4. “The guy I was hooking up with at the time had a huge dick so I was REALLY nervous about letting him try, but I eventually let him. He put a ton of lube on and it made it a little easier, but it still felt like my asshole was ripping. I’ve done it with guys with smaller dicks and it felt much better. Bigger is not better in terms of anal, at least in my case.” –Samantha, 28

1. Relax those booty muscles. There are a bunch of li'l muscles around your anus that can be pretty tight if you're not relaxed. And as logic follows, if those muscles and your anal sphincter are tight, inserting anything can be painful and difficult rather than pleasurable and easy. Try something like deep breathing or a relaxing massage with your partner to make sure both you and your bum muscles are sufficiently chilled out, pre-anal play.
2a : of, relating to, or characterized by the stage of psychosexual development in psychoanalytic theory that follows the oral stage and during which a child derives libidinal gratification from the expulsion and retention of the feces and conflict arises from parental demands regarding toilet training During the anal stage, from about 18 months to 3 years, the sphincter muscles become sensitive and controllable and bowel and bladder retention and elimination become a source of gratification.— David G. Myers, Psychology, 2001
8. The right lube is twice as important as it is when having vaginal sex, which is already super-important. You might have heard that too much lube takes away the friction that makes it feel good for the dude. That's bullshit. There is no such thing as too much lube, because it makes it feel slightly less like you are using your butthole as a handbag for a flashlight.
So definitely don't shame yourself, your partners, or other people for wanting to try anal or enjoying it. "There’s actually very little fecal matter in that area of the rectum and the cleanup is similar to vaginal sex," she says. "The problem is a lot of people have bad experiences when they've tried anal play, because they don't know what they're doing, so that turns them off from it. Lots of people will be surprised at how much they enjoy it if they just did it right."
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Inadequately cleaned toys can serve as a reservoir for bacterial growth and even some viral sexually transmitted infections (STIs). Using a condom with toys – even if you don’t share your toys – will reduce the risk of infections. Hepatitis C, furthermore, can survive as a miniscule drop of dried blood on a toy (or other object) for up to 3 months and become reactivated when wet. (If your eyes aren’t bulging, go back and re-read that last sentence.) (Side note: that’s why sharing cocaine straws is a very real method of Hep C transmission: cocaine causes micro-tears in the nose, leaving invisible specs of blood on the straw that harbor the virus for up to 3 months.) So instead of scrubbing your toys with a nail brush or boiling them compulsively, just use a condom and rinse them off in warm, soapy water afterwards.
That information is very necessary, but I refuse to end this on a kind of scary note. The truth is that you can have an excellent time with anal play. Or it could be the exact opposite of your thing, which is OK, too. Either way, if you keep the above information in mind, you’re way more likely to come out of the experience having explored anal sex in a safe, healthy, potentially mind-blowing way.
In a 2010 clinical review article of heterosexual anal sex, anal intercourse is used to specifically denote penile-anal penetration, and anal sex is used to denote any form of anal sexual activity. The review suggests that anal sex is exotic among the sexual practices of some heterosexuals and that "for a certain number of heterosexuals, anal intercourse is pleasurable, exciting, and perhaps considered more intimate than vaginal sex".[6]
Your man also needs to be someone who will actually follow your instructions too. If he thinks he is going to be in control and calling the shots, then you are going to have to bring him down to earth and let him know that this won’t be the case. Doing this isn’t so that you can “dominate” your man, it’s so that you get to experience the pleasures of anal sex AND NOT THE PAIN.
Asking for anal can be a bit daunting, no matter who you are. Have a one-on-one with your partner and let them know that this is something you want to try. Be honest about your feelings about it. In a healthy relationship, you should be able to discuss anything openly. Everyone wants to have a good experience. If they are into it, go ahead and get started.
You might also want to manage expectations with your partner upfront. "You can say, 'Look, I want to try this with you, but if I don’t like it then I want us to be okay with this being a one-time thing,'" Levkoff says. "It's important to own that up front. If someone says, 'Well if I really like it then I’m going to want to do it more,' then that’s an obvious sign this may not be a relationship you want to be in."

