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Hotel restaurants are Caesar's ideal venue, and this one is his current favorite. The women who patronized them were usually travelling, and here in particular, they were often adrift and alone, emotionally if not literally. It's small and modest; not a dive, certainly, but not up to the glamorous standards of some of the other establishments in the city. Most appealingly, the restaurant has booths lining the walls that are small, dim, and out of the immediate line of sight of anyone entering or leaving. The hotel it's attached to is reasonably priced enough that Caesar has taken a room there for the night himself.
The place is mostly empty when Caesar walks in, but it's early, so that's not unexpected. The bartender recognizes him with a smile as he takes a seat at the bar. "Signor Zeppeli, it's been a while."
"Mario, hello. Yes, it's been busy. I'm glad to have a chance to relax." He smiles back. It pays well to be friendly.
"Well, it's been a bit slow here lately, but I'm sure it will pick up soon. We have some new selection since you were last here, would you like to take a look?"
Caesar spends a few minutes looking over their new bottles before he chooses based on Mario's recommendation. The man appreciates the chance to show off his skill at his trade. And the wine is good, as he sips it thoughtfully.
He's only halfway through his glass before a voice breaks into his reverie. "Oh my! Who's that handsome man at the end of the bar?"
Normally it's the sort of thing he'd be pleased to hear, though generally the women he woos are the sort that need to be drawn out more, nervous and unconfident in their own beauty, but eager once given the opportunity. This time, though, he tenses up immediately, because the voice is clearly male, pitched high into an unpracticed falsetto. As he turns toward the source of the voice, his fears are realized—it's Joseph, that much is clear immediately, though less obvious is what the hell he's doing. He's wearing a dress, in a deep red and a size Caesar didn't know even the more specialized tailors around here would make. His hair is adorned with an elaborate flowery ornament, and his face is covered with more makeup than Caesar has ever seen anyone wear, his lips a deep red to match his dress and his cheeks rouged to nearly the same color.
Now he's coming over to take a seat by Caesar, without even waiting for poor Mario to respond to his question. He gives Caesar a look over Joseph's shoulder, a silent inquiry if he wants him to do anything, but Caesar waves him off with a slight shake of his head.
Caesar opens his mouth to say something—probably "JoJo, what the hell are you doing?"—but he's interrupted by his piercing falsetto again.
"You're certainly the best looking man I've seen in quite a while."
Caesar blinks. Joseph wouldn't compliment him like that, even as a joke, unless something else was going on. He can't possibly think Caesar doesn't recognize him? Is this an attempt at one of his pranks?
The moment it occurs to him is the moment Caesar decides it's true—both that Joseph is trying to play a prank and that he genuinely doesn't think Caesar will recognize him. It's the perfect combination of a theoretically workable idea plus lack of self awareness and failure at execution to be perfectly believable of Joseph Joestar.
So in a split second Caesar changes his mind and decides to call his bluff. He smiles, the slow, lazy smile he uses on women when they're looking at him in the way that means they're admiring him. "You flatter me, signorina. I'm sure someone like you has handsome men at your feet every day of the week."
It's a hit, as he sees an expression cross Joseph's face that says he's surely out of his depth. But to his surprise, after a moment Joseph just covers his mouth and titters in a completely unconvincing approximation of a feminine giggle. "And so modest!"
It looks as if he'll need to step things up a bit more to win this one. He rises, gesturing to one of the dim booths with his glass of wine. "Would you care to join me for a while, signorina? We'll be able to talk more easily over there."
"Ah," Joseph's voice is too low for a moment, that flash of surprise there again, but it's gone even faster this time. "Oh, certainly."
The bartender gives Caesar a strange look, but Caesar just says, "Mario, please bring me the bottle and another glass." He can trust him to be professional, and he'll explain himself later.
As they take their seats, Caesar wonders if Joseph was putting on his makeup in the dark. It doesn't look quite as bad when he can't make out the garish details or the hard lines of his face.
"Are you traveling, signorina?" Caesar asks as he takes the bottle of wine and pours it into the second glass.
"Ah—yes, I'm here from Mexico," Joseph says after a pause, "Italy is a lovely country, but I'm at a bit of a loss."
