The Bet by Max Monroe

Wednesday, March 21st

Jude

The Winslow gang is all here.

My brothers Remy, Flynn, and Ty. Winnie, her husband Wes, and my niece Lexi. And, of course, since we’re currently sitting inside her kitchen, my awesome mom is in attendance, too.

There’s also a random woman named Shirley or something that Ty brought with him, but that’s to be expected.

For the last five or so years, Wendy Winslow has made a point to bring all her kids together for Wednesday dinner. With everyone’s schedules and my siblings’ tendencies to schedule shit on the weekends when I’m working, it’s not something we manage every Wednesday, but we generally achieve it once a month.

And considering what happened two weeks ago when I had everyone show up at Winnie’s place unannounced, I have a feeling my sister made damn sure this family dinner worked out.

Tonight, an Italian-style feast of spaghetti and meatballs, lasagna, garlic bread, antipasti, and various other side dishes are on the menu. And with the way my niece Lexi is grinning from ear to ear, I have a feeling she had a say in this tasty setup.

My mom and Winnie finish setting big platters of food in the center of us, and I look across the table to meet my niece’s eyes. “Did you tell Grandma what to make tonight?”

She nods and flashes a full-toothed smile in my direction.

“Fantastic choice, Lexi Lou.”

Lex giggles as my sister begins to dish out a healthy helping of spaghetti onto her plate, and I start to reach forward to do the same for myself, but my phone buzzing in my pocket pulls my attention.

My chest expands as I tap on the screen to check my notifications, but when I see Bianca, the expansion turns to deflation. No offense, Bianca, but you’re not the person I’m wanting a message from.

I haven’t given in to any of Bianca’s hookup requests—or anyone else’s, for that matter—for nearly two months now, and I don’t have an explanation for it. But something tells me it’s because I’ve been having so much fun with sweet Sophie Sage that I haven’t needed to find it anywhere else.

It’s been nearly two days since I asked her if she could get out of work obligations so I can surprise her with a trip to the real city that doesn’t sleep, but she still hasn’t given me her official response.

The last message she sent was as vague as a jilted mom on social media trying to air out her dirty laundry without losing little Timmy’s spot on the T-ball team. Sophie’s, apparently, trying to “figure it out.”

Frankly, I don’t know if it’s a logistical delay or if she’s not getting enough satisfaction from me anymore…

Psh. It can’t be that.

I saw how she looked when she came on my cock in the Plaza bathroom, and it wasn’t the look of a woman who was thinking about how long it was going to take to finish her laundry when she got to it later.

Ha. Yeah. She definitely wants more of the fun I can offer.

I unlock the screen of my phone to double-check my ongoing chat with her just to make sure I didn’t miss a text, but all that’s there are the mocking words of her alter ego, Sophie, Team Mom.

Just the thought of that night, the one where I made the snap decision—right before I buried my face in her delicious pussy—to ask her to open up her schedule for a trip makes me smile.

Damn. That was a good fucking night.

If only she’d say yes to leaving town tonight, I could show her more good nights.

“You think Mr. Important over there is going to put his phone down for five fucking seconds to enjoy dinner with us?”

“Ty! Language!” my mom chastises with a click of her tongue. I look up to see my brother staring at me with a smug-as-fuck grin on his face, unfazed by the halfhearted snap from our mom. The truth is, we’ve been cursing up and down the streets of Manhattan for too damn long to be stopped. My mom knows. Everyone knows. But it’s part of a mother’s obligation to keep trying to turn us into decent humans, no matter how far down the path of being scumbags we may be.

“Sorry, Mom, but I think we can all agree that Jude is being a real rude prick right now.”

“I make a point never to agree with Ty on anything,” Remy chimes in, “but I’m pretty sure Jude knows that cell phones are not allowed at Wendy’s table. By doing it anyway, he is, in fact, acting like a prick.”

“Do you mean he’s a prick because he’s a penis or because he’s a man regarded as stupid, unpleasant, or contemptible?” Lexi asks around a mouthful of spaghetti. “Because I’ve seen both in Webster’s.”

