Chapter 1: Preparations and Strange Encounters

"Ugh… Mom, I don't get why I have to go to this stupid thing. Why can't I just go out and let you take care of it?"

"Elena, We've been over this. Giuseppe Salvatore has two sons, Damon and Stefan. Jeremy will keep Stefan occupied, and you will handle Damon."

"Look Mom, I met Damon at school. He's a player. He's already sleeping with Caroline Forbes."

"I didn't say you'd have to marry him, god Elena! Just keep him occupied while the grown ups discuss business."

"Please tell me that Aunt Miranda and Uncle Grayson will be there at least."

"Of course they will, Grayson has as much to do this as your Dad does." I roll my eyes and I keep looking for a dress to wear to this stupid work party.

To keep it short and simple, We'll be hosting a corporate party to attempt and unite Salvatore Corporations on the West Coast and Gilbert Corporations on the East Coast and make a huge amount of money doing god knows what.

I look at a dress that would expose enough cleavage to keep Salvatore drooling but still keep me elegant. I take it off the rack then I head over to the register with my mother, Isobel. She's always too busy to spend time with us, even when I was a little girl. I always spent time with my Father, John, who always made time for us, my little brother Jeremy and I.

After buying the dress and the shoes, Mom and I head out to dinner. "What does Damon Salvatore want with me anyways?"

"He mentioned to his mother who mentioned to me that he's seen you around the halls and he finds you extremely attractive. He said that he tried to hang out with you at the bonfire, but you wouldn't."

"If by 'hang out' he meant 'I tried to get in Elena's panties', then absolutely, I said no to hanging out. That's why Aunt Miranda came to pick me up." Her jaw drops. "He tried to sleep with you?"

"I mean, it's not all his fault, I was a little drunk and wearing my cheerleading uniform and after I broke up with Matt, I was… Encouraging." She raises an eyebrow then the waiter brings our salads. "Elena, what do you mean by encouraging?" I sigh. "I was dancing with him… Grinding, more or less and things got heated, he pulled me away from the party and we made out. That's all that happened. I pushed him away, he got pissed because I wasn't going to have sex with him, then I called Aunt Miranda. I went home and fell asleep. We haven't spoken since then. He's sleeping around with Caroline Forbes, which I'm not sure I'm okay with."

"Why, because she doesn't deserve the STDs?"

"No, because he doesn't deserve the STDs." She shakes her head while laughing then- what are the odds- Damon and his mother strut through the door. I take a bite of my salad. "Isobel!"

"Lily! How wonderful it is to see you!" I look at Damon for a moment and he looks down at me, a smirk on his face. He slips a piece of paper down on the table and I take it quickly. "Would you two like to join us? My treat."

"Thank you Isobel." Damon sits down next to me and my heart begins to pound. "So Damon, what kind of activities are you into?" He rests his hand on my thigh and begins squeezing gently, making sparks fly through my body then to my core. "I really enjoy football. I'm actually the quarterback and the captain."

"Interesting. You know Elena's the captain of the Lady Timberwolves? We were thrilled to get the news."

"I did know. I always see her cheering a lot for the games. And look at her, how could you not put her in one of those uniforms?"

"I thought the same thing." He unbuttons my jeans before slowly pulling the zipper down. I drop my hand down off the table and I guide his hands where I want them, making him smirk. He covers his mouth with his hands then without warning, he thrusts a finger inside of me. I bite my tongue to conceal a moan. The waiter comes up to us. "To drink, or are we all ready to order?"

"Can I get a burger? Extra juicy, I don't like my burgers dry." Damn him and his sexual innuendos.

"For you ma'am?" He begins pumping his finger lazily. "Yes, can I get the spaghetti?"

"Meatballs or Italian Sausages?"

"Italian sausages thank you." Damon inhales and I can see him grow harder. I smile, seeing my innuendo work perfectly against him. Our Moms order then they chat amongst themselves. "Elena, Damon, we'll be right back, I just have to run out for a cig." I nod then Damon leans into my ear. "Do you like teasing?" He hits that sweet spot and I moan softly in his ear. I bite on his earlobe gently and he thrusts faster. "Why don't I finish you so you won't get caught by Mommy?" He rubs my clit furiously and I bite my lip, my body filled with the sweet sensation of pleasure. I didn't think he'd be able to make me feel this good with just his hand. I know what he can do with his… other body parts, and that was probably the epitome of everything.