"Is that so?" Caesar says without even reacting to this new layer of unbelievability added to Joseph's facade. It's surprisingly easy to keep following his normal script. "It's a shame to see such a beauty adrift. You'd flatter me to allow me an evening of your company." He offers Joseph the glass and waits for his inevitable explosion.
The explosion doesn't come, though certainly Joseph's painted lips twist into a strange expression. But there's no outburst about what a womanizer he is, about how he can say lines like that with a straight face, or how he obviously only has one thing on his mind. Instead, after looking at him for much too long to be natural, Joseph reaches to take the glass from him.
"Thank you… you're quite the gentleman."
Caesar blinks in surprise. He really isn't giving up the act. He can't honestly still think Caesar hasn't noticed, can he? But no, Caesar's still sure he can think that. Maybe Joseph is hoping to take this as far it will go and then make fun of Caesar for it when he "finally realizes."
Joseph raises the wine to his lips and Caesar smiles to himself as he does the same. If that's Joseph's plan, he's truly gotten himself in out of his depth. Joseph hasn't even been with a woman before, and with his quick temper there's no way he can keep this act up for long before he cracks. He'll just have to show him how it's done.
There is, predictably, lipstick on the rim of Joseph's glass when he sets it down. Caesar tilts his head as he places his own glass back on the table and refills it.
"What do you think? This bottle came with the bartender's personal recommendation."
"It's… good," Joseph says, again after a moment. "Very—fruity? It must be, uh, a good year."
Somehow that sounds the least sincere of anything he's said so far, and Caesar swallows a laugh. Joseph being entirely lacking in culture shouldn't come as a surprise.
"Well, I'm sure the taste of this wine doesn't nearly measure up to that of your sweet lips," Caesar says, sliding a bit closer to make a show of wiping a bit of wine from the edge of Joseph's lips, though in reality all he does is get lipstick on his thumb. Joseph looks properly shellshocked, and Caesar awards himself a point.
Then Joseph recovers, a worrying smirk curling his lips, and Caesar is suddenly more worried.
"Oh my. I'm not sure about that… Isn't that a pretty strong statement to make about something you've never even tasted?" It's only half in falsetto at this point, and sounds more like a dare than a tease.
There's only one way to respond to that, really. Surely Joseph will back off once he takes the bait.
"Then let me see how they taste." Caesar reaches out to cup Joseph's face, his strong jaw a strange fit in his hand, and leans in as if to kiss him.
It becomes more than "as if" before Caesar even has the chance to register that Joseph isn't moving away; in fact he shifts slightly forward, and Caesar is surprised by the warm touch of his lips, pressed crookedly against his.
He pulls back immediately, enough to catch a shocked expression on Joseph's face again. Well. That's not precisely how he intended that to go, but if it works… he starts to smile a little in victory.
But then Joseph snaps out of it, or maybe back into it, covering his mouth and "giggling" again. "Oh, how bold. Did you like it, then?"
He's really going to take it this far? Caesar thinks, but he's already rising to the challenge and getting back into character himself. "Of course. I'm not sure I can get enough."
And he caresses Joseph's face again, moving in for a smoother kiss, pressing their lips together confidently and firmly this time. He can tell as Joseph tenses up in surprise. He doesn't pull away, though, parting his lips slightly, encouraging, as if Joseph is really a cute signorina who has never been kissed before and needs a moment to relax and enjoy it. To his renewed surprise, Joseph does relax after a moment, following Caesar's lead. He begins to suspect he's miscalculated, and triggered Joseph's need to prove he won't be outdone, and wonders how he'll manage to get out of this.
In the meantime, though, kissing Joseph is surprisingly not bad. Caesar doesn't have many qualms about kissing anyone who needs it, but this is certainly his first time kissing a man like this. The angle is different, with Joseph slightly taller than him, and having his solid bulk beside him instead of a slight girl in ribbons and lace is extremely noticeable. But his lips are soft, and now that he's moving in response, not just passively receiving, Caesar feels a flush of arousal go through him. He almost breaks the kiss then in shock, but he can't let an automatic response like that make him lose. So instead he doubles down, sliding closer to Joseph and settling a hand on his thigh. The heat of his skin is obvious even through the fabric of his dress.
