Escort to sugar baby

Curious if anyone has come across a similar situation before (I feel like I’ve seen it in the past but can’t find it).

I recently met a very low-volume lady with a day job, who is thinking to leave this biz, and she asked if I’d consider a sugar relationship with meets several times a month. I can afford the once a month sessions I enjoy now, but I don’t repeat very often so I declined initially because of the cost.

She’s in her 20s and I’m in my fifties and apparently I give off a “safe” vibe from what I’ve heard from a few of the ladies. Im quite attracted to her physically. We had a nice connection and, unusually for me, texted on and off and met socially once off the clock. She persisted in asking a few times over a few months and offered to negotiate an arrangement. I haven’t pursued that for a couple of reasons.

Number one is cost. I’d be squeezed for sure although I didn’t explore what she was willing to negotiate (i suspect more time for the same money but not 100% sure). I have a partner so I’m careful to squirrel my money away in inconspicuous amounts over time.
Number two is feelings. I like connecting so I do enjoy building a bit of connection in sessions…but I don’t repeat often because I worry about catching feelings. This lady brings out my protective and mentoring side which I feel could lead to too much connection lol

I’d prefer to continue with sessions when I want (pay per meet), but if she made a really good offer, I’d be tempted to try it for a bit to see how it worked out.

It’s a novel situation for me. Anyone experienced anything like this?

MauiMan said:

I did it once. It became an exclusive thing, she stopped taking other clients, I paid her rent and some other bills. we had dinner together several times a week, not always involving intimacy, but more like a girlfriend without the labels. I loved it, but it wasn't financially sustainable. Feelings definitely happened on both sides. Once a week at 400 isn't the same thing as 2500 or 3000 a month. Great run though, don't regret it, but not sure I'd go there again. She ended up with a much richer guy who could afford all of her needs, plus travel and other things I couldn't manage.

If you do it, you need good ground rules, open communications.

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Thanks for sharing your experience. It sounds like you had great time while it lasted. I think that’s ultimately what she would like; one guy to cover everything in an exclusive situation. Feelings or not, at the end of the day, it’s a business arrangement, ideally mutually beneficial - but feelings still happen.

Just writing it down was enough to clear my head. But I’m still curious if others have had some experiences like that, but having actually gone through with the arrangement