No - in this case pain is telling you there is something wrong and you are likely to do damage - that may be long lasting or permanent. We're not talking spanking pain here - seriously dilating an anus that is not ready is a very - very bad idea!
Hell no. Who and why would anybody enjoy pain in that area? I've had a little bit of an ache there at times like when I've drove for 8 hours straight, and no it's not fun. I think hemorrhoids, fissures, etc when I think anal pain, so no there's no way I'd enjoy that.
Not in any way. That is why some people think it is strange I am so into anal. Sorry...you can do anal without pain. Pain is a turn off for me, and thankfully my early lovers knew what they were doing and everyone since has been spot on. All gain, no pain. Happy me.
Sex is supposed to be fun-no pain. My wife and I tried several dildos for pegging ranging from 3/4 inch diameter to slightly over 1 1/2 inch diameter and found that anything over 1 3/8 inch diameter even with lots of lube is not comfortable for me. Many posts say 1 1/2 inch diameter and larger dildos are what they try to use, but for me would just be painful. I see no advantage in very large dildos for pegging. We have two favorite dildos one(Vibrating Leisure) is 1 1/4 inch diameter the other (Vibrating Mistress) is 1 3/8 inch diameter. Love the vibrations. The length is no problem. 7 inches long is fine.
The same thing applies to my wife although she can take a larger diameter vaginally, but she is also limited anally, but my penis is great.