25 SUPER Honest Anal Sex Tips (From Someone Who LOVES It)

It CAN be enjoyable if done the right way.

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By Irina Gonzalez

While anal sex is definitely more out there than it used to be, it still isn't exactly mainstream yet. Despite the fact that we've been experiencing a sexual revolution of sorts over the past couple of decades and feel more comfortable discussing acts that were previously taboo, the term "anal sex" is often still met with a cringe.

Yup, war stories heard from friends have led many people to declare that hole an "exit only" zone.


But on the other hand, it seems that a ton of people are doing it: A review conducted on anal in 2010 confirmed that up to 40 percent of people have tried it at least once.

But for every female we've heard of attempting anal sex, I also know at least half a dozen women who refuse to ever do it because of some awful anecdote or another. Typically it starts with a clueless boyfriend trying to shove it in, hoping that his partner will enjoy the experience — only to have the event in in trauma and pain.

How's a girl ever supposed to give anal sex another try when it feels that bad the first time?


I've been lucky enough to have the opposite encounters with anal sex. The first time I did it was with a steady boyfriend who happened to be experienced in getting women comfortable with butt stuff. I'd even have fun, he promised. A little lube, some coaching and a lot of talking about it later, I was no longer an anal sex virgin. And I even enjoyed it!


Related: 8 Sex Positions To Do Anywhere But In Bed


Since then, it's become something that I order off the menu once in a while. Although I do have to seriously be in the mood for it, I've had plenty of orgasms during anal sex. Recently, I even had a pretty powerful orgasm with anal-only stimulation (meaning, he wasn't touching any other part of my body).

This would all be perfectly fine behind closed doors, but I was pretty shocked to see an episode of The Mindy Project with some pretty negative (and unrealistic) things to say about anal sex. In "I Slipped," Mindy's boyfriend Danny tries the surprise approach and she is, of course, shocked. When she goes to her friend Peter for advice, he gives her a few tips on sex positions — before admitting that no woman ever will enjoy butt action.


The show doesn't go on to correct this sexist remark, as Mindy has to take a heavy sedative later on to give it another try.

In light of this seriously damaging view, we decided to give you a few tips on how you actually can enjoy anal sex. And no, it doesn't make you a perv to own your sexuality.


1. Don't go straight for penetration. 

First and foremost, invest time in the foreplay. You should be highly aroused before going there, and having an orgasm (or three) beforehand never hurt either.

2. A glass of wine and romance can help.

Don't just decide to do it and go for it. While you don't want to drink so much that you get too numb, a drink or two to relax may be just what you both need.

3. Try getting to know yourself first. 

Just as with any good sex, trying something yourself first may help you relax. Try gently massaging the outer opening of your anus next time you are masturbating.

4. Yes, you might feel really naughty. 

We all know that this is a bit of a taboo subject, and it's OK to feel a bit weird, dirty or uncomfortable doing it. It's natural, but it's also 100 percent natural to experiment.


5. It's a mess. Dark sheets help. 

Yes, we're talking about your butt and things can get a little messy. If you're shy or scared, use dark sheets to keep things from getting too weird looking later.

RELATED: 10 Beyond Basic Sex Positions To Try Tonight

6. External stimulation at first. 

Just as when you tried it yourself, have your partner start by gently massaging the outside of the anus. Start slow and have him pause when you start to feel funny.

7. Be sure to stock up on lube. 

The most important part is to have good lube that you trust, and be sure to use it on both yourself and on him for maximum ease. Water-based lubricants work great.

8. The rules about using condoms. 


Yes, you must use a condom. The most important thing to keep in mind, though, is that you absolutely must switch condoms in between vaginal and anal penetration.

9. Relax, but yes it might hurt a bit. 

You're reading this because you don't want it to hurt, right? Well, I promise it'll be OK but yes, it might hurt a bit at the start. The key is to pause as you need to.

