As a guy - all anal play involves stretching - and yes I like it. My wife has always been worried that with larger toys she would get stretched out - making her too lose for me. With experience she realizes that in practice that hasn't happened - so she is enjoying the stretch she gets from her Maverick and Outlaw dildos.
I enjoy the sensation of stretching up to a limit that I'm already comfortable with, but I'm not a fan of the stretching that's involved when it comes to breaking in a new larger toy, as that can be ouchy, even when done slowly and cautiously.
I think this topic should have been a little more... Specific? I think some people here are talking about fisting/using large toys and some people are talking about warming up before a good exercise, haha.