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I’m a gay guy in my mid-30s living in New York. For a year and a half now, I’ve been in a long-distance, non-monogamous relationship with a man in Russia who’s about four years younger than me. We met on Grindr when I was briefly working in Russia. The sexual and non-sexual chemistry was and is amazing. After a few weeks I had to return to America, but we’ve kept in touch with lots of text messaging and video-chatting, and I’ve been back to visit him four times in the ensuring year and a half (once was for work). He’s a pleasure to talk to, the sex is still good, and he’s proven to be very easy to be around and travel with. Another relevant detail is that he’s never been outside of Russia and doesn’t speak any English. This has actually been really awesome for me, as I am an avid language learner, and my Russian has improved by leaps and bounds thanks to all the time I've spent with him.

We’re both employed, and responsible/frugal with our limited means, but that said I’m in a better economic situation than he is, and I tend to pay for things when we go out to eat or book a hotel.

When we were planning a short trip together last summer, he asked if I wouldn’t mind adding an extra leg onto it just for him, so that he could visit his family in his hometown before his vacation was over. I bought him a $200 plane ticket to spare him a two-day train ride, and he was very grateful. On a separate occasion, when he had a costly dental issue arise, I offered to give him money to help, but he refused, and insisted on solving the problem on his own, which he did. I’ve also saved money during some visits by staying with him some of the time at his very Russian communal apartment, with one toilet for nine people. (A shared toilet where you not only have to bring your own toilet paper in with you but your own toilet seat!) It was quite the cultural experience. (He’s presently paying a mortgage for his own apartment, but that place is still under construction.)

Now I’ve always been a pretty kinky person. I'm into pain and domination, mostly submissive, but not 100% so. He’s been pretty GGG in indulging me, and for the few things he’s not at all into... well, like I said, we’re non-monogamous and long-distance, Dan, so that’s really not an issue. Very recently, however, I have discovered a new fetish: financial domination. For years, I’ve gotten off on exposing and surrendering tender parts of me for guys to use and abuse for their own sadistic pleasure and I’ve recently determined that the thought of someone abusing my wallet—"wallet-raping" me, as it is known—is also really hot. While I haven’t indulged yet, I’m confident that having to hand over more and more cash over the course of a single in-person or online session would hurt me just as much as a series of licks with a frat paddle to my bare butt. Who am I kidding? It would hurt more! And therein lies the appeal. As you might expect, there are plenty of self-proclaimed “cashmasters” online who would be more than happy to “drain” me of of my "fagmoney."

But rationally, if I’m going to be unloaded of all that money anyway, I’d rather it be going to my boyfriend, whom I love, and who I know could use it. So when I visit him again in two months, I want to share with him this new interest and ask him if he would like to be my cashmaster, unapologetically helping himself to “what’s rightfully his,” his actions hopefully mediated by a combination of sadism and greed on the one hand, and empathy and restraint on the other. How bad would it be to get wallet-fucked now and then, really? Maybe a few times a week? Perhaps $20 when he wants to go easy; $100 when he wants to go hard; plus the rare marathon cashfuck that’ll leave me sore till next month’s paycheck.

I like him a lot, and it would be really nice if this relationship worked out long-term (however long that ends up being). And if I ask him to try this, and he goes forward with it, I still plan to be generous (in my own frugal way) when we’re out together. Am I setting myself up for trouble by trying to introduce this new element into our relationship? Are there any unforeseen consequences that my current lust is blinding me to?

Concern About Submissive Horny Donations Risking An Intimacy Nightmare

It makes perfect sense you would cover meals that your poor Russian boyfriend wouldn't be eating and hotels where he wouldn't be staying if he weren't eating and traveling with you, CASHDRAIN, but asking him to be your Findom isn't an extension of your generosity. It's what we in the advice racket call "a very bad idea," CASHDRAIN, one that could undermine the good thing you've got going with your sweet Russian guy.

This isn't a casual or purely sexual relationship; I'd be tempted to give you my blessing if it were. This is open-ended, ongoing romantic relationship with longterm potential. If a lifetime commitment is in the cards—if marriage and/or building a life together is something you might want—then one of you is potentially gonna turn his life upside down for the other, CASHDRAIN, and your boyfriend is far likelier to upend his life. (Russia isn't a great place to be gay, as I'm sure you're aware. So if you two do wind up together 4evah, CASHDRAIN, I expect you'll be making your home in New York City and not, oh, the bustling metropolis Гай.) And if he does that for you, if your sweet Russian guy makes that decision, you want it to be a choice he made freely, not a choice he made under economic necessity.

Short version: Engaging in sex play that emphasizes the disparity in your incomes—and your disproportionate power—could sabotage this relationship. It could turn what should've felt like a choice he wanted to make (being with you for love) into a choice he couldn't afford not to make (being with you for $$$$).

Your boyfriend has been careful not to take advantage, CASHDRAIN, and that speaks well of his character. But that's not something he's doing for you alone. Just as you won't enjoy wondering (two years and a dozen #findom sessions from now) whether your boyfriend is flying to New York because he loves you or because he got addicted to your money, CASHDRAIN, he won't enjoy sitting on that plane wondering about his own motives either. You won't want to look at him and think "whore" anymore than he wants to look in a mirror and think "whore."

Hence the balance he's struck: he'll accept your generosity when it comes to meals and travel, he won't accept your generosity when it comes to expenses that are and should be his responsibility, like dental work, mortgage payments, clothing, etc. Attempting to introducing Findom play when your less-well-off boyfriend is being so careful not to take take advantage of you—when he's being so careful to strike the right balance—would be insensitive, inconsiderate, and disrespectful.

So enjoy Findom with others, CASHDRAIN, and please, please, please do it in moderation and run like hell from any idiotic "cashmaster" who makes unreasonable demands.

P.S. Here's a bonus suggestion: find a "cashmaster" who'll drain your wallet on the regular but not for his own gain. Instead find a guy you can really trust (maybe someone you already know) and let him fuck your wallet but the money he takes from you goes into a savings account that you'll need two signatures to draw money from: your Findom's signature and yours. And he'll only co-sign that check for your next trip to Russia. So when you're missing your hot Russian boyfriend and feeling blue, your cashmaster can help bring your next trip to see him a little closer by fucking the shit of your wallet.

P.P.S. No to "wallet-raping." Please retire that term immediately.

UPDATE: Such a great, observant comment from Ross. You know how they say "never read the comments"? Ignore them—at least where my commenters are concerned!


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