Sissy Babysitter Stories

9,467 results
Orientation
Length
Source
Infinite Scroll

A Christmas Story

by lordgeek4 on Dec 25, 2019
Celebrities & Fan Fiction

John was not happy. It seemed like everyone in the whole world was having a good time. Everyone else, that is. Nothing was going right today. "I can't find my Girlfriend's Pussy. My Girlfriend can't come over and play. Now I have to stay here with a babysitter." It was a new babysitter, not even someone familiar. It was two days before Christmas, too! Th...

Babysitter Cupcake: MILF Cuckqueaned

by silkstockingslover on Feb 26, 2019
Fetish

Summary: College girl seduces wife and then fucks husband. Note 1: I have been asked by a number of people for a couple of years to write a cuckquean story (which made me look up what cuckquean means). I had begun attempts on one a couple of times over the past couple of years, but I set them aside when the plots didn't work. Then after a few more requests...

Barebacking the Babysitter

by IrishDude3881 on Sep 11, 2017
Mature

As a middle aged salesman and father of two, I rarely have time for dating. I usually get by on random hookups, but recently I experienced a drought. After a couple of rough months, I was dying for release. I arranged for the babysitter to watch my daughters and headed to the bars in a last ditch effort to get laid. Unfortunately, I suffered a night of strik...

Mandy's Sexcapade: The Hot Babysitter

by Syzoth on Dec 11, 2018
Group Sex

Author's note: this story was originally posted as "Mandy's Sexcapde: The Hot Babysitter". Due to overwhelming positive feedback, I've decided to make "The Hot Babysitter" into its own series, which will run concurrently to the "Sharing My Wife Amanda" storyline. Thank you for taking the time to read my works! -Syzoth **************************************...

Dodge Ball

by edgarf217 on Sep 12, 2017
Erotic Couplings

"Great game tonight!" she announced as she hoisted her schooner. "Us ladies dominated! It was the new socks!" "Whatever!" her team-mate replied. "If it wasn't for us guys shielding you ladies..." "Well I guess I could give a shout out to you guys too... Y'all did pretty alright." she smirked over her glass at him and took a big drink. "For boys that is!"...

Sharing My Wife Amanda Ch. 14

by Syzoth on Feb 26, 2019
Group Sex

This story follows Chapter 13 as well as "The Hot Babysitter 1". *************************************** "Hurry, Piper! Amanda will be home soon!" The 19 year-old's long blonde hair tossed in the air as she rode me wildly like a crazed cowgirl. From the flat on my back, I reached up to grope her firm breasts, squeezing them hard and mashing them together....

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...