Hannah

"Where is the shy girl I met? Do you know how much power you hold right now, Hannah? Once he takes a look at what you are wearing tomorrow, he just might faint. I have to say I did not expect the plan to work out this way. I didn't know you had it in you girl, I'm impressed."

"Wait, we're really doing this? I'm actually supposed to walk in there and try to get him to fuck me? What if I don't want him to, huh?" I reply and the only response Jules gives me is a look displaying she knew darn well I wanted him to fuck the living shit out of me.

"Alright, I do, but come on. When I said that stuff to him, I wasn't in my right mind. I don't know what got into me. I've never done this kind of stuff before Jules, you know it is way out of my comfort zone. I flirt from a distance. Where I can't be heard and won't actually have to talk to people."

"Okay, do you find him attractive?"

"Yes." I respond almost immediately

"Then what's the big fuss? You are two consenting adults. It's not like you're getting married or something. It's just a small hook up. Everybody does it once in a while."

"Yeah, that's the thing. I've never done a 'hookup'. I don't want to mess it up, and I've only been with two guys. One of them barely even counts. I don't want to let him down with my inexperience,"

"You are going to be fine, girl. It's one time to let yourself do something outside of your box."

I sigh before replying, "I guess you're right. Where's the outfit I have to wear?'

"Glad you asked." She replies, getting up from the couch and hurriedly running to her room.

I follow behind her and by the time I reach the room, she is smiling happily as she holds a black dress. It appeared to be a regular work dress from the front, but the back was out and stopped mid thigh.

"So this time I want you to go all out."

"Wasn't last time all out?"

"No, that was what I would wear on a grocery store run. This time I want you to go all out, but not all out at the same time. For example, you can't look like you are trying too hard. Which is why I got you this bad boy," She hands the dress to me and I examine it more as she speaks. "A dress that makes you look sexy as hell, all the while not looking as if you're begging for attention."

"It's beautiful." I reply, smiling fake-ly.

I didn't hate the dress, on other woman I'm sure it would look amazing, but it just wasn't for me. No way I was going to tell Jules that.

"I know, right? Here, look at the shoes."

She pulls out a matching high heel and stands back up.

"This is what you'll wear. Along with a necklace and an ankle bracelet."

"Thank you, they're beautiful, but why do I need an ankle bracelet? It's just a hookup, right?"

She pats my shoulder and shakes her head, staring at me in disappointment. "You innocent little lad."

"Huh?"

"You'll thank me later, okay?" She responds and begins walking out of the room.

I shrug, not having a clue what she is talking about and follow behind. "Alright then."

"Good, now you need to go to sleep. I can't have you looking like a zombie on your first hook up. "

I scratch my palm and reply, "I'm not sure about his. I told you I made it sound like some stupid bet."

She grabs my shoulders. "Stop worrying! It's going to go great, alright? You're stressing me out and you know how I get when I'm stressed out. Do you remember my first year of college? The very first party I went to?"

"Yeah." I reply and roll my eyes. I had to stay up all night helping her get the glitter off her body.

She shudders in disgust before walking into the kitchen. I make my way to my room as a yawn escapes my mouth.

"Goodnight, girl!"

"Night." I reply, reaching my room.

I flop on my bed tiredly and groan.

