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 silicone–based 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.
R.E.A.L
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
WAYS TO CONTACT ME:
Email: Skylar@enchantrixempire.com
Skype: Skylar Sinclair
Blog: YourKinkAdvisor.com
I love how detailed this is
Thank you Cum Eater. Always happy to spread knowledge, especially about all things anal. lol
Dear Goddess Skylar, I love how detailed and artful you are in describing this. It is obvious that you have a lot of experience with this. I really enjoyed reading the article and it broadened my horizons. I have tried it several times just haven’t managed to reach orgasm yet unfortunately. I would love to experience this “sissygasm ” I crave it so much because I know it is better than a “classic” orgasm. It’s exactly as you write, relaxation is the key. If I don’t relax, it hurts. When I relax, it feels amazing. I’ve tried it for just a few minutes at first then longer and longer. I manage to relax my muscles, but I haven’t yet managed to relax internally enough to reach full orgasm. I have always tried so hard that I couldn’t quite finish.
Thank you for this article, you are really amazing!
Thank you Casandra. Have you tried locking your clit up for 7 to 10 days before doing any anal play? I also advise and realize I left this out, an enema an hour or two before anal play is helpful.
Do you watch porn while engaging in anal play? Being in a hyper aroused state while filling your pussy can be really helpful.
I haven’t really tried that, thanks for the advice Mistress Skylar. Actually if I am locked up depends on my wife, but 7 days without cumming I might try, it might be better. I need to learn to be less cramped. I actually have trouble relaxing at all even during sex. Now my wife and I don’t actually have sex at all and she doesn’t miss it much unfortunately…but that’s another problem…it’s so complicated…
Hi Skylar, what a great tutorial! Both with self-guided and partnered guided. Brilliant! I am 100% on board with you when it comes to why males need to explore that P-spot!
Granted neither of us has one, but reports are as you said “intense explosive” We all know the guys have been short-changed in the orgasm department, right? shorter duration orgasms, longer refractory period, but the playing field is LEVELED with Prostate orgasms!
You too (fella) can experience the intensity of a full deep in your deep-in-your-soul orgasm, and some even MULTIPLE with P-spot play!
Thank you for this Ms Skylar I know because of this post there are going to be more recruits to the Pleasures of Anal team soon!
Don’t lie guys, you wanna try it, right?
lol Deep down, they all want to try it. lol. It’s just a matter of when and to whom, they admit it. Thank you for the lovely compliment Mistress Erika! As I tell guys all the time, “if a man is not experienced having an anal orgasm, he is not living his best sex life.”
Ms. Skylar, I have never had an Orgasm in this manner however if anyone could give me a life-changing experience it would be you.
Well SDW i hope someday I hope you achieve that life changing experience. lol
In my case, that actually had unintended results. Me and my gf was using strap so much, after a while I quickly realized the only way I had an erection was when she used the strap
How you got there doesn’t matter. The most important part is you got there!!! As I like to say, if a guy has not experienced an anal orgasm, he’s not living his best sex life! Sounds like you definitely are!
this was super informative and I can’t wait to try out these techniques!
That’s great Daisy! Keep me updated on your progress and I look forward to another call very soon! xxx
I’ll buy toys tomorrow
Wonderful! This pleases your Goddess. xxx
I love anal play and orgasms. And since I’m only allowed to have orgasms while locked in chastity and filled with one of my anal toys, I’ve become very dependent on this type of play. It wasn’t always like this as I spent a many a year as a stroker pet. But I’ve learned to crave anal orgasms along with the little soft weenus that is kept locked away.. Thank you for writing this blog, Ms Skylar
Wes, there is nothing hotter than a guy who craves anal. It’s so incredibly sexy to me. Some guys have anal orgasms right out of the gate, while others take a bit of training.
But without a doubt, all are capable of achieving it. I will admit, I have created a few anal whores in my day. I love it when a guy is an anal virgin and I turn him into an anal whore.
It’s a great hobby. lol
Hi Goddess Skylar. Just had to keep my hands busy a wee bit more (cage and all that) and needed to comment on this post…just the right topic. This is right up my alley!
First and foremost I will admit that although I’ve had one since day one, it was a while before someone finally “pounded on the door”. It took some coaxing but I let them in.
A “hole” new world opened for me, and although not a…”sissygasm” per se, the seed was planted. Well, not really. So, I notice you list about 7 ways this could begin. There is one method I haven’t tried. But yes the rosebud release “is” a thing and it is a gas! Particularly when Mistress must point out…”good gurl”. We’re done!
It’s satisfying in a kind of frustrating way. And ain’t that the idea?
One of my strongest orgasms was coupled with a lot of edge play and denial and release only by anal play and I will never forget the creampie I had to clean up.
Anal is the most intense orgasm anyone with a prostate can experience. Edging an ass is an experience not to be missed.xxx
I will HAVE to do this. Thanks for the info. AND THANKS for our wonderful session. I LOVE submitting to you Mistress Skylar
Yes you will! I look forward to our next session soon!
Reading this blog my ass already started to throb begging for your tutelage to achieve such a powerful moment. I want nothing but an earth shattering leg shaking experience and I have no doubt you on the Goddess to help my achieve this. I can’t wait for our schedules to link up so this can be experienced!!
Mmmm yes Jeff, here’s to looking to popping your anal cherry so to speak. lol
good thing I have an entire orchard with your name on it!
Hello Ms Skylar, I’ve just found this blog and hope it’s not too late to reply. Since I’ve been exploring my feminine side I’ve stopped stroking. Although Ace I do enjoy solo play and have discovered the pleasures of anal play and sissygasms, I have a cute pink smooth curved dildo. It’s true the sensations are intense anally, even if there is no orgasm penetration is still pleasurable.
Thanks for reading this.
Marianne
Hello Marianne!
So glad you found my blog!!! I am a big fan of anal orgasms for men. I think it’s amazing you are exploring.
I hope you will check this blog often as I will be updating every Friday. I love writing about my favorite topics and sharing my thoughts on all things kinkolicious! xxx