As you can see, I'll probably keep alternating between Jess and Rory with maybe a little Luke and Lorelai POV thrown in later on. If Jess seems a little OOC, it's because of the influence of my very own Jess. The bad boy that's hard on the outside, soft on the inside and well worth it. I wanted to give Rory the happy ending that I never got; it is just not going to be an easy journey. I always found that, the harder the path the better the reward.

Disclaimer: I own nothing, no matter how hard I wish I did.

Jess POV

"Hey Jess, wait!"

I look up and see the blonde girl that sits behind me. I can't remember her name and I really don't want to. For weeks now, I have been taking these GED classes and I wouldn't know the teacher's name if it wasn't written on the board. I do not have time to socialize, I have to work and study, I have to make things right. I can see the blonde's friends, also blonde, smiling at me on the other side of the classroom. They see me look and start whispering and giggling behind their hands. What is this, junior high?

"Hi," she says, smiling. I just stare at her when she doesn't continue, I groan. I'm gonna have to talk to her, her smile is getting annoying and I wish she'd just go away.

"Yeah," I say in a tone that's very Luke, a tone saying get to the point and make it fast.

"My friends and I are going to grab something to eat, there's this great place just down the street. Wanna come?" Her voice bordering on what I can only describe as bubbly, but the innuendo within the question nauseated me. I grab my books before I answer her, I don't want to answer her but she looks like she'd follow me if I just walked away.

"Thanks, but no thanks," I am walking away before I even finish. I pick up the pace once I hit the street, heading back to the room I rent. I stop at the pizza place, next door to the motel I'm staying at, and grab food for the night. My mind is on an assignment, wondering if I will be able to finish it tonight. I'm pulling doubles all weekend, trying to save the money to get back to New York. At the rate, I'm going I should finish classes in a month and a half and have enough money a month after that. I'll have the money then all I will need is the courage. Will I be able to handle being that close to her?

Coming in the door, I put thoughts of Rory and anything remotely close to Rory out of my mind. If I dwell on Rory, I will never finish my assignment tonight. I need to focus on my work. Sitting at a makeshift table in a cheap motel room eating pizza and doing homework on a Friday night, is not would ever have pictured myself doing, but that was before. Before I failed them, they were only people to show me kindness in a very long time. In this very room, I started making the plans to change, not just myself but also my situation. In this room, I decided that I enjoy writing, so much that I now aspire to be a writer. My English teacher told me after I turned in my first essay to her, that I have the potential to be a very good novelist if I choose to be. The owner of the bookstore where I work holds evening writing classes during the week. Before I leave, I plan to take a few, learning the basics. I have the ideas; it's just getting them out of my mind and onto the paper.

I glance at the clock after putting my books away, it didn't take as long as I thought it would to finish. I pull out a book to read until I fall asleep. I didn't even get to crack the book before my mind turned to other things. Things I only allow myself to think about, when I am in bed. At first I tried blocking it all out but that ended with a weeks worth of sleepless nights, so I compromised by letting my mind wander. My only thoughts are for her when I'm lying here, I can think of all the shit I pulled, about how much I fucked up. I sometimes wonder if things had been better if I opened up to her, if I hadn't been in such a fucked up place in my life, would I still be by her side. My greatest regret is leaving her, for disappointing Rory.

I let my thoughts drift to the night we spent together, the night we made love. It had been after I lied to her, yet again. She had asked about school that night at Lane's and I lied to her. The next night, she told me she was ready, I didn't agree right away. I wanted it to be special for her, I suggested waiting until prom night, and she laughed and said she did not want her first time to be a cliché. She was so confident in her decision and I was completely terrified, I found this amusing later on, it was as if we reversed our roles. She was perfection in every possible way, she responded to my every touch. Her body became a finely tuned instrument and I played it to its fullest. Her taste was unbelievable, well worth the coaxing to get her through her embarrassment. If we were doing this, we were doing it right and I was going to cause her as little pain as possible. She was so tight, I used my fingers to stretch her as much as possible while I nibbled and licked her to orgasm.

