My Babysitter Stories

336,266 results
Orientation
Length
Source
Infinite Scroll

Thrash Maxim vs. The Other Dr. Phil

by XicotencatlSmith on Sep 1, 2017
Humor & Satire

Thrash Maxim staggered out of the building, trying to clutch at his heart. His arms, perpetually kept six inches from his body by his bulky lateral muscles, hobbled by his chunky biceps and popeye forearms, couldn't bend quite enough to reach his chest, and so he flailed like a youthful author reaching for a metaphorical butterfly. "I'm having a gawdamn hea...

SMS: Single Mothers Servicing

by HotnHornyGuy on Jan 12, 2017
MILF

She arched her back and cried out as you thrust your cock into her pussy again and again. Your balls slapped off her thighs as you took the single mother from behind, admiring the fine peachy arse before you. You still could not believe how your life had changed to the point where you were now on a bed plowing your cock into a horny mother as part of a local...

Open in Reader

Who Knew?

by YouDidWhut on Nov 25, 2017
Romance

It was Sunday November 22th, 2015 and I had taken my nine-year-old son to Disneyland to celebrate my birthday. He had finally reached the age where got excited instead of whiny when we had to stand in line for a ride. I was really enjoying the day when my phone buzzed in my pocket and, half annoyed, I pulled it out. As the next few minutes went by waiting fo...

My Babysitter Ch. 02

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

There it was again. That hard, warm cock in my mouth. I loved it. I needed it. I knew it wouldn't last, though. I awoke from my dream with my hands on my dick as usual, but my mom was standing by my bed. I was so surprised to see her standing over the bed I almost forgot to conceal my erection. "Hey son we're home from our trip to Hawaii!" she beamed. "Oh...

The Babysitter Stripper

by youngda44 on Sep 11, 2017
Erotic Couplings

It took a long time to find a babysitter for my infant child, but when my wife called one day to say she had found the perfect girl, I was thrilled that we'd finally be able to go out once again. My wife was beautiful, she had nice D cup breasts and a delicious body, but our sex life had been sapped by the arrival of a baby. At 25 we were both overwhelmed by...

The Reawakening of Dr. Clark Ch. 01

by The_Maestro_Braddock on Sep 12, 2017
Erotic Couplings

Doctor Greg Clark lived a typical, if upper middle class, American existence. A dermatologist with his own practice, he had patients enough to make a pretty penny and flexibility enough to do it while maintaining a fair amount of control in terms of the amount and times he worked. In his off time, he enjoyed running, playing pickup basketball with friends he...

Tales of Unintended Nudity

by ewong on Feb 5, 2016
Exhibitionist & Voyeur

You are an attractive woman, who somehow through the course of the day, ends up naked. You can be at home, school, work, or any place that you feel would be the worst place for an attractive woman like yourself to be caught naked. You can be an average woman, who has a job or goes to school. You can be a wife and mother. You can even be a celebrity. It's up...

Open in Reader

The Babysitter Has A Dick

by mr.z on Feb 29, 2020
Transsexual

Ricky Sampson is your average 18 year old boy. He lives with his parents and baby brother in a house in Nevada where he goes to school and works part time at a water park, it's Nevada the town gets really hot all year round. Ricky looks like a typical computer science nerd, with his glasses, black hair and pasty white skin but he wants to be anything but a s...

Open in Reader

Babysitter Makes Me Lose Control Ch. 02

by babysitterstories on Sep 25, 2017
Mature

Should I have told Shelley that our perfect little babysitter gave me the cocksucking of my life? Should I have told her that I jacked off to glamour shots of our slutty babysitter on my laptop whenever I got the chance? Should I have shown her the dirty texts she sent me? Maybe. I don't know. My guilt was strong, but my anger at Shelley was stronger. I gues...

Trapped in Amber

by Ironiclaconic on Sep 19, 2017
Erotic Couplings

"How was Jason?" Dawn fished in her purse for her wallet. "He was an angel, of course!" Amber had flounced in from the living room as soon as we entered the house, carrying a depleted bag of Cheetohs and a Diet Coke, which she set on the counter. "We played games until eight and then I put him to bed. I had to read him Bedtime Bear three times. He uses the...