Yes, you can 'pop your cherry' with a finger, penis or sex toy... Your cherry is a thin piece of skin that breaks when you are penitrated for the first time. Some women bleed alot, some bleed a little. Every woman is different.

As far as the pain goes, again every woman is different. The pain is not mind numbing and horrible as many make it out to sound. I never understood the 'first time horror stories'. Sex is uncomfortable maybe, for the first few times. You might be a bit sore, like when working out new muscles for the first time.

As far as the things you need to know... just becareful. Always use protection. You can get pregnant during your frist time and you can catch numerous STDs including HIV.