Daddy's Boss: A Billionaire Older Man Younger Woman Romance

by Lila Younger

  “You don’t have to say that,” I say shyly, peering at him beneath thick lashes.

  I’m used to the fact that I’m the smart one, the brainy one, while my sister claims the beautiful title.

  “It’s true. I’m not just giving you a line,” Lachlan insists, and my heart pounds even faster. “Beautiful and smart and mine.”

  His lips curve upwards in a sexy grin, and for some reason, his words touch on something even more intimate than showing him my body. I feel so light headed that I might just pass out.

  Lachlan bends down, kissing me deeply, thoroughly, as if learning every inch of my mouth with his tongue. My whole body tingles with anticipation as he spreads apart my cunt, opens me up for his cock. I’m still slick with cream, which he rubs all over his shaft, lubricating him for the job at hand. My slit quivers as his cockhead touches me, eases past my folds and into my entrance. He pushes past my virgin resistance, one swift stroke claiming my virginity. I cry out, my hands tightening on his shoulders as he penetrates me. His fingers haven’t stretched me enough, and I pant with exertion as I try to accommodate his cock. My warm pink hole clamps down along his thick cock, tightening and molding to every ridge, every vein. He slows down, not wanting to hurt me, but he doesn’t stop. I’m taking him in, every last inch, and it feels amazing. There are no other words for it.

  “You’re mine,” Lachlan says. It’s not a question, but a fact. A promise.

  My whole pussy pulses with desire as I finally take all of him in, my puffy folds hugging the base of his cock. He begins to move, slowly at first, then his pace picks up. He lifts my leg in the air, leans against it for leverage as he drills into me. Our bodies come together with wet slaps, his cock loosening me up with each thrust. I love having Lachlan in me, stretching me, making me take every bit of him. It feels so good, so perfect, no wonder people do the craziest things for sex. My pussy clings to his cock, refusing to let him out. I need him to fill me up. I need him to feel whole. Desire blooms inside of me as he fucks me hard. Lachlan’s breath is shallow and fast, like mine, and I know we won’t last much longer.

  He flips me over fast, hands dragging my hips up to his, cock slamming into me again. My pillowy ass cushions the impact, but then he does it again. And again. Every time he enters me, I can’t help but moan. He’s so deeply embedded inside of me that his cockhead rubs up against my cervix. I have to spread my legs even winder, my face smushed against the pillow, but I don’t care. I don’t care about anything but Lachlan. His balls slam against my swollen clit, making it throb with pleasure. I can smell us, the scent of our sex mingling together in the air.

  I moan, my body screaming for release as my climax takes over, my body shuddering from the force of it, my pussy spasming and gushing cream around Lachlan’s thick tool as he rides my orgasm to his own. My breast jiggle and shake, and I throw my head against the pillow, my back rising up off the mattress it feels so good. I can’t stop crying out as his cock thrusts into me, hard, dirty, fast, his own body driven to finish. The liquid inside my cunt seeps out as he fills me up one last time. I feel him go rigid inside of me, his dick reaching deep inside of me, releasing another orgasm.

  He stays inside of me, hot as steel for minutes until we collapse onto the bed. He holds onto me tight, and I’m glad, because I’m not ready to let him go. I squeeze my muscles around him, making him groan. All I can hear is our heavy breathing and our pounding hearts. He brushes a bit of hair from my shoulder, kisses it softly.

  “You’re amazing Jenna,” Lachlan says. “That was amazing.”

  I nod, but before I can really say anything, I’m drifting off to sleep in his arms.

  Lachlan

  I can’t stop seeing Jenna.

  When I woke up the next morning after seeing her at the street fair, I knew that the right thing to do was to put on my clothes, and get out of her apartment. Of course, I didn’t do any of that. Instead, I spend the whole day doing my new favorite thing: making Jenna come. With my fingers, my tongue, and my dick. I can’t stop. Just watching that blissed out look on her face gets my cock up even after the fifth time. And then there’s the look she gets in her eyes when she sees my cock, so hungry and willing that I nearly come anyways. I finally have to go home, so that I can get some sleep and shower and get ready for the next morning, but it’s not even five p.m. before I’m calling her, asking her to come over.