Let's just hope I don't mess this up.

~~~

After finishing braiding my hair, making two braids come together into one, I slip the dress on. It looked better on me than I had expected, which helps me gain more confidence.

I decide to skip breakfast since Jules had to be to work earlier and only had a small amount of time to take me to work. About twenty minutes later, we arrive after getting the coffee.

"Shit." I mumble. My mouth goes slightly agape and I almost drop the coffee.

Micheal looked as if he had just gotten out of the shower and god was it an amazing sight. His face was clean- shaven, hair wet and curly, and to match it off, a freshly ironed black suit. How could he possibly look this good in the morning? Utterly insane. 

"Good morning, Ms. Brown." He greets me with a smirk, knowing the affect he has on me.

"Oh uh Good morning, Mr. Capone." I reply, placing the coffee on his desk. My breasts on display as I stand in front of him, waiting for him to give me instructions.

He stares at me for a moment before clearing his throat and going back to his usual unreadable expression.

"Your work for today should be on your desk. You can get started now."

I walk to my desk and begin working. Around noon I go to get lunch and come back to find, Micheal's first few buttons of his shirt unbuttoned and his hair moved around messily. His tie was also on the ground. I assumed he had been stressed and pulled it off.

Wow, did someone turn the air off, because it just got hot in here! That was so corny.

"Here you go, Mr. Capone, I have your lunch." I finally say, zoning out of my thoughts.

"Thank you, Hannah." He glances up at me as I walk back to my desk, swaying my hips a little.

While I am eating, I feel his eyes on me. I think about Jules' advice she had given me this morning. Popping one of the cherries in my mouth seductively and grin. I hear him clear his throat and am about to do another one, but he speaks.

"Stop, Hannah, stop." He says,

I turn around in my chair and smile innocently, "What? What am I doing? I'm only eating my lunch, boss."

"You know exactly what you're doing. This little bet or whatever is going to get you into trouble."

"Don't you want to fuck me, Mr. Capone?" I ask, standing up from my chair and going behind his chair.

I wrap my hands around his neck and he responds, "Hannah, you don't know what you're getting into." He looks at my hands that are now traveling down his chest.

"Maybe I do. Maybe I want you to ruin me for anyone else. Scream your name as I cum all over your cock. Maybe I do want you to fuck me until I can't feel my goddamn legs."

Geez, where was this bold Hannah in highschool?

I stand in front of his desk and he gives me a smoldering look. I swallow hard, becoming a little scared. The normal Hannah starts to sink in and I curse myself for being so bold.

Before I can take it all back, Micheal gets up from his chair and starts walking towards me. He sits me on his desk and spreads my legs. I try to close them, but his grip only becomes tighter. In almost an instant, my underwear is off and I gasp loudly.

"Micheal." I whisper.

He moves closer and groans. Before I have time to prepare, I feel his finger in me and yelp at the sudden feeling. As he begins to move faster, I throw my head back and moan. His movements grow quicker and soon he adds another finger.

"This is what you wanted, right?" He says as I begin riding his fingers, trying to find my release.

"You wanted to ride my fingers like this, baby?" He continues when I don't answer.

He adds another finger and I cry out in pleasure.

"Oh fuck!"

Panting heavily and feeling my orgasm come near, I look down at Micheal to see him already staring at me. He moves faster and begins hitting my g-spot repeatedly. I ride faster and we make eye contact as I find my release.

I collapse on the desk, panting heavily as I come down from my high. Mr. Capone stands up and I see him lick his fingers slowly as he moves my dress down slowly.

"My new favorite dessert." He says with a grin.

Oh gosh, that is hot.

I sit up slowly, trying to regain strength as he licks his finger for the last time.

"Mr. Capo-"

I am cut off when he lifts me up and throws me over his shoulder. I yelp in surprise. I try to remain as calm as possible as he walks.

"Put me down."

I didn't like people carrying me at all.

"Put me down, please." I try again and he continues to ignore me.

"Mr. Capone, put me down right fucking now!" I kick my legs on his back to try to get down.

We reach a room and he smirks, "As you wish." He finally replies, throwing me on the bed.

Is it weird that I liked being thrown on a bed?

My dress lifts up and I pull it down immediately as I sit up.

I exhale a deep breath, "Look Brick, I'm not this kind of woman. I don't know what got into me when I said that stuff yesterday, but I can't do this."

"Who is brick?"

Seriously, that's all he got from that? Are you serious?

"That's my stupid nickname for you. It doesn't matter. Did you hear what I said?"

I grow slightly irrateded as his grin only gets wider. "You have a nickname for me? What does it mean?"

He walks toward me as I respond, "I'm not telling you. Now what about what I fucking said?"

He doesn't answer, but instead opens my legs again.

"You talk a lot of game, Hannah. But now you're backing out as I thought you would. Like I said, I always win, beautiful." He says and rubs my thighs slowly. My breathing already starts to quicken at his touch.

Goddamnit Hannah!

I hated how competitive I was. What is this man doing to me? He's my freaking boss, and I've only known him for less than five months. But I did not want to lose against him. So I push the doubt, worry, and insecurity away before speaking.

"Is that all you got? I can do better by myself." I say, referring to what happened in his office.

Wow, what has gotten into me!

His eyes become darker in a way and he pulls my dress down a little. My dress bunched up around my hips as I sat with my legs slightly open and Michael standing between them. 

He takes my face in his hand, so we are staring directly at each other. The smirk is gone from his face as he speaks. "Sweetheart."

Breathing heavily, I reply, "Yes?"

He bends down a little so our faces are inches apart. "You're going to regret that."