I'm a 53-year-old straight male in a long term "exclusive-ish" committed relationship. I say "exclusive-ish" because a few times a year we'll have a third join us for a 3way. So far, the third has always been male, but my better half is open to the idea of that third being female so long as she isn't the one doing the asking. As you can imagine, the possibilities of a willing woman falling into our lap is about as likely as winning the lottery. Consequently, the idea is just an unrealized fantasy of mine. However, this weekend I got a strong vibe that this younger woman was flirting with us. She was probably at the youngest 25 and at the oldest 32.

This isn't a fantasy I'm obsessed with, so I don't think I'm projecting or imagining things through a distorted lens, but I also don't want to make an ass out of myself and come off as the old creepy guy either. So I'll lay out what happened as briefly as possible and maybe you can tell me if I need to forget about it all or risk looking like a fool and try making some inroads should I encounter her again?

The rest of DADDY's long, long letter—and my short, short response—after the jump...

We were at the local casino we frequent a few times a month and this woman sits next to me at a slot machine and starts chatting me up like were old friends. My wife is to my left, she is to my right and standing behind her is her boyfriend or husband, I don't know which. I know I've never seen this woman before in my life and she is saying things like, "Oh, we see you guys here all the time," and "You guys are so nice", blah, blah, blah, just general conversation, but she's leaning in to me and making long eye contact.

She seems perfectly sober by the way.

She sat there next to me for about an hour or so, and I really didn't think anything about her as being anything other than just a really friendly person, until later. Her husband or boyfriend seemed like the shy, quiet type and he didn't say anything at all, nor did he seem to be bothered by her overt friendliness to me either. He just stood behind her the whole time.

She got up and they left and after another hour or so we decided to head home. Had I not seen her again I probably would have forgotten her altogether. We were standing in line to cash in our ticket and she comes up and grabs my arm or taps my shoulder, and is standing close asking if we won and telling me about her bad luck, but she's smiling and making serious eye contact. The boyfriend or husband was standing several feet away and again with no input. Then, as she was walking away she stops and turns around and waves again.

I don't know, as I type this all sounds completely innocent, but I don't usually mess up signals from people either. Just to add a few more details: We are a fairly attractive couple for 53 and 48 years old, both in good shape, fit and all. The younger woman had a very pretty face, but she was not in shape and her boyfriend or husband was average looking. I'd guess they were both 28ish.

So Dan, am I seeing this event through the rose colored glasses of a 53-year-old man who is thinking with his cock and not his brain? Do I need to just forget the whole thing, or should I take a chance and try to inject the fact that we might be game for some fun with her, or them for that matter, if we run into them again? She did say, "We see you guys all the time," so I guess we'll see them again at our casino.

Divided About Doing Dishy Youngster

They were either swingers looking for a couple to take upstairs (10% chance), DADDY, or that youngish lady is a sex worker (90% chance) and that mysterious youngish guy was her protection, her boyfriend, her pimp, or all of the above.