The Sitter
The babysitter’s name is Jessica. She’s 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 it’s down, brushing her shoulders, and she’s 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. You’ve been imagining that texture for the last forty-seven minutes.
Your call ended an hour ago—a tedious, interminable Zoom with the regional managers that required your full attention, which is why you’d booked Jessica in the first place.
The boys were still up then, needing dinner, needing baths, needing the kind of focus you couldn’t 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.
You’re in the living room, the report you promised yourself you’d start sits open and unread on your screen, a gray wall of text you’ve 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.
You’ve 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 shouldn’t. You’re thirty-nine. Divorced. You have a mortgage, a minivan, a membership at Costco.
But you’ve been watching her since your meeting ended, and the watching has become a low, persistent hum in your blood, a frequency you can’t 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 it’s useless. You’re hard. You’ve been half-hard since she took off her shoes and padded around in socks, her feet small and pale against the hardwood.
It’s pathetic. You know it’s pathetic. A man your age, staring at a woman half his age, in his own house while his children sleep upstairs.
But knowing it’s pathetic doesn’t 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 air—the 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 haven’t absorbed a word of.
She stops beside the couch. You can smell her—laundry detergent, the faint sweet scent of the kids’ fruit snacks, something underneath that is just her, hot and clean.
You force yourself to look up. She’s standing there, the dish towel draped over her shoulder, her head tilted slightly. Her eyes are a clear, direct blue.
She’s not smiling, but she’s not frowning either. She looks… curious. Like she’s found an interesting bug and is deciding what to do with it.
“Yes, Jessica? Everything okay?”
“Everything’s fine. The boys are out cold. I checked on them twice.”
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. “You’ve been staring at me all night.”
It’s not a question. It’s a statement. Delivered in the same tone she might use to say the dishwasher is finished. Matter-of-fact. Unembarrassed.
Your mouth goes dry. “I—I haven’t been staring. I’ve been working.”
She nods slowly, as if considering this. “You’ve 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 I’m facing you.” She says it all evenly, clinically. “That’s staring, sweetie.”
The word lands on you like a physical touch—a warm, dismissive pat on the head. Sweetie. Not your name. Not sir. Sweetie. Your face, already hot with shame, burns hotter.
It’s the kind of thing you’d 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 you—the part that’s been hard since she walked in—flutters in response. It’s permission of a kind. An intimacy. She’s named you, and the name makes you hers.
“I’m sorry,” you mumble, looking down at your hands. “I didn’t mean to make you uncomfortable.”
“You haven’t made me uncomfortable.” She says it so simply you have to look up again. She’s still watching you, that same thoughtful expression on her face. “It’s just a thing that’s happening. You’re staring. Your penis is hard. Your face is red. These are facts.”
She takes a step closer. You shrink back instinctively, but there’s nowhere to go. The couch is against the wall.
“The question,” she says, her voice dropping to a conversational murmur, “is what we’re going to do about it.”
We. She said we. As if this is a shared problem, a project for the two of you.
Not what I’m going to do about you, but what we’re going to do about it. The word settles in the air between you, intimate and terrifying.
“I… I’ll go to my room,” you stammer. “I’ll leave you alone. I’m sorry.”
She shakes her head, a small, almost imperceptible movement.
“That doesn’t solve the problem, sweetie. The problem isn’t that you’re here. The problem is that you’re like this.”
Her gesture is vague, encompassing your whole embarrassed, aroused body.
“If you go to your room, you’ll just lie in bed and think about me. You’ll probably play with yourself. And then you’ll feel guilty, and you’ll avoid me, and it’ll be weird when I come over next time. That doesn’t help either of us.”
She’s right. Of course she’s right. That’s 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.
“So,” she continues, folding her arms loosely across her chest. The movement pushes her breasts together, and you can’t help but look. She notices you looking. She doesn’t comment. She just notes it, the way a nurse notes a symptom.
“We need to handle this. Like adults. Well, I’m an adult. You’re… you’re having a hard time being one right now, aren’t you?”
It’s not a taunt. It’s a diagnosis. Delivered with a gentle, almost sympathetic tone.
You nod, miserably. You can’t speak.
