I don't know what the laws are where TTT works (and this wouldn't be relevant where I live, as sex work is legal here.

But is there a risk of entrapment here? If this is someone she's never met, who's contacted her on Craigslist, and who's offered her money for sex, could it be private detective working for Vindictive Ex-Husband? Or even a cop if she lives somewhere that entrapment isn't a get-out clause? The whole thing sounds very dodgy indeed to me.
@1 - That's pretty much what I was thinking all through the letter. It sounds like some kind of sting. I just wouldn't risk it.
Paying for it is a string.
TTT says, "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 upon reading this letter I had to wonder, what the heck is an "irregular person"? wasn't much help, giving this insightful definition: "a person or thing that is irregular."

Thanks. Internet, fountain of all wisdom.

I'm guessing she didn't mean the secondary definition either, "without symmetry or even shape," as her problem doesn't seem to be lopsided boyfriend blobs. Perhaps its "does not meet specifications or standards of the manufacturer" which could present problems in a potential fuck-buddy, as it can be very hard to get a refund on damaged goods once you've opened the "package." Are they not having "regular" bowel movements? This would seem to be a rather unusual concern for a casual partner since you wouldn't really be around them enough to notice anything more than the most severe bouts of constipation, but I suppose if you've had previous bad experiences, (perhaps involving massive doses of Ex-Lax,) it could be a deal-breaker.

That being said...

Ever hear the saying, "Beware of Greeks bearing gifts?" It means, better check inside those wooden horses before you let them into your panties. Or something like that. Skeezy sex-for-money Craigslist hookups and vindictive ex-husbands aren't just oil and vinegar, they're oil and gasoline. And sadly, it's your kids that will get burned the worst.
@4, for all of your semantic sleuthery, did you ever consider that "irregular" is referring to the frequency of the encounters, not the fwbs?
@5 Gosh dave, I think I knew that, but it wasn't nearly as fun.
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. . . He said he knows others who [pay for sex] and that it just makes things simpler and more straightforward, but it's not obligatory.

I don't see how paying for sex makes things simpler. Seems to me that not getting money involved is simpler. Making it more straightforward? I think I can see the reasoning behind that. If he's concerned that she's going to want more than NSA sex, I could see where he views paying as a clear marker that it's a "business-only" arrangement. Also, she did say that he said an arrangement like this is not obligatory so it's not as if her only choices are accepting the money or not fucking him at all.

I don't think she needs to pass on him for this reason, But she should definitely meet him first in a social setting (and wouldn't she want to do this anyway to see what he's like in person and see if she finds him attractive enough to fuck?)

No one is mentioning what a bad idea it is for this woman to be letting some rando she's never met into her house. Where she lives with her kid. THIS is not "thinking things through."
I recommend she moves away from Craig's List to a regular dating site like OkCupid, which allows users to state they are seeking causal sex, in addition to short- or long-term relationships. I suspect that if she fills out her profile, she's likely to get plenty of email from men seeking NSA sex, but is unlike to draw the attention of law enforcement (assuming that her recent contact is a cop) which probably focuses on a site like Craig's List.

To @8 / sleepyhead's point, a regular dating site may also enable her to more thoroughly vet potential sex partners. After an exchange of email, I'm usually able to find out a good deal of information about people. One also hopes she has a initial call and meeting in a public space before inviting anyone home for sex. And if she ever decides sex work is for her, knowing something about the people she's negotiating with should minimize the likelihood that the person offering her money for sex is with law enforcement or working on behalf of her ex.
This could be a set up in several potential ways:

(1) As others have suggested, this could be a set up by the police. Setting you up to get busted for prostitution.

(2) It could also be a set up by your ex. It could be a friend, or even someone he hired to set you up to look like a terrible parent.

(3) It could be a set up for blackmail. Once you take money, someone could try to blackmail you, using the threat of either the police or the vindictive ex (or both) as leverage.

It may be none of those, of course. Maybe I'm being a bit paranoid. But this seems like a pretty risky proposition to me. I wouldn't do it.
I can tell you right now as someone that does side work on arrangement sites while interning in her career of choice, that 3k is so far out of the ball park for NSA "relationships". There is no one that would legitimately offer that up to someone that was advertising for something cost free. Run, don't walk.
Entrapment aside....and this does have the stench of it....she's feeling creeped out by the whole affair.

