I wake the next morning with a smile on my face as I reach for my phone to silence the alarm. Normally I wake up before it goes off, but today I haven’t, despite the good night’s sleep. As I do, I notice the notification on the Mystery Matchmaker app signaling a new message and my smile grows.
Clicking open the app, I navigate to the messages section to see what my mystery match has sent. She must have sent it after we said goodnight last night, almost as though it was an afterthought.
WineQueenFamilyTruckster: tell me something Clark, why do guys feel compelled to send dick pics all the time?
I laugh out loud, her question not what I was expecting as my fingers type out a quick response.
Me: no idea? Trying to prove a point? Trying to get laid? Because they’re idiots?
I immediately see the bubbles pop up to signify she’s responding, so I prop some pillows behind my head and wait to see what she has to say.
WineQueenFamilyTruckster: early bird, huh? But do they not realize that it’s just plain stupid and only makes them look like try-hard losers?
Me: yep, you too? I don’t know, this is my first time doing this kind of thing, and like I said before, I apologize for my gender. We really have no clue most of the time.
WineQueenFamilyTruckster: Yep. You seem to…
Her comments make me pause, my thumb hovering over the screen as I try to figure out what to say in response. Clearly, had I gone with the stupid username Jack had given me, I never would have matched with this chick. Well, maybe we’d have matched, but I was damn sure we wouldn’t be chatting like this. I mean blue balls? For fuck’s sake, like that didn’t scream desperate loser looking to get laid.
I mean yeah, I was looking to get laid, obviously, but not at the expense of my pride or integrity. And even though random hook-ups and one-night stands aren’t really my thing, I’m not opposed to a regular booty call situation if that’s what this girl might be into.
Me: so I guess this would be the wrong time to send a dick pic?
Me: joking obviously…
I don’t know why I respond like this, only that it feels natural. We’ve had this easy banter going ever since we started chatting last night and even though I have absolutely no intention of actually sending her a dick pic, I’m not above playing around with her about it.
WineQueenFamilyTruckster: Idk…would you?
“Holy fuck,” I breathe out as my dick actually hardens beneath the covers. “Is she serious?” I don’t even know who I’m talking to or who I expect to actually answer me given I’m lying alone in bed in my otherwise empty house.
Me: you want one?
Me: I thought dick pics were a turn off??
WineQueenFamilyTruckster: as a first line of communication yeah…I mean shit, buy a girl a drink first.
I burst out laughing, scrubbing a hand over my face as I actually contemplate doing this. God knows now is the right time given my dick is as hard as a rock. Sure, it could be partly due to the standard morning wood, but a part of me knows it’s also due to this easy flirty banter wine queen and I have going on.
Wine queen? Does that mean she likes wine or she works in the wine industry? Even though we both agreed to none of that bullshit small talk about jobs and stuff, I do know she lives in the area. When Jack had set this up for me, he made sure to set my match profile to a fifty mile radius, so it’s a safe bet this mystery girl lives in or around Napa.
Fuck, do I already know her?
WineQueenFamilyTruckster: hey, so I’m only joking…you don’t have to actually send me one, obviously…
Me: no, I’m just…thinking…
I could feel myself smiling like a motherfucker now, my dick growing impossibly harder as I type out a response.
Me: something’s hard, that’s for sure.
The conversation goes quiet. No response from wine queen and no bubbles to signify she’s even typing. I wait a few minutes, trying to decide if I’ve maybe crossed the line with my response. I’d thought we were good, both of us enjoying this easy flirtiness we’ve fallen into, but maybe I’ve misread the situation. God knows, it’s been a long fucking time since I had to pick up a woman.
Me: hey listen, I’m sorry, I shouldn’t have said that.
WineQueenFamilyTruckster: NO! It’s cool, sorry, I just needed a minute there…
Me: a minute for?
