Adventures In Babysitting!

Adventures In Babysitting!

One evening Jeremy’s parents were about go out for the evening to have dinner with some friends and then go to a movie which meant they would not be back home until around 11pm. The boy was in the living room when he heard the doorbell ring. “I’ll get it!” he yelled in an excited tone because he knew it was his favourite babysitter Alice. Alice was a beautiful, friendly 18 year old girl whom he’d had a crush on since she’d moved into the neighbourhood some two years ago. As he opened the door he saw her standing there on the porch. She was wearing a white t-shirt, sexy red shorts and white trainers on her feet.

He smiled and said, “Hi, Alice!” She bent over to kiss his cheek and replied, “Well, hello cutie!” He looked down her shirt seeing her lovely breasts since she was wearing no bra tonight. As he kissed her cheek he couldn’t help but blush. She grinned and walked in and Jeremy closed the door. He called out, “Mom, Dad, it’s Alice!”

As his parents came down the stairway his mother said, “It’s nice to see you again, Alice. Now you know the rules, right?”

“Yes, ma’am and I take good care of Jeremy, he is my favourite kid.” Alice told her as she rubbed the boy’s back making him smile brightly.

“Well, I think he is a little sweet on you too, dear!” his mother commented.

Hiding his face behind the teenage girl he retorted, “Mom, don’t tell her that!” Soon Mr and Mrs Thompson were ready to leave. They said their farewells and Alice even got paid in advance since she had come over on such short notice.

“Well thanks, Mrs T, you don’t have to pay me now, you know!” the girl told her.

Mrs Thomas replied, “It’s no problem, you are the best sitter we’ve ever had.” Jeremy agreed by nodding his head. But as soon as his parents had left the boy returned to the sofa to turn on his video game, challenging Alice to a game.

“I think you should have your bath first and it’s almost your bedtime.” She informed him as she turned off the game. The lad protested and said it was nowhere near his bedtime. He reached for the game to turn it back on. The girl ordered him to go upstairs.

“No way!” he shouted. “You’re not my Mom!” Alice was not going argue with him. She bent down and threw him over her shoulder in a fireman’s lift. She began carrying the protesting boy up the stairs to his bedroom. As she did so she smacked the struggling youngster’s bottom several times on his blue cotton shorts. SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! It hurt the boy and he got upset but he refused to cry in front of her so he just took it like a man.

“Okay, you win!” he said to her as she carried him into his room. She placed him on his bed and began undressing him. Soon he was stripped to just his thin white briefs. She began running the bath for him and then told him, “Now get in or I’ll give you a real spanking over my knee!” She went on, “I have a great idea. If we get this done early I will challenge you to three video games. If I win, you go to bed early. If you win let’s say you get to stay up a little longer and since I don’t think you have a chance of beating me because I’m pretty good at those games, you can be in charge for the rest of the evening and you can even spank me if you like!”

WOW! He was thinking as he got off the bed and ran to the bath. He climbed into the tub and drew the curtain so she wouldn’t see him naked in the bath water. He began washing himself all over. Soon his bath was over and he stepped out to dry himself. He heard Alice call to him, “Now get into your PJs and meet me downstairs!”

He smiled as he went downstairs and soon he was sitting on the sofa next to her dressed in his pyjamas. This is going to be fun, he thought as the game started. After a few minutes Alice won the first game and gave Jeremy that look that told him he was soon going to bed. No way! He was determined to win the next game. After a period of thirty minutes the boy pulled off a victory in the second game.

“That was just luck!” Alice said in a nervous tone but she was still confident that she would beat him in the third and deciding game. The third game was a marathon of some fifty minutes and the score was close all the way. Alice was now a little worried as she realised she may actually lose a bet with Jeremy which she never had before. She did everything possible to beat him but five minutes later her charge was the winner. She just shook her head in disbelief. “You must have cheated!” She stood up protesting.

Jeremy gave a wicked grin and said, “No, I didn’t. You’re just sore because I get to spank YOU now. I’m the one in charge now.”

The teenage girl tried to come up with reasons to get out of the bet, telling the boy she wasn’t really serious about letting him spank her and she was still in charge. Jeremy retorted that she had made a bet and she had to honour it. He advised her that if she didn’t he would tell his mother not to let her baby sit him anymore. She realised how much she liked this job and she loved his parents.

“Please don’t do that, Jeremy! Okay you win, you can spank me.” She thought to herself, What can he do to me really? After all he’s only 12 and not very big. He can’t hurt me! Next thing she knew the boy got hold of her wrist and pulled her towards him. “What do you think you’re doing!” she demanded.

