Babysitting Stories

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BabySitting

by Ashson on Sep 16, 2017
Loving Wives

I'd been divorced for a couple of years when it happened. My wife had one day decided that she didn't like the married life and just shot through, leaving me with two kids to look after. I won't say it was easy but, with the help of friends, I coped. One of the people who chipped in to help was my sister-in-law, Faye. Nice young woman, married and with a co...

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...

Babysitting

by MNGuy on Sep 11, 2017
First Time

The houses were all quiet, bathed in the moonlight. I shut the curtain and paced back across the living room. It was already past two o'clock. I was bored, there was nothing on televisions, all the stations had signed off over an hour ago. My eyes were to tired to continue reading. This was going to be a longer night than I had bargained for. I laid back dow...

Babysitting

by HeatherMaureen on Mar 6, 2018
Transsexuals & Crossdressers

It had been so long since I used to babysit for my sister and dress up in her things. That's where my obsession had started. Then as I got older I stopped babysitting for her. There was little chance for me to do any dressing at home and I pushed the idea to the back of my mind. One night when my little sister was already babysitting for my older sister I...

Babysitting with Benefits

by Darkforeboding on Sep 13, 2017
Toys & Masturbation

My boyfriend and I love watching porn videos, but I have to smile when we see one where somebody seduces the babysitter. The reason I smile is because it isn't ever the way they show in the movies. I know, because it happened to me. I know that a dirty movie isn't realistic; it's just somebody's fantasy on film. But I can't help but think about it because i...

Babysitting the Baumgartners Ch. 03

by Selena_Kitt on Sep 12, 2017
Exhibitionist & Voyeur

I buried my red, flushed face into the coolness of my pillow and decided that I wasn't going to leave my room. I just couldn't face them, after what had happened. When Mrs. B knocked on my door for dinner, I told her I wasn't feeling well again. "Anything I can get you?" she asked kindly. I shook my head and called a muffled, "No!" into my pillow. Downs...

Babysitting the Baumgartners Ch. 05

by Selena_Kitt on Sep 19, 2017
Exhibitionist & Voyeur

They were all playing in the surf when I stepped outside into a wall of heat. It actually smelled and tasted like rain, although there wasn't a cloud in the sky. The humidity was like that down here, I'd discovered, and it seemed to force beads of sweat to the surface of my skin the minute I walked out of the air-conditioning. Mrs. B saw me and waved, and...

Babysitting Slut

by KatieMack on Sep 12, 2017
Fetish

It was almost five when her cell phone started ringing, five o' clock. Time for Law and Order to start... she could ignore the phone, let it go to voicemail... but instead sighing and stabbing at the mute button on the TV controller Jillian answered the call after noticing that it was the house number of the family she often babysat for. "Hello" she said,...

Babysitting... And Sitting and More

by Cinnyperez on Sep 18, 2017
Erotic Couplings

*All characters are at least 18 years old* ***** The jingling of keys at the front door woke me up. There was a light thump against the door and then a chorus of giggles from a man and woman. Mr. and Mrs. Jennings were back from their night out. I kicked off the blanket covering me just as they opened the door. They walked in arm in arm, Mrs. Jennings str...

Babysitting Her Sister

by badboisumtymz on Sep 13, 2017
Erotic Couplings

I had been going out with Cara for a little over a year when things had begun to change. I still loved her, we still went out barhopping and our sex life was out of this world, but things just weren't the same. You see, Cara was different than most of the girls I had been with. Although she was attractive and had the best personality in the world, Cara was t...