Are you fingering yourself or a boy fingering a girl?

No, it shouldn't hurt. If it does, something is wrong. The vagina needs to be wet before anything ever goes into it. If it's not wet, the girl is not turned on or ready for anything to go in there. Try spending more time getting her turned on, kissing, touching, etc. If the girl has problems getting wet, try using some lubricant (you can buy at the drugstore, or spit or water).

A girls gets turned on, her vagina gets wet. Then things can enter. Not before, or yes, it will hurt.

No, it should not hurt. As Georgia said, any pain is a sign that something is not quite right. Usually the problem is simply not having enough lubrication. Girls can make lubrication, but if we don't make enough, we can buy water-based lubricant at the store.

I remember the first time I tried sticking my finger in my vagina and yeah, it is very very weird. My personal suggestion is to do it in the bathtub, so then there's lubrication everywhere! Secondly, the warm water helps you to relax which is really important.

Well I was so wet I could have drowned my self but still nothing. Maybe im not going in correctly.

Do you use tampons at all? Youll have to get the correct angle to get it in. Also try different positions such as squating as its often easier to insert a finger then than if your lying down.

no I dont use those. But I'll try different positions and update you all.

You really have to wiggle around a lot at first. I know I did...

I tried squatinn and got a lil more in but jus a lil bit. It began to hurt so I stopped. Do I need to cut my fingernails or something because everyone esle says its not supposed to hurt.

I think in going to just quit ARGGHHH

Do it in the bathtub!!! lay back, relax, be warm. I don't think I could easily finger myself squatting... I would definitely suggest not having long fingernails until you're good at it.