Maddie the Babysitting Slut: Chapter 1 Dream Job Lost

This story is fictional. It started as a cyber chat play that just grew, producing long stories and a long series. Most of what is writing is mine but the thoughts, the direction, and even what is happening sexually comes with approval from my cybersex partner. Our fantasies came together, each story getting cleaner, more precise, and, hopefully, sexier. It became clear that the story was going to be centered around a babysitting cheerleader and wanting her to have forceful sex and be paid. What came is this series about ‘Maddie’.

I know the themes in this story are not going to be for everyone, taboo, and morally wrong. I am not saying that they are mine or hers but this is what came from our chats. I was highly encouraged to edit our talks together and post them in story form here on XNXX. Each story will have set up but you can scroll to the good parts quite easily. But since these chats were not meant to be stories, there will be gaps, especially in the beginning where transitions should occur.

All people involved are consenting adults, including the stories FICTIONAL main character Maddie.

“Maddie the Babysitting Slut – Chapter 01 Job Offer”

Maddie is a teen, eighteen to be exact. She is petite of frame but her long legs give her body the look of more, especially on the rare occasion she wore heels. Her 34 A breasts didn’t demand she wear a bra but she did so because that was what was expected and like any girl who had gone through puberty she had longed for her boobs so she wasn’t about to insult them by not wearing proper support. She kept her light brown hair shoulder length and found her eyes to be what she called ‘Dream Green’, rich and vibrant but not overstriking or bold.

Maddie is poor and lives in cheaper housing on the side of town that is looked down upon. Due to an essay and luck, she got the chance to attend a better high school. As she enters her senior year, it looks like she won’t be able to afford a car, college, or even her own apartment upon graduation. Maddie, however, did not let that keep her down. She found her way at the new school, made decent grades, got picked to be on the cheerleader squad, and even made a great friend named Emma.

It was Emma who turned her on to getting a job part-time in the area around the school to take advantage of people with better financial situations. It was this suggestion that would lead Maddie to a wealth of money, experience, satisfaction, and pleasure. It was this suggestion that leads Maddie to babysit and discover a dormant sexual slut.

“Hi, I am calling about the babysitting job? My name is Maddie. I am a senior at the local school. I do not have a car.” As Emma listens to the one-sided phone call between Maddie and her potential employer, she nudges her friend, picking up Maddie’s pleated skirt as a reminder, leading to an accidental nice royal blue panties flash for the bus patrons across the street. “I am a cheerleader which might interfere when you need me due to practices and games, but it helps me to be responsible, diligent, and a great multi-tasker.” Maddie recited off.

As Maddie hangs up the phone, she smiles brightly. “I got the job!” Maddie states, both girls squeal. “I go over today after practice to discuss pay, hours, and other possible chores while babysitting that will lead to even more money.”

Emma replies, “After practice? Go in your uniform, it will make that daddy happy. Plus it will help you get more cash out of him. Who knows? It might even lead to you finally losing that cherry. A win-win.”

“You say it like you lost yours! Besides, he is married. What would a grown man want with a girl like me? I’m little, got small breasts, and still a teenager.” Maddie says. Emma agrees but it just shows how much they don’t know about men and primal urges.

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“So that is the house. You get paid $20 an hour, eat whatever you like in the fridge, or before we leave I can order you something. Sometimes there can be additional chores, you do them if you want or got the time. I know between school, your activities, and this job, time and energy are a rare commodity for you. Do them if you choose and I will pay you extra in cash when we return.”

Maddie just followed her new employer around as she was given a tour, listening to him talking and answering questions as needed. ‘Wow, $20 an hour and can be more with the chores! They aren’t even that hard. Bet I could easily do two or three, get homework done, and still enjoy the TV and making sure the kid is ok.’ Maddie thinks to herself.

“Ok, since there are no questions. we will be gone at least six hours but it might be more. You have everything needed so relax, look after the kid, and enjoy yourself,” Maddie is told as the couple leaves out the door.

“Wow, she never said one word to me” Maddie muttered aloud as she proceeded to check on the kid and find some easy chores to do for extra money.

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“Why are they back so early?” Maddie wondered as it had been less than half of the time they were supposed to be gone.

“I tried it your way,” the wife screamed as she entered the house. “I went out, tried to have a good time but I didn’t. Now I am home, with MY baby and I am having a good time. Again, I knew it wouldn’t work, and that separating me from my baby was a horrible idea. So night, I am going to go be with our child.” She turned without a look towards Maddie. “Oh, and we are never doing this again so cancel the service.”

It took Maddie a moment to realize she was the ‘service’. As her heart sank, the husband entered the house better from the doorway.

“Maddie I am sorry that we came home early and even more so in a fight and again even more so in a fight that just ended in you no longer having a job.” As the man pulls an envelope out of his pocket, sorting through the different bill amounts and pulling out what is owed to Maddie. She can tell right away he has a fair amount of cash on him but it is unclear on the exact amount. He hands the money over to Maddie. “Here is what I owe you, it is the full amount because it is not your fault we came home so ridiculously early. I also threw in an extra $20. Sort of a severance package deal. Let me go upstairs, change and I will give you a ride home, so gather your things and make sure you got your homework.” He sulks off to go change and comes back down after a bit. Maddie has all of her stuff but is down cause she just lost her job and it is hard to find them, especially for $20, the ease of work, the hours, perks, and the extra pay. “Hey. Cheer up, Little Girl. I am sure you will find another job soon. A girl of your asset can’t be out of work too long. I let you say good-bye to the kid but you saw what the wife was like. Better not push our luck.”

The two head out to the car and Maddie gets helped inside. As her attention is elsewhere, Maddie flashes her royal blue panties out from under near her cheerleader skirt for a second time that day. This time, however, her audience is much closer and gets a way better look as her legs linger open for a couple of seconds. Soon the door closes and the driver seat is occupied and the two of them are on their way. One down and the other most definitely up.

“So I know that you said you were saving for a car, but have you thought about college any? I have seen your homework and you are smart. You understand everything it seems and you articulate your thoughts quite well.” Maddie explains her situation to her former employee about funds and hoping to get a scholarship. Maddie is talking so much she is unaware that he has led them away from her house and they are sort of out in the middle of nowhere.

“Where are we?” Maddie asks when they have been stopped for about 5 minutes.