Best Position For First Time Anal Sex

Best Position For First Time Anal Sex
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Zachary Zane
Zachary Zane is a Brooklyn-based writer, speaker, and activist whose work focuses on lifestyle, sexuality, and culture. He was formerly the digital associate editor at OUT Magazine and currently has a queer cannabis column, Puff Puff YASS, at Civilized.

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Ah, anal sex . To some, it’s considered extremely taboo, whereas to others, especially queer men, anal sex is just how you have penetrative sex. For booty lovers and those who like a particularly tight hole, anal sex can feel absolutely divine. There’s also something “naughty” about having anal sex—something arousing about doing an act that’s traditionally considered more “devious” or "taboo."
But anal sex doesn’t just feel great for the insertive partner (a.ka. the "top"); it can also feel fantastic for the partner being penetrated ( a.k.a. the "bottom" ), especially if you’re a cisgender man. That’s because cis men have prostates , which are jam-packed with sensitive nerve endings making it feel incredible when properly stimulated. Prostate orgasms actually differ from regular penile orgasms and tend to be much more full-body, meaning that the orgasm isn’t just localized to your genitals. Instead, you feel the orgasm everywhere, from your head to your toe.
But you need to find the right position in order to experience all that pleasure, for both the top and the bottom! You may think, “Oh, duh, doggy style is where it’s at." Don’t get me wrong, doggy style can be a ton of fun, but there’s so much more to anal sex than that one position. And if you don't try anything else, you might be missing out on some of the mind-blowing sensations that come with exploring your or your partner's back door.
So, if you're looking for some creative new ways to have butt sex, we've got you covered with this list of the 20 best anal sex positions that aren't doggy style. This list describes how to pull off each position from the perspective of the person doing the penetrating, but I'd like to note: All of these anal sex positions have been tried out by yours truly as both the top and the bottom.
Remember that lube is your friend for all things butt sex (and all things sex, in general). So before you test out these positions, check out our picks for the ten best lubes for anal sex . And if your partner has a vulva and wants to try penetrating you in any—or all—of these amazing anal sex positions, you might want to check out our comprehensive guide to pegging . (And hey, here are some great condom recommendations while we're at it.)
How it works: While seated in a chair (or at the end of the bed), have your partner straddle you, facing towards you, and wrap their legs around you.
Why it’s good: This is an intimate position that allows for making out, caressing, and holding. All too often, we think of “taking them from behind” for anal sex, but face-to-face positions can be very romantic.
How it works: Oh captain, my captain! Have your partner lie on their back and hold their legs up straight in a V-shape. This grants you access to the booty. Enjoy!
Why it’s good: You’ve probably figured out by now that angles are the name of the game when it comes to anal. For one, you don’t want it to hurt your dick. Two, you don’t want your dick constantly slipping out every few seconds. (I purposefully did not include positions that often cause “falling out.”) This position allows for great angles, and it’s really hard to slip out if you'er the one penetrating your partner.
How it works: Your partner starts by lying on their side. Their arms are raised above them and their legs are bent. You then wrap one of your legs around your partner’s torso, keeping the other one straight. From there, it’s simple to start anal penetration.
Why it’s good: This is the perfect position for lazy, morning anal. (Yes, that’s a thing–ask any gay man ever.) It doesn’t require a lot of work. Your limbs are intertwined. You can kiss each other's necks. It’s the perfect way to start your day.
How it works: Have you partner hop on top of you, facing the opposite direction, like it’s reverse cowgirl. Then have them lean back, planting the palms of their hands by the sides of your shoulders (or face) depending on the height of your partner.
Why it’s good: Typical reverse cowgirl is actually tough to pull off in anal because of the angle. Most penises are fairly straight when erect, so typical reverse cowgirl will pull the penis forward, which can be painful. Extended reverse cowgirl solves that problem.
How it works: To start, get into regular doggy style, meaning your partner should be on their hands and knees in front of you. You should then get on your knees behind your partner with your knees inside their legs. You then raise one of your knees to a bent position. This will automatically raise your partner’s leg on the side. Their thigh will then be resting on yours. When done correcting, it looks like your partner is a dog peeing on a fire hydrant.
Why it’s good: This position really is great for self-identified “leg men” because it feels like your partner’s legs are all over you while in this position.
How it works: Have your partner lie face down on the bed with their knees slightly bent and hips slightly raised. For comfort and to increase the angle of their hips, you can place a pillow under their lower abs. From here, enter them from behind and keep your weight off of them by propping yourself up with your arms.
Why it’s good: You can go really deep in this position, and it feels so damn good.
How it works: Sit on the bed with your legs straight. Have your partner sit on top of you. They should bend their knees on top of your thighs, then both of you can lean back, planting your palms firmly on the bed. From there, get to business.
Why it’s good: This position is different because it’s easy for both of you to work together to get the motion going as unit, instead of either you or your partner controlling the motion and speed.
