|Is that because you were never a virgin, or were never WITH a virgin?|
I'm not sure why Mr. Sensitive is having me answer your question. The bottom line is I have no idea what you're going through at all!
Talk about everything before...and after
All I can say is, ask. Ask if it hurts, ask what feels good, ask if she's okay...don't force anything!
I do know that afterwards things will be complicated. You will have literally crossed a threshhold that adds layers of meaning, depth, and confusion to your relationship. Now what? You'll both ask.
She May Assume You Are Forever
She may feel like you are the only one forever. Is that true? Are you two looking at marriage? If not, then you two should talk before how it will feel afterwards. My guess is you both have deep feelings, expectations, hopes, dreams, worries, fears, needs, etc.
So, don't just get drunk and screw! This takes some careful planning before hand. It takes compassion, sensitivity, and love afterwards. Respect her. Know that even if she says she's ready, it will surprise her on many levels. It might surprise you, too!