Her Boss: A Billionaire and Virgin Romance

by Roxeanne Rolling

  “We have to play different teams from all over the country,” says Dan.

  “Cool,” says Scout. “Who are you playing tomorrow?”

  “I told you,” I say.

  “One of the new California teams,” says Dan. “Here you go Scout, this is your room while you stay here.”

  “Wow,” says Scout, entering the room.

  Dan’s done his best to make the bed, although I can tell he doesn’t really know what he’s doing.

  “It’s a huge bed!” says Scout, who’s used to her twin bed. This one, though, is a king sized bed.

  “That looks like a lot of fun for you, Scout,” I say. “I think you’ll sleep really well.”

  “And here’s a room for you, Chloe,” says Dan, giving me a wink that Scout can’t see.

  He shows me to another room.

  “It’s nice,” I say, smiling at him. I know as well as he does that I won’t be sleeping there, but I do appreciate the extra touch of him pretending that I have my own room, for Scout’s sake of course. Of course, Scout wouldn’t care either way, but I understand that Dan wouldn’t know that.

  The two of them look so similar in some ways that it’s almost uncanny. Sure, I’ve noticed the resemblance before, but I’ve never seen them standing together in the same room before, where their features really seem almost identical in some ways.

  I feel a pang in my heart. I still haven’t decided what I’m going to do about this, about telling them. Dan’s the one I worry about, of course. I’m sure Scout would be delighted to have a father, provided I tell him, that is.

  But I feel like a horrible person, a complete fraud, staying in Dan’s house like this without telling him the truth.

  How can I go through with this?

  I resolve right here and now that I’m going to tell Dan before we leave. I have to. I simply have to. There’s no other way, and it’s the right thing to do. But just because it’s the right thing doesn’t mean it’s any easier for me to get my head around, for me to stomach.

  Dan puts my bags in “my” room, and then shows us the rest of his house, including his room, which, like the rest of his house, has almost nothing in it.

  I catch myself wondering how I would spruce up the house if I were to live here with Dan and Scout.

  But that could never work, right? After all, I have my own business hours away. How could it really work out between us?

  But as I look at Dan and his body, the warm feeling comes back into my chest, and I push the thoughts to the back of my mind.

  “Well,” says Dan. “I can make you two gals something here in the house for dinner, or we could go out to eat.”

  “Out!” says Scout, almost jumping up and down in excitement.

  “You’d think she wasn’t well fed or something,” I say.

  “Sounds like out is going to work well,” says Dan, smiling. “What do you want to eat, Scout?”

  “Pizza!” says Scout.

  “I think your friends in school told you that the Philly pizza is really good, right?”

  Scout nods.

  “Let’s head into the city then,” says Dan. “Anyway, I’m not much of a cook.”

  “We’ll have to work on that,” I say, not quite sure myself what I mean by that.

  Dan gives me a quizzical look but doesn’t say anything.

  I guess it sounds like I’m implying I’m going to try to turn him into a husband or something.

  “Honestly,” I say, as we all pile into Dan’s car, a nice SUV. “I figured that all you football players were living in mansions or something. I mean your place is nice, don’t get me wrong, but…”

  “You were expecting something fancier?” says Dan, chuckling, as he puts the car in reverse and drives backwards out of the suburban driveway.

  “What’s a mansion?” says Scout.

  “A really, really big fancy house, honey,” I say. “A lot of wealthy people and famous people have them.”

  “Only the famous people who aren’t good with their money,” says Dan. “Frankly, I never saw the need, and I don’t spend much time here, as you can see. I have another apartment in the city, one that I just never wanted to get rid of. I mean, people are always telling me real estate is a good investment, but that’s really only if you buy something sensible. Mansions depreciate just like cars.”

  “I never would have pegged you for being good with money,” I say.

  Dan acts surprised and offended and I laugh.

  He drives us through the city. We head along the Schuylkill River, and he points out the art museum that looms on the shore.

