We had to do it in public since neither of us had a house to ourselves and we really wanted to start wedgieing each other ASAP so we just risked it and did the wedgies in a wooded area, it was kind of annoying since it meant we couldn't do the wedgies naked but we were both fine with that.
The first thing I realised was that wedgies are A LOT more painful when someone else gives them to you then when you give them to yourself, so bear that in mind.
The best way to arrange a meet up is search around on wedgie buddies for people near you, and message them.