Anal play can be exciting, intimate, and, yes, really pleasurable — but it’s not something most of us were taught how to do. If you’ve been curious (whether with a partner or solo), the best way to explore is slowly, intentionally, and with the right tools.
Dr. Evan Goldstein, the founder of Future Method and nationally renowned anal surgeon, wants you to know one thing before you start:
“Anal sex doesn’t have to hurt — and it shouldn’t. With the right education and preparation, pleasure is possible right from the beginning.”
Here’s how to dip your toe (okay, not literally) into anal play — no pressure, no rush.
Step 1: Start with you
You don’t need a partner to begin exploring. In fact, Dr. Goldstein says going solo can be the best way to figure out what feels good. There’s no performance anxiety — just you, your body, and your curiosity.
But if you want to skip the guesswork, start with an anal-specific toy made for beginners. We love the Future Method Silicone Cones because they help your muscles and your skin learn to relax, which makes things feel smoother and more comfortable later on.
“The key is preparation, patience, and listening to your body,’ he explains, “Start slow (anal dilators), focus on relaxation (correct breathing routines), and remember that pleasure is possible right from the beginning if you take the right steps.”
Step 2: Prep like a pro
According to Dr. Goldstein, using what he calls your “three D’s” is key!
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Douching – keeps you feeling fresh and confident. The Anal Douche Kit is discreet and easy to use.
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Dilation – gently teaches your body to open and relax. The Silicone Dilator Set is perfect for this.
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(Lots of) Lube – because the anus doesn’t self-lubricate! Dr. Goldstein’s go-to is silicone-based lube for its long-lasting slip.
“Silicone-based lubes last longer and are great for deeper play while water-based lubes are easy to clean and pair well with silicone toys,” he says, “Often, I recommend having both on hand, and remember: there’s no such thing as too much lube!
That’s why having Future Method and Playground’s Free Love lubricant both on hand is the dream team for all pleasure!
Step 3: Go slow, then slower
When you’re trying something new, patience is sexy. Apply plenty of lube to both your body and your toy, insert gently until you feel resistance, pause, then slowly remove.
Dr. Goldstein suggests sticking with the smallest size for a couple of weeks — even if you’re tempted to go bigger. “Slow and steady prevents injury and builds confidence,” he says.
And remember: fear is normal, but most discomfort is preventable.
“If something hurts, stop, reassess, and try again later. Over time, the fear diminishes as you learn what works for your body.”
Step 4: Pick positions that give you control
When you’re ready to bring in a partner, choose positions where you set the pace. Dr. Goldstein’s top beginner pick? Cowgirl. It lets you decide how deep, how fast, and when to stop.
“Positions where the receiving partner is in control – my favorite being cowgirl because you can control the depth and speed of penetration – help with relaxation and comfort,” he explains.
According to his research, small anal dilators, cones (or fingers if neither are available) are perfect for gradual exploration. The goal is to get accustomed to anal sensations before jumping into deeper or more advanced positions.
Step 5: Talk about everything
The best anal experiences come from open, ongoing communication. Share what feels good, check in often, and don’t be afraid to pause or stop.
“Communication is everything. Face each other at the beginning of play. Ask what feels good, check in often, and respect any signals to slow down or stop. A supportive partner helps you relax rather than pressure you,” Dr. Goldstein says, “Think of it as teamwork – pleasure increases when both people are attentive and in sync.”
Step 6: Keep it playful
Anal play isn’t a one-and-done — it’s an exploration. Some days you’ll want to go deeper, other days you may not be in the mood at all. Both are okay.
“There’s no one right way,” says Dr. Goldstein. “It’s about curiosity, communication, and creating the conditions that make pleasure possible.”
With a little prep, the right products, and plenty of patience, your first experience doesn’t have to be intimidating. It can be fun, sensual, and exactly what you want it to be.
