QUESTION: I’ve been dating my sugar daddy for about six months. We have a pretty good sex life, but I want to introduce role playing in the bedroom. What’s the best way to go about it?
CHELSEA SAYS: Ask him what he would be comfortable with because, if it’s your thing and not his, you need to invite him into it slowly. Don’t just show up in costume—it might throw off his game. If he’s up for role playing, ease into it. Good sex starts long before you ever reach the bedroom—it’s just as much about the anticipation and the expectation. Build the suspense by sending him a picture of your outfit and talking about the scenario. Don’t go too extreme with your character—pick a scenario that’s natural, but naughty—think teacher/student or nurse/patient. Also, make sure he sees how much you enjoy it because, if your sugar daddy sees that you’re pleased, then he’ll be pleased too.
TRENT SAYS: Your sugar daddy isn’t into role playing? Interesting. On one hand, if he’s not into it, then he’s not into it. But on the other hand, most men will come around on some level. If you sense that he’s apprehensive, then start slowly and think long-term. When you’re having dinner, ask him if he has any fantasies, like sleeping with Princess Leia (he probably has; what guy hasn’t?) You can try something non-aggressive, like dressing up as the strict librarian. Or, plan a themed date night at home. Dress up any way you like, and have at it.
QUESTION: My older sugar daddy is pretty liberal with his money. We’re planning to go away together in a couple weeks and he gave me his credit card to do a little shopping. But I think I went a little overboard and spent way too much money. How do I break the news to him without him flipping out on me?
CHELSEA SAYS: As long as part of what you bought includes something for him, like lingerie, I don’t see how he could have a problem, since he’s liberal with his money. If you’re really having regrets about how much of his money you spent, then just return the stuff that you don’t really need. If everything you bought is a necessity, then he might understand. But if it’s frivolous spending just because you had the means to do so, it might give him the wrong impression that you’re only with him for his money. If you are just with him for his money, then that’s a whole other issue.
TRENT SAYS: I’m not so sure there’s any news to break to him. I’m guessing that he gave you a credit card with some sort of spending limit. And that limit is your monthly limit, or at least it is until he pays it off, which will free up space for more shoes, lingerie, and whatever else you’re spending his money on. At the same time, the fact that you’re asking this question means some things have not been adequately communicated between the two of you. I suggest telling him how much you spent and if he asks you to return some things (he won’t), then do so. No short-term purchase is so monumental that it should jeopardize your relationship with him in the long run. Then, after everything’s on the table, ask him what the parameters are on the credit card going forward.