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Taken from here:

http://www.spankingmyhusband.blogspot.com

Prostate milking manual: Step 1. This is the hardest step: No orgasm of any kind for a long time.  At least a week is needed with no release.  You will probably need 2-4 weeks for you to be successful the first time. Step 1 is the hardest step to achieve.  For us to be successful at this the first time, Evan went approximately 3 weeks without ejaculating.  That was a really long time!  I know that there are lots of people that have gone longer, but this was difficult for him.  He was used to ejaculating once or twice a day for years and years.  He would sometimes go 2 or 3 days without ejaculating, but those were unusual times: he gets super horny if he hasn’t ejaculated in 3 days.  So this was difficult for him. And when I say no release, I mean no release at all. After some experience now, I think that so-called “edging” is too dangerous to risk release.  Any time you release any sperm at all, even just a bit of pre-cum or one squirt in a partial release, then you have to re-fill that before you can milk well.  For example, on one early occasion – maybe our third or fourth milking session ever – I was edging Evan, and he accidentally shot one stream of come.  This was definitely not a full come: I stopped early enough to stop that.  But a lot of come came out.  When we tried milking the next day, nothing came out at all.  Our guess is that the big early shot of come is what I would have been milked out if he hadn’t let that go the previous day.  So my advice is no edging.  Now, when I want to milk Evan, I try to keep sexual contact with him to a minimum for days in advance.  That is, I don’t touch his penis for long at all.  It’s fine to touch it until it’s hard, but then I leave it alone.  (Of course, this does not stop me from getting oral pleasure from Evan: it’s just him who needs to be denied for milking to work.)

Evan from day 2 until day 21, when it’s time to milk.  That’s an exaggeration, but what a nice picture: I have my hands full.

Step 2. Find a firm dildo to massage your prostate with.  Perhaps you can use your finger(s) instead.  We weren’t successful with fingers however, possibly because my fingers cannot reach deep enough to massage the right spot.  We use the red “more” feeldoe dildo from: http://www.feeldoe.com/ I like this dildo for milking because it’s smooth, and firmer than most dildos.  (I realize that these dildos are expensive, but they are good.  We are not paid in any way by this company, and we recommend them.  I see that they now have a “stout” version: I would have got that one if it had been available when we bought ours.  Evan likes a thick one in his behind.)

The feeldoe dildos

Step 3: Prepare yourself for anal play. For us, this means that Evan gives himself an enema, or I give him an enema.  This takes a while: he takes 2 quarts of plain warm water, or sometimes water with a bit of white vinegar, or sometimes water with a bit of mild hand soap.  I fill him up, while he is kneeling the bathtub, and then have him hold it for a few minutes.  I plug his bottom with an anal plug to hold the water in during this period.  I time the hold so that it’s 5-10 minutes (depending on how he feels: I don’t want to do him any damage), and then he releases the water after I leave.  We wait for 1 hour or more for the water to clean him out.  Then he is nice and clean, and ready for his milking. Step 4. Find a comfortable position for being pegged (butt-fucked).  We have mostly used positions where Evan is kneeling on the bed, or where he stands up and bends over.  And occasionally I have milked him on our spanking bench (which is a great place for milking).  I have seen that others get pegged while on their backs.  I imagine that this would work too, but we haven’t done this.  We like a position from which the semen can drip down and catch in a container, so this means that Evan has to be bent over. Step 5. Using lots of lubricant, insert the dildo into the anus.  Take your time to get it in comfortably. Step 6. Aim the dildo at the prostate.  The prostate is a little round soft thing in his rectum, underneath the base of the penis.  This picture is from the wikipedia page on prostatic massage:

Step 6: Now just simply massage the prostate with the head of the dildo, applying some pressure.  Do this firmly and smoothly, back and forth over the prostate.  (But don’t bang into it hard: the prostate is a sensitive part of the body.  According to the wikipedia page, you shouldn’t do this “vigorously” but I don’t know how to define “vigorous”.  Apply common sense here: if it hurts, don’t do it.) When I do this using the feeldoe, the feeldoe is aimed down, not up in its normal fucking position.  I find it easiest to use the head of the dildo penis aimed in this way to massage the prostate most efficiently. Simply repeat step 6 until you get some seminal fluid dripping out of the head of the penis.  For us, it takes a while for the seminal fluid to flow, approximately a minute or so of massaging.  The massage should feel really strange (according to Evan): it should feel like you need to go to the bathroom in some weird way, maybe like needing to pee or maybe like needing to defecate.  Unless it hurts, then just relax and try to enjoy these feelings.  As long as you have cleaned yourself well (using the enema), you shouldn’t worry about defecating.  Evan also tells me that he feels very submissive to me at this point, when I am massaging his prostate: apparently it’s when he feels most submissive to me.  He gets very quiet and subdued: not alpha male at all.  As you might imagine, I like this very much. Listen to your partner during this process: massage in a place that feels the strangest to him.  Evan tells me when I hit a spot that feels really strange, and then I massage over and over on that spot.  After a little while, he often can feel when the semen is going to start to flow, and he tells me.  The flow starts as a rapid series of drops – often a little spurt of a few drops at once – and then a steady flow of one drop every few seconds, drip, drip, drip.  I usually milk Evan for about 5-8 minutes.  At this point, the drips have basically stopped.  Then I often turn the dildo so that it has the normal side up, and I peg Evan deeply for a couple more minutes, just because it’s fun for both of us to do this. I like it when he moans his adoration of me during all of this process.  Sometimes he will say “thank you, maam” every time I push deeply on his prostate or penetrate him.  It’s good to be appreciated. Some information on the internet that I have found claims that for milking to work successfully, one needs to be in the right state of mind.  The author of these articles seems to think that the process is part mental on the part of the milkee.  We don’t think that this is correct: we think that milking is a purely physiological process: if your prostate is filled with overflow semen, and if you massage it right, then you will necessarily be milked.  This is certainly true for Evan: if Evan is in a ready state for milking (backed up for a week or more), then if I then follow the steps above, he will be milked of his excess semen, no matter what his mental state (that is, whether he wants this to happen or not). Step 7: Clean up.  We put a little dish or a cup below Evan’s penis during the milking process, to catch all the semen (the milk!).  We also sometimes film this process.  When watching the film, Evan has counted how many drops he typically produces.  Depending on how recently he has ejaculated before, he will produce somewhere between 30 and 60 drops of semen.  This can end up being equivalent to a pretty substantial come load.  Once the milking process is completed, I make sure that Evan drinks this down.  This is the one time when Evan doesn’t mind drinking his own semen: getting milked has basically no effect on his sexual excitement level.  After milking, he is still as horny as when we started.

This is at the end of the milking session.  Although it’s not easy to see, the bowl has lots of semen in it.

This is Evan drinking his milk.  (Good boy!)