  And she’s been in my bed ever since. We agreed right away that her tiny single bed was too small for the two of us. The only reason I could sleep crumpled up in that thing was from sheer exhaustion. Besides that, I love seeing Jenna’s creamy flesh outlined against my dark silk sheets. I love watching her writhe in pleasure, gripping onto my pillows, pushing back against my headboard, as I bring her to climax. It’s been a few weeks now, and our attraction seems stronger than ever.

  It’s like she’s always belonged here. The thought sneaks into my head, and it’s not wrong. But it makes me uneasy. As much as I enjoy Jenna’s company, I’m not sure that there can be anything more between us. In fact, I try to think about that as little as possible, instead focusing on just how many different things I can do to her, how many new things I want to show her.

  I even think about having sex with her in the office. We’d have to be quiet, but the idea of having her spread across my big desk, back arched, legs open just might be worth it all.

  “What are you thinking about?” Jenna asks, propping her head on her hand and elbow. “Is it the Toys 2 Tots contract again?”

  “No, but I am worried about it. I heard that GDA Manufacturing has jumped into the bidding too. They’re twice our size, and they seem to win every bid they put in these days.”

  They also have an advantage by putting up their plants in the south, where wages are low, and because they aren’t held to strict environmental standards, they’re able to provide things much more cheaply than we would be able to. I’m still confident in our ability to fulfill what Toys 2 Tots want, but sometimes all that matters is the bottom line, and that’s one area where we just can’t go as low as everyone else.

  “I was considering heading down to Riverton. Might be easier to convince them if I can get them into a meeting,” I tell her. “I might leave this Friday if I can arrange it.”

  “Oooo. That’s near L.A. right?” she says, sitting up. The comforter falls down around her heavy breasts. She’s fucking gorgeous, and I never waste a chance to really drink her in, from the tip of her button nose to her shaved pussy, which is pink and glistening, swollen like a ripe peach. She was shy the first few times, keeping herself covered, but after I pulled it down a few times, she’s begun to embrace it. “Do you think maybe… I could come along? It would be nice to be able to make a weekend out of it. I feel so cooped up, since we never get to go anywhere. I mean, I understand why you want to be careful, but it would still be nice, don’t you think?”

  “Sure, I don’t see why not. It would be nice not to have to keep looking over my shoulder. As long as you think you can keep your parents from catching on.”

  “No problem,” she says, her eyes lighting up. “I can make up some excuse, and they never come to my apartment to check up on me. I can’t wait! A weekend away. How romantic.”

  The word surprises me, but it doesn’t bother me like it would if it had been anyone else who said it. There’s something that’s different about Jenna. I know I said it before, but it’s not just about our physical attraction. I like her company. I could see us being together, walking out on the street holding hands, maybe taking in a dinner and a show. I mull the thought in my head, surprised by just how much she’s changed me.

  ********

  Jenna and I arrange to meet at the gate. It’s early, but the airport is already teeming with people. To keep things proper, I’ve paid for her plane ticket out of my own funds, instead of the company’s. That sort of shit tends to bite CEO’s in the ass, and if there’s something I’ve learned, it’s that in this day and age, there will always be
a paper trail. I do not need any scandal about ‘misappropriating company funds’ when there’s a big contract on the line.

  I roll my carry-on, keeping my eyes open for her. It didn’t take me long to pack, and aside from my suit, which I’ve got in a garment bag, I only packed a few changes of clothes and my toiletries. L.A. this time of year is already too hot, but I have a few ideas in mind for what we could do. When I get to the gate, I pick a spot and sit down, opening my laptop to confirm our hotel and make dinner reservations for tomorrow.

  It isn’t until the desk agent calls for boarding that Jenna shows up. She’s dressed in a tank top and miniskirt that shows of her legs, and she looks downright sexy, especially in comparison to the fully buttoned shirts and modest pants that she usually wears in the office. Her hair curls around her face, which is flushed from her run. She loops her arm in mine, pressing her soft breasts against my arm. I inhale the scent of her, something that’s only for me.

