A few months ago when I was re-watching season 1 for my "The Many Times Kurt Hummel Lied About His Sexuality" fic (which this, if you'd like, could be considered a companion to it though that's not a requirement) and I decided to did a little deeper on the time Kurt and Brittany were together since of course we only saw the super scandalous moments in the show. I also love looking into Kurt's head and any excuse to look deeper into the canon just gets the creativity flowing.

This was originally a one-shot but when it grew to about 30+ pages I decided to break it down into parts, so here's part 1, which is also day 1. Please feel free to tell me what you think!

(Also posted on Archive of Our Own under the same name.)

Tap that. A girl had really just offered to let him tap that. Granted it was Brittany but in the grand scheme of things, she was what the school considered to be a hot girl and many boys wanted to be with her. Some had gone insanely out of their way to impress the girl - especially considering that they really just didn't have to - just so they could have the opportunity to tap that. And she had come up to Kurt and offered. The other New Directions gave him wide berth as they left the room, but he reached out to tap on Britt's shoulder. "I would."

"Would what?" She glanced up from her phone. He took a deep breath. Coach Sylvester was right - he'd never kissed anyone. Sure he knew that manly chests and manly abs and the thoughts of a man's lips up against his own while the tips of their fingers trailed over each other's...well, those were the sorts of fantasies he knew turned him on. But Coach Sylvester was right. He had never even tried being with a girl. Or a real boy that might actually potentially maybe be able to return his affections, but the point of the matter was that he'd never even given a second thought to trying to date a girl. He let the breath out.

"Brittany Pierce, would you like to come over to my house after school?"

"Yeah, totally. I love hanging out with you. Are we going to dance or make out? I need to know so I can figure out what to wear."

"Make out." The smile on her face was contagious. Or maybe he just felt giddy that he was actually going to do a very normal teenage thing. Either way, Kurt Hummel was well on his way to having his first kiss. Four years after most of his class, it seemed, but it was going to happen tonight.

"Would you like something to eat?" Kurt offered as Brittany entered the house. "Dad won't be home for hours so we have time." Brittany had been here plenty of times before. The girls always hung out with him. So he knew how to have girls over and all the girls knew the general rules of his house. But this wasn't a normal visit. Kurt wrung his hands together nervously.

"Not really. I mean I would but...Coach Sylvester is already upset that I gained weight last week."

"Yeah. I know. But I thought I'd offer anyway. I mean, I don't want you to uh, to be hungry when we. I mean." He felt his cheeks heating up. Brittany knew the way to his room and she used that knowledge to head straight for the door. "Oh we're going to go downstairs ok."

"Well I mean unless there's somewhere else you wanted to be. Some guys really like the kitchen."

"Because...there's food?" From what Kurt had seen, most of the boys Britt spent most of her time with seemed to think with their stomachs first. There was something he hadn't tried yes. Cooking for - no. He wasn't going to think about Finn now. He was going to try to be with a girl without thinking about a boy. Especially not a straight boy.

"Because they think its hot to have sex on the counter. It's weird." Kurt tried not to gape too much as her words grounded him back in the reality of their situation here. "Sometimes I think about what it might be like to be a sandwich, or a plate of cookies. You know, people put their hands all over them too."

"We are not going to have sex Brittany." That was definitely out. "At least, not tonight." Or, most likely any other night. Though he was trying to keep an open mind about this which meant it was potentially an eventual possibility if things went well. Maybe. Not likely, but maybe.

"Oh...why?"

"Because I am not ready for that." He slipped over and offered her his arm. She hesitated before taking it.

"You're not like the other boys."

"You can say that again."

"You're not like the other boys." He couldn't help but honestly laugh as he led her downstairs.

"Ok, real fast, I need to make a note. In case Dad comes home, so he doesn't bother us, ok?"

"Ok." She made herself comfortable while he darted back upstairs. The words were simple. Pointed. They came from the heart. He was going to try this. He was going to try very hard to be the son his dad wanted. By having sexual relations with a person of the other sex. He could be normal. He could be just like the other boys. He was going to show his dad just how hard he was working.

