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Anal 101: How to Have the Ideal First Time

  • August 28, 2020
  • No comments
  • 5 minute read
  • Ana Salazar

We’ve all heard an amalgamation of the same anal sex horror story. It’s talked about like it’s the sexual equivalent of dropping acid for the first time. It’s unfortunate how societal norms, homophobia, and overall ignorance have built a negative stigma around it. No, anal sex will not and does not “make you gay,” and having it won’t kill you or result in a nightmarish poop fest. 

The truth is, anal sex is a practice that can be both pleasant and intimate when executed correctly. Engaging in it, especially for the first time, is a real act of trust. So, whether you need to soothe your first-time anxieties or are just looking to elevate your A-game, here’s a list of tips that have helped me enjoy anal sex to its fullest. 

  1. Plan ahead.

So, you’re ready to have anal sex. Congratulations! Anal sex isn’t for everyone, but as someone who genuinely enjoys it, I can tell you it’s allowed me to explore a part of my sexuality I didn’t know existed. My first time wasn’t ideal in the sense that I was tipsy, and we only used spit, though—please don’t be like me. Fortunately, my other times have been approached with proper caution and care, and I couldn’t be a bigger fan. I’d recommend going out of your way to familiarize yourself with your body, as well as your partner’s. Remember, there’s no point in rushing into anything, especially when it’s this delicate.

2. For the love of god, use lube.

Saliva won’t work—it’s simply not enough. Anuses differ from vaginas in their ability to stretch, so using lube is crucial. Even if you think you’re using “too much,” you probably need a bit more. I’m not kidding. Similar to anal sex, lube gets a bad rap. But I promise you, lube will make things feel a whole lot better and safer for everyone involved. If you skip the lube, you run the risk of putting you and your partner in danger by causing microtears in the anus that could make you both more prone to the transmission of STIs. Plus, trying new kinds of lube—from flavored to tingling—can be fun and memorable. 

3. This is the tip about cleanliness.

We’ve all heard the gross anal sex story that happened to someone’s older sister or roommate. The anus plays a key role in the digestive system—it’s called the back door for a reason. Even though I’ve never been the victim of one of these incidents, I understand the anxiety that can stem from them. It’s important to follow your usual shower routine, but if you’re still concerned and would like some peace of mind, it doesn’t hurt to buy a douche. While most are sold at pharmacies, it’s not hard to find them at sex shops. It should be said that douching isn’t necessary, and that your body is capable of holding things in until a bowel movement is necessary.

4. Start with butt play.

Anal sex is nothing like the content that lingers on porn sites. There’s no way that someone who has never had it can perform with such efficiency. Your first time might be a little funny and a little uncomfortable. Still, there are ways to build up endurance so that when you finally decide to go “all the way,” that pain and discomfort are barely there. A great way to start is by performing anilingus or using a finger or two. Eventually, you can move your way up to butt plugs or anal beads. Sex shops, both online and brick-and-mortar, carry a range of anal-safe products of all shapes and sizes for people of all walks of life.

5. Relax! Masturbate!

It’s completely normal to feel nervous and tense before doing anal, even if it’s not your first time. When we’re stressed, our sphincter tenses up—making anal painful and harder to execute. A perfect way to ease things up, if you’re the one being penetrated, is by masturbating with the help of a toy! I love to use my wand vibrator toward the beginning of the act to relax and tune out any discomfort. But if you don’t have access to a sex toy, oral sex, nipple play, and hands-on masturbation are all great alternatives. 

6. Be safe.

As much as I would like to, I can’t force you to wear condoms. What I will say is that, if you’re planning on not wearing one, please discuss any sexual health concerns with your partner before engaging in any sexual activity. Yes, this tip also applies to those in committed relationships. Just because it’s highly unlikely for anal sex to result in an unplanned pregnancy (believe it or not, it can happen), it doesn’t mean that you’re allowed to think of it as a “fairly safe” act. Anal sex is still a high-risk behavior for spreading STIs. These sorts of conversations can be delicate, so rather than approaching the situation with a question such as “are you clean?” Ask whoever you’re seeing “when’s the last time you got tested?” It creates an environment free of shame and patronizing feelings. If you choose to wear a condom, make sure you use a water-based lube to avoid any tearing or breakage. Oh, and if you’re planning on switching from anal to vaginal in one session, wear a new condom to prevent transferring any bacteria!

7. Don’t be a jackrabbit.

Again, anal sex is going to be significantly different from anything you’ve seen in porn or mainstream movies. Putting it in is the hardest part, but even after that’s done, you shouldn’t jump straight to rough sex. You need to allow both of your bodies to get used to the sensation, and create a steady pace from there. 

8. Clean up after yourself.

Don’t be alarmed if you see something you don’t like at the end of your session. Sure, you might not be used to it, but guess what? It’s normal. There’s no reason why you should shame or make fun of your partner for mishaps like these. If you think about it, they’re all easy to solve with the help of a shower or the washing machine. 

9. Watch out for injuries.

Let’s face it, nobody’s perfect. There’s a slight chance you might end up with a small injury, but don’t worry—it’s nothing worth freaking out about. Anal penetration can cause small tears in the anus called “fissures,” so if you see a little blood, don’t panic! You might feel some discomfort after, but the pain can be relieved with four warm 10-minute soaks in the bath per day. If the bleeding and/or pain seems excessive, please don’t hesitate to consult a medical professional. Most of these injuries can be avoided with slow-paced penetration and tons and tons of lube.

 

By Ana Salazar

Illustration by Lia Kantrowitz for Vice

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