i think its more that your afraid to take it in the glory hole because the media has portrayed anal sex to be "bad", especially when the one with a Y chromosome is on the receiving end. in my opinion, just keep your mind open to these things. you never know, the shemale of your dreams could be waiting around the corner in your life and she might prefer to be a top than a bottom, or she might like to be versatile and likes to both give AND receive.
just remember to use lube if/when you decide to try it. take it like a man