Throwaway account for obvious reasons.

I actually do have this. It's never proved a real problem though.

A few times, when she's too "tight", it takes some time to work it in. But once you've gotten it in and everything gets wet it all works out just fine!

The only time it's ever been enough of an issue to kind of actually matter was when I was having standing sex against a fence, and I was having trouble putting it in (naturally you play this off as teasing her, works great). I decide to back up and try again. When I look down I see my foreskin pulled back further than I've ever done and suddenly it's painful. The arousal had kept me from feeling it, but when I saw it that was all undone. Nonetheless I just pushed my foreskin back forward and teased her for a bit so the pain went away and went right back to it.

Moral of the story here, take your time and get everything all wet. You don't have to push your foreskin back to have sex, works just fine without it. Though getting someone pregnant might be tough, my cumshots aren't really "shots".

Though always remember to wash your dick, to include under the foreskin. It's uncomfortable to do, but do it.