#assbuttmorelikecasbutt

“Well given what he just experienced, I didn’t think there would be a better opportunity!” he defended himself, popping open another beer.

You sighed, rubbing your temples. He was right. Jack may only technically be a year old, but he had the body of a 21-year-old, and he was half (more than half, with little to no grace) human. It wouldn’t be healthy for him to be unaware of at least the basic mechanics of what humans do to reproduce, but you had a suspicion that Dean’s version of “the talk” wasn’t the basic mechanics of safe sex.

“Well, what exactly did you tell him?”

He rolled his eyes dramatically. “Oh, c’mon. I just had this conversation once, I am not about to rehash it with my little sister.”

“I don’t need you to tell me how to woo a woman in bed, Dean! I need to know that you taught him about the importance of consent and how to wrap it up!” you exclaimed.

“Of course I-” But you cut him off before he could finish. You decided it would just be best to talk to Jack yourself. At least then you would know that Dean didn’t talk to him about anything that he couldn’t just find on Pornhub.

As you approached his bedroom, you could hear the coughing. It was getting worse. You felt your heart drop. It killed you that you had yet to find a single piece of information that could help him within all of the hundreds of lore books in the bunker’s expansive library. 

You knocked softly on the door. “Jack? Can I come in?” You heard some shuffling and the door opened a second later.

“Y/N, of course.” He smiled at you sweetly, moving to the side and allowing you to come in. You sat awkwardly on the edge of his bed, picking at your cuticles. You couldn’t help but notice that his trash can was filled with bloody tissues.

“How’re you feeling?” you decided to start with.

“I’m feeling better. Well, not better, really. But I am no longer bleeding from my nose and fainting,” he said as happily as ever. You always admired his positivity.

You nodded and smiled, trying not to let it show how worried you truly were. 

“Rowena will be here tomorrow. She is going to help us figure this out. We aren’t going to give up. I promise,” you assured him, taking his hand into yours for a moment, releasing it when you remembered why you had come to his room in the first place. 

“So..” you hesitated. “Dean mentioned to me that you and him had a talk?” you prompted, hoping that would be enough for Jack to spill the beans on what Dean had said.

“Yes, he told me how sexual intercourse works!” he nodded excitedly. Before you could reply, he continued.

“Dean said that when I am attracted to someone, I will feel the strong desire to be with them, in a way that I don’t feel with everyone else. He said that I will specifically feel it in my penis.” Your mouth hung open for a second, taken aback by his bluntness.

“Oh yeah? What else did he say?” Now you were curious.

“He said that, usually, I will know if the person reciprocates these feelings because they will communicate them to me in some way, but if I am ever unsure, then I should ask before “making a move” on them, because I wouldn’t want to make them uncomfortable.” You were unable to hide your surprise. You shouldn’t have doubted your brother.

You decided that you felt comfortable enough to leave the topic alone. 

“I am glad to hear that that conversation went well, Jack. I just wanted to check on you, so I will let you rest now-” You got up to make your way to the door when Jack grabbed your hand, pulling you back down to his level.

“Can I ask you a question?” 

Oh boy. You braced yourself.

“Of course, Jack.”

“Have you ever had sex?” Well, there was no turning back now. 

“Yes, Jack. I have had sex,” you answered honestly.

“Did you enjoy it?” he asked innocently. 

“Well,” you started, looking around the room awkwardly. “I have had sex a few times. Some times have been more enjoyable than others. For me, it just mainly depends on how comfortable I am with the person I’m doing it with.” You brought your eyes back to him to find that he was staring at you intently. 

He nodded, processing what you had said.   

“Dean told me that my first time should be special. That it should be with someone who means a lot to me.” Dean Winchester, a romantic.

“That was very smart of Dean to say. I would agree that the more special the person, the better it is.”

“You’re the most special person I know. I would like very much for my first time to be with you,” Jack said nervously. You could feel your eyes grow ten times wider than they should be and you racked your brain, trying to think of what to say. Luckily, Jack continued before you had to.

“When Dean and I were on the hunt, Harper asked me if I believe in love at first sight. I didn’t answer her, but I knew that in my heart, I do. I believe in love at first sight because you were the first person I saw after I was born.”

You could feel yourself blushing what you knew to be a vibrant shade of pink. You’d had feelings for Jack since he came into this world, and now he was confessing his love to you and asking you to take his virginity. You tried not to pass out on the spot.

You were silent for a moment too long and Jack began to backtrack. “If you don’t want to, it’s okay, I know it’s probably asking a lot-”

Before he could say anything else, before you could overthink it, you cupped your hands around Jack’s face and pulled him into you, pressing your lips into his and moving your fingers into his golden hair.

Jack hesitated a moment, taken by surprise, but soon began to move his lips with yours. He tasted sweeter than you imagined and you were impressed by how naturally it came to him. His hands went to either side of your waist and you pushed him back onto his pillows, climbing on top and straddling him. You moved your tongue across his bottom lip, asking for entrance, which he quickly granted.

You could feel him growing hard through his sweatpants and the sensation of it made you move your core against his. An involuntary moan came from the back of his throat and his hands moved to cup your ass. After another moment, you were both out of breath and you pulled back to stare into his lust-blown eyes.

“I would love to be your first time, Jack.”