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I'm 17 and until recently I did not know that the foreskin should retract. After continual stretching over about 2 months, I'm able to retract even when erect.

When I retract without lubricant, the skin moves back past the head and sort of 'wrinkles' behind the glans. The foresin usually covers the head when I let go. It does not stay behind the glans.

If I use a bit of lotion on the head and coronal ridge of my penis the foreskin retracts differently. The foreskin seems to roll up much 'tighter' and when erect, it remains behind the glans. When I masturbate like this, the outer foreskin rubs against the glans then moves back. It does not cover the head until a little flaccid.

My question is how should the foreskin behave during sex? Should it continually go back and then cover the head or should the inner foreskin remain retracted while the outer moves?

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Ideally, you would want the condition described in your third paragraph, not your second. The rim of the penis head provides stimulation for both you and your partner during intercourse. If the foreskin rolls back and forth over it, this is defeated and your are essentially "doing" yourself inside your foreskin. The more you can keep it retracted, the more the rim has a chance to breathe and flair out, which will improve everything.
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Every one has slightly different penile and foreskin anatomy, so everyone gets slightly different results from retraction. There is no right way or wrong way.

One can expect the foreskin to move some during sex. How much it moves depends on how long ihe foreskin is, how long the frenulum is, and how long the penile shaft is. Everyone is different.

 

In my case, when I retract my foreskin, I get folds of foreskin at the base of my penis. When I let go of my foreskin, the folds unfold and push my foreskin forward over the head.

 

When I have sex, my foreskin retracts as I go in and it recovers my head as I come out.

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What you describe without lube is entirely normal. Which way feels better to you? What women often prefer about uncircumcised men is that the foreskin cushions their most sensitive parts from the coronal ridge, which in some cases can even cause injury to the woman. Personally, I enjoy the feeling of the foreskin's gliding back and forth, and try to insert is a way that gets the most foreskin inside my partner.
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When I have sex, my partner's vagina grips my foreskin and as I thrust my shaft moves within my foreskin. There is little or no friction between the vaginal walls and my shaft.

This is my experience but others may have different experiences.
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What happens if i have a short frenelum? Say my foreskin doesn't go back further than behind the head? Will this tear the skin while I thrust forward or it would be fine? Thanks in advance for your inputs
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