Twenty-six-year-old bi male here. Quick question: How bad would it be for me to hook up with the former stepdad of a woman (my age) I briefly dated? She and I did have sex, but things only lasted a few weeks and never got serious. We parted amicably last month.

I met her former stepdad once, when she and I went to lunch with him. He's a nice guy, good conversationalist—and totally the sort of "daddy" I have been fantasizing about since I was a teenager. Handsome, fit, masculine, friendly but authoritative, etc. He's been divorced from her mother for five years and is currently single. No idea if he's out or not. But he apparently was checking Scruff while I was doing the same in the restroom during our lunch, and he saw my profile and recognized me. (Not hard to do—my face isn't on there, but the tattoos on my arms are quite distinctive and I was wearing a T-shirt.)

He messaged me the other day, was up front about who he was, clarified that he was pretty sure Former Stepdaughter and I were no longer an item (but said to correct him if he was mistaken), told me he'd been instantly attracted to me at lunch, and then proceeded to describe in graphic detail what he wanted to do with me. I was friendly in my response but told him I needed to think on it. Dan. I have already jerked off seven times reading and rereading his message to me. I want to be naked and in this guy's bed yesterday. Or wearing high heels and stockings while bent over his sofa, to give you some idea of what he described.

I'm pretty confident Former Stepdaughter and I aren't getting back together, and I don't see her regularly on a social basis (though I'll probably run into her at some point). We live in a big city, so it's not super likely she would see me and him out together. I mean, I don't even think it's likely he and I would be anywhere together that wasn't his house (again, naked or mostly naked). I still just feel kinda weird about it, because I slept with his sort-of-daughter.

But she's not related to him by blood, right? But does that really matter? But seriously, Dan, this feels like I would be passing up dream sex and when I ask myself if I'd regret not hooking up with him, the answer that comes back is a resounding YES. On the other hand, I can't come up with any rationale for a solid no—I think it's just, like "phantom" guilt because of the weird family connection. I strongly suspect a few minutes with his beautiful cock (Dan, he has a BEAUTIFUL cock) would eradicate that pretty quickly. Do I have your blessing to find out?

Lusting After Delicious Wolf And Need To Sate Desire — Although, Daughter

First, you have my blessing. Enjoy and send pics.

Now for my thinking: You're no longer seeing this woman—a woman whose ex-stepfather turned out to be a hot and apparently bi daddy—and you're highly unlikely to wind up dating this guy, which would require you to go public/get found out/squick her out. Unless Cupid is in a perverse mood, LADWANTSDAD, all we're talking about here is one or two or three dozen scorching hot bent-over-the-sofa-in-heels-and-stockings sessions.

Now your route into this man's pants—the chain of events that led to you to his library sofa—did run through his former stepdaughter, LADWANTSDAD, and that's wrong. But it's a particular kind of wrong. It's a naughty wrong, a dirty wrong, but it's a wrong that doesn't actually wrong anyone. It's the kind of wrong that can (and will) be safely and consensually enjoyed by the wrongdoers without harming anyone else. It's sexy wrong.

So long as the woman you dated briefly never finds out about it.

But even if she were to find out—because it was too hot a story to keep to yourself and you bragged to someone who blabbed to her or because she happens to be a reader of mine—what harm was done? She most likely wouldn't be happy about it, she might even be grossed out, but the worst she would have to endure are some unwelcome mental images. This hookup would neither break her leg nor pick her pocket, as the saying goes.

Now it would be different if this man were still her stepfather, of course, because finding out would create a very serious psychological burden for her: the burden of knowing her stepfather was cheating on mother. That her stepfather cheated with someone she knew, liked, and dated herself—someone she introduced to her stepfather—would add insult to injury and she would be rightly furious with you for putting her an excruciating position.

But he's not her stepfather and you aren't her boyfriend and you're not gonna become his boyfriend and chances are good-to-great that that she'll never find out and even if she does, well, she'll get over it. But I'll be interested to see what others have to say in the comments thread—it's possible I'm biased in favor of hot daddies bending hot bi boys in heels and stockings over the ends of their library sofas.

Let's just say that I'm not sure I trust my own judgment on this, as an early viewing of Rocky Horror Picture Show left me with a rather pronounced pro-hot-bi-guys-in-stockings bias. I mean, Barry Bostwick...

Sigh.

Anyway, Sloggers, what say you?

UPDATE: My bias blinded me to this aspect of the situation, deftly unpacked here by Callie...

Yeah my first thought was: step dad may not be married to her mother anymore, but they've been divorced for 5 years and she's still introducing him to guys she dates. That means he is a father figure in her life at worst, a trusted friend at best. Either way it sounds like her relationship with her step-dad is still very much familial. If she grew up with him it doesn't matter that he is no longer married to her mother - he is a father figure for her. If she does think of him as a father figure and she were to find out, I'm sure it would be upsetting to say the least. It could even potentially irrevocably damage her relationship with her step dad. None of this is really on LW though...