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Do occasionally ask him, “Do you like this?” Use “yes or no” questions so that he does not have to think, so that he can stay in a state of relaxed arousal. Keep the penis stimulation going the whole time to help keep him happy.

Now here is a very exciting part: the “fireworks finale” to prostate massage, which very few people in the whole world have experienced. So few, that you almost never hear anyone talk about their experience with the prostate during ejaculation.

The first time this occurred with my husband, my thoughts were, “Wow! What was that? Did that really happen?” The second time was a few months later◦— after all, one doesn’t tend to do these things every day. And yes! It really did happen again.

I felt I had discovered something totally new: undiscovered territory on the world map. It is so amazing to go to medical school and think you know pretty much all there is to know about the human body. What a surprise to find the body right in front of me doing something that I had never even heard of.

Here’s what I’m talking about. If you have your finger on the prostate and the man is about to ejaculate, the prostate poofs out and gets firmer. And then, as he is ejaculating, it shrinks back to normal. There is no pulsing. It is just a one-time thing of it getting big and then contracting back. Amazing, isn’t it! This gland that we thought just sits there, calm and inscrutable, is actually is quite busy during ejaculation.

The puffing out of the prostate happens at the same time he is experiencing that feeling of inevitability, that feeling of “Oh! I’m gonna come.” So in a sense, he has a way of communicating his ecstasy without making a sound. Experiencing his orgasm this way is very intimate and exciting. I think it’s the best show on earth!

By the way, the finger communication is just one way of finishing the fabulous experience. You may choose to go from the prostate massage to sexual intercourse before he orgasms. Nothing wrong (and a lot right) with that!

Prostate Milking

There are several slightly different definitions of the term prostate milking. Some people find the term ‘prostate milking’ more erotic than prostate massage even though the terms mean essentially the same thing.

Prostate milking is massaging the prostate with the aim of expelling seminal fluid from the prostate through the penis. This happens without an ejaculatory orgasm. Prostate milking is the same thing as prostate massage. However some men (and their givers) like the idea of expelling some fluid during that massage which is not part of the ejaculation.

The idea is to ‘clean out’ the gland. It also stimulates blood flow. This can be for the purposes of pleasure or for prostate health benefits, or both.

The fluid can be a few drops or more. Many men find that idea exciting and appealing however it is really not all that common to get fluid, especially a lot of fluid.

There is often a component of fantasy in the concept of prostate milking. It can be a great fantasy to get the prostate stimulated and have fluid released. Sometimes this fantasy includes being dominated. It is just fine to have fun with this fantasy. If you choose to act out this fantasy, just make sure that the actual prostate massage is still done with gentleness and awareness.

To milk the prostate you use the same techniques that we have discussed at length in the rest of this course. The motion most conducive to prostate milking are smooth, gentle, continuous strokes from the top to the bottom of the prostate. There can be stimulation of the penis with hand or mouth at the same time, or not.

Doctors will use what they call ‘prostate massage’ to get fluid to use in diagnosis. This the same thing that others may call prostate milking.

So have a great time exploring prostate milking as another aspect of prostate massage!

Putting It All Together

We’ve covered how to do all the stages: external prostate, external anal, getting inside, internal anal, and prostate massage. This chapter is about how to put all that together for one fun session.

Remember there are really no rules other than safety and mutual consent. This session is for you both to play in any way that the two of you want. It’s great if this turns out to be hot and sexy. And it’s certainly okay if it turns out to be an adventure, a walk on the wild side.

That said, here’s a map for putting it altogether. The guy may wish to go to the bathroom to check himself as we talked about in the messy section. He might want to take a quick shower, or maybe use handy wipes for that, instead. Now you want to warm up the room so you are both comfortable without clothes and gather all your supplies.

When you start, take a second to be with each other. Maybe share some kisses. And guys, don’t forget to get her turned on, too. Maybe the two of you want some regular sexual play first, whatever that is for you. Maybe some oral sex for her, some clitoral stimulation, maybe a little vibrator action, maybe some G-spot massage. She may want to have some orgasms, or to save them for later.

Next, position him comfortably. And tell him that this is a treat meant just for him in three different ways. First, remind him that he does not have to do anything, other than lie there and enjoy, but that he is still totally in charge. He can request things, he can say yes or no to anything. Second, tell him that having an erection is fine, not having one is fine, and anything in between is fine too. And third, tell him that he is free to ejaculate early, or in the middle, or late, or never. Whatever he wants.

After that you might want to express appreciation of his penis and his ass. Tell him how handsome and sexy he looks. Keep your eyes on him. He may want to look at you, or just close his eyes and let the sensations wash over him.

Start with just general body touch, caressing and stroking everywhere to wake up his senses. Then a bun massage◦— a firm and deep one◦— would hit the spot. The next step is a genital massage, which you keep going during the whole session. Maybe some oral sex on him and maybe some nipple stimulation if he likes that sort of thing. And I do realize that you’ll run out of hands somewhere along the way.

Next on the agenda is the external anal massage. Remember, as always, that it is really, really important to ask◦— and wait for his answer◦— before going inside. Then slide in your finger, do an internal anal massage, and the actual prostate massage. Keep asking him what he likes, phrasing the questions for yes or no answers.

And also remember that, during the genital, anal and prostate massage, emotions may come up for him, just like they might for a woman during a G-spot massage. These feelings are unrelated to the fun task at hand. They’re about him, not you. They are just old, diffused emotions that he is releasing. Don’t ask him about them or add comments, other than maybe to say, “You are doing great.”

He may end up having the experience of some non-ejaculatory orgasms, some peaks of sensation. Maybe he will want to have an orgasm towards the end. Maybe he’ll want to use his own hand for that, with your help or with you just watching. If your fingers are inside him, they may exit slowly or stay put; his choice.

Men like varying amounts of sensations on the penis as an orgasm finishes. So you’ll need to learn that about him. Some guys get a huge kick out of having your finger on the prostate at that moment, and some really don’t.

Remember, too, that a successful session may end with no orgasm. He may have had enough, or maybe your hand is tired, or maybe it’s time for you to have another orgasm, or whatever. You may end up having intercourse.