Disclaimer: I own nothing

Thanks for pointing out the bit about Damon not actually wanting to kill Caroline's dad. I did realise that as I wrote it and figured that she probably thought he was going to, seeing as that's what he told Elena.

The first time she kisses him, she is entranced by his charm and his looks. His eyes mesmerise her and his smile bewitches her.

Later, she wonders why he even bothers with compulsion.

Not long after that, she begins to associate his kisses with pain. The feeling of his lips against hers mixes with the sensation of his teeth tearing her out throat.

Later, she traces the bruises and scars that mar her pale skin and wonders why she can't run away from this demon.

She forgets his kisses soon after that. She remembers nothing. She thinks that it was a bad breakup and a relationship to be forgotten.

Later, she wonders how she was so gullible.

He doesn't kiss her again for nearly five years. They're drunk and can't deal with Elena and Stefan's latest drama and temporary break up. It's happening more and more these days, usually about her turning. Neither wants it to happen but both know it needs to if they want their happily ever after.

Both Damon and Caroline have had enough bourbon and scotch to knock out a human, and are beginning to feel the effects. Somehow amidst their hysterical laughter and out of tune singing, their hands end up tangled in each others' hair as they force their lips together. It takes Caroline several minutes before she slaps him.

Later, she curses herself for not hitting him sooner. Or harder.

The next time they kiss, forty years have passed and they haven't seen one another for nearly thirty of them.

Elena's dead.

They both knew that it would happen, ever since she decided to stay human, but no one could have expected it to happen so soon. How disease could have killed the woman who had fought off the oldest and most dangerous vampire in all of history, was beyond them. They stand in the distance, watching the ceremony making sure that they aren't seen. They are too young.

Always too young.

Stefan's absent but that comes as no surprise. He took up the title of "Ripper" not long after she made her decision and they left one another. The last Damon heard, he was off with Klaus somewhere. As much as Damon wants to help his younger brother, Stefan didn't want to be saved and they know that.
Damon holds Caroline tightly as they watch the ceremony. She cries silently and Damon presses his lips against the top of her head. It's not a real kiss but Caroline counts it on her list.

Later, she wonders why she even keeps count anymore. Why it even matters.

After that, they see each other every few years, making sure that they keep in contact. He still drinks human blood. The whole fuck, feed, forget method is effective and she finds that she is starting to use it too. Blood bags were never going to be enough. She sees Stefan once in the next century. He's still on human blood but no longer with Klaus. She views it as a slight improvement. He refuses any offer of help, claiming that he was in control of it and asked her to give his love to Damon. She laughs at that.

The idea of the brothers being affectionate towards one another seems ridiculous.

But Damon looks relieved when she tells him that his brother seems alright and receives the offer of 'love' with a grunt and a look of tenderness in his eyes that she doesn't think she's ever seen.

They don't kiss again until two centuries have passed since they met. She still remembers a time when she hated him. When he compelled her and abused her. When he almost killed her. When he tried to kill her father. But it doesn't matter.

No one can hold a grudge, no matter how great, for eternity.

Somehow she always knew they would end up together. His love for Elena, while passionate, was fleeting. Anyway, she made her choice which ended any chance of a relationship with either brother. His one night stands were only an excuse for fresh blood and the occasional fling he had with another vampire usually ended badly.

Damon seems to inspire a universal impulse to try to drive a stake through his heart.

She doesn't remember when he kisses her or why. She remembers thinking that it's their forty seventh kiss and wonders why a number even matters anymore. She knows it won't be their last. Because eternity is a hell of a long time.

She stops counting kisses after that.