It could work. All depends on how you ask I would say. It would be real easy to come off sounding creepy. Much depends upon how you yourself view this 'hobby' and also how you carry yourself.
In the Eastern European countries this sort of thing is relatively common. A young woman in, for example Latvia, would have at least a couple of friends who has at some time spent time with a guy for cash. In other words, there is a precedent.
In Canada (at least when I left-3 yrs ago) I wonder if this sort of thing is at all common. And if it is common, I wonder if it ever gets talked about. There is a such a huge stigma attached to prostitution in North America.
Here in Berlin there is a club called 'La Folie'. It is a small bar where you can go and meet young women who will go in the back (where they have small rooms available) and have sex for a fee. Many of the girls that work there (though not all) are part-timers who drop by for a few hours, after working their day jobs, to make extra cash. It is a bit like a smaller version of the FKK clubs in the rest of Germany.
So here there is a precedent for this sort of thing and, had I the cash, and perhaps a bit better German language skills, I would be tempted to try your suggestion here. Though for some reason many of the supermarket cashiers here are old and frumpy....
I would be careful, for the reasons others here have suggested, of trying this in Canada.
YL
