“Should I Take on a Sugar Daddy?”

I met this guy who proposed that he basically become my sugar daddy in exchange for sex. I told him I was into friends with benefits sex with no strings attached for free, but he told me he likes to spoil women. I don’t think there is anything wrong with this and it actually excites me. He really wants to buy me things because he wants me so bad. I would give him sexual pleasure without the gifts, but is it crazy to take his gifts too?

I’m looking for a no-strings-attached sexual relationship now anyway, but this one comes with perks. He offered me $75 for a pair of my used panties one morning. Do you think anything is wrong with this? He’s professional and sane, but doesn’t have time for a girlfriend — according to him. Regardless, I don’t want to be anyone’s girlfriend right now anyway. Am I crazy for doing this or should I just be living it up? — Sugar Baby

I say you’re both consenting adults and if you have no reason to believe he’s lying to you about his availability, then your relationship wouldn’t hurt anyone else (other than potentially you), and you should go for it if it’s what you really want. But do keep in mind that you’re fooling yourself if you think this Sugar Daddy-Sugar Baby relationship has no strings attached. Of course it has strings attached. You would basically be providing a service in exchange for goods, which is about as stringy as you can get. If you fail to provide the service — sexual pleasure — in a fashion that suits your “Daddy,” he can withhold your “perks.” Likewise, you may come to be so dependent on those perks, that if they fail to suit you or if your John fails to pony up, you may be tempted to withhold your service.

And if you begin to see it that way — service in exchange for goods — it may be hard not to start seeing yourself as … well, a sex worker. I’m not saying that’s what you would be, but I am saying there’s definitely a gray area when it comes to sex, and your relationship would fall into it. Can you handle that? Can you deal with the strings that would be attached to your relationship? If so, go for it. But keep your wits about you, know what you’re getting into, and be absolutely sure you can trust this guy and that if you say “no” at any time, he will respect your boundaries. If you’re unsure about any of those points, hold off and find someone who would truly provide the NSA fun you’re looking for.

Oh, and don’t sell him your used panties. That’s just nasty.

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If you have a relationship/dating question I can help answer, you can send me your letters at wendy(AT)dearwendy.com.


    1. Jess, you are something else!! LMAO.

  1. ArtsyGirl says:

    Wow this letter makes me uncomfortable in so many ways. I actually advocate for legalizing brothels in America in order to protect sex workers – but I am getting weird vibes off this relationship. The fact that you offered to have a NS relationship without the sugar daddy component and he refused sends up some red flags. Maybe he does like to spoil the women in his life, but the fact that he wants to enter into this relationship insisting that he is going to pay you basically reduces it to sex work which gives him all the power. It might be a control thing or the idea of having a mistress gets him off – I don’t know, but I would proceed with caution. (Also agree with Wendy on the panties thing -ick)

    1. I don’t disagree with you that his refusing the no strings attached sex in favor of this financial situation raises a red flag, and likely makes it about control. But, I think a lot of this depends on their personalities. He might be a “nice guy” who wants to have her be his arm candy, and it makes him feel like he deserves her because of the financial element to the relationship. On the other side, he might be some manipulative control freak that is going to try and push her as much as he can, and then hang the financial element over her when it suits him.

      For her, the risk is that he’s the second type, but she might be very confident and able to handle herself in either scenario. If that’s the case, he likely sees that confidence and wants her to be the dominant one in the “relationship” since he might always have to be dominant in his work/other social commitments. Or, she might not have the personality to stand up to him, and she might succumb to his manipulation – if this is the case, the second scenario is likely to be unhealthy.

      1. I totally think he gets is rocks off by power. Now, just make sure he doesn’t take it too far and want to control everything you do. If you do this, LW, tread lightly.

    2. ArtsyGirly says:

      I can completely see where you are coming from PFG – I am mostly thinking worst case.

      There were a few other scenarios I thought were possibilities were that the status of sugar daddy could be a safety mechanism for him – maybe he has been in sex only relationships before and the girl got demanding or wanted commitment from him despite the standing of their relationship. Or possibly it might be indicate a level of insecurity or guilt since he is not going to have a future with her.