10. Get ready to take full control. 

This one is key, OK? You, ladies, are the ones that need to be in control. This is a different experience for you, and you need to gently guide him in, not the other way around.

11. Double the pleasure stimulation.

One of the surefire ways to enjoy the experience is to simultaneously be receiving, ahem, additional stimulation. Have him use his other hand to rub your clit or, once you're really into it, use a vibrator either on your clitoris or for vaginal penetration.


12. No need to get an enema or wax. 

You don't need to get an enema (ew) or get a wax back there. While you certainly can if you want to, it's not a must to enjoy the experience.

RELATED: Slow Your Roll: 8 Positions To Make Sex Last

13. Make sure you practice your breathing. 

One of the most essential things I've learned in my, well, practice is that relaxed breathing is key. When your man is about to make the grand entrance, so to speak, inhale a deep breath and then slowly breathe out as he enters.


14. Start with a position you can relax in. 

Some people prefer doggy style, and knees turned in can open the hips and take pressure off the sphincter muscle. However, many women prefer to lie flat on their backs with a pillow under the butt to start. Try whatever way makes you feel most comfortable.


15. You can try starting with sex toys

An easy way to start is by having your man start with a little penetration, either during sex or cunnilingus, using a small or bullet vibrator (turned off, if that's easier). A finger works fine, too, and should be used to stretch you out slowly before the penis gets involved.

16. Be open to having an orgasm. 

Yes, an anal sex orgasm is possible! The female cul-de-sac (the sensitive area on the lower wall of the vagina) makes one possible without other stimulation. You can also have an orgasm if you are having anal sex and he is simultaneously stimulating your clitoris or vagina.

17. What it feels like when he starts. 


Look, there's no way to put this nicely. When he begins to slide in the head of his penis, you need to exhale, relax and push out as if you are using the restroom. The pressure from his penis and the different sensations will probably make it feel, at least at first, as if you indeed are using the restroom. Relax. You're not. Your nerve endings are tricking you.

Have him stop just after the head is in, and give yourself a few minutes to get used to the discomfort and pain.

18. Eat fiber.

You'll basically feel really full. With the note above, it's probably good to mention that there is a small chance that you will have leftover feces in your anal canal. Eating a fiber-rich diet always helps, but don't be afraid if this happens. It's natural, and yes, a bit gross.


19. It's OK to start really, really slow. 

Just after he is in, have him slowly (very slowly!) rock back and forth. Allow about five to 10 minutes for your muscles to start loosening up and for that weird "wait, am I pooping?" moment to subside.

20. Remember what this is really about. 


This isn't about you fulfilling some sort of fantasy. This is about your mutual enjoyment, so focus on yourself as much as on him. He needs to understand and be patient until you're comfortable to keep going.

21. Bad experiences happen because he's too eager. 

Another reason why you need to be in control? Simply going in fast or having vigorous anal sex is exactly why women get injured and have bad experiences. If he's not good at controlling himself, lie on the side so that you can stop him with your hands and he can have easier access to stimulating your clitoris.

22. Have him talk you through the discomfort. 

It's important to keep the lines of communication open throughout this process. Make sure he is constantly checking in on how you're feeling (especially at the start) and make sure you're honest about how you're feeling.


If you've gone far enough for tonight, that's OK too. There's nothing wrong with not getting to the finish line just yet. You can try some of the early stuff, and pause. Remember, take it slow. We're not in a rush here.

23. You might need baby wipes.

Just saying. Keep baby wipes nearby in case you do have an incident with leftover feces. Have them by the bed so that he can quickly grab one and clean up when he pulls out.

24. Let him be attentive and communicative. 

You should both be communicating before, during and after the act about your feelings on it. Be open and understanding to his needs, but demand the same.

25. In the end, it's OK if it's not for you. 


But yay if it is! Give yourself points for trying something new, and don't hesitate to try it a few times if the first time you just weren't feeling it. While it may not be my favorite thing on the menu, a good time once in a while can be pure magic.