I'm a 40-year-old hetero woman. (I may possibly be bi—but that's not relevant here.) I've had surprisingly good luck on Craigslist finding good FWBs. I have two partners that I met through Craigslist that I've been seeing for ten months. We have so much fun! But they're irregular, so I thought I'd search out an additional, more regular partner. I met someone who seems very nice. (We met online only so far.) He's busy like me and he doesn't want any kind of romantic relationship, purely NSA. Great! But early on in our emailing he wanted to know what I would like for my time. I explained that I'm not a sex worker but if paying me for sex is something that gets him off, then I would consider it. He said he knows others who have such an arrangement and that it just makes things simpler and more straightforward, but it's not obligatory. I guess he means it will make me more committed to our set one-hour date each week. I am a student and single mom, so it would actually be really helpful to get a "gift" for having fun each week. He wants to know how much and I'm clueless. I'm also a little uneasy about the whole thing. Would this make me a sex worker? Should I avoid it simply because I have a custody agreement with a vindictive ex-husband?

Thinking Things Through

P.S. He would be coming to my home each week. And, is it a bad sign if I don't think I would ever want to tell anyone that I took money for sex?

Taking money for sex makes you a sex worker, TTT, and a vindictive ex-husband is a good argument against doing any form of sex work—even sex work of the bank-shot, GGG-ish, indulging-the-kink-of-a-NSA-FWB variety. Also arguing against this arrangement: your gut. You don't know this guy—you've never met him—and he may be a perfectly lovely, perfectly trustworthy person who's simply turned on by the idea of paying for sex. But you have a lot at stake here, TTT: your kid, that custody agreement, and your desire to keep this quiet. What if this guy turns out to be controlling and vindictive? What if the reason he wants to pay you for sex is so that he can use the threat of outing you for taking his money to manipulate and control you?

The risks for you—not for all people who take money for sex, but for you in particular—seem greater than the potential rewards.

And did you read the advice Mike Crawford had for SOTEMPTED a few weeks ago? Like you, TTT, SOTEMPTED was approached online and offered money—a great deal of money—for sex. Mike's advice for SOTEMPTED included this:

One last piece of advice from Mike Crawford: "There is a pretty glaring red flag here: $3,000 is a really, really steep price for a single date. I'm not implying that SOTEMPTED isn't worth it, but the old 'if it sounds too good to be true' adage definitely applies in sex work. Should he decide to do this, he needs to screen carefully before agreeing to meet in person. The safety resources on the Sex Workers Outreach Project website (swopusa.org) are a great place for him to learn how to do just that."

This guy didn't offer you 3K, TTT, but he did offer to pay you for something you're willing to give him for free—and that trips the "sounds too good to be true" wire. Pass on him, TTT.