Adventures in Babysitting

Disclaimer: This is a work of fiction! To my knowledge none of the events depicted are even remotely true.

Notes: This story is inspired by / based on / a complete rip-off of the comic The Nanny by Altuna (it’s out there, google it if you like). Feedback would, as always, be much appreciated.

“Okay, you can come on in Miss” the lady leans out the office and says.

“Thanks!” the cute young redhead smiles and picks up her bag.

“Please take a seat,” the lady offers taking a seat behind the desk herself, “I have had time to look over your information since our last meeting…” she smiles, “… and we would be delighted if you would make yourself available to us. Now this is how it we do things, we would contact you with potential jobs and you can choose from those, sounds good?”

“Sounds good” Jane Levy replies, “When can I start?” she ask with a smile.

“Great! Welcome to Sitter-for-Hire then!” she say, a wide smile on her face, “Here’s your log-on for our website, it’s updated with jobs regularly and I’ve got your phone number so in case of emergency you might hear from me…” she say, continuing when she sees the questioning look on Jane’s face at the mention of emergency, “If we need anybody urgently… as we do today! I was just about to desperately call around for a job tonight… the girl had to pull out, unfortunately… but thank you for coming onboard and… I’ll see you around, I guess” she says as she turns her focus to some of her papers, looking for potential takers for the job.

“Sorry to hear that…” Jane say as she puts the card which she is handed into her purse, “… where is it?”

“Huh?” she replies not taking her eyes off the files in front of her.

“Tonight… I’ve got nothing planned really…” Jane explains.

“Oh…” she lifts her head, turning her full attention back to the young redhead again, “you would do that?” a smile full of hope and relief on her face.

“Yeah, sure…!” the young girl shrugs her shoulders.

“Great, it is downtown… Mr. and Mrs. Bennett’s date-night…” she explains.

“I can do that” Jane smiles.

Sighing with relief the lady smiles, “I love you!” she grin and scribbles down some info on a piece of paper, “Here, you need to be there at eight at the latest, okay?” she hand Jane the note.

“Sure, I’ll be there!” she replies and picks up her purse.

“Again, thank you so much!” the woman thank her again as she leaves the office.

As she walk out of the offices of the babysitter agency Jane Levy feels pretty good about herself. Having dropped out of school to pursue an acting career she is now in New York and wanting to have a little extra money on the side she had gotten in touch with this agency, thinking that babysitting a couple of times would be the way to make some money and maybe distract herself from the acting school.

It would be a few years before she broke into the spotlight with the role of Tessa on Suburgatory so for now she was just a young aspiring actress taking a part-time job on the side and feeling happy about getting the job and also having something to do tonight make her smile as she walks down the street.


Loosening her coat as she pushed the button for the fifth floor Jane take a look on the clock, confirming that she is arriving with time to spare as it is only just about half past seven. Wearing a dark skirt, a very conservative knee length one, and a blouse underneath the coat she pulls out the note to check the address, for the fourth or fifth time since leaving her apartment, reading aloud “Fifth floor apartment… 8… right…” she tell herself, interpreting the agency lady’s scribble.

The ping echoes through the elevator as it reaches its destination and the doors opens. Stepping out she looks around before moving down the corridor in the direction of the apartment. Looking at each door as she slowly makes her way further down the hallway until she reaches number eight.

“This must be it…” she mumbles, checking the note a last time before ringing the bell.

It doesn’t take long before she can hear the chain being taken off and the door opens, a middle-aged man in a blue silk shirt greeting her, the shirt not buttoned all the way leaving a part of his well-sculpted chest visible. Smiling he looks her up and down quickly, muttering “Nice!” barely audible.

“Hi…. I’m Jane, you called the agency?” she smiles, giving him the once over too.

“I did… very, very nice!” he smile, leaning against the doorframe while eying the young girl, “Please, come on in!” he seem to snap himself back to reality and steps back to let her enter.

“Thanks…” she enters his apartment, feeling more than a little attracted to the man, ‘If I wasn’t here to look after his kids…’ she think as she walks into his living room while he closes the door, locking it again.

“Man, they weren’t lying when they told me ’bout you!” he grins as he joins her.

“Oh, they…?” she turns to him, “What did they say?” she asks.

“Just that you were a cute young thing and very enthusiastic about the job” he say as he steps in front of her, real close, and trail his hand from her shoulder down her arm and takes her purse when he reach her hands.

“Yeah, I think it’s a be good way to spend you free nights… and the money is always good!” she say, letting go of her purse which she had held onto with both hands, feeling that he is standing a little close but not really minding as she finds him very attractive.

