If i fingered myself for the first time, would i bleed? Like does that ‘pop the cherry’?

Watch this video.

You cannot “pop your cherry”. It’s a grossly incorrect term. (By ‘grossly’ I mean both gross and huge.) Your hymen is probably already stretched or torn enough from other normal, everyday activities that using your fingers wouldn’t be enough to cause bleeding. It is possible though.

Just watch the video.