My Brother’s Billionaire Best Friend

by Monroe, Max

  “You adorable little hussy!”

  I fall face first into my palms, and she puts her hands on my shoulders and shakes them consolingly.

  “If you enjoyed it that much, I can guarantee he enjoyed it too.”

  “How in the hell do you know?”

  “Because phone sex, text sex, any kind of virtual sex, is the ultimate two-way street. None of it is tangible, it’s all imagination. In order to say things to you that get you excited, he has to be able to see them in his mind. And if he sees them in his mind, I promise you, as a male member of the human species, he was feeling them in his dick. He probably wanked himself to all manner of thoughts of you right after you guys were done.”

  Milo masturbated to thoughts of me?

  Holy. Shit. My cheeks flush again, and Lena doesn’t miss a beat.

  “Yes, friend,” she says, and her full lips turn up in a knowing smile. “And guess what? Because of last night, you just successfully put yourself into your crush’s fantasies.”

  It’s nearly too much to process.

  She grins. “Have you spoken to him today?”

  I shake my head.

  I mean, I’ve almost texted him at least fifty times, but no, I haven’t actually texted him.

  Nothing seemed quite right.

  Thank you for the orgasm last night!

  You’re a great sexter!

  How ’bout that sexting last night? Pretty awesome, right? Want to do it again tonight?

  Delete. Delete. Delete.

  But, seriously, what do you say to someone after that?

  Fuck if I know.

  But apparently, Lena does.

  “Phew.” She lets out a giant breath from deep down in her lungs. “Okay, that’s good news.”

  My eyebrows draw together, rife with skepticism. “Why is that good news?”

  “Because your next text to him cannot, and I mean cannot, be about sexting or anything remotely involving what happened last night.”

  Jesus Christ. Why does everything I learn about dating seem like it adds a side to an already impossible-to-solve Rubik’s Cube?

  “Then what in the heck do I say?”

  “Something really boring and mundane. You need to make him feel like last night was no big deal in your mind.”

  The first thing that comes to mind is the email Cassandra Cale sent me this morning. Evidently, I wowed her yesterday—so much so, she didn’t waste any time offering me a job.

  “Well…Rainbow Press sent me a job offer… Will that work?”

  Lena’s face lights up. “That. Is. Perfect.”

  “Okay, so I’ll text him and let him know about the job offer.”

  Easy peasy.

  “Ah, ah, not so fast, honey,” she responds with a devious smile. “First, the job offer. Then, you’re going to make him sweat a little.”

  Make him sweat?

  “What?” I tilt my head to the side. “You want me to work out with him?”

  “No.” She damn near cackles. “Not actually sweat, but metaphorically sweat.”

  I furrow my brow. “I’ll be honest, you lost me back on sweat. I truly have zero clue what you’re talking about at this point.”

  “It’s all very simple,” she says and briefly glances over her shoulder to watch Winston rise from the sleeping dead, toss his empty cup into the trash, and walk out the door without uttering a single word.

  “You need to make him feel like whatever happened last night is no big deal. Now isn’t the time to be a stage-five clinger. Now is the time to put yourself out there with other men and make it clear to him that you’re not just sitting around and waiting for him to make the next move.”

  “And how exactly do I do that?”

  “Did you download TapNext on your phone?”

  I cringe. “Not yet…”

  “Jesus,” she mutters and holds out her hand. “Give me your phone.”

  “What?”

  “Give me your phone, Maybe.”

  On a sigh, I unlock the screen and hand it to her.

  It takes ten minutes, but by the time I leave the coffee shop to head back to Bruce & Sons, TapNext is downloaded on to my phone and Lena has set up an entire dating profile for me. Bio, photo, the whole-fucking-shebang.

  When I go into the back room to put my apron back on, my nerves get the best of me, and I send a text to Lena.

  Me: I don’t think I really want to date random guys I meet on TapNext.

  She texts back immediately.

  Lena: Don’t panic. You’re only using it for one date.

  Me: One date? You went to all that trouble making the profile for one date?

  Lena: Yep. It’s all you’re going to need. You’re going to go through your matches and find a nice guy who looks like you’d be able to suffer through a dinner with him.

  Me: You’re a complex woman, Lena. And I don’t understand you one bit.

  Lena: Just trust me, okay? You’re not really going to date the guy. You’re just going to make Milo think a bit. Because before you officially go on your date, you’re going to send Milo a few text messages asking him for “advice” about your date.

  Me: This sounds suspiciously crazy.

  Lena: Because it fucking is. But it’s also going to work.

  I can’t decide if she’s giving me the best advice I’ve ever been given or if she’s sending me on a seriously scary journey that’s going to end in disaster.

  Another text of additional reassurance comes in from her just as I need it. The timing is so perfect—I was a literal second away from completely losing my shit—I’m hoping maybe, just maybe, it’s a little bit of a text from God too.

