How To Do First Time Anal

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How To Do First Time Anal
Some super crucial tips for preparing your body before butt stuff.
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Zoë Ligon is a sex educator, writer, artist, and the owner of the sex-positive online toy store Spectrum Boutique , which is based out of Detroit. She loves psychological thrillers, saunas, weed, and girthy sex toys.
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Butt stuff is an entirely different type of play from oral and vaginal sex for many reasons. Those who love anal sex are often appreciative of its highly intimate nature and the unique sensation of fullness it gives the receiver.
Almost everyone has an anus, and since the anus has a ton of highly sensitive nerve endings, it’s absolutely thrilling to try anal stimulation if you haven’t explored it before. Having said that, butt stuff should be something you choose to do — not something you do to please anyone but yourself, and certainly not something anyone can be pushy or coercive about doing with you.
While it is fun as heck when done right, there’s a whole bunch of misinformation out there about it. Because everyone deserves to have a beautiful bum experience every time, here are seven tips that will help you prepare for and then enjoy yours.
First things first: Figure out your safer-sex approach. Keep in mind that if you're not using a condom, anal sex is a higher-risk sex act , especially for the receiver. The rectum doesn't self-lubricate and its lining is more delicate than that of the vagina or mouth, meaning you’re more likely to tear something during anal than during vaginal or oral sex, and tears can allow viruses or bacteria to enter the bloodstream. HIV and hepatitis are easily spread this way because they're transmitted through blood-to-blood or semen-to-blood contact.
To minimize risk, you can use a latex condom (like this one from Sustain ) or polyisoprene condom (which is free of allergens, like the Skyn condom from Lyfestyles ) during anal sex with a penis or dildo, unless you can completely sterilize the dildo . You should also utilize dental dams during anal rimming, and nitrile gloves during manual penetration. (Of course, even if you are using a condom, many common STIs, including syphilis and herpes, can still be transmitted by skin-to-skin contact.)
If you're fluid-bonded with your partner — meaning you've chosen to stop using barrier methods, a choice that should be based on the results of comprehensive STI testing — it's still important to avoid transferring bacteria from the rectum to other parts of the body, for example the vagina. Switching from anal to vaginal sex without replacing the condom or thoroughly washing the penis or dildo can lead to a vaginal or urinary tract infection.
Your rectum is not a vaginal canal, nor is it a mouth and throat, so don't expect your anus to work like other orifices. If you’re going to be the giver of anal penetration, don’t fuck an anus like any other orifice. Not only is the rectum a canal that does not self-lubricate as the vaginal canal and mouth do, the entry is also "gated" by two — yes, two — sphincters. This means that you shouldn't dream of having anal sex without a thick water- or silicone-based lube .
It also means you've got to take it easy, at least at first. Pain is the body’s natural way of telling you to slow down or stop what you’re doing. While moments of discomfort may occur when you’re new to all the booty feelings that come with anal, sharper sensations are warning signs that something isn’t happening correctly or that you’re moving too quickly. Some folks combat this by using numbing or relaxing creams, but I urge you to avoid these at all costs. If you can’t feel pain, you won’t know when your body is telling you to stop, and you risk injury to your anal tissues.
Some people with hemorrhoids find anal too painful, but others find it can actually relieve pain (stimulating the butt draws blood to the area, which keeps circulation flowing). Again, it’s your choice whether or not to play with your butt, so if you have hemorrhoids, just do what feels right for your body.
Some people fear that anal sex is going to result in an explosion of poop. These fears are generally overblown, but it's not unusual to encounter bits of poo from time to time. Some people anally douche before doing butt stuff, but many of us don’t and it works just fine. In my opinion, it’s completely unreasonable to put your body through the douching process each time you want to do butt stuff, so unless you really love douching, there’s no need.
You can reduce your chances of encountering poop by choosing to do butt stuff when you know you’re not still digesting food. For the most part, though, you won’t see any poop unless you’re about to have a bowel movement. Feces are stored in the colon, which is where the rectum highway leads. Poop only passes through the rectum as it exits the body; otherwise, it just chills up in the colon.
If you find that longer phalluses that go inside you anally have a bit of poop at the tip when they're pulled out, that’s probably because they've entered the colon. It’s no biggie, but it is something to be aware of, and you definitely want to be more gentle the deeper you go.
Clockwise from top left : Tantus ProTouch $40 ( Shop Now )/ LifeStyles Skyn Condoms Lubricated Non-Latex $6 ( Shop Now )/ Sliquid Sassy Water-Based Anal Lube $8 to $20 ( Shop Now ) / Fun Factory Bootie Plug $35 to 45 ( Shop Now ) / Sustain Ultra Thin Condoms $14 ( Shop Now )
By now you know that lube is non-negotiable for butt play. A good sex toy, meanwhile, is an ideal tool for getting accustomed to the sensations of being anally penetrated. Even if you’re looking to achieve penetration with a penis eventually, it’s wise to start out with fingers or an anal-safe toy — and, again, so much lube .