When he came back he found Brittany stretched out on her stomach. Legs tucked up, skirt a bit high on her legs, chin in her hands. Batting her eyes at him.

On his bed.

"Brittany how about we, er, well, do this somewhere that isn't my bed? It's really not the most comfortable mattress and I don't know how the whole two bodies thing works but it barely works for one body so maybe...how about my couch?" Of course those were all lies but there was a girl on his gay boy bed with intentions of doing something other than just look at fashion magazines. No, no. He was going to be open minded. But that didn't mean she had to be on his bed.

"Most people don't have living rooms in their bedrooms."

"Yeah, I know. But there's so much space down here. I didn't like it all being open and empty all the time so I had to fill it with something." He offered his hand to her to help her up. If there was one thing he did know about relationships with girls, it was that he was supposed to be a gentleman. Not all boys were like that, as he'd well learned from observation alone, but his mother had made sure he knew he needed to behave himself and respect his partner.

Her fingers were soft as they curled around his hand.

"You have no idea what you're doing do you?" she asked.

"Well I know how people kiss, if that means anything." The blonde sat up and held her head high. She almost never had an opportunity to teach people. Even when she could, everyone assumed she couldn't. No one was going to tell her she was incompetent here tonight. Right now, she was the smartest person in the room considering what they needed to be smart over. Brittany confidently pulled herself from his bed and moved to the couch. Her hand patted softly on a cushion. Kurt complied. His heart felt like it might beat right out of his chest.

Funnily enough he didn't feel the slightest bit stupid for learning from her.

"Here, give me your legs."

"What?" His ankles started to cross on instinct.

"Trust me. You wanted to be comfortable right?"

"Yes but I don't see how-"

"Trust me." Kurt tried not to hold his breath as her arm tucked under his knees and pulled them up across her lap. Her other hand pushed down on his shoulder. He took the cue to lay back. "Now get comfy." Kurt shifted around until his neck didn't feel like it was going to snap from the pressure of the armrest, then he stretched his legs out to drape over the other one. He consciously crossed his ankles just to be safe. He was certain Brittany wasn't going to turn him on but he wasn't so sure he wouldn't start dreaming about Taylor Lautner kissing him instead. And that would be a turn on.

"This is nice."

"See? I know what I'm doing." Kurt gulped. This was it. He was about to make out with someone. Brittany didn't even hesitate really. She leaned over and pressed her lips against his.

It felt wrong.

But he let her do it again.

Didn't making out include tongues?

She wasn't forceful with him. The suction of her lips tugged on his and pulled them ever so slightly apart but she didn't just start shoving their tongues together. Or however this was supposed to work. Kurt was pretty sure making out usually included tongues though. At least that was what he'd heard from other people. He wasn't so sure he wanted that.

He was sure he wanted to make his dad happy. So he tilted his chin up to try to kiss her back.

If she initiated tongues he would try his hardest. Though now that he was thinking about tongues he couldn't stop thinking about a hot boy sitting in Brittany's place. The anatomy of the mouth was the same, of course, but to him a boy's mouth was quite different from a girl's mouth. It was attached to a body that he was actually interested in.

"What do boy's lips taste like?"

It wasn't long after that when his father intruded. Apparently 'hours' actually meant thirty minutes.

"Did he mean like a burglar alarm?" Kurt was starting to regret his decision. Brittany was a nice girl. She really was. Despite that, she was classifiably dumber than a bag of rocks, if her grades were any indication. She was every dumb blonde joke he'd ever heard personified.

"No, he meant sexual protection. You know, to prevent babies."

"Wait. There's a way to do that?" Kurt felt his muscles tensing up. He crossed back over to her and settled down next to the girl.

"There's several ways, actually."

"If this is about the 'after' stuff, I'm not interested."

"...No, no, there's before stuff too. Er, well, during, I guess. Girls have a lot more options than guys. Do you really not know any of this?" Her blank look sank his heart. Kurt knew he was rather uneducated himself but at the very least he knew what protection was. "The pill...condoms?" He watched a lightbulb go off in her head. Really. If he squinted he could see it glittering in her eyes.

