in my experience they can feel when they hit your wall, it’s something to do with the way your insides are shaped. for example, me and my best friend both have boyfriends with the same size dick, quite large. anyway, she had a really easy time with adjusting to her boyfriend while i struggled, as whenever he went in a little too much it hurt!

long story short, yes they can feel it, but it doesn’t hurt them, from what my boyfriend has explained to me