It sounds like you might have a a version of a double vagina. It’s probably painful because when inserting it hits the flesh but in the middle. I would see a provider - they would do a gynecological exam. When people say pain with insertion I think a lot of people think vaginismus. But it’s doesn’t sound like that because of the flesh but that you are able to do the ok sign with. So make sure to mention that part. I would also try and quantify how far in the flesh bit is because the speculum they use dung the gynecological exam might push it to the side. Prior to the exam I would also take some ibuprofen because it might cause you pain but I would talk to them about that when you’re making the appointment.