  Lena: I promise you, it’s all going to work out better than you can even imagine.

  Better than I can even imagine?

  I’ll settle for good as long as it’s not too good to be true.

  Milo

  After a long-as-hell workday, I leave the office and head to the gym.

  It’s Friday. The weekend is here. And I’m going to do everything in my power to avoid the office and my emails until Monday morning.

  Sadly, I tell myself this every Friday evening, but here’s to hoping I actually follow through this time.

  I step into the lobby of the gym, and the sounds of chatter, music, and the clinking and clacking of weights fill my ears.

  The young girl behind the reception desk nods her recognition and buzzes open the doors that lead to the main area of the gym.

  It’s busy for a Friday evening, but after a quick change in the locker room, I manage to snag a treadmill on the second floor and start my workout off right with some cardio.

  With Rage Against the Machine playing through my earbuds, I turn up the speed and dive straight into the session.

  But twenty minutes into my run, the screen of my phone lights up inside the cupholder, and my attention is officially pulled to the exact place it shouldn’t be. The exact place I’ve been trying like hell to avoid for the past week.

  Maybe: I need your help.

  I look up from her message and meet my reflection in the floor-to-ceiling mirrors of the gym to find myself smiling like an idiot.

  Shit. I cringe at my absurd reaction to seeing her name in my inbox.

  It’s been five days since Maybe innocently tricked me into a sexting conversation that went way too far, and every-fucking-night since then, I’ve woken up smack-dab in the middle of all sorts of explicit dreams about her.

  It’s all completely fucked.

  She’s my best friend’s little sister. And one-hundred-percent off-limits.

  Yet I can’t stop trying to picture what she looks like when she comes.

  And Evan was worried about Cap helping Maybe out…

  Son of a bitch.

  Maybe: Earth to Milo. Come in Milo.

  On a sigh, I type out a response and offer up a silent prayer that she’s still just overthinking the whole Rainbow Press situation.

  Me: Kid, I already told
you. There is no need to feel guilty about not accepting the Rainbow Press job. Cassandra Cale isn’t mad. She knows it’s not personal. It’s business. And, honestly, she’s probably still holding out hope you’ll end up reconsidering after you interview with other publishing houses. She doesn’t know what I know about Beacon’s track record for jumping on her prospects, but they don’t know you’ve already declined her offer either. This is a case of “what they don’t know benefits us.”

  In between all of my insane fantasies about Maybe, I’ve still been the guy on the publishing industry sidelines, helping and reassuring her that she’s making the right moves.

  At least you’re still managing to do the one and only thing Evan asked you to do…

  Yeah. Fuck. At least I’m still doing that.

  Maybe: I appreciate that, but it’s not the help I need. This has nothing to do with business, Billionaireman.

  Me: I’m not sexting with you again.

  Good God, you idiot. I groan two seconds after I hit send and see my far-too-inappropriate words populate in our conversation.

  Apparently, it seems I just can’t help my-fucking-self when it comes to her.

  Maybe: HAHA very funny. Not that kind of help. I need advice for a date.

  Me: A date?

  She’s going on a date?

  I nearly trip over my own fucking feet, and instantly, I tap the console on the treadmill several times until the speed slows down to a leisurely jog.

  Maybe: I have a date tonight with someone I met on TapNext.

  Me: Seriously?

  Maybe: Why would I lie about something like that?

  Me: When did you meet him?

  Maybe: Yesterday.

  Me: You’re going on a date with a guy you met online yesterday?

  Maybe: Yes, Billionaireman. Keep up. Aren’t superheroes supposed to have unparalleled cunning, strength, and wit?

  I scowl.

  What in the ever-loving hell? Has she lost her mind?

  Maybe going on a date with some random stranger sounds like the worst idea I’ve ever heard.

  Me: Do you even know anything about this guy?

  Maybe: I know his name is Jess. And, not gonna lie, I love the name Jess because of the Gilmore Girls. I’ve been 100% Team Jess since the instant he stepped foot in Stars Hollow.

  I furrow my brow. Should I know these women?

  Me: Who are the Gilmore Girls?

  Maybe: YOU DON’T KNOW WHO THE GILMORE GIRLS ARE??

  Me: Do they live in New York?

  Maybe: Oh my God! I don’t have time to get into all things Gilmore Girls with you, but one day, I will enlighten you. Right now, this date is my priority, and I have no idea what I should wear. Help. Me.

  Me: You mean your date with a potential serial killer is your priority.

  Maybe: He’s not a serial killer!

  Me: How do you know? You’ve only known him for 24 hours via a dating app. He could be a serial killer…or at the very least, a catfish.

  Maybe: Pretty sure the length of time you know someone doesn’t help deduce whether or not they’re a serial killer. I mean, Jeffrey Dahmer’s family knew him his whole life, and they had no clue. Ted Bundy’s wife didn’t know either.

  I sigh. Always the sassy smartass…

  Me: And that reasoning is supposed to be reassuring how?

