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Anal Sex Loving
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Despite there being a healthy renaissance for butt play in recent years, backdoor entry is still a deal-breaker for many women — a no-way, no-how, entirely off-limits scenario. Still, more than a third of women (36.3 percent) surveyed in a 2015 study from the Journal of Sexual Medicine reported having tried anal sex ; 13.2 percent reported having had it within the past 12 months.
For some women, like me, anal sex can be a mind-blowing addition to the bedroom . Until recently, I’d never had an orgasm from anal sex alone. Anal sex has always been a welcome precursor to vaginal penetration and other below-the-belt play. The most intense orgasms I’ve had — ever — have involved some combo of simultaneous vaginal penetration, clit stimulation, and ass play.
The key, for me, is to have a patient partner — one whom I trust. Oh, and plenty of lube. The anus isn’t self-lubricating, and the sphincter needs to be relaxed before you insert anything into it. For me to engage in anal sex, I need to be fully relaxed, lubed, and ready. And even then, sometimes the equipment isn’t, umm, compatible. Usually, I’d say you can never have too much of a good thing, but size can be an issue.
Anne Hodder, ACS, a multi-certified sex and relationships educator, says a successful anal experience is most often the result of communication, relaxation, preparation, lubrication, and (at least initially) gentle stimulation. “Anal is something you and your partner should discuss and plan for while sober and clothed,” she says. “Discuss expectations and concerns.”
Here are my top 25 tips on how to enjoy anal sex :
It needs to be a “hell yes.” Like anything in life, if the idea of anal sex doesn’t inspire an enthusiastic “hell yes” you probably shouldn’t do it. If someone has to convince you to do something, say no.
There needs to be a solid level of trust. For me, anal sex requires a higher level of trust than vaginal sex. I’ve rarely had painful vaginal penetration, but there have been a few less-than-memorable mishaps with an overzealous penis and my ass. I’m not letting a penis or strap-on get near my backside unless I trust that you’ll wield it responsibly.
If you “accidentally” slip it in, you’re an asshole. There are these concepts called consent and communication. Accidental anal is not OK.
Let go of any expectations. Instead of immediately focusing on full penetration, try to be as present as possible, and enjoy the buildup and arousal. Sometimes, it takes a few tries to make it happen. And sometimes, anatomy doesn’t fit, or it’s painful for the receiving partner.
Your butt is beautiful. If you’re going to let someone stick their dick or strap-on in your backside, you’re going to have to relax about how it looks. It may not be your most favorite body part, but the reality is that someone will be looking at it, they may be licking it, and if all goes as planned, penetrating it. All butts are beautiful.
Relax. I know, I know — this is easier said than done. If you’re nervous, take a few deep breaths. Like you mean it deep breaths. A calm mind will hopefully set your ass at ease.   
Slow and low is the tempo. I cannot emphasize this enough. Go as slow as you need. And if something doesn’t feel quite right, it’s OK to stop and start again. I’ve learned things go more smoothly the slower I go because I’m not triggered to clench or clamp down from worry or discomfort.
Start small. Instead of going for the biggest dildo in your bedside arsenal, start with something small, like a single (lubed) finger, and work your way up.
This bullet vibrator’s small and compact shape makes it a great toy to use as you start out.
Communication is key. Your partner may be fan-freaking-tastic, but they are by no means a mind reader. It helps to have a conversation before you have butt sex for the first time. And if you’re in the throes of it, if you want more or less of something, use your words and speak up.
Use silicone lube (and don’t skimp). The anus is much tighter than the vagina, and it doesn’t naturally self-lubricate like the vagina does — no matter how turned on you are. Thick, silicone lubes tend to be longer-lasting and make for a smoother sailing backdoor situation. The wetter, the better. Always.
Unless you’re using silicone toys… This is a pretty simple rule of thumb: If you’re using silicone toys, use a water-based lube, since silicone-based lubes can break down toys and make them gummy and gross (like material doesn’t like like material).
And definitely, don’t use a numbing lube. Desensitizing lubes aren’t inherently harmful, but the anus consists of thin, sensitive tissues, so tears and irritation are more prevalent. I want my body to be able to signal if something isn’t right.
Go shallow at first. Whether it’s with a toy or finger, go shallow at first when penetrating someone’s anus. I know, the impulse is to get in there — all the way in there — but take it easy, tiger, before you deep dive.
The position can make all the difference. Many positions are anal sex-friendly, and some are better than others. Doggy style, spooning, and the standard missionary position are best.
Don’t make any sudden movements. Sometimes it’s nice to add an element of surprise to your sex life, but not when you’re being penetrated anally. It’s not only painful; someone could legit get hurt.
Invest in a quality butt plug. If you’re brand new to anal play , I strongly suggest playing with a butt plug prior penetrative anal sex with a penis or strap-on dildo. (You can do this by yourself or with a partner.) It will get you used to the sensation of being “filled,” as well as help relax the sphincter.
Hot Octopuss has a ton of innovative sex toys for everyone, like this flexible butt plug that’s remote controlled for hands-free play. For beginners though we recommend this quality butt plug whose miniature size is great for beginners. The smooth, narrow tip along with its stainless steel design allows for easy and controlled penetration.
Avoid ass to mouth play (ATM). If you’re a vulva owner, the potential transfer of bacteria from the anus to the vagina should be a concern. If you are moving from anus to vagina, switch condoms, or be sure to clean your penis or strap-on thoroughly. 
Don’t overlook analingus. Before you yuck this popular yum, please know that a lot of people find having their anus licked to be a very pleasurable experience. The anus is full of all sorts of ultra-sensitive nerve endings, especially around the entry, that can get the blood flowing to all the right places.