Staring into her eyes for short while he grin and turns away, taking her purse to the couch. As he does Jane has time to take a deep breath telling herself not to act like this around this man, ‘You’re here to babysit for god’s sake!’ she think then she wonders why there’s only him here, ‘His wife and kid must be out…’ she reasons as she takes another look around the apartment.

“So… umh… when do I start?” she ask, “I know I’m a bit early… eight and all…” she stumble over her words as he turns back towards her, an intense look in his eyes as he steps up close to her again, her heart rate increasing as this hunk of a man looks at her like this.

“Eager, little one?” he say as stands close to her again, “You’re right… no time to waste…” he softly whispers, pushing a wisp of her red hair behind her left ear, “… time’s money, huh?” he hiss into her ear as he leans close.

“What are you…” she mumble as he touches her hair and she feel her heart racing as he whispers into her ear, his breath on her neck. Blushing from a mix of confusion and excitement from the forbidden nature of the man’s behavior towards her she gasps and tells herself to get away from him, to stop him from acting like this, but she doesn’t, too stunned to move.

“Yeah, come ‘ere girl!” he says, wrapping an arm around her back and pulling her body into his making her yelp in chock.

“But… wha… please…” she begs as he kiss her neck holding her close, her arms trapped between their bodies as she attempted to keep some distance are now making a futile attempt to push him away.

“Hmm… spirited?” he grunt, “I like that!” he laughs and moves one hand onto her ass, groping her as he kisses and licks down her neck.

“Please, why are you doing this?” Jane whimpers, eyes shut as she feels his mouth on her neck and his hands roaming her back and ass pulling her close to him.

Kissing her on the side of her lips he hushes her, whispering “It’s alright, you don’t have to put on an act for me, babe” before taking her head in his hands and covering her lips with his, forcing his tongue into her mouth when she opens it, gasping.

“Mmmhmm!” her complaints are muffled as he kisses her hard, pulling at her shirt with one hand while backing them closer to the couch. Getting her shirt over her breast he squeeze them trough the bra before reaching behind her and unclasping it, pushing it up and over her breast too. Jane’s resistance begins to fade, her body’s flush with a mixture of fright, anger and (she’s embarrassed to admit) desire. After kneading her naked breast, pinching and pulling on the nips, he grabs the hem of her skirt inching it upwards. When the couch makes contact with the back of her legs he pulls it all the way up pushing her back onto the couch with the skirt bunched around her waist.

“So young… and sexy…” he mumbles, licking his lips as he stands over her, “We’re gonna have fun, little one!” he winks before tossing his shirt away and getting onto the couch along her. Resting his knee on the cushion he puts on hand on the back of her head, twisting his fingers in her red hair as he pulls her up a little mashing her lips with his, and his other hand moves between her legs rubbing her through her panties.

Gasping, nearly hyperventilating, as he pushes her onto the couch she can’t help herself biting her lower lips and stare as he remove his shirt and when he moments later is on her again, forcing his tongue into her mouth and touching her sex she feels her body take over and she starts responding to the kiss and spreads her legs a little, allowing him better access. ‘He looks good… and he wouldn’t do this if we could be caught…’ she reasons with herself, ‘… just make-out for a while, before the wife and kid comes…’ she thinks as he ends the kiss and sucks one of her nipples into his mouth, sucking and chewing it before moving to the other one.

As she starts to soak through the front of the panties he pulls away from her and grabs hold of either side of them, peeling them off, they cling to her wet pussy as he tugs them down. Tossing them across the room he unbuckles and removes his pants revealing his steadily hardening cock, average in length but pretty thick.

“Come here!” he growl and pulls into a seating position, pealing the shirt over her head and off, the bra going the same way. Her eyes are transfixed on his cock, flapping in front of her she feels her body tingling with excitement as she sits naked on the couch, the skirt around her waist, and watch the shirtless man and his fat cock.

“Please, we shouldn’t…” she will herself to stammer, common sense telling her to ignore what she’s feeling, but he just wrap a hand in her red locks and pull her head into his crotch, his cock pushing against her lips, her yelp of “No!” is muffled as he shove his cock into her mouth.

At first she tries to resist him, a last futile attempt to stop him and tell herself not to enjoy this, but he just holds her in place and shoves his cock in and out of her mouth. With her eyes shut she weakly pushes at his thighs and makes muffled complaints but soon she closes her lips around the intruder and applies the tiniest bit of suction, her eyes shooting wide open as she stops this again, shocked at how she subconsciously reacted. Her struggles from then on was more about keeping her own desires in check and she embarrassingly concedes defeat a couple more times, swirling her tongue under and on the head of the cock, closing her mouth tight around it and leaning her head forward to get him a little deeper, as he continues to use her mouth, now completely erect.

