AN: Ahahahaha did I say two chapters? Because I obviously meant three... The actual date (and smut) that's the whole basis for this installment will be next chapter :)

Thanks to sly for beta reading for me and dealing with my continuing struggles with tense confusion

Dean unceremoniously kicks him out of the frat house early the next morning (though thankfully without testing Cas' willpower with further displays of Dean getting himself off).

"I'll pick you up at your dorm. I'll have someone drop off what I want you to wear with your charcoal suit."

He eyes Dean suspiciously. "How do you know my suit's charcoal?"

Dean just laughs like it's the dumbest question he's ever heard. "Dude, I've been in your dorm room. Didn't think I'd snoop around?"

With that in mind, the whole walk to class Castiel wonders if he did a good enough job hiding his dildo and porn collection. He doubts it - not because they're not discreetly put away, but because given the opportunity to poke around, it's unlikely Dean wouldn't have uncovered everything. The suit was in the back of his closet in a garment bag and he'd been curious enough to look in there, meaning he'd have no qualms about looking anywhere else.

Hell, he probably cataloged all of the stuff his roommate Inias has, too.

His classes are a nightmare. They're by no means difficult. There are no tests today, no upcoming projects to worry about, and (most surprisingly of all) no homework over the weekend that he hasn't already taken care of. It should be the easiest day he could hope for. And it would be, if he weren't so damn curious about what Dean planned for the evening.

(And yeah, maybe it should bother him that Dean's usurped his date night idea and made it completely his own. But he knows damn well that Dean'll take care of him, so it's kind of hard to be too upset.)

Anticipation builds all day, makes it impossible for him to eat at lunch. Which, as Kevin points out when Cas generously gives him his fries, is probably a good thing.

"Fancy restaurants are expensive, wouldn't want to go on a full stomach." Kevin shrugs and talks around a mouthful of fries. "May as well get your money's worth."

He gets back to his dorm room around four and tries to do some reading. He re-reads the same damn paragraph three times before he determines it's a useless venture. He's tempted to jerk off just to release some tension (and yeah, maybe part of the appeal is it would force Dean to punish him for deliberately disobeying him), but he's gotten so used to not being allowed to come. The build up is part of what he craves and he doesn't want to ruin the moment when he finally gets permission.

That of course means there's nothing for him to do until Dean picks him up around 6:30. He's got another two hours of down time and not a damn thing to focus on-

The Harry Potter theme is rapped onto the outside of his door. Cas stops pacing (when did he even start? god he's a mess) and rushes to answer the door.

"Inias, did you forget your key-"

"Definitely not Inias, but hey!" Charlie grabs his hand, shakes it enthusiastically and then ducks by him into the room. Not sure what prompted the unexpected visit, Cas squints at her in confusion and remains frozen with his hand on the door knob.

"You guys really need to spruce up the place. I mean, seriously, not a single poster? I get the whole less is more thing, but this is college. Your one chance to decorate your room in obnoxious posters without anyone judging you - I mean, unless your choice in poster is lacking, then they're totally gonna judge - and all you have is-" She leans forward to squint at the papers tapped above Cas' desk. "Dude, is this your class schedule and syllabi? What the fuck man, you a robot or something?"

"I... don't have any posters?" And though he feels he shouldn't need to defend his (or Inias', for that matter) decorating choices, there's something of an apology in the way he says it.

"Oh, sweetie." And she looks genuinely sad about that, like it's a tragedy against mankind as a whole that Castiel Novak doesn't have a single poster to his name. "I'll take care of it," she says with confident smile that offers no room for argument.

"Charlie, I appreciate the offer, but you really don't have to do that. I don't really spend a lot of time in here-"

"I'll bet you don't." The exaggerated eyebrow waggle makes him blush despite himself, so he gives up. His experience with Charlie makes him think he'd give in eventually, so why put up the fight?

"Did you only come to question my taste in room decor?" he asks dryly.

