Babysitter Anal Stories

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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...

Wife Pulls A Fast One on Him

by freefred on Sep 17, 2017
Loving Wives

Many thanks to volunteer editor falcon29 for his excellent assistance on this story. Joe rolled over for the umpteenth time and look at the clock at the head of the bed. Only four o'clock! This had been a long night. He had been tossing and turning all night and couldn't sleep and he knew why. In his mind the question kept repeating over and over, "Was his...

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...

Maxie Reckless and the Kith #06

by RavynsLand on Sep 16, 2017
Transsexuals & Crossdressers

Waking up draped awkwardly over a too-small Kith bed makes everything feel all too real. Like when you wake up from a night of drinking, and your hangover is so intense that it feels like you're in a completely different world... except this time, I am in a different world. Suddenly the dreamlike nature of being dragged into an underground haven of alien fai...

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...

Koko Gets The Job Done

by buffaloraven on Sep 16, 2017
Group Sex

I hadn't known Koko that long, but that's the glory of a university town: plenty of new faces all the time, and lots of them hard up for money, and with the spare time to earn some. And I'm not talking about sex, pervs. Well, at least not PAID sex. But we'll get to that later. As I was saying, Koko had moved in up the street from me earlier that summer wit...

Having a Babysitter Ch. 03

by mattchat33 on Sep 12, 2017
Mature

The next few days I thought about Sarah more and more, remembering the wonderful time I had with her the last time I drove her home from our house after babysitting. I kept on wondering whether I would be able to spend some more time with her and hopefully have even more fun with her. However there wasn't any opportunity for my wife and me to use a babysitt...

Adventures in babysitting

by Ashley16 on Feb 18, 2017
Exhibitionist & Voyeur

Summer, an incredible time of year. Exams were over, the school year was coming to an end and all that was on anyone's mind was parties, gossip and sex. I was no exception. I'd lost my virginity last year at my friends house party, while half the party listened from outside the door. This earned me quite a reputation, first as a slut ready to fuck half the s...

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Seduced by the Babysitter

by guidosgal on Sep 12, 2017
Erotic Couplings

I rushed out of work a half hour early, almost giddy with anticipation. Tonight was going to be a long held fantasy come true and my cock was already rock hard just thinking about what was to come in less than a few hours. Plans had been set in motion weeks ago and would finally come to fruition soon after I arrived home. I prayed for light traffic as I pull...