The Playboy's Bet

I open my eyes one by one trying to avoid the bright light that is streaming through the windows. I stretch every perfectly formed muscle in my body. I look on over to the blonde that is spread all over the bed next to me. There is a big smile on my face, and I am feeling great.

If there is something I do well, then it is rolling out of bed the morning after. Now by rolling, I mean getting my ass out of the bed I found myself in the night before. I live by one rule, and that is, I do not take girls home. Yes, sometimes I find myself in some tight spots and rough places but never once will they ever come over to my place.

I am meeting the boys at Crazy Beans this morning, so best I get my ass back home to shower and shave. We meet up at the coffee shop around the corner from the office as a routine every day, mostly for kiss and tell the morning after. This morning it seems I am the only one telling since they both went home empty-handed last night.

An hour later, I walk into the coffee shop where they are already waiting.

"Look what dragged his ass out of Ava's bed," Brody hollers over the crowd.

"It was not Ava; it was Amé."

"Same difference, bro. What is up with the third in a row?"

"I don't know what you are talking about."

"Don't act stupid; you know exactly what I am talking about."

"What is a third in a row any case?"

"It's the third time you have taken her home," Mason says as he joins the table.

"She has taken me home." I correct him.

"Whatever, it is still the third time, man."

"She is a nice girl."

Brody nearly topples his espresso over as he nothing but laughs at me. "And the whole of Myst thinks that too."

Pulling my worst frowning face at him, I place my order with the waitress.

"What is that supposed to mean?" I ask him in utter annoyance.

"That she is not the kind of girl you go home with for the third night in a row."

"And what kind is that?"

"The chick likes the fun, the lifestyle, she does not like you. She is playing with you."

"The hell with that. I am done with her; nobody plays me. I am the only one doing the playing here."

I see Mason staring at me with a big smile on that wise-ass face of his. "If you want to do a third, even a fourth, then you need a decent girl."

"I can get a decent girl."

Brody joins Mason in his damn teeth parade. "Can you get a decent girl that would want to take you home with her?"

"How difficult can it be to pick up a decent girl and go home with her?"

"Not as easy as what you think," Mason now says to me.

"There is plenty of them at the club."

"I said a decent girl, not a decent slut." Brody says as he gets this big wide-eyed look on his face.

I don't know where this is going, but I think I should keep my mouth shut while I am still ahead, but that male part of me who loves a challenge is not bound to back off now.

"I say let's place a bet" his wide-eyed look is now turning serious. "You can't get a decent girl that will take you to her place."

And, of course, Mason tries to push it further. "I am going to push it up; you can't get a decent girl to fall in love with you."

"Whoa there," I raise my hands as I pull back into my chair. "Fall in love with me?"

"Yes, the real you," Brody says. "Not the one with the money or any of that shit. And you not paying some chick to pretend she loves you either!"

"You asking me to get someone to fall in love with me for real?"

"Yes," Mason confirms. "I say half a mill that you can't."

Then Brody adds, "I raise it with another half mill that you won't."

I match the stupid smiles on their faces even better. "I can get any decent girl out there to fall in love with me. Many decent girls already do want to be in love with me."

"Are you in?" Brody asks.

"I am in. How long do I have?"

"I give you a week to meet the girl," Mason says.

"And I give you three months for her to say the words," Brody adds.

"Game on! Now, where do I meet this girl?"

"You are supposed to figure that one out yourself."

"Come on, a little help here would be great. I don't know everything, well I almost do."

"Don't tell me that you have never had a decent girl before?" Brody laughs, finding his own wise-ass comment funny.

And who would Mason not be if he cannot add his own five cents? "His decent less ass has never even been in love before."

"Oh, you got to be kidding me," Brody's laughter echoes the room. "I going to raise the stakes. Another half a mill says you fall in love with her."

"You have two chances of that happening, slim to nothing all. No women will put me under her spell." I think I should officially shut my mouth now; if I continue talking, who knows, I might be getting engaged next. I don't think I realize what my dumb ass has let himself in.

