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Let's review the operation of a correctly functioning foreskin during sex. When you insert the penis into the vagina the foreskin will go back by itself and it will locate itself correctly inside. That is to say the head will be all the way out of the foreskin when the penis is all the way inside. As you pull out the foreskin will remain in place against the vaginal wall and the head will be going in and out of the foreskin. This provides the greatest comfort and pleasure for your partner and you as your head will not be scraping against the vaginal wall but it will be coming out to get caressed by the soft flesh inside at the end of the stroke.
As you can see, if you pull it back before inserting it, it will make no difference. It will still locate itself properly unless you hold it back so your head stays out and functions like a circumcised penis.
Since there are quite a few circumcised men and there are certainly ladies who have sex with them, the rubbing of the head against the vaginal wall is something that women can obviously become accustomed to, and some probably prefer it.
If you are going to use a condom I would think it best to pull the foreskin back before putting it on, so your head will not be poking out of it with each stroke, attempting to break through the end of the condom.
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