Does anyone have any experience being TOPPED for money? Care to share what the best way to drain older wallets is...

I don't have personal experience, but i've known several escorts, "sugarbabies", and a few other degenerates through various sites and IRL.
There isn't a huge demand for twinks in a "mutually beneficial" arrangement. That doesn't mean it never happens since of course it does (also could be wrong about you being a twink but i mean guys/guys in general and twinks are the big attractor in those situations). But dudes are pretty promiscuous with each other and even the grossest guy doesn't have a lot of issues finding young guys to fuck.
Think about how horny you are at 22 - you are now aware that all the other young gay dudes are horny as well and a lot of them have a similar lack of standards. In addition to that, older guys is a common interest - yes, even the fugly ones.

All that said, yes it is possible but not usually "viable" unless you are astonishingly attractive and fun to be around. Ask yourself: why would someone buy you dinner, let you stay at their place while they travel, use their shit, sit in your underwear and watch their tv, etc - when they can find a similar young guy on an endless assortment of hookup websites and fuck that dude for free?

With the bad news out of the way: Yes, seeking arrangement sites work. I forget which is the "best" but they all are pretty similar in function and most guys that would be looking will have accounts on every one they can find. You'll see lots of duplicate listings and some may even be owned by the same outfit. Make your requests modest and you'll have better chance at luck, at least until you find out what your range is.
If you're interesting in hooking in general, that is a lot sketchier and the same caveats listed above apply.
Not that you need my advice, but if i were you i'd lie and make yourself a little younger and lie about being a virgin (or tell the truth if you are). Being the first to put it in your butt would be a draw that others may not have.

Too old.

i'm pretty masc unfortunately, but yeah I do have my anal cherry. so maybe i could get rid of that for a decent bit of cash. sounds difficult though. damn I wish I was a girl.

damn

eh, like I said it's possible in the same way that almost "anything" is possible, but I wouldn't count on it, friend.
not sure what city you are at, but you could go to the doublelist listing for your city (the craigslist replacement, basically) and see just how many dude4dude postings there are and those are all free. It's never been tough for gay guys to get laid, and typically the ones that DO get paid have model looks and are quite feminine.

It still can't hurt you to try. Make sure you aren't posting your face anywhere that you wouldn't want someone to find out. People are very gossipy and you'd be surprised how many people browse hookup sites to find people they know just for funsies. Invest in a burner phone, they are very cheap, and use fake email/name/everything. Not only so your dad doesn't know you're trying to sell ass but for your own safety as well. It should go without saying but there are a small but real percentage of people into this stuff that are not good people.

In addition to arrangement sites, use things like doublelist, AFF, squirt, sniffies... i'm sure you could find a lot others. Most are free, some are not, but all can be utilized as a form of advertisement. You never know, it could be late one night and someone could be striking out, at that point your hairy-sure-thing-hole may start to look more appealing.
Good luck and stay safe, user.

Too old is harsh if you’re cute enough. Give us a pic.

Based, cheers dude. Fuck, I wish prostitution was an easy option for anyone willing to take the metaphorical plunge. Seems like it would be a lot of work.
I don't mind having my pics on a public profile as long as there's no way to trace it back to my actual identity. It'll increase my chances in a small way too.

Posting oneself on Cred Forums is definitely foolish though, sorry dude

Topped? Are you looking for a Dom who will pay? Highly unlikely. You may find a sub who wants to experiment, but that's about it.

Get a job you fucking lazy degenerate.

I'm trying, that's why I started this thread

I helped a cute boy become a sissy faggot a few years ago. Money well spent, now she works in a gay bar in NYC where she is the absolute queen of the place.

Sounds super hot. I wish I'd started down that route at 18, I'm sure if I had I'd easily pass as a woman now! As it is I'll probably just have to do crappy work until I die

It was hot. She started out knowing that she wasn’t really a boy but lacked the confidence to do anything about it. It was as much about that as needing money but I was happy to oblige because it suited my depraved tastes.