Lucky
When Jess gets an A on her European history final, which had taken up pretty much every one of her waking moments for the past two weeks, Sam sets her down after spinning her around once in the caf and goes, "I'm taking you out. Somewhere nice. Where do you wanna go?"
"Well…"
"Jess. Anywhere you want."
"Okay. Well there's a place on Seminary that I've kind of wanted to try. I don't want it to be crazy expensive though, okay?"
"Hey." Sam looks her in the eye. "Don't worry about it. Anywhere you want."
In the days leading up to the dinner, Sam senses that this date will have a heavy sense of formality over it, something more serious and a little more intense than bowling or watching Stanford soccer on Saturdays or doing homework in the library. He's probably gonna end up wearing a tie. They've been dating about a month and they've talked some about their dating pasts—Jess had a boyfriend in high school named Robbie, with whom she parted ways after senior prom—but Sam has never come out and said, "I'm a virgin" to her. Jess isn't. She made that clear from what she'd said about Robbie.
But Sam feels like it's time. He likes when she sneak-attacks him on the quad, on his way to class, and almost tackles him to the ground with a hug from behind. He likes how she didn't push him to give more than a few sentences about his family. He likes how he can lie on his dorm couch with his head in her lap, and not say much of anything while she runs her fingers through his hair. He just really, really likes her.
Sam thinks several times about calling Dean. He hasn't heard from him in months and he isn't quite sure how he'd approach the subject, but he really just needs to hear his brother go, "You'll be fine, Sammy. Are you kiddin' me? So who's the girl?" But he keeps deciding against it. For one thing, there's a chance Dad could overhear and that's the exact last thing Sam wants to have happen. So he tries to do the rest of the conversation in his head to himself, but when he gets to the part where Dean would offer advice, Sam draws a blank.
Dinner is only slightly cheaper than a year's supply of salt rounds, but Sam has been saving up from his job in the computer lab and besides, Jess is more than worth it. Her blonde curls are up in a high ponytail and she's wearing a black dress that Sam's never seen before, but that he thoroughly appreciates in the way it hugs her curves. When she gets up to go to the bathroom, he tries to scope out where the zipper might be, and instantly panics when he can't find it.
"Ready?" she asks, after the waiter finishes running Sam's card and brings it back.
"Uh. Yeah," he says, swallowing hard.
They go back to Jess' room, where her roommate has gone home for the weekend. Sam wonders if Jess worked it out like that on purpose. Either way, thank God.
Jess hops up on the bed, which is lofted three and a half feet above the ground, and kicks her heels off one by one. She pats the comforter next to her.
Sam can feel his heart trying to beat its way out of his throat. He is probably going to throw up 40 dollars' worth of chicken onto her bed, and then she will hate him forever.
He can do this, though. He can. It's fine.
They get as far as Sam's tie on the floor and his shirt unbuttoned, and Jess generously starts the zipper on her dress for him (turns out it's on the side), but when he opens his eyes to her electric pink bra making its appearance, his brain finally catches up with his hands and he pulls away from her so fast that their lips make a smacking sound.
"Jess?"
"What is it?" There's panic in her eyes.
"So this is my first—I mean, I've never…" He waits for her to say something, which he can usually count on her to do. But for maybe the first time in her life, Jess is silent. She looks at him with wide eyes and waits. "I've never done this before," he says in a rush.
Then Jess leans in and puts a hand on the back of his neck, gently pulling him in for a kiss that is long and sweet.
"I kind of figured," she says softly, after they break apart.
"You did?" Sam feels heat rush up into his face.
"It's just that you said you hadn't dated anyone before, and you're not really the type to love 'em and leave 'em, ya know?"
Sam tries to consider what he looks like sitting on the bed now, the stupid virgin next to this stunningly beautiful girl. "Yeah, I guess."
"No, it's not a bad thing. It's not," she says. "Are you okay? You're sure you wanna do this?"
"I mean, yeah. Absolutely."
Jess smiles encouragingly. "Then it's gonna be fine. We'll just take it slow, okay?"
Sam feels such a rush of relief that he thinks he might pass out. "Yeah, okay. That sounds good."
Then, though Sam uses half of his brain to repeat go slow, go slow, go slow to himself while the other half is doing things like focusing on unzipping his dress pants and unrolling the condom and making sure he doesn't hit Jess' head on the headboard when he goes to get on top of her, even after all that, everything is over in about three minutes.
"So," Jess says, supporting herself on one elbow and looking down at Sam, who's lying on his back. "How was that? Any kind of feedback you wanna give me so I can make your experience more enjoyable for next time?"
Sam stares up at the stark white dorm ceiling. "No, you were great—I just… sorry it was so short."
Jess shrugs. "Fine by me. It was like the short story version of sex, yanno? It had the beginning, the middle, the end. All the parts you need."
Sam turns to look at her. "Yeah, but you didn't—did you?"
Jess gives him a wide smile. "Sam. Don't worry about me."
"But I want to worry about you," he says.
Jess kisses him again. "It was perfect. Thank you. We can try again later, if you want."
They lie back together, side by side, and talk for a while until Sam goes, "So, I mean… do you want to? Again?" And Jess does, so they do. And a third time, a few hours after that. Sam isn't sure what he was worried about to begin with. But he realizes that he got really, really lucky to land Jess.