I'd say getting in touch with others in the community is pretty vital, both for meeting but also for safety. These are the people who are going to know if a guy is trouble or not. As far as whipping specifically, I find that it is good to find people into impact play and start off with lighter stuff (spanking, flogging, crop) and building the trust between you and the other guy. You're going to have a MUCH better experience if you are comfortable and fully trust the guy you're with.

Plugs and dildos are what I've been using and it takes a while but does the trick if you're patient and don't rush your body. You also have to keep up with it as I recently went from taking fairly good sized plugs no problem in November to tight as a virgin again this past weekend thanks to the holidays keeping me too busy and tired to play with my ass much. :cry2: