Sissy Babysitter Stories

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My Wife & The Ebony Goddess

by CAPervert on Sep 12, 2017
Interracial Love

It was by far the happiest day of my adult life. It all began when my wife whom everyone says looks like Florence Henderson confessed to me that she had the hots for our next-door-neighbor. The 18 year old daughter of the only black family in our neighborhood who was our babysitter. The young woman's name was Diana and although my wife said she looked li...

The Babysitter

by Zorro69 on Sep 12, 2017
Group Sex

Fiona applied the last of her mascara then started to pack her make up away. The doorbell rang and she walked into the hallway. "Darren, the babysitter has arrived are you nearly ready?" She opened the front door. "Evening Ying, come in and make yourself at home." Ying, the daughter of a family friend, was now Darren and Fiona's regular babysitter for their...

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...

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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...

Teaching My Babysitter

by MissRose18 on Nov 22, 2017
Group Sex

Being a single mother is very difficult and I rarely get to go out. It is just my luck that the one time I accept a date he cancels. Oh well, I thought, I didn't actually want to date him. I knew I just needed a good fuck. It had been so long since my divorce, I was starting to forget what a real cock felt like. I guess my toys will have to do for tonight I...

My Babysitter's a Stripper

by whodatty on Sep 12, 2017
Erotic Couplings

It was getting close to midnight on a Friday night. I had been out with a couple of friends shooting pool. They decided to call it a night but I wasn't quite ready to turn in yet. After all it's not often that I get to stay out past "curfew" but since my wife, Heather, had taken the kids up to visit Grandma for the weekend, I could let my hair down for once....

Babysitter Challenge

by CopyCat13 on Sep 14, 2017
Exhibitionist & Voyeur

Some girls just need a little kink in their lives and Amy is one of them. For the last couple of weeks she's been going to an online chat room and getting naughty challenges from online strangers. Most of them have been either really tame like going commando or else way too extreme like getting "Sperm Bank" tattooed across her face. But every once in a while...

Tales of Unintended Nudity

by ewong on Feb 5, 2016
Exhibitionist & Voyeur

You are an attractive woman, who somehow through the course of the day, ends up naked. You can be at home, school, work, or any place that you feel would be the worst place for an attractive woman like yourself to be caught naked. You can be an average woman, who has a job or goes to school. You can be a wife and mother. You can even be a celebrity. It's up...

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My Naughty Babysitter

by Indianaboy6555 on Mar 25, 2019
Erotic Couplings

The wife and I had two kids, and it had been years since we had gotten out for a night. We'd tried the babysitter thing, but it seemed there something about all of them that the wife had issues with. We couldn't even go out and enjoy a movie without her leaving to call home and check up on everything. Don't get me wrong here. I understand her concerns, but t...

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...