I get more sore from guys who try to last for hours/all night. That's physically and mentally VERY annoying.
I don't think there's any direct connection between confidence level and/or skill and cock size. I remember one guy with a huge dick (took both of HIS hands to jack it off) - like, unmanageably gigantic and he was totally insecure, but maybe that's because whenever he took it out girls ran the other way. I refer to him as "log boom boy".
Hurting momentarily is one thing, getting sore and raw is another.
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