Q: I’m a 40-year-old bi man. I’ve been with my 33-year-old bi wife for three years and married for one. When we first met, she made it clear that she was in a long-term (more than three years) “Daddy” relationship with an older man. I figured out six months later that her “Daddy” was her boss and business partner. He is married, and his wife does not know. I struggled with their relationship, since I identify as open but not poly. Eight months later, she ended things with him because it was “logically right” for us (her words). But she cheated with him four times over the course of two years. In all other aspects, our relationship is the greatest one I’ve ever had. I do not doubt her love for me. My wife has met her biological father only a couple of times and her stepfather died when she was 16 — the same year she went to work for her “Daddy.” Their non-work relationship started 10 years later, when she was 26. It’s a complex relationship, and he is not going anywhere, as they now own a business together. While I don’t think cheating has to be a relationship-ender, dishonesty always has been for me. The final complication: I have a cuckold fetish. I believe it might be possible to meet everyone’s needs, so long as everyone is honest. I will admit that, in the heat of passion, my wife and I have talked about her having “two daddies.” Do I consider allowing this, so long as everyone is honest? Is mixing business and personal matters going to blow up in our faces? Do I ignore the part of my brain that wants this guy’s wife to know? — Distressed About Deceitful Dynamics Involving Entangled Spouse
You don’t need my permission to consider this arrangement — allowing the wife to have two daddies — because you’re clearly already considering it. (You’ve moved on to the bargaining and/or writing-letters-to-sex-advice-columnists stage of consideration, the final stage before acceptance.) What you want, DADDIES, is my permission to do this, not just to think about it. Permission granted. Could it all come to shit? Anything and everything could come to shit. But your wife has been fucking this guy the entire time you’ve been together, and you nevertheless regard this relationship as the greatest one you’ve ever had. It stands to reason that if things were great when she was honest with you about fucking her boss (at the start) and remained great despite being dishonest with you about fucking her boss (the last two years), you three are in a good position to make this work now that everything is out in the open.
As for your other concerns: Most of the poly people I know started out as either monogamous or “open but not poly” (people evolve), we find out about secret workplace romances only when they blow up (skewed samples make for skewed perceptions), and you need more info about the other man’s wife before you issue an ultimatum or pick up the phone yourself (their marriage could be loving but companionate, he could be staying in a loveless marriage for good reasons, they could have agreed to a DADT arrangement regarding affairs). But again, DADDIES, you’re asking if something that seems to be working in practice might actually work in practice. And I’m thinking, yeah, it probably could.
Q: I have a sugar baby who is a mature post-op trans woman. She is very attractive but also very high maintenance. (She has OCD.) I pay her $300 per anal sex event; I help with bills, food, etc.; and I spend every weekend with her. I probably spend $15,000 a year on her. I’m happy most of the time (the sex is great), but does this arrangement sound fair? — Daddy Asking Dan
Divide the money you’re spending annually ($15,000) by the number of weeks in the year (52), DAD, and your anal-sex-event-packed weekends are only costing you $288.46 a pop. Seeing as most sex workers charge 10 to 20 times as much for a full weekend, I’d say you aren’t spending too much. (If this arrangement is unfair to anyone, DAD, it’s unfair to your sugar baby.) Now, if you’re only pulling in 30K a year, spending half your pre-tax wages on a sugar baby is unsustainable. But if that 15K represents a small percentage of your annual income, DAD, you should give your sugar baby a raise.