The whole table nearly combusts, the laughter is so raucous, and Ty nods so hard, I think his head might fly off.

“I definitely mean he’s a penis. Definitely.”

“Ty!” Winnie chastises through her teeth, her cheeks heating to a rosy pink of embarrassment at having to deal with this shit.

“Though, by these terms, this would make Uncle Ty a penis as well, since he used his phone during family dinner too, two months and three weeks ago. We were eating tacos, and he kept checking his phone to get an update on a boxing match.”

Her commentary makes Flynn chuckle. “I think our little genius has your number, bro.”

Ty just rolls his eyes and forks a bite full of lasagna into his mouth. Winnie’s head is in her hands, and she’s given up on trying to get this whole thing reined in. But my mother has now moved her focus to me.

“Jude, you know the family dinner rules,” she says and showcases her infamous mom look at me. You know, the same look every mother uses to instill the fear of God in their children so that they can keep them in line, even when they’re rowdy, nearly uncontrollable teenagers.

“You know what, Mom? This is the best lasagna and spaghetti I’ve ever had. You’ve truly outdone yourself,” I announce, and she shakes her head on a snort.

“Don’t try to butter my biscuit to get yourself out of trouble,” she retorts. “And considering your plate is still empty, that tells me you’re full of shit right now.”

I glance down at my plate to find it is, in fact, still empty. Whoops.

“Mom just said shit at the dinner table!” Ty teases, and our mother scratches the side of her face with her middle finger.

“Mind your business, Ty.”

Wes, Winnie, Flynn, and Remy all laugh at the rare sight of Wendy flipping someone off, and I use the distraction to check the screen of my phone again. The dinner is now in pandemonium thanks to me, but I feel no shame. A man will use any means necessary for sex; it’s a scientific fact.

Still, nothing.

“All right, Jude,” Remy comments. “Why are you checking your phone like Ty when he’s waiting to hear back from one of his hippie vegan friends about a clown party?”

Ty glares.

I chuckle at Ty’s glare, and then, knowing I’m not going to be able to slither out from under Rem’s radar, I shrug. “It’s just work stuff, bro.”

There is no way in hell I’m going to tell him what it really is. Especially since my sister would read into shit and try to make it sound like it’s something more. Lord knows, she’d be chomping at the bit over the idea of me bringing a woman on a work trip. Probably start rambling on about relationships and love shit again like she did last summer at our Fourth of July getaway at Uncle Brad and Aunt Paula’s lake house.

Just the amount I’m checking my phone proves that this isn’t anything except having fun, because if it weren’t, I’d be running so fast in the opposite direction, the people from Guinness would hire a jet car to drive them along and catch up with me, just so they could record the new champion. Sophie has more than proven she’s a lot of fucking fun, and I’m eager for the opportunity for more.

Yeah, so much so that you haven’t thought about any other woman since she made her big debut at Club Craze…

I don’t have time to address that stupid thought because Rem is still staring at me with one quirked brow. His face downright calls me out, and I know I need to give him a little more or else he’ll just ride my ass for the rest of dinner.

“All right, fine,” I admit. “It’s half work stuff and half…” I grin and waggle my brows. “Other kind of stuff that I can’t say right now or else Mom and Winnie will get pissed at me.”

Winnie scoffs. “What’s the flavor of the moment’s name?”

Flavor of the moment?I almost laugh. Maybe people need to focus a little more on the woman sitting beside Ty at my mom’s dinner table. The redhead —Carrie?—has barely eaten anything and has said even less, and we all pretend like it’s just normal.

Yet they want to worry about Sophie Sage? Internally, I scoff.

“Mind your business, Win,” I respond to my sister, keeping it simple rather than hurting her feelings by repeating our mom’s earlier words, and she snorts.

“What?”That snort turns into an outright cackle. “If you’re starting to get all hush-hush with your weekly conquests, I’m going to think you’ve suffered a head injury somewhere along the line.”

“You say that like I’m always blabbing about my business.” I shake my head. “I don’t need to flap my gums. My mouth gets plenty of exercise in other ways.”

