"The Essential Tantra, A Modern Guide to Sacred Sexuality" by Kenneth Ray Stubbs, gives a great demonstration of how to massage men as well as women in order to acheive what you are attempting with your friend. As a matter of fact, you may want to assist him with cutting the "emotional cord" he has with not being able to get off in this manner. Talking through it and allowing himself to "let go" will probably get him over the hump, so to speak...I also have to ask...how often does he get himself off? Through self love each individual, male or female discovers what it takes to bring themselves to orgasm, there by giving them the knowledge to tell their partner what to do in order to climax.

Priapos

That is a really great question! I find that after being brought to the edge several times, that it becomes extremely difficult to actually cum unless there is an intimate connection, or unless the girl is really dirty. Whatever you do, don't let it get you frustrated, because when I sense frustration or any kind of time limit, I lose the ability to cum altogether. I think the key is to keep changing it up. Too much friction in one spot makes it numb, and sometime the lightest touch is more erotic and will make a guy cum quicker than a hard touch. I really enjoy it when a girl tortures me of the edge, and the more she is into it the hotter I get, and the harder I cum. I have been able to cum so hard that I have hit the wall 10 feet away, but that takes hours of torturing. If it gets to the point of being too sore or tired, I suggest slow way down and take a rest. Even just laying there resting you hand on his cock can be hot, or try getting on top like you are fucking him but play with yourself with lots of lube, so that you hand brushes up against him lightly. If he really needs help, make yourself cum hard while wiggling your body on his while being very vocal near his ear... the sound and feeling of your body cumming will get him back to the edge again but don't pass up that chance to make him cum.