The Babysitter

Stories about boys ending up in compromising situations, preferably naked and embarrassed, as the name suggests.
VansFic
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The Babysitter

Post by VansFic »

Hello,

This is my first post here and working on getting myself into the swing of writing fictional stories. I've taken a short film as inspiration for my story and I started off by taking the short and writing it out, then it'll continue with more ideas for the main characters. Hope you enjoy!

~~~~~~~~~~~~~~~~~~

Jimmy was on the phone with his friend in the Abbott’s kitchen while Sara watched the microwave waiting for their popcorn to finish. The 16 year old had agreed to babysit Sara for a friend of his mother’s, after some insisting. Sara’s mother didn’t want her watching much TV, so the pair had decided on playing some board games after making popcorn. This wasn’t how Jimmy would typically spend his Friday night. More often than not he would be with his friends, seeing a movie, playing videos or just hanging out in general. In truth, he was kind of glad he had an excuse to not hang out tonight, as his friends had found out about a party planned to attend. Jimmy had planned to go as well until he had stupidly bragged how he would bring his girlfriend Wendy, so they could all meet the older woman he had been fooling around with the past couple of months.

One problem, there is no Wendy. He had created the lie in a stupid moment of envy when his best friends were talking about how they had gone out with some girls from their school and the bases they made it to, and the ones they anticipated making it to. The lies came out of his mouth before he even realized, and once the lie had started he couldn’t find a way to back out without looking like an idiot. There was no way he could just admit he made it up, he’d rather face a firing squad.

Sara leaned against the counter in front of the microwave watching the popcorn bag jump and shift as the kernels within popped. She was wearing her swim goggles, for no reason other than she had just been telling Jimmy all about her swim practice and teammates. She told him how the boys on the team were all immature and she didn’t like any of them but she could tell Jimmy wasn’t really listening. Sara may have only been 12 but she thought she was more clever and smarter than most of her age and was annoyed that Jimmy wouldn’t recognize that.

The brunette girl looked at Jimmy as he turned his back to her with the phone held to his ear, she could overhear him talking to his friend even though he kept his voice down. “Really? You did it? Really? Wow,” his voice drifted off slightly at this last comment. Sara was curious what they were talking about and pretended to be paying attention to the microwave while focusing her attention on the teenage boy.

“In a bubble bath?” Jimmy let his voice rise a little with that question, momentarily forgetting he was trying to have a secret conversation with his charge only a few feet away. “Me? What do you think man, of course I did. Many times. Wendy’s got a whole jacuzzi at home.”

Jimmy was starting to pass by Sara as his friend questioned him about his mysterious girlfriend, “you’ll meet her man, just not tonight.” Jimmy felt the heat rising in his face as his friend doubted he was really dating anyone and walked over to lean on the kitchen counter, “fuck off I’m not making it up, I do have a girlfriend. You think I don’t want to go to the party tonight? I have to stay here and babysit this idiot girl.” Jimmy was fiddling with the breadbasket lid while trying to find a way to deflect his friend’s suspicion without realizing Sara was watching him behind his back.

“Hey, but listen to this,” Jimmy suddenly added with a spark of inspiration as he paced to the otherside of the kitchen, Sara now more openly followed his moments as her dirty blond haired babysitter didn’t even seem aware of her presence. “Wendy said that after the girl goes to sleep she wants to come over and….” he paused and looked back slightly, Sara had turned her head back to the microwave as if she hadn’t heard a word, “well, do it on the kitchen floor. Yeah, told you dude, she’s an animal.” Now Jimmy was grinning as he could hear his friend’s envy over the phone line.

“Yeah. Sure. Great. Later, “ Jimmy ended the call with plans for each of the boys to share their exploits the next day.

Walking back over to Sara and the microwave, Jimmy asked, “is it ready?”

“Fifty-four seconds,” was Sara’s reply as she turned to him and boosted herself up to sit on the countertop. “Who’s Wendy?” Sara asked. Giving away she had overheard at least some of the conversation with a sly smile on her face.

“None of your business,” said Jimmy with a straight look on his face to the younger girl.

Sara changed the topic of the conversation instantly, “did you know I’m the fastest swimmer on the swimming team? And Coach Harris said that next year he might send me to the Olympics.” She wasn’t sure why she made the boast, even she knew there was no chance the fastest 12-year-old swimmer would go to the Olympics. She just wanted to try and get Jimmy’s attention.

“That’s nice,” was the non-committal answer.

Sara looked more directly at the boy and asked, “Jimmy, what’s a blowjob.”

“What?” Jimmy asked more in surprise than anything else, shocked to hear the question come out of her mouth.

“I’m old enough to know,” Sara argued, the unspoken rebuttal to her question. She was right to insist because Jimmy was quick to reply with, “no you’re not.”

“Yes I am,” she insisted again, her tone taking on an indignant look and her voice matched. She knew she was smart, why couldn’t he see that she was clearly mature enough to know?

The blond boy felt unsure how to avoid both arguing with her about being old enough to know the answer and about answering the question itself. Sputtering his best response, “well, then, ask your mother or…. Ask your mother,” he said nodding definitively.

Jimmy looked at Sara sideways while trying to turn his attention back to the microwave as it counted down the final few seconds but the girl seemed unsatisfied with this ‘final’ answer. That’s when Sara realized something, “you don’t know do you?”

Jimmy was even more confused at this accusation. He went from trying to deflect having to explain a blowjob to the girl he’s babysitting, and now being accused of not even knowing what it is. Sure, maybe he’s never had one, but he definitely knew what they were. Mostly. He could also feel heat rising up his neck and into his face like when his friend called him out for lying about having a girlfriend. He hated how easily flustered he got, “of course I do, I’m just not telling you.” Even to his own ears his argument sounded weak.

“You don’t know,” Sara said in a teasing voice.

“I do too,” he argued back in a raised voice.

“I admit that I don’t know. I mean I maybe a little ignorant, but at least I’m not a liar,” Sara’s retort was aimed to make Jimmy more defensive and prove he knew about the sex act.

And it seemed to be working. “I’m not lying either,” the teen boy insisted.

“Then prove it,” Sara threw back at him, an easy challenge to show he was as mature as he put on.

“Fine.” Jimmy gave in without even thinking about the fact moments before he had argued there was no chance he could tell her about blowjobs. He paused for a moment to try and collect his thoughts, how could he describe a blowjob to a 12 year old? “A blowjob is when… it’s when a girl. A woman,” Jimmy could feel his face starting to turn red, “umm, like in a bed, or actually anywhere, or in a bubble bath. And sometimes the guy wants, she wants to,” he started waving his hands in the air vaguely, this was a disaster he knew but had no idea how to salvage it. He finally stopped and sighed, his hands falling as he realized he had no idea how to describe something he didn’t fully know about.

The shrill beep of the microwave was his saving grace in that moment. Jimmy quickly moved to open the microwave and pulled out the hot bag of popcorn, he didn’t care that his fingertips were burning as long as he didn’t have to keep trying to answer her question. He opened the contents into the bowl they had prepared to the side and tossed the empty bag back on the counter. Turning his back to Sara to avoid looking at the reaction to his terrible failure of an explanation he started walking out of the kitchen to find a board game he can distract her with and never return to the question of blowjobs ever again.

Just as he thought the subject was dropped he heard Sara behind him, “uh huh, you don’t know shit.”
Jeepman89
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Re: The Babysitter

Post by Jeepman89 »

I remember the video. I hope you continue soon. Can't wait to see what she makes Jimmy do?
drtickle
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Re: The Babysitter

Post by drtickle »

Very nice b eginning, can't wait to find out how this works out. Just a shame Sara did not ask for an explanation of tickle torture...but hey, that's just me. Please keep the story coming.
drtickle :mrgreen:
VansFic
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Re: The Babysitter

Post by VansFic »

Thank you for reading, commenting and encouragement on the first part. The first few parts will be a bit predetermined but later on I might take suggestions about what direction things continue in. Here is the next part, a little but shorter than the first, and the third will come tomorrow.

Part 2
~~~~~~~~~~~~~~~~~~~

