Bit of a dumb question which is probably true for a lot of guys but do you struggle with anal, whether you're being penetrated by another man or using toys, even when using lube?

I ask this because sometimes when I'm riding my dildo, no matter how much lube I use, it still hurts. Most of the time it feels fine thankfully. I lather my dildo up with a nice layer of lube, apply a generous amount of lube to the outside and inside of my bootyhole, pop myself on, pump myself a few times and away I go with no issues.

Sometimes though it really hurts, no matter what I do and no matter how much lube I use. I'm not sure if it's just my hole being temperamental and not opening properly, though when I check with my finger it seems fine. I feel like I'm wasting lube when it doesn't always work out and trying to continue through the pain is just way too unenjoyable. I always make sure to clean myself and let anything pass beforehand so that I have no issues later on, and that I'm warm enough to allow my bootyhole to relax. It doesn't always work though.

Is this a common issue for a lot of folk? Sometimes it's like my dildo was built for my butt, it fits perfectly and my butt has no issue accepting it, whereas other times I feel like I'm bouncing on a sword.