Beware
I'm a man. I know this issue and it's sad (mostly for your BF, because he's hurting... probably really tormented) All men struggle at least a little with fear of inadequacy.
With what little you describe, I can guarantee you, your BF is absolutley obsessed with size, not just his. He knows where he stands. He's seen much larger men, both in person and in pictures and video (lots of porn I'd guess). He's heard about women with very large lovers (maybe a friend of yours) and made himself miserable fantasizing about how turned on she must be by him.
His queries about your previous lovers is part of this, and a bad sign. He needs help. Therapy.
Odds are he's deeply troubled by his obsession with penises and has doubts about his heterosexuality, no matter how much sex you two have.
He may have been abused in the past.
Wanting his penis to be too big for you and painful, is a type of S&M and/or rape fantasy. Something gave him a bad self image.
Try to get him to talk about it with a therapist.
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