A toy is safe to put in your butt if it has a flared base or another stopping point. That's because the rectum can suck things inside the body like a vacuum (unlike the vaginal canal, which ends with the cervix). The last thing you want is to end up in the ER with a vibrator lost up your ass.
Starting with small toys will help you become familiar with how your rectum feels as things go in and out of it so that you’re prepared for a larger thing, like a strap-on dildo or penis. For a great starter toy, check out Fun Factory's Bootie Plug (in the small size) or Tantus' ProTouch . Note: Keep in mind that you shouldn't use silicone lube with silicone toys since it can degrade the material.
While we can clench and unclench our outer sphincter consciously (try it right now), the inner sphincter cannot relax unless you are super duper chilled-out inside. If you’re the receiving partner, calm your mind, steady your breathing, and try to identify and let go of any tension you’re holding inside of your body. You or your partner should begin by slowly massaging the outer ring of the sphincter and surrounding areas until you feel the anus relax. Don’t jump the gun — you have plenty of time to get to the main event.
Your breath and mind are crucial parts of successful booty play. If you’re anxiously forcing something into your body, you’re just going to clench up more. Take deep belly breaths and let the residual tension go with every exhale. See if you can identify what I call a “tension cord” in your midsection: Some of us notice that this cord releases during the insertion process, and once it does, that's when the fun begins.
If you find yourself repeatedly tensing up, take a break and pick things back up if and when you feel ready to try again. If your partner isn’t attuned to your body's cues, it’s especially important to vocalize what does and doesn’t feel good so they can respond accordingly.
You might think that whatever you’re putting in your butt should enter head-on, perpendicular to the body, but this may actually make insertion more difficult. Approach the sphincter at a 45-degree angle to the body, and if you aren’t using your fingers as the insertable object, use an index finger to put pressure against the tip of the toy or phallus to guide it in at an angle until it “tips” in.
Once you’ve got a centimeter or so in, pay close attention to the way your body feels receiving and the way the sphincter is interacting with the insertable. If the fit feels too tight, ease out. If you feel your butt opening up and accepting what you’ve put against the entryway, slowly continue ease in. You can make subtle in-and-out motions if that feels comfortable, or slightly wiggle side-to-side to massage and relax the anus.
Anal penetration can directly stimulate the prostate if you have a penis. If you have a vagina, anal penetration can indirectly stimulate its sensitive front wall, which some call the G-spot. Both the prostate and this front wall are typically located about two to three inches inside the body on the belly side, so angle the insertable up and toward the belly at a medium-to-shallow depth to stimulate them.
Short strokes are ideal if you’re using a dildo or penis, and “come hither” or side-to-side motions work great if you're using fingers. Be sure to not prod or poke at this area, especially if you’re stimulating the prostate because it can feel incredibly uncomfortable for the receiver.
Even if you’re already familiar with "G-Spot" stimulation, you might find this new method of indirect stimulation even more delicious than stimulation via the vaginal canal (and I know many folks who prefer it, in fact). And remember that just because you're focusing on the booty doesn't mean you should neglect other parts of the body: Stimulating the clit with a hand or toy during anal penetration can make for a delightful combo.
At the end of the day, when it comes to anal sex, do what makes your body feel good. And don’t give up if your first attempt isn't immediately wonderful: This type of play can have a bit of a learning curve, so go at your own pace, communicate with your partner, and enjoy the ride.
Now, watch Rachel Bloom's delightful song about orgasms:
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In what’s been a great development for butt-enjoyers everywhere, anal sex is now a lot less taboo than it used to be. For those with penises, it can be especially enjoyable, thanks to the special little walnut-shaped mass of nerves called the prostate situated under the bladder that you can “access” if you go in through the backdoor. Sometimes referred to as the “male G-spot” the prostate can deliver next-level orgasms when it’s properly stimulated. Science is currently trying to figure out why so-called prostate orgasms feel so intense—but, frankly, the why is unimportant. Let’s focus on the how.
Even though people have been sticking various and sundry items up their b-holes for centuries—google “Moche ceramics anal sex” or “ancient Rome butt stuff”—in more recent history, it hasn’t been as common for straight men to partake. So, I talked with Sex and Relationships coach Dr. Charlie Glickman, PhD, who literally wrote the book on prostate pleasure to explain just how to enjoy this under-appreciated erogenous zone. He says the most frequently asked questions he gets from straight men are: “Will it be painful?” “Will it be messy?” and “Does this make me gay?” We’ll get into this more later, but the answers to those burning questions are: it shouldn't be , not necessarily , and no, of course not.