The prostate is a magical source of pleasure. For the penetrating penis, the anus is very tight, which can feel amazing. There’s a lot of pleasure on the receiving end too, thanks to the prostate. Here’s how to find it, stimulate it, and make it super happy.
Steer clear of comparisons. Anal sex enthusiasts shouldn’t compare themselves to the porn they watch. “Keep in mind, when we make porn, we need to show actual penetration, which means we have to open up for the camera and get fucked with big things. This doesn’t always feel great,” says Lance Hart . Brooklyn Chase adds, “In porn, prep for an anal scene includes a lengthy and unpleasant routine of enemas, very little food, and anti-diarrhea medicines.”
It may be a messy event. If there’s stool in your rectum, there may be some leakage. If you’re worried, you can try to empty the pipes before sex or give yourself an enema. Seriously though, you’re sticking stuff in the superpoop highway, and stray turds are a risk you take. It’s really NBD.
A washable throw is your friend. I hate doing laundry, so if I’m going to have potentially messy sex, I pull out my washable, waterproof throw . It works perfectly on top of sheets, sofas, or any other sex-friendly surface, and can easily be thrown in the washer.
It’s OK to hit stop or pause at any point. Consent can be revoked or renegotiated at any time. A lot of people don’t understand that you can be in the middle of an act with somebody — like anal sex — and can put a full-stop on it, at any time, even if you’ve said, “Yes, I want to do this.”
If at first you don’t love anal, give it a second chance. I had some awful anal sex experiences early in my sexual career. For a while, it was off my between-the-sheets menu, and I’m damn glad I gave it a second chance. Not all penises, strap-ons, and partners are created equal, and it took me some time to find the perfect fit. I’m all for sexual agency, but sometimes, some things are worth a second glance.
A version of this story was published June 2019.
Looking for even more adventurous sex positions. Check out our bucket list for 69 (nice) options: 
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Good news: Anal sex is becoming less and less taboo. And by that, I mean GREAT news, because women can actually enjoy butt play just as much as men do. Seriously. "I've come across plenty of women who love anal play," says Gigi Engle , sex coach and sexologist (she's legit a sexpert for the Womanizer sex toy brand). Anal sex provides a different kind of fullness and can be really, truly intimate (especially if it's a first for both of you). Another major perk? Some women even experience full-on anal orgasms . With the right positions and a few helpful pointers, you could be one of them.
But if it's your first time, there’s a few things you want to keep in mind. “Go slow and go small,” says Joanna Encarnacion , a sex and relationship coach. Play around with fingers first working your way up from small to big. Start with the rim of the butthole before going all the way in with a penis, strap-on, or dildo. Remember: Lube is your absolute best friend (do NOT pass go without it) and never switch from butt to vag (because bacteria, people!).
But most importantly, don't forget to check in with yourself and your body during penetration. "There’s no shame in taking it back out and coming out of the whole situation until you’re a little bit more comfortable,” Encarnacion says.
Okay, now that that's all been covered, here are the best 15 anal sex positions to try when you're ready.
This position is perfect for people who are relatively new to anal sex because it's easy to pull off (but still hot). "Use hand play first to ease into it and see how this position works for your before slipping in the penis," Encarnacion says. Once you decide it's a go, you can control how far down you sit onto your partner, which means you can go as deep or as shallow as you like. If you're looking to spice up the position, reach your hands around the back and grab your partner for more contact. You can also simultaneously play with your own clitoris or their balls for added stimulation. "Don't be afraid to get handsy with this one," Encarnacion says.
Do It: Have your partner sit on the edge of a bed or a chair. With your back to them, slide down on top of them.
The Lying Doggy is perfect for shallow penetration—which you should definitely try if you haven't already. Most of the nerves in the anus are in the first two inches of the opening, so this is a great way to get that stimulation even if you're an anal sex beginner. Pro tip: Play around with teasing in this position. "It's great for beginners because you don't have to commit to the whole thing (literally!)," Encarnacion says. But you still get allll the stimulation. If you want more though, add a vibrator to the mix and use it on your clitoris while lying down, she suggests.
Do It: Lie on your stomach, and have your partner lie directly on top of you, entering from behind. Have them balance on their elbows for optimal comfort.
Anal sex positions are often a face-away-from-each-other kind of deal, but this one allows you and your partner to get some eye-contact in during sex. That adds to the whole intimacy thing. You can also kick things up a notch and calm your nerves with a little nipple sensation from your partner. "This will add a different sensory experience and take away some of the pressure on your mind around the anal play that's occurring," Encarnacion says.
Do It: Have your partner enter you from the missionary position. Keep your knees pressed against his side to control how deep they go, putting your hands on their chest for extra resistance. You can also add a pillow underneath your hips, to get the pelvis in the perfect place for penetration.
Don't you love that this position is called the Caboose? While it's a must-try for regular penetration, it's a really sweet one for anal. "Have them grab their hands on your ass and slowly lower you down," Encarnacion recommends. This will start the intimacy off on a high note. And once you're in the position, you'll be attached from the torso to your legs and can kiss each other to up the romance even more.
Do It: While he sits on the bed or a chair, back yourself into his lap and spoon each other while seated.
If you’re interested in standing anal sex positions, this is a great choice. It's ideal for shallow penetration, giving your nerve-rich anal opening plenty of attention. Encarnacion recommends playing around with a sex wedge or pillow to switch up the depth or direction of penetration.
Do It : Have your partner kneel against the bed and you lie across the edge, leaning on one side with your back (and obviously butt) facing them. Lean back into his penis. Swivel your hips to control the speed and motion.
Oh, spooning—the lazy girl's move for vaginal, and now anal, sex. This position is great when you don't want to make eye contact (sometimes, especially when your partner is up your backdoor, you don't want to) or feel like busting out crazy moves. Plus, skin on skin is hot. And
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