That does it, and it's Joseph who pulls away from the kiss in surprise. Caesar can feel his smirk taking over his face. But after a moment that fake giggle comes again.
"That's a good look for you," Joseph says in his bright falsetto, and this time it's him who lifts a hand to Caesar's lips, and when he takes his fingers away Caesar can see they're smeared with lipstick. Caesar flushes with embarrassment, and bites back a sharp comment on how JoJo needs to learn moderation in his makeup application. Instead he just wipes his mouth with a handkerchief.
Joseph still looks triumphant, for some reason, even with his lipstick now uneven and smeared at the corners of his mouth. Caesar tucks his handkerchief away and returns his hand to a higher position on Joseph's thigh to watch his eyes widen in surprise.
"You're enjoying yourself, then?" Caesar says with a smile, caressing Joseph's leg and feeling the fabric bunch up around his hand. The look on his face is deeply satisfying.
"Y-Yes," Joseph manages, his voice only a little higher than his usual register.
The third time it's surprisingly easy to lean in and capture Joseph's mouth again, and Joseph responds more quickly too, the kiss heated and almost natural. Caesar tries not to think too much about how much he's genuinely enjoying this as he pulls Joseph's skirt up higher to slide his hand underneath. There's no way he could mistake it for a woman's leg he's touching; besides being twice the breadth of any woman's thigh he's ever known, he has dense wiry leg hair, and he's not wearing stockings. Perhaps they were beyond the limit of speciality-sized clothing he could acquire on short notice.
Even so, there's something exciting about it—sliding his hand under the elaborate ruffled hem of the dress to touch his solid muscles and hear his distinctive grunt of surprise. Caesar takes advantage of Joseph's lips parting to press his tongue in between them, gaining the upper hand again as he explores his mouth leisurely for a moment before Joseph recovers again. Caesar startles a little at Joseph's heavy hand on his shoulder, but it doesn't push him away, instead taking advantage of his own surprise in turn to take over his mouth. It sends a strange thrill straight to his groin.
This is getting out of hand, and there's definitely no elegant exit strategy at this point, but Caesar finds he still doesn't really want to stop without taking this as far as Joseph is willing to go. Without thinking too hard about it, he moves his hand up even higher under Joseph's dress, until he finds a lacy edge of fabric on his upper thigh. He had managed to find a pair of tap pants to fit himself, apparently. As Caesar trails his hand lightly across the front of them he can feel a very obvious bulge in the silk.
He pulls his hand back then, and they both break the kiss nearly simultaneously, breathless and eyes wide. Surely Joseph can't keep up the charade after that—
But after a moment Joseph "giggles" again, and Caesar starts in surprise. Then he takes a moment to really look at Joseph, see the determination in his eyes, and he understands a little better. Of course JoJo has no experience, and even if he did it wouldn't be like this. Whether he'd meant it as a prank to start with or was hoping for something like this all along, there's no way he knows how to approach the situation now that it's escalated this far. But there's no way he'd admit out loud that he needs Caesar's guidance. So, if he keeps acting like a debutante in some cheap novel, he can at least claim success in keeping up the act.
Well, it's not like Caesar would know what to do if he was actually seducing Joseph and not going through this whole charade. The idea still seems ridiculous even if thinking about it makes him more aware of how his own pants are also a little uncomfortable after that kiss.
So he smiles his lazy smile again and picks up his wine. "Signorina, would you like to accompany me somewhere a bit more private? I've taken a room upstairs for the night."
"My, you're bold," Joseph says, bringing a hand to his chest.
"Too bold?" Caesar asks, smiling over the rim of the glass before draining it.
"...Not at all," Joseph responds. "I'd enjoy that."
Caesar puts a few bills on the table by their unfinished wine. He'll really have to speak to Mario later, but in the meantime—this is fine.
He rises and offers Joseph his hand. "Shall we?"
Joseph takes it as he stands. Caesar loops their arms together as he leads him out of the bar and towards the stairs. The only person they pass on the way is hotel staff, who politely ignores them in the same way they'd ignore him leading a woman back to his room. Caesar revises his opinion of their professionalism here even higher.
