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Babysitter Stories

babysitter

Caught By My Boss

Babysitting job bliss

It was a boring Saturday night. I was 16 and had no plans. It was summer and all my friends were out of town. I was watching TV when my cell rang. It was Mrs Sellars from next door. She was 28 and beautiful. I hadn't had sexual feelings for women before and was still a virgin 'both' way, having had a few boyfriends. She told me that she needed a babysitter for her two year old, who was already in bed. Diane, that's what s...

The Babysitter - Part One

I never thought it would ever go this far...

It was a day like any other. My wife was at work and I was at home with the babysitter. Let me give a little bit of background to make sure that all will understand. I work an on-call 24/7 shift as a tow truck driver and my wife and I have three kids. So, it is very necessary for us to have a babysitter who is there in the event that I must leave the house to go on a call. The babysitter's name is Ashley; she is a just tu...

Veronica the Babysitter

Veronica was a slutty babysitter; fucking the single father of 3.

Veronica was an 18 year old firecracker. With her long tan legs, perky titties and plump ass, the men were always looking at her, fantasizing about her. She was truly one of a kind. Her long, curly brown hair cascaded perfectly down her back, and her big green eyes hypnotized man after man. But she was no slut. She was smart, and only slept with the men who proved worthy. As a part time job, Veronica picked up babysitting...

Sitting The Twins

Babysitting turns fun.

Chapter 1 I'm almost an adult, by that I mean that while I am an adult by law, my last birthday I was twenty-one, I'm still in college so I don't feel quite like an adult yet out on my own working and living alone. I'm still a year away as I start my senior year this fall. So, I'm taking the summer at home with Mom and Dad; I'm their only child, and now they've felt more free to travel and do things on their own. That's w...

Sibling Arrangement Pt.1

brother gets into trouble and asks his sister for help, all while the parents are out of state.

I wish I could say there is a better way to start my story, but this is the best place as any. It started 3 days before my parents Jennifer and step dad Kieth left to go on there honeymoon, which meant my 21 year old sister Kayla would be baby sitting me, even though I argue with my parents that im 18 and I can be trusted, but they kept saying things like, "you said that before you and your friends blew up the shed," and...

Setting Up Hubby With Our Babysitter

Our babysitter had a baby of her own, just didn't have a man of her own, so I let her borrow mine.

Chapter 1 Aaron and I met in college at the University of Wisconsin. He was majoring in mechanical engineering and I was majoring in finance. Yes, rather different career tracks but we had a lot in common. The main area we shared was our bodies. I first had sex when I was sixteen and was hooked from then on. I did know some girls whose first experiences were bummers but mine was wonderful. Just got the right guy, I guess....

A Little Extra Pay

My boyfriend and I got caught by the parents I was sitting for and they decided to have us finish.

Chapter 1 Most of my friends have done some babysitting for extra money, it's just been an age-old way for girls and some boys to make spending money. My case is a little different and I've pretty much given up babysitting except for the Carpenters, Irene and Jack. I think you'll understand when I explain. It all started with a routine babysitting job with them, keeping Rita, their two-year old while they went out. Now, m...

There's A Babysitter in my bed!

You wouldn't believe what I find in my bed...

It has been too long since I’ve touched a woman…. I thought as I walked in the front door, stumbling a little from the few drinks I had at the bar after work. Continuing inside I look at my kitchen clock its 8:55PM past my son Bens bedtime. Looking down I see the babysitter Carmen reading on the couch and I couldn’t help noticing what she was wearing, a pink mini skirt and a white tank top, with no bra! Just looking at he...

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That's My Babysitter In That Porn Video!

I notice my substitute babysitter on a free porn site and fall in love.

Following my divorce, my company transferred me across the country and the custody agreement with the ex allowed me to have my daughter for six months then she would go back to her mother’s place on the West Coast for another six. I had a deadline rapidly approaching and desperately needed some uninterrupted time in my home office to complete my reports. I called my usual babysitter and she apologized but had accepted ano...

Servicing A Need

Lots of girls do babysitting to earn extra money but I added a few extra services.

It's a secret and I'm only telling you. But you have to promise you'll never tell anyone, ever. Okay. Well, it all started when I was sixteen. Like lots of girls, and boys, too, I guess, I did babysitting to earn extra spending money. My first job was with the Parsons, she was a friend of my mom. They paid me four dollars an hour and my first job netted me twelve dollars. I sat for them several more times and the third ti...

Anonymous

Telling Mom I'm A Crossdresser Part 14: Back to the spa and a familiar face.

Part 14, yes I feel it is long but please read the whole thing you will not be disappointed.

Part 14: Back to the spaI'm sorry this story is a fair bit longer then my usual ones however I didnt want to separate thes and have another story with almost no sex in the first one so soon. Having said that I hope you enjoy my story and please read the whole thing. I promise you will not be dissappointed. I woke up the next morning lying next to mom in her bed. I was wearing a pair of white stockings and a corset and mom...

Sexual Awakenings (Chapter Eighteen)

A 16 year old gets to fuck his 21 year old babysitter doggie style while her friend watches!

Chapter 18: Doggie In The House!A few hours had passed, and I awoke to find myself all alone in the bed. I could hear the girls mumblings of voices gently from downstairs, as I rose up, placed on a pair of boxer shorts and began to descend down the stairs. Entering the living room, I discovered both Amanda and Julia sat upon the couch, wearing very little upon their beautiful soft bodies, and chatting."Oh, hello sleepyhea...

Sexual Awakenings (Chapter Seventeen)

A 21 year old female house sitter awakens a virgin 16 year old boy's sexual pleasure!

Chapter 17: Let Me Take You For A Ride!It hadn't been many minutes now since Julia had taken my virginity, as I laid upon the bed at her side, and soon accompanied by Amanda who had watched me fucking her best friend for the first time while she masturbated across the room in a chair. The three of us, laying upon the large comfortable mattress as the experience of what had taken place had taken it's toll upon me a little...

The Babysitter

A sweet babysitter seduces her employer

The Babysitter She gave a light tap on the door, knowing that there was a baby in the house probably trying to sleep. The tapping was loud enough to alert the child’s mother who was sat in her living room. The house had been silent so the sound startled the young mother who, up to now, had been playing through the infinite possibilities of the night ahead in her mind. The more she thought about it, the more nervous and ed...

Sexual Awakenings (Chapter Sixteen)

A 21 year old female house sitter awakens a virgin 16 year old boy's sexual pleasure!

Chapter Sixteen: The Watcher In The Corner!While Julia showed me her beauty and sexual pleasure as I fucked her, I was unaware that at the same time her best friend Amanda watched every moment of it. After she led me upstairs, and into the bedroom where Julia awaited me and that first moment of pure bliss and pleasure happened for myself, Amanda did not leave. In fact, she stayed.After letting me go, Amanda stepped across...