Disclaimer: None of these characters belong to me.
Serena's first kiss was in the summer just before the fifth grade. Her mom was in Barbados with her newest boyfriend and the Waldorfs were summering in Paris, so her and Eric were packed up and delivered to the Archibalds for the week. Anne had smiled and been very polite as Lily explained her emergency, but once her cab was pulling away from the curb, Anne looked down at the two children and sighed.
Serena wrapped an arm around her brother's shoulders and the two of them followed Anne into one of the guest rooms, the one they always stayed in. It was late and Anne said Nate was already in bed, but in the morning, the Captain would take all of them sailing. She pushed some of Eric's hair behind his ear and asked him if he liked sailing. He shrugged, but Serena swore she loved it more than anything in the world.
They set out early. Nate was showing off all morning as first mate. Serena was giggling and tossing her head back, her hair catching the light of the sun. The Captain was showing Eric how to steer. And Anne sat quietly nearby, a straw hat keeping the sun out of her eyes.
When Nate finally tired himself out, he and Serena tucked themselves away in a corner where his parents couldn't see, and let their legs dangle down through the railing. Serena said that summer was her favorite time of year. Nate pushed some of her hair out of her face, and then they were kissing and Serena giggled against his lips.
She'd watched her mom kiss so many guys and always wondered what all the fuss could be about. Before the summer was over, she kissed at least three other boys and ended up giggling against them each time, swearing it was the best kiss ever.
Nate always thought it was perfect, how his first kiss with Serena had been at the height of summer, with the sea breeze blowing in her hair, and his first kiss with Blair had been in the dead of winter, her cheeks burning red against the snow. It was the last Monday before Christmas break and he knew that she'd been trying to get him to kiss her for a while.
Blair wanted it to look spontaneous, but even Nate could see through her. She wanted their first kiss to be in the rain, like in all her favorite movies, so every time it rained even a little, she would flutter her eyelashes, pucker her lips, and hold his hand so tightly it hurt, and Nate would almost do it, but then he'd hear Serena giggling and stop.
Once the rain had been traded for snow, he relaxed around her, figuring she would stop trying for a while. So, when she suggested they go for a walk in the Park after school, he hadn't thought anything of it. Her maid, Dorota, walked behind them, as they looped down the paths, careful not to slip on patches of ice, laughing when the snow started flurrying.
Blair watched him, biting her lip, as he shook the snow out of his hair, and then he reached forward and did the same for her. And with his hands still in her hair, she leaned forward on the tips of her toes and pressed her lips against his. She did it quickly and Nate was so surprised that he still hadn't let go of her hair. She gave her maid a look and the woman turned and faced the other way.
Blair looked back up at him, her cheeks red, and smiled a small, tiny smile like she was suddenly uncertain, so Nate leaned down and kissed her once more. She smiled against his lips and he thought about Serena's giggle. At least, he knew Blair's smile was just for him.
Blair hadn't meant for it to happen. She had spent months trying to get Nate to kiss her like he'd kissed Serena. Months. She came home from Paris to Serena's tan and stories about kissing boys, Serena swearing it was her favorite thing ever.
Once Blair knew that Serena had kissed Nate, she'd wanted to know everything: how it felt, how it happened, what he tasted like, if they were going to do it again. Serena shrugged her shoulders at the last question, giggling, and thinking about all the boys she had yet to kiss. Blair leaned back in her pillows and thought about the only boy she wanted to kiss.
So, she made plans and tried and tried and tried. She would watch the weather channel constantly, keeping track of the rainy days. She wanted it to be like Breakfast at Tiffany's, only without the cat or the dirty alleyway, but no matter how hard she tried, he just wouldn't kiss her.
And then it was Christmas time, and she was just tired and confused and nervous, and she just wanted to spend a day with Daddy at the Met and not think about Nate once. Somehow, and she wasn't sure how, she ended up kissing a boy in the coat check room. A boy she had never seen before, a boy who was definitely not Nate. And she liked it, liked it so much that she kissed Nate the very next day, smiled against his lips and thought, "this is my real first kiss."
Dan never had anyone to talk to about his first kiss, but he wrote about it almost immediately. He didn't know the girl that he caught staring at him in the Easter Island exhibit. He didn't get her name when she made fun of his torn jeans, or commented on how he was tracking slush in with his shoes, or asked her father if there weren't rules about what kind of people were allowed in the museum.
He didn't want to know her name when he called her a spoiled brat and marched away. And he didn't have a chance to ask it, when she suddenly pushed him into a wall and pressed her lips against his, her hands digging into the fabric of his green flannel shirt, and his hands at his sides, unsure if he was allowed to touch her. The coats pressed up against them on either side, enclosing them there, like a secret, and she made a soft little sound at the back of her throat and he felt her breath on his lips.
He was so surprised that he didn't even shut his eyes, but she did, and her whole face had relaxed. When she finally pulled back, she didn't let him go right away. Instead, she brushed her nose against his and slowly opened her eyes, as if waking up from a dream. And then just as quickly, the moment was gone, and she was grabbing her own coat, scarf, and beret and running into the lobby.
He stared after her for a moment, stunned, before tripping and stumbling his way out. His mother grabbed him just beyond the door to force him into his coat. He could see her the whole time, struggling with her own coat, with her own parent. The both of them just staring at each other and then she sort of licked her lips without thinking. Her brown eyes widened in horror and suddenly she was running out into the snow, with her father trailing after her, still holding her little red beret.
Dan strained against his mother, wanting to catch her, to speak to her, to anything, but by the time he got outside, she was long gone and all he could do was press his fingers to his lips and think about the story he would write when he got home.