My Brother’s Billionaire Best Friend

by Monroe, Max

  Maybe: Yes.

  But before I can respond and successfully steer our dangerous conversation to safer territories, she sends another one.

  Maybe: Mexican takeout. Your place Tuesday night. And I have a surprise.

  Me: What kind of surprise?

  Maybe: If I tell you, it wouldn’t be a surprise, silly. You get the food (I’m a crunchy taco and chips and salsa kind of gal) and I’ll meet you at your place around seven.

  Me: You drive a hard bargain. But fine. See you Tuesday at 7.

  I send up a prayer that Maybe’s surprise isn’t showing me her wrong-day underwear. Because, fuck, I’m not sure if I’d be able to handle it.

  Please God. If anything, send Maybe to my apartment Tuesday in a parka.

  Maybe

  A little after seven, I make my way to Milo’s apartment building. It’s a large, sophisticated looking structure on Park Avenue, otherwise known as one of the richest streets in New York.

  Part of me wanted to strangle Lena for not telling me what DP was and encouraging me to text Milo instead. Because holy balls, it’s a little embarrassing I legit thought it meant some kind of double orgasm thing. But another part of me, the one that’s about to have a quiet dinner with Milo, is damned thankful for it.

  I can’t deny it was one of the catalysts that brought me right here—standing outside of his swanky apartment building.

  A doorman—yes, a fucking doorman—lets me inside.

  Once I give him my name, he leads me toward an elevator off the beaten path of the marble encased lobby and escorts me to the sixteenth floor.

  Per Gill’s update, “Mr. Ives is expecting you.”

  The instant I reach Milo’s floor, the elevator opens directly into his flipping apartment.

  He greets me in the foyer in bare feet, a pair of jeans, and a gray T-shirt.

  Hell’s bells, bare feet on a man has never looked so damn sexy before.

  “Exactly how rich are you?” It’s the first question that pops out of my mouth, and Milo smirks.

  “What makes you ask that?”

  I look around his place dramatically.

  Well, the entrance of his place. Which is damn near the size of my living room.

  “Because your building, your apartment…well, these are some swanky digs, Mr. Ives.”

  He groans. “You can go ahead and drop the Mr. Ives unless you want me to feel like an old man again.”

  I giggle. “Well, you are, like, six years older than me so…”

  He rolls his eyes. “Are we going to stand here and discuss my old age or head inside and eat some food?”

  “Hmm…” I tap my chin, but he doesn’t give me any time. Instead, he steps forward, tosses me over his strong shoulder and carries me through the foyer, down the hallway, and into the kitchen.

  “You can put me down now!” I shout through a giggle.

  Milo sets me on the expansive kitchen island and proceeds to grab some plates and cutlery for our food.

  “Would you like a glass of wine, Ms. Willis?”

  “Is it expensive wine?”

  He furrows his brow.

  “I mean, is it like a thousand-year-old wine that only rich people like you drink?”

  “No.” He snorts. “It’s a fifteen-dollar bottle of white I got at Duane Reed.”

  A laugh escapes my lips. “No shit?”

  “No. But it is somewhere in between the two. I have a lot of money, but I’m a pretty simple guy, Maybe.”

  “A simple guy with a driver and a doorman.”

  He laughs. “I never said I don’t enjoy some of the luxuries money can buy. But I don’t make a point to be extravagant in everything I do.”

  “I know.” I smile at him. “And I admire that about you.”

  “Yeah?”

  “Of course,” I admit. “I read an interview with you in the Times, and I was pleasantly surprised with your responses about living off ramen noodles and Kraft Mac & Cheese for the first few years of your company.”

  “I’ve forgone the ramen, but,” he says and opens the pantry, “I’ll never quit the occasional Mac & Cheese.”

  I snicker when I see no fewer than ten blue and yellow boxes of Kraft sitting on the center shelf.

  “Only a crazy person would quit Kraft.”

  “Exactly.”

