I'm yours to keep

And I'm yours to lose

You know I'm not a bad girl, but I Do bad things with you

So it goes

Stiles woke the next morning, Jackson wasn't in the bed beside him but he didn't expect him to be. He picked up his phone to see a text already there from the beta werewolf.

Had to get home before parents woke up. Pick me up at the school at 7 pm, Stilinski. Wear something sexy.

Stiles chuckled and texted back.

Everything I wear is sexy, Jackson.

That was a lie, Stiles knew his fashion sense was limited with how he dressed. It was just jeans, graphic t-shirt, and some high tops. He knew he should do something different for tonight; he moved out of his bed and made his way to the closet, opening the doors and looking inside for something that would look good for a date with Jackson. Date. That word hung in his brain like a dream, he had expected their tryst to end last night when Stiles told him how he felt but lucky for him; it seemed to get better. He pulled out a button down red shirt. It looked ok and maybe Jackson would be shocked to see him in something besides a graphic tee. Next he pulled out jeans, tossing them on the bed beside the shirt. He didn't bother looking for other shoes, he would wear his usual ones. Stiles knew Jackson would be dressed in designer duds, but this would have to do for him. He went to his phone, scrolling through his photo album to find a selfie he and Jackson had taken together. Jackson was scared to take it and made Stiles promise to not show anyone once Stiles agreed they took the selfie together. It wasn't anything special if anyone saw it. They wouldn't assume they were boyfriends, they would just be more confused why they were together. The only time people ever saw them talking was at pack meetings, they barely talked at school. They all sat together at a table, but they never talked. He put the phone back on the bedside table as he heard his door open from behind him.

"Going somewhere tonight?" asked John as he walked into his son's room, Stiles turned and nodded.

"Yeah, going to D's Diner. Craving one of their burgers." Said Stiles lying to his dad, which was nothing new.

"You going alone or are you dressing up for someone?"

"Dressing to impress dad, thinking I would get a free pie out of the deal if I looked nice.' Said Stiles sarcastically, causing his dad to chuckle.

"Just be home before curfew, because you know I know how to find you." Said John pointing to the badge on his chest before giving his son a wink and closing the door. Stiles had no issue in believing his dad would send out an APB if Stiles was ten minutes late for curfew. He rolled his eyes at his dad though he couldn't see it through the closed the door as he made his way to the bathroom.

Stiles' fingers were tapping a quick beat on his steering wheel as he waited for Jackson in the school parking lot. He wasn't sure how they would do this, but once he saw Danny's car pull in and Jackson get out. He figured that Jackson had told him some kind of lie on why he was going with Stiles, he knew Danny didn't know the truth. Jackson opened the passenger side door and just stared at Stiles for a moment. He was pleasantly surprised to see Stiles wearing something different. He smirked before closing the door with him on the inside.

"Almost didn't recognize you, Stilinski." Said Jackson with a smirk.

"Shut up, Jackson." Said Stiles with a smirk as he put the Jeep into gear, making his way out of the parking lot.

"I told Danny to not ask questions, just that we would do pack things. He won't mention it to anyone. I thought it would raise questions if I left my Porche here all night." Said Jackson, he knew the question was on Stiles' mind.

"Danny boy is a good friend, the only one who would understand this."

"Probably, but not going tell him." Said Jackson, Stiles knew not to press the conversation. He reached his right hand towards Jackson, who smirked at it before lacing his long fingers with Stiles'. There was something strange to both in this moment. Then it hit them both at the same time.

"We have never held hands." They said in unison, causing them both to chuckle.

"First time for everything, Stilinski. Just think of it as another treat." Said Jackson with a wink as he looked out the window to watch the trees travel by. The silence was comfortable for them both, there wasn't a need for conversation or music, just the sounds of the world around them. Jackson could hear more things than Stiles could. He could hear the deer in the woods, the owl still hooting in his ear though they had passed by where he was at least five miles back, and Stiles breath and heartbeat. It was steady and relaxing. Jackson had loved the sounds Stiles made though he wouldn't tell the other that. That was too romantic, it made Jackson even feel stupid for feeling like he did sometimes. Jackson snapped out of his thoughts when Stiles put the Jeep into park outside the diner. Stiles gave Jackson a soft smile before they both exited the Jeep, walking side by side, occasionally their hands would touch when they swung next to each other. They didn't dare hold hands outside the Jeep. Jackson held the door open for Stiles, who gave him another smile. He leads Jackson to a booth in the back, Stiles sat on one side and Jackson sat on the other. This was a real date. They could both feel it. Stiles suddenly felt very nervous, Jackson could hear the rapid pace of his heart. He had never been on a date before. Stiles had kissed no one before either, Jackson was his first on two things so far.

"Relax." Said Jackson in a whisper, looking at Stiles, who nodded back as the waitress came up beside their table.

"Stiles and Jackson, never see just the two of you here. Where is the rest of the motley crew tonight?" asked Gina, the waitress.

