Babysitter Stockings Stories

43,783 results
Orientation
Length
Source
Infinite Scroll

Babysitter Rin

by Sean Renaud on Sep 12, 2017
First Time

"Hurry up Honey; we don't want to be late for the play." Kevin was standing in the doorway adjusting his tie and making a few last minute adjustments to his tuxedo. It had been a few years since the last time he'd been able to take in a musical and everybody who'd seen Wicked had simply raved about it. "Coming!" Susan appeared at the top of the stairs in h...

Innocence Lost

by Reardon1 on Sep 12, 2017
First Time

Author's Note: If you're looking for a quick fix, this might fit the bill. I've been thinking about doing a babysitter story for a while; this is my attempt. * * * * Nathan Holbrook finally pulled out of the parking lot to his real estate office after a long, productive day. He had thought he would be longer but the showings he had scheduled went quicker...

Watching the Babysitter

by Boxlicker101 on Sep 12, 2017
Exhibitionist & Voyeur

Michael and Louise Herrick are doting parents of their six year old son, Justin, especially since he is an only child and expected to remain that way. Because of a low sperm count of Michael, Louise was impregnated in vitro, and it was such an expensive procedure they won't be able to afford to undergo it again. At one time they seldom left home at night and...

Babysitter Makes Me Lose Control

by babysitterstories on Sep 25, 2017
Mature

The kids were screaming, and my wife was out back, smoking another cigarette. Sometimes I can't wait to get out of the house, even if it means spending more time with Shelley, who's been growing meaner and colder as we age. It was going to be about ten more minutes until our new babysitter came by. The last one went to college last week—we'd used her ever...

The Babysitter Threesome

by NewWriter1 on Sep 3, 2017
Fetish

We arrived home earlier than expected, and Jessica, who had just turned 18 last month, had already put our daughter to bed. We had already informed Jessica that this particular babysitting job would be an overnight one and we intended to keep that promise. In addition, we made plans while on our date for other things to occur as well. I told Jessica to stri...

The Burlesque Dancer

by VelvetPeaches on Sep 12, 2017
Group Sex

It was Valentines Day and my husband, James, had told me to arrange a babysitter for the evening as he had booked ticket to a show as a surprise. I was very excited at the thought of a romantic night out, just the two of us. We didn't get to spend as much time alone as we would both like as he worked long hours and I stayed at home to care for our three youn...

Staying with Mrs. Wentworth, Day 01

by softspokenstephen on Sep 25, 2017
Mature

This is my first story and it develops a little slowly. Some people don't like that but I like a slow development. I hope you do to. It is obviously meant to be continued so if you have suggestions about things, I'd be happy to hear them and maybe make changes to make the story or characters better. I hope you enjoy this situation. *********** I'm 18 year...

Doin' the Boss: Babysitting

by RobynG on Sep 15, 2017
Mature

This is the third installment of my on and off affair with my now former boss. We worked together for two years before I ended my affair with the man 12 years my elder, only to rekindle our relationship over the Christmas holiday. For those of you who have written nice feedback, THANKS! For those who insist that I am a loose morals slut, you are entitled to...

Mr. Jackson Marks Marie

by SexySpanker on Sep 18, 2017
BDSM

Marie was frustrated. Once again her boyfriend Shawn had failed to satisfy her. After some gentle foreplay followed by a few minutes of slow, passionless penetration, he'd collapsed beside her, then snuggled up close and fallen promptly asleep. Marie, of course, was just getting started. She silently teased her clit as her boyfriend snoozed next to her, br...

Tabby After the Ball is Over

by Tabby18lover on Sep 11, 2017
Erotic Couplings

The ball had been like a dream come true. Tabby had never been invited to such a lavish occasion. It was a night of fine wine, dancing and beautiful women in beautiful clothes. She hadn’t disappointed Cliff that night. Her long flowing evening gown in powder blue looked stunning on the longhaired brunette. The little thin shoulder straps that held the slight...