Damon POV

I

was the male teenage version of jailbait. Or so all the older women told me. I remember one summer I was mowing Mrs. Walsh's yard and she invited all of her book club over to watch me mow the lawn. I only realized this after I had taken my shirt off and it would've been awkward to put it back on. In short, older women always loved me.

"You'll have all the ladies around your finger!" Mrs. Walsh once told me.

"You're going to be a stud" Was said to me by many 20-30 year olds who I thought were just saying that to get their lawns mowed for free.

Or my all time favorite, "Call me when your legal." from the older lady across the street.

Getting with girls my age was the problem. As an incoming freshman in high school I only had only made it to second base, far too inexperienced as I had hoped for. I had always been the muscley kind with the longish dark locks, but girls were always more interested in that hot skater guy or some guy that had the "Bieber" haircut. Now, imagine all of that pressure plus a brother who was going to be a senior at the same high school you were going to go too, and was the most popular guy at the place! It was insane. We could be walking down the street in the middle of no where and someone would walk up to him and say, "Hey, are you Stefan Salvatore?" Or "Aren't you that all-star quarter back from Mystic Falls?" Or the usual, "Ohmygod! You're like Stefan Salvatore! Ohmygod!" screeched at un-naturally high level.

Long story short, there was a lot to live up too. I tossed and turned in my bed, waiting for my alarm to go off. I was so nervous and the thought of Stefan wasn't helping me one bit. He was a self-serving prick; he isn't even going to drive me to school!

"Jackass.." I thought to myself while sticking my face into the pillow. My alarm blared all around me but with my head stuck face first into the pillow its annoying ring went right over my head, like most things.

I groaned loudly into my pillow, this was going to be a long day.

Elena POV

My first day as a freshman at Mystic Falls was supposed to be great, awesome, and most importantly carefree. Unfortunately, life had other plans for me, a life that included cutting and a lot of traumatic pain. I was dabbing foundation over my recent cuts and then going even farther as to place a plaid hoodie over my black tank top. I placed my foundation brush down and picked up my eyeliner pencil. I underlined my eyes lightly and walked to my full-length mirror where I checked over my outfit one more time, a pair of jean shorts, black tank top, multicolored plaid hoodie and my favorite converse, not exactly picture perfect but it will work.

I grabbed my bag pack out from under my vanity area and slung it across my back. With one strap fully secured on my arm I made my way down the stairs to grab a bagel and head to school.

"Elena, Sweetheart," Jenna said while stumbling down the stairs, "Let me drive you to school or maybe make you breakfast?"

She looked into my eyes with her hopeful ones as she attempted to make my first day seem a little more picture perfect. However, her extreme bed head and obvious morning breath was making that a tad difficult.

"Thank you so much Jenna but I kind-of want to walk." I said trying to sound considerate but I could tell how much she really wanted to be there for me. "How about afterschool you could pick me up?" I offered to her.

"That would be great Elena!" She said with a slight sparkle in her eyes. "3'oclock right?" She asked me.

"Yep!" I said forcing a smile onto my face.

"Ow, I really haven't smiled in awhile. I thought to myself."

I caught a glimpse of the clock and realized that it was 7:45 and school started at 8:00. "Crap! I have to wake up earlier." I thought to myself.

"Bye Jenna! See you at three!" I yelled back at her as I dashed out of the house and down the street. I heard the echoes of Jenna yelling something in my general direction but chose to ignore it.

I slowed my run to a complete stop realizing that the clock in the kitchen was wrong and I had a full half hour to get to school. I groaned loudly and wished that I could just go back to my warm bed and throw this bag pack off the side of a cliff. It was currently filled to the brim with all of my school supplies and shiny new textbooks and felt like it weighed a thousand pounds. I put my bag down on the sidewalk and pulled out my 1rst generation iPod touch. I had nick named it dinosaur because it was extremely slow and my domo sticker on the back was completely peeling off and looked almost fossilized. I chuckled to myself thinking about when I had gotten my iPod. It was a gift from my older brother Jeremy. He gave it to me before he and his girlfriend Anna went off to college in South Carolina. He had gotten over the accident almost completely, though he wasn't in the physical accident, he was in the traumatic emotional one that was left when my parents passed away leaving me and my older brother with our very novice to parenthood aunt Jenna.

"Enough Elena. This is a happy day. Extremely happy. Highschool will be the shit. Like legit, the shit. You'll get a boyfriend and make the JV Cheerleading team." I thought to myself in an attempt of calming myself down but utterly failing.

"Fuck me." I growled as I shoved my earphones in my ears and picked my bag pack up off of the concrete. I began to walk briskly towards the school when I was knocked off center by some idiot who slammed into me. I landed on my ass with my bag pack still on my back and legs spread out infront of me. One of my earphones had popped out of my ear which was suprising considering that he was incredibly built.

"Watch yourself Bro!" He said with his back turned to me. I sat completely checking out his ass. Between mourning your parents and social isolation, you don't get much a chance to check out a guy. It only lasted for a split second before he turned around and blatantly checked me out.

"Sorry sweetheart. I didn't see you. My mistake completely." He said with a charming smile, but looking in his light green eyes I could tell he was just hoping to get some where.

"Relax Elena and use your words. He's just being friendly. Don't be a bitch." I thought to myself.

I stood up and brushed myself off and replied, "Elena Gilbert," sticking my hand out to which he grabbed alittle roughly and pulled me towards him only to kiss my hand.

"Pleasure. The names Stefan Salvatore," He said with a Colgate Total smile, "Yes the highschool football star." He was a gloater. Great.

"Well I'm the one whose going to be late to school," I replied rather shortly and turned to walk away, " I'll see you later Stefan."

Just as I was beginning to walk away from him he touched my arm, more gently this time, and turned me to face him.

"How about I drive you? We have about 10 minutes until first bell. There is at least a 20 minute run ahead of you. Please?" He said with that obnoxiously white smile.

I let out a small laugh and agreed.

Something about this guy skeeved me out, and it wasn't just the over smiling or over gelled hair.