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Babysitting: A How-To guide

Bobby lived in New York City, in Manhattan, the center of the known universe as his father used to say before he moved out and he and Bobby’s mom got divorced. This didn’t particularly upset either his mother, or Bobby. Before he moved out, his father was never home. He had inherited a fortune when Bobby’s grandfather had died, so had business interests all over the world, which he visited regularly. When not traveling overseas, his father traveled around the US. He was probably only home a couple of days in a month, except maybe at Christmas, so Bobby was raised by his mom, and matured listening to her complaints about his father. Bobby concurred with most of them.

Both his parents had been part of the social scene when they were married, his mom kept up her schedule after the divorce. She regularly attended charity events and went out to the theatre and opera and symphony with a variety of different men, who came and went. One would be regular for a while, sometimes, but Bobby couldn’t remember any of them lasting very long. Some paid attention to him, some ignored him and Bobby really didn’t care which.

One problem his mother constantly complained about was getting babysitters for him. He terrorized them, gluing their shoes to the floor with superglue, cutting their clothes into superhero costumes, refusing to obey them at all. He was naturally rambunctious, loud, and, since his father was gone, thought of himself as the man of the house. It was a heady feeling for a youngster, seeing himself in charge. Maids who came in and cleaned, came and went. Bobby terrorized them while they were at the house, supervising every move. Few took it very long. Babysitters were just “help” not worthy of his respect. Mom complained that finding babysitters took up all her time. She begged Bobby to listen to them, she paid above going rates, and she threatened him. Nothing she tried worked. Until one day, that is. One of her friends came over and mom was complaining about it and the friend suggested mom try the university, lots of students needed money and would view watching Bobby as a great job.

The first two were like all the ones before. They lasted a time or two then quit. The third one was the charm. When she came over the first time to watch him and was introduced to Bobby, his mom could immediately see a small difference. Bobby was obviously pretty smitten. Anyone could see why. The girl was quite attractive, blonde, tall, dressed and made up fairly well considering what his mom thought must be a really limited budget. She had a wholesome charm though, and a smile. She was very young, hardly more than a child herself. Bobby’s mom thought that she would at least be good for a couple of times, but she was skeptical this babysitter was going to solve her long term problem. Her name was Emily. His mom introduced her to Bobby who was following along to watch as Emily was shown the entertainment center, the kitchen and bathroom and given the list of numbers to call in an emergency. His mom then wished Emily good luck on her way out the door, as usual, a little late for her next event.

When his mom had left Emily went to the sofa and sat down with Bobby right behind.

“Boys are the boss of girls.” was his first comment.

She looked at him and smiled a brilliant smile, “Really?”


She kept smiling as she rummaged through her backpack until she found what she wanted, a book, opened it and began reading, ignoring Bobby.

“Listen to me. I want a coke.”

She looked up from her book, smiled at him and said, “So what? What do I care?” She bent down back to her book.


His scream was pretty loud but instead of prompting her to pay attention to him, she ignored him, rummaged in her backpack again and came up with her phone, put in some earphones and started listening to music.


Produced no response. He grabbed for her earphone wire but she caught his hand, twisted his wrist and pushed him off the sofa.

She smiled at him, “Now, stay off the sofa. And keep your hands off my stuff.”

He considered this and jumped back on the sofa and grabbed for her backpack.

She caught him again, only this time didn’t let go. She dragged him and her backpack to the nearest door and rummaged through it and pulled out a couple of sets of handcuffs. She explained everything as she did it.

“I have four younger brothers, they’re all older and stronger than you. I can beat them all up. They all listen to me. These handcuffs, though, they’re for my boyfriend. He gets frisky sometimes and I use them on him, and he can’t stop me.”

She cuffed one wrist to one doorknob, the other to the other and left him hanging there, stunned.


“If you don’t quit screaming, I’m going to stuff a rag in your mouth.”


She got up from the sofa, rummaged around in her backpack, pulled out a dirty sock, showed it to him, held his nose and stuffed it in his mouth, smiling all the time. She went back to her reading.

His muffled cries were not nearly so loud, and since they hardly had any effect at all. He eventually quit.

After he’d been quiet for a few minutes, hanging there by his wrists, she got up, went back to the door her charge was cuffed to and stood there, looking at him, and smiling.

“Now, if you’ll promise to quit screaming, I’ll take my dirty, stinking sock that I wore all day out of your mouth. Just nod yes. If you like that sock that’s been on my foot all day in your mouth, don’t do anything and I’ll leave it there for you so you can taste me. You’ll like that too. Your choice.”

He looked confused, but finally nodded yes.

“I’m going to tell my Mom.” Came out as soon as the sock cleared his mouth.

She smiled, “No you’re not.”

“Yes I am!”

“No you’re not. You know why?”

He looked puzzled. “Why?”