“That's okay,” she says. “Lots of men have a hard time with this. My boyfriend’s dad is the same way. He’s always looking at me when I’m over there. His wife works nights.” She says this as if sharing a mildly interesting piece of gossip. “I had to have a talk with him, too.”
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. “The thing is, sweetie, you’re not a bad guy. You’re just… needy. And when needy men don’t get what they need, they get clumsy. They stare. They make things awkward. It’s not really your fault. Your penis just gets ahead of your brain.” She tilts her head again. “You need someone to take the wheel for a little bit. Don’t you?”
You nod again. It’s the only response you’re capable of. Yes. God, yes. You’ve needed someone to take the wheel for twenty years.
“Ya, I thought so.” She smiles for the first time. It’s a warm, pretty smile, the kind that would light up a room if it weren’t currently lighting up your shame.
“Your little guy has overwhelmed you. That's why I’ll manage him. And you. So you just do exactly what I tell you. Okay?”
“Okay,” you whisper.
“Okay.” She leans down and reaches out and pats your knee. The touch is brief, impersonal, but it sends a jolt through you.
“Good. Now what you need is to learn how to behave. And to empty out all this…” She gestures at your crotch. “…this nervous energy. So you can be a good dad and a good man and not a creepy guy staring at the babysitter.”
Every word is a nail hammered into the coffin of your dignity. And every nail feels like a release.
“Now,” she says, her voice dropping back into that calm, instructional tone. “You stared at my body without permission. That’s rude. When someone is rude, there are consequences. You understand that, right? You teach your boys that.”
“Yes.”
“So you’re 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.”
She says it the way she might say you’re 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.
“Let's get started,” she says, turning and walking toward the armchair in the corner—the big, plush one. She sits down, primly, smoothing her leggings over her thighs.
“Come here. Pants and underwear down to your ankles.”
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. You’ve never felt more exposed, more utterly seen.
Jessica’s eyes drop to your erection. She studies it for a moment, her head tilted.
“He’s very eager, isn’t he?” she observes. “Even now, when you’re about to be corrected. He doesn’t know any better.”
She looks up at your face, her gaze steady. “But you should, sweetie. He may overwhelm you but you’re the one who let him. That’s why you need training.”
She pats her thigh. “Over my lap. Carefully. I don’t want you poking me with that thing.”
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. “This is going to sting a little,” she says conversationally. “But it’s for your own good. Count for me, okay? Count each one. If you lose count, we start over.”
“Yes, Jessica.”
The first spank lands. It’s not as hard as you expected, but it’s sharp, crisp. The sound is loud in the quiet room.
“One,” you say, your voice shaky.
The second. A little harder. “Two.”
She finds a rhythm. Not too fast, not too slow. Each spank lands on a different part of your buttocks, spreading the sting. You’re not in pain, not really.
It’s 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. You’re leaking precum, you can feel it, a wet spot forming on her leggings.
“You’re getting wet on me, sweetie,” she notes, her hand pausing. “Your little guy is leaking. Even while you’re being corrected. He likes this, doesn't he?”
“Yes,” you gasp.
“We’ll have to do something about that later. Keep counting.”
“Three… four… five…”
By ten, your ass is warm and tingling, and you’re so hard it’s almost painful. She stops. Her hand rubs your back in slow circles.
“There. All done. That wasn’t so bad, was it?”
“No.”
“Good. You took your punishment like a good boy.” She helps you ease off her lap. You stand before her again, your erection bobbing, your ass throbbing. You feel dazed, pliant, utterly hers.
“Now,” she says, looking up at you from the chair. Her voice is calm, instructional.
“We have the other problem. The leaking problem. Your little guy is still all worked up. He’s been like this all night, hasn’t he? Practicing in your head. Getting ready.”
She leans back slightly, her gaze dropping to your erection. “All that pent-up energy needs to go somewhere. But we’re not going to make a mess. And we’re not going to let you sneak off and do it alone like a naughty boy. You’re going to do it right here. Where I can see.”
She pats her thigh. “Come stand right in front of me. That’s it. Close enough that I can watch.”
You shuffle forward until you’re standing between her knees, your erection level with her face. The position is unbearably exposed.