Feeling creeped out = I don't want to = plenty of justification to saddle up the nopetopus and nope the fuck away from that dude.

I mean, if he really gets a kink out of sex workers, he can either find a currently working for pay sex worker (who would be happy for the business), or he can role-play with Zimbabwean Dollars (aka monopoly money) which has no value as legal tender.

I'd be noping the hell out of there, though, because this has the stink of entrapment all over it.
I don't even have kids, but for me the "vindictive ex-husband" and custody issues would far outweigh everything else. That's not something you want to take a chance with just for some sexual fun you can, and have been getting, elsewhere.
Another person here whose first thought was "entrapment." One thing that makes this especially suspicious is him asking her to name the amount. He knows she hasn't done this before, how would she know how much to ask for? And I sincerely hope that the bit about him coming over to her place every week would be AFTER she'd met him in a public place.
Sublime @9: She might be more recognisable on OKCupid. See: vindictive ex husband. She's anonymous seeking NSA sex on Craigslist. I'm only surprised that she's surprised at how easy it is to find random guys for random sex.
@7 I might be slightly pessimistic here, but I read "simple" as "I pay you and then I just have to worry about my own pleasure and not do anything to get you off". Possible the guy will try to pressure her into doing things she's not comfortable doing, since he paid her and she should now make sure he gets his money's worth.
@11 You clearly did not read the above.
I thought SOTEMPTED should go for it, but I don't think LW should, purely because of the vindictive ex husband.

LW: If you had less to lose, I'd say go for it. But you've got a lot to lose, and you've got someone who'll want to make you lose it, and this is exactly the kind of thing that'd let him. Bad combination, so it's not a risk worth taking. A woman looking for NSA sex has a lot of options; pick the safer ones.
I dont know, this doesn't sound like a cop to me. Sounds more like a guy who is used to looking for arrangement type relationships, and assumed that's what she wanted too, because craigslist seems like a weird place to look for FWB these days (right? doesn't everyone just use OKC or Tinder? and CL is for sex work? maybe just in my city? nobody dates on CL).

But then, I have been doing Sex Work Lite for years and had such wonderful positive experiences that I was excited for her and when I read her letter I felt like, Go for it!
An attractive woman (YMMV) who is truly happy having sex with no expectation of a relationship can have a really great time and also make some good money providing the Girlfriend Experience. I call it sex work lite because yes its sex work, but it doesn't really feel transactional like that - it feels like a great FWB who leaves a gift on the dresser when he says goodnight.
She should definitely exercise caution - maybe even say no to this guy, and go on a real arrangement website. Seems like she's at least halfway interested, and it could be a good thing for her.
Also, @11 - That was the young gay guy who was offered 3k for a single night. That is indeed way too high to be reasonable. However, in an ongoing relationship, 3k per month is not uncommon.

I also don't think its so crazy for a guy to offer to give money when none was asked for. I don't think it necessarily makes him a creep, or trying to manipulate her, although those are possibilities. Maybe I've just had really good luck. All the guys I've engaged with were truly generous types. It made them feel good to take care of a woman. They were all invested in my pleasure during sex, (at least as much as any other random sample of dudes, if not more) and never tried to hold it over my head. On the contrary, the power was very much balanced. I think that's why it makes sense for some guys to want to pay - they know that an attractive woman who likes NSA sex is a commodity, and they know that she can have a lot of options. Even if she's interested in doing it for free with him, she will then hold most of the power. She may decide she'd rather look for some other NSA buddy. Men (in general) have fewer options for NSA sex with straight women, and so it works well for them to sweeten the pot a little. It gives them some sense of security that they are giving you something you want (besides the "D", which so many others can offer) and thereby keeping you satisfied.
@19: A guy with experience there would not be likely to pay over "market value" for the services and certainly not sight-unseen, with a nonprofessional, this is a scam of some variety and will not work out well for the LW.
@21 he didn't offer to pay over market value for this LW. He asked her what she wanted. Do you mean the young gay gentleman from a previous column? Yes that was certainly a scam or a sting.
@21 He's looking to establish a ballpark, as has been the norm for all the guys ive engaged with as well. Not to work out a formal contract or anything, but just to make sure we're in the same ballpark before we waste our time meeting. I have friends who will have an arrangement that involves a nice dinner, pocket cash, and some occasional clothes shopping, and then I have seen women ask for 10k a month. That racist basketball team owner guy (donald something?) had an actual contract with his mistress/girlfriend where he paid her 150k per year plus provided a million dollar condo and a brand new Bentley. Etc. It's reasonable to establish a ballpark in advance. This is standard in my experience.

