It all depends on the guy. With me, my boyfriend knew better then to go far in with his finger the first time, and to gradually work me up to it. But the first time he actually went in, it kind of hurt. While getting fingered, I think it depends. Usually, my boyfriend will be fingering me with one hand, groaping my boobs with another, and he'll have his ear next to my face, so he can hear me moan... We don't make out too much durring it. But if he's going too far, too fast, or too hard, tell him. He WANTS to make you feel good... He won't want to hurt you. Just try to stay relaxed, and have fun.