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Assuming for now that the man is on his back, slip a finger or two into the anus facing upward (fingernails down). Then curl your fingers (what some people describe as the "come hither" motion). Most men claim they like it stroked or massaged.
When you stimulate the prostate by hand, be sure your nails are trimmed. The anus is a sensitive body cavern that can tear and scrape easily. It's not as durable for penetration as the vagina. You may want to snap a latex glove on your hand, found in many drug stores or sex shops, which will make rear entry a smoother process. There are also finger cots you can purchase that serve the same purpose. In addition, don't forget the lube. The anus doesn't naturally secrete slippery, sexual fluids conducive to easy gliding. You can buy commercial "personal lubricant" in most pharmacies. If you are using latex gloves or condoms for STD protection, remember to never use oil or petroleum lubricants like Vaseline or massage oil as they destroy latex.
Fingers aren't the only anal pleasure enhancers. There are some great sex toys that excel at stimulating the prostate. We recommend Anal E-Z Bend Vibe
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