I looked down at Rory; naked and flushed on my bed she was beautiful. I slipped on a condom and crawled up her body, kissing her open mouth letting her taste herself. I wedged myself between her thighs. Pulling back from her lips, I opened my eyes to meet her suddenly clear blue gaze. Her blue eyes focused on mine she nodded her head, answering my silent question and still I hesitated. "Rory are you sure?"

Rory did not answer me this time; instead, she wrapped her arms and legs around me pulling me down into her. I reached her hymen and pulled her into a deep kiss before pulling my hips back and plunging through the barrier. I swallowed her cry, and froze deep inside her. I pulled out of the kiss to look at her, she had her eyes screwed shut, and tears had escaped the corners. I felt her inner muscles relax around me and Rory began to test the strength of those muscles, squeezing me a little harder each time she did it. I began to pump into her slowly, until she started matching me thrust for thrust. I bent low to whisper in her ear. "You are so beautiful baby," I trailed my tongue around her ear and she shivered. "I'm gonna make this so good for you, I promise." I was losing control fast, she was so wet and so tight she was strangling me.

"Jess...feels so good," she purred into my mouth as she pulled me into a kiss. Shifting my hips to angle my thrusts, I knew I had hit the spot. Her moans grew louder when I slipped my hand between us. She exploded around me, clamping down on me like a vise.

"That's it baby," I whispered in her ear. "Cum for me, baby." I pumped into her a few more times before loosing all control. I thrust deep inside her and let myself go, saying as I came, the truest words that have ever come from my mouth. "I love you, Rory."

"I love you, Jess," she whispered before dosing off in my arms. I pulled away from her to get rid of the condom. She loves me, I could not believe it, I was flying and then it hit me. Rory Gilmore loves me, she gave me her virginity tonight and she loves me. I looked at her; peacefully sleeping on my bed, sitting on the edge I studied her. How could she love me? I've lied to her; I would not open up no matter how hard she tried. I brushed a strand of her hair away from her face. She's so beautiful and she is mine, and that scared the shit out of me. I sat there thinking for over an hour and I still could not figure out how I got the girl. She left Dean for me, she chose me, and she loves me. We had only been together for a few months and yet I love her with my whole heart. I crawled back into bed beside her and I just held her.

Annoying beeping invaded my slumber and I got up to shut the alarm off. I don't remember falling asleep last night, but I know I dreamt of Rory and the most beautiful blue eyes. I always wake up haunted by the love shining in her eyes for me, followed by the hurt that I saw after Kyle's party. I shiver at the thought; I knew what I was doing when I tried to start something in the bedroom at the party. I was trying to get her attention off me; I didn't want to tell her that I had failed her and that Luke would probably throw me out now. I knew she would not make love to me there and I took advantage of that knowledge. Her tears burned my soul and I wanted to tell her everything, but when I followed her out and saw her crying to Dean. I was done, he always seemed to be there and when he rushed me, I was happy. Anything to take my mind off the deep shit I was in.

From there things happened so fast, my need to apologize to Rory and tell her the truth. Then Jimmy shows up and throws my world so far off its axis, not even Rory could pull me back. Luke throws me out and I can see the disappointment all over his face. I failed the only man in my life to give me a chance and I knew I could not face Rory. I did not want to see that look on her face too. So I did the only thing I could, the only thing that Mariano men seem to do best, I ran. Now I don't know if I'll ever find my way back. Back to the only woman I will ever love.

Looking at the clock, I take a quick shower and get dressed. Stepping out the door into the bright California sun and taking one-step closer to fixing everything that I fucked up. As I head to work, I think of Rory, of her smile and her laugh and I wonder if I will ever make her proud. Will I ever be good enough for her? Can I change enough to be the man she deserves? Will I ever get her back? I guess we will see.

When I get to work, I leave Rory's smiling face outside. Repeating in my head, what seems to have become my own personal daily affirmation. I love you, Rory and I will see you soon.

A/N: Coming up next, telling the Gilmore's and postponing Yale.