more than friendly

@Poppy

Milo stretched, leaning against a desk, watching the sunset and savoring the art club room's nice view. It'd been a productive day for them, a busier weekend, lots of projects getting worked on and catching up between members, as well as open doors to curious wanderers.

Jack had stayed behind to help clean up. That was very kind of him, and Milo appreciated it a lot. They'd already been friendly before, decidedly, but even more so as of recently. Thanks to, well… their questionable choice of snarky wizard boyfriends being best friends. What a coincidence. Jack seemed to be absolutely delighted by all of it- while Milo was a bit more hesitant, but ultimately defeated, accepting of his fate and who he was now associating with. He held no fondness for Valentine Crowther, but he made Vince happy. And hell, Milo really liked Jack, who was abnormally (but not unpleasantly) friendly, and of a weirdly comfortable height to him. So this was… workable. Normal, even.

They were pretty much done, but could stay a little longer, to enjoy the company and take a break. "Hey. Thanks again, Jack," Milo hummed. "I don't hate doing this kind of work, but having you here is still nice." He went back to gazing out the window, for just a little longer before he knew he'd have to snap out of it- then finally sighing and pushing away from the desk when he did so.

Milo eyed and tugged at his t-shirt a bit, which was messy with paint and other art materials. He'd worn simpler, mess-making proof things today, so he wouldn't have to worry about holding himself back in anything. It was good to have even the president get extra dirty sometimes. A little odd for him to be seen so casual looking in public, of course, so he'd brought a change of clothes to switch to after things settled down. And although that had taken longer than he'd assumed when he'd gotten up that afternoon, he still wanted to get into something cleaner, if only to walk back to his room in.

He walked over to his bag, bending over to dig out his other outfit. He set it down on the sofa before kicking off his shoes and proceeding to tug off his especially stained shirt, then shimmy out of his pants, leaving just his pink socks and bunny patterned boxer-briefs. And now he felt like he was forgetting something, but- oh.

He looked over his shoulder to Jack.

"You don't mind this, right?" It was very late to be asking, but nonetheless, he should check. Jack was an easygoing guy, though, as far as Milo had picked up. Didn't feel like the type to be bothered or make a big deal out of this sort of thing, always touchy feely and relaxed. Someone with no concept of personal space probably wouldn't be offended in this situation. Milo was just changing, and they were otherwise very alone, so there was nothing to worry about.

Okay, well, maybe Milo had been wrong. He hadn't been expecting Jack to be the modest, easily flustered type, but life wasn't really letting things be nice and predictable these days. Internal sighing.

He squinted for a moment at the almost comedic reaction, then made a slow reach for his other outfit at the edge of the couch, figuring he should get this over with quickly. Spare Jack's apparent delicate sensibilities? Christ, his face was so red, Milo couldn't help but give a soft laugh. "Why are you so embarrassed? Sorry, my fault, I assumed too much- I won't do it again, so you don't have to feel this awkward."

He paused again when Jack replied, though. Which was it, okay or not? How he was acting was saying one thing, while his words, another. In fact, the words were just a little off seeming, too, but Milo couldn't really place why. Frustrating.

And when Jack moved over to him Milo's confusion fully took over. He eyed the other man quietly. "Anything's fine. Is there a problem here, or not? You're being… wishy washy, indecisive."

"Relax, it's just us here, but I'm not going to judge you if you're uncomfortable anyway. That wouldn't be very cool of me, as president. We look out for each other, right?" He offered Jack a small, kind smile. He reached up to ruffle the man's hair, just on instinct.

Using this as an excuse for encouraging mini-lectures seemed silly, but hey, why not? Milo really cared about his art club members, he wanted to protect them, never do anything to make them feel bad or unsafe.

He wanted to what? Since when was his doing anything part of the situation? Milo was at a loss here. There was definitely a miscommunication somewhere, that he knew for sure, but he couldn't grasp what it was and how. He thought he'd been very to the point, how was Jack coming to a different conclusion? And one he was apparently interested in, at that?

What had Milo just accidentally propositioned him for? The awful, curious part of him wanted to just… shut up and see what happened, before correcting it. So he did. He watched intently as Jack took his hand, and then, then-

Wait. Fuck. Oh, god. It couldn't be, right? This was Jack's overaffectionate nature at work again, Milo's immediate fear was irrational, too surreal. He calmed his jump of heartbeat at the kiss on his hand, and kept waiting, ready to see where this was really going.

He took a moment to process again, and when he did, well. It was going exactly where he'd thought. Just when he'd stopped letting himself assume too early on, his assumptions started being correct. Whoops.

Milo blushed quite fully, ears tinged red, melting a bit at the contact. He didn't know what do do with his own hands now, just hovering. He felt like a fucking asshole for laughing at Jack for acting the same way just a moment ago, especially since this was what he'd been thinking of the whole time.

What the hell? Milo had only just fucking lost his virginity, and even first kiss, earlier that month. And this was already casually happening to him? How did that make any sense? Had having sex opened some kind of gate, one that couldn't be closed again? Was he giving off pheromones or something? He hoped not.