      Whatever the case may be, the language of sugar daddy inherently puts him in a position of power in the relationship. For me the one sticking point is that she offered to have a relationship with him minus the material perks and he told her that he wanted to ‘spoil’ her. Friends with benefits and sex only relationships are not uncommon or even considered reprehensible by most of society (the new Rom Com No Strings even addresses this), but the situation the LW mentions strays more into a gray area as Wendy mentioned. The fact that he is pointing out that he will be compensating her rather than just giving her gifts and paying for dinner seems strange – someone mentioned that this seems out of character of a typical sugar daddy situation.

      BTW there is a great book out called Some Girls about a woman who decided to become a part of a seasonal harem for money when she was 18. It is really fascinating and a true story.

  2. I agree with Wendy and ArtsyGirl here on quite a few levels. LW will need to reconcile herself to the idea that she is, in fact, exchanging sex for material goods – even if it is exciting. As for the “sugar daddy,” I’ve got to think it’s about power. What happens when the LW wants out (even if it is NS)? Will he remind her of her “obligation” to him? Even if the items/money are freely given, I anticipate that accepting these things from him creates “obligation” that will make it difficult for her to escape once she’s ready to leave. I think that if the LW proceeds with the relationship, she’s going to need to develop an escape plan, as well as where she wants to draw the line in terms of things she’s willing to do (i.e. what if he wants to pay for unprotected sex? Or a particular act that she’s not comfortable with?).

    1. Rachelgrace53 says:

      I was JUST thinking that the exact phrase “escape plan” needed to be said. This is what I was thinking exactly.

  3. Jess of CityGirlsWorld.com says:

    What Wendy said 🙂

  4. I think as long as she can maintain control over what she does/doesn’t do and doesn’t feel obligated or coerced in any way, I don’t see any problem with it. Personally, I wouldn’t like the idea of _cash payment_ for services/items, but it’s not that fundamentally different than being given gifts for the same things. (What’s the big deal about the worn panties?)

    He obviously likes to feel powerful and in control, and he obviously likes the element of “buying her”, so she needs to be aware of this and feel confident that she can handle herself. He rejected the “no strings attached” sex for a reason – this is a scenario he wants to have her in.

  5. Yeah, I’m not a huge fan of this at all. I’d have to say don’t do it, it just seems creepy and all about power.

    1. Sex is often about power. Don’t you think?

  6. WatersEdge says:

    Definitely set boundaries in your head of what you’re willing to take from him. I think some good ground rules might be 1) Don’t take anything that you need- tuition, a car, bill payments, etc that keep you at his mercy 2) Don’t take anything over a certain value, maybe $1,000 3) If you start to get a controlling vibe, end the relationship immediately before it gets worse. If he tries to tell you what to do out of the bedroom, or he wants you to do degrading things you’re not comfortable with in the bedroom, definitely end it.

    I think that you might want to go into this relationship with the expectation that this guy is a little weird (who wants to pay for sex when someone offers it for free??) and that you’ll have to walk when he inevitably crosses a boundary with you. Otherwise- have fun!

    1. I just really agree with the setting boundaries. I think where women in this situation can get in trouble is when they accept things they need (aka rent) or they are with a dangerous man. You don’t want to have the rug ripped out from you so make sure you have your own money in your own account that cannot be touched. If I were you, I would have fun!

      Oh. and watch the french movie Priceless. It’s about sugar daddies and sugar mamas. It’s sweet, funny, and classy.

  7. Moonshine says:

    One thing I’d like to point out – you should be aware that you’re not the only girl he does this with. So there’s a high possibility that he has sex with more than one woman at the same time. Are you willing to take on that risk of STDs? And for what?

