18. That day she'd gotten...

Strapping Stress Relief!

by sarah thorne on Sep 17, 2017
BDSM

Amy is such a brat. Pure and simple. No actually, I take that back to an extent. (Sorry Sir). Why, you ask? Well, because, as was pounded into my poor, sore bottom with CB (Cracker Barrel Paddle), I am responsible for me. Never mind that she deliberately tells fibs and gets people in trouble. Never mind that she kept IM'ing me when she knew I had a paper...

Madison's Agreement Fulfilled

by madison018 on Sep 13, 2017
BDSM

This is technically the continuation of 'Madison Breaks a Window (part I)' and 'Madison, a black cop, and me. (part II)'. Madison's Agreement Fulfilled It was Monday night. The first night that Madison had agreed to come to my house for more punishment thanks to the cop whose name was still unknown. I had instructed her to ring the doorbell promptly at 7pm...

Spanking Night Ch. 01

by Angelscuck on Sep 14, 2017
BDSM

My wife and I had just booked the cruise of a lifetime! Los Angeles to Hawaii, then on to Samoa, Bora Bora, French Polynesia, Tahiti and back to Los Angeles. Twenty-eight days. No planes, hotels, or taxis. It took every cent we had but we have been dreaming of a cruise like this for years and now we were going! Although the transportation, stateroom with a...

Rebecca's Discipline

by kali.yuga on Mar 12, 2020
BDSM

The elevator doors opened to reveal an empty cab. Jared entered, holding a coffee in one hand while the other rested on the strap of his laptop bag. He selected 14 on the panel and returned to the center of the elevator. "Thank God," he sighed, both at the fact of his being alone and it being Friday. The cab doors closed and the elevator began pull...

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Sissy Slut Boy

by SissyBoiToi1 on Jan 2, 2017
Fetish

You wake up in your bed, in your attic bedroom. You sigh, not wanting to get out of bed. But then, you realize 2 things--one, your alarm clock didn't go off, you overslept! You have 5 minutes to get to the bus! And two--your bed is soaked in warm, smelly liquid. Did you wet yourself? (Just a note: The "catch the bus" route leads to diaper-related c...

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Sherry's Test Ch. 02

by PolyVoyeur on Sep 11, 2017
Fetish

Wednesday 3 PM came by and the group had assembled again in the meeting room. Sherry walked in hesitantly after finishing her classes. The two days following Monday's session had incredible highs and lows and Sherry was having a hard time coping with the emotional roller coasters they resulted in. The Monday session was followed by a romantic dinner which Sh...

Ananda Ch. 02: Returns with Roommate

by monkeykinglives on May 11, 2020
First Time

All persons depicted are over 18. A year after I had popped Ananda's cherry in the front seat of my small car after a street fest, she let me know via social media that she was going to visit her Nanny again. She said she hoped she could see my wife, Holly, and me for another fun night out. Ananda didn't know that the morning after she had fucked me in a s...