Dating the DILF: A Single Dad Romance

by Amali Rose

  “I most definitely am.”

  “Excellent. Pick her up at seven. She’ll text you her address.”

  “Are you two done planning out my personal life?” Charlie asks in exasperation and Adelaide and I grin at each other.

  “Yep,” we both agree.

  “Right, I’m so glad you guys have sorted that out, now, Charlie, I have an important question and I need an answer because it’s been bothering me ever since Miles told me about it.” We all look at Gray, the girls with curiosity and me with dread. He smirks back at us.

  “Really, how is your pussy?”

  I zip up my makeup bag and give myself a final once-over in the bathroom mirror, once again cursing the terrible bathroom lighting. I really should do something about that.

  My heart is hammering nervously, and I check my phone for the time. Ten minutes until Miles arrives.

  The last few weeks have been wonderful. While we haven’t had a lot of opportunities to see each other, we have spoken or messaged daily and I have a feeling we are beyond the point of no return. Meeting Lulu so early was a shock, and if I think about that night, I can still feel the terror that overwhelmed me when I first laid eyes on her. I’m not sure how normal it is to be so scared of a toddler, but that two-foot-tall, blonde-haired, blue-eyed angel was pretty much my worst nightmare.

  Miles has also since admitted that he was nervous, which doesn’t surprise me. There’s no denying that if Lulu hated me, which I had fully expected, whatever this is between us would have been over.

  Thankfully, that wasn’t the case and I’m pretty sure I sealed the deal when I heard her whisper a quiet sit, which I have no doubt was meant to be shit, when she spilled her water on the sofa. Keeping my mouth shut probably wasn’t my finest adulting moment, but a prospective girlfriend has to do what a prospective girlfriend has to do.

  Once I have tidied up the bathroom, I pull my phone out, fully intending to check the time again, but instead I pull up my texts and find my thread with Miles.

  Reading back over our messages evokes a swirl of emotions within me. There are the usual nerves I feel when getting to know someone new, alongside the fear I associate with opening myself up to someone. The anxiety that worms its way into my brain, reminding me that one day, whether it be a week from now, or a year, he will walk away. Because I am a ruiner and I destroy everything I love.

  But lately, there has been something else. Something that has been driving me through the apprehension and coaxing me through my misgivings.

  Hope for a future I never thought I was built for.

  I let my eyes linger on the messages I received earlier this afternoon and my pulse picks up, thrumming loudly in my ears.

  Miles: Dad is taking Lulu for the night, so I have no curfew.

  Miles: Did you hear that? It was my freedom war cry lol

  I never replied. I wasn’t able to think of anything that would be sufficiently flirty, so I went with silence. You can’t go wrong with silence, right?

  Oh, God, how is it possible to be this bad at dating?

  The sound of the doorbell snaps me out of my internal hatefest and I race down the stairs as fast as my heels allow. Taking a moment before I open the door, I take a deep breath and release it slowly, hoping it will settle my nerves.

  When I open the door, a heavy silence sits between us. What was I thinking earlier about silence being bad? Because there’s nothing bad about this. It’s loaded with heat and bursting with a ferocity I have never experienced before.

  “Wow.” He breaks the silence and a flush colors my face.

  He’s standing on my front porch with a look of appreciation on his face and I wonder if he can see that same appreciation reflected back. Because Miles in a suit is a sight to behold.

  From the navy-blue blazer that fits his broad chest and shoulders impeccably, to the shiny black oxfords on his feet, he is picture-perfect deliciousness.

  He leans down and places a kiss just below my ear and the spicy notes of his aftershave hit me at the same time as his lips. It’s enough to make a girl weak at the knees.

  “You look incredible.” His hand is still holding on to my arm, his fingers curled around my elbow. Are elbows an erogenous zone, because it’s feeling pretty damn sensual right about now.

  Trying to stop that train of thought, I smooth my hands over my red sheath dress. “Give me one second, I just need to grab my clutch.”

