Hello fellow kinksters, if you have been curious about how to have an anal orgasm, you are in the right place!  Let’s take a look at what an anal orgasm actually is and then talk about how you go from anal virgin to anal pro! (um, not to be confused with a Go Pro which is something completely different lol).

What is an Anal Orgasm?


Google defines it having an anal orgasm as,  Climaxing from stimulation of your anus, which is full of sensitive nerve endings. Penis owners can experience a unique prostate orgasm from anal stimulation; anal sex stimulates the prostate, a sensitive organ commonly known as the P-spot.”   For the purposes of this post we are going to focus on orgasms that involve stimulating your prostate, by penetration.  Let me be clear guys, this is the most intense pleasure you will ever experience.  If you have not partaken in penetration,  you are missing out!

Penetration can be achieved using a butt plug,  dildo, a dildo strap on, a vibrating dildo, a fuck machine, fingers, and of course a real cock.  Many guys also experiment with other objects but we are going to focus on approved ones today.   A great starting place is solo anal masturbation.

How to have an Anal Orgasm Solo


If you have never experimented with a partner, you may want to consider solo anal play.  Many guys will start by purchasing a 3 piece butt plug kit. These generally come with a small, medium and large plug.  You will also need a good bottle of lubrication.   The anus does not get wet like a pussy does, and needs a bit of help.   I recommend using a siliconebased lubricant, this will stay with you longer than a water-based.   Butt plugs are a great way to introduce penetration to your ass.  You start small and work up over time to longer wear and the bigger butt plugs.    Do NOT attempt to wear it for a full hour the first time.  Try 15 minutes and see how you feel.  This first step helps the anus get use to initial penetration and being stretched.   Before you begin any initial anal  penetration, you MUST relax.



Once the plug is inserted experiment sitting, standing, and walking.  Discover what angles provide the most pleasure.  Remember if at anytime you feel pain remove the butt plug immediately.  It’s ok to feel stretched and even a bit uncomfortable, but if there is actual pain, you stop.   When you master insertion and being stretched, it’s time to masturbate your ass.

Begin by laying  on your back, legs up,  Spread lube between your cheeks and on the butt plug, don’t be stingy, spread it around.  Now, you can use your butt plug as a dildo to engage in anal play.  Again, try different angles, depths, and speed.  To start, many find it helpful to watch porn when first penetrating. This is a new skill you are learning, orgasming from your ass, so don’t get frustrated if it doesn’t happen right away.


Tips for reaching that orgasm


So what do you do if you are having trouble reaching orgasm from anal play?   My number one tip is to stop masturbating for 7 to 10 days.  While you are still in shock reading this, I will add in…. If you can lock that cock up in chastity during that time, all the better!  I know, I know, right now you are thinking, “But Skylar, 7-10 days without getting off????”   I promise there is method behind my madness.  When you don’t give the body a way to release and let frustration build, it can be easier to achieve an anal orgasm.  The body needs release.  If it can only get it through anal stimulation, the body often readjusts and allows the orgasm to and release to happen anally.    Remember as you play  to keep it  “R.E.A. L.”  – Relax, Ease-in, Adjust, Lubricate.




Relax.  Find a comfortable position.  Breathe, enjoy the moment and try and focus on relaxing your muscles. Touch your body, soft gentle touches, enjoy your body.

Ease-in.  Once both your hole and toy are lubricated up, you can begin to put the tip of that toy inside.  Slowly, carefully.  Feel the stretch, it feels natural, it feels good.

Adjust- Move your hips, try different positions, speeds and angles.

Lubricate – Before and during as needed.  Lubrication will keep everything sliding smooth and easy.

How to Have an Anal Orgasm with a Partner


There is nothing more exciting than achieving an orgasm with a partner.  Whether a woman is pegging you from behind with strap on dildo, or a guy is plunging deep with his real cock, playing with a partner will take your anal play to the next level.  Depending on your specific kinks, anal play can be paired to create the hottest sex on the planet.  So, maybe you are enjoy humiliation and being pegged by your female partner.  Perhaps you are a sissy and want a real cock to penetrate you.  There are so many wonderful kinks that pair well with anal play.  (I will be going into greater detail on that in another post)  Takk with your partner about your desires, you concerns, and fantasies.


A virgin ass must be penetrated slowly, allowing the anus to stretch, to open up and receive.  Add lubrication if needed, and stay connected to your partner.  Again, the principles of keeping it R.E.A.L apply here.  When it comes to adjusting, it’s really about trying different angles and positions to see what feels the best and is comfortable for both partners.   If you are being pegged, remember that your partner can’t feel what’s happening inside, and you have to make sure they know how you are feeling.  There is no shame in watching porn for first time pegging sessions.  The more aroused you are, the easier the penetration will be.

The anal orgasm can be the most intense pleasure a man will ever experience.  Every body is different and it may take time and practice for some to achieve it, but it IS achievable.

Stay tuned for more BDSM content!

Your Kink Advisor,

Goddess Skylar


Email:  Skylar@enchantrixempire.com

Skype:  Skylar Sinclair

Blog:  YourKinkAdvisor.com