Dr. Glickman's first point? Remember that you’re not filming a porno. Don’t try to emulate anything you’ve seen on Pornhub! You’re just asking to get hurt, and nothing is more discouraging than a supposedly pleasurable sex act that turns painful (assuming you’re going for pleasure, that is). Plus, porn stars are people who are likely having anal sex multiple times a week. And they are prepping for it—they’re just doing so off screen.
For the best chance at a life-changing, earth-quaking orgasm, he also recommends—seriously, listen to this—experimenting with butt play solo at first. For a couple reasons: The first is that it’s an opportunity to figure out what you like at your own pace, which will help you later communicate that to your partner. The second is that you can stop immediately once something becomes painful or uncomfortable. You don't have to worry about finding the right words to avoid killing the mood or discouraging your partner from ever trying this again.
Additionally, don't try to go from 0 to 60 in the beginning. Dr. Glickman recommends getting turned on using your go-to's, the things you already know you like. Not only does arousal cause the pelvic floor to relax, making anal entry easier, but “arousal changes where things land on the pleasure/pain spectrum.” Dr. Glickman explains, “things that feel amazing during sex, might not feel as good [while] reading an email from your boss.” Noted! Once you’ve figured out what it is you like up and around your butt, you can move onto more advanced play that might involve toys, or partners, or specific kinks. Just add new components one at a time. Like the act of anal itself, it’s important to go slowly.
Ahhh, eating ass. It’s been around for ages—probably millennia; the Greeks were definitely giving rimmies. But only recently have people admitted to enjoying it. In 2015, Allison Williams and Girls got a lot of press for putting ass eating on the air and potentially more firmly on the map (although Woody Harrelson was also analingus-ing his young mistress in True Detective a year earlier, and there was a rimming scene in How to Get Away With Murder that year as well).
Rimming is a great place to start with a partner because, unlike other forms of assplay, it doesn't require much advanced preparation. Wash your ass before you ask someone to venture back there, and then relax and enjoy what’s basically an all-encompassing blow job. If you’ve ever had someone touch your perineum (the spot between your balls and butthole), you know there’s a lot of feeling back there, so make sure you don’t knee someone in the face as they make their way to your b-hole. For precisely this reason, it’s often recommended for you to be in doggy-style position while receiving. If you’re worried about hair, get waxed! I know this sounds kind of crazy but waxing your ass is fairly normal (estheticians have seen everything) and it’s nearly painless, unlike waxing the front. I know that’s hard to believe, but it’s true! And it clears the way for easier access to your little tortellini.
Remember way back in 2016 when Amber Rose strongly implied Kanye was a big fan of fingering, prompting Kanye to practically short-circuit as he vehemently tried to deny it? According to a study published in 2010, 24% of men surveyed had received anal fingering, so it’s not nearly as uncommon or taboo as Kanye apparently thinks. A step “up” from the rim job (although, also commonly seen in concert with one another, a la Simon and Garfunkel), fingering requires a bit more preparation. This is where lube comes in. (If someone’s mouth is going to be around your asshole, you can also get flavored lube for rimming to make the experience more fun.)
Like most anal experiences, the slower the better, and remember there is no such thing as too much lube. You want to work your way up to getting inside the back gate, ok? It’s going to take a lot of relaxing; you can help yourself by massaging yourself externally before heading inside. You’re not going to just lie down and get four fingers up there, so slow your roll. Worried about the mess? Get some medical gloves and throw them away when you’re done. Boom! Clean hands, full ass, can’t lose.
Vibrators are not just for people with vaginas ! You can find highly rated “prostate massagers,” on Amazon, like this one , or this one , or this one . Woo! Two-day-ship-yourself the best orgasm of your life. Not ready to make that leap? Or just not into the idea of vibration? Fair enough. It’s strongly recommended that you work your way up to putting anything in your ass anyway, so you can start with anal plugs or beads, which are a lot thinner, and go from there. Often, they come in sets meant for you to build to bigger and bigger toys. Again, lube is your best friend here, so buy some when you check out. Most online sex toy shops these days ( lelo.com , adamandeve.com , babeland.com , jackandjilladult.com ) will recommend specific lubes as you’re purchasing items, and everything comes in discreet packaging shipped right to your house.
If you’re planning on playing solo with a toy, you’ll want to avoid silicone-based lubes, which can degrade certain sex toys. Instead, pick water- or oil-based lubes, however, keep in mind that oil-based lubes ruin condoms so do not ever use them when you’re wearing one. Still not sure which one to go with? Use this guide .
Start small when you get toys. Don’t try to be a hero. Also, make sure that the first few times—or at the very least, the first time—you use a toy, that you’re in full control of the situation. I don’t mean that you’re telling your partner what to do. I mean
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