Once he closes the door to the hotel room behind them, the single neatly-made bed confronts him again with what he's doing. He turns to Joseph, whose expression in the sharper light of the room betrays more apprehension than he's seen on him so far.
When he sees Caesar looking, though, it vanishes like it was never there. "I'm looking forward to a fun night," he says, quietly enough that he can't make his voice sound like anything but Joseph Joestar making a suggestive comment, and he leans in—down—to kiss Caesar. Caesar's body responds to it immediately this time, and as strange an idea as this still seems, the idea of not doing it now sounds terrible. Joseph has gotten the hang of this quickly, no awkwardness or hesitation as he kisses him deeply before pulling away with a very JoJo smirk.
"I am as well," Caesar says, pointedly putting his hands on Joseph's hips and guiding him towards the bed. "It will be my privilege to get to explore your beautiful body."
"Oh my," Joseph says, unconvincingly, as his knees hit the bed and he sprawls onto it, kicking off his shoes. Whatever he's used to stuff his chest shifts unnaturally as his back hits the bed. Caesar suppresses a snort, and then lifts Joseph's skirt again, the motion itself exciting. Joseph's face flushes. Without lifting the hem quite enough to see, Caesar ghosts his hand over the front of Joseph's silk pants again. His erection is a little less obvious now, probably having calmed some from the walk up, but he can still feel the curve of his cock, and as he palms it more deliberately he can hear Joseph's breath catch.
It's not anything at all like showing a lonely girl a good time, but Caesar's body heats a bit at the idea of making Joseph come completely undone in the same way. So he doesn't linger much longer before tugging Joseph's underwear off, and the way the silk and lace looks against his legs as he pulls it off is somehow attractive rather than bizarre.
"Don't worry, I'll make you feel good," Caesar says, licking his lips as he settles between Joseph's legs. The intense and disbelieving way Joseph looks down at him is already worth it.
He hikes Joseph's dress up higher around his hips and gets his first close look at his cock. It's strangely interesting; it's large even when only half-hard, his hair dark even against his flushed skin. Caesar finds himself taking the time to look it over earnestly rather than just delaying to make sure he really wants to be doing this, and as he stares it twitches a little further upright. Caesar looks up to see Joseph's gaze frozen on him, and he can feel his face warm at the attention. Then, without lingering any longer, he leans in to take the head of Joseph's cock into his mouth.
"A-Ah, Caesar—!" Joseph yelps, and Caesar feels another wave of satisfaction at the reaction. The cock in his mouth doesn't feel bad, either; it tastes clean but faintly salty and musky, and the way the shape presses at his tongue is odd but pleasant enough. This is, of course, very different than going down on a woman, but the lace in his hands as he keeps his dress up out of the way is familiar, and Joseph certainly doesn't have any standards for comparison on his skill. So he doesn't worry too much, just rolls the head experimentally in his mouth and moves a hand to wrap the bulk of his shaft, feeling it as it quickly firms in his grip.
"Caesar…" Joseph gasps again, and Caesar's own cock twitches in his pants. He finds himself falling into ripple breathing automatically as he experimentally seals his lips around him, and when Joseph's hips jerk up and the head of his cock hits the back of his mouth, it hits him on a long exhale, so he doesn't gag, just widens his eyes as Joseph's cock slides further down his throat than he'd imagined would be possible. Even so, it seems like he has taken barely any of it, his mouth full and his lips stretched wide around the middle of his shaft. Caesar finds himself letting out an undignified groan around him.
Joseph cries out again at that, and when Caesar looks up at him he already looks frantic with arousal, and when their eyes meet over his ridiculous dress his expression turns even more intense, and his slides a hand into Caesar's hair.
Caesar holds Joseph's hips down and pulls back slightly before moving down onto him again, seeing if he can swallow him that deeply again. If anything, it's easier this way, when he's expecting it; he just has to focus on his breathing. Joseph's muscles twitch as he gasps. "Caesar," he says again. In fact he can't seem to manage anything else. "Caesar, Caesar—"
"Hmm?" Caesar hums in response, the sound strange and muffled with his cock in his throat. Joseph makes an even more incoherent noise, almost embarrassed, like he's also noticing how quickly Caesar made him lose it.