9. This is a case where shower or bathtub sex might actually be good. Usually, shower sex is bad and very hard to successfully pull off. But because relaxation is so key here, trying anal play in a place where you're more likely to feel calm and loose is helpful. Plus, if you're worried about cleanliness (which isn't a real problem, but it's an understandable concern), moving things to a place where you're already getting clean helps out.
What risk are you talking about? This is an example of why saying “all, always, every”, etc… can make you look stupid. Especially since one form of “safety measure” is abstinence… and if you follow that one I’m REALLY having trouble spotting the risk!!! Not trying to sound like an A$$, but it sounds like the biggest thing you are at risk of is a mundane sex life.
12. You're going to freak the fuck out that you're pooping but you're not. Honestly, it becomes hard to tell if you are or aren't; additionally, this Tucker Max story was not helpful for my butt sex-phobia. You're probably not gonna poop. If there's a little bit of poop, as my partner said, it's not a big deal, because "[he] asked for this." (There wasn't.)

Yet people do. “Most civilians just think they can replicate what they see in porn,” says anal pro Charlotte Sartre. “They fuck me way too rough because they only see the jackhammer fucking in the scene.” This rash anal and porn education may help to explain why, as Kinsey Institute sex researcher Debra Herbenick told me last year, “about 70 percent of American women report pain during their most recent experience of anal intercourse—quite a bit of it moderate to severe.” It may also account for anecdotal reports of increasing numbers of women suffering anal sex injuries, like tears or prolapses, often caused by overly-tense or rough play.

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I personally have just started experimenting with anal sex and from my experience, it sounds worse of a painful experience than it really is. My misconception about it, that I think a lot of other girls have too, is that the initial pain of… insertion… lasts through the entire insertion process, or in more blunt terms, that the pain you feel when a guy first inserts his penis “head” in lasts throughout the entire time he continues to push inward. This was not the case at all, for me at least. I’m not sure if that is what the term “rimming” is, but once my partner and I got past that initial step (which did take some practice and patience, as described in the article), it was smooth sailing.

It feels really good when you take a good poop, so one would imagine that's the draw for trying some anal, right? Not really, says one woman I surveyed. "I've suffered from hemorrhoids from a very young age, so I had to be very comfortable applying creams to my butthole and using suppositories. I absolutely CRINGE at the thought of how the suppository makes its way up your canal before your anus closes and swallows it whole. It gives me the heebie-jeebies — like nails on a chalkboard. So, while I really like the satisfying feeling you get when something comes out of the butt, there's just no way I can fathom a cock going in there," says Alex, from Florida.
Feast your sight on the most amazing redheads spreading their juicy ass cheeks and biting their lips with lust when taking dicks in those tight holes. Gorgeous blondes and insatiable brunettes are about to get anally lubed and fucked for massive orgasms. Massaged debutantes begging for anal sex with strangers and cuckolding wives taking it up the backdoor while their husbands watch.

If you’re using a sex toy with a partner, it’s important to have safer sex to help prevent STDs. If someone who has an STD uses a sex toy, the body fluids on that toy can spread the infection to another person who uses that toy. So wash any sex toys with mild soap and water after you use them and before they touch another person’s genitals. You can also put condoms on sex toys to keep them clean and prevent the spread of STDs — just change condoms before the toy touches another person’s genitals. And never put a sex toy that’s been in a butt into a vagina or mouth without washing it or changing the condom first. Butt germs can cause STDs and other infections.
8. The right lube is twice as important as it is when having vaginal sex, which is already super-important. You might have heard that too much lube takes away the friction that makes it feel good for the dude. That's bullshit. There is no such thing as too much lube, because it makes it feel slightly less like you are using your butthole as a handbag for a flashlight.
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