Anal Sex Tips for Beginners - How to Have Anal Sex
Anal sex is truly a gift from the gods. Upon human creation, they benevolently placed tons of sensitive nerve endings both in and outside our anus, and when pleasured correctly, anal sex can bring our pleasure to new heights.
In my book, Boyslut: A Memoir and Manifesto, I describe my epiphany upon first discovering anal sex (and prostate stimulation) with my girlfriend, and I think it’s very appropriate to share:
“For me, orgasming from strictly penile stimulation is like driving a car when you turn sixteen. It’s cool and exciting! You’re driving a fucking car. You can go places you couldn’t go before. You have freedom. Yay! But by the time you’re thirty, driving a car isn’t as cool as it used to be. Yes, you can have some fun drives on the open road, but it’s not as exhilarating as when you were sixteen.
When you orgasm with a finger, vibrating prostate massager, or dick in your rear end, it’s like learning your car had wings. You could have been flying this whole time. Do you know what never gets old? A FLYING CAR.”
The thing is, there is no driver’s ed for a flying car. (TBH, there isn’t great sex ed in America when it comes to driving a regular car, either). In fact, only 18 states require sex education taught in schools to be medically accurate.
So there are a lot of misconceptions about anal play. In this piece, we not only break down this misinformation but also provide tips from experts on how to try anal sex safely and make sure it’s pleasurable.
Let’s get to the bottom of it, shall we? (See what I did there.)
What is anal sex?
Anal sex is often seen as just a penis going into an anal canal, but actually, anal sex can be any act of pleasure involving the anal canal or anal opening, explains queer sex educator Gabrielle Kassel. “So, analingus [AKA eating ass, tossing salad, rimming], anal fingering, pegging, penis-in-anus, prostate stimulation, double-penetration, and more all qualify as anal sex!”
Why does anal sex feel good?
Then, of course, there are psychological factors in addition to physical ones. Even in 2024, anal sex is taboo for straight couples. (It’s not nearly as stigmatized or “taboo” among gay/bisexual men because it’s pretty much the only way most cis men can engage in penetrative sex.) So for straight folks, anal sex is considered “naughty” or “slutty,” and that is, simply put, hot! It’s psychologically arousing to do something that’s deemed deviant by the rest of mainstream society.
Prostate orgasms
If you have a prostate, when you ejaculate with a butt plug, dildo, anal beads, or penis inside your rear end, you might shoot a lot more ejaculate, and your orgasm may feel far more powerful. But you can also have a separate prostate orgasm.
The prostate, also known as the male G-spot or P-spot, is a walnut-shaped gland located roughly 2-3 inches inside the rectum, towards the stomach of people assigned male at birth. It produces seminal fluid, or the fluid that mixes with sperm to create semen.
Once your anus is relaxed and ready, have your partner crook their finger forward as if they’re making a “come hither” motion, and they should be able to feel the prostate through the wall of your rectum. It'll feel different than the surrounding areas, and you (or your partner) will probably be able to tell when it’s being touched.
Does liking anal sex make me gay or “less of a man?”
As the resident sex columnist at Men’s Health, I have a lot of female partners writing in, worried that their boyfriend or husband is closeted because they want to be pegged (i.e., fucked with a strap-on in the booty).
I have to reassure these women that sex acts don’t have sexual orientations—people do. And it just feels DAMN good to get your prostate stimulated because of all those nerve endings and the feeling of “fullness” you receive when you have something inside your booty.
“The only thing that defines someone’s sexual orientation is that person claiming or naming that sexuality!” Kassel echoes.
Preparing for anal sex
The biggest reason people shy away from anal play? A fear of poop. This fear is understandable, and I’m not going to lie: shit happens, literally. The first time it happens, you may freak out and be embarrassed. By the tenth time, it’s really not a big deal. It’s like, what the heck did you expect to happen? If you’re constantly rolling around in the mud, you’re bound to get a little dirty.
Hygiene before play
“Most people douche or clean out prior to anal play,” Goldstein says. There are actually a couple of ways to douche, but the most common way involves using a little bulb where you squeeze water into your anus (through a nozzle) and then let it out. However, Goldstein warns that most people overdouche because they want to be “super clean,” but that actually can make things messier.
The key is making sure you have enough fiber in your diet, which may mean you take daily fiber pills. This will keep your bowel movements steady and decrease the amount of time you need to douche, Goldstein explains. (Don’t have a douche? Get one here!)
Anal training
In addition to hygiene, you may want to engage in what’s commonly referred to as “anal training.” Essentially, you use anal dilators (which are essentially just various-sized butt plugs) to learn to relax your anus. Anal training (dilation) kits often come with three to five dilators (toys), and you start by using the smallest one and slowly work your way up to the biggest one. The anal opening will stretch over time with patience, practice, and lots of lube. (More on this momentarily.)
Top tips during anal sex
There are a few KEY things to think about when having penetrative anal sex (aka the “dos” of anal sex).
First and foremost, there is no goddamn rush. There is this misnomer that anal sex should be painful, but that is not true! “Pain is the body’s way of communicating that something is up,” Kassel says. So, when you experience pain, it is your body’s way of asking that you pause, take inventory of what is going down, and adjust as necessary. (In other words, slow TF down!)
