My Babysitter Stories

336,266 results
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Adventures in babysitting

by Ashley16 on Feb 18, 2017
Exhibitionist & Voyeur

Summer, an incredible time of year. Exams were over, the school year was coming to an end and all that was on anyone's mind was parties, gossip and sex. I was no exception. I'd lost my virginity last year at my friends house party, while half the party listened from outside the door. This earned me quite a reputation, first as a slut ready to fuck half the s...

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Babysitter Caught on Tape

by mary1000 on Sep 14, 2017
Erotic Couplings

I work from home, and had mislaid my keys for my desk so decided to check the houses security videos, to see if I had put them somewhere stupid. Sitting down to go through them my stomach did a flip when watching back last fridays tape of the kitchen, onto the screen came our babysitter, Jess, with a man I had never seen before. He looked a good few year...

Bangin' The Babysitter

by TheSandyRavage on Dec 14, 2020
Erotic Couplings

The temperature was humid, the air thick, and the sun bright, which only made Mike's mood worse. He was sweating and cursing under his breath. The babysitter had just canceled on him. He ran his hand through his beard, trying to figure out the right move here. His wife was visiting family and he was stuck with their 5-year-old, but he'd had plans to stop by...

The Reawakening of Dr. Clark Ch. 10

by The_Maestro_Braddock on Sep 13, 2017
Erotic Couplings

Dr. Clark answered the door in a pair of khaki linen shorts and a green t-shirt. His face conveyed a tired anxiety, the kind that grew out of a sleeplessness spent rehearsing what he was going to say. Mallory, on the other hand, was the picture of relaxed cheerfulness. Her blond hair cascaded over her shoulders, clean and well kempt in an unfussy manner. Sh...

Ryan Paevey: The MILF Lover

by NicoleChiTown82 on Sep 14, 2017
Celebrities & Fan Fiction

Prologue: On a hot day in Sunny California a young woman named Savannah Jade was arriving at LAX to start a new life with her 4 year old daughter. She was a beautiful woman with full luscious breasts that filled out any top or dress. Her body was the perfect blend of curves. Her breasts were a 38dd and she had a 25" waist with a 42" hip. It had been 4 ye...

The Babysitter Gets Caught

by Jay142 on Aug 8, 2018
Exhibitionist & Voyeur

Dan and Leslie had been married just over seven years when their marriage hit some bumps in the road. They both worked full time jobs, and now had two young boys. The pressure of work, marriage and children put a stress on their lives and had a similar effect on their sex lives. What was once a hot, romantic sex life with some spice of kinkiness had now turn...

I Am the Night

by Sean Renaud on Sep 13, 2017
First Time

"Don't think I don't know what you're doing here Harold." Jessica said standing in front of the mirror and putting the final touches on her make up. "You're not nearly as clever as you like to think you are." "Whatever do you mean my dear wife?" Harold called back from the bedroom. He was sitting on the edge of their bed furiously putting a few final detail...

The Babysitter Revisited

by nasty_dan on Sep 14, 2017
Mature

I didn't intend to write a sequel to The Babysitter but there were so many generous comments and emails requesting a little more to this story that I couldn't resist. I tried to incorporate all of the suggestions that you requested. So, for the good folks who appreciated The Babysitter...well, here's to you. I hope you enjoy! * Cathy Marlin crouched silent...

Blackmail Bitch

by SlutProblems on Mar 26, 2019
Group Sex

Tisha was always on time. She was good with the kids. She didn't bitch about the mess that I left sometimes and she even did a bit of straightening and cleaning to help me out. I called her over about twice a week to babysit and everything had been fine until the night that she decided to show her true colors. It was a daytime barbeque at the country club th...

She-Male Babysitter

by sirhugs on Sep 28, 2020
Transgender & Crossdressers

[Note to Readers: This is not a story with quick short sex scenes, so if that is your goal, it might not suit you. There are detailed sex scenes, or one long detailed sex scene, take your pick. The use of the infirmary apartment setting is an homage to John Irving's The World According to Garp, which otherwise shares nothing with this story. My thanks to Car...