“Because I’m pretty and if you tell her, I won’t ever come back.” Her smile was gorgeous.

“It’s not fair. Unlock me.”



“You’ve been a brat, I don’t tolerate brats, as far as I’m concerned you can stay locked like that until your mom comes back and I’ll walk out of that door,” she paused and emphasized, “Forever.”

“Please unlock me.”

“Oh?” She smiled, “That’s a magic word. I honestly didn’t think you knew any magic words.” She looked thoughtful, “Well, with the magic word, I guess I have to unlock you, if you agree to play a game.”

“What game?”

“Whatever game I say.”


“OK, what?”

“Unlock me.”

She looked triumphant, “No magic word!”

“No, Please, please unlock me.”

“Darn. And you knew to say it twice. Darn. So I guess I have to. The game is Queen and Slave. I’m the Queen and you’re the slave. If you don’t do everything I say, I’ll lock you up again. Do you understand the rules?”


“OK, slave, let me get the keys.” She walked back to the sofa, bent over the back, lifted her leg in the air and rummaged around in her backpack. Bobby could see her panties and he was enthralled. She came back, twirling the keys on her finger. She smiled as she unlocked the cuffs one at a time.

“Now slave, I am going to return to my throne, crawl behind me and stay on your hands and knees in front of me.

He crawled behind her as she slowly walked back to the sofa, looking over her shoulder and smiling a couple of times when she saw that he was still on his hands and knees. She sat down carefully on the sofa and crossed her legs so her shoe was right over his head and he could see the back of her legs. He knew he could see her panties again if she changed her legs.

She put the dirty sock from her backpack on the edge of the sofa and said, “This is the sock I put in your mouth. It’s defiled. This is the other sock I wore today. It’s pure. Take it with both hands and put it up to your nose and breath in and smell how wonderful my feet smell and tell how much you love smelling my dirty socks.”

Her smile was overwhelming as she leaned forward with the sock dangling from her fingers and Bobby took it in both hands and lifted it to his nose and sniffed loudly.

“I love smelling your dirty socks.”

“You didn’t say ‘Your Highness’.”

“I love smelling your dirty socks, Your Highness.”

“Well, I thought you were going to be a dumb slave, but you’re not, I see. Do you think I’m pretty?”

“Yes, your highness, I think you’re pretty.”

“Thank you.” She laughed, delighted. “Are you going to tell your mother how much you like me so I’ll come back?”

“Yes, Your Highness, I am going to tell Mom that I like you.”

“Good. I like you too. You are going to be a good slave. Would you like to kiss me?”

Bobby couldn’t believe his ears kiss her? “Yes, Your Highness, I’d like to kiss you.”

“I don’t know. A slave shouldn’t be allowed to just kiss me. You should kiss my toe. Do you want to kiss my toe, slave?”

“Yes, Your Highness.”

“I like this. Will you promise to do anything I say forever?”

“Yes, Your Highness.”

“Well, since you’ve promised to be my slave forever, you can take off my shoe and kiss my toe, which will be your reward.”

“Yes, Your Highness”.

“Now think, if you tell your mother about this game, she won’t let me come back, so, if you kiss my toe, you have to keep it secret from everybody. Do you still want to kiss my toe?”

She kicked her foot tantalizingly in front of my face. Bobby was hypnotized. “Yes”.

“You didn’t say, Your Highness”.

Bobby answered, “Yes, Your Highness,” with his eyes glued on her shoe, “I want to kiss your toe.”

She put her elbow on her knee, rested her chin on her elbow, and held her leg out, “Take off the shoe of carefully and put it aside, and just kiss the top of my big toe, no licking and slobbering all over it, no putting it in your mouth and running your tongue all around it and savoring how wonderful it is. Just pucker your lips and kiss my toe.” Her pause was dramatic, “If you dare, slave.”

Bobby took her shoe off and put it aside then lowered his lips to her toe and kissed it.

She laughed, “Oh, that felt better than I thought it would! Wait, you don’t kiss other girl’s toes, do you, slave?”

“No, Your Highness.”

“Then how did you get so good at it? Never mind. Don’t answer that. Now go get me a coke.”

She leaned back and picked up her book, Bobby got up but before he could take a step toward the kitchen, “No, no, always crawl in my presence. You’re my slave forever!”

He crawled to the hall, got up, ran to the kitchen, got the coke, came back and crawled back to Queen Emily and held up the coke.

“Open it for me.”

Bobby opened it.

“Now, take a drink, not a big one, so that if it’s poisoned, you’ll be the one to die.”

“It’s not poisoned. Your highness.”

“Oh yeah? If that’s true, why won’t you take a drink?”

Bobby considered this. Emily was different from anybody he had ever met. He shook his head and took a drink and offered it back to Emily.

“Wait a minute, let’s make sure you don’t turn purple and die or something. Now, while we wait, slave, you can tell me why you think I’m so pretty.” She looked very serious.