But my dumb ass could so do with a whiskey right now, but I got a meeting in an hour. I call the waitress on over to bring me a strong cup of espresso.

"Yes, sir, what can I get you?"

"Please don't call me, sir; I am probably the same age as you. Not that I am saying you old, I just..."

"No problem, I get what you mean. What can I get you?"

"Double espresso, please."

"Sure in a second."

She walks off to the counter to get the order. I can see these two staring at her ass. Yes, it is tight and just the perfect handful. My eyes can't help but wander down her sculpted legs. Watching her move in those reds stilettos makes my heart race and my blood boil in places it shouldn't. The thought about her and that empty table definitely crosses my mind.

Brody sees me watching her so intently. "There you go, what about that waitress?"

"Come on; I am not seeing a waitress."

"What is wrong with it" Mason looks at me, disgusted as he asks. "She looks like a decent girl?"

"It just feels weird; I have never seen myself going out with a waitress before."

"Don't judge so easily; she probably thinks you are a jerk."

"Okay, it's her then. That is the girl that I will get to fall in love with me."

But it is not her that brings me my coffee; it is another girl. "Here you go, sir."

"Thank you. Sorry for asking, but what happened to the other waitress?"

"Oh, that is not a waitress; that is the owner; she just helped out cause I was on the phone."

"The owner? Has she left?"

"No, she is just back in the office."

"Is she here every day?"

"Yes, she is here most of the days."

"That's great, thanks."

I turn back to the table. This is going to be easy; I will just come to drink more coffee during the day. My head might just be buzzing more, but if it gets the girl, then it is worth a shot of extra espresso a day.

I do not see her again in the shop after that. We finish our coffee and head our different ways. Usually, I'd be going with Mason, but I have a meeting on the other side of town. I take the short fifteen-minute walk; my mind keeps returning to the coffee shop owner.

"She will be mine even faster than she thinks."

I rush through my meeting, not really concentrating at all. I need to close this deal, but I know it will really close itself. I am the best at what I do, I could have done this with a conference call from my office, but I felt like showing face. As with these things, they bring you countless amounts of coffee just to keep you awake. All I can think about is going past Crazy Beans to get real coffee on my way to the office and, of course, to see the owner again.

I leave my meeting at noon and make my way back to the coffee shop. I decide against asking Mason to come over; I know he would be teasing me for being here. I myself don't know why I am here. But if I want to get this girl, I should start doing it now.

And then there is that part that does not want to look stupid in front of his friends when she turns me down.

I sit at my usual table. I take my phone and run through my emails and also send a message to my assistant that I would be in a bit later. Finally, the waitress shows up.

"What can I get you, sir?"

"I see you are still calling me, sir."

She bursts out laughing. Now, if a relationship were something that I really wanted, then I'd say that she has a beautiful laugh, one that wants to make you burst out laughing with her. And then there is the way her smile plays around the corners of her mouth that makes you want to smile back at her.

"Double espresso?"

"Yes, please. Sorry, what did you say what your name was?"

"I did not..."

She disappears behind the counter and a few minutes later appears with my cup in her hands.

"Do you mind joining me for a minute?"

"I don't normally do, but I see the waitress is back."

She takes her own cup of coffee off the counter and sits down at my table.

"Your waitress does disappear a lot?"

"Oh, she is having problems with her boyfriend."

"And you allow her to let it interfere with her work?"

"We all have our problems; if I need her help one day, I know she will be there for me."

"That is a different way of thinking of things; Mason would never dare to bring his girl problems to work."

"You men are different from women, we share everything, and we help each other; we like sisters and friends at the same time."

"The only thing men share is their beer and their stories about getting laid. We could care less if you are having a problem with your girl."

"You definitely nailed that one."

I stare at her a bit too long than I should do, but she seems like a nice girl, in fact, the perfect girl. I need to see her again; we have to meet outside this coffee shop. I am going to have to ask her on sort of date, am I going to pass out, the possibility is there, do I know what I am doing, definitely not.

"Do you ever go to Myst?"

