Kissing with a cut?
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There is always a possibility but ,as the person above said, chances are slim. I'm not sure if your friend would appreciate the taste of your blood.
I suppose it might be possible, but the odds are vanishingly small.
Disease is always a possibility when you are having unprotected sex in any form. How you "hook up" is as crucial to the answer is that you hook up. Blood borne pathogens need to have an access to the blood through a viable host. I suggest you think of a safe method of sexual pleasure every time you engage in sexual activity. Remember you, in effect, will be having sex with everyone he has ever had sex with and those partners as well. If you can't or won't be celibate, at least be safe. If that isn't cool with him...he's a loser in the first degree and you really don't want him.
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