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Ustwo... wow. Just wow.
But I have restrained from posting this as you mentioned it was a close relationship, I imagined that this issue would have been known to you. As others have already popped it: I instantly thought abuse when reading your post. My first girl friend was sexually abused when she was younger and it impacted that time when we, as teenager couples, should have been exploring each other sexually.
How I helped her through it (fuck, this just sounds bad like taking advantage of a broken girl, which she wasn't!) was that I was not her former tormentor. I didn't think like her tormentor. I didn't move like her tormentor. I didn't want like her tormentor. I wanted her to be happy, I wanted her comfortable, and most of all I wanted her to scream my name in ecstasy. That last one broke the tension into a good laugh and the relationship really moved forward from there.
Just my 2 cents.
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