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Relationships Sex

I Finally Lost My Anal Virginity

Here’s how I gained a whole new world of pleasure


After multiple failed attempts over the last four years or so, I finally lost my anal virginity. It just happened this past weekend.

And it went well. Very well.

I didn’t even know Anal August was a thing until afterward when I started writing — but what perfect timing!

Ever since leaving a marriage where sex had become a nightmare, I’ve been on a kick of exploring my sexual self.

Escaping a mentally and sometimes sexually abusive relationship left me free to discover who I was as an independent woman. I went from associating sex with feelings of emotional turmoil to falling in love with a partner who taught me it can be pleasurable, passionate, and adventurous — when you’re with the right person.

For me, being sexually adventurous means exploring uncharted territory. Finding new and exciting ways of enhancing pleasure for my partner and myself.

One such territory is anal. But — (giggles) — no longer is butt sex uncharted for this sexual explorer. Hubby and I have successfully mapped that Wild West.

And I must say, I’d do it again.

New, different, and incredibly hot

One very important thing we had neglected during previous attempts was making sure I was truly ready to go. We’d have a little foreplay — a good bit of it focused on making him hard and ready — but not enough for me.

I think that’s the defining difference of why I was able to be fully penetrated this time: we made sure I climaxed first. Lots of kissing on my lips and on my neck. Lots of massaging my breasts and stimulating my nipples with both his tongue and fingers.

We used my vibrator that includes both G-spot and clitoral stimulation, and he watched me make myself come while he continued massaging my breasts. It was a super intense orgasm — so I was very much aroused and relaxed down there when I turned over on my belly.

Face down, ass up was the position I was comfortable trying. We started with a small butt plug first, then a bigger dildo with a base (super important with anal). It was longer than the butt plug, but still slimmer than his cock.

He inserted the toy slowly, with my clear communication for guidance on whether to keep going or not.

And this is the newest tidbit of information I found that helped me learn how to enjoy anal without hurting. Though it might seem counter-intuitive, bearing down and actually pushing out during penetration allows you to relax that ring of muscle.

That’s what I focused on with my ass in the air. We got the toy all the way in, and I used my little bullet vibrator on my clit at the same time. The sensation was different, but good. I still felt very full and stimulated, like with vaginal sex, but in a new and different place. Using the bullet vibe along with anal penetration was wonderful.

After a few minutes of the dildo, we moved to his larger, thicker cock. There was a more intense pressure, and only a tiny bit of pain at the first initial penetration. He used plenty of lube, and I again guided him with my voice. He had to go a little slower than with the dildo, but once he was all the way in, I again felt that full, pleasurable feeling.

And then he was fucking my ass. Slowly, then a little bit faster.

I was playing with my clit and being fucked in the ass for the very first time — and I was loud as hell in response to the pleasure. It was truly wild. We even managed to try a different position — he guided me down to lie flat on my stomach, his cock still inside me, and started prone-boning me with my legs closed, my muscles gripping his cock extra tight.

It felt pretty amazing.

Preparation is key

Forward planning was necessary to make it happen for me. Not just the night of, but leading up to it. Though I was always open to anal sex because my partner was interested, after a couple of failed attempts I thought maybe it just wasn’t physically possible for me.

But after plenty of time had passed since our previous attempt, I got curious again.

I wanted to know why some women enjoyed it, and I couldn’t seem to even be penetrated. The two times we tried, it was far too painful. I wasn’t relaxed or aroused enough, and my body became this impenetrable fortress that wouldn’t allow entry, no matter how I tried to make it happen.

It’s important to say that I received absolutely zero pressure from Hubby for us to keep trying. I knew the thought of it drove him crazy though. He’s an ass man, and his pleausure was indeed a motivator for me.

About a third of women say they find anal penetration pleasurable, according to a study for the National Institutes of Health, and I made it my personal mission to see if I could too. I knew there were probably some steps we had skipped and could try to incorporate, so I started doing some serious anal sex research.

I read articles and listened to sex podcasts directed toward women and couples. Some amazing and informative references that helped me in my academic anal pursuits are The 3 Best Positions for Great Anal Sex by Emma Austin, How to Make Anal Sex Less Intimidating by Demeter deLune, and the Shameless Sex podcast.

I didn’t learn until recently that you have two sets of muscle (external and internal sphincters) that need to relax and stretch open to allow entry.

“While you can control your external sphincter (skeletal muscle) consciously, the internal sphincter (smooth muscle) is not under voluntary control, and may need some additional coaxing to relax.”

Top Tips for More Pleasurable Bottoming, Jason Wong, PT, DPT

Learning this was key, because it finally hit home that I can’t just have anal sex because I will it to happen. I learned that my body needs some extra warming up, a bit of stretching with some toys, and an orgasm or two before he penetrates me.

Third time’s a charm!

Even though I thought I hated anal sex or wasn’t capable of it, I realized that for some, like me, it’s just a matter of learning about your body and knowing how to prepare. The result is discovering new pleasure zones I’d never felt before.

Here’s what I would recommend to anyone thinking of being on the receiving end of anal sex.

  1. Preparation. Confession: I have anxiety around germs and poo during sex. I don’t like the idea of getting messy back there, and it’s something that can really affect my body’s ability to relax. What helped me with this was knowing I’d gone to the bathroom that morning. I ate light that day. And, during my shower just before we fucked, I placed my finger in my bum, which assured me things were nice and tidy. Knowing this beforehand really helps if you’re an anxious gal like me.
  2. Foreplay. Lots of foreplay. I need to come before I’m penetrated. Once, at the very least. (More is better!)
  3. Lube, lube, lube. I love the feeling of it on my skin, and it’s a step you can’t skip or replace with saliva.
  4. Patience and communication. Go slow. Talk. Check in. Always be clear about what’s working and what isn’t.
  5. Understand it might not work out. And both partners need to be completely cool with it if it doesn’t. You don’t only have to give it one chance — you can try again later if you want to. Sometimes practice makes perfect!

As good as everything felt (and it felt really fucking good), neither of us got to come this first time. I had pretty much desensitized my clit from all the battery-operated stimulation I’d been giving it for a good while up to the anal sex.

And he didn’t get to come in my ass, as he sometimes will lose his erection if he waits too long to finish. So all the preparation and warm-up is absolutely necessary, but it’s going to be tricky for us to work out the timing for both of our unique bodies.

But the experience was immensely hot and has opened a whole new world of pleasure for us — so I see it as a successful new venture! I think with some practice, we’ll get the hang of it.


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