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After Years of Hell No, I Finally Learned To Love Anal

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Antonio Canova, Reclining Naiad, 1819–24. (c) Metropolitan Museum of Art

How to prep and enjoy backdoor play.


Written by

Stacey Leigh

When I first met my partner, we bonded over being very sex-positive, with high drives, and interests in kink play. We talked about our boundaries and limits beforehand. While most of ours were very compatible, I had a few “hard no” limits.

One of mine? No anal sex.

I had tried it with partners before and it had gone horribly. They’d requested it for a special occasion, built it up, and then wanted to start with it right away. At best, my inability to relax made them anxious and the special-occasional sex ended up being no sex. At worst, we powered through and I ended up torn and bleeding.

Yet here we are, three years later, and it’s a regular part of our sex life. Here’s what changed and how I actually started liking anal sex.

It was entirely my idea.

This is probably 90% of the success, to be honest. If he would have pressured or asked or just not-so-subtly hinted how much he wanted it, I don’t think we’d be where we are now. Instead, he stayed completely within my limits and never pushed me toward it. I knew that anal was something he’d enjoyed in his past, so when I was really comfortable, I said that it was something I’d be willing to try again.

We started slow.

Especially because of bad past experiences, I had a tendency to reflexively tighten up at any touch. As much as I tried to will myself to relax, my sphincter had a mind of its own. So we started out with him just touching and rimming my anus when we played. Eventually, he used a finger and then we started using toys, small at first, and then gradually larger. I especially loved the vibrating toys for being so pleasurable that my sphincter just kind of forgot to freak out about having them inserted.

I took matters into my own hands.

Especially in the beginning, I had a tendency to sort of shotgun butt plugs right out of me. I got really self-conscious about it and worried that my partner’s bedroom wall was gonna look like a scene from Dirty Harry. My loving partner gifted me a relatively small butt plug that was thin and flared, perfect for just training my butt to relax and acclimate to a new sensation as I worked on my laptop.

I figured out cleaning on my own time.

I also had something of a hangup about cleanliness. By taking my time, I was also able to figure out exactly the art of cleaning myself out to my own satisfaction to be able to relax and enjoy it. I tried a few different things until I hit upon the one that really worked well for me. (This might be TMI, but as someone with chronic stomach issues that I suspect might be mild Crohn’s, this was a fear that bordered on panic for me.) Having the extra time to figure it out on my own was instrumental. My partner also reassured me that if the worst-case scenario happens, it happens.

I decided when we tried it.

My partner and I decided we would take as long as I needed. There was no pressure, no deadline. As it happened, we were having a lovely weekend away, we were already using butt plugs, and… I just told him to go for it. It was amazing, unexpectedly bonding, and we’ve been into it ever since.

I have ways to flag when I am open to it.

These days, I’m really into incorporating anal play into our sex life together. Because we have a weekly scheduled sex date, it’s easier for me to plan ahead and so I have control over things like diet considerations and cleaning that are going to make me more comfortable. It’s a hot part of our sex life to be able to tell him ahead of time that I’m ready to go and actively wanting it.