WineQueenFamilyTruckster: wouldn’t you like to know 😉
“Fuck me,” I mumble as I give in and my hand now moves below the covers to my dick. Did she seriously just get herself off to thoughts of my hard dick? The idea of her doing that turns me on and as I start to stroke myself, I start to wonder if I should not only send her a picture, but actually ask if she wants to come over.
WineQueenFamilyTruckster: but…I gotta go, work calls.
WineQueenFamilyTruckster: you still owe me a pic btw
She signs off after that, not responding to the simple goodbye I type back in response. Throwing my phone onto the bed, I let out a long groan, kicking the covers off as I close my eyes and try to imagine my mystery match and who she might be or what she might feel like lying here in this bed with me, her hand on my dick as she works me over.
I park my car out in front of the work sheds, grabbing my coffee mug from the center console, before walking into the main building to check on the list for today.
“Morning,” I say as I head into Lauren’s office.
“Hey, Tommy,” she calls back. “Here’s today’s schedule.” She hands me a typed-up list of all the things that need to get done today. Lauren’s always been meticulous and organized and it’s one of the many things I like about working here.
“Thanks. How are you? Good?”
Lauren shoots me a weird look. “Yeah,” she replies, dragging the word out slowly. “You?”
I flash her a smile. “Great, thanks,” I say before turning to Jack who has just walked in the room. “Jack,” I greet with a nod.
“BB,” he shoots back with a grin.
I stop, turning to look at him. “What did you say?”
Jack’s grin widens. “BB, you know, short for blue—”
I hold a hand up to stop him. “Got it. Thanks. No need for that though.”
“Ohhhh,” Jack says, his eyes widening. “So, the app worked, huh? And you got yourself some—”
“I’m going now,” I say, cutting him off as I walk out of the office, having no desire to discuss my sex life or lack thereof with either of my bosses. The last thing I need is those two on my case about it.
As I head down the corridor toward the tasting room, I spy Penny coming toward me, her head down, her eyes on her phone as she walks. I move to the side to let her pass, but for some weird reason, she does the same and before I can get out of the way, she slams straight into me, knocking my coffee and her phone to the floor.
“Shit!” she practically yells as she crouches down, scrambling for her phone.
“You okay?” I ask, reaching for her elbow and helping her up.
Her cheeks are a little flushed and when she looks up at me, I watch as it darkens, making my pulse thud. But when she pulls her bottom lip between her teeth, it sends a spike of lust straight to my dick.
She’s your co-worker, you idiot, calm down.
“Sorry,” she says, tucking a loose strand of hair behind her ear. “Wasn’t watching where I was going.”
“Clearly,” I tease, raising a brow at her. “Something interesting on there?” I add, lifting my chin toward the phone in her hand.
Penny swallows hard as that blush now spreads, moving down her neck and across her chest, which is barely hidden by the low-cut Somerville Winery t-shirt she wears. Something about the contrast between her flushed skin and the stark whiteness of her shirt has me practically salivating.
She’s also ten years younger than you, remember?
God, I don’t know what the fuck is wrong with me. It’s like a tiny bit of flirting via a stupid dating app that I didn’t even download, let alone want to use, and suddenly I’m a fucking mess, thinking and saying all sorts of stupid things.
“Umm, yeah, something like that,” she mumbles, sliding her phone into her back pocket as though she doesn’t want me to see whatever it was she was looking at.
“It wasn’t p—”
“Penny?” Lauren’s voice cuts off my question, which is a good thing, because I have absolutely no business asking it.
“Yeah, coming,” she calls back, her voice husky and low, the words actually making me groan as she brushes past me and disappears into Lauren’s office.
Taking a deep breath, I walk away from whatever the fuck that was and outside toward the work sheds and all the jobs I have to do, mentally reminding myself that Penny is not only completely off-limits, but also someone I am most definitely not interested in.
“Focus on your mystery match, you idiot,” I mumble to myself as I realize my coffee mug is still lying on the floor outside Lauren’s office. “And get your mind off your co-worker.”