“In some cases, that may mean adding more store-bought lubricant, but it may also mean downsizing to a smaller penetrative device, incorporating relaxation techniques and skills, and otherwise communicating about what you like,” Kassel adds.
That said, there is a big difference between pain and discomfort. This is a new sensation you’re experiencing, and no one is born a pro bottom. (FYI, a “bottom” is the person getting penetrated, and a “top” is the person doing the penetrating.) So, you may feel a little uncomfortable, especially if you’re learning how to breathe and relax. That’s okay! Sharp and shooting pains? Nope, that means something is wrong. Typically, after the third or fourth time you bottom, you’ll start to get the hang of it, and there will be far less discomfort and far more pleasure.
Lube up
This actually leads us to the second key thing about anal sex: LUBE IS MANDATORY. Spit does not cut it. The anus, unlike the vagina, is NOT self-lubricating, which is why Goldstein recommends silicone lube for anal, which is slicker and lasts longer than water-based lube. The only thing to note is that you cannot use a silicone lube with silicone toys because the lube will erode (and eventually destroy) the toy. So you’ll need to use water-based lube in that case. (Conversely, you can use a glass or metal anal toy and use a silicone lube then.)
Remember to breathe
Third, learn to use your breath. As humans, when we’re anxious and/or in discomfort, we tend to stop breathing and start clenching. This is not good! You need to be relaxed and open up, so make sure to keep taking deep, diaphragmatic belly breaths when engaging in anal play and fight the urge to clench.
Keep communicating
Last but not least, the fourth crucial element to having a fun time with anal play is communication. You should not be lying there in silence when your partner has their fingers, penis, or dildo up your booty. Tell them to slow down or to repeat something that feels good. Tell them to “just hold it there” or to “add more lube.” Remember, your partner is not a mind reader; you gotta help them out.
The don’ts of anal sex
Additionally, don’t skip foreplay! “Whether that’s introducing toys and dilators into play, making out, exploring other erogenous zones, or engaging in oral sex and rimming, these can all help ease the mind and relax the body before penetration,” Goldstein says.
Lastly, don’t forget to cut and file down your nails. You don’t want to scratch the inner linings of your anus during anal sex, so if you (or your partners) are sticking fingers inside of an anus, cut and file those nails down! Add a glove to make it even smoother.
Best sex positions for anal sex
Everyone has preferences when it comes to their favorite anal sex positions. So, try out a bunch and see which ones you like. That said, Goldstein is a big advocate for the bottom (receiving partner) starting on top in cowboy/cowgirl/cowabunga. “This allows the bottom to be in full control of the depth and speed of penetration, as well as easily communicate with their partner.”
When warmed up, you can switch to the crowd favorite, doggy style. But starting in doggy is a little more challenging. As Good Vibes sexologist Carol Queen points out, if the bottom can’t relax, it will affect their ability to relax the butt muscles specifically.
Breaking down common anal sex toys
I’ve discussed them briefly, but anal sex toys are your best friend, and there are a few options to use when it comes to anal play—the big four include butt plugs, prostate massagers, anal beads, and dildos.
Butt plugs
Butt plugs are typically teardrop-shaped sex toys designed to be inserted into your behind. You need to make sure to use a butt plug that has a flared base (or another way of stopping the toy from getting completely sucked up into your behind, such as a string attached to the end of it). This is true for anything you insert into your ass, not just sex toys. Otherwise, you may end up having a very awkward emergency room visit.
Prostate massagers
Prostate massagers are pretty similar to butt plugs, but they’re often a little bit smaller. That’s because, if you remember, the prostate is located two to three inches inside the rectum, so you don’t need a 6-inch butt plug to stimulate it. (Though you can get way smaller butt plugs than that.) They often have a more bulbous head than a butt plug, and that’s because it’s designed to hit the prostate better.
Anal beads
Anal beads look similar to rosary beads, only they’re larger (and you stick them up your butt, not pray with them, though I suppose you could pray with them inside you). Some anal beads have beads (or balls) the same size, whereas other anal beads progressively get larger. Unlike a butt plug or prostate massager, which is designed to sit and rest inside your anal cavity, anal beads feel pleasurable when you “pop” each out of your ass one by one.
Anal dildos
Dildos aren’t specifically designed for butts like the other three toys on the list. Some are designed more for vaginal use but can feel incredible inside your booty, too. They’re phallic-shaped sex toys that are designed to be inserted and removed from the ass. Some dildos look very human-like, whereas there are also alien dildos as well as more neutral shapes.
The importance of sexual aftercare
When you’re finished having anal sex with a partner, engage in sexual aftercare. Anal sex, especially the first few times you try it, is a very intense deal, especially for people (i.e., cis men) who’ve never had anything inside of them before. So cuddle your partner, grab them water, and ask what they need after sex. Don’t just immediately get up and wash off, even though that might be your first instinct.
How to clean up once finished
If you’re using sex toys, you need to clean them every single time after use. Use toy cleaners if you like the idea of a special product for your butt plugs or just use regular, fragrance-free soap and warm water, and you’re good to go! Besides that, you may want to shower (and, if necessary, change your sheets), but that’s really it!
