My most successful attempts at getting others to go nude with me has been at a clothing-optional sauna in Maine. The ambience there is so relaxed regarding nudity that the women I've taken have almost all tried it very quickly. Usually before going, I tell them that it's clothing optional and that some nights a lot of people wear clothes and some nights almost no one does.
The choice is theirs. Since there is usually a pretty good mixed crowd, very few with a suit on, my friends have chosen to get naked, too. With one, this involved a discussion where we said that we didn't mind being nude in public, but felt weird about seeing each other and agreed to just not look at each other.
One other experience involved the woman who is now my girlfriend. We had been emailing back and forth as she planned a trip. Someone on the Campus-Nude listserve sent a description of Harbin Springs and its URL.
I mentioned this to my friend, told her that it sounded interesting, didn't mention that it was c/o, but directed her to the website so she could find out on her own. She did, decided that it sounded interesting, stopped by and said she was the only solo woman there. She kept her sunglasses on for some amount of anonymity, but enjoyed her first public nude experience. Now that we're dating I'm looking forward to taking her to a nude beach.
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