I'm on a letter-answering kick lately...

Dear Mistress Matisse,

I'm thinking about sleeping with someone for money. I've never done this before. He posted on craigslist and we've corresponded. So far I have been really clear about why I'm considering this (money) and what my boundaries are.1 I've asked for proof that he is STD-free.2 I'm planning on first meeting him at a safe, public place.3 This guy seems able to compensate me well (he's offered to pay back my student loans). 4 Do you have advice on a reasonable way to get paid and how much to ask for?5 Can I go about this in a way that minimizes my legal risk?6 Should I ever go to his house or should I insist on meeting in hotels? 7 Should I sleep over? 8

I'm not desperate for money and I don't want to open a business doing this, but this seems like a good opportunity - I like having sex and making some money would be nice. I'd just like to minimize the risks to myself, my health, and my future.

So, Why Not Have Some Summer Fun?

There’s something a bit off about this letter to me. It’s like it almost rings true, but not quite. I’m simply not believing in it. It may well be from a guy, because horny guys always think they’ll get attention from me if they say they’re women. And the unnecessary capitalization in the last line is odd.

Plus, it seems a bit like the writer wants to be spoon-fed. She makes no mention of any research she’s done, even on my blog, about how to manage this. That always makes me more inclined to help someone.

But, just on the off-chance this writer is sincere, I will give her and all of you the fifty-cent answer to these questions.

1. That’s good, but count on having to communicate that more than once.

2. That’s not something sex workers ask for. But if he’s willing to provide it, fine. It doesn’t mean you’re not taking some risk, but that’s part of game. I find it strange, though. Would you demand this from anyone you had sex with or do you mistakenly imagine having sex for money is somehow higher risk than having sex with a guy you met in other circumstances?

3. Once again, that’s fine, but don’t assume just because the man didn’t show up to Starbucks carrying an chainsaw, then he’s a perfectly safe date and you needn’t consider the matter anymore.

4. He’s going to pay back your student loans? Sweet Jesus, that sounds like a lot of money.

5. A reasonable way to get paid is for him to give you the cash. You can certainly make other arrangements, from Paypal to taking a check, but that’s up to you. As for the amount, see answer number four: I think you’re doing all right there. Spoon-feeding moment: If you want to know what other call girls make in your area, Google the words "escort" + the name of your town, and cruise the web pages that come up.

6. The way to minimize your legal risk is A) not to do it, or B) make sure you don’t do it with a police officer. You’ve chosen not to take option A. Now, teaching someone how to break the law and not get caught is not within the realm of this blog. I’m not a lawyer and I don’t give legal advice. The only quick opinion I would offer is: it just seems unlikely that a vice cop would invest a ton of time coaxing a solitary amateur into a committing a simple misdemeanor. I doubt that it would be considered efficient use of taxpayer money. But that’s a risk you take.

7. Completely up to you. Some girls like hotels because they feel physically safer there. Others feel they lack privacy. It’s your call.

8. It's your choice. There actually are no union rules about stuff like this, and I can't tell you what your personal boundaries are.

Amazon would be your best friend at this point. I can’t write you a whole book, but a lot of other women have, and I suggest you read some of them. Best of luck to you.