Take a Chance

Mm, lights are all out.

Guess I’m not surprised. It’s… ooh, way later than I thought it was. Yeah, you and Ben are probably already asleep.

One of these days, I’m going to show you just how grateful I am. I don’t think I’ve ever had such an accommodating babysitter. I mean, just this year alone I’ve been through three major shift changes and you weren’t fazed once.

And then that whole month where I was only working night shifts… I hope you know just how much easier you’ve made my life since I hired you.

Being a single dad isn’t easy. Actually, it’s pretty tough.

God, I was a wreck when I first hired you. I had just gotten this new job and moved my son from his childhood home to a totally new neighborhood on a different side of town.

Ben is a good kid and easy to take care of, kind of takes care of himself, really. I mostly just needed to find someone who could make sure he did his homework and had something other than fruit snacks for dinner.

You live down the street from us and we were always running into each other at the park on the weekends where you bring your dog.

Casual chats turned into a genuine friendship between us. And… of course… more than a little attraction.

You just graduated college a couple of months ago and you’re spending the summer here working odd jobs while figuring out what your next move is going to be.

You don’t have a traditional 9-to-5 at the moment, so you offered to watch my son on nights I work late.

You’re touchy with me, always standing up on your tip-toes to run a hand through my hair and tell me how good it looks today. Or gently putting your hand on my arm when you come up to say hello.

You’re fine, and you know it. And I’ve wondered on more than one occasion what your intentions are. You’re well aware of how much older I am than you, but… you still seem dead set on giving me attention.

What we have, this friendship and occasional babysitting gig, is great. I’d be lying if I said I didn’t want more.

But… that would run the risk of making this situation awkward. Or ending it altogether.

The bedroom is dark except for the soft yellow light from the lamp on my bedside table. You’re lying in the middle of my bed, dozing beneath the thick white duvet.

There’s just something so hot about seeing you in my bed…

I offered it up to you on nights like this when I’m working late. I hated coming home and seeing you all curled up on my cramped little couch.

“Hey.”

I reach down and gently touch your shoulder.

Your eyes flutter open. You smile up at me and my breath catches in my throat.

“Hey.”

“Sorry, it was so late again. How did everything go?”

“No need to be sorry. All good, as always.”

“Maybe when you’re here. Speaking of which, would you mind sticking around for a few more minutes? I just want to take a quick shower.”

“Yeah, yeah, of course.”

“Thank you, really, I appreciate it.”

I head into the bathroom and quickly shed my clothes. I can’t help but wonder to myself how you feel about being in my bed… Obviously, you’re fine with it, but I wonder if it makes you think about me… makes you wonder what I look like in bed…

“Hey, real quick, I just wanted to ask if you know your schedule for next week yet. I’m thinking about going on a last-minute beach trip with some friends and I just want to make sure I don’t leave you high and dry.”

Bold of you to come into the bathroom knowing I’m in the shower. I’ll take that as a sign that you’re very comfortable around me…

You standing on just the other side of the shower curtain with just a thin bit of vinyl separating us is making it very difficult to summon the details of my work schedule.

“Um… you know, I can’t remember off the top of my head which days I’m working. I’ll need to take a look at my phone.”

“I can grab it for you.”

“It’s in the right pants pocket. You can open my calendar and you’ll see it.”

“Oh, so you want me to put my hands down your pants?”

“You said it, not me.”

“Looks like you’ve got a pretty stacked schedule, but you aren’t working late on the days I’d be gone.”

“Please don’t remind me. I am very overdue for a vacation.”

“Maybe I should cancel my beach trip with the girls and take you instead.”

“Yeah, maybe.”

“Do you ever do anything fun for yourself?”

“Like what?”

“Anything that isn’t work or dad things?”

“No, not really.”

I’m pretty much finished in the shower, but I keep the water running. I like chatting with you, having these conversations where we learn a little more and more about each other each time.

“You’ve never asked me to babysit for a date night or anything.”

“Yeah, well, date nights would require a social life and I don’t really have one at the moment…”

“So, you’re not seeing anyone?”

“Nope. Not at the moment.”

I’m trying hard not to read too much into your tone, but… that sounded hopeful on your end. My cock twitches a little bit, but… nah, I’m not going to get my hopes up.

“Well, if you had the time, would you? Date, I mean.”

“Yeah, definitely. But… I mean, I love single-dad life, but… yeah. I’m just not really into, like, all the apps and stuff.”

“Yeah, yeah, I know what you mean. I’m not either. I find it much more enjoyable to just… meet someone organically… you know?”

“Yeah, I know what you mean. I really do…”

“Okay, well, I’ll let you finish up in here.”

Okay, if that wasn’t flirting, I don’t know what is.

