How To Do 5 Different Advanced Sex Positions Safely (and to Great Effect), According to Sexologists and a Gynecologist

Graphic: W+G Creative
There are so many different ways to have sex. Sexual partners can puzzle their bodies together for penis-in-vagina sex in any number of ways in different sex positions, whether in the best sex positions for cuddling or the best zodiac sex positions. There are even different sexual penetration techniques. But it can be tough to achieve a seamless fit when exploring creative sex positions. In fact, the most advanced sex positions require some extra care and support to achieve without causing anyone involved physical pain—that is, in the form of a muscle strain or a thrown-out back. (And, to be clear, we're not talking about the "hurts-so-good" kind of pain.)

Experts In This Article

To get off on the right note, it’s essential to communicate with a sexual partner first and foremost about what it is you’re planning to do, and how you’re planning to do it, especially if advanced sex positions are going to be involved.

"Sex is such a dynamic event, especially when you’re experimenting with new positions." —Christie Cobb, MD

“The key is that this is an ongoing conversation,” says gynecologist and sexual wellness expert Christie Cobb, MD. “Sex is such a dynamic event, especially when you’re experimenting with new positions. All partners should be able to convey what they’re enjoying, what doesn’t bring pleasure, and how they’re willing to adjust, as sex happens,” she says. And that fluidity encompasses consent, too, which can be given or revoked at any point of a sexual encounter—position aside.

In that vein, moving slowly into new sex positions can also help reduce the risk of an accident or injury, says sexologist Jess O’Reilly, PhD, host of the Sex With Dr. Jess podcast. “Take a moment to make sure it feels good for all involved parties before increasing speed, depth, or intensity of movement,” she says. To adequately prep your mind and body for any advanced sex positions (or, for that matter, any partnered sex positions at all), you can also employ Dr. Cobb’s B.A.R.E. checklist. This acronym stands for "bowels and bladder" (empty both beforehand), "adequate time" (get warmed up with outerplay before penetration), "rested" (ensure no involved person is over-tired before diving in), and "expectations" (share your goals as part of your pre-sex communication).

Once you’ve nailed the above, read on for expert advice on how to ace a few of the most unique, creative, and advanced sex positions out there.

How To Do 5 Advanced Sex Positions Without Risking (Undesired) Physical Pain

1. Sitting 69

An illustration of the sitting-69 sex position.

Even a quote-unquote regular 69 (a position where one partner lays on top of the other, so both can orally pleasure each other) is more advanced than you might assume, says sexologist Rebecca Alvarez Story, founder of the intimacy marketplace Bloomi. “It requires knowing your partner’s pleasure cues and being able to relax while you give oral, which can be tricky,” she says.

Looking for a more physiologically advanced version? This seated 69 position, adapted from Kama Sutra (a Sanskrit text on sexuality and intimacy) takes things up a notch. While the actual version involves one person positioned fully upside-down in a handstand, with their legs hugging either side of their partner's head, this adaptation is basically the same thing but with one partner sitting in a chair—so, there’s much less risk of falling headfirst into the ground. “Make sure you avoid hardwood floors, and that the sitting partner has a good grasp of the other partner’s waist or hips,” says Story.

2. Reverse Cow-Rider

An illustration of the reverse cow-rider sex position.

Just like it sounds, this position involves a person with a vagina riding on top of a person with a penis, but in a reverse direction—that is, facing away from, rather than toward the person with a penis. And the danger inherent to this pose is more penis-related than anything else: The partner with a vagina can “miss” and sit their pelvic bone on the head of the penis, which could cause penile trauma or fracture, says Dr. O’Reilly. “The upper partner may also lean too far forward in a way that bends the penis,” she adds.

As for how to avoid that situation? You’ll want to go heavier on the lube for this one to ensure the smoothest possible penetrative glide, and when you’re getting started, try carefully guiding entry with your hands, says Dr. O’Reilly. Slower movements will also help keep the penis from going rogue.

Bloomi: Smooth Water-Based Personal Lubricant

Photo: Bloomi
Bloomi: Smooth Water-Based Personal Lubricant — $15.00

Use plenty of this water-based lube to make it easier to get into these different advanced sex positions.

3. Ballet Dancer (aka Three-Legged Dog)

An illustration of the ballet dancer sex position.

Any standing sex position can fall into the category of advanced, just because of the necessity of having some balance to keep from tipping over. This one, which is derived from the Kama Sutra position of Tripadam, has the vagina-haver standing on one leg, while wrapping the other around the hip of the person with a penis. Once you’re bound together by p-in-v penetration, though, there’s a risk of one person losing their footing and bringing the other person down with them.

To steer clear of a timber situation, one partner can lean their body against a wall or hold onto a piece of furniture with one hand for support (while continuing to hold their partner with the other), says Dr. O'Reilly.

And remember that this position won't work if there is a major height difference, so the shorter partner should stand on something stable and sturdy to get closer to the taller partner.

4. Indrani

An illustration of the Indrani sex position.

This position from Kama Sutra involves some serious hip flexion—but can bring intense stimulation in return, if you go at it with care. The vagina-haver brings their knees to their chest, essentially opening up their body for penetration by a partner who kneels in front of them. “I like recommending this position to couples who like G-spot, P-spot, or deep stimulation,” says Story. “But the depth of the penetration could quickly become too deep and uncomfortable,” she says. Partners should check in with each other very often while doing this position to make sure there's no discomfort.

To manage both the depth of that penetration and the amount of flexion happening at the hips, the vagina-haver could slot a sex pillow (like Dame’s Pillo) under their bottom, shifting the angle to a less severe one, says Story.

Dame: Pillo Pillow

Photo: Dame/Revolve
Dame: Pillo Pillow — $95.00

Use this comfortable but supportive pillow as an extra means of bolstering your activities.

5. Missionary Split

An illustration of the missionary split sex position.

This advanced spin on an old standby does double duty as a stretch and a sex position. (Remember that note above about doing some circulation-boosting outerplay before you dive into these?) The vagina-haver will lift one leg up over the penis-haver’s shoulder while lying down, allowing for deeper penetration.

Because of the intense stretch, however, this position could very well prompt a leg cramp. While getting sufficiently warmed up beforehand (and, heck, even doing some stretching, if time allows) can make it more comfortable, you can also turn to outside support. “A thigh sling can help hold one or both legs up to decrease the amount of effort required for you to fight gravity,” says Dr. Cobb, who also recommends a sex pillow under the pelvis of the person lying down to make the angle easier to achieve.

Once you get into any of the above positions, though, it’s best not to stick around for too long, says Dr. O’Reilly. “I’d suggest making small adjustments to your positions every minute or two so that you don’t cramp up from repetitive motion,” she says. Keep checking in with your partner too as you move into various sex positions.

And, again, continue to check in with your partner on how they’re feeling once you’re both situated—because thinking something would be fun to try and actually having fun doing it can be different things. “There’s no need to try acrobatic positions if they don’t feel comfortable,” says Dr. O'Reilly. “Listen to your body, and prioritize pleasure, not a particular performance.”

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