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ashap - he wants to do it because if he has sex without a condom he probably won't be able to go all the way in without the foreskin pulling back farther than usual, and hurting a lot. And if it gets pulled down beneath the head he'll have an excrutiating time trying to get it back up again since it's so tight.
And if you can't pull your foreskin back you can get all sorts of gunk trapped beneath it (urine, sweat, semen, etc.) and that can start to smell or get infected easily. If someone can't pull their foreskin back all the way there's a real risk of this happening.
Everyone with a penis should know how to keep it clean, but when it's something like this where it's not taught in sex-ed and it's hard to know if you're 'normal' compared to other guys, it's understandable that he's worried about it.
There's nothing to be scared or worried about, I'm probably making too big a deal of this, but it's only because I've had first-hand experience of this earlier this year and I'm just trying to pass on what I learned.
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