Babysitting Stories

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How I Got My First BBC

by gracesnowpaw on Sep 26, 2017
Interracial Love

Babysitting and getting my first black man I met my first boyfriend in high school and we had been dating for about a year and a half. His name was Matt. He was the quiet loner type and he had a mysterious quality about him I was drawn to. We met shortly after I transferred to the school in grade 12. Neither of us went to college after we graduated with the...

Babysitting the Baumgartners Ch. 01

by Selena_Kitt on Sep 19, 2017
Exhibitionist & Voyeur

I was fifteen when I started babysitting for the Baumgartners. They had two kids. Henry and Janie were four and five that first time I sat in their living room eating pizza with them and watching "Lilo and Stitch" until they both conked out on the floor, their greasy faces smearing their mom's white carpet. I loved babysitting for them—Mr. Baumgartner ("Ca...

Susan Ch. 01: Babysitting (For 2?)

by SusieQuest on Oct 8, 2019
First Time

This happened just a few months ago, in late April. I reconstructed the dialog as best I could... I was babysitting for the Bentons, as I did every Saturday night. Except when I was babysitting for the Greens or the Hernandezes, though the Hernandezes were mostly Friday nights. Yeah, I did a lot of babysitting my freshman year of college. It played hell wi...

The Consequences of a Winter Storm

by Donna_Lynn_Cooper on Sep 25, 2017
Transsexuals & Crossdressers

Although I was actually the 19 year old babysitter in my second semester at the local community college, at this moment I looked very much like Carole Douglas, the wife of Jack and the mother of their three children. I was dressed in one of Carole's sexy red negligees; a cap sleeved long skirted mix of luxurious satin and lace; and was seductively kneeling o...

The Babysitter & The Waterbed

by RetroFan on Sep 13, 2017
Erotic Couplings

INTRODUCTION & DISCLAIMER - Let's travel back to 1992, where 18-year-old high school senior Sabrina, a responsible babysitter for a yuppie couple, receives an unexpected visit from her boyfriend Scott, and things get very interesting. As with all my stories, this is set in the past, and will no doubt bring back memories for readers who graduated high school...

Babysitting

by JadeMystery on Sep 13, 2017
Mature

I was nineteen years old. Definitely legal and by no means a virgin, but that didn't make what happened between Mr. Royce and me any less erotic. After all, he was a much older man, literally old enough to be my Father. He was my dad's best friend ever since high school and I was babysitting, more as a favour than anything. His second wife was much younger t...

A Soldier's Tale Ch. 03

by patrick2536 on Sep 17, 2017
Non-Erotic

It was approaching five o'clock at night on Friday 17th May. There was the normal crowd of drivers hanging around the duty clerk, pushing and shoving and I was just another one, hoping that I wouldn't be called upon for a last minute weekend duty. We were stationed just outside Londonderry, we were just over halfway through a two-year tour of duty and we wer...

Anabelle's Naughty Night

by LavenderBlush on Sep 14, 2017
Exhibitionist & Voyeur

Anabelle was really good at babysitting kids. It was easy to play and have fun with Bria and Jonathan, they were at the age that they still liked to run around outside going crazy on the trampoline or in the swimming pool. Anabelle usually let them run wild for a good couple of hours and soon they would be passed out from exhaustion by the time 8 o'clock wou...

The Babysitter Kaitlin & I

by timetravhippie on Jul 29, 2019
Erotic Couplings

Author's note: all person's depicted in this story who are engaged in sexual activity are fictional and over the age of 18 years old. _______ My wife and I had a three year-old son, Toby, and on those occasions when we needed to go out, we would usually call on the daughter of my next door neighbor, Frank. Her name was Kaitlin and she was a typically cute...

Jessica's Dream Ch. 05

by sexy_roland on Sep 17, 2017
First Time

Chapter 5: The Event is getting closer; fewer responses now A week and a half had passed now. There were only 3 more responses in those intervening days. Jessica decided that she would limit the number of fuck guys to 80 men, with a couple of men in reserved, just in case some could not appear on the weekend or developed cold feet at the last minute. She r...