yea this happens alot when you push the follicles in one direction for a long time then move them.
happens to me if i wear a hat for like a full day and then take it off, or if i sleep in longer socks makes your leg hair hurt and shit in the morning.
I honestly think you can condition your hair against it though, b/c if you wear a hat all of the time i bet the hole around the follicles widens from being matted down so there is more play before it hits nerves or some shit.
edit: this is a gay ass conversation, just sayin’