    About sex in exchange for material things – that’s how I feel about dates. If the guy pays for me, it’s commonly acknowledged that he pays for companionship, not necessarily for sex. So I don’t think about it the way Wendy and other people meant. You can always end it, and say that the things he gave you are for the sex you had, not for the sex you will have. And if you feel he is more generous than you think he should be, you can just decline any of his gifts. (I’m not completely aware of the difference in income between the LW and the sugar daddy. If she’s a student, then a $50 lunch is something significant. If he’s a millionaire, then the same $50 lunch is nothing for him. I guess it’s all relative.)

    And Catie8 brings up a good point. The fact that he asked for worn panties suggest that he has some kind of fetish, which can also bring unusual requests in the bedroom later on. Can you deal with that?

    If you want to have a clear conscience, then just don’t take any gifts, and only give him what you want (in terms of sex). And if at any point he makes you uncomfortable, you can just leave, without feeling that you owe him anything.

    1. Thank you! I had hoped someone else thought of the health issues involved with this! I loved Wendy’s advice but I wish she’d put more stress on the fact that they still need to be safe.

  8. I don’t know that I agree with the advice I’m reading.

    I once ‘dated’ a man (ok – we were just sleeping together) who was very wealthy and was always giving me gifts and paying for things. Mostly he’d buy me dinners out and fancy gifts – but I once found myself in a spot of trouble and he gave me several thousand dollars. In the end he was my friend. He cared about me and I cared about him. It’s this NSA thing that I think is bunk – of course these will be strings. Frankly I can’t think on one relationship in the entire history of relationships that doesn’t have strings.

    Regarding the panties ‘fetish’ – that is nothing. Feet, panties, catholic school girl outfits, etc – just about every guy on the planet is into these things in one way or another. It’s all good, clean fun.

  9. If it makes you feel less skeevy, perhaps compromise with him and suggest that, instead of just offering you cash for certain things ($100 for a blow job, $75 for panties), maybe suggest that you guys just have a friends-with-benefits relationship, and you’d prefer if he’d just surprise you with gifts (not attached to any particular sex act) on a regular basis if he still wants to “spoil you.”

    I’d also clarify with him that he doesn’t expect you to return any of these gifts if the relationship ends or goes sour.

  10. Rich men who are used to getting whatever they want whenever they want can be dangerous if they don’t get what they want, so I would definitely suggest some ground rules right off the bat – such as no vacations with him, no actual cash for sex, no anal, etc. What ever it takes to make you feel comfortable. Just make sure he knows the rules.

    1. Where do you get this ‘most wealthy men’ thing? Is that based on your personal experience?

      I have been working as an Executive/Personal Assistant for the past 20 years – the last 10 of them have been spent in NYC working for/with some of the wealthiest men in the US – I have never known any of them to be ‘dangerous’ when they don’t get what they want. Generally speaking they are competitive, hard working and very careful of their reputations – none of these guys wants to land themselves in a sex scandal and thus they tend to be very private and careful with their relationships.

    2. I said ‘can be.’ There’s lots of stories out there about rich abusers who get away with things because they can afford lawyers and the like to shut people up.

      I think its lovely that the rich dudes you know are all awesome. All I’m saying is a rich man scorned is far more dangerous than a poor man scorned.

      1. Pshhh. You know what else there are lots of stories about? Young couples who park on a dirt road in the forest to make out when all of a sudden an escapes mental patient with a hook for a hand attacks them oh no!!!!!!!!!

        The vast majority of people are not evil, so why must we assume that all the LW’s are in relationships with people who are the exceptions to the rule?

        Have fun? Yes. Keep your eyes open? Of course. Watch out! He’s rich and will cut off your fingers to make a necklace and then bribe everyone so he never gets punished? Maybe that’s a little much.

        Besides, it’s quite likely that more poor people than rich people have gotten away with murder, so by your logic, to maximize her safety she really should go with the sugar daddy!

  11. This just doesn’t sound like a good idea in my opinion, cause when it comes time to when you do want to have a relationship again, you may have skewed ideas of what’s expected in return.

    1. elisabeth says:

      This. These are my thoughts.

