The Sitter
The babysitterâs name is Jessica. Sheâs nineteen, a sophomore at the community college, studying something you can never remember.
She has honey-blonde hair she usually wears in a ponytail, but tonight itâs down, brushing her shoulders, and sheâs wearing a faded gray sweatshirt.
And those leggings that are somehow both modest and devastating. The kind that cling to every curve from waist to ankle, leaving nothing to the imagination except the exact texture of the skin underneath. Youâve been imagining that texture for the last forty-seven minutes.
Your call ended an hour agoâa tedious, interminable Zoom with the regional managers that required your full attention, which is why youâd booked Jessica in the first place.
The boys were still up then, needing dinner, needing baths, needing the kind of focus you couldnât give while faking engagement with quarterly projections.
Now, the kids are asleep. Have been for an hour. Jessica is in the kitchen, cleaning up after the snack she made for the boys.
Youâre in the living room, the report you promised yourself youâd start sits open and unread on your screen, a gray wall of text youâve been skimming without comprehension, because all your focus has rerouted itself to the kitchen, to the sound of her, to the shape of her in those leggings.
Youâve been watching the arch of her back as she leans over the counter, the shift of her hips as she reaches for a towel, the way the leggings tighten across her ass when she bends to put a bowl in the dishwasher.
You know you shouldnât. Youâre thirty-nine. Divorced. You have a mortgage, a minivan, a membership at Costco.
But youâve been watching her since your meeting ended, and the watching has become a low, persistent hum in your blood, a frequency you canât tune out.
You shift on the couch. Your khakis are getting tight. You adjust the laptop on your knees, trying to create some cover, but itâs useless. Youâre hard. Youâve been half-hard since she took off her shoes and padded around in socks, her feet small and pale against the hardwood.
Itâs pathetic. You know itâs pathetic. A man your age, staring at a woman half his age, in his own house while his children sleep upstairs.
But knowing itâs pathetic doesnât make the wanting stop. It just layers shame on top of want, and the combination is somehow more potent than either alone.
You look up from your screen just as she turns from the sink, drying her hands on a dish towel.
She catches your eyes. You snap your gaze back to your laptop, your heart hammering. Too late. You saw her see you.
The moment hangs in the airâthe hum of the refrigerator, the distant tick of the hallway clock, the weight of her attention now focused on you.
You hear her footsteps. Soft, sock-muffled, coming into the living room. You keep your eyes on the screen, on a paragraph you havenât absorbed a word of.
She stops beside the couch. You can smell herâlaundry detergent, the faint sweet scent of the kidsâ fruit snacks, something underneath that is just her, hot and clean.
You force yourself to look up. Sheâs standing there, the dish towel draped over her shoulder, her head tilted slightly. Her eyes are a clear, direct blue.
Sheâs not smiling, but sheâs not frowning either. She looks⌠curious. Like sheâs found an interesting bug and is deciding what to do with it.
âYes, Jessica? Everything okay?â
âEverythingâs fine. The boys are out cold. I checked on them twice.â
She pauses. Her eyes drift down, just for a fraction of a second, to your lap, where the shape under your khakis is unmistakable.
Then they come back to your face. No blush. No look of disgust. Just that calm, assessing curiosity. âYouâve been staring at me all night.â
Itâs not a question. Itâs a statement. Delivered in the same tone she might use to say the dishwasher is finished. Matter-of-fact. Unembarrassed.
Your mouth goes dry. âIâI havenât been staring. Iâve been working.â
She nods slowly, as if considering this. âYouâve been looking over the top of your laptop every thirty seconds since seven-fifteen. Your eyes follow me when I walk across the room. They drop to my butt when I bend over. They linger on my chest when Iâm facing you.â She says it all evenly, clinically. âThatâs staring, sweetie.â
The word lands on you like a physical touchâa warm, dismissive pat on the head. Sweetie. Not your name. Not sir. Sweetie. Your face, already hot with shame, burns hotter.
Itâs the kind of thing youâd call a child, or a dog. It shrinks you in your own skin, collapses the thirty-nine years between you into nothing.
