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I am 20 years old now, and am planning on having sex with my girlfriend of 1 year today.

Since I am an uncut virgin, I am wondering when I use a condom, will that cause pain or cause my frenulum to tear or bleed.
I want this to be a special time for both of us, and I think it would be awkward if something like this happened.

thanks in advance.

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Use of a condom will NOT cause pain and tearing.
If you have any doubt, a small amount of lube inside the condom, covering the head of your penis will assure that things slide and glide in there.

As for how you position your foreskin, I'll defer to some of our uncut brothers to advise you on this, as I am unfamiliar with that condition.

You might consider picking up a book or two on sex and intercourse before you set out to do the deed.
May I suggest "The Guide to Getting it On" by Paul Joannides (Goofy Foot Press)
and/or "Sex is Fun" by Kidder Kaper

Both books are liberal and fun while being educational.

Good luck.
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