Hey, no worries! Nothing’s out of line to ask me, if a person’s curious about it. :3
I wish I had a more satisfying answer to give you than “I could penetrate most of the way into a silicone vagina when it was really *really* lubed up, and when I’ve tried going in anally, I pretty much couldn’t press my way in at all.”
While I personally don’t intend on getting an erection device, I did try the trick where you roll on a condom, then another condom over that, and have at it. I’ve heard different folks having varying levels of success with that; it apparently does work for some, but it didn’t for me.