Babysitting Stories

2,018 results
Orientation
Length
Source
Infinite Scroll

I'm in love with the babysitter

by domingo on Apr 12, 2020
Amateur

Your wife is out of town for a business trip for a few days and you had a last minute work event this evening you couldn't get out of. Luckily your babysitter was also available for this evening as well at such short notice. Everything went smoothly this evening and feeling good about your work you are able to head home around 9 pm. This is almost two hours...

Open in Reader

Babysitter

by diaperslut on Sep 1, 2017
Fetish

Amber was nervous. She is a 26-year-old professor at a local college and at 5'8, B-cup chest on a very athletic body, she had caught many of the students checking out her chest and ass a few times. But she also has a bit of an odd fetish. Or, she thinks she does. That night would be the night she would find out after building up so much courage. You see, aft...

Open in Reader

Beckie's Purity Ring

by MommyMaker on Apr 23, 2019
First Time

My neighbors' daughter is pregnant mostly because of me. Beckie lost her virginity and conceived her first child while babysitting for me. I am a single mom with a toddler whose father is not part of our lives. I decided to move back to my home town a few months before Beckie graduated from high school. When I moved into our new neighborhood, Beckie came...

My Babysitting Business

by PinkIris on Sep 12, 2017
Erotic Couplings

It all started when I lost my job. I was working as a waitress at a restaurant downtown and I kind of enjoyed it. I started working there when I was sixteen and the uniforms were these skimpy little things of short shorts and tight low cut t-shirts. Because of my age, the owner had to make sure I only worked the early hours right after school, as the later c...

Dustin's Wife Ch. 03

by alparker on Sep 11, 2017
Loving Wives

This series is an adult based writing. It is intended for adults 18+. It contains graphic sexual scenes and lots of dirty words. If you need to go to the dictionary to know what any of the words mean, then you are too young to read this. Chapter 3: Vicki's Story As I sit here writing this I am waiting for two men I hardly know to take me shopping for a fak...

An Evening With Ashley

by Underboss3 on Mar 13, 2003
Erotic Couplings

I went downstairs to see Ashley. She was my 'sitter' for the weekend. The notion that I needed a babysitter was ridiculous, since I had just turned 18 two months ago. I didn't think my parents hired Ashley to babysit for me. They probably did it to make sure that I stayed out of trouble while they were gone for the weekend. Whatever the reason, I sure as hel...

Open in Reader

Femdom Space station

by andresterrada on Sep 21, 2009
BDSM

Captain John Logan started his career in Star Force as an eager 16 year old cadet. As he watched the Epsilon Space Station loom closer on the viewscreen of his shuttle, he thought back to that first day in the Academy and how he had dreamed of commanding a battlecruiser some day. The war with the Prajuk had ended and John had never seen real action. But he h...

Open in Reader

The Babysitter Ch. 02

by snaillover69 on Sep 11, 2017
Chain Stories

This story picks up where the last story ended, please read the first chapter, so that you can understand what has happened so far, Thank You. ***** Becky had just experienced the most powerful orgasm of her young life. She still couldn't believe it, she had actually taken the entire length of the 12 inch dildo. It had made her feel so full, so totally...

Trouble with the Boy

by al_Ussa on Sep 15, 2017
Humor & Satire

"Are you sure you got all of this down Becky," the nicely dressed, middle aged brunette asked. "Of course Ms. Harris," the eighteen year old babysitter replied. "All right," Ms. Harris said, "Well little Jack is asleep down in the basement so he shouldn't give you any trouble. I just want someone here to make sure nothing happens, just in case." Becky nod...

Summer Vacation Ch. 10

by D.C. Roi on Sep 13, 2017
Novels and Novellas

Just as he got to the bathroom, Kim emerged, wearing the same nightshirt she had on the night she came to his room. She glanced down the hall, then she put her arms around him and gave him a kiss that curled his toes. "Good morning, cousin," she said after the kiss ended, grinning at this flushed face and heaving chest. "Ah...good morning, Kim," Tommy croak...