Sorry to break it to you, bro, your mate has a bad case of phimosis. I reckon it's so bad for him that he's relying on using a condom to keep the foreskin over the dickhead. Because a bad phimosis sufferer would be really afraid of letting the dickhead pop out. It's always covered in the foreskin, it has become too sensitive that it gets downright painful with any direct touch to the dickhead.
And that also means, your mate would really struggle with fucking without using a condom because it would be impossible to keep the skin over the head then.
It's a terrible thing, phimosis. I had it too before I was cut, but not as bad as your mate.
EDIT: And that thing about protection against STI is laughable. The opposite is happening. The skin over the dickhead creates a space where the STI vector can linger, all warm, wet and cosy.











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