I wanted to update the original post with another technique which keyholders might find gives good results but is perhaps a little more tricky to master. My keyholder has recently been using this technique quite a lot and afterwards I experience very little in terms of drop in sexual tension and remain hard until she has finished using me even though there's nothing left in my prostate.
The prostate gland is most easily accessible by inserting a finger or two into his anus and feeling for the walnut-sized gland - if you need any more advice about this then just do a Google search - there are some very good diagrams out there. However, you can also manually stimulate the prostate from the outside in the area between the base of the penis and the anus.
In my experience, an external milking is a lot less pleasurable than just about anything else and if it's done properly I often have to ask my keyholder how much I've cum because although I can feel the prostate emptying, I don't get any pleasurable contractions.
The first time you try this technique, it will make it easier for you to feel the prostate from the inside, to make sure you've found the exact area on the outside - apparently you can actually feel external manipulation of the prostate on the inside. As an aside, once you know you have the correct spot, inserting a prostate massager before external milking will give you corresponding pressure on the other side of the gland and will usually make the process a lot quicker, although for me it feels more pleasureable.
Finding the right spot
Position your subject so that he is lying on his back. You will probably want to secure his hands to give you complete control and increase his feeling of submission. If you feel down his erect penis on the underside (you're kind of stretching the ball sack downwards) you can feel right to the base of the erection, inside his body, at this point you're heading down towards the perineum. Not far from the base of his erection is where you'll find the prostate .
Milking to give minimum pleasure
As in the original post, some (most?) men - myself included - can't be milked without at least a little penis stimulation so a teasing session is probably required. When you're ready to commence with the prostate stimulation, use two fingers, one just either side of an imaginary centre-line and begin to stimulate the area described above in an up and down area. You will soon know if you've found the correct spot because your subject will most probably wriggle. Continue stimulation in this way, with as much or little other teasing as you like (e.g. squeezing the balls, running your fingernails up and down the ball sack etc.) and after a period of time you will be able to tell that the subject is on the edge of cumming. At this point remove all stimulation, except for the slow rhythmic up and down stimulation with your two fingers and continue until the prostate is empty.
When my keyholder does this to me, it takes about 15 minutes and other than very occasional touching she is able to milk me without touching my penis (certainly in the last 5 minutes or so), and of course doesn't need to wear a glove. Towards the end of the procedure she can tell I'm about to come because I often am humping mid air in an attempt to get some stimulation to my penis.
The external milking is probably the most humiliating of all techniques discussed in this blog - especially when I'm restrained, have a prostate massager inserted and then just rhythmically rubbed until my prostate empties.
Just a little advice though - be gentle! you don't need to use excess pressure on the prostate and it'll probably do the subject no good. Gentle and rhythmic is the order of the day.
