Mainly for @courtneyfranta
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smut
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"Hey, Y/N." Your head turned to the direction your name had just come from, but you didn't see a single person who would have said your name so you turned back around. "Y/N?" Someone tapped you on the shoulder this time and when you turned around you saw one of the most popular kids in school, Jack Gilinsky.
"Oh, um, hi Jack." You said as you smoothed your hair. You didn't know why you always got so nervous around him. Your mom and his mom had been friends for years so you two had hung out a lot outside of school, but as you two got older you went your separate ways. Him becoming popular and you, well you fell into the crowd that nobody really paid attention to. Except for Jack right now. You were curious as to why he was talking to you.
"Hey, I was wondering if you had anything planned for tonight?" What the hell? Was Jack Gilinsky going to ask you to hang out?
"Um, no. No, not at all. Why?" You raised your eyebrow at him.
"I heard your mom mention that you've been wanting to see that movie, Tammy? Well, we just bought it and since we live right next to each other I was just thinking I could come over and watch it with you?" Oh my god. Jack wanted to watch a movie with you. Alone. At night time. This was a dream come true.
"That'd be great. What time were you thinking?" You two set up a time he would be there and the rest of the day you bounced in your seat just waiting for that time. After school you had a club meeting, but then you went straight home and straightened up. Then you took a shower and got reready for when Jack came over. By the time everything was done you had five minutes before Jack was supposed to be there. After about two minutes though you heard knocking at the back door. Of course he would cut through the back yard. After all it was connected to his. You went and slide the door open to see Jack holding a bouquet of hand-picked flowers.
"Um, my mom's garden had a lot of flowers and I know you like flowers." Jack blushed. Jack Gilinsky just blushed. In your house. You had made Jack Gilinsky blush.
"They're beautiful." You said taking them from him.
"Just like you." Jack said kissing you on the cheek as he walked past you inside. Your heart filled with butterflies and your face felt hot.
"We can watch the movie in here or in my bedroom?" You pointed down the hallway.
"Let's go with the bedroom so that way we can lay down." Y'all walked in the bedroom and you took the movie from Jack to put it in. When you turned around he was laying on your bed with his hands behind his head and his legs crossed at the ankles. You went to lay on the bed on the other side, but when you laid down jack took one arm from behind his head and wrapped it around you pulling you closer to him. You were shocked at the strength in just one arm. You settled your head on his chest and you didn't know what to do with your hands so you let them fall on your stomach, but Jack had different plans. He took the other hand from behind his head and grabbed your hand with it using his thumb to trace circles on the outside of your hand. He then turned his head to where it was resting against the top of yours. The movie was playing, but you couldn't pay attention because Jack was playing with the hem of your shirt with one hand and tracing circle on your hand with the other. When the movie was about halfway through Jack turned on his side and looked at you so you did the same.
"Y/N, you're so beautiful." You smiled and tried to look away, but Jack grabbed your chin and pulled your head back up to where you had to look him in the eyes. "I mean it. I know we don't hang out, but I want that to change. I've always been so jealous of you. You're so perfect." He took his hand from under your chin and ran it down the length of your face, the whole time he kept staring you in the eyes, but it was weird or awkward. It was like an unspoken bond. You didn't realize you two had been getting closer until you could smell the peppermint on Jack's breath and then you felt his lips against yours. It was a soft and passionate kiss, but it soon became stronger and Jack slid his tongue into his mouth as your two tongues battled from dominance. Jack quickly beat you and you were okay until he tried to take your shirt off. You locked your arms at your side so he couldn't take it off and he broke away from the kiss.
"Y/N, is everything okay?" He genuinely looked concerned and that made you feel better about the situation.
"It's just that I've never had sex before." You felt a little embarrassed telling Jack that.
"Can I be honest with you?" Jack sat down beside you and you looked into his eyes.
"Yeah, of course."
"I've never had sex either."
"You're lying to make me feel better."
"I'm not lying. I've always had this stupid fantasy that you would be the one." Jack laughed a little and you couldn't help but smile and kiss him on the cheek. Jack pulled you back to a laying position. "Can we at least snuggle and kiss a little more?"
"Actually, I think I am okay with it." You said sitting back up. Jack followed your lead.
"Y/N, I don't want you to feel pressured. Just forget I brought it up."
"Jack, I don't feel pressured. I want this. I felt a little pressured when I thought you had sex, but now I want to do it. I know you won't hurt me." Jack looked at you straight in the eyes again. He had a way of doing it that didn't make you uncomfortable.
"Are you sure you want to do this?" You bit your lip and nodded. Jack smiled as he leaned closer to you and pushed you back onto the bed and kissed you. He was a very gentle kisser. He slowly took your shirt and bra off and he ran his hands all over your torso as if he was exploring a whole new territory. You had to quickly remind yourself that this was new territory for both Jack and you. Jack placed his hands on your breasts and started massaging them as he kissed your neck. He laughed into your neck and that made you relax even more. You pulled on the end of Jack's shirt signifying that you were ready for it to come off. Jack leaned up and peeled it over his head revealing his abs.
"Has anyone told you you look pretty nice without a shirt on?" You asked and you two both broke out into laughter. This was not as stressful or as serious as the movies made it out to be. It was fun and relaxing. It was an adventure. Jack and you were trying something you two had never done before and knowing that you were the first girl Jack had ever touched like this was enough to make you wet. You squirmed a little, not meaning too and Jack got the message that you were getting a little impatient. He slid off your shorts and panties and then took of his pants and underwear too.
"This is so weird." You said once you two were completely naked.
"I know, but I kind of like it." Jack said as he kissed you and pressed himself against you. You could feel his boner through his clothes, but now that he didn't have clothes on it was much different and it turned you on a lot. You moaned into the kiss and Jack smirked.
"Are you sure you want to do this?" You quickly nodded your head yes.
"I've never been surer of anything."
"Okay. Just tell me at any time if you're uncomfortable." You nodded again as Jack lined up with your entrance. You bit your lip to keep from screaming out at the pain.
"Does it hurt?" You nodded because you didn't speak. "Y/N, I'll stop. It's not that important. You being comfortable is more important." You quickly shook your head no and grabbed on to Jack's back before he could pull out. Jack started moving in and out at a slow speed so you could become used to the feeling. Once you got used to the feeling you started moaning, "Harder."
"Mmmm, fuck, Y/N. God, you feel so good." The room was quiet except for the panting and moaning and occasional scream. After you two came you both collapsed on the bed and then started laughing. You two looked at each other and touched y'all's foreheads together.
"Jack, I'm glad my first time was with you."
"And mine with you, my love."
