What you describes as your first few times isn't unusual…it takes a few tries for many women to be able to accommodate their first partner. It was probably a combination of still having your hymen or some remainder of it and possibly stress (especially after it was difficult the first time).
I went without sex for a couple years once and when I finally did have sex after this hiatus it was not at all painful…in fact it felt even better after all that waiting!
It may take a while for you to get the hang of things with a new partner…sometimes it takes a little while to figure out what feels best. But it shouldn't feel like you're losing your virginity all over again.
Do watch out for those pesky urinary tract infections…the bane of any new relationship.
Good luck!
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