"Jo is practically part of the furniture."

"Is Jo, your boyfriend?"

She bursts out laughing again.

"No, Jo is my business partner and my best friend. She is feeling ill today; that is why she is not in."

"Maybe you and Jo can join us next time you are around."

"I am afraid I don't go out with clients."

"You sure you can't break the rules just once?"

"Unfortunately, no rules are getting broken here, but if you will excuse me now, I need to get back to work."

"Wait!"

I take my wallet and take out one of my business cards. I hand it over to her.

"I'm Damon. If you ever change your mind. We almost always there."

She looks at my business card then looks at me. I can't read her face; I have no idea what she might be thinking. Did I blow it before it even started? She places my card down on the table and looks up back at me."

"Damon Chase, I have heard about you. Bad boy and heart breaker and some things I don't think are fit to say out loud in public."

"You should really not believe everything that you hear."

"If there are so many, it is hard not to listen."

"You are listening to the wrong things and the wrong people. I am really a good guy."

"Yes, really good at what you do."

Ouch...I did not see that one coming. She is beautiful and a decent girl, I like that, but she is also hot and cheeky, I like that even more.

"Please just consider it."

"As I said, I do not get involved with clients."

As she walks off, I can't help but smile. For a minute there, I thought that she would have said yes. I thought that she might not have heard about me and my reputation. I have probably tried picking her up before or, even worse, her sick friend. With me, absolutely anything is possible.

A few minutes later, she comes back with my tab. I place the card that she left on the table with the paid slip and say goodbye.

"It was nice to have met you; I will be waiting for your call."

She hands me my card that she has picked up off the table.

"Damon, it is nice to have met you; I will see you around."

I leave the coffee shop and make my way to the office. Still holding my card in my hand, I look at it and smile. This is going to be a challenge, and I like it. She is the perfect girl; she is not some easy clueless girl. I am going to make her mine before the three months is over, but to get her to say yes in a week is going to take some work.

Yes, this is most definitely a stupid bet, we make these stupid bets all the time, but I will be honest that this is by far the one with the highest stakes. I am not talking about the money. Someone is losing their heart, and I am making sure it is not me.

What have I learned? Do not give your business card to a girl you are trying to ask out. I mean, really, what was I thinking? Who the does shit like that anyway. I am officially the worst potential date ever.

I need to get expert advice on this. I have absolutely no idea what I am doing, and getting this advice; I am going to need to bribe her. I quickly stop at one of the cafes on the corner before making my way into the office.

This cafe sells almost any type of chocolate that any girl's heart can desire but what they are best known for is their wide range of Italian cakes and pastries. Death by chocolate is what the girls at the office call them. And of course, they make the best damn latte this side of town. I grab my order and head across the road to my building.

Chase Enterprises is a jack-of-all-trades Enterprise Company that offers hardware and software solutions to whatever your need is. It started off as a hobby in my college years and turned into one of the top three enterprises in the country today.

I cross the lobby as I enter and take the elevator to the very top floor. I brace myself as the door opens.

"Morning...oh, it is afternoon... Afternoon Mr. Chase."

"Afternoon Tajsa."

"You have a couple of messages, well more like thirty, eight is from a Miss Amé. There is a parcel from a Miss Ava and flowers from your usual unknown. I had to cancel your two o'clock because you are late. Your suites are at the cleaner. Maggie said she refuses to clean your white shirts with the lipstick stains on. Mason has been looking for you, twice and I am supposed to remind you about drinks at seven downstairs at the bar. Have I forgotten anything?"

"Yes, Tajsa, you have."

"And that is?"

"Breathe, woman! You make my head spin."

I love Tajsa to bits; yes, I should not say that about my assistant, and no, I have not slept with her, and no, I have never tried. She has been there with me since day one that this started. She is a loyal employee and a good friend.

"Oh, before I forget, your latte and those chocolate Petites."

"Thank you, Mr. Chase, after having to endure that Amé eight times, I really deserve these."

"Sorry about that. I will give her a call, and I want to ask you something whenever you got a minute."