And yet, beneath the humiliation, another part of youâthe part thatâs been hard since she walked inâflutters in response. Itâs permission of a kind. An intimacy. Sheâs named you, and the name makes you hers.
âIâm sorry,â you mumble, looking down at your hands. âI didnât mean to make you uncomfortable.â
âYou havenât made me uncomfortable.â She says it so simply you have to look up again. Sheâs still watching you, that same thoughtful expression on her face. âItâs just a thing thatâs happening. Youâre staring. Your penis is hard. Your face is red. These are facts.â
She takes a step closer. You shrink back instinctively, but thereâs nowhere to go. The couch is against the wall.
âThe question,â she says, her voice dropping to a conversational murmur, âis what weâre going to do about it.â
We. She said we. As if this is a shared problem, a project for the two of you.
Not what Iâm going to do about you, but what weâre going to do about it. The word settles in the air between you, intimate and terrifying.
âI⌠Iâll go to my room,â you stammer. âIâll leave you alone. Iâm sorry.â
She shakes her head, a small, almost imperceptible movement.
âThat doesnât solve the problem, sweetie. The problem isnât that youâre here. The problem is that youâre like this.â
Her gesture is vague, encompassing your whole embarrassed, aroused body.
âIf you go to your room, youâll just lie in bed and think about me. Youâll probably play with yourself. And then youâll feel guilty, and youâll avoid me, and itâll be weird when I come over next time. That doesnât help either of us.â
Sheâs right. Of course sheâs right. Thatâs exactly what would happen. The accuracy of her prediction is like a key turning in a lock inside you. She sees you. She knows what you are.
âSo,â she continues, folding her arms loosely across her chest. The movement pushes her breasts together, and you canât help but look. She notices you looking. She doesnât comment. She just notes it, the way a nurse notes a symptom.
âWe need to handle this. Like adults. Well, Iâm an adult. Youâre⌠youâre having a hard time being one right now, arenât you?â
Itâs not a taunt. Itâs a diagnosis. Delivered with a gentle, almost sympathetic tone.
You nod, miserably. You canât speak.
âThat's okay,â she says. âLots of men have a hard time with this. My boyfriendâs dad is the same way. Heâs always looking at me when Iâm over there. His wife works nights.â She says this as if sharing a mildly interesting piece of gossip. âI had to have a talk with him, too.â
A talk. The phrase holds so much promise, so much threat. You wonder what that talk involved. Your imagination supplies images that make your cock twitch against your zipper.
Jessica sighs, a soft, put-upon sound. âThe thing is, sweetie, youâre not a bad guy. Youâre just⌠needy. And when needy men donât get what they need, they get clumsy. They stare. They make things awkward. Itâs not really your fault. Your penis just gets ahead of your brain.â She tilts her head again. âYou need someone to take the wheel for a little bit. Donât you?â
You nod again. Itâs the only response youâre capable of. Yes. God, yes. Youâve needed someone to take the wheel for twenty years.
âYa, I thought so.â She smiles for the first time. Itâs a warm, pretty smile, the kind that would light up a room if it werenât currently lighting up your shame.
âYour little guy has overwhelmed you. That's why Iâll manage him. And you. So you just do exactly what I tell you. Okay?â
âOkay,â you whisper.
âOkay.â She leans down and reaches out and pats your knee. The touch is brief, impersonal, but it sends a jolt through you.
âGood. Now what you need is to learn how to behave. And to empty out all thisâŚâ She gestures at your crotch. ââŚthis nervous energy. So you can be a good dad and a good man and not a creepy guy staring at the babysitter.â
Every word is a nail hammered into the coffin of your dignity. And every nail feels like a release.
âNow,â she says, her voice dropping back into that calm, instructional tone. âYou stared at my body without permission. Thatâs rude. When someone is rude, there are consequences. You understand that, right? You teach your boys that.â
âYes.â
âSo youâre going to get a spanking. A little one. Just enough to remind you to keep your eyes to yourself. That's how men like you learn.â
She says it the way she might say youâre going to wash the dishes. No drama. No kink. Just a fact. A consequence.
Your heart is pounding so hard you can feel it in your throat. A spanking. From a nineteen-year-old girl. The absurdity of it is almost as dizzying as the arousal.
