The first time she admitted to herself that she was in love with Damon, was that night he saved her.
She always knew that it was there, it was something she never really admitted. Something she refused to admit because she knew that as soon as she did, it'd all be over. Whether that meant a darkness would take over or not, she wasn't ready for the backlash. The anger that Jeremy would have. That Matt would close off and avoid her forever. That Bonnie would figure out any way possible to make her life a living hell. Hell, even admitting it to Stefan would hurt; knowing that the one person that helped the little girl realize that she needed to move on would physically hurt over her. The thought made her uncomfortable to say the least, but it was something that she had to do. She couldn't keep lying to him. Something between her and him changed that night on the bridge. The little girl, the fragile, human Elena that she used to embody was gone, and the worst part was, was that she didn't want her back. Even after hearing him tell her that there was a cure, there was nothing that she wanted more than to have his arms around her. Because even if she had the cure, the things she felt for him would never go back to the way they were. Just like the feelings she had felt for Stefan would never grow past where they were now.
The first time she said it out loud was a few weeks later, at the Miss Mystic Falls pageant. Even after all the convincing that Stefan had attempted, nothing made more sense than her soft gaze on Damon. The way he looked at her like no one else mattered, and that anyone who dared to take her away from him would be killed in a heartbeat. She would've never admitted it to herself back then, but now? Now there wasn't anything more attractive than his stare. She walked down the stairs, looking back at him before uttering those four words. We need to talk. Of course he obliged, following her up the stairs as she led him into a room as she looked over at him, her gaze on his. There was no backing down as she uttered out those words. It was everything for him not to kiss her, and for her as well. She wanted to, hell, there were a lot of things she wanted to do to him. But all seemed too forced. She wanted it to last. To mean more than just a quick rebound from the younger Salvatore. He didn't question her, and she walked away, leaving him in the room to process his thoughts, as well as her own.
The first kiss that mattered was later that evening, back at his house. His had his hands around her hip, and his other hand intertwined with his as they danced near the fireplace. She kept her gaze on him at first, her breathing hitched as she tried to figure out what exactly she was doing. If this was right. But then everything made sense when he looked at her. When he told her he loved her too. That his words still meant the same after all this time. After all the times she denied, no, refused to believe that it was true. He pressed his lips against her own, waiting for the retaliation that he was so used to by now. Except it never came. She moved her lips against his own, swallowing hard as her hands moved to wrap themselves around his neck. She closed her eyes, pressing deeper to prove that she wasn't going anywhere. Where else would she go? There was no where else she wanted to be than in his arms, with her lips pressed against his own.
The first time they made love was a few weeks later. He didn't have to pressure her into anything and she didn't have to jump him. They had it planned, sort of. She told him that she loved him again, and he followed it with a kiss. With every brush of his fingers, it made her want for him grow a million times over. The way he delicately moved his hands against her skin, his touch creating a fire that Stefan never could. Everything he did made her want that much more. He looked at her, his touch soft before their bodies finally connected. A gasp from her and a hiss from him was all that they needed to prove that this was something that should've happened a long time ago. He kept himself calm as they continued, taking their time to explore and to create an experience that should've taken place a long time ago. When everything was done and they both had their fill, he took her into his arms and she stayed close, a smile plastered on her face, knowing that nothing would change just how far into it she was. How close they had become. And the beauty of it all was the fact that nothing else mattered. When he was there, all that mattered was him. Only him.