Also, in the arrangement scene, its not thought of as "price for services". It's considered a gift, an allowance, "help", "support", etc and is usually treated as such - it isn't just a euphemism. The gentlemen i've been with always gave me a monthly allowance and there was no set of services tied to it. Just an understanding that we would see each other fairly regularly.
I don't see any evidence to point to this being a scam. Nor do i have any evidence that it isn't. I'm just saying - I dont see anything that suggests this is definitely a scam.
All the scenarios you mention cover professionals, not people who ask a person looking for casual sex on CL to convert to sex work. Entirely different context, and thus the red flags.
The possibility of this being real, someone offering to pay for services that were offered freely is very low and the possibility of this working out very poorly for someone in an already fragile situation is very high. If this was someone she knew and trusted the advice offered would be different.
undead ayn rand,

You could be right. But in prettyprettyprettygood's part of the world, using craigslist (as opposed to a dating site or app) is a statement that you accept money. Not strange, craigslist being transactional by nature after all.

With that input, it seems we can't measure probabilities without knowing how craigslist is commonly used where the LW lives. All we can do is propose various scenarios and the weight of their possible consequences.
Undead @24: Agreed, except for the Craigslist. I agree with PrettyGood @19 about the perception, at least, of Craiglist as being for sex workers. It's entirely plausible that this guy was cruising Craigslist for the sex workers he usually finds in their "Casual Encounters" section, quite ready to pay, liked the look of TTT, and figured why try to get a freebie when he he'd been prepared to pay for exactly what he wanted, no more, no less?

That said, I do agree with your conclusion @25. Tell the guy thanks anyway, but if he wants a sex worker, there are plenty out there. TTT should stick with legal activities so long as the vindictive ex-husband is a threat.
@27: " figured why try to get a freebie when he he'd been prepared to pay for exactly what he wanted, no more, no less?"

This is the bizarre standout. I don't really understand the psychology of financial domination well, but I don't think it would make sense here either...
undead ayn rand @28,

You don't pay a prostitute to have sex with you. You pay them to leave afterwards.

In this scenario we aren't talking about findom but NSA insurance.
@15 BiFanDan: I do not dispute that she would be more recognizable on OkCupid than on Craig's List, but I'm not sure what additional leverage her ex would have over SOTEMPTED by her maintaining a profile on a dating site. SOTEMPTED has a right to seek new relationships, and doesn't need to spell out her willingness to engage in NSA sex. I agree with @19 prettyprettyprettygood who notes that Craig's List is more likely than not to be used for sex work. So it's about a balance of risks for herself and with regards to her child's welfare. Being more open, but using a site not primarily known for sex work and that should let her vet potential partners more easily (for her safety and her child's).
A paid-membership dating site sets a higher bar for (1) cops trying to entrap a sex worker - and maybe avoids the assumption she is a sex worker only because she is on CL, (2) the vindictive husband who trolls the free internet to see what she is doing and at least jerk her chain and possibly harass / entrap her, and (3) fakes and flakes. We hear all the time about people on Craigslist who are into the thrill of the chase or fantasy but never act on it IRL. The LW seems to be taking the money offer at face value, but when can anything on Craigslist personals be believed without verification?

She's a woman who wants NSA sex? It's a seller's market! Big time! In a bar, on Craigslist, OKC, POF, etc. If she'd like a little compensation or gifts for being that unicorn, she could drop hints ("I'm stressing about how many hours I'm having to work") with her current two FWBs, add a third (selecting for someone a little better off - she'll have LOTS to choose from) and then, slowly, upgrade her stable of lovers. The less available, less generous, less skilled lovers get dropped from the rooster and another is brought in to audition. Much of that can be done in a cafe - do you like his looks, personality and conversation? Does he instantly pick up the tab? Only then move on the horizontal portion of the interview.
I'd say there is a 10% chance that the guy wants to pay a certain amount of money as a way of saying "thank you for fucking me" that could not be interpreted as wanting a relationship (e.g. gifts that take some thought and knowledge about the other person's wants and interests) that doubles as a firewall - the sex is not even an FWB relationship, it is literally nothing more than NSA sex.