“Good. Now, I want you to show me your practice routine. The one you’ve been doing in your head all evening while you pretended to work.”
Her eyes lock on yours. “Put your hand on your little guy. Go on, sweetie. Show me how you do it when you’re alone.”
Your hand moves as if pulled by strings. Your fingers wrap around your shaft. The touch is electric, shameful, thrilling.
“Slowly,” she instructs, her voice a soft murmur. “I want to see your routine. Up and down. That’s it. Just like you do when you’re thinking about me.”
You begin to stroke. The rhythm is familiar, but now it’s a performance. Her eyes don’t leave your hand, studying each movement with detached interest.
“You’ve had a lot of practice, haven’t you?” she observes. “All those nights. All those mornings. Getting your little guy ready for this.”
She tilts her head. She smiles, a small, knowing curve of her lips. “You know I don't want to have sex with you, don’t you? Your little guy isn’t designed for sex. It’s just for this. A microphone tuned to me. For training. For compliance.”
She says it without cruelty, a simple statement of fact. “And that’s okay. That’s what it’s good for. Look how happy he is to be training for me.”
Her words coil around your arousal, tightening it. You’re close. You can feel the pressure building, your breaths coming in short pants.
“I can see you’re getting there,” she says, her voice dropping to a conspiratorial hush.
“That’s good. But we’re not making a mess on the carpet.” She lifts her hand, palm up, and holds it just below the tip of your cock.
“When you’re ready, you’re going to do it right here. Into my hand. Every drop. That’s where it belongs. Do you understand?”
You nod, frantic, your strokes becoming jerky, desperate.
“Use your words, sweetie.”
“Yes,” you choke out.
“Yes, what?”
“Yes, I’ll cum in your hand.”
“Good boy.” Her praise is like a trigger. “Now. Let me see. Show me what all that practice was for. Come for me.”
With a broken groan, you obey. The orgasm crashes through you, and you watch, mesmerized and mortified, as your semen pulses into her waiting palm—thick, white spurts that land with soft, wet sounds.
She doesn’t flinch. She holds her hand steady, catching every last drop until you’re spent, shuddering, softening in your own grip.
For a moment, there’s only the sound of your ragged breathing. You’re floating, empty, blissfully blank.
Then Jessica holds up her hand. It’s glistening with your come, thick and white in the lamplight.
“Look at the mess you made,” she says, not unkindly. “All over my hand. That’s not very polite, is it?”
You shake your head, wordless.
“No, it’s not. But that’s okay. You’re going to clean it up.” She holds her hand out. “Lick up your cum. Lick it all up. Every drop. You made it, you clean it. That’s the rule.”
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.
“There’s a good boy,” she murmurs. “My little cum licker. Get it all cleaned up. That's it. All of it into your tummy.”
You keep lapping at her hand until she pulls it away. You pull back. She examines her hand, then wipes it on your shirt. “Good boy,” she says. “See? Everything’s tidy now. No mess. No evidence.”
She stands up, smoothing her sweatshirt. You’re still naked from the waist down, your mind soft and quiet.
“Pull up your pants, sweetie,” she says, her voice back to its normal, cheerful babysitter tone.
You scramble into your boxers and khakis, your fingers clumsy.
By the time you’re 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 you’ve felt in months.
“You did well tonight, sweetie,” she says, her voice warm with approval. “For a first session. You took your spanking, you showed me your routine, you licked up your mess. That’s a good start.”
She opens the door, the night air cool against your flushed skin.
“I think your little guy and I understand each other now. He just needs proper supervision. And you…” She smiles, a small, knowing curve of her lips.
“You need someone to tell you when and how. So from now on, that’s me. When you feel that… pressure building up, you text me. You ask. No more sneaky staring, no more hiding. We’ll schedule your practice. We’ll keep him trained.”
She steps out onto the porch, then glances back over her shoulder. “Get some sleep. I’ll see you Friday. And sweetie?” She waits until your eyes meet hers. “Don’t touch yourself before then. Let it build. It’ll be better for your training.”
Then she’s gone, the door clicking softly shut behind her. You’re 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 — a man, a sitter, and the relief of finally being supervised.
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