Jimmy led the way from the kitchen to the game closet, Sara chasing after him. Though he didn’t know exactly which room it was having only been given a quick tour of the house and soon passed the den where the Abbotts kept their stockpile of board games. He noticed Sara had stopped following him, prompting Jimmy to realize he should have just let the girl lead the way in her own house. Walking into the room decorated with a mix of art and family photos, he followed Sara into a small walk-in closet filled floor to ceiling with board and card games of all sorts.

The space in the closet was tight, only about six inches separated the two. Jimmy handed over the bowl of popcorn to Sara to hold while he reached up to pull on the thin metal chain to turn on the overhead light. Jimmy looked down to see the girl munching away on popcorn and staring at him, still accusing him of not knowing the answer to her previous inquiry. He sighed and started looking around trying to judge what game would be best to move on from the awkward encounter.

“Pictionary,” he offered unenthused.

“No,” Sara said in a quiet voice.

“Taboo.”

“No,” Sara said, she pulled off the swim goggles from her head.

“Jenga,” Jimmy tried again.

Setting the goggles on a shelf next to her she looked up at him like he was joking, “no.”

“Monopoly,” he said. He cared less about what they played and just wanted her to pick something at this point.

“No,” was the only answer he got.

“Boggle.”

This time Sara looked up to where he had pointed and almost seemed to consider it for a moment before answering once again, “no.”

“Scattergories,” he mentioned to the box he had seen walking in that was now behind him.

