We all experience a variety of unforgettable “firsts” in our lives. That moment you met a special partner or lover. Discovering the taste of your favourite food. The first time you rode a bike. All of these moments are special in our memories and provide a happy place to revisit over and over again.
How I Enjoy Hands-Free Anal Orgasms
Sex can also provide these feelings. For some folks, sexual firsts can happen rapidly, one on top of another in a super steamy session. For others, they come slowly, perhaps through the course of a lifetime.
I’ve been fortunate enough to learn, try and experience many different sexual fantasies and activities. Many were (and continue to be) fantastic ways to explore pleasure. Of these, there have been many mind-blowing moments, but a few stand out as unbelievably awesome.
Like, I will never forget the first time I experienced a hands-free anal orgasm, with the party all in the back and no need to involve the front.
Read: 5 Rules of Anal Play for Straight Men
Even though it was 20 years ago. Even though it was a few partners ago. Even though so many different sexual adventures have happened in the meantime. The first time I had a full-on orgasm from only bum fun will remain etched in my body’s memory.
Anal pleasure has been a part of my sex life for most of my life. I discovered my backdoor at an early age and have darkened that doorstep many, many times in many, many ways.
On this particular occasion, I was playing with a partner. At that point, her fingering my ass was either a foreplay precursor to other sexytime fun to come, or leading up to her pegging my butt. I was laying back, enjoying two of her fingers in my ass. She moved from in-and-out penetration to a more concentrated prostate massage. My penis took notice.
Like some other people with penises, mine is usually flaccid when I receive anal stimulation. But then, it twitched, and twitched some more. Pre-cum was flowing and the longer she fingered me, the more I squeezed back, mini spasms overtaking my body. We knew something new was happening. In unspoken agreement, neither of us made a move on my penis as I squeezed harder and more frequently on her fingers. Despite the intense sensations, every time I got close, I didn’t think I could make it happen.
Just as I was about to give up and grab my cock for sweet relief...I felt it. Even though I still wasn’t fully hard, the rush of impending orgasm was now undeniable. It rolled throughout my body, overtaking every muscle and inch of skin. It started in my ass, radiated out and then zeroed in on my penis.
And then it happened. The explosion. The intensity. The complete, full-body release. I didn’t see the entire moment, but I managed to force my eyes open just enough to catch a couple of the spurts of ejaculate squeezing out of my cock. I’d missed much more escaping but that visual was almost as thrilling as the orgasm itself.
Read: How to Orgasm from Anal Sex
Since that moment, I made it a sexual mission to relive this anal awesomeness. It felt that damn good that I knew I’d need to experience it more—whether on my own or with a partner. Fortunately, I have had people to play with who enjoy experiencing hands-free anal orgasms as well—mine and their own. But I’ve also put in some good, hard work to make sure I can experience that sensation again and again. But when you love what you do, you’re never truly working, are you?
There’s no doubt, for me, that the most sure way to experience a hands-free anal orgasm is with another person taking control. This isn’t to say I can’t do it on my own, but my partner’s fingers are the surest way to get me off.
That said, the moment anal-focused sex toys entered my life, I knew I was hooked. The pleasure chest beside my bed will attest to the fact that sex product manufacturers have realized the potential of formerly-taboo butt stuff and are now creating toys that are specifically designed to fit in and feel great in our asses. Other toys, such as dildos and vibrators certainly feel good—don’t get me wrong—but butt plugs, (like the Satisfyer Plug-ilicious 1 and Plug-ilicious 2) and anal beads (such as Satisfyer Love Beads) designed for asses are so much better.
My current go-to for a hands-free anal orgasm is a vibrating butt plug. I won’t even say it is the next best thing to finger caresses on my prostate—it is right up there on par. I was always a little frustrated that my arms just aren’t long enough to truly finger my own ass, but finding this product took that frustration away. It is just the right size to slide in easily (with lots of lube, of course) and it curves to my prostate at the perfect angle. Just putting it in makes my penis start to drip.
Take the Quiz: Do You Know How to Pleasure a Butt?
And then I turn it on. The vibrations really are the key. Not too fast or strong at first, I like to ease into the sensation. Each time I increase or change the speed or intensity of the vibes, my penis jumps. I know I’m on my way, but it is a journey.
[Sound like something you'd like to explore? The Backdoor Lover by Satisfyer is a beginner-friendly anal toy that has powerful vibrations and a gentle curve that fits just right.]
For me, hands-free anal orgasms are great, but they don’t happen every time I try. I encounter a couple different obstacles which sometimes derail the potential. Sometimes I just run out of patience and can’t keep my hands off my cock. This isn’t really a problem, because, well, orgasm still happens!
The other issue is a matter of concentration. To have a hands-free anal orgasm, you have to concentrate and focus on those sensations. However, focusing too intently can easily lead to frustration and an inability to orgasm. My personal remedy to this is reading erotica or watching porn at the same time. These pleasure tools aren’t necessary for me to cum, but having a little something extra in the background for a bit of distraction allows me to not hyper-concentrate and allow my body to work its special magic.
Now, much of this has been focused on my experiences, as someone with a penis and a prostate. Fortunately, hands-free anal orgasms are possible for many different people across our body spectrum. Paying attention to the prostate is just one way to experience these terrific anal orgasms. Have fun exploring and creating your own memorable moment!
Jon Pressick is a sex-related media gadabout. For more than 20 years, Jon has been putting sex into our daily conversations at his long-running site SexInWords—as a writer, editor, publisher, sex toy reviewer, radio host, workshop facilitator, event producer and more. These days, he focuses on writing for Kinkly, GetMeGiddy, The Buzz and PinkPlayMags and editing Jason Armstrong's series of Solosexual books. You can find him on Twitter at @Sexinwords.