My wife grew up a a good catholic school girl, and has always acted very conservative and shy about her physical appearance. I have dared her off and on Over the past few years to send me some pictures from her phone when we were aprt. Too my surprise when my phone beeped and these beauties were on my phone to view. She has a gorgeous body and doesnt think so. Maybe a little prodding and some kind comments from others might help her "let loose" and the real truth or dare game can begin!
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The MILFs are single, married but looking, or in open relationships and most have busy lives being moms and working. So discretion is preferred and they are usually quick to act without much in the way of gamesmanship.