If the Daddy/boy dynamic isn’t something you want (if it doesn’t turn you on and/or you worry it’ll make things weird), and it isn’t something he wants (assuming he didn’t just say that because he thought it was what you wanted to hear), then you definitely shouldn’t “lean into it.” Instead, you should handle the expense of this trip the same way committed couples with large income disparities split the rent. If you were making 50K a year and he was making 150K a year and you wanted to move in together but weren’t ready to merge your finances, you should pay a quarter of the rent and he would pay three quarters of the rent. Same should go for utilities, food, and other expenses.
But you’re not moving in together, KEPT, you’re just going on a vacation, so things can be a little looser. If you can afford to fly coach and he wants to fly first class, he should cover the difference between coach and first-class fares. If he wants to cover the hotel (a major expense), you should cover meals—maybe not all of them, particularly if he wants to eat in fancy places, but enough of them that it will be clear to you, to him, to your waiter, and to the angels and saints watching from heaven that you aren’t a kept boy. (Nothing will make you feel less “kept” than pulling out your own credit card.)
And the first part of the trip is for business and he would presumably be going with or without you, KEPT, you shouldn’t feel guilty about not paying for meals or the hotel on that leg—a hotel room he would be staying in with or without you, meals he would be putting on his expense account with or without you—but maybe treat him to a surprise excursion on that leg of the trip that you can afford. (Assuming either of you wants to leave your hotel room at this stage of your relationship.)
The kind of disparities you describe—in ages, incomes, and the stages of your respective careers—are something almost all couples have faced—or in the case of income and career advancement, something most couples eventually face. But don’t spend too much time thinking about how you’re going to make this work over the long-term; you just met, you really liked each other, and you’re both willing to travel long distances to keep seeing each other. That should be your focus right now, KEPT. If he wasn’t comfortable covering most of the expenses, he wouldn’t have offered to do that. He could’ve spent his vacation time in the city where you live instead. Of course, there’s a chance it was a trick offer—he offered to cover the expense of the trip expecting you would turn it down—and he’s going to punish you in some passive-aggressive way for taking him up on it. If that happens, well, you can go back to dating boys closer to your age and tax bracket and/or well-off guys who don’t play games.
I’m a single and kinky gay man, doing mainly vanilla dating at the moment. Recently, I got dumped by a guy because I fessed up to being kinky. I also told him I believe in God. I realize that might appear contradictory, but I don’t see why both can’t coexist. He told me he can’t date anyone who’s sexually deviant who also believes in “fairies at the bottom of the garden.” Both were equally problematic for him: my belief in God and my kinks. I wasn’t expecting to be both kink-shamed and God-shamed in the same breath. Are there such things as kinky Christians? Where can I find my tribe?—Frustrated About Insultingly Terminating Hookup
One of the kinkiest guys I ever met—dungeon-in-his-basement kinky, flog-you-until-you-are-screaming kinky—was an episcopal priest. So yeah, FAITH, there are kinky Christians out there. But instead of sitting at home alone wondering where your tribe is, get out there and find your tribe. Get on kinky dating apps, go to leather/fetish events, date some non-vanilla guy, make some non-vanilla friends. If you find a welcoming tribe and it turns out you’re the only believer, so long as no one judges or shames you, FAITH, join that tribe. If you meet guys who have a problem with your faith, they don’t get to be a part of your tribe.
As for the guy who called you a sexual deviant… what the hell does he think he is? Without deviation from the norm, there wouldn’t be “normal” gay guys for that asshole to date at all. Some of us may deviate more than others, FAITH, but that’s as true for gay people as it is for straight people.
A man I very casually “dated” for ONE MONTH more than 15 YEARS AGO—a man I have maintained a friendship with ever since—tells his new girlfriends that I am his “ex-girlfriend.” This disclosure causes a lot of unnecessary awkwardness between whoever his current girlfriend might be and me. I’ve told him he shouldn’t do that because I was never officially his girlfriend. For 99.999% of the time I’ve known him, we’ve been friends, compared to the .001% of the time when we were very casually dating. He says he doesn’t want to lie?!? But it’s not a lie to say we are friends! I hate the awkwardness that it causes between me and the women he dates now. They never have a chance to get to know and trust me. Help me explain this to him so he finally gets it!—Never His Girlfriend
He gets it, NHG. The awkwardness he’s creating between you and his girlfriend-of-the-moment—the awkwardness you see as unnecessary and avoidable—is exactly what he wants. Introducing you as his ex makes things awkward with his current, and his current girlfriend’s intuitive sense that he’s either intentionally or thoughtlessly making things awkward makes him a less appealing partner. He doesn’t want a commitment or anything long-term, and instead of being honest about that, he’s weaponizing your existence to erect barriers between him and whoever he’s dating at the moment. He may not be doing it knowingly, but he’s doing it just the same, and it’s a shitty thing to do to a friend.
And the next time he does it, NHG, object and object loudly: “Don’t be ridiculous! I was NEVER your girlfriend!”