  He steps into the entrance and my little gray furball appears from nowhere and begins winding its way between his legs. Miles bends down to pick him up.

  “That ear healed up well.” He nuzzles the cat.

  “It did, and he was so good while it was healing.”

  “She.” Miles chuckles.

  “Oh, right, she.” I roll my eyes. “So, I finally decided on a name,” I call out, heading into the kitchen to grab my bag.

  “Jesus, it’s about time. What did you go with?”

  I quickly open my clutch and slide my phone inside, making sure I have some cash, my debit card, and my ID.

  “Mintie.” I walk back into the entrance to see Miles looking at the photo of my grandparents I keep there. “It seemed appropriate when I busted him eating from my bowl of ice cream last night.”

  I step toward him and lean down to place a kiss on Mintie’s head, and when I look up, I am only inches away from Miles. He takes advantage by brushing a kiss against my mouth.

  His hand lands on my waist and slides down to settle on my ass, grabbing a handful of my butt cheek. A jolt of heat rushes through me and I step even closer, pressing my body to his, and thread my hands through his hair. He deepens the kiss, and in a moment of clit-aching perfection, sucks lightly on my tongue before pulling back to nibble along my bottom lip.

  I can feel him harden against my stomach and for the first time in my life I’m ready to throw out the rules and blow off my responsibilities. I am about to suggest just that when there is an angry hiss between us, and we jump apart.

  Mintie leaps from Miles’ arms and stalks off, throwing a look of disdain back at us.

  Miles clears his throat and looks at me in amusement. “I guess we should get going?”

  The distance has done its job and cleared my head, so I nod, not trusting my voice right now, and as I lock up and follow Miles to his car, I let my mind wander to how the night might end. Or more specifically, how I hope it will end.

  “I thought you didn’t like peopling?” Miles’ deep voice questions.

  We’re walking through the vast ballroom of a downtown hotel, where my firm is holding its annual client gala. The night has managed to be both draining, as these nights usually are, and absurdly wonderful all at once.

  “I said I didn’t like it, not that I wasn’t great at it.” I lean into his solid form and take a sip of champagne.

  His arm winds around me, his hand settling on my waist and he gives a gentle squeeze. “You’d never know. You’re working the room like you own it.”

  “It will take me a week to recover from all this,” I assure him. “Poor Addy will have to run interference so I have to talk to as few people as possible.”

  “I’m surprised she’s not here.”

  I’m momentarily distracted by Tiff Klein, the wife of one of our biggest clients, whose gaze is fixed on Miles, her nose slightly wrinkled in a look of distaste.

  It has been an ongoing theme tonight. The women in the room have definitely been taking note of his appearance and while, in general, it has been a pervasive sense of subtle curiosity, I have recognized a few ladies looking with either fierce interest or deep hostility. It has me slightly on edge.

  “These events aren’t mandatory for assistants.” I force myself to ignore Mrs. Klein. “It’s strongly encouraged that they attend, but it’s Addy’s mom’s birthday today, so she’s having dinner with her family.”

  His grip on me tightens and he leans down, his lips finding my ear. “I’m glad I could be here with you tonight, then.”

/>   How does he know? How does this guy that I have only known for a month seem to understand me as well as he does? Because I can do this thing tonight. I can absolutely come in with my game face on and I can impress every single person who needs to be impressed. But every second is filled with anxiety, and if I had had to do this alone tonight, it would have seemed insurmountable.

  “I’m glad too.”

  “Charlotte.” My boss appears suddenly in front of us, startling me, and I take a step away from Miles as I remember I really should entertain some decorum considering where we are. Despite the free-flowing alcohol and all the schmoozing, this is essentially a night at the office.

  “Kendall,” I greet her. “Miles, you remember my boss, Kendall Harris.” He nods at her with a polite smile, which she does her best to return, but her face is taut and filled with tension.

