Alex sighed as he packed his Christmas presents in his car. He hated that he had to leave his dad but of course he had to make it home for Jack. So he wasn't sure if he should be excited or upset, as much as he loved Jack he really didn't feel that great about leaving his father and Kyle.

"You're thinking about something, what is it?" Kyle asked, coming from inside dressed in an oversized hoodie and what Alex was pretty sure were leggings, but he didn't question it.

"Nothing...I just kinda feel bad leaving is all."

"Don't feel bad. Your dad gets that you love someone and want to spend time with him. I get it too...how are you guys anyways?"

"We're really good. Jack is really eager for me to meet his family...I just wish our relationship wasn't so complicated."

"You've gotta work with what you've got...just don't do anything stupid...especially with Oli. I know you guys can trust him if you decide to, but if he wants you back or anything promise to steer clear, okay?"

"I promise...can you promise me something too?"

"Course I can."

"Don't rush into anything with this bookstore guy, okay? I'm still really shaken up about what happened with-"

"I know Lex...I'm still shaken too. I moved dorms and everything after we broke up. I still freak out when Austin so much as holds my hand...he knows what happened too, we're moving slow."

"I just have to make sure, you know that. You're the brother I never had, if anyone else hurts you...I don't know what I'll do."

"Well no one will. Now c'mere you big sap." Kyle opened his arms, motioning for Alex to hug him. So he did, wrapping his arms tightly around his friend's waist. Before he could really register what was going on Alex felt hot tears rolling down his cheeks.

"Gosh, I wish someone told us life would be this hard before we graduated high school." Alex said, still holding onto Kyle.

"I know." Kyle mumbled back, now making it evident that he was also crying.

"But hey, at least our lives are made for TV like we always wanted, yeah?"Kyle laughed at that and pulled away from Alex, immediately wiping his tears away with his thumb.

"I guess so...come on inside for a little longer, it's cold out here."

Alex just let Kyle lead him into the house. Sometimes he just forgot how he and Kyle could be. Two overly sentimental idiots that happened to not be ready for the world at all, but were taking it on as best they could. And to be quite honest Alex wouldn't want any other best friend to take the world on with.
-
Jack wriggled his skinny jeans on over his lingerie and stockings. Sure he wouldn't be going over to Alex's for another few hours but he'd rather get everything on now rather than later. Especially after he'd taken the time to shave literally everywhere. Which also felt remarkably strange, the feel of the soft stockings on his skin was much different from before when he was covered in hair. He actually kind of liked it, although if he were to keep up this shaving thing or not...well that was still something he wasn't sure on. But he was leaning towards never doing it again, it was too much effort and now he finally got why Cass always told them that showers weren't for relaxation.

Jack made his way into his father's living room, joining his dad and brother. Of course neither of them would notice the sudden shift in his temperament or in what was going on below his belt. But he'd rather they not know what was going on in either of those departments.

"Jay, when do you have to be back home?" David asked as he put a DVD into the player."I'm meeting with a few friends at six...honestly I have no idea when Mom wants me back."David nodded already sensing that it wasn't just friends that Jack was going to see but he said nothing. Which Jack was greatful for.

"So both of you are staying for lunch?" Their father asked from where he sat in his arm chair.

"Yeah... hey Dad, where's the hot chocolate?" Jack asked. Before his parents divorce they'd always watch Home Alone and make hot chocolate with excessive amounts of whipped cream and red and green sprinkles on top. And right now that tradition seemed pretty darn nice. Jack needed something to calm his nerves because in less than seven hours he would be going to Alex's place. Which meant he'd be losing his virginity and all around being exposed to a completely new territory. So he couldn't help but be shaking in his boots.

"I already made it, the mugs are on the counter."

"You guys are the best." Jack said with a smile and moved himself into the kitchen. Maybe his dad and brother didn't know exactly what was going on, but they knew him just well enough to keep him calm before he had to go.
-
Alex opened his apartment door and slumped against it once it was closed. Sure he was happy to be home and only two hours away from Jack coming over but it didn't mean that he hadn't started missing his family.