"That was just a fortuitous turn of events. No, I'm here to drop this off." She lifts up a giant box (how the *hell* did he not notice it before) and holds it out to him. Finally abandoning his post at the door, he walks forward and hesitantly accepts it. "Dean-o wanted me to drop it off, and since I kinda owe him for bailing me out of an awkward situation with an overzealous co-ed a few weeks ago, I was only too happy to oblige."

"What happened?" he asks, voice thick with concern.

She shrugs, red hair falling from her shoulders. "Stole his girlfriend. Didn't take too kindly to it."

The box is a simple white cardboard. Every seam is sealed with tape, Dean's neat handwriting all over it. Block letters read, DO NOT ACCEPT IF OPENED. I REPEAT, MORE DIRECTLY SO THAT THE PEANUT GALLERY UNDERSTANDS: CHARLIE BRADBURY, DO NOT OPEN THIS BOX OR WE'RE NOT FRIENDS ANYMORE.

He takes the box and eyes her suspiciously while he inspects the outside. "It appears to still be intact."

Charlie rolls her eyes and huffs dramatically. "I ONCE ate a piece of pie from a box labeled PROPERTY OF DEAN WINCHESTER DO NOT EAT UPON PENALTY OF DEATH, and suddenly I'm the ridiculous one."

"Charlie."

"Alright alright, geez. Enough with the third degree. So I would've totally peaked, but I wouldn't have said a damn thing. Dean's all tight-lipped about this kinda stuff, except that he's crazy about you, and me and Jo are dying to know anything."

He tries his best to suppress the stupid grin trying to form. Dean's crazy about him. Him. I mean, he suspected and Dean's said as much, but it's nice to hear it from another source. "Thank you, Charlie."

"That's it? No juicy deets about this date night?" When Castiel remains stoically silent, she crosses her arms and glares at him. "I see how it is. But don't think I'm going to let this drop, Novak."

"It never occurred to me."

Charlie punches his shoulder on the way out. "You two kiddos have fun tonight!" she calls as she disappears into the hallway, shutting the door behind her.

It takes a few moments for Castiel to process the whole exchange, but then he's eagerly rushing to his desk to grab a pair of scissors. He forces himself to slow down and carefully cut through the tape. The box is surprisingly heavy for something that should only contain a shirt and tie, and he doubts Dean would've gone through the trouble of scaring off Charlie if it were something so bland.

(Although...)

When he pries open the top, he sees a note folded on top of a bunch of items, each individually wrapped in tissue paper. Cas moves to his bed, putting the box in the center and focusing on the note.

Here's your outfit for the evening. I'm gonna need you to wear all of it - I'll be checking. Make sure you're waiting out front for me. I want everyone to see how fucking hot my boyfriend is.

Charcoal suit, brown shoes, brown belt. No hair product, you look fucking hot with the messy 'I just got fucked by my boyfriend' look you're usually working.

See you soon,

Dean

P.S. Still not allowed to come.

He squints down at the box. There's... a lot of items in there, and he wonders what exactly Dean's stuffed in there. He takes them all out, not opening them up yet, just to see how much there is.

Five. Five mystery items, all of which he'll need to wear this evening. Some are obvious, so he starts with them to prolong the suspense. The first is a plain white button down shirt. Completely unnecessary, since it's not like he doesn't have his own. But it's no doubt Dean's, and Dean has always had a thing for seeing Cas wearing his clothes. Especially in public.

Putting the shirt aside, he reaches for the next most obvious bundle. Much smaller but also plumper, he rips through the tissue paper to find a sapphire blue tie. At first he thinks it's a close match to his eye color, but when the light reflects off it, it seems more that it's similar enough to invite the comparison yet different enough that it'll bring out the blueness of his eyes.

His heart beats a little faster and affection swells through him. He grabs the closest bundle just to distract himself from the feeling. It's the smallest, though not by much, and inside he finds a blue pocket square. It's silk in a muted orange. No doubt something to give just a pop of color but without drawing too much attention. Fuck, he doesn't even know how to use pocket squares. Now he's going to have to look that up.

(He internally thanks Dean for providing him another distraction, otherwise he'd go crazy before dinner.)