I climb out of the shower and wrap a towel around my waist, but it does little to hide the fact that I’m just a little bit turned on at the moment. Just thinking about you… wanting me… and you looking so good in my bed when I got home tonight.

I head into the bedroom and over to my dresser.

“Oh—”

You’re back in my bed, just how I found you before, with the sheets pulled up to your chin. Your shoulders are bare and the tank top you were just wearing is lying at the foot of the bed. Along with your underwear and a very small pair of shorts.

“And what would you be doing?”

“Making it easy for you.”

“Easy for me to do… what exactly?”

“Do you need a written invitation? I’ve been trying to be subtle for months, but I was kind of starting to doubt you’d ever pick up on it.”

Your lips twist into a half smile as I slowly make my way toward the bed. Too good to be true doesn’t even begin to describe this situation.

“Are you trying to say I’m dense?”

“I’m saying I want you to fuck me.”

“Mmm, is that so?”

“Come here.”

I climb onto the bed, slowly, and throw one knee over your hips. I bend down to kiss you and you meet me halfway with a hungry, desperate touch.

My body is buzzing with desire and my cock is on its way to being rock hard.

“So, the fact that I’m… much older than you… and the fact that I’m employing you… you don’t think that’s wrong?”

“That’s kind of why it’s so hot, don’t you think? Now, do you need any more explanations, or are you going to fuck me?”

“No, no more explanations needed.”

I drag my hand over my shaft as we kiss. Man, I’m so hard.

Your hands wrap around my neck and I drift my mouth down to your neck.

I push my knee between your legs and you ride up against me like you’re desperate to have your clit touched.

“You’re really, really turned on right now, aren’t you? Why don’t you tell me a little more about how badly you want me to fuck you?”

“I’ve just been… thinking about you so much… and how good it would feel to have you touch me…”

You rub your pussy harder up against my thigh, teasing your clit just by rolling your hips into me.

“All those times at the park you’ve flirted with me… you were secretly thinking about me fucking you?”

“Yeah. I was imagining your cock… holding it. Sucking it. Taking it deep.”

A flash of white-hot desire travels from my head to my toes. You… are just incredible.

I slide down your body and kiss from the dip of your collarbone down to the middle of your breasts. Your nipple hardens as soon as it’s in my mouth.

“Oh, fuck yeah…”

My fingers dance at your hips and trail slowly, slowly towards your inner thighs. I cannot wait to fuck you. But with how good you are with your words, I kind of want to hear you beg for it…

“So, you want this cock, huh? How do you want it?”

“Yeah, let me hold it.”

Your hand grasps for my shaft. You jerk it with slow, tight pulls.

“Oh, yeah, there you go. Is that what you’ve been wanting, huh? You’ve been wanting this cock?”

“Oh my god, yeah. I can’t wait to have it in me.”

I take your other nipple into my mouth and suck hard, dragging my teeth across your sensitive skin. Your body jerks and writhes beneath mine with every little movement of my tongue.

I slip one hand between your legs and slowly draw my fingers between your folds.

“Nice and wet for me. You feel how slick you are? Is that how bad you’ve wanted this?”

“Yeah, yeah, I’ve been fucking thinking about this for so long. Fuck me… please—”

I push two fingers up against your clit and swirl them around. I want to tease you as long as I can… get you nice and worked up for me before giving you my dick.

“Oh, yeah, right there…”

“Yeah? You like that? Like getting fucked by your employer?”

“Yeah, yeah… I’m so bad for wanting this, aren’t I?”

“Yeah, it’s very wrong.”

“And are you going to punish me for it?”

“Yeah, I think I am.”

I sit up on my knees and grab each of your ankles, setting them on my shoulders so I can have the best access to your pussy.

My dick is throbbing in my hand as I guide it to your entrance.

“You ready? Ready for this dick you’ve been wanting so bad?”

“Yeah, yeah, please—”

My dick slides into you so easily. I go in an inch… and then another… and another… watching your pussy take me in the whole time.

Your pussy takes me all the way in and I start a quick, tight rhythm.

I drive into you harder… harder… gripping onto one of your ankles with one hand and holding onto the top of the headboard with the other. You feel so good…

“Harder, harder…!”

I drag my teeth across your shoulder, up your neck, to your jaw, and finally find your lips.

Your pussy squeezes around my cock. The feeling of your walls tightening around me… oh my god, it’s so damn good…

“F-fuck, touch my clit. Play with my clit while you fuck me.”

“Oh my god… you feel… so good. Just like that. You like that? Yeah, you like that, don’t you?”

“I’m getting close—I’m close, I’m close—”

“Me too, me too. Do you want me to…?”

“Yes, cum inside me! Oh my god, fill me up!”

I collapse forward onto you and press my lips against your neck again.

“Um… thank you.”

“Don’t thank me. Just promise to fuck me again tomorrow.”

“Mmm, that I can definitely do.”