"Well, you might as well do now since I am breathing for a few minutes."

I walk into my office, and she follows me, taking a seat on one of the couches.

"So what's up?"

"Now, don't get cross."

"I am already cross because you are telling me don't get cross. This has to be bad, and those other two are involved in it."

"You know us all too well."

"I did date your brother for nearly four years."

"Well, we kind of made this bet."

"Oh god, the last time you guys made a bet, I had to bail your asses out of jail."

"It's nothing that bad."

I continue to tell her about the silly bet we made at coffee this morning and then further telling her about my piss poor attempt to ask the girl out only to end up being booted under the ass later.

"That serves you right. Are you guys bored or just plain stupid? Wait, don't even answer that."

"Stop being so dramatic, Tajsa. Are you going to help me or not?"

"What is in it for me?"

"Says she that just asked me if I am stupid."

"She wants a day off at the spa, a new pair of Jimmy Choos and a Gucci bag."

"Anything else, princess?"

"Well, there is this dress, but let's see how it goes."

"First, I want to see what the girl looks like."

We pull up a picture that we find on the website for the coffee shop; she is even far more beautiful than I remember her.

"You got to be kidding me. You are hot, but your hotness ain't getting that."

"Now you sounding just like your damn ex."

"For once, the damn thing has got brains, well, only half because his stupid ass is betting on this thing too."

"I will make it two pair of Choos."

"Make it three; then we got a deal."

"Deal, I will throw in that dress too."

"Oh, we are desperate, aren't we? I wished that I recorded it."

"You have no idea what that just sounded like."

"Get your mind out the gutter, Mr. Chase."

"We still have five minutes, don't call me that."

And this is where you go, like what the hell. Tajsa and I at least twice a week share Petites and coffee and just sit on these chairs and chat. We chat about absolutely anything for half an hour as friends, no boss or assistant, just as friends, and after that, we get back to work.

"Okay, let's try the easiest first. When you see her next, ignore her."

"What? How is that supposed to work?"

"Women hate being ignored. She knows you want her; now make her think you don't want her anymore. It is going to drive her crazy; she is going to make you want to notice her."

"Is that all?"

"Yes. And for god sake, do not sleep with someone else while you are chasing her."

"Then what do I do?"

"Don't ask me, use your hand or whatever it is that you guys do. You won't die without it for a week."

"That is what you think."

We finish up our latte, and both return back to work. I take a seat at my desk; after sifting through email after email of applications for a new senior position, I finally give up. I am not focusing; my mind is consumed by this girl.

I check the time and decide to call it a day. It is a few minutes before seven, enough time for a quick change, and then head downstairs to meet the boys at the bar.

I get to the bar where they are already waiting.

"What's it with you being so fashionably late?" Mason is the first to greet me.

"How do you know what fashionably late is anyway?"

"Looks like we spent a few minutes longer in front of the mirror too." Brody, of course, has to add.

"Do you even know what a mirror looks like?"

"Someone seems a bit tense tonight," Mason says.

"Yes," Brody agrees. "What's got your balls in a knot?"

"Nothing. Can we skip this shit and go to the club?"

"I am not going to the club so early," Brody snaps at me while pulling out a chair. "Just sit your ass down and relax."

"You sounding like your ex now."

"Oh, I know what's wrong; he had some couch time with Tajsa today."

"What did the sassy assistant have to say?" Mason asks.

"Since when is she sassy?"

"Since he punched me the last time I called her hot."

I turn to face Brody. "Since when do you care?"

"It does not mean that because she is an ex that I share."

"You have no idea how bad that sounds. And in any case, I don't allow office affairs, so you have no problem there."

We stay at the bar for another three more rounds. As nine o'clock comes around, we all head to our cars and make the ten-minute drive over to the club. Myst is like a third home; if we not here, then we either at home or the coffee shop. It has been our playground from the first time we came here, back when we were barely legal. And tonight, it seems to be packed.

I meet up with the boys in one of the booths. Trust that on a night like this; I have to keep this zipper shut.