That said, there is a 90% chance that the guy has some ulterior motive or might use the money as leverage to pressure you to do things that are outside your boundaries / comfort zone.

Ultimately, even if he is trying to be generous or nice, he needs to learn that this is a socially unacceptable way to do it as it will drive away women seeking NSA sex.
1- almost every single (straight) guy who posts on CL is getting hammered with responses from "escort services", some of which are very large elaborate organizations with real connections to crime, sex trafficking, etc... I really doubt the police would bother with setting up an sting for something this minor. Are there a zillion other kinds of fraud on CL? Yes, and some of them might make you wish you were dealing with the police. but...
2- there is a very good chance that this guy from CL, is a kinkster of some sort of the other. He figures by paying you, he can make you more likely to "bend to his will" with whatever noxious-in-his-mind kink he wants. It might be that he likes farts. Or pee. Or more. Maybe he likes girls who wear fairy ears and fuck him in the ass. Maybe he just likes thinking that he is paying you to submit to his will while he "sticks it in" and calls you names. Whatever.

If hes not into the same thing you are (he clearly thinks there has to be strings attached), then move on. There are approximately 4 zillion other ads on CL.
@33: "almost every single (straight) guy who posts on CL is getting hammered with responses from "escort services", some of which are very large elaborate organizations with real connections to crime, sex trafficking, etc... "

Shouldn't this make one worry about the guy who can't find a professional through all of this to meet his needs, then?
It might be that he likes farts. Or pee. Or more. Maybe he likes girls who wear fairy ears and fuck him in the ass.

Otherwise known as a Republican Congressman.
@34 he could be hoping to get someone cheaper and classier. he could be honestly embarrassed about whatever his kink is. he could be trying to do something non consensual, which doesnt work out very well when there is a pimp aka businesss manager aka security involved. but I think you are right, it is worth worrying about (for about 0.5 seconds) and then moving on to someone else.

I am speaking from experience. I am probably very similar to the letter writer, in my tastes and interests. I have talked to many guys on CL. There are (shockingly!!!!) lots of men out there who are really embarrassed or weirded out about their sexuality and dont know how to deal with themselves, much less other people. Turning things into a business transaction makes things easier, mentally. It happens.

I dont think its worth the LW bothering to find out. Too many variables, too much risk, not enough reward, and lots of other fish in the ocean. PS Ive had some great luck on POF. Takes time and patience, but worth it.
Sublime @30: If you're advocating that TTT (not SOTEMPTED -- he was the gay guy who was offered $3 grand) put a profile on OKC and not state that she was looking for NSA sex -- in other words, deceive her potential suitors as to what she was looking for in a relationship -- then I can't see how that would possibly benefit herself or them. At least on CL, she can be up front about what she wants. How big a new asshole would we all tear a man who was on OKC pretending to want a relationship when all he wanted was NSA sex?

Undead @34: Read TTT's letter: "I thought I'd search out an additional, more regular partner." SHE messaged HIM. HE may maintain a CL ad in the full knowledge that every reply he's had so far was from a sex worker, and that's been fine with him. Alison described the situation well as "NSA insurance." If he's paid her, he's under no obligation to be romantic or arrange a second date or any of the things previous "NSA" partners may have requested.
@37: You're completely right.

I wonder whether TTT's prospective beau assumed she was a sex worker (or looking to become one) due to mistaken (but predictable) pattern-matching. If all you get are messages from escort services, and then you get a less-overt message from a woman who says she's looking for NSA sex...
sa @36
There are (shockingly!!!!) lots of men out there who are really embarrassed or weirded out about their sexuality and dont know how to deal with themselves, much less other people. Turning things into a business transaction makes things easier, mentally.

Astute observation. That more or less describes my sex life, such as it is.
Add my vote to "entrapment." Dude is either Vindictive Ex-Husband himself behind that profile, hoping to grab sole custody of the kids, or someone playing that role on his behalf. Him pushing the money arrangements on her like that just has that vibe to me. Don't do it!

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