The Babysitter

I think I’m done with dating apps for a while. Every date I go on feels so…tedious. Like we both know we’re not meant for one another, but we go through the motions of pretending we could be. And for what? It all just seems kind of pointless.

The woman I met with tonight was on her phone through half of our dinner, but to be honest I’m kind of glad we didn’t have to fill our time with small talk. Ah, whatever. If I’m meant to find love again, I’m sure it’ll find me.

For now, I’m more than happy as a single dad. More time to spend with my son and focus on my business. Speaking of, I hope he’s asleep by now. You seemed like you could handle him, but the smooth-talker probably convinced you to let him stay up until I get home.

The house is quiet except for the sound of the TV. I make my way to the living room and see you lounging on the couch. This is your first time babysitting for me. You came with a great recommendation from my neighbor. You just finished college, I think, and you’re spending the summer at your parent’s house while you prepare to move to Amsterdam for a job.

“Hey.”

“Oh, hey. There you are. Good date? ”

“Yeah, yeah. Actually…no. Not really. It was pretty bad, now that I think about it. ”

“Oof. Sorry to hear that. ”

Your smile catches me off guard and I catch myself staring at you for longer than I should before I break eye contact. When you arrived earlier, I was kind of nervous about my date, not to mention running late - I don’t think I took the time to really notice you.

I sit down on the couch beside you and slide my hands behind my head.

“Ah, that’s okay. Honestly, I’m not too disappointed. It was nice to go out, but…you can’t force these things, right? ”

“No, you definitely can’t. I’m surprised, though. I mean, come on, who wouldn’t want to go out on a date with you?”

I’m a little taken aback and I hope it doesn’t show. Was that you just being polite? Or are you hitting on me? You’re quite a bit younger than me, but… maybe you’re interested?

I glance over at you and something just kind of…washes over me. I’m really attracted to you. Damn, talk about a stereotype. The divorced dad who is interested in his kid’s babysitter…but really, I mean… fuck. There’s something very sexy about you that I can’t quite put my finger on.

“Your son was great, by the way. He’s, um...wise beyond his years.”

“Oh, good, good…yeah, he’s seven going on seventeen.”

My mind quickly turns to fantasy. How would your lips feel on mine? Would you like the feel of my hand going up your back…my fingers playing with your nipples...? Is there a spot on your body you love to be touched? One that makes you arch your back and bite your lip?

“So...”

“Oh, right. Right! Here, let me get you some cash. Thanks for everything tonight... ”

“You, uh, look like you spaced out on me there for a second. What were you thinking about? ”

“Um, well…to be honest, I was thinking about you.”

“Me? What about me?”

“Your eyes, they’re...really beautiful. And that dress...it looks great on you.”

I search your eyes and see that you’re enjoying this little flirtation we’ve somehow stumbled into.

“Huh. That’s funny, because…I’ve been thinking about you all night. Your eyes. Your mouth. Your cock.”

You lean forward closer to me, your lips parted, and run your tongue over your lower lip. Holy shit.

The shape of your breasts in that dress...damn. They’re perky, not quite round. Two tattoos curl around your upper arm. I wonder if you have any more I can’t see yet. Your thick, delicious thighs look so damn squeezable...

Suddenly, you lean forward and kiss me, pressing your body into mine.

“I was pleasantly surprised when I met you. Most of the people I babysit for are…not as intriguing as you. ”

“Oh yeah? And how am I different from them? ”

“Well…you seem like you have a soft side behind that whole tall, dark, and handsome thing you’ve got going on.”

“A soft side, huh? Well, what if I don’t? What if…I like things a little rough? ”

“Well...I’d say you have to show me just how rough you like it.”

My cock twitches with excitement. You are…something else.

A rush of adrenaline goes through me at your words. You put your hands on my chest and push me until I’m reclining back on the couch with your legs straddling me. I hold you by the hips as you start to grind down onto my lap. My cock is throbbing, desperate for you. You look down at me with this little teasing grin. If you like it rough, then I’ll just have to give you what you want. I sit up and quickly–easily–flip our positions. You’re below me now and I waste no time kissing you again.