He headed straight into the kitchen to start baking cookies before doing anything else. He knew Jack had mentioned that he loved sugar cookies so he'd taken the liberty of making the dough before he left for his father's house. And since it was his and Jack's first Christmas together he did want everything to be perfect. So he may or may not have already gone through the pain staking measures of decorating his apartment before he left for his father's. Really there wasn't much more he had to do other than finish baking and change his clothes. After that Alex just had quite a bit of much needed down time on his hands. And what better to do with spare time than read a book?
-
Jack parked his car about a block away from Alex's apartment, and if he wasn't nervous before he was definitely nervous now. Sure Alex didn't know exactly what Jack was counting on happening tonight, hence the whole present thing, but he couldn't help but be extremely anxious. But he did his best to pull himself together and act normal before grabbing his boyfriend's present and getting out of his car.

"Hey cutie." Alex smiled after he'd opened and shut the door behind Jack.

"Cutie, since when do you call me that?" Jack teased, smiling at his boyfriend, feeling some of his nerves subside.

"I dunno really, but it suits you. You are adorable after all."Jack just smiled and handed Alex his present of which he'd wrapped in red, green, and white striped paper.

"Do you wanna open gifts now? I made cookies and we could watch Nightmare Before Christmas on my laptop after." Alex sputtered out, tense about something but Jack knew he'd tell him when he was ready to. So he just nodded and laced his fingers with the elder's.

Soon enough the pair were nestled on Alex's couch across from the small Christmas tree Alex had set up.

"Okay, you open yours first." Jack said, smiling before biting down on his lower lip. Alex grinned and began tearing at the paper revealing a white box.

"Hm, do you think I can guess what it is?" Alex asked, his hands ready to lift the box's top off.

"I dunno...maybe."

"Is it a puppy?"

"Really funny. Just open it."

"Okay, I'm opening it." Alex laughed as he pulled the top off of the box. "Aw, you got me a new beanie...and a cook book? What my cooking isn't god enough for you?" Alex teased.

"No, nothing like that. I just know that you like cooking for yourself, thought you'd like it."

"I know, I'm just teasing." Alex smiled and pecked Jack on the lips. "Thank you. They're both very thoughtful gifts."

"You're welcome." Jack murmured, leaning forward, planting his lips on the elder's. Alex pulled away before Jack was really able to get into it, which usually he'd be fine with but tonight it just made him feel insecure.

"You've got a present to open too babe."

"Right." Jack chuckled and bit his lip, pulling away.

"Are you alright?"

"Yeah, I'm fine. I just still can't believe that I'm spending my Christmas with the most amazing guy ever."

"Whatever you say." Alex said with a shrug before handing Jack his present, unlike Alex's it was in a red bag with white tissue paper sticking out of it.

And unlike his boyfriend Jack wasted no time pulling the tissue paper out and getting to his gifts. The first item he'd pulled out of the bag was a Taking Back Sunday CD, which he found more than acceptable. Next was a black beanie, which Jack found pretty funny. He and Alex had both thought to get each other the same item for a present and in a way it was kind of sweet.

He kept going into the bag, shocked that there was more there. He smiled when he pulled out a blue,black, and white plaid shirt that happened to look a lot like Alex's favorite plaid shirt except with a different color scheme. The last thing he reached in for was something knit, and Jack had a feeling he knew exactly what it was.

"A Christmas sweater?" He asked, looking over quizzically to his boyfriend.

"Yeah, just unfold it."

So Jack did, smiling wide once he saw it, it was the exact same sweater that Alex was wearing. And if that wasn't the cutest thing, well then Jack didn't know what cute was.

"Wanna put it on?"

"Of course."Soon enough the pair were snuggled up on Alex's bed, watching the Nightmare Before Christmas both with a sugar cookie in hand. To be quite honest Jack had forgotten why he was so nervous, he was sure those nerves would return but right now he was content. After all he was wearing a dorky but very cozy sweater while cuddling with his boyfriend and watching one of his favorite movies on his favorite holiday. He had absolutely nothing to complain about, in fact right now was absolutely perfect and know what, Jack wouldn't change it for a thing.
-
The movie was over and Jack wasn't wasting any time what so ever. Nearly right after the movie was over he'd began kissing Alex, working the older boy up.

