While I love performing oral on him and am generally very attentive to his requests, this one sort of spooked me. During last night's BJ, he asked me to stick my finger in his ass - I was taken aback a little and sheepishly confessed I was afraid of hurting him. He understood and we settled on an enthusiastic rimjob instead.

Now, from what I gather, I'm going to be stimulating his prostate (er, once I get up the courage to venture forth with this). But beyond that, I'm clueless as to the mechanics of it all. How far am I inserting my finger? Steady pressure or thrusting? Keep it in until he cums, or remove it periodically?

I'm hoping one of you handsome males can elaborate on how this feels and what I should be doing in order to get his eyes rolled into the back of his head. :)

UPDATE: Mission accomplished, and fun was had on all sides! Will definitely repeat and I encourage the rest of you ladies to comply if the same request is made of you one day - the amount of pleasure you're capable of giving your man is astounding!