"Studying, finals are coming up, they don't understand the importance of a D's Diner break like Jackson and me." Said Stiles with a smile, Jackson smiled at how easy lying came to Stiles, it was like a second language to him and he was fluent in it.

"Well, I think I will add free pie for you boys tonight, but first what can I get you. Usuals? Two turkey burgers, curly fries and shakes for the both?"

"That will be great, Gina," Said Jackson, speaking for the first time, she winked to them both as she made her way to put the order in, "you are good at that"

"My dad is a sheriff, I have to lie to fun things or I will never get to do them. Plus keeping the werewolves in town a secret helps with practice. And ya know, us." Said Stiles motioning between them, Jackson nodded. Lying about them was easy for Jackson as well but for different reasons. He didn't want people knowing about his sexuality either.

"Here ya go, boys. Two shakes, your food will be out in a few." Said, Gina, as she placed a shake in front of each of them, before walking back to look after her other tables.

"You look really hot tonight, Stiles, just thought you should know that." Said, Jackson, as he took a sip of his shake, he never had a shake before Stiles ordered one the first time at guys night. He remembered Stiles looking appalled at Jackson's revelation and forced him to try it. The joy on Stiles' face that night was something Jackson thought about from time to time. It also made him feel guilty, Lydia hadn't made him feel like that in a long time, but Stiles could make him feel things so easily.

"I only did this for the free pie, don't think I dressed up nice for you." Said Stiles with a smirk, licking excess milkshake off his lips, giving Jackson a wink. He wished he could touch Jackson but he knew better. He knew as soon as he did someone would see them or Jackson would freak out. Stiles felt so happy just being here with Jackson, he didn't want to do anything to ruin that. He wanted to always remember his first date as a good thing.

They walked out to the Jeep after they finished their meal, both full and smiling. Jackson held the driver door open for Stiles, he wasn't even sure what came over him to do it but tonight had been so perfect. Just laughing and talking with Stiles somewhere they were alone that wasn't a bathroom or the halls in the loft. Stiles cranked up the Jeep, turning towards Jackson with a smile on his lips as he leaned across and placed a gentle kiss on Jackson's lips. Jackson kissed back softly before pulling away and smiling.

"Let's go the Preserve. I don't want to go home yet." Said, Stiles, as he looked at his phone, he had two hours to kill before curfew, he shrugged and nodded.

"All right." Said, Stiles, as he began the drive to the Beacon Hills Preserve. He wasn't sure why Jackson wanted to go there but didn't want to question it. He didn't want tonight to end, he wanted to spend as much time with Jackson as he could. Nothing was said in the Jeep again on the drive back, Stiles pulled on the dirt path and kept driving into the woods until Jackson told him to stop and turn off the car. Stiles did what he was told, licking his lips as he looked to Jackson, Jackson looked back at him before he crashed his lips against the other's, full of lust and hunger, which Stiles returned. He moaned into the kiss as his hands found their way to Jackson's buttons on his shirt. He didn't waste a moment, he slowly undid them, which caused Jackson to pull away.

"What are you doing, Stiles?" asked Jackson, his breath fast in his chest from the kissing, Stiles continued undoing the buttons until they were undone. Jackson's toned torso visible now.

"I was thinking, maybe we could continue with the first." Said Stiles in a whisper, but Jackson heard it like he was talking normally. It took a moment for his mind to understand what Stiles was asking of him. When it finally did, Jackson could feel the excitement building inside of his body, he listened to Stiles heartbeat.

"You want me to take your virginity?"

"Yes."

"Stiles, this is a big deal. I mean, I want to but I want you to be sure." Said Jackson, Stiles was sure. He couldn't fight this feeling inside of his brain right now. He had forgotten his one rule. The rule to never have sex with Jackson cause then it was cheating. Tonight had been perfectly perfect and Stiles just knew this was the perfect night for it. He looked into Jackson's eyes, before moving to the back seat of the Jeep. He said nothing as he pulled off his shirt, looking at Jackson the entire time. Jackson pulled his own undone shirt off, he kept his eyes on Stiles. When stiles pulled off his own pants, Jackson followed suit. When the underwear fell on the floor, Jackson let his own do the same. He crawled into the back seat, moving into Stiles.

"I have condoms and lube in the dashboard. Scott got them for me as a gift for my birthday. I don't think he thought I would ever use them." Said Stiles with a nervous chuckle. Jackson didn't say a word as he pulled them out of the dashboard. He was scared if he said anything it would be the wrong thing and it would ruin this moment and he didn't want that for either of them.

"Do you want to do foreplay or do you want to go for it?" asked Jackson his eyes locked on Stiles', Stiles bit his lips. He didn't want to put off the moment. There would be other times, he hoped, for them to do other things.