“Yeah, get it!” he moan, feeling her starting to respond, and as she concedes defeat he stops thrusting into her mouth, letting her work his cock over while he kicks his pants off. Leaning down as she blows him, her hands no longer pushing at his legs but one holding his hip and the other gripping around the bottom of his cock, steadying it, he grope her breast shortly before reaching between her legs, rubbing her exposed sex teasingly, feeling her wetness, before pushing a finger into her.

“Mmmhmm!” Jane moans around the cock, looking at him with rolling eyes and smiling at him, “That feels so good!” she gasp as pulls her mouth off him, just holding onto his fat dick while he plays with her pussy, pushing another finger into her while circling his thumb over her clit.

“Get up” he removes his fingers, wiping off the wetness on her thigh, and grabbing her under her arms lifting her off the seat. With a surprised yelp she’s on her feet watching curiously, with a smile on her flush face, as he gets onto the couch and pulls her with him, eliciting another playful yelp from the young girl.

“Oh…” she giggle as he lifts her on top of him, her legs around his head and pushing her head down towards his cock, still slick with her saliva, “Wha… ooohh!” she groan as he pulls her folds apart, a hand on each cheek of her cute little ass, and runs his tongue along her pussy, “Like that, huh?” she gasp and grabs his cock knowing what he expects. Swallowing his cock she moans around it as his tongue explores her wet hole and for every wave of pleasure he sends through her body she increase her efforts to make him feel equally as good.

Slurping around his cock the best she can, which is made more difficult by the pleasure he’s giving her, his tongue probing deep inside of her or teasing her clit as his fingers saw in and out of her, she twist and turn on top of him soon feeling and orgasm wash over her, moaning as she rest her head on his thigh, just clutching his hard cock.

“Oh… mmm… god, that…” she gasps.

“Giddy-up!” he grunt delivering a stinging slap to her ass and pushing her down his body, “Time for you to earn your pay…” he continues under his breath.

“Ouch! What?” Jane mumbles, slightly dazed from the orgasm, as he guides her into position, straddling his legs her ass towards him.

Grabbing hold of his cock and her hip he pulls her into his lap, guiding his cock between the folds of her moist pussy. They both moan as he penetrates her, pulling her all the way down till their bodies meet, he enjoy the feeling of her young thigh body gripping his cock tightly, running his hand over her ass he grins at the red mark from where he slapped her and slapping her opposite cheek equally hard he begins thrusting into her while moving her body up and down, signaling for her to ride him.

Her small hands grasping his legs just above his knees and one of her legs resting on the floor next to the couch she lifts off the cock till the head threatens to plop out before dropping back down. Repeating this she quickly gathers pace, the sound of flesh slapping together and their combined moans fills the room.

“Oh god… fuck me, fuck me…” she moans.

“Yeah, get it babe!” he grunts his hands on her hips, pulling her down a little harder each time.

“Yes!” she gasps her heart racing as she rides him hard, “Sooo good!” she mumbles through a moan.

A thin layer of sweat begins to coat her body, particularly her forehead and the valley between her breasts, which bounce along with her movement. Feeling another orgasm approaching her legs tremble and she loses her grip on his legs falling onto them, her breast squashed against his legs as she bounce her hip up and down until she buries her open mouth on his shin, muffling a scream as she cums hard.

“Hmmmm…. Ooohhh… fuck… aaahhhhhh!” her screams fill the room.

Chuckling he watch her ass shudder as the orgasm wash over her, feeling her pussy clamp down hard on him and soaking it in her juices. As she calms down again he rubs her ass and twitch his cock inside of her making her tremble a little more. With a grin on his face he then pushes her forward so his cock, soaking wet and still hard as a rock, plops out and onto his belly.

“Uhh…” she moans as he slips from beneath her and effortlessly flips her onto her back, her eyes half-closed she doesn’t seem to take much notice to his actions in her current state.

“Fucking nice… so young…” he mumbles as he moves his hands over her naked body stroking her breast before taking hold of her skirt and peels it off. Spreading her legs he moves between them, sitting on his knees on the couch between her legs, her right feet on top of the back of the couch and her left hanging off the edge.

“Mmm…” she moans as he pushes his fat cock back into her, her eyes opening and she stares openmouthed at him, desire burning in her eyes, “Please…” she moan, “… fuck me!”