      Even if it’s just a fun “fling” with “no strings attached” (I agree with Margaret that any relationship is going to have strings, whether you acknowledge them or not), this has the potential to change your expectations of relationships in the future. Are you going to be satisfied with a relationship where the man doesn’t have the ability to spoil you? Are you going to be able to separate yourself from the quality of the lifestyle that you seem about to accept?

  12. This really weirds me out. Like Wendy said, two consenting adults can do whatever they want. But there are plenty of times in the course of this column that Wendy, as well as commenters, will tell someone that despite what they may WANT to do, it’s probably not good for them. Usually, that’s a situation in which someone wants to stay with a guy who isn’t treating them well or who doesn’t want to accept that it’s over.

    Everything that Wendy said is right, likewise for the commenters who also said that there ARE strings, it creates a strange power dynamic. But it also cheapens intimacy and sex. I’m not a super traditionalist; I’ve had several friends with benefits relationships. But I think that in the future, when you may decide to be with someone because of love, it might mess with your head and affect the way you see sex in your own relationship.

  13. I don’t really see any fundamental difference between this and actually dating someone who gives you gifts. Either situation could lead to an unwanted control dynamic, and either situation could simply be fun and enjoyable. Obviously, since you’re both clear upfront about the terms, it is different than dating, but not all that much, and almost not at all if the dating is non-exclusive. Try it out, end it if it’s not what you like.

    Do keep in mind, though, that once you start this, you’ll always be someone who opted to get paid for sex, and that might get revealed by him. It’s fine if you’re cool with it, and I don’t care either way, but do remember it is a line you’re crossing that you can’t uncross.

    1. WatersEdge says:

      I disagree with your line about how she’ll “always be someone who opted to get paid for sex, and that’s a line that you can’t uncross”. I see her as someone who “chose to accept gifts and money from a man who she wanted to sleep with for free”.

      To me, what she’s doing doesn’t make her “dirty” or “tainted”, and I think that’s implied in your comment. Maybe I’d agree if she entered the situation thinking of money first, but she wants to sleep with this guy anyway and the gifts are a perk.

    2. I feel like “someone who opted to get paid for sex” and “someone who chose to accept gifts any money from a man who she wanted to sleep with for free” is just splitting hairs. Call it what you will, the same thing is happening in both situations.

      1. WatersEdge says:

        I don’t think it’s splitting hairs at all, I think there’s a huge moral difference. This is an extreme example, but what’s the difference between a prostitute and a wife, then? If I stay home and keep the house clean and screw my husband, and he lets me live there and feeds me, is THAT prostitution? For me, the key is that she wants to bang this guy either way. According to her description, the money doesn’t come into it for her. With prostitution, you don’t get the sex if you don’t pay. But in this situation, he’d get the sex either way. So it’s not the same thing.

      2. Ah, but he’s refusing to accept sex unless he pays. Therefore, I see it as the same thing. To him, she is a call girl. The forcing of payment (gifts or cash still equal payment) is what makes it a sex-for-sale situation.

        As far as your housewife scenario: if all you represent to your husband is a maid and a source of sex, then yes, that’s prostitution an any real sense.

        In this case, he sees value in sex with her only if he pays. She is of no value to him unless there’s a form of transaction.

      3. WatersEdge says:

        I think that she’s only responsible for her own morality. If she wants the sex either way and she has sex with him, then she is not having sex to get money. She’s having sex to get sex.

        If he only wants to have sex with her if she takes his gifts/money, then maybe he is, in his mind, buying sex. But that’s not her issue and that doesn’t make her a prostitute.

      4. What I am saying is that in her life, as it stands, the same thing is happening to her. If she calls it sugar daddy, accepting money from someone who she wants to have sex with, or playing cards on a Tuesday night. Later in her life she might look back and see it completely differently than how she does, or how you or I do, today.

  14. While I agree that this arrangement is between 2 consenting adults, I hope the LW understands this will be a part of her past and she may have to explain to a future husband why she agreed to be a partner in this type of situation.