“Oh my God,” my sister counters and fakes a gagging motion with her finger. “Gross, Jude.”

“Do you do some form of oral calisthenics I haven’t heard of? Is it recommended by the National Board of Health?” Lexi asks, and that makes all the adults at the table, myself included, have to fight to keep a straight face.

“Definitely recommended,” Ty interjects, playing for my team for the first time during this meal. The woman at his side turns beet red, my mom looks to the ceiling—likely praying to God for salvation—and Winnie looks ready to inject some shit under my toenails and leave me to rot while she goes on with her life, having committed the perfect murder undetected.

“It’s basically just a…uh…well, it’s like writing cursive with your tongue,” Wes tries to smooth it over, but in reality, makes it a hundred times worse.

Remy, Flynn, Ty, and I all dissolve into full-bodied guffaws, and my mom turns to violence, smacking each of us who are within reach, one by one.

“Oh. Could I do it with numbers? I like writing numbers better.”

Winnie glares at me, and I shrug. It’s not my fault, really. I mean, fuck, how was I supposed to see this coming?

Desperate to move on, Winnie changes the subject bluntly. “Oh, before I forget! Lexi’s Mathletes competition is next Thursday night at her school. And we want everyone to be there, right, Lex?”

My niece nods. “Right.”

“Oh, that is so exciting, honey!” my mom comments and claps her hands together. “I can’t wait to see it!”

“I wouldn’t miss it, Lexi Lou,” I answer, smiling over at her as I finally dish some food onto my plate, and Rem, Flynn, and Ty respond with similar sentiments.

Finally feeling a little hungry thanks to the unexpected laugh session, I toss my first bite of spaghetti into my mouth. Simultaneously, my phone buzzes on the table, and despite the nosy-ass family members surrounding me, I check the screen to find a message that makes me smile so big, my fucking face starts to hurt.

Sophie: Okay. This is a crazy request, you realize that, right? Asking me to leave town and go to an unknown destination for two days with a guy I barely know?

Immediately, I type out a response and hit send.

Me: So is having sex in a public restroom, but hey, look how well that turned out. Also, I have too many pairs of your panties at this point to be called “a guy you barely know.”

Sophie: HA. God. Okay, hypothetically, if I say yes, when would we leave?

Me: I’d pick you up around 10 tonight.

Sophie: That’s in, like, three hours!

Me: In my defense, those three hours are like the last 3 of 48. I gave you the same amount of time as detectives have to find a missing person before they turn up dead! I’m not sure if you realize or not, but they have to do a lot of stuff in that amount of time, and with the number of episodes I’ve seen of that show, they’re successful like eighty percent of the time. Surely you can make a simple decision.

Sophie: Jude, you asked me right before you made me come inside a public bathroom at the Plaza. That’s grounds for a mistrial, at least.

Damn, I love when she gets all sassy like this. Even if we’re mixing jargon, they’re still some of the wittiest messages I’ve ever shared with a woman.

Me: I plead guilty, your honor. But I don’t really think you can convict me of anything other than satisfaction. I made you come TWICE, by the way.

Sophie: I’m so rolling my eyes at you right now.

Me: Well, I’d like to remind you that time is ticking, babe. Come have the time of your life with me for a few days and more orgasms than your body can handle OR…you know…stay in New York and do boring shit. It’s up to you. Take it or leave it.

I watch as the text bubbles on the screen float up and down. And I swear a good minute goes by without an actual response.

But then, one chimes in.

Sophie: Okay. Fine. This is NUTS. Pretty much insane. But count me in.

Hell motherfucking yes.

Me: You won’t regret it.

Sophie: Can you give me a hint on where we’re going so I know what I need to pack?

I smirk and type out one final response.

Me: Anything you want. Plus, lots of sexy panties. See you at 10.

I lock the screen of my phone and go back to eating dinner. Thankfully, everyone’s moved on to ribbing someone else, and they don’t have the energy to pay attention to me.

I smile.

Vegas, baby. With Sophie, her sexy panties, and her magically delicious pussy.