Oh, as for pricing, the typical "arrangement" is a weekly or monthly allowance. There's lots of variances: how often are you meeting, are you exclusive with each other. Those are things that should get talked about pretty early on.

Then there's Pay Per Meet, or PPM. More transactional, I've gotten used to it, but I don't really like it, but it's good for starting out. I guess if I was having sex on a PPM basis, I would be really uncomfortable, but it hasn't happened yet.

And I guess I should say, I've only been back at this for about a month, and I've had a lot of dates, but I have yet to sleep with anyone. I would guess most guys are more aggressive that way, but I want to like someone before I have sex with them, not just lust after their body.

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I live, I learn...

I have 2 main scenarios where I would pay for sex. The first one would be a stripper. A woman, of course. For dances and booze but also to get her home afterwards. I feel like the strip club stuff would be a great warmup or prelude for what's next.

The second scenario would be to pay 2 male escorts to have my first DP with 2 dicks. I prefer to get some "pros" because I want to be sure that they will stop in an instant if I say so. Too many things can go wrong with 2 idiots...

I have some other fantasies but they're more or less variations of these. Maybe next year, this year is to finish the mortgage and "be free" afterwards.

Oh, I also have one where I'm paid for a blowjob, but it's pretty common.

I really dislike the idea of paying for sex myself. I don't think I'd ever do it, but I guess I can't be sure.

For really all of your scenarios, experienced kink participants could probably do it for you just as safely. Remember what I said about the communication? Yeah, I think the DP one could easily happen that way. Guys who you've met/dated a little, and already slept with, they'd be willing to help you fulfill your fantasies, and willing to stop the moment you say to, because they already care about you. And know they'll get more later😉 Or, at least I would, were I in that position.

Leaving my scenarios on the side, I romanticize the idea of one paying the other. It's power exchange.