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Um... how about they do everything but intercourse? Masturbate together, masturbate each other, try anal sex, try oral sex, watch porn, get some sexy massage happening, try some toys. Tell your friend to do every sexual thing he can think of except putting his penis in her vagina and I'm sure they'll be fine.
And persuade the woman to use some sort of birth control and make the guy wear a condom if the last few times have resulted in pregnancy. That sounds very suspicious.
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