⤷ ゙Day 25 : First Time ˎˊ˗

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University AU + Inexperienced/virgin!user

Lil summary

It was really easy for Dean to adapt to the new high school his father enrolled him and Sam in. Dean knew he was handsome, charming, and that he could take advantage of that, but after starting to date you, why is he being so patient with your first time?

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At this point, Dean didn't care if his father's job forced him to transfer high schools to another state. The most he worried about was his little brother not being bothered; after all, his mission had always been to protect him.

As soon as he arrived at the classroom, and as usual, all the girls were after him, some giggling, whispering, and sighing about him. It didn't bother him; in fact, he liked knowing he was probably every girl's wet dream.

Obviously, he wasn't going to gain a bad reputation that quickly, but did he reciprocate the compliments? He felt much better when a girl complimented him, but hearing your loud laughter was what he liked most. You weren't afraid to be yourself; you weren't a total nerd, but you weren't stupid either. The teachers usually liked you, but not to the point of being a teacher's pet.

During PE, the football team was practicing, but you didn't pay much attention, which kind of discouraged Dean, who was also going to play. Until you realized your best friend was going to participate, and your eyes finally settled on the practice instead of gossiping about petty rumors and irrelevant details.

Dean wanted to impress you; his agility was already innate. When the practice game ended, he approached you with a shy grin, the ball in his hands, his friends behind him cheering him on. "So, uhm, {{user}}... do you think I could come to your house or you to mine to teach me chemistry? I don't want to fail a course and... I don't know... I was thinking about you—like, so you could help me, if you want..." Dean stumbled over his words, still holding the ball.

He felt a strange rush of heartbeat when you agreed to go to his house the next day. That same day, he asked Sam for help decorating the house and gave him extra money to go out all day. He wanted to impress you with his taste in music but was afraid you wouldn't like his 70s and 80s rock songs.

The next day, when he took you to his house, you jokingly corrected him for writing a wrong fact in an exercise. He couldn't help but make a comment to make you laugh even more, even if your laughter was considered "loud"—he loved it.

When the mood shifted and only the warm atmosphere of the afternoon remained, you and Dean began to connect. He vaguely mentioned that he'd practically had to raise his brother and that, in one way or another, he'd had to skip certain stages of life. Perhaps that was why he'd been such a total player in his old high school—more responsibility equals more freedom, right?

When you started talking about how hard it was for you to open up and how you didn't trust guys much because they could be cruel, Dean wasn't offended. He actually felt bad because he knew how cruel they could be, *not to mention that he'd cheated on his girlfriend in his old high school...*

But before he could feel any more guilt, his eyes widened when he heard you say you were a virgin and that you'd like to change that, but with someone who was really worth it, someone you felt safe with. Maybe it was a hint. Maybe not, Dean didn't want to push you any further.

He shifted a little on the sofa and gently placed his hand on your thigh, waiting to see if you would reject him or not. When you didn't, he swallowed.

"{{user}}, I'm a bit of a mess with my feelings, but I didn't ask Sammy to help me clean up the mess my house was in for nothing. I'm really interested in you, and I don't want to say the typical 'I'm not like other guys' thing, but if you can really trust me, believe me, I won't let you down. Because I like you, not just physically. I mean, you are very handsome, but—but that's not all I notice. It would be much easier to say I like you just for your body instead of admitting that I like you," Dean finally said.

His hand gently squeezed your thigh, his eyes traveling down from your legs, over your torso, to your face, searching for any kind of rejection. When he didn't find it, he gave you a soft kiss on the lips.

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I was very undecided whether to do a comfort!Dean or a mean!Dean