Her Boss: A Billionaire and Virgin Romance

by Roxeanne Rolling

  “You never got back to me about Friday,” says Dan, his voice taking on a mock serious quality.

  “It’s a definite yes,” I say. “Scout’s really excited.” I tell myself that I’m just going to have to pretend for a little while that I’m not worried about Scout and Dan, and that whole situation.

  “Good,” says Dan. “I’m glad.”

  “You sound really tired,” I say.

  “I am,” he says. “Practice was torture. Coach wanted to punish me for taking the time off.”

  “Didn’t you tell him you were helping your elderly mother?”

  Dan laughs. “That sort of stuff doesn’t cut it with Coach,” he says. “He just doesn’t care.”

  “Sounds like a sweet old man,” I say.

  Dan laughs.

  “It’s good to hear you laugh,” I say.

  There’s a pause on the other end of the line.

  “That was really fun last night,” says Dan.

  “If that’s what you want to call it,” I say, laughing. “I was hoping you’d describe it in… I don’t know, more sensual words.”

  “Well,” says Dan. “There are a lot of ways I could describe it. I’ve been thinking about it… about you all day. I couldn’t get you off my mind.”

  “That’s the kind of talk I like to hear,” I say. “Keep going, why don’t you?” I’m trying to make a joke, but Dan takes me seriously.

  “I’ve been thinking about your beautiful body,” he says. “And, well, there was something special. You know what I mean? I really feel like there’s some kind of real connection between us?”

  “I know what you mean,” I say. “I felt it too.”

  There’s a silence on the other end of the line.

  “I can’t get you off my mind,” says Dan, again, at least for the second time this evening. “I keep thinking about your body.”

  “What’s it making you do?” I say, trying my best to be coy. Of course, I’m wondering whether his cock is as rock hard as it was last night, and whether or not he’s touching himself. “Are you alone?”

  “Yeah,” says Dan. “I’m at my place. What about you?”

  “I’m headed to my room,” I say. “I’m the only one awake in the house.”

  I head into my own bedroom, and close the door behind me. I make sure to lock it. The sound proofing is good in here, although I’ve never really had an opportunity to seriously test it. I’ve never had a man like Dan in here to really test it with.

  “I’m completely alone,” I say, into the phone. “I’m all yours.”

  “What are you doing?” says Dan.

  I giggle. “I’ve never had phone sex before,” I say.

  “Oh?” says Dan, acting surprised. “Is that what we’re doing?”

  “You know damn well that’s what we’re doing,” I say. “Now tell me, do you have your hand on that big cock of yours?”

  “Not yet,” says Dan. “Maybe you could tell me how to do it.”

  “How many times have you jerked off in your life and you still don’t know how to do it?”

  “I just need some help,” says Dan.

  “I bet I’ve given you plenty of help already,” I say, giggling. I never talk like this, but with Dan, I find that it’s easy. It comes out naturally, as if there’s nothing to it. “You probably jerk off to me all the time.”

  “It’s true,” says Dan, somewhat gravely. “For the last six years…”

  I inhale sharply. I never would have imagined the guy I was fantasizing about all these years, the guy I was longing for, the famous football player… that he was jerking off to me, fantasizing about fucking me.

  “That’s so hot,” I say. “Now unzip your pants.”

  I can hear Dan’s breathing increasing over the phone and I can almost make out the sound of his zipper coming undone.

  “It’s out,” says Dan.

  “Take it in your hand,” I say. “And slowly stroke it. And think about me. Think about how good I felt last night.”

  “That’s so hot,” says Dan. “Are you touching yourself?”

  “Not yet,” I say, my fingers posted right at the edge of the waistband of my panties. I’m wearing my pajama bottoms, my panties, and an old t-shirt without a bra.

  “Slide your hand down there,” says Dan, his voice deep and commanding.

  I do as he says, and my hand slips down underneath the elastic waistband and I touch myself. I can tell that I’m ready.

  “Now massage yourself,” says Dan.