  “Hi,” she says breathlessly. “I’m sorry. I’m not used to getting up this early.”

  “I guess I shouldn’t have kept you up so late last night,” I murmur into her ear as we head to line up.

  “That’s okay,” she says. “It felt weird to be sleeping in my own bed. I guess I just got used to yours.”

  We hand our tickets to be scanned, but Jenna is looking at something else when the agent hands it back. I take hers, and gently steer her towards the bridge. She’s chewing on her lip, a frown on her face.

  “Something the matter?” I ask.

  “No, I just thought- never mind,” she says. Her frown smooths out. “I’m sure it’s nothing.”

  We make our way to the business seats, and I put both of our luggage in the overhead compartment. It’s a tiny commuter plane, so the aisles are tight, but I’ve never been too interested in the trappings of wealth. My car and my apartment, with its panoramic view of the city and harbor, are my only indulgences. She slides in to the window seat, and I take the aisle. She pulls out her phone to answer a message, and I take the time to answer some last minute emails. More passengers troop in, and soon the engine is humming and the attendant is demonstrating the safety features of the aircraft.

  I look over at Jenna. I’ve always loved the beginning of a trip, no matter how small the distance. There’s something about that promise of adventure that’s stayed with me, even as I grew up. But it seems like she didn’t share my feelings on it. Her blue eyes are wide with fear.

  “What’s the matter?” I ask, when she grips onto my hand tightly.

  “Just nervous,” she admits. “I’ve never flown before.”

  “Never?”

  “Nope. We aren’t a big travelling family. We did do a few summers at Lake Tahoe when I was little, but we drove for that,” she says. “So I’m a little bit scared I guess.”

  The worry in her eyes tell me that she’s more than a bit scared. I put a hand over hers, wanting to protect her from this, from everything.

  “You don’t have to worry about it,” I tell her. “I’ve flown a million times, and nothing’s ever happened. Not even through the worst turbulence.”

  “But what about all those horror stories about planes killing everyone on board?” she says softly as we begin to taxi down the runway.

  “Would it help if I told you you were more likely to die in a vehicle accident than a plane? In fact, when you compare the two, the risks of flying are almost zero.”

  “That sort of helps, but-”

  Just then, the engines go full blast, and we’re pushed into our seats. I can see the fear written across her face. To be fair, takeoffs are the most terrifying part, as the plane wobbles into the sky.

  “Hey,” I say. “I’ve got a fear too. Can you guess what it is?”

  She shakes her head, but the distraction seems to be helping.

  “Yup. Had it since I was a kid. I hate heights of all kinds, so I know a little about how you feel right now.”

  Jenna’s mouth drops at my admission. I’m not used to revealing my weaknesses, but if it’ll provide her some comfort on this trip, then so be it.

  “Is that why you let me take the window seat without a fight?”

  Her voice is evening, the fear from before slowly disappearing as she lets herself get distracted by my story.

  “You caught me. It all started when I was eight. My cousin dared me to go off the tall diving board. I managed to climb all the way up, but I chickened out of jumping at the last second. What I didn’t know was that he was right behind me, and instead of letting me go, he pushed me off.”

  To say that I was terrified doesn’t even begin to cover it. It seemed like forever before I fell into the water, back first, knocking the wind out of me. And then I was thrashing in the water, scared witless. Luckily my uncle heard the commotion and came out to the backyard, saw what was happening, and dived in to get me. I cried like a baby that day, and my mom forbade me from playing with my cousin anymore, thank god. He was a bit of a jerk, and the pool was only one of the many ‘pranks’ he pulled on me.

  “That’s terrible!”

  “They were the longest few seconds of my life,” I say. In fact, even recounting it now makes my heart jump. “I don’t think I went near another pool for at least a year.”

  “I can’t believe he could do something like that,” she says indignantly. For some reason, that made me happy. “I hope he got into lots of trouble.”

  “He did, but he was only ten at the time. To be honest, neither of us should have been on that board.”

  I can feel the plane leveling off slowly. My story worked; I’d gotten Jenna through the worst of it. The flight attendant comes by to take our drinks. I order a coke for myself, and Jenna gets some water.

