I never was confortable with dryness, so I learned early in my teens as you are now, that lubrication goes a long ways when it comes to comfort. I was a virgin to, up until I got married. The foreskin always feel tighter when your skin is dry. I don't/never had a problem with mine. Like yours though, it always was a bit tighter when dry. I would suggest lubricating it/keeping it lubed and you won't have any problems. Before intercourse I've always added my favorit lubrications to my penis/foreskin, for a smooth transition. What ever you have around the house, baby oil, vaseline, lotion. After every shower I moisturize my skin, and I've never had a problem. When masturbating the friction of tightness is great, but there are always those times when you want your skin/foreskin to simply glide over the head.
By the way, you shouldn't have any problems with intercourse if you take your time.
The virgina's wetness will give you the lubrication you need, but you will need
to slowly enter, teasing a bit until the head/foreskin is lubricated before intering fully. If you don't, not only will she be sore, you will as well.
Of course if you're waring a condom you won't have to worry about it. Just a suggestion.
Mabey not really a big foreskin problem. 
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