But he just says, "Caesar—that's amazing, more—" , his hips straining under Caesar's grip.
It stands to reason that Joseph won't have much stamina. Caesar makes a bet with himself that he can make Joseph really lose it before his jaw even starts getting sore, and he starts sucking and moving more actively on his cock. Joseph moans and gasps with no sense of restraint, the sounds filling Caesar with accomplishment and arousal.
It's really not long at all before Joseph says "Caesar," this time with a different tone, desperate, and then "Caesar—" again, urgently, and it only just occurs to Caesar that that probably means something before Joseph is coming, hot viscous liquid hitting the back of Caesar's throat and filling his mouth with the taste of salt. He manages to not choke on it, barely, but he pulls off immediately, Joseph's come dribbling from his mouth and the last of it splattering on his face. It should be disgusting and embarrassing, but he's too desperately aroused to really register those emotions, and instead he absently notices the white splashes staining the red fabric of Joseph's dress as he frantically swallows and blinks water from his eyes.
He rises to his knees and wipes his face on his handkerchief before belatedly realizing that he missed watching Joseph in the moment. When he looks, Joseph is already catching his breath, focus returning to his eyes as he looks up at him.
"Caesar," Joseph's eyes roam over his face, and Caesar can feel his cheeks heat in anticipation of what he'll say. "That was amazing. You…"
Caesar opens his mouth to say something, but he doesn't know what, now that they've given up their charade. What do you say when you just reached up your friend's dress and sucked his cock until he came down your throat and are more turned on by that than anything you can remember? He tries to start but his voice comes out as a raw croak.
Before he can manage anything, though, Joseph suddenly moves, getting an arm around Caesar and using it to roll his back onto the bed.
"What—?" Caesar manages, but by then Joseph's hands are on his pants, feeling awkwardly at the bulge straining the front of them before fumbling to undo his belt.
"Heh," Joseph says, sounding very much like himself now, "You really got into that, huh?" Caesar flushes with embarrassment again, but he can't manage to argue when his cock is achingly hard and Joseph is wrapping his hand around it. "Kind of makes me want to try it out myself."
"JoJo," Caesar says, and he's still not sure what he's trying to communicate but it's good to finally say that after every signorina, even if Joseph's face is still covered with makeup, now running and smeared with sweat.
"What? You don't want me to?" Joseph says, halfway settled down between his legs.
The answer to that question is so obvious that Caesar blinks at himself. "No, I very much want you to." He manages a tiny smirk to try to save that from being as embarrassing as it sounds. "Let's see you try, JoJo."
"Uh-huh. Then check this out." Joseph gives him a returning smirk that says he's not particularly fooled, before leaning in and wrapping his lips around Caesar's cock. Caesar curses at how good it feels, but as he watches he can't help noticing that the remnants of Joseph's lipstick are still smearing on his skin, and he lets out a short, breathless laugh.
"You really need to go lighter on the makeup," he manages, though his voice is still scratchy from his own adventures in fellatio as well as his quickly mounting arousal, so it doesn't sound as critical as he might have hoped.
Joseph can't respond without pulling away, of course, but his teeth skim his cock, and Caesar twitches warily before Joseph adjusts, using his lips properly. He does have a pretty mouth, Caesar finds himself thinking, out of nowhere. Right now it seems crazy that he hadn't ever thought about this before—JoJo silenced from making any idiotic comments by an intense focus on sucking his cock. The idea of it sends almost as much of a thrill through him as the feeling.
He finds himself thrusting up into Joseph's mouth before he's aware of it, and Joseph doesn't fare as well with it as Caesar had, gagging as the head of his cock hits the back of his throat, and he pulls off.
"Sorry," Caesar says, automatically, but Joseph just coughs once and makes a face.
"It's fine!" He says, voice raw. "That was just a fluke since it's my first time! Come on, do it again." And he moves down so his lips are just around him again and pauses there, waiting.