"Go for it." Said Stiles, Jackson nodded and put a gentle hand on Stiles' chest, pushing him down onto the back seat. He had only seen what do in porn, but he had fucked Lydia many times, so he knew the mechanic at least. This would be different since Lydia never let him near her ass. He pushed Stiles' legs open, squirting liquid onto two of his fingers, pressing them against Stiles hole. Stiles' shivered at the coolness of the lube, Jackson didn't move his fingers for a moment, Stiles' nod was the only thing that made him continue.

"Tell me if I hurt you, if you want me to stop, all you have to do is say stop. Promise?" asked Jackson as he slipped the condom over his hard, eight-inch cut cock. Stiles watched the latex go over the cock, looking to Jackson.

"I promise." Said, Stiles, as Jackson moved on top of him carefully. This was new for both, Jackson was scared that he would fuck something up as he slid just the tip of his cock inside the tight pucker, causing a grunt from his own lips and a hiss from Stiles'. He didn't move another inch, in fact, he stayed perfectly still.

"Are you ok?"

"Yes, just go slow."

"Of course, Stiles." Said Jackson softly, reaching forward and caressing Stiles' face slowly. The other looked so perfect at this moment, his first time with Lydia was nice but there was something about this. This moment felt better. It felt right. Stiles couldn't believe this was happening, Jackson's cock head was inside his hole. A common occurrence in his masturbatory fantasies, but something he thought would never come to be, but here they were. Stiles' let out a long breath and looked into Jackson's eyes.

"More." Said, Stiles, as Jackson pressed himself inside of the hole more, he went slow with each of his cock, as more of his cock was pressed inside of Stiles' tight hole, Stiles' moans got louder. The pain was intense throughout his body. He had done lots of research online, he knew the pain was a part of it but reading about it and having a cock inside of you causing the pain was different. His breath hitched in his throat as he heard Jackson curse loudly.

"It's all in." Said Jackson, his voice was one of pleasure and disbelief that the hole had taken him all in. He expected Stiles to stop him. He didn't expect to be inside of him right now. Jackson met Stiles eyes, who wrapped his legs around Jackson, the cock head pressed against his spot cause him to scream in pain and pleasure. Jackson stiffened.

"Just move slow, I am scared it will hurt." said Stiles his face twisted in pain.

"It will hurt, Stiles, but I promise to stop if you want me to. I promise if you let me continue, I will try to make it feel as good as I can" said Jackson leaning forward to capture Stiles' lips in a kiss, Stiles returned it as his hands traveled down Jackson's back, resting on the firm ass. He didn't want to stop kissing, but he wanted Jackson to move He moved his hands on the ass to push Jackson into him more, causing both to moan into the kiss as Jackson began to slowly move. His cock pressing against the bundle of nerves inside of the other. Jackson had felt nothing like this. Lydia was tight their first time, but this was on another level. Stiles pulled from the kiss as his head fell back in pleasure. A feeling of intense pleasure replaced now the pain. He wasn't even sure this feeling was possible, but his body was reacting in ways he never knew before. Jackson's thrust were faster now, but Stiles didn't mind, in fact, they welcomed them. The cock sliding in and out of his hole, their loud moans filling the Jeep, this entire scene was something neither of them thought would happen.

"Jackson, you feel so good!" exclaimed Stiles in a moan, screams of pleasure escaping not long after.

"Stiles, you got that backward. This ass is perfection." Said Jackson, he could feel himself growing close, Stiles could feel his own orgasm building, which confused him since he hadn't even touched his cock once since Jackson had been inside of him.

"Jackson, I feel like I will explode"

"Then let it out for me, Stiles. Show me how I made you feel.": moaned out Jackson, his thrust speeding up. The intense pleasure was causing them both to feel things they haven't felt before. Stiles leaned forward, kissing Jackson hard on the lips, sliding his tongue past the full lips, Jackson let his own tongue fight against Stiles. Tasting him in a kiss like this was different. The desire seeping off of Stiles was like a drug for Jackson at this moment, he closed his eyes as they both broke away from the kiss both crying out the other's names as Stiles' cock erupted between them, coating his chest and abs, Jackson's release came deep inside of Stiles, filling the tip of the condom, he was sure it was almost too much for the thin layer of latex to hold. He fell down on top of Stiles, their breath was filling the silence in the car. Neither one of them spoke for five minutes and neither one of them moved. They both knew as soon as one of them moved the moment was over, neither one wanted the moment to end yet. It had to last for just a little longer. Stiles was the first to speak.

"Thank you, Jackson." Stiles said, biting his bottom lip as Jackson looked up at him and chuckled.

"Thank you, Stilinski. That was the best." Said Jackson, reaching up and letting his thumb slide across Stiles' chin.

"Let's stay like this for a few more minutes" said, Stiles, as he relaxed underneath Jackson, Jackson didn't care, he wanted to just be here at the moment, not sure if this would change things once they got dressed and went back to their own houses. Stiles had a similar fear in his own mind because at this moment he knew he was in love with Jackson.