I am really thinking about finding a provider who will put on a strap on and anal me.  Never have done it before, but have thought about it.

Advice?

My fiancee and i do this every so often and he LOVES it! I have to admit- it really satisfies some desires of mine as well =0). I have only had one client ever ask me to do this- my very first- go figure- lol. But i think it's wonderful that any man should become so comfortable with himself to pursue such a taboo but Extremely pleasurable experience. My advice would be to find a provider(eh-hem) that likes that kind of thing, and bring your own toys. There are many different shapes and sizes. This is a Big consideration- so choose carefully. (and if you can, get one that will stimulate her as well)
From there- just relax and enjoy!

I've dabbled in D/s play with Pro-Dommes and have experienced strap-on play/training.  My advice: Start small, use plenty of lube, and if it hurts - stop because anal play shouldn't hurt.  Good luck and have fun.