  Together, we carry the wine, plates, and takeout bags into the living room and sit down beside each other on the couch.

  Once we’re both settled, and our plates are covered with delicious Mexican, he turns to me with a grin. “So…the surprise…”

  “What surprise?” I question. “There’s supposed to be surprise…?”

  He laughs. “You’re a terrible liar.”

  “Fine.” I grin and set my plate on the coffee table. “But prepare to be excited. You are in for the most enlightening night of your life. Do you have Netflix?”

  He nods and hands me the remote.

  It doesn’t take long before the opening credits of the Gilmore Girls are vibrating from the speakers of his flat screen hanging on the wall. I sing along to the song, and Milo glances at me in confusion.

  “This is the surpri—” he starts to say but stops when the title of the show is revealed on the screen—Gilmore Girls. “Wait…it’s a TV show?”

  I snort. “Of course, it’s a TV show.”

  “I thought you were talking about real fucking people.”

  “I wish I were talking about real people!” I exclaim and grab my plate. “Oh my God, if Stars Hollow were a real place, I’d move there quicker than you could say ‘Where are you going?’”

  When Lorelai and Rory start doing their Lorelai and Rory thing on the screen, Milo glances at me with a raise of his brow. “So, we’re going full-on chick flick kind of vibes tonight?”

  “You bet your sweet ass, we are.” I nod and take a big bite of my taco. “I mean, we’re not going to be able to watch all of the episodes tonight, but if we’re lucky, we’ll be able to get through the first half of season one.”

  “How long are the episodes?”

  “An hour or so.”

  “And how many seasons?”

  “Seven.”

  “And each season wouldn’t happen to be one episode long?”

  “Don’t be silly. There’re at least eight episodes per season.”

  Milo sighs and I giggle.

  “You’re such a Luke, it’s not even funny.”

  “Who is Luke?”

  I waggle my brows. “Oh, don’t worry, Mr. Grumpy. You’ll find out real soon.”

  I leave out the whole part that Luke Danes was my fictional man crush from the very first episode of the Gilmore Girls. Or the fact that Milo Ives was my real-life man crush from the time I was like ten years old.

  Yeah, let’s just leave out those minor details and enjoy the food and the company and the show.

  Two episodes into the Gilmore Girls and Milo throws the white flag.

  “All right,” he says and picks up the remote from the coffee table to put episode three on pause. “I think I need a little Stars Follow break.”

  I laugh. “Stars Hollow.”

  “Yeah. That,” he says and lies back on the couch like he’s been forced to run a marathon. “My eyes and ears just need a break.”

  I giggle again. “You want me to head out so you can get some sleep?”

  He shakes his head. “I fear if I go to bed now, I’ll dream about the fucking Gilmore Girls.”

  “You’re so Luke, it’s not even funny.”

  Milo glares at me. “I am not Luke.”

  “Oh yes, you are,” I retort and pick up a pillow from the couch to playfully smack against his chest. “You’re surly and cranky and grumpy. Exactly like Luke.”

  “I am not.”

  “Trust me, Milo,” I say with a little grin. “In your old age, you’ve grown into all of those things. Just face the facts, buddy. You’re no longer bad boy Jess, you’re Luke Danes now.”

  “Who the he
ll is Jess?”

  “You’ll find out in season three.”

  “I’ll have to watch it from the grave because I don’t think I can survive much more.”

  I giggle.

  God, he’s adorable.

  And sexy.

  And I can’t stop my eyes from moving up the length of his body. Up the denim covering his firm legs, over his zipper, over the barely visible lines of his toned abdomen.

  But my eyes take a detour and reroute themselves back to the zipper of his jeans.

  Back to the visible bulge beneath it.

  Back to the place that has me recalling the photo he sent me. Of him. In his boxer briefs.

  I’d be a liar if I didn’t admit I saved that photo and I’ve looked at that photo one too many times since he sent it to me. And I’ve fantasized about said photo even more.

  I’ve daydreamed about what he looks beneath the boxer briefs.

