I agree with the above comments. if you are too dry it will be uncomfortable. i know my first time it did hurt a lot. but its almost like sex. it always hurts the first time. but after a while it is okay. when i got fingered for the first time it was painful. but now i have been with my boyfriend for about 6 months. and im his first real girlfriend and i had to give instructions because i am sensitive down there and he was okay with that. dont feel bad just relax and it will be just fine.
I agree with JustJesse09 -- if you're too dry it will be extremely uncomfortable. Ask him to use some type of lubricant on his hands [Saliva works, even] and if you're nervous just try to relax because your muscles will relax down there, as well.
agree with above... Sounds like he's being to rough!!! Or if you are dry it's going to hurt too... I'm 35 and I'm still sensitive down there... lol If it hurts tell him, give him instructions it's yours he doesn't own the instructions so sometimes we have to guide them so that we can get satisfaction!!! Try some lubercation too!!!!!!!
Tell him to be gentle, and take it slow...he may be being too rough or to harsh