He wasn't sure he had mentally prepared himself just yet, of course he was sure he was emotionally and physically prepared but mentally...not so sure. He just hadn't wrapped his head around it...at this very moment he was working towards losing his virginity. And that was a little more than mind blowing to him.

Alex flipped the pair over, catching Jack completely off guard. He was so used to Alex being on top of him but tonight Alex was letting Jack take the lead. Which was a change that Jack wasn't sure he liked or not, but he was going to use it to his advantage. He placed his legs on either side of Alex's, beginning to grind down just subtly, kissing all the while.The elder wrapped a leg around Jack's, pressing him closer as he pushed his hips up.

"Shit." Jack breathed into Alex's mouth.

"Take your shirt off." Alex instructed as he lightly pushed the younger boy off of him so that he could do the same. Jack followed his instructions, ripping his sweater off, almost giggling at the fact that he'd forgotten that he was wearing a shirt underneath it. But he fought that urge and pulled his shirt over his head, tossing it on the floor before leaning back over his boyfriend.

Alex pulled Jack back onto the bed by his hips, pressing their lips back together much more gently this time. It wasn't lust filled or greedy. But it was sweet, simple no tricks, no teasing. He was just holding the younger boy close, each of them lying on their side, their legs tangled together, kissing him tenderly. There was no rush behind it and that made Jack a lot more relaxed. In fact with each second he could feel himself giving more and more into Alex's touch, barely paying attention to the elder's hands inching down.But of course when he felt Alex's hands on his ass, pressing his hips forward, his hormones took over and they were back to grinding against each other. Jack becoming needy and longing for more attention.

"Shit, Jack slow down." Alex mumbled, pulling back from the younger. "Don't rush, okay?"

"I just want more." The teen mumbled back, slowly rocking his hips back and forth. Alex just smiled in response and went back to kissing the younger gently, taking his time. Which really pissed Jack off, just slightly. It wasn't just that he wanted more but he needed more at this point. He was already hard and his dick was a lot more constricted seeing as he was wearing women's panties. So some attention really wouldn't kill him at this point.Thankfully a few moments later Alex was repositioning them so that they were each standing on their knees before unbuttoning the teen's jeans and pulling them down. But he stopped once they were half way down Jack's thighs, breaking their kiss. Which thouroughly confused Jack until he remembered. He wasn't wearing boxers but instead wearing sparkly, blue lace lingerie, oh and he had absolutely hairless, smooth legs. That was something any boyfriend in their right mind would stop to oggle at.

"Are you wearing what I think you're wearing?" Alex breathed, barely audible, just staring down at Jack's crotch.

"Do you like it?" Jack asked, blushing hard avoiding Alex's gaze.

"You look so fucking hot." The elder of the two murmured pulling Jack's pants down further, letting Jack get rid of them the rest of the way. Then they were kissing again, Alex sucking on Jack's bottom lip and grinding hard into him, making the younger boy whine at the constant movement and pressure. And Alex tracing his fingers along the younger boy's waist and ass over the lace he was wearing really didn't help. Because as much as Jack liked this he was hoping they would go past grinding against each other and sloppy hand jobs tonight. Of course he was still nervous, but at this point he wanted it to happen, maybe his hormones were blurring his judgement but he really couldn't back out now, could he.

Jack pushed Alex back beginning to pull the elder's jeans down managing to get his boxers down along with them. Eventually Alex was kicking off his pants and pushing Jack down to lay on the bed. He began kissing him from his lips to his jaw and all the way down to his naval, still pressing on going lower and lower until he met the bulge that was pressing against the lace that covered it. Before Jack could even tell Alex to stop stalling he was pressing his lips onto the younger's leaking member, slowly bringing his hands up to take the panties off.

"W-wait, Alex." Jack choked out, ignoring how badly he wanted Alex to keep going. "I...I wanna go past this tonight." He bit down on his lip, waiting for Alex's response.

"Like...you think you're ready?" Alex asked, moving from where he was in between the younger's legs to sit next to him. Jack nodded in response. "Are you sure?"

"Yes, I've thought about this a lot. And I'm not wearing lace panties for nothing, so can we?"

"Just say the word if you're not comfortable and I'll stop, alright?"