"Aren't those a kind of water balloon?"

"No. No those are...No. Why do you even think that?"

"Well, one of the boys I was with had some and he filled them up with water and we had a water balloon fight. He said that was what they were for."

"Didn't you pay attention in health class?"

"My parents didn't let me go. They said it would make me proper or something like that. Which I don't understand why that's a bad thing."

"Proper?"

"Yeah, it's what they said. That it would make me proper which proper means that I'd have good manners, so I don't understand." Kurt's mind ran through all the P words he could think of. As he tried to narrow it down to P words related to sex, one in particular flashed into his mind in big red lights.

"Promiscuous."

"That too." Kurt took a deep breath and then he took hold of her hand.

"It doesn't mean proper."

"What does it mean?" Her eyes were so bright. She was curious. She clearly wanted to learn. Kurt just wasn't sure she was capable it. Brittany was like an innocent child. And, just like a child, her comprehension abilities were extremely basic.

"It means...someone who kisses every boy in the school. And has sex with as many people as they can." He didn't want to imply that she was wrong but that was basically what the word meant as far as he understood it.

"Wait. They said I would only be promiscuous if I went to Health class."

"Health class has nothing to do with promiscuity. Actually, I'm pretty sure it cuts back on it. I know I don't want to have sex with someone I'm not familiar with after seeing all those pictures of STDs."

"What's an STD?" Kurt felt his cheeks heating up. It was quickly becoming his full time job, apparently, to teach Brittany the wonderful dark underbelly of unprotected sex. Just great. He scooted a little closer so he could keep his voice down. In case his dad came back.

"Its a sexually transmitted disease, and there's lots of them. Some are curable, some aren't. Like HIV and, uhm...warts I think? There's a lot. And some are deadly." Brittany stared at him with a completely blank look. "Britt?"

"You mean that wart I got on my toe was from sex?"

"No! Most likely not. But if you get warts, uhm, in your happy place, that is." When she didn't question what a happy place was the teen was sure he was starting to get to a more comfortable part in the conversation.

"How can you tell if you have an STD?" He was clearly mistaken. At first Kurt tried to form words. The teacher had talked all about the symptoms of all the diseases with such a straight face. They'd even made some 'clap' jokes. For boys. Girls didn't have to worry about that whole tidbit of history. Just thinking about saying those things out loud stopped all words up in his throat. So he shifted gears.

"Tell you what, how about we go by the free clinic tomorrow after school and pick up some booklets for you?"

"Like a date? Are you going to buy dinner?"

"I can do that."

"Should I bring Santana?"

"Why would you bring Santana on our date?"

"Well sometimes the boys want to watch us make out." Right. That was considered a turn on for boys who liked girls. It didn't make a whole lot of sense to him but then he was pretty sure the only thing that caused any sort of reaction for him was men kissing men. Even as he tried his hardest that fact was still abundantly clear to him.

"I don't want you to do that. I want to go out, just the two of us, ok? Where do you want me to take you?"

"Breadstix?"

"Of course. Whatever you want Britt." She leaned over and gave him a kiss.

"You're really sweet."

"Thank you." She gave him another kiss. It definitely wasn't doing anything for him. Probably never would. But that was ok. He wasn't doing this for himself.

"Kurt?"

"Hm?"

"I know this was supposed to be just a one night thing but since you're taking me on a date tomorrow, does that mean you're my boyfriend?" Kurt looked into her shining eyes and weighed his options. She was nice. And having a girlfriend would go a long way to showing how hard he was trying, not to mention how much easier school could be, and if she ever wanted anything more than kissing he was pretty sure he'd be able to talk her out of it. They'd definitely have fun together. Her fashion sense was eccentric sometimes but she had a good eye for those odd pieces that looked crazy on their own but actually turned out to be quite amazing when put together in an ensemble. A relationship with her could be easily limited to shopping, dancing, and just...having fun. Boyfriends and girlfriends didn't always have to do more than that.

"Yeah, I guess it does." Her hand curled around his head and pulled him in for another kiss.

He was never going to get used to that.