Some couples enjoy this sort of thing but I can't help but feel your guy is a desperately insecure man, that has asked you to degrade and humiliate him (commenting on wanting a penis bigger than his during sex) which you have gone along with (thereby cementing to him that he is indeed, deserving of such humiliation and demasculation).
The fact that he seems miserable after this happens, despite how arroused it makes him during the act speaks volumes of this being an unhealthy situation for him.
There are women, lots of them, that would be satisfied with his size, that would indeed get pleasure from not only his penis but his eagerness to satisfy in alternative ways... that could make him feel like the man he wants to, deserves to feel like.
I think you have to take a good long hard look at yourself and ask if you could be that woman? Or if you can't , do you want to be the one thats contributing to this self-inflected emotional scarring that he is asking you to?
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