Only two left to choose from - the ominously square one, heavier than the rest, and the one that looked similar to the pocket square in size and shape. He briefly considers before reaching for the small one.

The weight and feel makes it obvious that it's more clothing, though he has no idea what else there could possibly be. He suspected earlier that there might be cuff links, but that doesn't seem to be the case. So what on earth did Dean-

Oh.

Oh.

The satiny panties, a deep blue that's about two shades darker than the tie, have orange lace frills that go perfectly with the pocket square. The satiny material seems to have a bit of stretch to it, which is good because they seem like they're at least a size too small. Maybe that's just in comparison to the boxer briefs he's used to.

It's not what he expected - and really, he had no idea what he was expecting - but the idea that Dean picked these out for him... Found a matching tie and pocket square, thought about every single detail-

Great, now he's hard and hours away from any sort of relief on that front.

The last item remains untouched. It's clearly a box, the angular shape taunting him from beneath the tissue paper. His fingers twitch with the desire to open it, but he hesitates to drag the moment out a little longer. Slowly, he rips through the tape that's keeping the paper together, pulls off the sheet and doesn't let his eyes focus on the box until it's completely revealed.

A butt plug. Which... okay, he's not going to turn it down, but Dean already got him one when they first started going out. (Well, first started fucking. Technically the dating part came a few days after.) Frowning in confusion, he turns the box over to read what exactly made Dean purchase him another-

Vibrating Anal Pleasure Butt Plug

"Well played," he breathes out. His mistake for underestimating Dean. How he managed to become so complacent in only two months is a bit of a mystery, but he's willing to admit he was wrong.

Upon further investigation, it appears the box has already been opened. Just to be thorough, he checks anyway, but isn't surprised that the remote is missing.

Yeah, no way his erection's going down any time soon.

With a little over an hour before he needs to be outside to meet Dean, Cas busies himself getting ready. He takes a long, thorough shower. He avoids his cock altogether, worried about where the temptation might lead, and sticks to scrubbing the rest of himself from the roots of his hair to the tips of his toes.

He dries off as quickly as he can and mentally thanks Inias for being out of town this weekend to visit his sister, because now he has to go through the process of getting dressed. Starting with opening himself up and working in the vibrator.

And yeah, okay, he started that job in the shower. But it still takes a good amount of time to stretch himself enough to accommodate the plug. Mostly because he has to ease up often to avoid getting any more worked up. He's probably going to be semi-hard for the next few hours no matter what, but fuck if that means he's going to let himself stay fully hard the whole damn night if he can help it.

(Grazing his prostate doesn't help matters, but when the plug finally slips in it nestles itself against the nerve bundle. Probably what Dean would want, anyway, so he leaves it there.)

Next come the panties. And wow, that's something he never thought he'd try, but here he is slipping them on. They're a little snug and it takes a moment to adjust his dick comfortably, but once in place they feel pretty nice. Like... really nice. Especially when he puts on his dress slacks, zipper and belt holding the soft material flush against his skin. He could definitely get used to this.

The rest is relatively straightforward. He's not great at tying ties (he so rarely has occasion to dress up like this), but he does what he hopes is a passable half Windsor. The pocket square takes a few tries, and a few YouTube videos worth of advice. Despite the apparently wide array of options for folds, he goes with a very basic one that leaves a crisp line of orange peeking out of the pocket.

Cas admires himself in the mirror. He wishes he could see the panties hidden underneath, but each step he takes reminds him of the other two items he's wearing. The slight discomfort of the plug meshes so well with the drag of satin over his ass and cock. It's amazing.

The only down side of this ensemble is that his pants hide nothing. Not his runner's thighs, not his toned ass, and certainly not his half hard dick vying for his attention. He forces himself to breathe deeply and relax, or at least to calm down enough that his constant state of arousal isn't immediately apparent to anyone who happens to look. By sheer willpower alone, he keeps his mind resolutely blank as he grabs his wallet and heads downstairs to wait for Dean.

He takes the steps two at a time, trying to imagine which will be more fun - dinner itself, or whatever Dean's got in mind for after.