“Mmmm no.” Jimmy was starting to think her refusal to agree on a game was on purpose now.

“Trivial Pursuit,” the boy offered, reaching up towards the game. He had to lean forward slightly to reach it and Sara could feel his dark hoodie brush against her as she looked to the side and once again gave her familiar, “no.”

Jimmy tried reaching higher to see what other options they had. “Yahtzee,” he said, moving the boxes around to see the various names of the games available to them.

Sara leaned town to pick up some popcorn she had spilled between their feet from her snacking. “No,” it seemed was the only word the girl was able to say that the moment, rejecting his latest offer.

Still kneeling down in front of him, Sara looked up as Jimmy offered Clue as the next option of potential games. His tan khakis were baggy on the teenager and she could see how they sagged slightly on his hips. The way that Jimmy had stretched to reach the boxes on the top shelf allowed Sara to see the light blue band of his underwear as well as his stomach. There was a thin line of hair stretching from his belly button downward, disappearing into his underwear. She took a moment to take in the details of her babysitter's body, his stomach was flat with just the start of development of his abs, she could see the contours of his waist and he obviously did not sunbathe shirtless based on the paleness of his skin.

Sara looked up smiling towards the oblivious boy, “you got hair on your belly button.”

The pronouncement startled Jimmy and he quickly grabbed at the hem of his shirt to try and pull it down to cover his exposed stomach. His mouth gaped for a moment as he tried to collect his thoughts. This little girl was openly examining his features and he was feeling very embarrassed. Twice now she had managed to expose him, first with his lack of experience and now literal exposure of his body. He was supposed to be the one in charge here but it wasn’t feeling much like it.

“Okay we’re playing Trivial Pursuit,” Jimmy tried recovering, “and that’s final.”

Sara stood up and their faces were just inches from each other. She could see how his face had started blushing. “Fine but I’ll beat you,” she stated matter-of-factly.

“No you won’t,” came the weak retort.

“Yes I will,” Sara said in a tone to try to imitate his deeper voice.

“No you won’t,” Jimmy said again before leading the way out of the closet to try to cut off any further argument.

He should have known Sara would never let him have the last word. She reached up and pulled on the chain to turn off the overhead light and followed him into the living room, her tone sounding more like someone annoyed of arguing when she obviously knew the outcome before it had even happened, “yes, I will.”
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Executionus
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Re: The Babysitter

Post by Executionus »

Fun intro so far. I get the impression that this girl is going to have him wrapped around her little finger in like an hour tops.
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Re: The Babysitter

Post by Lola »

Nice! Can't wait for more :D
VansFic
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Re: The Babysitter

Post by VansFic »

Hello, time for the next installment. No double feature for today, though Part 4 will go up tomorrow. Enjoy!