I drag my lips across your jaw and down to your neck. You squirm beneath me and I know I’ve found a sensitive spot...

I move further and further down your body until my mouth is at your cleavage. I left your dress, desperate to get it off of you, and you assist me in pulling it over your head. Your breasts tumble out in front of me, hidden behind a black bra which you quickly strip off. I swirl my tongue around one nipple, then the other...

“Oh, fuck, yeah…harder.”

I use my teeth and bite down on the sensitive skin. I suck, hard, until you’re gripping my shoulders and bucking your body against mine. I slip my leg between your knees and press up just slightly so I’m grinding against your pussy. You bear down, hard, on my knee and ride it.

“Oh, yeah. I’m getting fucking wet for you. Take off your pants. ”

I switch back and forth between your nipples a few times before standing up and sliding my pants off. Fuck, I need to see you spread out on my bed, not this cramped leather couch.

“C’mon. We’re going to the bedroom...”

I offer you my hand and you take it. I lead you away from the living room and down the hall. I guide you backwards until the back of your knees hit the edge of my bed. I lift you up around your hips, drop you onto the linen duvet, and push your legs apart.

“You always take what you want without asking?”

“Well, I am your employer tonight, after all…”

I pin your wrists to the pillow and push your head to the side with my nose. I bite down on your earlobe and suck hard on it.

Pre-cum is leaking from my cock as I roll my hips into yours. I can feel it through my boxers.

“Is this what you want, hm? You want my dick? ”

“I want you to quit teasing me and fuck me already. I’ve been thinking about your cock since the moment I met you tonight. ”

I silence you with another hard kiss. I’m so fucking horny right now.

I release your wrists and yank down my boxers. I grab a condom out of the drawer and quickly roll it on. My cock teases your entrance as I grin down at you.

“You want this? Yeah? Tell me how bad you want it. ”

“Oh, what, you want me to beg for your cock?”

“Yeah, I want you to beg for it.”

I slide my thumb between your lips and you quickly take it in your mouth and suck on it as if it’s my dick.

“Fuck me, right now.”

Your lips pucker around it and the slick inside of your mouth covers my thumb with warm saliva. Fuck, you’re hot. I push my thumb further in and fuck your mouth with it.

“Oh, yeah…you like that?”

“Please…”

I use my free hand to guide the tip of my cock between your legs. Our eyes connect for a moment and I thrust my hips forward.

Your eyes squeeze shut as I enter you and your hands grasp so tight around my back that I’m sure you’re going to leave a mark. You bounce your hips against mine as we fuck.

“Pull my hair...”

“Like that?”

“Oh, harder!”

I yank on your hair and my beard scrapes against your cheek as I press my face into your neck.

“You feel me? You feel every inch of me inside you? ”

I grab onto your thighs and lift your legs up. You settle them on my shoulders and the change in angle lets me go even deeper inside you.

“Fuck, you’re so big.”

“Yes, you can take it. Take my dick, take it all...”

“Turn over.”

My cock falls out as you flip over onto your stomach and stick your ass up at me. I push your face down into the bed and thrust myself inside you once again. Your knuckles are white as you grip the sheets beneath us. I fuck you hard and fast.

I lean over you and reach around to find your clit.

“Oh, shit. Oh, shit, right there… ”

I play with your clit, rubbing it back and forth, over and over, in circles. In short, tight strokes...I press my lips into your back as I push my dick in and out of your warm, wet pussy. Fuck, I’m getting sweaty.

“You’re going to make me cum. Shit, shit. I’m going to cum, I’m going to cum... ”

“Fuck, fuck, I’m so close…”

Your walls are pulsing around my dick as you cum. Oh, god, god, that feels so good. Fuck...

I slowly pull out of you and collapse down onto the bed beside you. I look over and you’re curled into yourself, trembling. My sheets are soaked with your cum.

“Oh god. That felt so good. Can I ask you something?”

I pull off the condom and toss it into the trash can a few feet away.

“Yeah, of course.”

“Do you want to go out on a date sometime?”

“Yeah, yeah, I do. I’ll, uh, have to find a new babysitter then, huh? ”

I turn towards you and spoon your body against mine. Turns out this was a pretty good night after all.