  About how big and thick he is.

  About what he would feel like hard between my hands. Heavy inside my mouth.

  Holy Kraft macaroni… Would he even fit inside my mouth?

  Pretty sure this is why deep-throating is a thing, Maybe…

  I don’t know anything about deep-throating—or blow jobs, for that matter. Never even done it before. But fuck, I’d want to give it a shot. With Milo.

  “Having Gilmore Girls withdrawals already?” His voice pulls me from my thoughts, and I look away from the zipper of his jeans to his blue as the sky eyes.

  “Huh?”

  “I lost you for a minute there,” he says with a small smile. “Where did you just go?”

  Uh…to you and deep-throating and your penis and deep-throating your penis.

  “Yeah…uh…” I pause and dig my teeth into my bottom lip. “I probably shouldn’t say.”

  He tilts his head to the side. “What were you just thinking about?”

  My cheeks flush red. I don’t respond.

  “Maybe?”

  “How do you deep-throat?” I blurt out the question, and Milo’s eyes go wide.

  “What?”

  Screw it. I mean, I asked him about DP the other day. What’s the big deal about asking him about blow jobs too?

  The big deal is probably because you weren’t just thinking about blow jobs, you were fantasizing about giving him a blow job…

  “Am I supposed to deep-throat?” I ask. “You know, like, when I’m giving a…you know…am I supposed to deep-throat? Do most guys expect that?”

  His jaw goes unhinged for a brief moment, but he quickly recovers. “Well, I think that depends on the guy, Maybe.”

  “Do you like deep-throating?”

  “I like whatever feels good to the woman,” he responds without a second thought. “The only thing I don’t like is for a woman to give me a blow job because she feels obligated or like she’s supposed to. I want her to want to do it. I want her to enjoy it as much as I enjoy it.”

  “I’ve never given a blow job,” I whisper, and his eyebrows rise.

  “Really?”

  I shake my head. “I mean, I’ve touched a penis before with my hands.” I gesture awkwardly in a showy jazz motion. “But I’ve never actually given a blow job.”

  “Is there a specific reason for that?”

  “Not really.” I shrug. “I guess it just never felt right. I never felt comfortable enough with the guy to do it.”

  “That’s not a bad thing, Maybe,” he says with a soft smile across his lips. “I really admire you for waiting until it feels right.”

  “Seriously?”

  “I wouldn’t lie to you, kid.” He holds out his arms. “Come here,” he says, and I lie down beside him on the couch.

  Milo runs his fingers through my hair, and I rest my head against his chest.

  And God, his strong body against mine feels so good.

  Just so incredibly good.

  Instantly, I start to throb between my legs.

  Fuck. I’m attracted to him. I’ve always been attracted to him. Even when I was a teenager and didn’t really understand what it was I was feeling whenever he was around.

  I want him.

  I want to explore his body with my fingers and lips and tongue.

  I want to know if his cock feels silky and hard between my hands like I’ve imagined.

  Or if he’ll actually feel heavy inside my mouth.

  Stop overthinking, then. Just do it. Find out the answers for yourself.

  Before I can second-guess it, I slide my body down his and rest my face right beside his zipper. Hesitantly, I lift my hand and place it right over the bulge of his jeans.

  “Maybe?” he asks, his voice quiet but undeniably raspy with arousal.

  I ignore him and move my fingers to the button and zipper of his jeans. They’re undone a few seconds later, and I can’t stop myself from sliding my hand beneath the waistband of his boxer briefs until I can feel his cock against the palm of my hand.

  He’s hard and getting harder.

  And he’s big. And thick. And perfect.

  And now I want to see him.

  Taste him.

  Wrap my mouth around him.

  And I don’t hold back.

  Instead, I pull a Nike and Just Do It.

  Milo

  My cock is in her hands.

  Her petite fingers grip me at the base and move up and down in a gentle, hesitant motion.

  I’m hard, so fucking hard, I’m certain my dick could hammer nails.

