Spanking Babysitter Stories

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Redwater

by UF on Sep 19, 2018
Amateur

Peter Grayson woke up late that morning his head ringing from his hangover. Slowly getting up out of bed, he made his way over to his bathroom washing his face in an attempt to wake himself up. Looking up in the mirror, Peter checked himself out. Peter Grayson was eighteen years old with short brown hair and brown eyes. He was tall with a muscular body and s...

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The Babysitter Ch. 04

by snaillover69 on Sep 11, 2017
First Time

Sue called Becky and told her to come over at 7:00, and tell your Dad that we need you to spend the night because we won't be home until very late. Becky explained to her Dad that she was heading over to the Summers house to babysit, and that they needed her to spend the night, they weren't going to get home until about 2:00 in the morning. Her Dad said a...

Why Women Don't Have Sex

by alias_words on Sep 12, 2017
Humor & Satire

After a long day at the office of men smacking my ass, talking to me as if I lacked intelligence and taking a pay cut so the CEO and his buddies could hit the bars after work, I was so looking forward to getting home to relax. My two inch heels were killing me, it was hot, which the nylons did not help any and traffic was horrible. Some idiot zipped past me,...

The Ethical Slutmaker Ch. 10

by KrisCherita on Sep 14, 2017
Anal

Chapter 10 A Perfect Bottom Dan read through the email a second time, glad that he had a private office and could hide the tent in his pants under his desk, and wishing Andrea had tagged the text NSFW. "Dear Tammi and Dan "Robyn enjoyed babysitting for you last week, and hopes you enjoyed your evening out. She's now decided that she likes and trusts you...

The Babysitter

by Lonedaddy on Sep 18, 2017
First Time

My wife and I live in the valley, just outside of the city. We thought it would be a nice place for a younger couple to raise a family. We bought a two story house with an attached garage. It needed a few minor cosmetic repairs, but nothing major. After some paint and building a new deck out back, it looked really nice. My wife Rose, is the manager of one...

Mr. Jackson Marks Marie

by SexySpanker on Sep 18, 2017
BDSM

Marie was frustrated. Once again her boyfriend Shawn had failed to satisfy her. After some gentle foreplay followed by a few minutes of slow, passionless penetration, he'd collapsed beside her, then snuggled up close and fallen promptly asleep. Marie, of course, was just getting started. She silently teased her clit as her boyfriend snoozed next to her, br...

Babying the Babysitter

by strictabdaddy on Sep 19, 2017
Fetish

It all began when I asked Shira: "Have you been a good little girl?" My wife had been dreading this moment for hours. Indeed, she had known about her impending mortification for days. Even so, she began to blush and cry at once. It was bad enough to be treated like a baby, but to be treated so in front of her best friend was particularly humiliating. Man...

My Babysitter Ch. 03

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

Getting forced down, a big, fat cock shoved down my throat. I was choking on it, I couldn't breathe. Oh, and another one, ramming my ass. It felt so powerful, and I felt powerless. These things never last though, and before I knew it, I was awake. I opened my eyes and there was the most beautiful woman to me, Annabelle. Well, that is if you consider her a wo...

Mom Sent Back to School Ch. 05

by StoryTeller07 on Sep 26, 2017
Fetish

Spanked in front of neighbours Rose looked at her eighteen-year-old daughter, Janice, and cringed. Janice was having great fun teasing her step-mother, while the woman had to endure playing the role of schoolgirl. Janice pretended to be the mother, and it was proving to be highly embarrassing for Rose. Embarrassing her step-mother wasn't the only reason J...

EDP

by LiteraryLover on May 13, 2019
Fetish

I woke up in a daze and found myself in my school's nurse's office. The last thing I remember was feeling dizzy in the middle of class and then it was just a blur. "Ah, you're finally up. That's good." The elderly nurse, Mrs. Johnson said with the bedside manner of a crocodile, or just an old lady tired of kids faking sick to get out of tests reall...

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