The fact that he’s asking what answer would make you happy is already a red flag.
If something bothers you, make sure you clearly communicate it through both your words and facial expressions. If you just gloss over it with a smile, it’ll become the default.
They sound like troublesome papas (male supporters) to begin with, so if you have another offer, I think it’s perfectly fine to part ways with this one.
When someone says something that doesn’t match their other behavior, it really bothers me and I can’t focus. So personally, comments like that are enough to put me off seeing them again.
I can’t tell yet whether he’s genuinely into verbal domination or secretly hoping for free sex and an overnight stay. But as long as he’s properly giving you your allowance, why not assume it’s just part of his kink and play along?
You can simply say, “You don’t need to give me any money,” or “I’ll stay over tonight.” If you want to play it up, maybe say something like, “You don’t have to give me any money, so please use me however you like. I’m your sex slave,” or, “I belong to you. I’ll stay over or do whatever you want, so please let me stay by your side.”
If he ever says, even as a joke while sober, “You said you didn’t need an allowance, right?” then look like you’re about to cry and say, “That would be a problem.” People who enjoy verbal domination as a kink are usually that way precisely because they’re the opposite in real life, so I doubt he’d say something like that while sober. If a guy does say it seriously while sober, you’re probably better off cutting him loose right away.
To explain the psychology a little more: a man whose kink is making you say, “I don’t need any money,” probably has that desire hidden somewhere deep down, but he likely also feels conflicted about having it in the first place, since it’s a rather degrading desire. That’s why he may actually be the complete opposite when he’s sober. The gap between how someone acts sober and how they behave in bed can be like that—which is why people with unusual kinks like me can actually be very nice in real life.
In a soft voice, say, “I’m only saying this to help set the mood,” and then tell him everything he wants to hear.
I’m sure there are people with that particular preference, but finding several of them sounds like you’ve really hit the jackpot.
The guys who want to stay overnight are usually the “second-round” type, and they’ll often make a move on you out of nowhere while you’re asleep in the morning. Negotiate for double the allowance.