âLet's get started,â she says, turning and walking toward the armchair in the cornerâthe big, plush one. She sits down, primly, smoothing her leggings over her thighs.
âCome here. Pants and underwear down to your ankles.â
Your hands are trembling as you fumble with your belt, your button, your zipper. You push your khakis and boxer briefs down to your ankles. You stand before her, naked from the waist down, your cock standing stiff and flushed against your belly. Youâve never felt more exposed, more utterly seen.
Jessicaâs eyes drop to your erection. She studies it for a moment, her head tilted.
âHeâs very eager, isnât he?â she observes. âEven now, when youâre about to be corrected. He doesnât know any better.â
She looks up at your face, her gaze steady. âBut you should, sweetie. He may overwhelm you but youâre the one who let him. Thatâs why you need training.â
She pats her thigh. âOver my lap. Carefully. I donât want you poking me with that thing.â
The humiliation is exquisite. You maneuver yourself over her knees, your upper body resting on the cushion of the armchair, your legs dangling.
Your cock is trapped between your belly and her thigh, a hot, insistent pressure. Her leggings are soft against your skin. She smells like fabric softener and girl.
Her hand rests on the small of your back, warm and steady. âThis is going to sting a little,â she says conversationally. âBut itâs for your own good. Count for me, okay? Count each one. If you lose count, we start over.â
âYes, Jessica.â
The first spank lands. Itâs not as hard as you expected, but itâs sharp, crisp. The sound is loud in the quiet room.
âOne,â you say, your voice shaky.
The second. A little harder. âTwo.â
She finds a rhythm. Not too fast, not too slow. Each spank lands on a different part of your buttocks, spreading the sting. Youâre not in pain, not really.
Itâs more like a intense, focused warmth, a bright attention centered on your most shameful place.
And with each smack, your cock throbs against her leg. Youâre leaking precum, you can feel it, a wet spot forming on her leggings.
âYouâre getting wet on me, sweetie,â she notes, her hand pausing. âYour little guy is leaking. Even while youâre being corrected. He likes this, doesn't he?â
âYes,â you gasp.
âWeâll have to do something about that later. Keep counting.â
âThree⌠four⌠fiveâŚâ
By ten, your ass is warm and tingling, and youâre so hard itâs almost painful. She stops. Her hand rubs your back in slow circles.
âThere. All done. That wasnât so bad, was it?â
âNo.â
âGood. You took your punishment like a good boy.â She helps you ease off her lap. You stand before her again, your erection bobbing, your ass throbbing. You feel dazed, pliant, utterly hers.
âNow,â she says, looking up at you from the chair. Her voice is calm, instructional.
âWe have the other problem. The leaking problem. Your little guy is still all worked up. Heâs been like this all night, hasnât he? Practicing in your head. Getting ready.â
She leans back slightly, her gaze dropping to your erection. âAll that pent-up energy needs to go somewhere. But weâre not going to make a mess. And weâre not going to let you sneak off and do it alone like a naughty boy. Youâre going to do it right here. Where I can see.â
She pats her thigh. âCome stand right in front of me. Thatâs it. Close enough that I can watch.â
You shuffle forward until youâre standing between her knees, your erection level with her face. The position is unbearably exposed.
âGood. Now, I want you to show me your practice routine. The one youâve been doing in your head all evening while you pretended to work.â
Her eyes lock on yours. âPut your hand on your little guy. Go on, sweetie. Show me how you do it when youâre alone.â
Your hand moves as if pulled by strings. Your fingers wrap around your shaft. The touch is electric, shameful, thrilling.
âSlowly,â she instructs, her voice a soft murmur. âI want to see your routine. Up and down. Thatâs it. Just like you do when youâre thinking about me.â
You begin to stroke. The rhythm is familiar, but now itâs a performance. Her eyes donât leave your hand, studying each movement with detached interest.