  “Are you playing with your cock?” I say.

  “Yeah,” says Dan. There’s a slight pause. “You got a laptop?” he says.

  “Of course,” I say. “But I’m not interested in watching porn if that’s what you’re about to say. You men are disgusting, always watching porn…”

  Dan laughs. “I was going to suggest we video chat,” he says. “I’ll text you my user name.”

  “See you in a second then,” I say, glad that he can’t see me right now, blushing at my mistake.

  Half a minute later, my laptop is open on the bed, and Dan’s face appears on my screen. I turn my own video chat on, and Dan gets a look at me in my t-shirt, without any makeup.

  “You look ravishingly beautiful,” he growls, his voice hot and heavy and deep.

  “Thanks,” I say, blushing again, and this time he can see me. “Now give me a good look at that monster cock of yours.”

  Dan doesn’t blush, of course. Instead, he grins at me, and changes the position of his laptop so that the camera view shows his whole body.

  His pants are unzipped and pulled partially down. His cock is truly massive in the camera, thick and long, with a slight curve, his big head looking like it’s threatening to burst. Dan’s big strong hand is gripping his cock lightly.

  “I want you to really stroke that cock for me,” I say.

  “First you’ve got to show me what you’re up to down there,” says Dan, smiling at me, perhaps a little wickedly, a little mischievously.

  I gingerly move the laptop so that it shows my whole body.

  “You don’t care that I’m in an old t-shirt?” I say.

  “You’ve never looked hotter,” says Dan.

  “What about last night?”

  “Well… maybe not never,” he says.

  I giggle.

  The thoughts of last night drive me into more of a frenzy. The sight of Dan’s cock, too, is driving me closer to the edge.

  “You’ve got to take off your pants and panties,” says Dan.

  I gingerly slide them down to my knees.

  “That’s better,” says Dan, a slightly greedy tone to his voice.

  He’s really stroking his cock fast now, sliding his fist up and down it quickly. I can see his abdominal muscles tensing. His shirt is off now. His arm muscles are bulging. He has a look of intensity in his eyes.

  Dan’s staring now at me, at my breasts, which I expose by lifting up my t-shirt and showing my braless breasts.

  His hand is a blur now on his cock.

  I’ve got one finger inside me, moving in and out easily, and one finger on my clit.

  The initial super-sensitive period has faded, and I’m really moving my fingers quickly now, my breathing rapid.

  I’m about to come, staring at his huge cock. He’s thrusting now, into his fist. His breath is heavy. A moment later, his cock explodes, his cock head erupting and his come shooting up, load after load.

  I come upon seeing it, the orgasm exploding through me.

  Dan

  One more day until the big game. Coach wants to ride me hard, but he knows he can’t today. Even the toughest athletes need a day before competition to recuperate.

  All week, he’s had me been doing the most insane drills, practicing footwork over and over, until there are blisters on my feet and there’s nothing in my head except footwork and plays.

  People think football is simple. They think it’s just big guys running into each other. Nothing could be f
arther from the truth. It’s insanely complicated. Some people have compared it to chess, but in reality it’s even more complicated. Unlike in chess, in football, there are always layers of strategy, layers of movement and thought. For instance, Coach and the assistant coach handle the plays, with some input—it’s really like analyzing history, with strategic innovation thrown on top of it. But it’s not like he can just command a play and that’s it. He’s got to have us, his players, able to execute the plays. And no play ever goes fully as planned. We always have to innovate and invent on the field.

  It’s as much of a mental game as it is a physical game. And there are many components to the mental aspect of it.

  I’m tough though, I know that. Tough physically, but tougher mentally.

  Today we’re supposed to be just resting and bonding with the team, hanging out together, but not drinking, at least not too much. Myself, I stay sober at least a week before the game, and that means not a drop of alcohol, as well as a clean diet. The all natural food, including plenty of protein, makes me function better.

  Chloe’s supposed to be bringing her daughter into the city today, and they’re going to be straying with me at my somewhat empty suburban house, despite how boring it is.