How it works: While your partner’s lying on their back, have them throw their bent legs up into the air. Their legs should be slightly past shoulder-length apart, and for this pose to really work, they need to grip the soles of their feet with their hands. (This will help them with stability.)
Why it’s good: Happy Baby Pose not only allows for deeper penetration, if your partner is a vulva-owner, it’s also an ideal position to engage their clitoris too. With one hand you can stimulate their clitoris, and with your other free hand, you can hold onto them for support.
How it works: Have you partner squat down by bending their knees and leaning forward, so their hands are firmly planted on the surface in front of you. (They should look like a frog who’s about to take a leap!) Then you get on your knees behind them.
Why it’s good: Squatted positions like leapfrog and squatting cowgirl are great for anal because they allow for deep penetration, even if your partner's booty is on the bigger side.
How it works: While they’re on their back, have your partner drape their legs over your shoulders. The angle of their body should be roughly 90-degrees.
Why it’s good: The legs on shoulders position should be considered a staple, as it allows for deep anal penetration.
How it works: You slouch down far in a chair, to the point where you head is resting on top of the chair itself. Your partner then sits on top of you, riding your reverse cowgirl, with their feet firmly planted on the floor. They actually hold your legs to better angle you.
Why it’s good: There’s something weirdly arousing about being squished by your partner while you’re penetrating them.
How it works: In this staple, your partner lies on their back, and you crawl on top of them. From there, you can easily penetrate your partner's behind.
Why it’s good: It’s hot for all the reasons that P-in-V missionary is hot. It’s intimate, allowing for plenty of kissing and eye contact.
How it works: Whoever came up with the name of this position did a great job because it really just describes what you’re doing here. Your partner should be on their back, their legs completely thrown behind them, so their body is in a C-shape. You then position yourself over your partner’s booty and start “pile driving.”
Why it’s good: You are getting suuuper deep in this position.
How it works: You two sit on the bed, face-to-face and close together. Your partner is straddling you, with their legs planted next to your side or wrapped around you. Your legs are resting next to their side.
Why it’s good: This position is up close and personal. Your chests can touch. You can kiss. You can wrap your arms around your partner, holding them tightly. You'll fall in love with this position and each other.
How it works: You should be seated upright at the end of the bed. Then have your partner get into position with their hands firmly planted on the floor in front of them. Grab your partner by the hips to position them over you. This position is slightly strenuous for the bottom, but you can help them by holding most of their weight. They shouldn’t be fully supporting themselves on their hands. Their hands should only be used to steady themselves.
Why it’s good: When done correctly, this position allows for incredibly deep penetration. You can also really control their movement by moving their hips.
How it works: While you’re standing upright on the side of the bed, your partner lies on their back, but they have the legs resting on your shoulders. (Their body should be at a 90-degree angle)
Why it’s good: This is yet another position that allows for really deep penetration. Pro tip: Put a pillow under your partner’s back, so you can angle their anus upwards, more towards you.
How it works: You sit on the edge of the bed with your feet planted on the floor. Then bend back slightly, supporting your upper body on your elbows. Have you partner then sit on your lap with their back towards you. They should put their legs on the corner of the bed for support. You can hold onto your partner's hips.
Why it’s good: The person being penetrated has control in this position. They can give you a little lap dance—it’s a great way to really tease the top.
How it works: While you’re both lying on your side, effectively spooning, enter your partner.
Why it’s good: It’s easy to increase intensity in a spooning position by wrapping your arms around your partner. If for some reason you're noticing that you’re unable to penetrate as deep as you both want, try leaning away from your partner.
How it works: It’s similar to traditional cowgirl, where you’re on your back, and your partner straddles you. Only instead of having your partner’s knees besides you, they have their soles planted on the bed in a squatting position.
Why it’s good: With this position, you can grab them by the butt and thrust deep. Even though your partner’s on top, you’re still in control of the speed and motion.
How it works: Stand at the edge of a bed or desk while your partner lies back and raises their legs to their chest. Their knees are bent as if they’re doing a "bicycling" exercise. Grab their ankles and enter them.
Why it’s good: This one's also great for people who love deep penetration.

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Wicked Sensual Care Anal Jelle, 4 Ounce
You’ve explored anal play for the first time , you’ve played with a few toys , and now you’re ready to put that P in the A. Here’s your guide to everything you need to know when trying anal for the first time.
Anal sex is pretty polarizing. A lot of people love it, and a lot of people don’t even understand the temptation to try it. No one is should be forcing you to try anal, but there are a few compelling reasons to give it a go:
If your interest isn’t slightly piqued by this point, I can’t help you. But if you’re intrigued, read on!
You’ve got a butt, but (heh) the odds are that you’re probably ignoring it. Your ass has the…
Just like with any other type of sex, you have to take precautions to keep yourself safe during anal. You can’t get pregnant, but you can transmit STIs through anal sex. In fact, transmission rates are higher for anal sex than for most other sexual activities, since anal tissues are sensitive and susceptible to microtears. Use a condom unless you’re already fluid-bonded with your partner.
