Props: Because the anal tissue is delicate, you'll need plenty of lubricant (commercially produced lubricants such as ID Lube are the best). It is also sensible and hygienic to wear surgical gloves which you can buy from most chemists or supermarkets. For many people latex gloves are such a turn on in their own right that the sight, or the sound of them snapping over your hand, is enough to get your man really turned on and aroused! A good prostate massager such as the Aneros is an essential item too, because it has been specifically designed for the purpose.
Begin: Once you have your props you should get him to lie on his back with his legs apart and you kneeling between them. Of course you can also position him on all fours. Warm up his anus by massaging the nerve endings of the perineum (the area between his scrotum and anus) with the pads of your fingers. Pressing gently but firmly in a circular motion will help stimulate the prostate gland inside.
When he is ready the muscles around his anal rim (the sphincters) will begin to twitch, you should then rub over the opening with your gloved and lubricated finger, you can then judge whether he is ready to accept your finger and to further prepare him or the prostate massager. As you insert your finger you will feel his sphincter muscles contract. This may feel uncomfortable to him at first, but just like any of our muscles it can only stay in spasm for so long, within approximately 30 seconds the sphincter muscles should have relaxed and released.
Continue to masturbate his anus as you insert your finger further inside him, with your finger nail facing his back make a "come here" motion, your finger should now be pressing the prostate and it may give him the sensation of wanting to urinate, but this won't actually happen. At this point you can slowly remove your finger, and slowly introduce the Aneros inside him.
As you continue to directly stimulate the prostate with either your finger or an Aneros it will increase in sensitivity, so continue to stimulate it by rubbing all over the gland, and in a pulsating manner. Now you can play with his cock too. (Unless of course this is part of Milking a man locked in chastity, when the intention is ejaculation without orgasm).
As he approaches orgasm you will feel his anal sphincter muscles contract around your finger, his prostate will become swollen as it's blood vessels expand. At the point of orgasm his prostate will contract, empty and shoot semen from his penis.
I had it once. From a girl in San Francisco. She claimed to be a nurse moonlighting as a provider. I honestly believe she was a provider moonlighting as a nurse. Anyway, she learned a thing or two in a proctologists office and liked to practice on her customers. LOTS of fun, but only if the lady has training and constructive experience. Otherwise you dont get much out of it. I think a lot of tantra providers may offer the service even if they dont offer full service. Incidentally, the girl I saw no longer has an ad and I lost her number.
If I could post a follow-up: where would one go to find someone to give such massages? Is there a database or comprehensive web site available. I'm very curious about this.
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