âYouâve had a lot of practice, havenât you?â she observes. âAll those nights. All those mornings. Getting your little guy ready for this.â
She tilts her head. She smiles, a small, knowing curve of her lips. âYou know I don't want to have sex with you, donât you? Your little guy isnât designed for sex. Itâs just for this. A microphone tuned to me. For training. For compliance.â
She says it without cruelty, a simple statement of fact. âAnd thatâs okay. Thatâs what itâs good for. Look how happy he is to be training for me.â
Her words coil around your arousal, tightening it. Youâre close. You can feel the pressure building, your breaths coming in short pants.
âI can see youâre getting there,â she says, her voice dropping to a conspiratorial hush.
âThatâs good. But weâre not making a mess on the carpet.â She lifts her hand, palm up, and holds it just below the tip of your cock.
âWhen youâre ready, youâre going to do it right here. Into my hand. Every drop. Thatâs where it belongs. Do you understand?â
You nod, frantic, your strokes becoming jerky, desperate.
âUse your words, sweetie.â
âYes,â you choke out.
âYes, what?â
âYes, Iâll cum in your hand.â
âGood boy.â Her praise is like a trigger. âNow. Let me see. Show me what all that practice was for. Come for me.â
With a broken groan, you obey. The orgasm crashes through you, and you watch, mesmerized and mortified, as your semen pulses into her waiting palmâthick, white spurts that land with soft, wet sounds.
She doesnât flinch. She holds her hand steady, catching every last drop until youâre spent, shuddering, softening in your own grip.
For a moment, thereâs only the sound of your ragged breathing. Youâre floating, empty, blissfully blank.
Then Jessica holds up her hand. Itâs glistening with your come, thick and white in the lamplight.
âLook at the mess you made,â she says, not unkindly. âAll over my hand. Thatâs not very polite, is it?â
You shake your head, wordless.
âNo, itâs not. But thatâs okay. Youâre going to clean it up.â She holds her hand out. âLick up your cum. Lick it all up. Every drop. You made it, you clean it. Thatâs the rule.â
The command should revolt you. But in this dazed, post-orgasmic state, it feels inevitable. Right. A perfect, circular justice. You lean forward and lick her palm.
The taste is salty, bitter, familiar and alien at the same time. You lick her palm clean, your tongue swiping over her skin, collecting every trace of yourself.
She watches you, her expression one of mild approval, like a mother watching a child finish their vegetables.
âThereâs a good boy,â she murmurs. âMy little cum licker. Get it all cleaned up. That's it. All of it into your tummy.â
You keep lapping at her hand until she pulls it away. You pull back. She examines her hand, then wipes it on your shirt. âGood boy,â she says. âSee? Everythingâs tidy now. No mess. No evidence.â
She stands up, smoothing her sweatshirt. Youâre still naked from the waist down, your mind soft and quiet.
âPull up your pants, sweetie,â she says, her voice back to its normal, cheerful babysitter tone.
You scramble into your boxers and khakis, your fingers clumsy.
By the time youâre dressed, Jessica's gathering her things, slipping her phone into her back pocket. She pauses at the door, turning back to look at you. Her expression is thoughtful, satisfied.
You stand in the living room, your ass still warm, your mouth still holding the memory of the taste. You feel⌠calm. Empty. Better than youâve felt in months.
âYou did well tonight, sweetie,â she says, her voice warm with approval. âFor a first session. You took your spanking, you showed me your routine, you licked up your mess. Thatâs a good start.â
She opens the door, the night air cool against your flushed skin.
âI think your little guy and I understand each other now. He just needs proper supervision. And youâŚâ She smiles, a small, knowing curve of her lips.
âYou need someone to tell you when and how. So from now on, thatâs me. When you feel that⌠pressure building up, you text me. You ask. No more sneaky staring, no more hiding. Weâll schedule your practice. Weâll keep him trained.â
She steps out onto the porch, then glances back over her shoulder. âGet some sleep. Iâll see you Friday. And sweetie?â She waits until your eyes meet hers. âDonât touch yourself before then. Let it build. Itâll be better for your training.â
Then sheâs gone, the door clicking softly shut behind her. Youâre left standing in the quiet house, the new rule already taking root in your blood, the promise of Friday a low, sweet hum in your empty body.
This is a standalone story in the Haileyverse â a man, a sitter, and the relief of finally being supervised.
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