How to Speak Up in Your May-December Relationship

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.