“I don’t know, Your Highness, you’re just pretty.”

“Well, is it my face, or my lips, or my eyes, or my legs?” and she raised her leg up and looked at him, “Well”.

“It’s all of you, Your Highness.”

“Oh. OK. Everything, that’s OK, I guess. Wait, maybe you didn’t drink enough before, maybe it takes more coke for the poison to work. Nice try. Take another drink.”

Bobby looked at her, shrugged his shoulders and took another drink.

“Kiss my toe again.”

Bobby leaned down and kissed her toe.

“Always, always, say ‘Yes, Your Highness’ to acknowledge you heard me and are obeying.”

Bobby considered this. “Yes, Your Highness.”

“You’re going to have to pretend you’re not my slave in front of your mother. It is going to be difficult, you are such a good slave.”

“Yes, You’re Highness.”

“You may kiss my toe again.”

“Yes, Your Highness,” he leaned down and kissed it.

“Do I see a little tinge of purple around your eyes? Ah hah, take another drink, slave.”

Bobby looked puzzled, but he said, “Yes, Your Highness.”

“What grade are you in, slave. I want to know so I know when you can get a job and start making money for me.”

“I’m in 4th grade, Your Highness.”

“Take another drink of that coke and kiss my toe while I think about that.”

Bobby took a drink, remembered, said, “Yes, Your Highness”, and kissed her toe.

“That was in the wrong order. Do it again, this time right.”

Bobby thought, “Yes, Your Highness,” took another drink and kissed her toe.

She shifted her legs and Bobby saw her panties again. He couldn’t believe it. She was beautiful.

She looked down at him, “You are a better slave than I thought you’d be. I like you.”

Bobby didn’t know what to say so just said, “Yes, Your Highness.”

“Or is this just a trick to get me to drink some poisoned coke? I know, finish that coke and sit in front of me while I watch you turn purple and die, gasping out, ‘I’m sorry Your Highness, you’re beautiful’ with your last breath. Go ahead, finish it.”

Bobby started to finish the coke, remembered, said, “Yes, Your Highness” and drained the can.

She said, “Put that can on the table with your dying effort slave. Then come back in front of me so I can watch.”

“Yes, Your Highness.” Bobby crawled to the coffee table, put the empty can on it and crawled back.

“You aren’t thinking about running away, are you slave?”

“No, Your Highness!”

She leaned back and shifted her legs again, flashing her panties.

“I don’t like to hear ‘No’ slave, I like ‘Yes’. Always figure out a way to say ‘Yes’, do you understand?”

“Yes, Your Highness.”

“I mean if I wanted to ask you if you wanted me to get up, take off my panties and put them over your head, I’d want to hear, ‘Yes, Your Highness’, not ‘No’, do you understand?”

Bobby stayed on all fours with his mouth open, “Yes, Your Highness.”

“Oh yeah, well let’s try it then. Do you want me to take off my panties and put them on your head and you wear them like a hat?”

Bobby gasped, “Yes, Your Highness.”

Emily got up, took off her panties, looking Bobby right in the eye with a little smile and held them out, “No, you put them on over your own head. You want to, slave, don’t you?”

He gurgled, “Yes, Your Highness”. He took the panties and put them over his head. She sat back down, smoothing her skirt so he couldn’t see.

“Well, sit back down slave.”

The panties were a little wet, and Bobby let the smell of them surrounded him and the way she looked through the panties with that smile on her face almost knocked him over.

“Take a deep breath, drown in my smell, slave,” Queen Emily, his Queen, said.

He took a deep breath. It was intoxicating.

“You’ve been such a good slave, turn them around so you can smell all of me. You’d like that, wouldn’t you slave?”

“Yes, Your Highness.” He turned the panties around.

She smiled, “Breathe deep, in and out, in and out. Use your tongue and taste the panties I wore all day, slave, be mine.”

He was doing this when he heard his Mom come in the front door. “I’m home!”

“Quick, take my panties off and run into your room and put them under your pillow, you’ll have to hide them, hurry.”

And he took the panties off and ran to his room, just before his mom entered from the other door to find Emily sitting on the sofa reading her book.

His mother looked around in wonder, “This looks peaceful.”

Bobby came back in the living room, “Hi, Mom.”

His mom looked at the scene in wonder. “Everything OK?”

“Sure,” Emily said. “Bobby was so sweet, and fun. We had a great time.”

His mom stared at her and then to Bobby, “Well, ah, Bobby, ah…”

Bobby answered, “We talked and played a game. It was fun. Can she come again, please, Mom?”

His mom showed her out, slipping a $100 bill in her hand. When they got to the door, Bobby came running up, “Good bye Emily! I had fun!”

Emily smiled, “Me too. See you next time.” And gave him a high five and was on her way.

Some babysitters just know what their charges like and have a real knack for it, was all his mom could think.
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