You could use a vibrator I guess. As far as causing health problems, it shouldn't. I used to ride the rodeo circuit and I rode bucking bulls (yes I am a girl) and so my cherry was popped because of that. I never even knew when it happened. As for you experiencing pain, I feel sure you are gonna feel some discomfort. Just try to get yourself very aroused and use lubricant and try to relax as much as possible. The more tense you are the more it will hurt. Hope this has helped you some.