A/N: I don't condone cheating. I just believe that Dean and Rory are meant for each other.
Also, I don't even watch this show anymore because it sucks now. But season four was still good, so I allowed myself to write this.
Please, review. I'm having kind of a blah few months and it would really make my day…
Disclaimer: I don't own it. I don't really know who does anymore. The writers and stations have all changed. Whatever.
Dean Forrester had been a virgin when he first met Rory Gilmore.
He always seemed to be attracted to the sweet innocent girls like Rory and Lindsay, and so his girlfriend back in Chicago had not been ready for sex at any point during their relationship. And Dean had been okay with that.
In fact, the moment he first laid eyes on Rory, he was glad he hadn't gone past second base with Sarah, because he knew that this was the girl he wanted to lose himself to.
Their first conversation had been awkward, but he enjoyed every moment of it. He knew immediately that this sweet girl was someone he could see himself spending a lot of time with. He flirted with her for a while, offering her free soda and making her that bracelet for her birthday. And when she asked him to go with her to the dance at her prep school, his heart soared. He pretended to be put out—what normal sixteen-year-old boy looks forward to a dance—but he was truly ecstatic at the idea of a date with Rory.
When the night was over and they agreed that she was his girlfriend, Dean felt as though he could take on the world and win with both hands tied behind his back. They'd had the expected ups and downs of any relationship, but he had fallen for her hard and fast. And even though she left him for Jess, Dean could never really get over her.
He had wanted her to be his first, but then he'd gotten married to Lindsay. He knew their wedding night hadn't been very good for her. He had heard that a girl's first time is rarely good; but it was surely made worse by his inexperience. It was better for him.
Running his hands through Lindsay's blonde hair, it had been easy to imagine the strands wrapped around his fingers as brown. He had never felt much of Rory's body, so if he wanted to pretend the one under him was hers, with his eyes closed, he had no real reminders that it wasn't. The hardest thing to imagine was the eyes. Dean had wanted for so long to look into Rory's deep blue depths and watch them widen as she writhed underneath him.
Waking up next to Lindsay the next morning, Dean immediately felt overwhelmed with guilt. He saw the small bloodstain on the sheets and felt bad for enjoying himself so thoroughly while she felt only pain. Then he felt even worse for thinking what he had been thinking the whole time. Was imagining his old girlfriend during sex with his wife be considered cheating? He wasn't sure, but he felt like it was.
He couldn't stop though. Every time he found himself on top of Lindsay in their queen size bed, he couldn't help picturing Rory in her place. Over time he came to accept it as a part of his life that would never go away, but then things got worse. Soon, he wasn't just imagining Rory in his bed; he was wishing it was she instead of Lindsay who was hanging that sweater up to dry, or sitting demurely on the couch with her feet tucked up under her thighs as she clicked through the channels on TV, or even taking the roast out of the oven. That was when he knew things had gone too far—Rory didn't and would probably never cook. If she tried to make a roast she would probably burn down their apartment.
He had to do something to get over this, but he couldn't figure out what. He tried to analyze the situation the simple way his parents had taught him: identify the problem and find the solution. It turned out the hard part was identifying the problem. He thought about it for days, before he realized it was simple: he missed Rory. The solution then seemed obvious. He wanted to see her again, to talk to her, to be friends at least. But could he do that? Could he just be friends with the girl who still unknowingly held his heart tightly in her grasp?
He decided to go for it, telling himself that it was to save his marriage with Lindsay, but knowing in his heart that he was just dying to see her again. And so he did, and it was great. But it didn't solve his problem. It only made it worse. He did stop imagining Rory in Lindsay's place. Instead, he just ignored Lindsay all together. He wanted to be with Rory all the time, she was addictive and he couldn't get enough.
Since he had already dealt with the guilt from his earlier fantasies, it was easier this time to move past it. Eventually, he stopped feeling guilty all together. He knew Lindsay had noticed that he was pulling away; she kept working extra hard in everything that she did, like she knew he was no longer trying to make their marriage work and so she was trying for the both of them. That had made him rethink what he was doing, but only for a moment. Once you're hooked on a drug, it's hard to stop.
The night he picked Rory up from the bar where she had been on a horrible date had started out wonderful. He had been so thrilled that of all the great people in her life, he was the one she wanted to come and rescue her. He like that she trusted him that much. He liked that she wanted him there. That's why it had almost made him crazy when she sent him on his way because Jess showed up. He was blind with jealousy, and he knew that was insane. He was married, and not to her. So he wasn't allowed to be jealous if she was with Jess, no matter how much he hated him. But it didn't matter that he wasn't allowed to be, because he still was.
He avoided her after that, finally realizing that what he was doing was wrong. It hurt, not seeing her anymore, but he tried to get past it. Then, at the opening of her mother's inn, he couldn't avoid her any more. And when she called his name and he met her gaze, he knew that he didn't want to. And then he had almost kissed her, and he had been sure that she was about to kiss him back, until Tom walked in and ruined everything. But that moment drained him of all his willpower, and now he not only wanted to see Rory again, but he wanted to kiss her for real and make his fantasies come true.
So when he heard she had gone back to her house to pick up some CDs for Lorelai, he took advantage of the opportunity to have a moment alone with her. He caught her just in time, and things were awkward at first as she was clearly embarrassed about the almost-kiss back at the inn. He was reminded of their awkward first conversation and he smiled, loving her even more for being so similar now to the way she was then.
He knew she would feel bad because he was married. But now that he saw he had a chance with her, he realized he couldn't be married anymore, he didn't want to be. So he told her it was over, and even though Lindsay didn't know it yet, it was. He would tell her when he saw her next that he was leaving her. It would hurt her, sure, but she'd get over it. She'd get over him. If he was still this in love with Rory then clearly he and Lindsay just weren't meant to be. As he leaned down to meet Rory in a kiss, their lips meeting for the first time in so long—too long—he felt a brief flash of guilt returning. He never thought he'd be that guy. The guy who cheats on his wife. But in all honesty, he had thought his wife would be Rory.
She deepened the kiss, which took him by surprise, and all the guilt left when her arms wrapped around his neck. This felt too damn right to be wrong. He walked her back toward her bedroom and laid her down on top of the covers, running his hands all over her body. And now that he knew what her body felt like, he knew he could never pretend that Lindsay was her again. And he didn't want to. He didn't want to pretend. He wanted the real thing, and at this moment he had it.
Soon, their clothes were gone and he saw all of her. She was so beautiful; he couldn't believe he had gone without her for so long. He watched her blue eyes widen as she writhed beneath him, just like he had always wanted, and he knew that no matter what happened in the future, this girl would have his heart forever.