Dude, there is nothing wrong with it.
Some foreskins just do not retract, besides usually it will slide back as you enter her anyway.

*also* condoms???? I treally isn't going to make much difference.
I do not understand why americans place so much intensity on what the foreskin (or lack of) is like.
I live in the uk and have only ever been with one guy who didn't have a foreskin.

Most guys erections do not cause the foreskin to fully retract at all - my guess - you read/watch too much porn - honestly - real life is nothing like the movies!

Kia nailed that right on the head. Good response.

Yeah honestly, i've only really started having sex in the last two years, and for me with masterbation my skins always never retracted back, and might sound silly but I just assumed that you don't need to if you're uncut. But most of the time when you're inserting it into a girl you'll have a lot of precum which helps it slide back for a start which you don't really get with masterbation until close to the end (i find) and just eitherway sliding it in usually will slide it back. Otherwise if you're still finding this problem I guess rather than her inserting it, insert it yourself, and just use your index and thumb as you go to insert it and pull that back as you're pushing forward into her and you should be fine.

Well, if you are using condoms, and you really, really should, then she isn't going to notice anyway. If you are with a girl who has been with a man who is uncircumcised then she is already going to know what it is suppose to look like, and if you are with a girl who has only been with men who have been circumcised then she isn't going to notice anything, because it will be the first uncut one she has seen. Don't stress so much about it. As long as everything works it really doesn't matter and if you are having sex with someone you love (which you should) then she isn't going to care about your foreskin not retracting.
And remember, a woman can get pregnant from precum.