What does anal really even feel like?

Give yourself and enema. It will help your sphincter dialate and it will clean you out, so you won't have to worry about any messiness then go easy, liberal amounts of a safe lube. I highly recommend you explore this by yourself a couple of times - it will make for a much more pleasurable experience. Word of caution, enemas do have the potential to upset the balance of natural occuring flora and fauna in your digestive system, so don't over do it, or do it too frequently, and make damn sure you don't use water that is too hot or too cold.

(sonuvabitch this thread is old, I hate when I do that)

 

Yes! I am too! And I LOVE anal!
The act of anal isn't horrible. It's all about your mental attitude. -.-