How can I make our first time less painful for her?

She could have a pretty simple medical condition that's causing to be painful for her. She should go to a gynecologist and see what's going on. Or she might have a really low pain threshold. The first time is supposed to hurt, but not enough to make her cry out or anything. Have you tried with her on top? My first time the boy I was with tried being on top, and it hurt too bad, so I went on top and it didn't hurt as much. If it's really hurting her, she should see a doctor before you try again, there could be a lot of negative mental side effects from trying to have and it being painful every time. She might even lose her desire to have altogether, or have an adverse reaction to ual or romantic stimulation.