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Chances are if you’re ready to turn things around in the bedroom (quite literally), the thought of anal sex has crossed your mind. Even if you’re perfectly happy in missionary, you might be curious to know exactly what it’s like out there (er, back there). You’re certainly not alone in questioning what the heck anal sex feels like—and wondering if it's territory worth exploring.
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Well, here's the deal: You'll likely think it's kinda uncomfortable the first time, says Mary Jane Minkin, M.D., clinical professor of obstetrics, gynecology and reproductive sciences at Yale School of Medicine.
"The key thing about anal sex is that more guys like it than women like it, to be honest, or at least that’s what I hear from my patients," she says. "It's uncomfortable for a lot of people, and most people will have pain. But make sure you have plenty of lubrication on hand."
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Also, if it's excruciating pain—full stop. "I don't want anyone associating sex with something painful," Minkin says. So if the lube isn't working, maybe dial it down or forego the rear sack sesh that night.

That said, anal certainly isn't a drag for all women. In fact, all it takes is scouring Reddit for some solid insight from real women on what anal sex feels like:
“I love it, especially with a larger toy or penis. At first it is very intense, overwhelming, and a bit painful, and I enjoy all of those sensations. Next, I really enjoy the moment where my body decides to accept it. I will pretty much orgasm at that moment, especially when masturbating.
"Then it feels very much like vaginal sex, lots of sensation around the outer ring, some deep-pressure sensations. Then the deep pressure starts to feel just like a G-spot sort of orgasm. It’s great with a partner who can take it slowly through the first part.” —awfullyapt
“If anal sex hurts that much you’re doing it wrong. Yeah, it’s easy to have painful anal sex, but that should be avoided. Lube, lube, lube, warm it up, work your way up from small butt plugs, then ram away. Usually it’s easy to put in a butt plug that’s small enough not to hurt, but big enough to stretch your sphincter a little and get it to relax, then it should be way easier to switch it out.” —Seesyounaked
“The pulling out is the part I enjoy the most! The rest is also pleasurable, in a way that’s similar to PIV sex, as well. But the long strokes when he pulls out is best for me.” —gadgep
“I never would’ve considered butt stuff because I had no idea it could feel good for women, too. It always seemed like it was just painful for women, and for men only the prostate made it worth it. But a bit of light teasing/play totally outside of it felt f*cking awesome, then careful fingering, etc. It took me a long time to work up to the full penetration, but by the time we got that in for the first time, I was SO EXCITED to try it because I’d realized how incredible it feels.” —anonymous
“I’m a girl who LOVES anal, and will even do anal quickies more often than PIV [penis in vagina] ones. So, the key is to use a lot of lube. And when you think you’ve used enough, use MORE.
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"In my opinion, the first few attempts at slowly pushing the penis in is a little uncomfortable. Your body has a natural reflex to push things out of there, not suck them in. So I take deep breaths and exhale while he pushes himself inside of me… I really enjoy it. I can orgasm doing it and I have an all-around great time. It feels like what it sounds like; having an object in your ass.” —IAmSexyReptar
“[I] would wager that the majority hate it because it’s painful and uncomfortable; but it’s not degrading. I only do anal for my bf. It honestly gives me no pleasure. It’s five minutes of pain and then the rest is just okay, whatever, fine, uncomfortable.” —purple_urkle_

“I must be in the minority. To me, it feels like reverse pooping and does not feel pleasurable at all. Plus it takes so much to warm up.” —butteryourmuffin69
“I know a lot of people’s opinions boil down to ‘I like it’ or ‘I don’t like it,’ but mine is actually right down the middle. It’s fine. All the emotions feel like regular sex, but then you don’t have all the pleasurable nerve endings that you do in the vagina. It’s kind of a weird feeling for me, but I don’t hate it, especially if my partner is really into it.” —flamants

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Does Anal