    1. sobriquet says:

      There are several things from my past that I haven’t disclosed to my boyfriend and I doubt that I ever will. He doesn’t need to know about my past sexcapades.

      1. I realize that no one will ever share everything about their life with anyone and that most embarrassing moments from one’s past won’t ever resurface, but I’ve learned from experience that things can emerge that you expected to never again see the light of day, so it’s still good advice to go into something with the understanding that you might need to explain it someday. That doesn’t mean to not do something, but it does mean to accept that it might become known. I’ve posted a video clip online of someone talking to me over twenty years ago. Now, that clip was trimmed so that her identity was not in any way revealed, and there wasn’t anything in the video that was in any way bad, but… had there been, and had I been unscrupulous, she could have had video from 1988 shown online, and she would never have expected that. Likewise, especially now, things you thought would always be secret… aren’t necessarily always going to be.

      2. Personally I feel that in a long-term, serious relationship, past sexual escapades such as this or being a stripper, or a whole host of other things, should be shared because the right person isn’t going to judge you for any of that and I feel that there is no point in hiding any of that.

    2. WatersEdge says:

      I say this with the greatest respect and appreciation for the LW… I don’t think she’s the kind of woman who’s keeping herself pure for her husband, or thinking of her future husband when she makes present-day decisions. She’ll probably end up with the kind of man who spent some time “living for today” as well.

    3. If nothing else, you might have to explain/lie about where oodles and oodles of expensive gifts came from….

  15. sobriquet says:

    Would anyone like to purchase any of my used panties? I could really use the cash right now! ha

    Seriously, though, this setup doesn’t sound very strange to me. In fact, the only thing strange is the fact that you actually discussed the status of your relationship. I doubt most sugar daddy relationships involve that conversation. I say go for it as long as it feels right (and of course think about the potential negative implications this could have on your life).

    Just don’t feel obligated to stick around if things change!

  16. Don’t get your panties in a twist over this. The whole thing will last a year, he’ll get bored and find a new sugar baby. As soon as the thrill wears off, they are gone. Seen ’em come, seen ’em go more times than I can count.

  17. hoyporridge says:

    I agree with sobriquet when she says that she doubts any sugar daddy relationships involve this conversation – it’s so blatant that the situation has now been reduced to nothing short of sex working. Don’t kid yourself, this is not going to work in the way that you think it will – the first time you do it, you will probably feel a little disturbed and if you don’t then you probably should be concerned

    This man’s intentions were laid bare when he offered you cash for your underwear – it’s not about making you feel good, it’s about buying something from you. A sugar daddy may have bought you a gorgeous selection to wear and suggested you change into a new set after each date, quietly taking your used pair away with him – not perverted, just kinky…

    Something that is so blatant is about as unsexy as you can get. Be wary.

    1. theattack says:

      I don’t know. I think I would rather have this conversation up front and then make the exchanges later than to be creeped the F out when he asks me to give him my panties at random. I think the conversation here is healthy. May not be typical, but you can never have too much communication about what the state of your complicated relationship is.

  18. JennyTalia says:

    Ok the panties thing is weird, I don’t want anything to do with my own used panties nevermind anyone else’s. But shit if someone wanted to buy me things and all I had to do was answer booty calls (which I already said I’d do for free) – call me a prostitute but that sounds like win-win to me!

  19. fast eddie says:

    I don’t see anything “wrong” with an arrangement like this but if you submit to his request he’ll have the trump card when, not if, it come down to something he wants to do but you really don’t. It boils down to how much you value your independence. On the other hand if the price is right and your not in physical or emotional danger, why not. I’ve known some couples that were decades and mindsets apart that had successful relationships.

  20. spaceboy761 says:

    I just think that this guy is your garden variety perv. The panties thing isn’t completely unheard of, but still pretty far on the kink spectrum as far as the general populus is concerned. He also gets off on the whole objects-for-sex power pay, which isn’t entirely uncommon either. If you’re both cool with it, knock yourselves out and try not to get herpes.

    Everybody’s partner has kinks. I like to tittybang, this guy likes his stuff. Whatevs.