  “What a cool old building, right, Scout?” I say, and she’s pretty impressed. We don’t have buildings like that, huge stone edifices, in our home town.

  “That’s where Rocky ran up the steps,” says Dan.

  “I can’t believe I’ve never seen it,” I say.

  “You didn’t have a chance to get into the city much?”

  “Not with Dad, and then Scout,” I say. “And now that I’ve got my own business, well, let’s just say I’m lucky to be able to steal away today to come here.”

  Dan drives us through Center City, which is really crowded, meanwhile pointing out all the different sights. I’m feeling sleepy and the sky is already dark, but Scout is completely fixated on the sites.

  We continue on over to South Street, a hip kind of street, with all sorts of funky little stores and all sorts of characters walking around that are enough to keep Scout amused for hours, provided I can stay awake that long, of course. I had a client this morning who wanted a double session, so it was an unusually busy and tough day for me, especially considering the drive took us an extra hour with the traffic. (Yeah, I left really early, since I was anxious about meeting Dan on time.)

  “There’s a really good pizza place on the corner up here,” says Dan, pulling up alongside a car and then backing up, executing a perfect parallel park.

  “I could never do that,” I say.

  “It’s easy,” says Dan. “You’re just not used to it.”

  Scout wants to order five slices just for herself, with all sorts of different toppings, which is a little ambitious for a child of her size and stature, so Dan and I agree to just order a large pizza that we can all share.

  “This is really good,” I say, taking my first bite.

  Scout’s already got her mouth full of a slice of peperoni, sausage, and peppers, a look of complete contentment on her face.

  “This is good,” says Dan. “I’ve got to carbo load for the big game.”

  “They tell you to eat pizza?” I say, laughing. “I thought they’d want you to choose something healthier.”

  Dan shrugs. “They can tell us what they want,” says Dan. “But we know what works, and that’s basically just calories.”

  I laugh.

  The rest of the cold crisp evening we spend walking around South Street. Scout hasn’t been anywhere like this before, and I figure it’s a good part of her education to see different things. She hasn’t ever seen the types of characters that hang around South Street, the artists, the punks, and the street musicians who completely captivate her. I give her a couple quarters to drop into the cup of a guy who sings and plays piano at the same time, with, for some reason, a blindfold carefully wrapped around his eyes.

  “Well,” says Dan. “There’s just one more thing I wanted to show you girls, and then we can get going back home. I’ve got to wake up early tomorrow. And, don’t worry, the seats are all set for you. The tickets are at home.”

  He takes us down a little alley and the strangest sort of building that I’ve ever seen is at the end of it. It’s a building that’s not a building at all, but more like a living piece of art, a structure made completely out of old glass bottles, tires, and all sorts of things that we would normally consider trash.

  “Isn’t it cool?” says Dan. “I think it’s closed now, but it’s called The Magic Gardens. If you come back in the day some time with me,
we could take a tour of the inside.”

  “Wow,” says Scout, reaching out and touching a piece of the smooth glass that makes up the wall, along with cement.

  “That’s really something,” I say.

  “Yeah,” says Dan. “The guy who made this basically spent his whole life making similar art projects. He has murals all over the city.”

  “I’m cold,” says Scout, starting to shiver.

  I wrap my arms around her and suggest that it’s time that we should be heading back.

  “Good idea,” says Dan, checking his watch.

  He guides us back to his car, and drives us smoothly out of the city into the suburbs where his house is.

  “You look tired, Scout,” I say.

  “I want to stay up with you two,” says Scout.

  I wink at Dan, and listen to Scout tell me why she needs to stay up.

  Of course, as always, a minute later, she’s so tired she can barely keep her eyes open, and I put her to bed, where she promptly falls fast asleep and starts lightly snoring, her eyes closed, her face up towards the ceiling, her cute little head resting peacefully on the pillow.

