My Babysitter Stories

336,266 results
Orientation
Length
Source
Infinite Scroll

Stepdaughter vs. Babysitter

by Derek on Jun 7, 2005
Interracial

Rodney Cox is not happy to hear that he is going to have to stay late working at his shitty job tonight, especially since his wife is out of town on business and that means finding a babysitter for the kids. Of course his first thought is his stepdaughter Lindsay, but as was more and more common these days she is entirely unhelpful. "Hell no, Rod, I've...

Open in Reader

I Bring You Dinner

by cincy29 on Sep 17, 2017
Loving Wives

You call and tell me that you have to work late and not to hold dinner for you. After hanging up with you, I make a call to the babysitter and see if she is available. She is and says she will be here in an hour. Just enough time I think. I run a bubble bath and pour in baby oil to make my skin nice and smooth for you. I am excited because I have waited fo...

Furthering My Education

by jimmysub on Sep 15, 2017
Fetish

Well I had to go back to Community College to take some child development courses as my wife and her lover are planning on having a child together. This is part one of the adventure. I really don't like this idea but what my wife says go. Her biological clock is ticking and she has been with the same lover, Mr. Steve for about 3 years. So Debbie is going to...

Babysitter With Benefits

by AuthorIvyEast on Nov 18, 2019
Erotic Couplings

Tiffany rolled over in bed, brushed her curly, dark brown hair from her face, and looked at the clock. It was seven o'clock in the morning, but she had nowhere to go now that she had gotten laid off from her job. Despite her young age of only 23, she really enjoyed her marketing manager job. In this prestigious role, she spearheaded various clients and pro...

The Reawakening of Dr. Clark Ch. 03

by The_Maestro_Braddock on Sep 12, 2017
Erotic Couplings

"Alright, I dropped the kids off at your parents' house so that's all set," Gina told Greg as he walked through the door, kissing him on the cheek, "Sally should be here in like 30 minutes to pick me up for the casino. What time are you heading out?" With some amount of regularity, Gina and Greg would leave Martin and Shelly with his parents and go out with...

Up Late

by LorenzoAbajos on Sep 14, 2017
Erotic Couplings

I was up late, driving around the countryside. I would need to get home before daybreak. It'd been an interesting night, and it might get more interesting before it was over. We'd arrived home at around midnight. Our babysitter, Aubry, was waiting for us. She was an eighteen year-old Senior in high school. This was the first time she'd sat for us. With just...

College Shemale babysitter

by tomf15 on Sep 15, 2017
Transsexuals & Crossdressers

Disclaimer: All characters are 18 and over. Jessica pulled up in front of a large house at the end of the street. She looked down at the text; 1278 Backstreet. "This is the right place," she thought. Jessica was a fairly normal, attractive college girl. She studied hard, partied on weekends, and liked to work out. There was one thing that separated her f...

When I Came Home Early

by unowen1987 on Sep 12, 2017
Erotic Couplings

I was finally going home. It was about 10:00 at night, I had just gotten off work, early if I recall, and was heading back to my house for a night of easy sleep. A bit about myself though, I am 22 years old, and I work on call, 24/7. I am 6'6" and weigh in at about 200 lbs. I work out regularly and because of my on call status I get paid even when I don't h...

Melissa Ch. 01

by gummidurango60 on Sep 19, 2017
Transsexuals & Crossdressers

"Melissa," my mom called from the kitchen. "Yes," I answered from my bedroom. "I want to talk to you for a moment," "Okay," "What's wrong?" my mom said as I walked into the kitchen. "Even with my scholarship I'll never be able to afford the tuition to..." I began as I plopped on a stool at the island. I'm eighteen and a week out of high school; all I w...

The Reawakening of Dr. Clark Ch. 11

by The_Maestro_Braddock on Sep 12, 2017
Erotic Couplings

Dr. Greg Clark gritted his teeth and tried to focus on Ms. Bristol's words. It wasn't that she was boring; he was genuinely interested in how Shelly was adjusting to life as a kindergarten student. Mallory, however, was making it damn hard to concentrate on anything but how hard he was and how good her hand felt— slipped through his open fly and unbuttoned b...