Flashback- 6 Months Ago, a little ways outside of Mystic Falls

I take the shot, feeling the throbbing sensation of my heart become less as I numb the pain. I look over to see a new guy staring at me. The alcohol in my system is making me brave, so I walk over to him. "Hey stranger! I'm Elena, you look like you're in need of some company," I tell him. He smiles and my heart skips a beat. "I'm Damon, and yes, I'm kinda lonely." My favorite song comes on over the speakers. "I love this song! Dance with me, Damon?"

"Oh no, I don't dance. I hate dancing." I lean up into his ear. "I bet you a night with me that I can make you love it," I whisper. I pull back and his eyes darken then he smirks. "So what is the bet?"

"If you win, then you get a night with me. If I win, then I get a night with you." He pulls me into him by my waist. "It sounds like we both win either way so why don't we go into this room in the back and dance a different tango?" I feel my core heat up then I nod. He takes my hand and leads me back. He closes and locks the door then kisses me. I wrap my arms around his neck and he wraps his around my waist. I reach down and grab him through his jeans and he groans then picks me up and tosses me down onto the bed. He pulls my cheerleading uniform over my head before running his hands up and down my sides. I tug his shirt off then as he takes his pants off, I get my bra off. He stares at me for a moment before kissing me again. He crawls off of me for a moment as I walk over to my purse that I left in here with Katherine's stuff and I pull out a condom. He chuckles.

"I don't know what size Donovan was but that won't fit me, baby." My throat tightens in lust and I shimmy out of my barely there black lace panties and he gets his boxers off. I grasp him in my hand then I switch our positions. He leans against the headboard and puts the condom on, then I tease myself with his tip. Without warning, I sink down onto him and his mouth opens. I throw my head back and he sets his hands on my waist. "Damon…" I moan. I begin moving and the way he fills me and consumes me makes all of the blood rush to my core. He moans and I slam down on him harder. "Did you like the way I danced, baby? Is that what made you so hard and ready for me?" He buries his face in my neck and I feel his lips against my ear. "So tight and wet… How does it feel for your walls to be stretched perfectly for me? To have your tight walls wrapped around my thick, hard cock?" I moan and begin moving faster, bouncing on him like my life depends on it, and I think it does. He slams me down on him again and again, my clit hitting his stomach since he's sitting up.

SMACK!

My ass stings for a moment but quickly dissolves to pleasure, every delicious vibration going straight to my core. He flips us around and stuffs some pillows underneath me. Matt was never experimental, so he always came first and I would have to finish myself. But with Damon, I don't see that being an issue.

He thrusts into me again, this new angle allowing him to get that spot Matt could never get. I clutch at the sheets, my senses going haywire. He groans and I claw at his back. He flinches when I accidentally draw blood, but then moans and speeds up his thrusts. "Damon, I c-can"t…" Stars burst behind my eyelids and I cry out as I'm attacked with the most earth-shattering orgasm of my life.

End of Flashback

I whimper softly in his ear as I release down onto his hand just from the memory. He licks his finger gently and leans into my ear. "Still a perfect fit for me. Admit it, I ruined you for other men."

"If I tell the truth you can't tell my mother. She isn't even aware that we've had sex."

"Mmm… Deal." I take a deep breath. "Yes, you did ruin me for other men and rock my world, but you are hooking up with a sophomore."

"Wrong brother. Stefan is with Barbie, I have had my eyes on you for quite sometime now."

"It's only been a month since we were together."

"Why don't we go out tonight and lessen the time?"

"Last time we slept together I was plastered. So what makes you think there will be a second time?"

"Because it was too good for a one night stand. I'm on the level that we should be friends with benefits, I'll even act like your boyfriend in public."

"Interesting offer. I'll let you know at my father's party."