Jack nodded and leaned forward pressing his lips to Alex's. "Don't worry, do you have lube?"

Alex simply rolled his eyes at that and leaned over to open the drawer of his bedside table. He pulled out not only a bottle of lube but a box of condoms. And Jack figured that he'd been counting on this, just not for tonight.

The elder moved back over to the Jack, brushing their lips together before moving back down to settle himself in between the younger's legs.Then he was back at pulling down the blue lace underwear and kissing Jack's thighs. He was already going back to what he'd been doing before, moving at a dreadfully slow pace, barely tugging on Jack's underwear and running his tongue along the outline of his dick through the panties. And once again before Jack could beg for more he was pulling the panties down the younger boy's long legs and tossing them onto the end of the bed.

Jack bit his lip at the sound of the bottle of lube being opened and looked down to see Alex coating his fingers, probably with more than the necessary amount. And then Jack was hissing, taken off guard by Alex pressing in a finger. It'd been awhile since Alex had fingered him and he really handn't done it to himself in awhile either, so to say the least there was a certain amount of discomfort.

Eventually Alex was pushing in a second finger whilst pushing them in and out of the younger boy. Which was the cause of quite a few soft moans coming from Jack's lips, a mixture of pleasure and slight discomfort. But when Alex began scissoring his fingers as he took ahold of Jack's dick discomfort wasn't much of an issue for the younger boy. He simply whined and bucked his hips up into his boyfriend's hand.

"Fuck, that feels so good." Jack muttered, biting his lower lip and grasping tightly onto the covers beneath him. Alex just hummed in response before leaning down to take the head of Jack's dick in his mouth.

And if Jack wasn't making any noise before well he was definitely making noises now. Moaning and cursing softly, not wanting this to end as quickly as he knew it would. Because Alex was fucking fingering him, not only gently but he was also going just fast enough that each move of his hand cause Jack a jolt of pleasure. Aside from that the elder had his dick in his mouth, working his tongue along it causing ecstasy to run rampant through Jack's body. So it was obvious that this was a bit more that enjoyable.

But it only lasted for a few minutes until Alex was pulling his fingers out and crawling up from between the younger's legs. Alex pressed his lips against the teen's, Jack immediately kissing back and wrapping a stocking clad leg around the elder's waist.They went back to kissing and grinding against each other, both eager for what was coming next but not wanting to rush it.

A few minutes later and Alex was pulling away reaching for the box of condoms. And Jack couldn't help but flinch at that, he was nervous but it wasn't like he was going to stop Alex. He wanted this to happen, in fact the notion of stopping actually hadn't even crossed his mind until now ; and that was something he most definitely didn't want to do.

Soon enough, maybe a little too soon for Jack, Alex had a condom on and was coating his dick with an excessive amount of lube ; better safe than sorry.

"How do you want to do this?" Alex asked, looking down at Jack where he lay on the bed.The younger blushed lightly, in truth he'd much rather be facing Alex the entire time rather than having his back to him. The thought of not facing him was a little more than bizarre to the teen.

"Just like this, keep facing me." He murmured, bringing a hand up to push back Alex's hair.

"Let me know if anything is too much, alright?" Jack nodded, telling the elder to just keep going. But that didn't stop him from tensing up when the elder spread his legs apart and he felt Alex's cock was brushing against his entrance. "Just relax." Alex coaxed, still lining himself up with Jack where he was sitting between said boy's legs.

Jack took in a deep breath and nodded. "Go ahead." Jack cringed at the sudden pain, even if Alex was going slow he didn't expect that. It was a burning stretch that he was quite sure he couldn't get used to. But he let the elder keep going, inching in slowly, hoping that it would get better. He clenched his eyes shut and bit down on Alex's bare shoulder, barely paying attention to his actions. Alex said nothing of it though, knowing exactly what Jack was going through right now."You okay?" Alex asked softly, pressing his forehead gently against the teen's ; Jack having moved his head back to rest against the pillow. Jack didn't respond for a long while, still trying to get used to this, right now it just hurt like hell even though the pain wad subsiding. "I know it hurts baby but it'll be better soon, I promise."

