How to eliminate discomfort when doing it with a virgin woman

I wanted to know how people get rid of the pain thats to be expected when you have sex with a virgin woman or at least someone who is still new to sex..

I thought having her go on top would allow her to control things to her liking.. But I was told its extremely uncomfortable.. I would really like a woman's perspective on this..

I dont think missionary works because its reliant on the male partner inserting it in and he may go in too hard or not good enough.. As a woman would bieng on top help you break your hymen and such without really causing the pain associated with it? or would it not matter what position you were in? Would you still feel the discomfort?

Also, For a virgin woman doing it for the 1st time will bieng on top allow her to reach her own orgasm as you learn what her body is like? I am not sure I know the female body enough to really guarantee her orgasm. I figured since this object is inside of her she can feel whats good and what hurts and stroke herself over it as she finds it most pleasurable then all I have to do is hope I dont cum too quickly until she is done satisfying herself.. I am probably wrong.. But then I relatively a virgin myself (even though I am not really)..

I am Just a guy with no experience except for the 2 times I did have sex (Pitiful experience). Asking for the eventuality my next partner is a virgin. The previous ones werent and this was much easier with them. No fear of really hurting them as I may have a bit of a girthy penis down there.. I am certain someone who has never put anything in their virgin would face enormous pain from a 1st time penetration? I could be wrong.. Do assist..

Sorry if anything sounds off, I am pretty new to sex having done it only twice in my life..