Playing With Fire, Or When Worlds Collide

Do you keep your hobby life completely isolated from your personal life or do you allow a little crossover to happen?

Years ago, when I was relatively new to the hobby and boards like this had chatrooms, I was chatting with a lady I was interested in seeing. She had mentioned on a post that she was moving her shared incall location to her own private one and was looking for help with the move. I thought this would be a good way to meet someone and the idea did cross my mind that we might work a little trade of services or at least I might curry some special favour. Maybe not free time but perhaps some extra time. Regardless, it wasn't going to be a big commitment. So I meet her the next day and we get to chatting, and she's like "you look familiar". I say maybe she was out at karaoke night or something, and I always go out singing, that's where I get the "do I know you" from a lot. She says something about her kids and her one son playing football. I'm like "my son plays football" and we start comparing notes. She says a longtime friend of hers name and I say "he coached my son in the summer camp, he's not his coach now, he coaches the next age group up, but he's part of our overall team". So it turns out that's where I was familiar to her from, the football games our kids were playing. The disappointing part of this was she decided because of our personal connection she said she couldn't see me as a client. Personally, I felt like what difference does it make now, we both know each other's secret, it's not an affair, whether we fuck or not isn't going to change things at the football field. We did end up becoming pretty decent friends for the next several years, usually involving the kids sports, she got me involved in a charity one of the coaches had going, and I went and hung out at her incall with her and talked shop when she had some downtime. She gave me lots of advice on the industry and I was a good venting outlet for her. We met each other's spouses at games although we never hung out socially. She did make good on my labour for helping her move, although not with her. She had a friend at one of the massage places she used to work at that owed her a favour so she sent me to see her for a 45 minute freebie. We were good friends for several years until she moved away 5 or so years ago.

The main reason I started this thread though, was more about last night and yes, karaoke was involved. Years ago we had an industry meet and greet party and there was karaoke at this party. I've loved to sing for 35 or so years and some of the people at this event were pretty good. One of the new ladies on the scene sang that night and not only was she hot but she could belt it out. I started seeing her pretty regularly and naturally, our shared singing hobby came up. I mentioned where I sang at and suggested she come by some time. She never did, the most social interaction she was willing to do was at the stirp club that a lot of us hung out at. So anyway, life does what it does and I went years without seeing her. I bump into her about a year ago at a local store, she didn't recognize me, I didn't say anything. But, I had followed her instagram all those years ago (with her blessing), and I pulled it up and sent her a message. She hadn't updated it in years so I didn't even know if she would see the message. She did and replied to me a couple hours later. We exchanged a few pleasantries and I gave her my number. She wasn't working but she said "do you ever really walk away from this business?" So, several months go by and I get a random "hello" text. Spam. A day later a "hey". Spams don't usually send a followup unless you answer but I ignore. Happen to go on IG and theres a DM from her saying "That's me texting you lol". So I reply and she asks if I have time to chat on the phone. I say give me 10 minutes, and I head out to the car for a drive away from prying ears. We talked for almost 2 hours about life and kids and she says she hasn't been in the business for so long now but she's planning to come back and wanted some advice. It felt really great to connect with her again.

So, the karaoke part comes in. That day we talked was a Thursday and it's karaoke night. I'm at my usual karaoke hangout, and I'm thinking about this conversation that afternoon and we didn't even mention karaoke. I send her a selfie of me with the karaoke stage behind me and ask if she still sings. She replies with a selfie of her at another karaoke bar lol. My instinct was to head there and see her. I fought that urge. So anyway, we keep a text string going over the next couple weeks until she gets herself set back up working and I start seeing her again. We have a great time in the now, and the catching up of old times. A couple weeks goes by, I'm seeing her on a Wednesday night and I know the next night is both of our regular karaoke nights. Problem is, the place I go to had cancelled that week due to a private event. So I ask her, I don't want to randomly show up at the bar she goes to, but would she be upset if I went there. And I say "you don't have to acknowledge me in any way if you don't want to, I'll follow your lead, but it would be cool to hear you sing again, and I don't really have anywhere else to go anyway". She's all casual "yeah, no problem, sometimes I'm with friends, sometimes I'm alone, maybe I'll speak to you". I was kind of hoping some of the people I know from the other place would make the trek to this place but no one did. I saw her there, we chatted for a few minutes early on, then we carried on as any other night would go.

Over the next few months, we saw each more and more socially. Sometimes we would meet up at a karaoke night, sometimes we went out for food after a session. We've become pretty good friends and if I was forced to choose, I think I would rather be her friend than her client at this point. But I'm hoping I don't have to make that choice either because I really like having sex with her too lol. The reason I titled this the way I did was in a couple of occasions over the last few months, she has been in the same bar as me and my wife have been. One of them, me and her didn't interact at all, the other, she walked by our table and exchanged "hi's" as people who sort of know each other would do. Yesterday I told her that my parents were visiting from another province and my mom wanted to hear me sing, which she hasn't in years, and that we were going to a bar that she also goes to, and that my wife was likely coming along. We talked about how we should act with each other. She said "we've been seen by enough people that we know that it would probably be noticed if you are with your wife, and me and you avoid each other, so maybe we should just act like the friends we say we are". Maybe I give people too much credit, but I know if I saw "Mike", who I've known him and his wife for 20+ years, and Mike is with another woman, and then a week later I see Mike and his wife together and this other woman is in the same bar and her and Mike aren't talking, I would be suspicious. Whereas I would be less suspicious if this woman was talking to Mike and his wife. So we decided to lean into it a bit. She came in a while after we had been there, said her hello's to a few people and stopped at our table. Said hi to my wife like she already knew her, asked me if I would sing that song with her that she's working on that needs a male part, and then carried on like normal bar friends would do. The kicker was when I was singing my last song "Pinch Me" by the Barenaked Ladies, and I look over and there they are chatting. I'm expecting to get in the car later and have my wife say "just how stupid do you think I am?" lol. Fortunately, this girl is way out of my league, so even if I said to my wife "You know that girl I sang with, I've been sleeping with her for the last 6 months", she would say "yeah, sure you have, if she'll fuck you, you go for it" lol.