  “Thanks for this,” she says as she takes a sip of her drink. “I think I feel a bit more okay now.”

  “That’s what I’m here for. You might want to pull down the window so that you don’t have to see how high up we are.”

  “Good idea.”

  Jenna opens her tray table and puts her drink down.

  “So,” she says. “Are you ready for the meeting?”

  “Yes. Ready as I can be anyways. We’ll have to hurry when we land. Will you be alright while I’m at the meeting?”

  “Sure of course,” Jenna replies. “Riverton has an outlet mall, so I was planning on getting my mom her birthday present.”

  “Perfect. I was thinking that we could go down the Walk of Fame, maybe catch a Dodgers came today too,” I say. “They’re in town, and they’re actually decent this year.”

  She wrinkles her nose.

  “Sorry. I don’t really enjoy most sports,” she confesses. “Are they a team you really want to see?”

  In the past, if a woman didn’t enjoy a game, I wouldn’t hear about it until we broke up. In fact, most of the women I went out with probably didn’t tell me anything of substance about themselves, molding their personality based off what they thought I would want. So for Jenna to say so directly that she has no interests in sports, it caught me off guard.

  “No,” I say slowly. “I’d be happy to skip the game if there’s something you had in mind instead? Did you want to go to Rodeo Drive?”

  She pauses, pondering. There’s that lip biting again, and I wait patiently for it. I’ve done my fair share of shopping with women before, and although I usually have no patience for it, I would go all day if it meant spending time with Jenna.

  “There is something,” she says slowly. “I don’t know if you’ve heard of… The Wizarding World of Harry Potter at Universal Studios?”

  I break out into a grin.

  “Are you telling me you’re a Potterhead?”

  She nods, and there’s absolutely no embarrassment at all. Like I said, she’s earnest. I like that, and I really like the fact that she’s not afraid to be who she is around me.

  “Wait,” she gasps. “Don’t tell me you’re one of those weirdos that haven’t read the book?”

 
“What if I am?”

  “Well, we’d have to fix that. Immediately,” she says.

  “I think I’m a little too old for books about wizards,” I say drily.

  “Not if I’m reading them to you. Naked.” She leans in, whispering the last word seductively just for my benefit. I can feel my body heating up, my cock stirring in my jeans at the thought.

  “Now that, I think I can get into,” I say as I kiss her, right out in the open.

  And it felt damn good. We talk more, about other books she enjoys, and my love for baseball coming from when I was in little league, and then about everything else we could think of, until we bump down onto the runway.

  “Thank you for distracting me Lachlan,” she says. “I don’t think I could have done this without you.”

  I’m elated that I could have done this for her. Maybe, just maybe, after this trip is over, we can find some way to make this work. Because if there’s any woman that’s worth taking a risk on, it’s Jenna.

  Jenna

  It’s a blistering hot day in L.A., but the Town Car that Lachlan got to drive me to the outlets is already fully air conditioned. He’s going to take our bags to the hotel and get us checked in so he can change before his meeting too. The traffic isn’t terrible, which is surprising, because I’ve always heard it’s supposed to be bumper to bumper here in L.A. I sort of wish that Lachlan is still with me, because I’ve never travelled on my own, but I know he’s got important things to do.

  The outlet mall is an enormous complex with faux Spanish style architecture. The whole place reminds me of a classy resort, not a mall. There are palm trees everywhere, and even though it’s a weekday, the parking lot is jam packed with people. I let my driver know when I’ll be back, and he drops me off. The storefront stretches on and on and on, and because I have no idea just what’s here, I decide I’d just start walking.

  Pretty soon, I’m overwhelmed with options. The outlet has everything, from mass market chains to luxury brands. I manage to find a few things to buy that I think I’d look good in for our dinner tomorrow night, but I can’t decide on what to get for my mom. She’s already got everything she needs, and she’s not much of a trend follower. I think about getting her a gift card, but my mom is one of those people who spends forever finding gifts for people. I know that a gift card would hurt her feelings. The only thing I could think of is a brand new Dutch oven at Le Creuset, but I can’t imagine trying to haul something that heavy home with me.