Finding Your First Time Anal Position: Why Comfort Beats Everything Else

Finding Your First Time Anal Position: Why Comfort Beats Everything Else

Look, let's just be real for a second. The internet is filled with clinical diagrams and weirdly aggressive advice about "the best" way to try something new in the bedroom. But when it comes to picking a first time anal position, most people are actually terrified of doing it "wrong" or, worse, hurting themselves. It’s not just about physics. It’s about trust, relaxation, and honestly, a lot of high-quality lube.

The anatomy involved is literally designed to keep things in, not let them in. You’re working against a circular muscle—the external and internal sphincters—that reacts to stress by tightening up. That’s why your choice of position matters way more than you think. If you’re strained or twisted like a pretzel, your body stays on high alert. You want to be bored-level relaxed.

Why Doggy Style Is Usually a Terrible Idea at First

Most people see movies and think "doggy style" is the default. It's actually one of the hardest ways to start. When you're on all fours, you have to support your own weight. Your core is engaged. Your glutes are often firing just to keep you stable.

According to pelvic health specialists like Dr. Evan Goldstein, founder of Bespoke Surgical, the goal is "opening the gate." When you're tensed up on your hands and knees, that gate is often bolted shut. Plus, the angle in doggy style allows for very deep penetration very quickly. For a first-timer, that’s a recipe for a bad night. You need control. You need to be able to pull away or change the angle by a fraction of an inch without collapsing.


The Side-Lying Position: The Unsung Hero of Beginners

If you want the absolute best first time anal position, start on your side. Specifically, the "Spoons" position or a modified side-lying pose.

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Why? Because you can breathe.

When you lie on your side with your knees tucked slightly toward your chest, your pelvic floor naturally relaxes. You aren't holding yourself up. You aren't worried about how your stomach looks. You're just... lying there. It also allows for incredible skin-to-skin contact, which keeps the "cuddle chemicals" like oxytocin flowing. This isn't just hippie talk; oxytocin literally helps muscles relax.

How to set it up properly:

  • Lie on your left side (some people find this better for digestion/anatomy).
  • Put a pillow between your knees to keep your hips aligned.
  • Have your partner stay behind you.
  • This allows for "shallow" entry where you can feel every movement.

Taking the Lead with Missionaries and Pillows

If being on your side feels too disconnected, the classic missionary-style approach is the runner-up. But don't just lie flat. Lying flat on a mattress often tilts the pelvis in a way that makes entry difficult and "stabby."

Grab a firm pillow. Stick it under your hips.

This slight elevation—often called the "Trendelenburg position" in medical contexts, though that’s usually a bit more extreme—angles the rectum toward the navel. This aligns better with the natural curve of the colon. It also gives your partner a clear line of sight, which is vital because, frankly, they need to see what they’re doing to ensure they’re using enough lubrication.

Speaking of lube, if you aren't using a silicone-based or high-end water-based option like Sliquid or Uberlube, you're making it harder on yourself. Water-based lubes dry out. Once they dry, friction starts. Friction leads to micro-tears. Micro-tears lead to a "never again" mindset.

The "Cowgirl" Variation: Absolute Control

Some people hate being the "passive" partner during their first time. I get it. If you want to be the one in charge of the depth and speed, sitting on top is your best bet.

However, there is a catch.

Gravity is a thing. When you sit down, you’re using the full weight of your torso. For a first time anal position, this can feel overwhelming. The trick is to lean forward. Put your hands on the bed or your partner's chest. By leaning forward, you change the angle of entry and can use your leg muscles to "hover" rather than just dropping down.

Why control matters

  1. You can stop instantly if it pinches.
  2. You determine the pace of the "stretch."
  3. You can use your own hands to guide things.

Honestly, the most important "position" is actually the one you take before the main event. It’s called the "pre-game." Use a finger. Use a small toy. If you can't relax for a pinky finger, a penis or a larger toy isn't going to feel better just because you changed the way your legs are folded.

The Role of the "Internal Second"

There’s a physiological phenomenon called the "poop reflex." It’s awkward. Everyone feels it. When something enters the rectum, the nerves send a signal to the brain saying, "Hey, it’s time to go to the bathroom."

A lot of beginners panic here. They think they’ve had an "accident" and they squeeze shut.

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Don't squeeze.

A good partner will wait. They’ll stay still for about 30 to 60 seconds. This is the "settling" period. In any first time anal position, you need to give your internal sphincter time to realize that the object entering isn't a waste product and that it doesn't need to push back. Once that feeling passes—and it will pass—the actual sensation of pleasure can begin.

A Note on Safety and Real Life

Let's debunk a myth: it shouldn't "hurt at first and then get better." It should feel like pressure. Maybe a weird, full sensation. But sharp pain is a "stop" sign, not a "push through it" sign.

If you're using condoms—which you should be, especially with new partners—make sure the lube you use is compatible. Latex condoms break down with oil-based lubes (like coconut oil or Vaseline). Stick to water or silicone.

Also, the "cleanup" anxiety is real. You don't need a full medical-grade enema. A simple bowel movement and a shower are usually enough. The rectum is surprisingly clean if you've had a high-fiber diet. If you're really worried, eat some chia seeds or take a fiber supplement like Metamucil 24 hours before. It keeps everything "packaged" tightly, if you catch my drift.

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Actionable Steps for Your First Time

Don't just wing it. If you want this to be a good experience, follow these specific, non-negotiable steps:

  • The 10-Minute Rule: Do not even attempt entry until you have had at least 10 to 15 minutes of other types of foreplay. Your body needs to be in a state of high arousal, which naturally engorges the tissues and makes them more pliable.
  • The Finger Test: Use a lubricated finger first. If that feels tight or uncomfortable, no position in the world will fix the issue. Spend time here.
  • Communication Cues: Instead of saying "stop" or "go," use a scale of 1-10. "I'm at a 4 for discomfort" is much more helpful to a partner than just a generic "wait."
  • Breath Work: This sounds cheesy, but push "out" slightly with your muscles as entry happens. It’s the same motion as having a bowel movement. It sounds counterintuitive, but pushing out actually opens the sphincter. Holding your breath or pulling "in" closes it.
  • Post-Care: When you're done, don't just jump up. Stay lying down for a few minutes. You might feel a bit of "fullness" for an hour or so afterward. That’s normal.

Choosing a first time anal position is ultimately about reducing anxiety. If you feel sexy and safe on your side, stay on your side. If you feel more in control on top, do that. There is no trophy for doing the most "advanced" pose on night one. The goal is to finish the encounter feeling closer to your partner and curious about doing it again, rather than relieved that it's finally over.

Pick a spot, grab way more lube than you think you need, and keep the lights dim enough that you don't feel self-conscious. The rest is just biology and patience.