“I’m taking you upstairs to my room.” He told her. “I’m gonna do it to you there!” Despite the outraged teenager’s objections Jeremy then threw her over his shoulder as she had done to him earlier and carried her up upstairs to his bedroom where her punishment would take place. The girl struggled for all she was worth to get down from his shoulder and thrashed her legs franticly. She could not believe how strong this kid was. He gave her six hard smacks on the seat of her red shorts as a warning of what was to come. SMACK! SMACK! SMACK! SMACK! SMACK! SMACK! He was turning the tables all right, BIG TIME!

Once inside his room Jeremy set the stunned girl down on her feet next to his bed and ordered her, “Pull down your shorts, Alice!” His babysitter stubbornly refused, saying that she didn’t have to and he couldn’t make her. “Guess I’ll have to do it myself!” the boy warned her. He slipped his fingers into the waistband of her shorts and, despite her embarrassment, he slide them down past her bum cheeks and her shapely legs. “Don’t worry, I won’t take off your panties since you never remove my underwear when you do it to me.” Alice was grateful for this at least.

The boy sat himself down on the end of his bed and instructed the older girl to get over his knee. “Let’s get it over with then!” she said as she laid herself across his lap. She was practically a grown woman but now she was going to be spanked like a naughty little girl. Jeremy smiled since he had never seen a girl of her age like this before. Her pantie clad bottom was on full display now. He commented what a nice ass she had. Alice felt his hand resting on her backside prior to the spanking she was about to receive.

“You’ve been a bad, bad girl, Alice, trying to wince on a bet like that and you’re gonna have a very sore bottom by the time I’m done with you.” Then he began to spank her. He did it a lot harder then she expected, harder then she had ever done it to him, and soon she was crying out with each swat. She did her best to reach back and cover her rapidly reddening bottom but the boy warned her to put her hands back or she’d have an even sorer behind.


After almost ten minutes of non-stop ass assaulting he finally stopped because his own hand was pretty sore by now. He let the now crying teen girl off his lap and she stood before him rubbing her well spanked butt. Jeremy addressed her saying, “Now then, girl, have you learned your lesson or do you want to go back over my knee for some more?” Alice told him she was sorry for being bad and she would behave herself in future. Tears ran down her cheeks. He grinned, knowing he had made her cry, which she had never been able to do with him.

Both of them then went downstairs into the living room to watch a movie. Jeremy sat on the sofa but Alice had to remain standing for the rest of the evening. Because of that little brat!, she was thinking. When the movie ended Jeremy went up to his room again and returned with a tube of lotion in his hand. “This’ll help!” he said. “Rub some of this in your butt before you go. Please don’t say anything to my parents about this!” He handed the girl a five dollar bill. “That’s half of my allowance if you keep quiet about this and come back again to baby sit for me. I like you really and thanks for being a good sport.” He apologised for spanking her so hard.

The girl agreed not to tell the boy’s parents but she implored him not to do that to her too often. He told her then that she was not the only babysitter he had made a bet with, a few other girls had found themselves over his knee and left the house in the same condition as herself. “It’s just for fun!” he grinned. “Pretty harmless.”

“Just for fun!” the flabbergasted teenager replied. “I can’t even sit down yet, I wouldn’t call that harmless!”

“You’ll be okay!” the boy told her. Alice then departed to the bathroom to apply some of the lotion to her abused rear end. It did ease the pain a little. When she came back to the living room she told Jeremy that the cream did help and she was glad he had given it to her. Her young charge said he hoped there where no hard feelings and then kissed and hugged her before going up to his room for the night.

A little later Jeremy’s parents returned home. “We’re back!” Mr Thompson said loudly. “Sorry we’re a little late. How did things go? Jeremy wasn’t any trouble, was he?”

“Not at all!” Alice told him. “Good as gold all evening. Maybe I’ll come back to baby sit for him again.” If I do, she was thinking, I’ll be sure to wear more underwear to protect my ass from that little bastard!

“Like a ride home?” Jeremy’s dad asked her. She shook head and said she would rather walk and she only lived a few blocks away anyway. She had lie on her tummy as she got into her own bed that night. She finally managed to drift off to sleep and she had a dream about Jeremy. She was naked over his knees and he held a hairbrush in his hand. He was applying the brush with much vigour to her exposed and vulnerable bottom. Just a dream or fantasy if you like? Or maybe a warning of what lay ahead for Alice!

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