He hadn't pushed Jack away yet- and he didn't have the excuse of being too caught off guard to do so, it was past that point. Even if he did still feel rather… weak. Milo swallowed.

He reached up to cup Jack's face, and used that to help deepen their kiss, shy but interested. He lost himself in it enough to press into the other man, flush against him, and wrapped his arms around his neck, all to be as close and have as much access to him as possible.

Milo had to break for air, breathing heavy now, eyes big and overall a mess. He was too goddamn expressive when in this sort of state, very much a contrast to his usual temperament, it was terrible. "Jack, I... I was just asking if it was okay to change in front of you," he said, in a very small, endlessly embarrassed voice. "Didn't want to walk back to my room covered in paint, y'know? It's… u-um. Shit." Still didn't move back.

Milo felt all too aware of his own lack of clothes now, as well as the continuing buzz and heat on his skin, not going away even with the tone switch. He scrubbed at his own face, mirroring Jack a bit, avoiding eye contact. He couldn't believe he'd been acting like a mature superior before, trying to reassure Jack and then. This whole thing, and the fact that he wasn't really cooling off.

He peeked through his fingers a bit, quietly listening to Jack before responding. "It's fine, I'm sorry too, I didn't mean to- I don't know, lead you on? I should've asked before I started fucking stripping, instead of right after. Anyway, there's no harm done, I'm not…" He trailed off. Were they backing out of this? Was that automatic, expected now?

Milo eyed Jack for a minute, thinking. He'd said he wasn't going to do anything like this, scoffed at the idea of being with anyone other than Vince, who was an exception to a rule. He'd been uncomfortable with these kinds of entanglements all his life, falling in love for the first time didn't mean that would change. Except. Maybe it had.

Honestly, he hadn't looked at Jack in this light before, hadn't fantasized or made plans to flirt and make a move. This was all purely accidental, but the chance was now in front of him- and it didn't feel so unappealing, once he was in the moment. There was no urge to seek these things out on a regular basis... but opportunity was opportunity, wasn't it?

He really was curious, and they'd already started something. Milo had gotten rather, hm, agitated- and he'd rather not let that go to waste, be left unsatisfied and irritable. Plus, he couldn't stand the expression on Jack's dorky face right then, wanted to distract him, fix it. Milo was feeling more bad over that than the awkwardness.

"…We don't have to stop, though?" he said, careful, hesitant. He bit his lip and took one of Jack's hands, pressing and guiding it down his stomach. He led the man's fingers to rest just barely under the waistband of his underwear, flushing deeply. He leaned up to place a little kiss at the corner of Jack's mouth. "Already went this far. Why not see it through?"

Milo didn't really know how to appropriately reply to these kinds of compliments- so when Jack called him hot, he just offered a less than steady smile, and tried not to die from his clashing mix of shyness and excitement.

He felt faint, nearly sick, hands clinging tightly to the fabric of Jack's shirt when the man's fingers dipped down. His eyes fell shut, and his face and ears were practically glowing with bright red. "Oh, oh god," he breathed. This was actually happening. He leaned into the touch, aching, a needy thrum in his body. When kissed, he responded without hesitation, licking at Jack a bit.

Milo squirmed at seeing Jack down on his knees, allowing himself to be pushed and fall back without complaint. Thank fuck they had cushy couches, if he was going to be having sex on one. All the work he'd done for this club was paying off, albeit in the most unexpected way possible.

He held his breath for a moment, fully exposed now and beginning to feel the full weight of what was occurring. He nodded absently to Jack's question. Nothing there was an issue for him, hadn't been since he was a teenager, and that was long since fixed. Milo was perfectly comfortable with his body. And Jack was about to be all over it. Christ. He was really wet.

Milo cried out involuntarily- and had to clutch one of his hands up muffle the noise- as soon as Jack's mouth was on him. His thighs trembled, squeezing and pulling the other man closer, and his toes curled. His head was swimming with bright, overwhelming pleasure, thoughts racing. This was a whole new level of scandalous for someone like Milo. He was being eaten out by his friend, in the art club room, and it felt fucking amazing.

Milo groaned and threaded his fingers through Jack's hair, tugging, petting, and slurring a mantra of 'yes, yes, fucking god yes'. He loved this. He wasn't going to last long, but that was just fine, because he'd be up for more right away. He shook from head to toe with his orgasm, letting out a long whine. After he caught his breath, he pulled Jack up into another kiss, heated and grateful, tongue heavy and everything pressed as close as physically possible.

He wrapped his legs around Jack's waist and dragged his hands down the other's chest while he kissed him breathless, quite enjoying touching this very attractive man, undoing his pants when he reached them. Milo scooted up a bit, palming Jack through his underwear. He quickly lost any semblance of patience, and shoved everything away so he could better get at him.

Milo's face and body burned. He used his grip with his legs to yank Jack forward all at once, bury him inside Milo, take all of him fully. It wouldn't be gratifying enough otherwise. Milo made a choked sound, weak with arousal and catching in his throat, kissing desperate and messy. He felt. Pleasantly stuffed. His chest heaved.