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By stimulating the prostate, you can reach orgasm without ever touching your dick! Which is why you need some advice before embarking on this epic adventure. It almost never happens, but preparation will help you get over this, and also ensure that your girl is not grossed out. Douching enema is the best way to prepare. Have a shower if that will help you feel comfortable. If you or your partner feel it necessary, use rubber gloves the first few times.

Also, long fingernails are a no-no!

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Massage the asshole and cover the fingers in lube. Go in slowly, bit by bit. The prostate swells when you get an erection, and is easier to find. Otherwise, guide your partner.