My ex's foreskin was like yours I think.....it didn't go all the way back completely exposing the head, and it was something I had to bear in mind when I was using my hands to pleasure him. It did however, move a little during sex, and wearing a condom was never a problem, but then I don't think the instructions on the condoms I've used, have ever mentioned pulling the foreskin right back.
As for how far it gets pulled back during sex, I'd say it can depend on a lot of things. I'm afraid to say that on two occasions, I've caused some mild injury to penises during sex, where the foreskin has gone too far back and the skin has split a little. On the first occasion, it was with the above mentioned ex while he was taking me from behind: in my enthusiasm, I pushed back onto his penis a little more energetically than I should have done, pushing his foreskin back further than it would comfortably go, which did cause him a little bleeding and some pain (nothing compared to the pain he'd caused me in the past by not being gentle enough though!). A similar thing also happened with Fussy once, which, again, was entirely my fault, as I 'raped' him one afternoon, mounting him before I was quite lubed up enough for it to glide in easily (damn me and my nymphomania!)
However, I'd say that the risk of that happening when you're wearing a condom is pretty much nil, since they are quite protective and that it really isn't something you should worry about, since it's not exactly a frequent occurrence and on both occasions, I think I felt worse than the man in question, for being too enthusiastic.
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