  “Maybe?” I say her name again, but she doesn’t respond.

  Instead, she looks up at me from beneath her lashes and searches my eyes for a long moment. But her hands, well, they keep touching me, caressing me, stroking me.

  “I want to know what it feels like,” she whispers. “I want to know what it feels like to make a man feel good.”

  This is a bad idea, Milo. A bad fucking idea.

  “I don’t think this is a—” I start to say, but when she leans forward and wraps her perfect little mouth around the head of my cock, all rational thought flies out of the fucking room. Out the front door. Out of the damn city.

  Her mouth is warm and soft and so insanely perfect, I have to bite back the groan that threatens to escape my throat.

  “I’ve never done this before,” she whispers, and uncertainty fills her brown eyes. “Tell me what makes you feel good.”

  “I can assure you, anything you do right now will feel good.”

  Because it’s the truth.

  It’s a fucking certainty.

  In my eyes, anything she does will be perfect. It’s a fact when it comes to her.

  She slides herself down my body so she’s between my thighs, and all I can do is watch her as she wraps her mouth around me again. Her long locks create a veil around her face, and I reach forward to brush the rogue strands behind her ears.

  With her hand gripped around my shaft, she moves her mouth up and down my length. But her tiny mouth can only take so much, and the mere idea of that only makes me harder.

  “There is more cock than mouth, sweetheart.” I reach forward to brush my fingers across her lips. She starts to hesitate, but I add, “It’s fucking perfect. What you’re doing is perfect.”

  You’re perfect.

  My words encourage her further, and the way her eyes glaze over with satisfaction and confidence has my heart beating harder and faster inside my chest.

  I watch the way her legs fidget beneath her. Her thighs clenching, her hips moving from side to side. I take in the way her shirt falls forward, revealing the soft curves of her breasts. And I’m riveted by the way her pretty little lips look wrapped around me.

  She is beautiful and timid yet assertive and seductive.

  She is sex and innocence, a fucking goddess before my very eyes.

  The tip of her tongue moves up and down my length, and my thighs tighten with pleasure. My eyes glaze over as I watch her explore me. Taste me. Suck me. Her fingers grip and stroke, and her fingertips care
ss me.

  A moan escapes her throat, vibrating against me, and the movement of her hips becomes more apparent.

  She’s turned on. Craving. Wanton. Turning more aroused by the second.

  Fuck, it’s nearly too much for my brain to process.

  And it’s most definitely too much for my dick to handle.

  My climax hits me hard, starting at the base of my cock and spreading throughout my whole damn body.

  My heart pounds inside my ears and my breaths come out in erratic pants, and Maybe stays with me through the whole thing, her soft mouth wrapped around me, swallowing my orgasm through soft moans.

  It’s the best fucking orgasm I’ve ever had in my life.

  And it’s not because of what she did.

  It’s because it was her lips wrapped around me.

  It was her eyes locked with mine.

  It was her moans in my ears.

  It was her hands on me.

  It’s because it was Maybe.

  And you tried to say you weren’t falling for her…

  Maybe

  I step off the subway and head up the stairs and toward my fate.

  Well, seeing as I still have another two hours before my interview with Taylor McHough at Beacon, not directly toward my fate, but that’s minor semantics.

  I’m two blocks away from the building where Beacon House headquarters reside, and I can’t find the strength to finish the job.

  I’m pacing. On the sidewalk. While fellow pedestrians bitch and moan and maneuver around me.

  But I’m too lost in my own head to care.

  In a few hours, I will be in the middle of what is the biggest interview of my life.

  The pressure is suffocating.

  God, what am I going to do until then?

  I can’t just stand here pacing like a lunatic. No doubt, someone will call NYPD with a complaint of a deranged woman if this goes on any longer.

  With a sigh, I turn on my heels and head in the opposite direction, four blocks east and another two blocks south and don’t stop until I’m standing directly in front of Fuse’s office building.

  If anyone can understand my current insane state of mind, it’s Milo.