So, You're a Fucking Virgin

Chapter 7

You woke to a world in which Dean Winchester wanted to sleep with you. Or, at least, was willing to sleep with you. He didn't exactly say he wanted to sleep with you, did he? Willing and wanting were definitely two different things. This much you had decided during your largely sleepless night.

Other major topics of consternation included:

-Would he want to have sex immediately?

-What kind of sex would occur?

-Would there be cuddling afterwards or would it just be wham, bam, thank you ma'am, the whole thing over in five minutes?

-What expectations does he have in terms of grooming?

-Would it be weird afterwards? (dumb question seeing as how it was already weird)

-Does this mean he likes you?

-How would you feel about that if he did?

We were definitely through the looking glass here, people.

"Got a second?" you said, popping your head into the kitchen, where Dean sat eating his breakfast.

"For....?" he questioned, a mouth full of food.

"I was wondering if we could talk?"

"About...?"

"Your P; my Va-G."

Dean choked on his food. You rushed over to him.

"Whoa. Arms up. Arms up." you hit him on the back as he took a drink of water.

"Ps and Va-Gs?" he said looking up at you with raised eyebrows.

"Mmmmyep." you said sitting down. "About last night."

"About last night." he repeated after you.

"Were you serious? Do you want to do this for me...I mean..with me...because you don't have to. I'm not going to hold you to something you said if it was just to make me feel better, you know. Don't do this just because of your hero complex."

"Hey" Dean grabbed your hand from across the table "I want this, ok?" he said cracking a smile.

"Okay" you said gulping. "Okay" you said nodding more confidently. "Well in the interest of that I thought it might be beneficial to discuss, what we both want from the...um...encounter."

You produced a thick sheaf of paper from seemingly nowhere and thunked it down on the table.

"What's that?" Dean eyed the pile of paper with suspicion.

"I made a list"

"You made an encyclopedia"

"I just wanted to remember everything"

"Ok. So, the list:

Condoms. Duh, safe sex.

No pain if possible- contrary to popular belief it does not have to hurt your first time. That happens because the woman is not properly aroused

Cuddling afterwards

No calling you "daddy". I'm sorry, at least for me that shit's messed up.

"Agreed" said Dean.

"5" you continued "I'm okay with the lights being on, but reserve the right to turn them off if I choose."

"Out of curiosity, how many more items do you have on this list?"

You flipped through all the pages, counting.

"Ummm...several"

"Really taking the casual out of casual sex here, ______"

"I just want to make sure we both have a fun time" you said, almost pleading.

"Yeah, this is really fun"

"What about you? You like pie. I could dress up as, like, a sexy pie. She's my cherry pie" you started singing incredibly off key.

"I like pie. I dont want to fuck a pie." Dean responded.

"Okay. Okay, then. Well, what if I dress up like one of your anime girls? 'Oh senpai has noticed me.' and whatnot?"

"Why not tentacle porn?" Dean said joking.

Your face turned beet red.

"Item 327" you said, flopping, your pile of papers towards him.

Dean flipped through them and sure enough, Item 327: "No tentacle porn inspired sex". Wow, you really had been thinking about this.

Sam was sitting in the library doing research as per usual, when Dean unceremoniously slammed what could be referred to as _____'s manifesto down on the table in front of him.

"What's this?" Sam said, beginning to flip through the pages. "172: No Anal?" Sam asked.

"Oh this? This is ____'s sex contract." Dean paced the room.

"It took her til 127 to get to 'No Anal'?" Sam read out loud.

"This is her idea of casual sex." he began to recite the list to Sam "#37: permission to keep my bra on if my boobs aren't in their best aesthetic shape on the day...parentheses trust me sometimes they look much better in the bra than out. close parentheses #89: if music is present it shall either be Bolero or Fleetwood Mac. Absolutely no Marvin Gaye unless it is sung live" What does that even mean? Do I have to get Marvin gaye? I thought taking someones virginity was supposed to be sexy fun. This is not fun. "

"Dean, she's not exactly young. Sure she's probably built it up in her mind but she's also realistic and she's had a lot of time to think about this and all the things that can go wrong. Have you maybe thought she's a little bit scared and this is how she's trying to protect herself? And look at what she's asking you. It's actually not that unreasonable." Sam explained.

"But it's so formal" Dean almost whined.

"She's never had sex before maybe the only way she knows how to communicate what she wants is with a dissertation. She's gone 26 years with nothing. To go from nothing to everything so fast can be a little daunting, I'm sure."

"She doesn't trust me to take care of her."

"She doesn't know what she's doing. You need to help her. Listen, if you don't want to have sex with her don't have sex with her. Just please never show me your kink lists again."

Sam was right, if this is what you needed to feel comfortable having sex with him, Dean had to respect that. But did Dean really want to have sex with you? The answer to that was easy. Yes, absolutely. If it were under normal circumstances he would definitely want to have sex with you. Hell, he wanted to have sex with you from the time you first referenced Star Trek during a hunt. But that was before he knew. Were there too many strings now? If he still wanted to have sex with you after the pile of crazy that was this list and he actually had it what would that mean?

Much to his chagrin, to get to the bottom of this Dean would have to do what he hated the most: Talk to you about it.