  “Charlotte, David Brennan is insisting that the draft of the contract be emailed over to his partner now.”

  I know the contract she’s referring to. A team of us spent today locked up in a hotel room with Mr. Brennan negotiating the finer points of the agreement.

  “I thought we were going to finalize it tomorrow and send it through?”

  “So did I.” Kendall’s lips purse. “Apparently he wants his business partner to review it before we go any further.” She shakes her head in annoyance. “Would you mind running up to the room and emailing it through?” She hands me the room key. “Send it to their corporate office in LA. The number is on the contract.”

  “Of course.” She’s moved on before I can say anything else, so I turn to Miles and offer him an apologetic smile. “I’m sorry.”

  “Don’t worry about it.” He takes my hand, entwining our fingers. “Lead the way.”

  “Are you sure? I don’t mind if you would rather wait at the bar? I won’t be long.”

  “I’d rather be with you.”

  I search his eyes for any sign of annoyance at this disruption, but I find none.

  “Okay, let’s get this over with and then the next round of drinks are on me.”

  “It’s an open bar, Chicago,” he counters wryly.

  “Jeez, appreciate the gesture, will you.” I roll my eyes at him and start for the elevators, but I come to a sharp stop when Miles fails to move.

  I turn, confused, and Miles’ eyes, which only moments before were playful, are now watching me earnestly. He takes a step closer and drops my hand, lifting both of his to cradle my face.

  “I appreciate everything about you.” And he presses a kiss to my lips that has my thighs clenching together in an effort to control my altogether inappropriate response to his mouth on mine.

  Pulling away, he maintains his hold of me and slays me with a wicked smirk.

  “C’mon, let’s see what trouble we can find in this hotel room.”

  He stalks off, pulling me behind him as a throb pulses through my core at the promise his words hold, all thoughts of decorum and etiquette vanishing.

  The hotel is humming around us, the air thick with the heady anticipation of a Saturday night as people make their way through the palatial lobby.

  Miles hasn’t said a word since he pulled me from the ballroom, and my mind is working overtime, playing his words over and over.

  “What floor?” His resonant voice pulls me out of my head.

  “Hmm?”

  “Which floor are we going to?” Bemusement colors his words.

  “Oh, fifteen.” I clear my throat and ignore his smirk.

  Nothing is going to happen, I tell myself. That would be the height of inappropriateness and… and it would just be so wrong!

  “You’re looking a little flushed there, Charlie. You okay?” Miles is watching me with a look that tells me he knows damn well what is going through my mind right now.

  “Fine.” I keep my answer short and sweet since I seem to be experiencing some difficulty controlling my breathing.

  “If you say so.” The smirk is still there, a dirty salute to promises begging to be kept.

  I’m just not sure who will be doing the begging.

  He turns his attention to the display above the doors, watching the numbers rise.

  I should make something clear. I am, by no means, a prude. I love sex and I’m a firm believer that an orgasm a day keeps the stress at bay. But—but, not butt, that is a no-go zone, sorry, boys—I’m the first to admit, I’m not the most adventurous in that area and I have never been with anyone who wanted to experiment.

  In college it was clumsy fumblings, get it in and out before a roommate walked in on us. And, after? Well, there hasn’t actually been many after. Relationships never worked out well for me. There was too much drama, too much turmoil. When I discovered my first post-college boyfriend was cheating on me, I was devastated. When I discovered that he was cheating on me with his girlfriend and I was actually the other woman, I was livid. I found myself wallowing in bed, wavering between heartbreak and hatred with a pint of ice cream and a bottle of five-dollar wine. Sucking down that wine in a bed strewn with dirty tissues and melted ice cream all over the sheets was the moment I realized history was repeating itself. How many times had my mother locked herself away, crying over some idiot who had broken her heart, only to dust herself off and find herself in exactly the same situation months later.

