Been there! done that before I was married. Ex-girlfriend was really into it. As long as you take it really slow, lots of lube, and plenty of finger stimulation/penetration before you try with your penis, it wont be so bad. Yes I did enjoy doing it. But I dont really miss it either. My sex life with the wife is more than fine, when we have it! Guys/gals who have never tried or failed, it is because the experience was rushed. at least in most cases I would expect. Not every womans body is built the same and it may not work for everybody. As far as receiving anal play, been there done that too! I didnt like the penetration at all but it was taboo enough to let it happen. Afterwards, we decided It was not for us. However stimulating the "taint" will stay on the list! I think if more men realized there is more fun getting there, than finishing the race, women would enjoy anal more often. I hope I have not offended anyone!