  21. *sigh*

    You don’t mention your age. This would have helped a lot.

    I can tell you from experience, having a “Sugar Daddy” does you no favors. In fact, it does you a disservice. You are putting a price on your affections and sexuality. Do you really want to have to explain later in life to your children that the diamond earrings you are wearing were a gift from a guy you gave a blow job to?

    A “sugar daddy” gets off on being able to pay for what he wants. They are controlling, manipulative and abusive. They may not seem like it at first. Sure, they act sweet and caring. They like to throw money around. But, soon they tell you that they want to experiment a bit in the bedroom. Then it gets a little abusive during sex. Pretty soon, he acts like he owns you. Hell, you sell your sex to him, so in a way, yes, he does own you. You are just a filly in his stable.

    Walk away from this. Now. And make sure to check that all of your panties are still there. He may have pocketed a pair without you knowing it.

    1. Why couldn’t you just tell your child the earnings were a gift from an old friend? Isn’t that just as accurate without being vulgar?

      I further think it’s a bit over the top to claim that a man who likes to buy a woman gifts but doesn’t really want to date her is abusive – I’ve had an experience like that with a man and he was truly one of the most lovely people I’ve ever known and I don’t regret the time I spent with him even one little bit.

    2. uh…yeh. and you can tell the kids that the diamond ring they got is from the guy you give blow jobs to. because that will be your husband.

  22. Chicago_Dan says:

    This got me thinking of the long-term;
    1. What happens if one should fall for the other beyond ordinary control? How do you justify the monetary exchange?
    2. What do you stand to gain from this experience and how will it potentially impact your view on sex with a future partner (serious or NSA) when the monetary value is absent?

    Of course, as an adult in a free country do as you please but be honest with yourself about the WIFFMs of this “deal”. If you are satisfied with the answers you provide and are content, please send an update in the future on how your “predicament”.

  23. Skyblossom says:

    This guy tells you he doesn’t have time for a relationship so wants a sugar daddy relationship but yet he has the time to pursue you and does have the time for a sugar daddy relationship. I don’t think he’s being honest with you since his actions don’t match his words and that means be very wary. People lie when they think the truth won’t get them what they want. He seems to know you well enough to tell you what you would like to hear and to offer you a relationship that excites you. This means he knows you well enough to manipulate you.

    Do you know about any of his former sugar babies? How did he treat them? Are they okay? Don’t assume you’re the first because this sounds well thought out and planned.

    At the very least don’t leave the country with him because it would be very easy for him to take your passport and then you could find yourself trapped in a terrible situation.

    Consider yourself more valuable than the gifts he could give you and pass this one up.

  24. yip. I’d say don’t trust him.He’s going to keep pushing boundaries until he finds something you DON”T want to do-and then however you deal with the situation you are going to come out feeling nasty.
    It’s simple- if you’re not hung up on this guy, then find someone else who doesn’t put you on the spot like this. And if you are hung up on this guy—then run like hell, sister, because his dark underbelly is very dark indeed.

  25. Where were all the sugar daddys that wanted to give gifts for sex when I wanted one? Heck, when I used to get horny, I’d give it away for free for one night, this seems a much better equation. I’m the type that can have sex without getting attached, however, if you are not, don’t bother with this relationship.

  26. lets_be_honest says:

    Um helloooo, I am the only grown-up on here watching the new 90210?

    1. Addie Pray says:

      NO! HAHAHAHAH. I know what you’re talkin’ ’bout! (Now I’m ashamed.)

      1. lets_be_honest says:

        Hahaha! OK, good, I’m not the only one. Hey, its better than the Kardashians, right?

      2. Addie Pray says:

        YES – because at least that trainwreck is fiction. But the Kardashians? Real life trash. Don’t get me wrong, I love it all…

      3. lets_be_honest says:

        Yea, exactly. I say that as though I don’t watch it.

