Dating Kinky Presents: The Big Book of Ass

Dating Kinky Presents: The Big Book of Ass

Big Book of Ass Cover

What Is Prostate Milking?

Prostate milking is prostate massage to orgasm without other stimulation.

It was originally done for medical reasons because by massaging the prostate you essentially flush stagnant and toxic seminal fluids from the prostate gland.

This reduces chances of prostate cancer, which is a good thing.

It’s also a pleasurable thing for many.

Prostate milking removes the orgasm from the traditional friction-and-ejaculate orgasm most prostate-havers are used to, and can be a good way to introduce multiple orgasms, if you/your partner have/has not yet experienced them.

While prostate milking and prostate massage are often used as interchangeable terms, some differentiate the two.

In that case, prostate massage is done for pleasure, while prostate milking is done with as little pleasure as possible, to simply stimulate release for health reasons.

How is it done?

Well, a finger is a good way to start. However, sometimes fingers aren’t long enough, or can barely reach the right spot.

Toys are also good, and there are many toys made specifically for prostate stimulation, such as the plug illustrated in When should I use buttplugs and why? Of course, that’s just one shape, and there are many. Some warm up, some vibrate. Some twirl. Some do all of those things, including sparkle, light up and move to music.

Basics are good to start with.

With a finger


Remember to go over all of the information I’ve covered so far about lubes, preparing, preparing your space and safety.

You may want to start with some play to relax yourself (or your partner). Have some nice music on, be comfortable, and have your clean-up products ready as needed.

There are two ways to reach your butthole, if you’re playing alone.

  • From the front, reaching down.
  • From the back, reaching up.

Check both positions. One might feel more natural or comfortable for you. Try laying on your back, laying on your side or even standing up. It’s all about what works for you!

Take your time getting fully inserted. The external sphincter is the one under conscious control and will let you in easily. Don’t force your way past the internal sphincter. Relax and play a bit if you’d like, until that opens up to you.

Now, if you’re playing with your front bits (or your partner’s front bits, or your partner’s playing with their front bits
), that’s all well and good to get you started.

After all, the P-Spot will swell and be much easier to find when you are aroused.

You’ll find it toward the front of the body (towards the belly). Usually, it’s about the size of a walnut and you’ll/they’ll know it when you find it. The sensation will be a clear signal.

When you’re ready to really explore the P-spot, stop other stimulation and focus on what you can make yourself feel through anal play.

When it comes to P-spot stimulation, it’s all about playing until you find what you like.

Here are a few ideas:

  • Press your finger on top of the P-spot and pull it down in a “come here” motion
  • Try a firm and direct pressure like pressing the doorbell button and releasing
  • Move your finger left to right like windshield vipers
  • Experiment by adding the second finger in there.
  • Angle your butt differently to change the way the p-spot is exposed

Stay relaxed.

Do more of what feels good and less of what doesn’t:

  • Pay attention to your body reacting
  • If you have a penis, it may or may not get hard
  • You may feel like you need to pee
  • If you have a penis, you may or may not begin leaking pre-cum
  • You may start noticing sudden PC muscle contractions
  • You may feel waves of sexual energy building up around your genitals
  • You may feel your legs and cheeks tingling
  • You may feel a little high
  • You may want to really focus on your breathing and sensation through your whole body
  • Moaning or squirming is natural and can actually heighten the sensations. Don’t be afraid to let go and really enjoy yourself

As the intensity increases, you may feel like a pressure is building. You’re creating energy that wants to go somewhere. This is your potential prostate orgasm.

When the orgasm approaches, your abdominal muscles might start shaking. The muscles in your genital region may intensively flex and relax by themselves. Waves of energy may flow up and down through your body.

It could last for 30-60 seconds or more. And with a prostate orgasm, you can go again and again and again.

This is the easiest way for those born with penises to achieve multiple orgasms.

When you’re done, just relax and experience as the pleasure recedes. Keep breathing and feel your body calming down.

Didn’t work?

Well, as I mentioned before, it’s entirely possible your finger didn’t reach the prostate.

Or, you’re/they’re just not yet ready to orgasm through prostate stimulation alone. You may want to bring genitals into the mix at this point and try that.

They’re not relaxed enough (totally understandable). Prostate orgasms usually happen when you’re relaxed, which is different from most ejaculatory orgasms through penile stimulation.

Not everyone gets it the first time, and that’s OK.

As long as you (both) had fun, that’s what matters. There’s always another time to try.

Let’s Discuss!

Have you experienced a prostate massage or milking? Have you given one? Tell us about it.

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7 Responses

    1. It’s pretty damn amazing, for sure! I love sharing this information.

      The book we have scheduled for May is all about orgasms, specifically, so keep an eye out. *smiles*

    1. YES! It’s there as a download link up there, next to MOBI and ePub. *smiles*

      We just recently added the PDF read-online feature, and we haven’t updated all of our books to that format (although we are working on it.)

        1. Could you try again, and make sure you’re logged in?

          This is the older layout, bu you should see: Link to Full Book Download: PDF | ePUB | MOBI somewhere on the page. We’ll update this in the next week or two to the new layout.

          *smiles*

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