  Maybe: Don’t rain on my date parade, Milo. Just help me. Tell me what is appropriate first-date attire.

  Me: Pretty sure you’re supposed to consult girlfriends for this kind of advice.

  Maybe: But I don’t want a woman’s advice. I need a man’s advice. I’m sending you three options. Be honest. And flipping stop thinking about serial killers and tell me which outfit is the best choice.

  Thirty seconds later, three photos upload inside our conversation.

  Hesitantly, I open the first one.

  It’s Maybe standing in front of her bedroom mirror with a pile of clothes sitting on her bed and several shoes strewn across the floor behind her. Her long brown locks are tossed up into a messy bun, and an uncertain smile shapes her full pink lips. Her body is clad in a little black dress, and nude stilettos cover her petite feet.

  She looks good. Too good.

  Option one is not the right choice.

  Option two is more of the same. A short, floral summer dress that rests a little too high on her thighs, and the pale pink heels on her feet only add to the elongation of her toned legs.

  Nope. Not that one either.

  The last and final photo is more laid-back and the clear best option of the three. Jeans, a little white blouse that shows just a slight hint of her lower stomach, and a pair of flats.

  I waste no time at all in giving her my choice.

  Me: The jeans but with a different shirt.

  Maybe: What? Why? I thought the white blouse was cute. It’s fun and flirty.

  Me: It shows too much.

  Maybe: You’re nuts! It doesn’t show anything. Maybe I should just wear one of the dresses.

  No. Way.

  With the things I’m thinking about doing to her in those dresses, I can only imagine what some low-life catfish will be thinking about doing.

  Me: No. Definitely the jeans.

  Maybe: Fine. Jeans it is. But I’m sticking with the blouse. Thanks for the advice!

  I should end the conversation, but I literally can’t. The phone is attached to my hand permanently now and will forever be a part of my body. At least until she’s home from the date, that is.

  Me: When is he picking you up?

  Maybe: I’m meeting him at a restaurant in Greenwich Village.

  I almost chastise the bastard for not picking her up for the date, but then I realize it’s a good fucking thing he isn’t going to see where she lives.

  Unless she decides to take him home…

  Me: Are you planning on bringing him back to your place for a nightcap?

  A nightcap? For fuck’s sake, I sound like my dad.

  Maybe: A nightcap? LOL. If you’re asking me if I’m planning on some kind of first-date hookup, I don’t know. I guess I’ll just see how the night goes.

  Oh God. I do not like that response.

  Me: Just be safe, okay?

  Maybe: You got it, dude.

  Two seconds later, a Michelle Tanner GIF with a thumbs-up populates under her message.

  Maybe: And you be safe too.

  I furrow my brow. What is she talking about?

  Me: Safe doing what?

  Maybe: I don’t know. I figured you probably have a big night out planned with one of your “friendly” lady friends.

  I’m equal parts amused and terrified at where this conversation could lead.

  Me: Here we go again.

  Maybe: HA. I could have said fuck buddies, but I was trying to be cognizant of your delicate sensibilities.

  Me: Smartass.

  Maybe: So, you DO have a “this is not a date” date tonight?

  Four minutes ago, I had nothing going on. Paperwork, Netflix, and a bottle of scotch to smother the inappropriate fantasies about my best friend’s sister. But now that she’s going out, I can’t stay home. I’ll lose my fucking mind.

  Me: I have dinner with a friend, yes.

  Maybe: A friendly lady friend.

  Me: I can confirm it is a woman.

  Maybe: A fuck buddy.

  A laugh bubbles up from my lungs. I knew she could only hold that in for so long.

  Me: Jesus.

  Maybe: LOL. All right, I’m going to go get ready for my date. I hope you have fun on your non-date date tonight.

  Me: Thanks. I really hope your TapNext date isn’t a serial killer, but I’ll make sure Bruce creates a nice arrangement for the funeral if he is.

  Maybe: LOL. Very funny. Goodbye, Milo!

  When our conversation comes to an end, I feel…uncomfortable.

  She’s twenty-four years old. She should be going on dates. She should be putting herself out there.

 
This is a good thing for her.

  It just doesn’t feel good for me.

  Truthfully, it doesn’t feel so good at all.

  Now I have to figure out something to do.

  After scrolling quickly through my contacts, I text Senna Flick, a friend who’s been a casual monthly fling for the last two years. Where I’m busy running Fuse, she’s busy traveling around the world doing marketing for a wealthy media conglomerate that owns two major television networks and produces movies on the side for a popular online streaming website. Getting together has always been uncomplicated and mutually beneficial.

  No-strings-attached sex and sufficiently intelligent company.

  Tonight, as a whole, feels different, but the text exchange is simple, just as it always is.

  Me: Dinner tonight?

  Senna: I’ll be ready at 8.

  I sigh when I read the text but do the nice, gentlemanly thing and type out a response.