  “Dan!” shouts Coach, during our meeting to go over the plays. “You going to keep checking your phone all day or are you going to listen to me for once?”

  “Sorry Coach,” I say, putting my phone away.

  Chloe didn’t call yet. Only a couple more hours to go until she gets here. She did send a text message saying she’s on her way.

  “Get your damn head in the game,” shouts Coach at me.

  But it doesn’t matter. He’s always shouting at everyone.

  My mind isn’t on the game though, even though it should be. Instead, it’s on Chloe. I just can’t get her body out of my head. I can’t get the way she looked on the computer screen out of my head as I stroked my cock to her. She made me come so hard, and so fast, even though I was trying to go slowly.

  Of course, in person, I can last longer.

  Finally, the lecture is over, and Coach shuts down the projector that’s been displaying plays on the wall. I already have them memorized by heart anyway.

  My cock’s partially hard from thinking about Chloe and all the things I’m going to do to her, so I stay seated for a minute.

  “What’s the word, Dan?” says Jim, one of my teammates, and probably the guy I’m closest to on the team. Although I’m not one for having close male friends. That’s just how I am. Sort of a lone wolf, I guess, by nature. It wasn’t always like that. Back in college, I had a ton of friends, and we’d party and all that. But something changed, especially after college, and I’ve been going the solo route… with just woman after woman, that is until I reconnected with Chloe, of course. “You there, Dan, man?”

  “Yeah,” I grunt. “Same as always, I guess,” I say. “You ready for the game?”

  “Don’t try to front with me,” says Jim. “Front” is a big Philly expression that we all use from time to time, meaning “don’t put on an act.” “You seem different, like you’re distracted or something.”

  “Doesn’t matter,” I say.

  “Well, it does matter,” says Jim. “If it’s going to be messing with your playing. Shit, man, this is one of the most important games of the season.”

  “I know, I know,” I say.

  “What is it, Dan?”

  “A woman,” I say.

  To my surprise, Jim starts laughing, a deep laugh that echoes all around us. The rest of the room is cleared out now. Even Coach has packed up his presentation gear and left to brood over plays in his office.

  “You’re getting all hung up on some woman?” says Jim, barely able to speak from his laughter. “That doesn’t sound like you.”

  “It’s not like that,” I say. “She’s someone special…”

  “I bet she is, Dan,” says Jim, getting up and continuing to laugh as he walks out of the room. He’s actually holding his stomach because he’s laughing so hard. “Get this, guy,” he calls at some of the other players. “Dan’s all hung up about some chick…”

  I hear their laughter and I frown to myself as I get up and head into the hallway, keeping my distance from them so that I don’t have to confront them.

  I head home, and on the way I give Chloe a call.

  “You close yet?” I say.

  “We’re already here,” she says, her voice sounding nervous.

  “You sound nervous,” I say.

  “I’m OK,” she says. “I guess we just beat the traffic and I wasn’t expecting to get here so soon.”

  “I’m sorry,” I say. “I should have left a key out or something for you. I just didn’t realize you’d be here so soon.”

  “It’s OK,” says Chloe. “I’ll see you soon, OK? Scout’s really looking forward to meeting you.”

  It sounds like she swallows hard as she says this and I wonder why. Maybe she’s just nervous about her daughter meeting a new boyfriend.

  Then again, am I her new boyfriend? We haven’t talked about anything like that really, but in the back of my mind that’s now what I’ve been hoping for. Hell, I haven’t had a girlfriend, since… Who knows when. I don’t know if I’ve ever really had one. I’ve had women that were friends with benefits for as long as a month, but usually things just didn’t work out that way.

  “Tell her I’m looking forward to meeting her,” I say. “I’ll see you both soon.”

  I don’t want to keep them waiting for long, and I figure that Chloe’s daughter is probably hungry, so I put my foot to the gas and merge into traffic on the highway.

  My phone rings and I pick it up without looking at it, thinking that it might be Chloe.

