I suspect for guys the older you get the more acceptable the idea becomes. When you're in school all you're concerned about is not appearing gay to your macho buddies.
Once you hit 30 you realize it's your own sexuality and enjoyment that matters. What somebody else thinks about it is their problem. Some uptight guys think giving anal to a women means you're closet gay.
(no, I have never taken a strapon for the pansies who are wondering)
P.S. Since I'm probably the biggest mofo on this thread I'll say it. With the right person I probably would try it SO THERE!