Nearly the same post I made in Wolfies thread where you initially asked the question...
Yes, I have orgasmed during it and it wasn't quite as bad as Tom's experience, in fact it was wonderfully intense and pleasant!!
It is a different experience than clitoral or vaginal orgasms. When I am receiving anal I am more aware and alert to every movement of my Masters cock (or the toys he may be using on me) because of the obvious dangers if its not done right, as well as the fact that it is exquisitely more tight and stimulating so I can feel every little movement. These factors also come into the cumming experience, it’s more intense and powerful and it can easily become too much and very sensitive.
The most intense anal orgasms I have experienced is when I have been played with inside my pussy and ass at the same time and I vividly remember the first time Master and I did that, if I hadn't been tied over that chair and gagged I would have been jumping and screaming like a banshee it was so excruciatingly wonderful!!
In addition to the other post I will say that I have been practicing anal sex and play for as long as I have been having sex, although being careful not to over do it as I like my ass to be nice and tight, the point I am trying to make is I can take deeper and harder/faster anal now than I ever could and its during these times I feel myself let go enough to cum and during the whole experience I am honestly in my mind going, no, no, no, no, get it out, get it out, yes, yes, yes, yes, no, no, yes, yes, yeeesssssssss...