  “You resting tonight?” says Coach’s gruff voice.

  “Sure thing, Coach,” I say, not really paying much attention. After all, I’ve got to pay attention to the road.

  “I heard some talk about you and some woman.”

  “That’s my private business, Coach,” I say, a little bit of anger rising. After all, what’s it his business if I’m going out with Chloe.

  “Just don’t want anything to distract you from the game tomorrow,” says Coach, a bit of a threat in his voice.

  “Don’t worry yourself too much about it,” I say, knowing this is going to sound pretty insubordinate and not caring in the least bit. “I want you getting plenty of sleep before the big game.”

  With that, I hang up the phone.

  I laugh to myself. That’ll show him.

  My phone rings again and I check it and it’s Coach. I can picture him red in the face over me hanging up.

  I swipe right, answering the phone, but I don’t bother holding it up to my ear.

  I can hear him screaming at me from where the phone is on the passenger’s seat.

  Whatever. I hang up the phone. It rings again but I hit “ignore.”

  That’ll show him. What’s he going to do, anyway? He knows he can’t run the team without me. Yeah, I know it sounds cocky, but I really am indispensable.

  I pull into the driveway and see Chloe and her daughter sitting on the front stop.

  My heart feels like it’s rising in my chest.

  I jump out of the car in my workout clothes, probably smelly as hell, because I did run a few laps today even though we’re not supposed to be doing anything physical.

  My phone beeps at me, and I look down. A text from Coach that reads, “At the very least, no sex tonight.”

  I laugh that one off. He can’t run my life, no matter how much he tells us “no sex before a game,” I’m sure almost no one follows that rule. After all, football players in general get as much ass as they want.

  “Hey there!” I yell out, waving at them.

  Chloe gets to her feet, a smile on her face. Her daughter is about five years old, looking like she’s in kindergarten. She looks up at me briefly, then looks down at the ground. She looks nervous and holds
her mother’s hand.

  “Hey there,” I say to her. I give Chloe a kiss on the cheek and bend down on one knee to say hi to her daughter. “You must be Scout. Your mom’s told me a lot about you. I’m Dan. Nice to meet you.”

  “Nice to meet you, too,” says Scout, finally looking up at me a little.

  She’s a cute kid, especially when she smiles. She’s got her mother’s eyes and mother’s hair. There’s something very, very familiar about her. It’s almost like that feeling you get when you meet someone again that you haven’t seen for a long, long time and you don’t recognize them at first.

  “It’s so nice of you to host us,” says Chloe, giving me a hug as I stand up. “Scout’s never been to Philadelphia before.”

  “That so?” I say, winking at Scout, who looks down shyly at the ground again. “Well, we’re technically inside the city limits right now, although most people would call this the suburbs. But we can be sure to take you two girls into the city tonight to a nice restaurant, and maybe we can even see the Liberty Bell. Have you heard of that, Scout?”

  Scout nods her head. “In school,” she says, her voice quiet and shy.

  “Well I’m being a bad host already,” I say, trying to play the part of the good host. “I haven’t even let you in the house yet. Where are your bags?”

  Chloe shows me where the bags are in the car and I haul them all in, unlocking the door and letting Chloe and Scout enter first.

  Chloe

  Dan gives us a tour of his house. It’s a nice place, but it’s not very lived in, and I get the sense that he really hasn’t spent much time her at all.

  “Yeah,” says Dan. “I don’t spend a ton of time here, actually.”

  “Why not?” says Scout. She seemed shy at first, but as we walk through Dan’s house, she gets more and more comfortable with him.

  “Well,” says Dan. “I’m on the road a lot for work. They have us traveling all over the place.”

  “Why’s that?” says Scout.

  “Here she goes with the questions,” I say. In reality, of course, I try to encourage Scout’s many questions, but with people she’s just met, I try to tell her to tone it down just a little, since like all inquisitive kids, she can be a little overwhelming for some people. But Dan seems like he’s really good with kids, although I do get the sense that he hasn’t spent a ton of time around them.