  I head back into “my” room for a moment, intending to get changed into something more comfortable and perhaps more revealing.

  Dan comes into my room, and smiles at me when he sees me starting to pull my shirt off. I leave it on, and walk towards him and wrap my arms around him, embracing him, and he kisses me on the lips.

  “She get to sleep OK?” he says.

  I nod. “She sleeps heavily,” I say, giving him a meaningful look.

  “The walls are thick,” he says. “No sound goes from room to room. One of the few upgrades I’ve made to the house.”

  “Good,” I say. “But you sure you don’t need to rest up for the big game?” I’m loving this little game of double entendre that we’re having. I’ve never thought of myself as someone who’s good at flirting, but maybe I’m good at flirting once I’m already in a relationship. But is this a relationship?

  Dan opens his mouth but for a moment I realize I’m not listening at all to anything he says. All I can think about is that this would be a great moment to tell Dan about Scout, that she’s his daughter, and that I hid the pregnancy from him. But, there’s always an excuse in my mind. I can talk myself out of anything if I really want to, and right now I’m rationalizing not telling him by telling myself that I don’t want to screw up his performance tomorrow at the big game.

  “You there?” says Dan, looking at me with a concerned look on his face.

  “Oh, yeah,” I say, snapping out of it.

  “You didn’t seem like you were listening?” says Dan. “Are you feeling OK?”

  “Yeah,” I say. “Sorry, it was nothing. My mind was just drifting… back to work, you know?”

  “Yeah,” says Dan. “I bet that can be pretty stressful, having your own business.”

  I nod. “Anyway,” I say. “Does Coach let you have some fun before your games?”

  I grab his crotch jokingly to show him what I mean, and I’m surprised (although I don’t know why I should be) to find that his cock is already quite hard, creating a sizable bulge in his pants.

  “Coach says we’re not supposed to so much as mess around,” says Dan, imitating a very serious tone. “But I know better.”

  His hand slides down my back and onto my ass. He squeezes it and I giggle.

  “Let’s head into my room,” he says. “…Our room, I mean.”

  “I like the sound of that,” I say.

  I follow Dan, who leads me by the hand into his bedroom.

  He pulls me gently down onto his big bed, which is cushy, but that’s the last thing on my mind. I’ve completely overtaken by his body, his breath, his hard and warm muscles, that feel good against me in the slight cold.

  “It’s a little cold in here,” I say, laughing, kissing him, our hands all over each other.

  “Let’s get under the covers, then,” says Dan, pulling a thick down comforter over the two of us.

  It’s warm under here, and his body is like a furnace, generating a great amount of heat.

  Dan’s hand goes up my shirt, massaging my breasts gently.

  “That feels really good,” I say, relishing in the feeling of his strong hand on my bare flesh. Somehow he’s gotten my bra undone quickly without me even noticing. That’s not always a good sign, but in this case it’s a great one. He really knows what he’s doing.

  Dan’s kissing me at the sensitive nape of my neck, on my ear lobes. He’s whispering hot things into my ear, telling me he wants to sink his thick cock deep inside me, telling me that he’s hard for me, that he can’t wait until he’s inside me.

  He works his kissing down my body, removing my shirt completely in the process, my bra falling away. We’re almost completely under the covers, the atmosphere is warm, comfortable, intensely sexy. It feels like we’re in our own little world, away from everyone else, just able to enjoy one another’s bodies for all eternity.

  Dan is kissing my breasts, his tongue lapping my nipples, and his lips sucking on them.

  I moan in anticipation of what’s to come, and I moan with the pleasure, the subtle pleasure that I’m feeling with his lips all over me. I love the way he’s paying attention to every part of my body as if each and every part of my skin is incredibly important, as if my skin is the sensual organ that it really is.

  “Oh, Dan,” I moan.

  Dan growls a positive response, but doesn’t say anything as he goes farther and farther down. He’s at my belly button now. His strong hands are gripped around my back, pulling me up and towards him. The bulk of his body is over top of me, between my legs, with his torso and his legs resting on the mattress mostly, part of his big muscular weight on top of me.