  I decided right then that wasn’t going to be me. Those emotional extremes that only served to remind me of my turbulent childhood weren’t what I wanted. Stability and balance was what I needed to find my peace, and that is what I crave more than anything.

  So, why am I standing here next to a man who is everything I shouldn’t want and, instead of running away, I’m desperate for him in every way.

  I want to break every one of my rules for him and with him. I want that strange, little, cussing human of his to like me, because she came from him and every part of him is important to me. Even the parts that terrify me.

  The elevator doors ding open and we both step out of the small space. I turn to head toward room 1514, but Miles stops me, taking hold of my wrist lightly.

  “I would never expect you to do anything you don’t want to. You know that, right?”

  His thumb is rubbing slow circles over the tender flesh of my wrist and he’s looking at me so sincerely. I know he’s being honest, and I don’t have a moment of doubt that, while he may push my boundaries in many different ways, he will never exploit my trust.

  “I know.”

  “Good, because it was just a stupid joke. Our first time together isn’t going to be during a few stolen moments at your work party.” He places a kiss on my forehead, then moves his mouth to my ear, lowering his voice to a husky whisper. “We’ll need all night for everything I have planned. Now…” Taking a step back, he nods in the direction I was heading. “This way?”

  Ignoring the flush of disappointment that courses through me—what is wrong with me?—I murmur a quick affirmation and a few minutes later we are entering the hotel room.

  “I’ll just be a minute. Grab something from the minibar if you want, no one will ever know.” I race to the large mahogany desk on the other side of the room, and using an app on my phone, I quickly scan the document I need and email it.

  Duty done, I turn back to Miles, eager to get back to the party and enjoy the rest of the night.

  He’s standing in front of the full-length window that spans an entire wall of the room, his eyes glued to the view. The city below us is lit up and glowing. It’s truly a sight to behold.

  “It’s so beautiful.” I move to stand next to him.

  “It is,” he agrees, but when I look up at him, his eyes are no longer on the vista below us.

  I want to kiss him. I want to do a lot more than kiss him, but it seems like a good place to start. So, just like with everything else involving this man, I give in to the urge and take hold of his lapels, pulling him down until we are eye to eye.

  “Don’t let me regret this.” It’s a plea, for more than just thi
s moment, but a pointless one. I couldn’t stop any of it from happening, even if I wanted to.

  And, let me make it very clear. I don’t.

  His eyes dance over my face, as if reassuring himself of my intention and then his mouth is on mine, his tongue licking along my bottom lip, seeking entry. I open for him, ready to taste him. I’m desperate to feel his tongue, his mouth, on every inch of my flesh and I wrap my arms around his neck, pulling him closer, as close as I can get.

  He turns us around, pushing my back up against the window and pressing the length of his body into me, until I feel the obscene thrust of his cock against my stomach. The need to grind my body against his is urgent and consuming, and when I hear the low growl he emits, I do it all over again.

  His hand threads through my hair and he pulls back sharply, exposing the curve of my neck to his greedy mouth. He bites and sucks, using his tongue to soothe the sting.

  “Are you sure?” His lips move against the skin of my throat and it tickles. I try to find a way to tell him I have never been more sure of anything in my life, without actually saying the words, because he has rendered me speechless right now.

  Instead, I simply nod and begin undoing the buttons on his shirt, but he stops me and takes a slight step back.

  We hold each other’s gaze, while my heart thuds against my chest. I know what he’s doing. Giving me a moment to gather myself, free of his touch, to be sure of the decision I’m making.

  Don’t let me regret this.

  I twist my arm behind my back and slowly lower the zipper, being sure to hold his eye the entire time, and then let my dress fall to the ground.

  He grits out a guttural groan at the sight of me, completely naked but for my stilettos, and he doesn’t hesitate to move forward and press himself flush against me.

  One hand slips into my hair while the other grips my throat and his mouth descends on mine, savaging me as though he has lost control.

  I match his fierceness and find my leg lifting around his waist so I can get the friction I need.