I am a 46-year-old, self-made businessman from Texas who recently moved to Los Angeles about six years ago. Since moving here, I haven’t been able to find someone who really fulfills all my needs. Being single and living in Los Angeles has presented numerous opportunities and I’m having a hard time reaching for the right one.
I know that I have a lust and craving for women. Mainly women that are usually younger than I am. I frequently indulge in various strip clubs throughout the city, and I am not ashamed of this. I like to spoil the girls – so what? They give me the attention I need and I spoil them. Eight months ago, I met this stripping duo. They are sisters and they are lovely. Our patron/customer relationship has spilled over into casual meet-ups and dinners outside of the work environment. As we started to see more and more of each other, the gifts I would give both of them got more and more lavish and we eventually started a sexual relationship. Not all three of us at the same time, but with each sister separately. They both seem to be okay with this and it has been strictly sexual up to this point.
Thanksgiving comes around and they invited me over to their mother’s house for a nice dinner and I graciously accepted. The dinner was fantastic and the company was great. This is where it gets tricky: Mother and I hit it off. She doesn’t know that I have such a deep relationship with her daughters, but she took a liking to me and, to be honest, I took a liking to her as well. As time went on, we went out to dinner, saw more of each other and even became sexual with one another. I am having strong feelings for this woman and would like to continue seeing her as an actual relationship, but she doesn’t know I am still seeing her daughters and her daughters don’t know I am seeing their mom. Can I be a Stepdad, Boyfriend, Sugar Daddy and Lover all at the same time? Do I need to talk to everyone about this or do I keep it hidden? Please help.
Isn’t this nebulous, verging-on-incest-but-not-quite-there kind of thing what all straight men wish would happen to them, instead of in the porn they’re jerking off to? I don’t know; I’m not a man. Reverse the genders and your fantasy becomes one of those teachers who fucked her two students and, eventually, moved onto their dad. (Are you sure this didn’t happen in Florida? It feels very Florida.) I doubt yours is a situation that will end with a family orgy, everyone walking away totally unscathed. Then again, you may have just had Thanksgiving dinner with three unicorns.
Here are some scenarios I imagine playing out when you tell them:
1) The daughters are upset because they will no longer receive lavish gifts from you in exchange for sex and companionship. Though they are not in love with you, they like you, and although it may be strange that you have fallen for their mother, the loss of luxury will be the hardest hit. You stay away from the strip club. Get in good with Mom. Embrace a woman your own age. For the next decade, family holidays are fucking weird for at least one person there.
2) The daughters get upset because this means their mother stole their man. Did your dad ever steal your girlfriend? Imagine if he did. Only the heavily medicated can numb that kind of incestuous ego bruise. This scenario does not cause so much of a rift between the women and you, but between the women alone. (In fact, the daughters may even vie harder for your attention, like a Freud-sponsored race against the woman who gave birth to them.)
3) Mother and daughters are down. You live in a verging-on-incestuous-but-never-crossing-over polygamy and father many children. The gossip spreads like wildfire. (You aren’t ashamed of your unusual fortune.) Hollywood takes a whiff. TLC gives you a reality show.
Again, only in Florida could this end well. Why didn’t you move to Tampa Bay? You wouldn’t even need my help.
Look, this situation is full-blown mental. But you knew that, didn’t you? The biggest thing here is that you tell them before they tell one another. At some point, news will crawl from the very intimate grapevine that connects mother to daughters. (Its medical term is the “umbilical chord”.) I suggest you keep seeing mom. Pursue normalcy. Visit the strip club less and less. Instead of throwing fives and buying last season’s Micheal Kors bags for the daughters, use that money on Mom. Tell the girls that Santa has to head north and let them down easy. Your relationship with Mom started out of genuine interest, not monetary transactions. Now, I can’t say what Mom will think when you break the news to her. Maybe the daughters will agree to keep it hush-hush? (I’m basically lining out all the most desirable situations that don’t end with you stabbed in the scrotum with a dirty fork.)
I don’t know if you can be a stepdad, boyfriend, sugar daddy and lover all at the same time, but reality keeps nudging me and violently shaking his head. To be honest, I hope you can. I’m rooting for you. Maybe just because, like most little girls, I used to really like unicorns.
You made your bed; now stop fucking your new girlfriend’s kids in it. Good luck, Texas!
