Getting Over the Fear of Backdoor Play

A beginner's guide to anal.

Jul 02, 2025

I will never forget the first time I had anal sex.

It was, quite literally, a pain in the ass. I felt like I was going to poop the entire time. How on earth can anyone enjoy this?

I wrote off anal like one does cold plunging. Is this even necessary?!

Besides, when it came to penetration, my vagina was taking it in just fine. Thank you.

Then one day I was reading Zachary Zane’s Boyslut, and he described orgasming from penile stimulation like driving a car when you’re 16. Very exciting, but by the time you’re 30, you’re used to it.

Anal orgasms, on the other hand, feel like you’re driving a flying car. “Do you know what never gets old? A FLYING CAR.”

That stopped me in my tracks. I mean, who doesn’t want that kind of orgasm?!

As a straight woman who used to think anal sex was just something husbands nag about, I wondered: Where was this delightful insight my whole life?? And why aren’t more women talking about it?!

Is it even possible for someone like me, who doesn’t have a prostate, to have such orgasm?

Turns out, it does.

The A-zone—located between the cervix and bladder on the front vaginal wall—is a potential source of deep, full-body pleasure. According to friends who’ve had one, it lasts longer than a clitoral orgasm and feels like a blissful buzz from head to toe.

So last week, I moderated a Sex Talks event in NYC with Dr. Evan Goldstein—THE authority on anal health. He’s an anal surgeon, heads his own practice called Bespoke Surgical and founded Future Method, the brand behind some of the best anal wellness tools on the market.

His book Butt Seriously is the ultimate guide to anal sex, and if you’re intrigued after reading this, I highly recommend ordering it.

Here’s what I learned

There are five common reasons anal sex feels painful:

Tight muscles
Thin skin
Too little lube
Lack of relaxation
Lack of education

The anus has three sphincter muscles. You can consciously control two of them (they’re the ones you squeeze to avoid a public accident). The third one—the internal sphincter—is involuntary.

So if you’re relaxed but still can’t take it, the culprit might be this inner ring.

Also, that skin back there? It's delicate. Especially for women, the tissue is thinner and prone to tearing, which is why lube isn’t optional—it’s critical.

Silicone-based lubes are ideal because they don’t disrupt your microbiome and last longer.

As Dr. Goldstein explains, “Your ass is built to respond to signaling and pressure to push from the inside out. Anal sex asks it to do the complete opposite, and in reverse order.”

That “I’m gonna poop” sensation is your brain misreading the stretch signal. And the good news is that you can train those muscles to overcome that.

The six-week booty protocol

Dr. Goldstein recommends a six-week routine using anal dilators to build up your body’s readiness. It strengthens the skin, teaches the muscles to relax on cue, and helps you get used to sensation.

It’s a bit like meditation: awkward and uncomfortable at first, but it gets easier with practice.

Here’s the short version:

Start with the smallest dilator. Add lots of silicone lube.
Insert 1.5–2 inches, or until you feel resistance. Breathe.
Hold for 3–5 seconds, then slowly remove, re-lube, and repeat.
Do 8–12 reps per set, for 2–3 sets per session, 2–3 times per week.
Every 2 weeks, move up in size if it feels good. You don’t have to use the biggest one unless that’s your goal.

You can do this lying on your side or standing. Over time, you’ll build both physical and psychological trust in your body’s ability to receive.

If you climax while doing this, that’s totally fine. Just notice how your body responds and try to stay relaxed through the waves.

And if, after all that, things still feel tight?

There are more options—from anal Botox (yes, really) to minor surgical procedures that relieve pressure and increase comfort. Dr. Goldstein assures me they’re safe, fast, and effective.

When you’re ready to invite a partner

Choose positions where you control depth and tempo. Cowgirl and reverse cowgirl are great options. Save doggy style for later, once you’ve built more trust with your body and your partner.

You can also play with angles to explore what spots hit best for you, so that you too can eventually feel like you’re driving a flying car.

While it’s common for people to use alcohol or drugs to “loosen up” before anal sex, it’s worth treading carefully.

Think of it like wearing noise-canceling headphones while walking through a crowded street—you might feel less anxious, but you’re also less attuned to danger signs. When your body’s natural signals are numbed, it’s easier to miss pain cues, which increases the risk of tearing or injury.

Whatever you explore under the influence should be something you can also enjoy—and navigate—while fully sober.

Mind over matter

Sometimes, it’s not about whether your body can—it’s whether your mind feels safe enough to try.

You might have all the physical ingredients for pleasurable anal sex: flexible skin, responsive muscles, great lube. But if you're carrying stress, cultural shame, fear of judgment, past trauma, or just too many unanswered questions, your body can instinctively shut the door before anything even begins.

That clench isn’t always about muscles—it’s about your nervous system guarding the gates.

Pleasure asks us to soften. And softening doesn’t come from forcing yourself past discomfort—it comes from feeling emotionally safe, informed, and in choice.

If you’re struggling with that internal resistance, it’s okay to take your time. And it might help to not go it alone.

In my 1:1 work, I support clients in untangling the mental knots that get in the way of pleasure—so they can approach new experiences not just with openness, but with genuine readiness.

Our bodies are capable of so much more than we’ve been told. I genuinely believe I’ve only scratched the surface of my pleasure potential.

Chances are, so have you.

If you enjoyed this, have any questions or want to share your personal experience, I’d love to hear from you by leaving a comment below.