"O-okay, I think I'm good." Alex began shifting his hips slowly, trying his best to cause Jack as little pain as possible. But the teen's tightly shut eyes told him that his efforts weren't paying off. "W-wait, do that again." Jack sputtered out.

So of course Alex complied moving his hips again, this time causing a moan to escape Jack's lips. The elder of the two gradually quickened his pace, each time making Jack show some sign of pleasure.

Eventually Alex had a set rhythm and Jack wasn't in nearly as much pain as before. Rather than hating every minute of this he was loving it and completely proving himself wrong because he could totally get used to this. Every part of his body was so much more sensitive than usual and he could barely fight back the moans that were forming in his throat.

"Fuck, don't stop." Jack mewled into Alex's ear.The teacher only response was lacing his fingers with Jack's above said boy's head. But he of course gave Jack exactly what he wanted after a long while, beginning to quicken the movement of his hips. Alex leaned down pressing his lips against Jack's. Even though each of them were needy and simply wanting to get off more than anything the kiss was sweet. It completely deflected the atmosphere around them, more romantic than anything else had been that night.

Jack wrapped his free arm around the older boy's neck, his whines and moans getting louder, going straight into Alex's mouth. Right now he was so close to the edge of coming, but he didn't want this to stop. Every shift of Alex's hips was a direct tingle that shot through the teen's body almost making him shudder. Fuck, this was so much better than he thought it would be.

"Ah, Fuck, Lex I'm gonna come." Jack choked out - having broken their kiss, closing his eyes tightly, mouth opening wide.

"Go ahead, come for me baby." Alex reached down with his hand that wasn't holding Jack's to wrap his fingers around the younger boys cock. He pumped his hand quickly just waiting for the younger boy to come. After a few moments he did, shouting out the elder's name with a strangled moan streaking his stomach white.

Then it was Alex's turn, thrusting his hips a few more times before pulling out and taking the condom off. Which Jack almost protested against but he knew either way he wouldn't be able to take much more. So he settled on trying to even out his breathing before tilting his head up to kiss his boyfriend as he came, painting both of their chests and stomachs with white.They lay on the bed for a few moments side by side until Alex got up and disappeared into the bathroom. He came back with a damp towel in hand, having already cleaned his stomach and chest off. The elder of the two leaned over Jack wiping away the messes each of them had made before tossing the towel into his hamper. Jack simply smiled at his boyfriend and pulled him onto the bed to lay next to him.
-
"I love you Lex." Jack said, breaking the silence that they'd sat in for nearly twenty minutes. They were lying underneath Alex's duvet, facing each other with their hands interlocked ; having already turned the lights off, only relying on the moonlight that flooded through Alex's window to see.

"I love you too." Alex smiled, pecking Jack on the lips lightly. "Even when you're wearing women's underwear." He teased, brushing a hand against the garter belt that Jack had never taken off.

Jack smiled at that and nudged Alex's leg with his own. "You're the one who gave the the idea, you always tease me about wearing women's stuff."

"Hey, I never said I didn't like it." He laughed now running his hand along the exposed part of Jack's thigh. The skin soft beneath his touch, much, much different from what he was used to.

"Well I'm glad you liked it. I was really nervous about just looking stupid." Jack admitted.

Alex shook his head and pulled Jack into him, smiling at the teen. "You shouldn't worry about that kind of thing with me. Even if you did look stupid I'd just find it cute." Jack hummed in response before letting out a yawn. "Go to sleep kitten. I'll still be here in the morning."

"Goodnight Lex." Jack said, smiling at Alex's name for him as he shut his eyes. Kitten, he liked that and kind of hoped it would catch on after tonight. But right now sleep was his first priority, he was worn out and he couldn't run from it much longer. He felt Alex's lips press to his forehead before he drifted off completely falling into dreams of everything that had gone right for him. And what would hopefully work out in the future.

Notes

I'm actually kind of disappointed with this chapter. I had really high expectations for it and sadly it did not reach them when I was writing it. And the smut is mainly foreplay, oops. Cause this is the first time I've ever written a "first time" fic. Oh & there will probably be no update next week cause I'm going to Disneyland, yeah.

Anyways I hope you guys weren't disappointed with this & I'm sorry its late.