Part 3
~~~~~~~~~~~~~~~~~~~~~

Laying on the floor, the board game opened and its parts splayed out between the pair, everything had been going just as Sara predicted. The girl adjusted the shoulder strap of her overalls momentarily as she waited for Jimmy to “test” her with another question. She was surprised at how easily this was going for her while the boy struggled. He didn’t get them all wrong, but far more than she had. And wasn’t he supposed to be the smarter, more mature babysitter here?

“What is the capital of California?” Jimmy asked.

Smiling, Sara quickly answered, “Sacramento. Your turn.”

She took the card for getting the answer right and passed the die over to Jimmy who only had the look of someone who resigned to his fate in this game already. The roll came up a 4 and Jimmy tapped his piece along the spaces before looking up to Sara waiting for his question.

The girl had been considering her options with this game. She could just win and hold it over him, but after his failed attempt to explain a blowjob to her and then the obvious signs of puberty she saw in the closet, Sara considered this an opportunity to perhaps test more than just his knowledge of the standard Trivial Pursuit questions. It came to her almost instantly what she wanted to ask instead of what was printed on the text of the card. She had just started her Sex Ed course in school and thought this might give her the opportunity for her babysitter to unwittingly expand on what she was learning there.

“What is pre-ejaculation?”

Shit, Jimmy thought, another question he didn’t know the answer to, and there Sara sat with an expectant look upon her face. “Umm,” he started with a sigh, “I dunno, something Edison invented?” He knew it wasn’t exactly an answer but he hoped if he was close maybe she’d just give it to him considering how badly he was losing at this point.

“No. You lose,” Sara said with a shake of her head and roll of her eyes. How naïve was this boy? She set the card in the discard pile as Jimmy just looked slightly embarrassed to get another question wrong.

“My turn,” she said, taking the die and rolling it across the board and moving her piece the corresponding amount of spaces.

Jimmy smiled thinking he finally pulled a challenging question for the little twerp. “What famous painting was hanging in the bathroom of…”

“The Mona Lisa,” she cut him off before the question was even finished. Her whole posture, even in this lying down position, showed the confidence of her answer as she held out her hand expectantly for the card.

“You’ve memorized the cards haven’t you?” he replied in an accusing tone, the smile gone from his face.

Her fingers waved in his face, “give me the card.” The pair stared at each other for a few seconds before Jimmy finally relented.

Again Jimmy rolled and slid his piece across the cardboard surface and Sara reached for his question. She held it close to her face as she read the question but stopped herself from reading it aloud. Instead she peered over it towards the teen, trying to hide a smile that was growing on her face.

Jimmy stared back at her waiting, his blue eyes focused and determined. This time he would get the damn question right, no matter what it was. He nodded at her to get on and ask him.

A final pause, Sara looked at the card again, then spoke, “what is masturbation?”

Jimmy shook his head and jumped up to sit kneeling with his legs under him and held out his hands in protest. “You’re making these questions up Sara.”

“It’s science Jimmy, science,” the girl argued back just as forcefully, tapping on the space his piece had landed on.

Shaking his head in resignation, “okay then.” He paused for a moment to collect his thoughts and took a deep breath. “That’s when someone…” Another pause and he sighed, “like, plays with themself.” The boy absently pulled at his ear as he tried to think of how to say the next word and just spat out, “sexually.”

“Do you do it?” Sara raised herself to her knees excitedly that she finally got him to give her a straight answer.

“None of your business,” he tried to answer seriously, “now give me the card.”

Sara held up the card over her shoulder as a sign of defiance, “I’ll give you the card after you answer me.”

“I won’t answer you,” he said, shaking his head and holding out his hand for the card in his best stern babysitter imitation.

“Jimmy it’s not like I’ll tell anyone,” Sara begged.

“Give me that card,” Jimmy said again.

“No, not until you answer.”

“No,” the teen said sternly.

“Do you want the card or don’t you?” Sara asked, holding it out teasingly.

Jimmy tried to snatch it from her grasp but her hand pulled back too fast. He sighed again and threw up his hands in frustration. “Okay! Fine! Yes, yes, yes I do. Everybody does. Okay?”

“Gross pervert!” Sara exclaimed, throwing the card behind her.

Jimmy scrambled after it, picking it up from the floor and leaning against the low shelving behind Sara while he read the card. “You little shit,” he said looking up from the card in disbelief.

“Well, I didn’t think you’d know what direction the Leaning Tower of Pisa is actually leaning in,” the girl said without even looking back at him, knowing that her deception was uncovered.

She spun around to look up at Jimmy, “do you do it everyday?”

Jimmy was still stunned that this 12 year old girl had gotten him to admit to jerking himself off. He tried putting on a serious face and folded his hands over the card, “I don’t do it at all,” he leaned forward a little, “I was just lying to you. I don’t need to do it. I have a girlfriend.”

“Really?”

“Yes. And she’s beautiful and perfect and I was supposed to meet her tonight, and instead of that I’m stuck here with you, you idiot.” His anger was starting to bubble to the surface. His friends had doubted him about his, admittedly fictitious, girlfriend. This girl had totally derailed the his plan of a nice easy gig to earn some extra money and was making a fool of him. Jimmy felt he had to do something to reassert a mature demeanor over this twerp.

“What’s her name?” Sara asked calmly.

“None of your business,” now Jimmy was just refusing out of spite.

“Is it Wendy?” Sara asked in a sing-song voice.

Jimmy just stared agape at her. Sara’s impatience at his reluctance to answer her overwhelmed her, “come on, tell me.”

Looking off to the side to try and collect his thoughts for a moment he turned back to the girl he was supposed to be babysitting but so far felt more like she’d been interrogating him all night. “Okay, if I tell you, do you promise not to ask any more questions?”

“Yes,” Sara replied exasperated.

Jimmy nodded his head slightly urging her to be more serious with her promise. “Cross my heart, hope to die,” she finally answered at his urging.

“Wendy,” was all Jimmy said in response.

“Do you fuck her?” Sara immediately asked, disregarding the promise she just made. Jimmy’s mouth hung open. He had never heard a girl actual use that word before, at least not when referring to the actual sex act. Where did this girl learn these things? And how did he end up in this situation? The boy just exhaled loudly and stood up walking away from the conversation.

“What?” Sara asked, confused why he couldn’t answer such a simple question, before chasing after him.
Jeepman89
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Re: The Babysitter

Post by Jeepman89 »

I hope you get to the good stuff soon.
drtickle
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Re: The Babysitter

Post by drtickle »

Jeepman89 wrote: Thu Jun 03, 2021 8:14 pm I remember the video. I hope you continue soon. Can't wait to see what she makes Jimmy do?
Hey, would you mind telling me, which film it is based on?
drtickle :mrgreen:
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Re: The Babysitter

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