Lesson Bonuses—Prostate Massage & Milking

Lesson Bonuses—Prostate Massage & Milking

How-To For Singles & Couples

A finger is a good way to start—after all, you always have your fingers with you. 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, and I’ve included two of my favorite toys in the Recommendations section. Of course, those are just two options, 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.

They help us learn our bodies and each other’s bodies, and bring us closer (yes, even to ourselves).

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 main 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!

If you’re playing together, there are many options, choose what’s most comfortable for you.

  • From between the legs, face up (mentioned in earlier lessons).
  • From between the legs, to the side (mentioned in earlier lessons).
  • IP, inspection position, or doggy.
  • From between the legs, face down: Receiver lies face down, while the giver sits between their legs, usually propped up against something, like a headboard, and drapes their legs over the receiver’s legs, to give full access to the buttocks and anus.

Take your time getting fully inserted, just like you have in previous lessons.

Don’t rush it.

Even now that you’re trained for butt play and access, still, a little bit of extra time and care really increases the potential for pleasure and reduces the possibility of pain or injury.

Getting the front bits in on the action:

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/your receiver 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 wipers.
  • Experiment by adding the second finger in there.
  • Angle your butt differently to change the way 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 flesh dick, 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/your receiver may feel like a pressure is building. You’re creating energy that wants to go somewhere. This is a potential prostate orgasm.

When the orgasm approaches, your/your receiver’s abdominal muscles might start shaking. The muscles in your/their genital region may intensively flex and relax by themselves. Waves of energy may flow up and down through your/their 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. Try a toy.

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.

Not enough relaxation (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!

Did it work? It doesn’t always the first time, or even the tenth time.

It’s funny the way our brains work. Sometimes they have to get used to the idea of pleasure from a new experience before they can really get into it.

As long as you enjoyed yourself, and you’re willing to keep at it, that’s what matters.

Do you have any tips or ideas to share with others?

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When Good People Snap

I spent 22 years working with dogs as an enthusiastic amateur dog trainer. I worked in obedience, Rally, Agility, showing, rescue and rehab. I did

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