I've been following this board for a while but haven't been able to partake in the sugaring world because I couldn't find a way to do it while maintaining anonymity; this is a 'must-have' for me given some professional and personal situations.  Anyway, on a rare strip club visit, I met a very sweet girl who was making ends meet after emigrating from South America.

We've been meeting at hotels 3-4 times per month and she is amazing.  Totally opposite of what one might expect seeing a stripper.  At this point, I'm planning to give her some money to rent us a small apartment, as that is more economical than paying for a hotel every time.  We can't go to her place because she has a young child.

So here's where I need advice: I want to get away from paying her every time we meet.  Would much rather give her a monthly amount and then not worry about it.  I'm thinking around 3k per month (yes, I know it's a lot, but I can afford it and she is more than worth it).  Is there an anonymous way to wire money to her bank account? I know I could buy visa gift cards, but that's a pain in the ass.  I'll do it if I have to, but thought someone here might have a better approach.

Thanks!

...because anonymous money transfers are outside my area of knowledge.  Why not just hand her cash once a month?  Or better yet, follow the accumulated wisdom of this board and give her cash each visit.  It's so much cleaner that way.  No long term expectations or feelings of obligation or entitlement will come up.  Cash per visit (or PPM as most call it) ensures that when you do get together you both actually want to be there! Reading your OP I'm truly happy for you that you've found a lovely playmate.  But if you rent an apartment as you are considering you're moving away from sugar dating and into the realm of having a mistress.  That's very cool if that's what you want.  One last idea, I also avoid hotels partly  due to the expense, partly because I feel creepy having rendezvous in hotels.  I have a nice RV that I use for sugar dating.  The girls seem to love it, It doesn't cost anything when I don't use it, and it's versatile.  I can meet anyone any place any time with it.  Just sayin.  Good luck, whatever route you choose!

Welcome, Dynomite.

 
I have never "paid in advance" in any form, which is how I see your intent to "give her some money to rent us a small apartment" and "give her a monthly amount and then not worry about it."

 
It may work for a while. It may work for a longer time. It may never work at all. You'll give her the money up front. She'll have the money. She'll do what she wants to do with it. If she's working at a strip club, she's getting offers/promises every time she works, plus your money already in her pocket. Ask yourself -- what is it, exactly, that keeps her faithful to spend your money the way you want her to spend it?

 
Since I haven't given a girl advance money before, I can't offer you anything from experience. But I've read enough here to say that the distillation of knowledge/wisdom here is this: If you give money in advance, for anything, be prepared to lose it all in exchange for nothing at all. There are exceptions, of course. And that's your question -- is she the exception?

 
If yes, congratulations. Tell us all about it and help us learn from it. If no, then let us know what you learned.

 
Rockfordfile

It's not clear from whom you're seeking anonymity, but it sounds like a wife or SO.  
There are lots of payment apps but they all tie into a bank account somewhere, so agree cash is the best way to stay anonymous.
You didn't ask.. but this sounds more like a mistress situation than sugar. But in either case the risks of a split can be high (unless she becomes dependent on you, and then it becomes a different issue). Something to consider.

The SB doesn't know my real name.  So I want anonymity all around.  I can get money out of my account, but I want to get it into the SBs account without her seeing a digital trail.  I know many wouldn't agree with paying up front, but it's more convenient for me and if she decides to take advantage, I'll take the expense and walk away.

With regard to the lease, she will put it in her name and I will pay all 6-12 months, plus the deposit, up front.  That way I don't have to worry about the landlord squawking over a credit check.

I'm thinking of doing the monthly payment in the following way:  I have a crypto account as well as a crypto wallet.  I believe if I send someone crypto, all they see is the username on my wallet, which doesn't resemble my name.  I can set up a crypto wallet for her, so all she has to do is open a coinbase account.  She can connect the account to her bank account and convert to cash as soon as I send her the bitcoin.

I think that will work, but I'm still working out the kinks.  I just thought some people here might have better, less complex, ideas.

This seems more complex than I think most of us guys here have dealt with. And as I said, it feels more like a relationship than sugar. But you might consider a long-term Airbnb for the apartment (there are quite a few). Not sure how they verify but you might be able to lease in her name and pay from a crypto account.

If you want almost no digital trace whatsoever, I would get her bank account number and just go the bank branch and make a cash deposit to her account.  The only "digital" footprint would be the video of you making the deposit to her account.

Cash just seems like the simpler option. You can get $50s from an ATM, and even $3000 in $50 bills isn't too bulky. You can offer to accompany her to her own bank ATM if you are worried about her physical security. I have done this with two different gals over the years.  

That way you both avoid all of the hassles of crypto transactions. You would have which you have to buy somehow anyway, so there will be bank records of withdrawals, and I think cash is less likely to raise questions or eyebrows than crypto. That way, she has it in a perfectly normal bank account that will be more secure than crypto, which has way more than its share of scams as well as volatility risk.  

If you are trying to hide from the government because you have a high-level clearance, don't bother. They can find out whatever you do.  

She should file a tax return to avoid any "no visible means of support" issues, perhaps listing her occupation as "entertainer" unless she has a IRL job that can plausibly cover the amounts. Anyway, the IRS has had its budget gutted over the last couple of decade and has been burdened by so many new mandates that all they can manage to do is cover their minimum legal responsibilities. They don't have the time or resources to go after a consenting adult mistress relationship that probably wouldn't generate a penny of extra tax revenue even if they looked into it.

-- Modified on 1/22/2022 4:09:01 PM

Most banks will not allow you to deposit cash to another persons account anymore.  It mostly has to do with banks getting in trouble for money laundering.

I agree and had such an experience depositing cash to MY OWN ACCOUNT! I had already swiped my card and my account was on her screen. I ponied up the cash for a deposit and was asked for state or fed issued ID. The ATM does NOT ask me for ID when I deposit cash.
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Here's another suggestion: tell her to open a separate bank account (savings or checking) for YOUR transactions only and get two ATM cards. If she doesn't want her name on the ATM card / account (do you know HER real name), make it a business account with a non-personal name on the card. You deposit cash to her biz account using an ATM (you'll be on video). She withdraws or transfers it to her personal account at her convenience. The most that you can "steal" from her is the money you deposit. The biz account and her personal account can be at totally separate banks (Citi / BofA; Chase / TD Bank; ...).  
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Another possibility is to use Zelle or Venmo which are linked to your bank account. I think that there's a way to do it so that you only have to know her phone number (linked to her Zelle account) and she knows your phone number and "Zelle" name.