He grins, takes hold of her waist and does just that, thrusting hard into her he lift her ass off the couch a little bit and with his force he drives her shoulders and head into the cushions. Fucking her hard and fast he shows no regard for the young girl, only interested in his own pleasure.

“Aaahhh… aahhh…” Jane gasp each time he enters her, feeling her body tingling from the hard fuck the she is receiving. Rather inexperienced getting pounded by a older man, who’s sweating and groaning while throwing an animalistic fuck her way, is an incredible turn-on for her.

“Fuck!” he growl as he with a particularly hard trust, having slacked his hold of her, pushes her off the edge of the couch, she squeals before hitting the ground with a slight thud. Not a fall that would actually hurt her but it stunned her shortly, during which he got off the couch too and got back between her legs again.

“Oh, be careful with me!” she giggle as he drive his cock back inside of her, her back resting against the couch he takes hold of her thighs and starts pistoning into her again.

Fucking her hard he soon lets go of her legs and places his hands on couch, either side of her, and leans over her as he thrust into her, both of them now covered in sweat and huffing and puffing. Jane tangles her legs with his and let her hand explore his upper body, running her small hand over his chest and back. She pushes her red hair behind her ear and look at him, his eyes closed and face twisted in pleasure, biting her lips she leans her forward, kissing his chest as she feels yet another orgasm approaching.

“Aaaaaaiiiiiiii!” she screams as it hit, arching her back as her entire body quivers her legs unwrapping from his as she twist and turn. The arching of her back and the movement of her body means his cock slips out of her dripping pussy and he leans back, watching with smirk on his face as the young girls body convulses in pleasure.

Flipping her over, he pushes her onto the couch and guides his cock back into her pussy. He takes a firm hold of her hips and resumes fucking her, determined to get off. Jane sighs and rests her head on the couch while he fucks her from behind, enjoying the waves of pleasure he sends through her satisfied body. His thrusts quickly becomes more erratic and with a grunt he yanks his cock out of her and strokes it a few times before unloading onto her ass, some hitting her back and drips down the side.

Exhausted he leans back and after catching his breath he stumbles onto his unsteady legs and laughs a little as he walks to his liquor cabinet, “The bathroom is the first door to the right…” he tell her.

“Umm, right…” she replies, softly, as she suddenly feels very conscious about what she has just done.

Getting onto her feet she makes her way to the bathroom and cleans his cum off her body. Freshening up a little, so that she at least didn’t look and smell like she’d just been thrown the fuck of her young life, she looks at herself in the mirror. “What are you during?” she whispers, “You’re here to look after his kid… where is that kid?” she ask herself, but then she quickly turns away from the mirror worrying that the kid, ‘…and his wife!’ her mind screams, would arrive while she was naked in the bathroom and hurries back to the living room.

“Thanks babe!” she is greeted by him as she steps out of the bathroom, he wraps his arms around her and kisses her on her forehead, “I left your money on the table… and a nice tip!” he brush her cheek and winks at her, before entering the bathroom and closing the door.

Stunned, at first by his presence when she opened the door and then by what he says, she doesn’t reply before he is gone. “What?” she mumble and then hurries to get her clothes finding the bra, skirt and shirt easily, but having trouble finding her thong she almost consider leaving it before she sees it hanging on a shelf on the other side of the room. ‘Why is he paying me now?’ she thinks, ‘… he doesn’t think… that I’m… a… who… prostitute?’ Her eyes opening wide she grabs her coat and heads for the door, stopping and scooping the money into her purse before leaving.

“Oh god…” she says, her heart racing as she walks away from the apartment, stopping as she round a corner and leans against the wall. “Why did I take the money?” she mumbles as she looks into her purse, considering counting them but deciding against it. Instead she takes out the note with the address again, checking it again.

‘God, maybe it isn’t an 8 but a 1 and 3…’ she thinks, pinching her eyes together.

Stepping a little further down the hall she nervously knocks on the door to apartment 13, taking a deep breath as she waits.

“Yes?” the door swings open, a well-dressed woman appearing, she seems stressed out.

“Uhm… hi, you called for a babysitter?” Jane asks.

“Thank god!” the woman sighs, “Yes we sure did, you’re late young lady!” she then scolds her and moves back inside the apartment.

“Yeah, I known… had a little trouble… umm… finding it…” Jane replies and follows her inside.

“Honey, the nanny is here!” the lady yells, a man replying “Finally!” somewhere inside.

Like a whirlwind the couple is out of the door, giving Jane the necessary instructions and grabbing their coats.

“Jeez…” Jane sighs as she’s left alone with the kid.


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