      4. Addie Pray says:

        Yea, I don’t DVR it either. And I don’t secretly hope the two teenage girls (whose names I don’t totally know but am not not sharing that so I’ll look less into the show than I really am) start acting out and then get their own show to showcase their brattiness so I can start not watching that Kardashian spin off! I don’t do those things. Did you catch that?

  27. AndreaMarie says:

    Listen you are both consenting adults and if you are comfortable with meaning no more than sex to this guy then go for it. If it’s something fun and exciting for a bit, plus some added perks, then why not.

    But there are 3 negative issues that could arise…

    1. Obligation. What happens when you have had enough the arrangement? When you have found a real boyfriend and can no longer fit sugar daddy in your life? What if he pulls the whole “well I just bought you a new car you owe me sex for another year”. I cn’t even begin to get into the different scenarios with this…but you get the drift.

    2. Don’t let this arrangement interfer with your ability to find a real partner. I was once involved in an affair and though I was comfortable with it at the time and knew what it was I still was caught up in the excitment and spent far too much time texting with my lover and not investing enough time texting my real potential boyfriends.

    3. He is 99.99% likely married.

  28. So, this whole prostitution thing got me thinking . . .

    Let’s say you’re friends with someone and one day, you decide to be sex buddies. You go out a couple times a month. Have dinner. Hang out. Go home. Have sex. The sex is pretty good and you both have a lot of fun. Now to the prostitution part . . . he always pays for dinner. Girl might offer, but still pays. Is that like prostitution? I don’t think so, but under what some are saying, it kind of sounds like it. Also, would it make a difference if this man was the same age or a little older?

    1. Addie Pray says:

      This sounds just like my 8 month non-relationship with my neighbor, except we were never friendsa and we never went out and the one time we did, I paid. Fuck, I paid for sex. Ok, maybe it’s different.

  29. theattack says:

    I disagree with many commentors that the LW would have an obligation to the sugar daddy. It really depends on what their arrangement is. If he’s buying her small gifts for each occasion, then he’s paying for the sex they’ve already had. If he buys her a car and says it’s a down payment on future sex, that’s different. She has no obligation to him if they take it lay by lay.

    I say go for it. When I was single, I would have loved to be able to satisfy my demanding needs for sex and simultaneously get some nice earrings. It’s win-win for everyone as long as you plan correctly.

    1. what I don’t get is even if he buys her a car and says its a down payment on future sex, how exactly is she going to be forced to “pay up” besides him raping her? Like this isn’t a set legal agreement she’s entering into. She can walk away at any time unless she becomes dependent upon him for something like rent.

      1. theattack says:

        That’s a really good point. Even if they made it into a contract it probably wouldn’t be enforceable because it’s so close to being illegal. If he’s casually giving her gifts, that’s one thing. If it’s an official exchange, it’s probably going to be considered prostitution.

        She just has to be smart on what she spends this money on. Is it something extra like clothes/ jewelry or is she factoring it in to what she considers her income?

  30. bittergaymark says:

    Eh, many of you seem to find red flags where none exist. Seriously. Some guys like to spend money on their lovers. Lots and lots of money… Some like to be FORCED to do so it seems as the money aspect is something that truly helps get them off.

    I say, go for it.

    No, seriously. Go for it. Ironically, when I was younger and thus infinitely more desirable I had a slightly older guy who desperately wanted to do this with me. He wanted to shower me with gifts and trips and — like an idiot! — it really made me uncomfortable. The real irony is that now, when I could actually REALLY use lavish gifts of money and fabulous trips, nobody is offering. Oh, well. Such is life. Seriously, if it doesn’t phase you — go for it. Enjoy the ride.

    1. theattack says:

      Seriously. This is probably the first time I’ve ever agreed with you. People on DW are so quick to say that a relationship (or any sort of arrangement) is bad or harmful or creepy or just not a good fit. But saying no to too many things means that you’ll be alone forever, and you’ll be bored while doing it. If the LW gets sick of this, she can stop. No big deal.

  31. I had plenty of NSA encounters in my time. If I could go back and get paid in money and gifts for them, I would.

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