The hygiene factor is one of the biggest reasons people tend to shy away from anal sex. A lot of guys are worried about poo-dick (yes, that’s the official term for it). We won’t lie to you; your penis is probably going to come into contact with traces of fecal matter. But the key word here is traces . Poop slides through the rectum and anus when you’re on the toilet, but it doesn’t hang out there the rest of the day. Here are some steps you can take to keep things as clean as possible:
In the end, you’re probably way more paranoid about the cleanliness factor than necessary. Anal sex is actually pretty clean, and it’s likely that you won’t notice anything when the deed is done and you’re pulling out of anal town.
If you’re the pitcher in this scenario, it’s usually best to let the catcher take the lead with hygiene. They’re likely just as concerned about cleanliness as you are, and you don’t want to shame them by dictating how they should take care of their body.
Most anal virgins are bound to be a little nervous at first, so give yourself plenty of time to get aroused. Do the usual things you do when you’re naked together. If you’re the receiving partner, an orgasm beforehand will help your muscles relax.
Lube is non-negotiable for anal sex. Your rectum is very tight and doesn’t create lubrication on it’s own, like a vagina does, so you need lube to help things slide in properly . Lube will also prevent painful tugging and tearing of the skin. Try a silicone lube like Pjur Original Bodyglide or a water based lube like Wicked Jelle . Put lube directly on the asshole itself, and onto the penis, strap-on, or condom. Use a lot. Even if it seems like a laughable amount, it’s necessary. Trust us.
I firmly believe that lube can be a wonderful addition to any person’s sex life. But picking a lube
When it comes to penetration itself, it’s usually best to let the receiving partner be in control, at least initially. They’re the ones at risk of experiencing pain. Dictating the pace and depth of penetration will minimize pain and ease any lingering nerves. One of the best positions for first-time anal is doggystyle. It allows the receiv er to be in control of the movement, and go as slowly as possible. Plus, doggystyle helps open up that whole area back there. Side-by-side spooning (where you’re facing the same direction) is also a good beginner position, though the pitcher will have slightly more control than the catcher.
When you’re getting started, go as slow as possible. Pretend you’re actually in slow motion, and try moving at half-speed. The receiver should focus on keeping their muscles relaxed. You may feel yourself instinctively tensing up, so keep taking deep breaths and trying to release that tension. You’re putting a big thing into a small hole, so expect that there will be some discomfort (the amount will vary from person to person). Some people will experience a “hurts-so-good” type of sensation, but others might feel “bad pain” that feels sharp or stinging. If you’re unsure what kind of pain it is, err on the side of caution and ask your partner to stop and give you a moment to relax. , Don’t ever push yourself to keep going if it doesn’t feel right. Keep working your way down the shaft of the penis slowly. Don’t start thrusting in and out until you’ve achieved complete penetration, and the receiver is comfortable with moving forward.
Once you’re both feeling at ease, you can pick up the pace and start thrusting more. You want to avoid pulling all the way out and pushing back in (this can lead to pain), so try to limit thrusts to a small range of motion. Make sure to keep communicating about what feels good and what doesn’t.
Now’s also the opportunity to add more stimulation to other areas of your body. If you’re a lady catcher, get some extra clitoral stimulation going at the same time with a vibrator, your hand, or your partner’s hand. Doggystyle and side-by-side are easy positions to do this. If you’re a dude catcher, you can jack yourself off or have your partner jack you off.
Before I tell you how to find the best strap-on harness for you, let’s get one thing straight: In…
When you’re both done with your anal fun, make sure that the giver pulls out as slowly as possible. Having something that girthy exiting your anus can feel a little strange, but slowing it down will make it feel much better. Don’t be concerned if the anus doesn’t immediately return to it’s usual balloon-knot state. It’s just taken a bit of a beating, and needs some time to close back up.
Wipe yourself off with tissues, then take a trip to the bathroom to clean up more thoroughly. Even if the pitcher used a condom, it’s still a good idea to wash off with soap and water. Soap will also help take care of the lube around the catcher’s anus. Make sure not to have any other sexual contact before cleaning up. In particular, putting a penis that has just been in an anus into a vagina is a one-way ticket to a vaginal infection.
Anal sex leaves one lingering present for the receiver: lube poops. Your next bowel movement is probably going to feel like it’s sliding right out of your butt. If your partner ejaculated into your anus, it will feel even slipperier (and may look a little strange too). Farts can also feel different traveling down your lubed-up butthole. Don’t fret if you find a tiny bit of blood in your stool; anal tissues are susceptible to small tears. But if you have a lot of blood, or ongoing pain, give your doctor a call.
Anal sex is unfortunately still saddled with a bad rap, but it can be immensely pleasurable for giver and receiver alike, and can be a fun new journey to embark on together. Give butt love a chance!
This article was originally published in January 2016 and updated Nov. 13, 2020 to replace outdated links and align the content with current Lifehacker style.

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