  Now Dan pulls my pants down in a swift motion. Just my panties remain, covering my pussy, which is ready, as ready as it’s ever been for Dan’s massive cock. I reach down and try to feel for his cock, but I can’t reach it. I know, though, that he’s rock hard, his pants barely containing his massive, throbbing member. I can perfectly picture his cock’s head when I close my eyes, and the way that it felt when it was in my mouth.

  Dan’s licking my hips, at the indent where my legs meet my torso. He runs his rough tongue softly along my thighs, working his way down and down, closer and closer.

  He surprises me by going all the way down to my ankles, cupping them in his hands and licking them, kissing them. Now he’s coming back up. This time he’s not going to be stopped. This time he means business, his fingers massaging my pussy through my thin underwear. I wore my special stuff today, the one pair that I’d been saving for years for that special night that I always wanted but never came. They’re lacy and fancy and they’re practically see-through, a fact that makes it all the more obvious right now how excited I am. My breathing is ragged and fast, my breasts rising and falling. I put one hand on my own breast and squeeze myself. The other hand goes onto Dan’s head, working its way through his thick hair, massaging his sexy head, his scalp.

  “I’m going to show you how good this can really feel,” growls Dan, and a moment later he’s pulled my panties off, so quickly that I wonder if he’s ripped them, but I don’t care. That’s the last thing I care about right now.

  Dan’s hands are on my thighs, pulling my legs apart, pressing my knees into the soft mattress. I’ve never felt so safe, so taken care of, as right now, under the covers with Dan.

  The covers are still over my head completely, the light streaming in from the sides, through the seams.

  Dan kisses my pussy, a delicate and soft kiss.

  Slowly, very slowly, he begins to change his kiss into licking, into the most pleasurable sensation that I can ever remember feeling in recent years. It’s almost as pleasurable as an orgasm already, with the waves of pleasure riding through me. I’m like some surfer out in the wild ocean, the strong sun blasting down onto me, warming my body in a way it’s never been warmed befor
e, striking all the way through to my bare soul.

  Dan’s slowly involving his hands into the mix, exploring me, inserting a finger slowly, ever so slowly into me. I gasp and moan as it comes inside me.

  He keeps licking me, his rough but soft tongue changing constantly the way it’s working, long, powerful strokes and shorter, faster ones, delicate and then powerful, all the while through the changing tempo working up into an absolute frenzy.

  His tongue is hitting my clit quickly now, and two fingers are inside me, penetrating my delicate body, pumping in and out. They’re pleasurable, but they’re just making me hungry for his thick cock. I need him inside me. I crave him, and I crave his cock. I need to be filled up with him, that sensation that’s indescribable, in which my body feels complete and whole, in complete accordance with the pleasure that we all need to feel.

  The orgasm comes on me suddenly, a huge flush of pleasure. I gasp as it surges through me unexpectedly. I can feel Dan reacting, responding to my body’s new desires. He only increases his speed, increases the intensity. I love the feeling of his face right between my legs, buried and working away. It’s so intimate, so close, so personal and so hot.

  I scream out, not too loud, since I’m trying to restrain myself. I’m moaning involuntarily.

  I close my eyes and open them, and I can barely tell the difference. My vision is changed during the orgasm, during the rush of it all, a fuzziness and warmness replacing my field of vision. My breathing is quick and intense.

  Only after it’s over do I realize that my legs have been involuntarily gripping Dan’s head, so as to keep him between my legs, not that he would want to move anyway.

  “That was so hot,” whispers Dan deeply in my ear, coming up over top of me, his thick, powerful chest resting against my breasts.

  “That was…” I say, and then start giggling. “It was so hot.”

  But the giggles fade away quickly into complete lust.

  “I need you,” growls Dan, his voice deep and powerful.