Caesar almost laughs, but doesn't, since as ridiculous as this is it's also incredibly appealing. He lifts his hips more carefully this time, watching as more of his cock slides between Joseph's lips. There's a slight resistance as it reaches the edge of his throat, but true to his word Joseph doesn't gag this time, and his cock presses further into the warm depths of his mouth. Caesar shudders and moans.
Joseph makes a noise around him that sounds victorious, but it feels so good that Caesar can't even bring himself to be annoyed. He moves, pulling almost all the way out of Joseph's mouth before thrusting in again. Joseph's eyes widen, but he manages it, and he moans encouragingly around him. Caesar threads his hands into Joseph's hair, pulling his ridiculous hair ornament out and throwing it to the side.
He keeps that up a little longer, slow shallow thrusts up into Joseph's mouth, watching his face as his lips stretch around him and his eyes flutter closed. But very quickly that becomes not enough, his need frantic. He thrusts in faster and harder, and Joseph almost gags again before gripping his hips to pin him down like he had earlier.
"JoJo…" It's almost a whine, Caesar's whole body burning with want, and he can't even try to be embarrassed about it. Fortunately Joseph doesn't seem interested in teasing him, instead moving down on him himself, sucking lightly and pressing under the base of his cock with his tongue in a way that makes him feel like he's about to come already.
He doesn't come, quite, but it's not much longer at all of Joseph's mouth working on him that he really feels like he can't hold out. Through his daze he feels the vague desire to be more composed about this than Joseph was, so he opens his mouth to warn him.
"JoJo," he starts, and then Joseph takes him in deep and he's interrupted by a gasp and desperately trying not to lose it right there. "JoJo, I'm—you should—"
Joseph hums low in his throat around him, and that's the end. He's coming with a hot rush and a shudder that wracks his whole body, and Joseph is pulling off with hacking coughs. He can't bring himself to entirely regret it.
He does offer Joseph his handkerchief once he comes back to himself enough to be that conscientious of it, and he does take it to wipe his face before discarding it off the edge of the bed. Caesar grimaces, but he might need a new one anyway. This one is now stained with lipstick and soaked with come. At least most of Joseph's makeup has come off now.
"JoJo," Caesar starts again. "...That was good," he manages.
Joseph huffs. "I bet I could do better. But that was still pretty good, huh? You didn't last any longer than me." He sprawls on the bed beside him and pokes Caesar in the chest.
"I lasted longer than you," Caesar says with an automatic scowl, but he can't actually guarantee it. It hadn't seemed like much time at all. He's so warm and full of satisfaction that he can't actually be upset.
"Yeah, yeah," Joseph says, making himself comfortable, though Caesar isn't sure how comfortable he can be in that sweaty and rumpled dress. "By the way," Joseph says, face half turned into the sheets. "When did you figure out it was me?"
Caesar is so incredulous that he just stares for a few seconds of silence before eventually just saying, "I always knew it was you, JoJo. You're very—distinctive."
"What!" Joseph seems a little honestly upset about that. "But I put a lot of effort into it!"
"...I could see that," Caesar says, for lack of anything else to say. "You could honestly have done with a lot less makeup. But I don't think you'll ever be able to look so different I won't recognize you."
Joseph makes a face. "Well, that's just because you know me so well."
Caesar decides not to deny it. "That may be it."
"...Anyway, it worked out pretty well anyway, right? Right?" Joseph says, his face spreading in his obnoxious grin that always makes Caesar's stomach drop a little, though for some reason it's not doing that right now.
"I suppose so," Caesar manages, which is true. Even if they're both a mess of sweat and come and lipstick—there's even a bit on Caesar's pants, he notices—and even if he has no idea what they're doing, he feels so good about it he can't manage to deny it.
"And I'll do even better next time," Joseph says, and Caesar jerks his head to look at him. But he's turned away, settling his head down on a pillow.
Caesar isn't sure whether he means he'll do better at dressing up like a woman or at sucking his cock. Both seem plausible. It's even possible he means both. But abruptly he's too tired to try to clarify or argue, so he shifts up to settle his own head on a pillow as well.
"We'll see, JoJo," he says, looking at the back of Joseph's head with a strange feeling settling in his chest as he closes his eyes.