Want to Try Anal Sex for the First Time? Read This

Here's how to prepare for anal sex, according to sex and relationship expert, Dr. Jenn Mann.

SEO UPDATE/ HUMP DAY: How to Prepare for Anal Sex
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My monogamous S.O. of two years and I have been sheltering in place for a few months now... and our sex life has sheltered in place, too. Now that our stress levels have eased up a bit, we're attempting to mix things up a bit in the bedroom, and we've been talking more and more about having anal sex for the first time. We have both always been curious, but are a little intimidated — and I'm not sure how to prepare to be on the receiving end. Can you give a first-timer some tips? —Ready to Explore My Backdoor


There is no time like the present to experiment with a little black door action. It sounds like you are in a monogamous, trusting relationship, and are both on the same page about jumping in.

An interesting study found that couples who reported being just as passionate years into the relationship as they had been during the first six months were more likely to have participated in a wide variety of sexual activities, including anal stimulation. While I do not believe, as a couples therapist, that anal intercourse is the antidote to a troubled relationship, I do think that couples who are able to experiment together are more likely to feel close and connected. And anal sex is one great way to get very close, and very connected.

But especially given the current pandemic, there are a few things you need to know before you both take the plunge to have a positive and painless experience and avoid a trip to the ER (which yes, can happen). Ahead, what to know (and how to prepare) before having anal sex for the first time.

Start with communication and consent.

First, it's important to educate yourself about your own body and to understand how delicate and sensitive this area of the body is. This is because of the high concentration of nerves, which can bring many women pleasure through touch or penetration. (Men, too, if you're using an anal toy with your partner.) That said, not everyone likes to be stimulated in this area — pleasure isn't black and white. Therefore, communication and clear consent is an important part of the process, and for first-timers, taking it slow and checking in along the way is crucial.

No partner should ever pressure you into any sexual activity, anal or otherwise. Even though you are curious and willing, you always have a right to change your mind if something does not feel okay. Make sure that you and your boyfriend have clear communication before you start down this new path and make a plan for what you'll do if, in fact, you don't like it.

It's also important to be open about your sexual history since anal intercourse is a high-risk activity when it comes to HIV and other sexually transmitted infections. Using latex condoms during anal intercourse can reduce the risk. That said, condoms can break and accidents can happen. Especially for those in a newer relationship, having your partner show you an up-to-date panel of STI tests that includes HIV can give you some peace of mind.

Go to the bathroom and clean up before you get started.

Any kind of anal play is always best done after a shower. Some ladies opt to give themselves an enema before anal play to clear out the bowels in order to feel less self-conscious and reduce worry about the poop factor. You can buy these disposable enema kits at your pharmacy, but soap and water or a baby wipe should also do the trick to clean the area.

But I'm not going to lie: It is possible that you might poop during anal sex. Sometimes the stimulation to the rectal area, especially if there is stool in the rectum before you start, can increase the chances of you having a bowel movement. A little leakage is far more likely. Some other things that you can do to reduce the chance of that happening:

1. Try to empty your bowels beforehand. Make sure you give yourself enough time to digest and let everything move through you before you start your tryst.

2. Don't eat foods that will upset your stomach or make your poop lose.

3. Encourage him not to go too deep. More shallow penetration makes it less likely that poop will come out.

4. Have a level of acceptance. When you put something in a hole where poop comes out, it is likely that it will transfer to the object (aka his penis) you have inserted.

5. For the long game, you can strengthen your sphincter muscles by doing Kegels regularly.

Take things slow — and use a ton of lube.

Many people worry about pain or discomfort during anal. But, it doesn't have to be that way. Making sure you work up to your partner's penis size slowly. Using a lot of lube can make the experience much more comfortable. Choosing positions that provide less opportunity for deep penetration, like spooning, can also help. Also, picking positions that give you more control (e.g. woman or receiving partner on top) can reduce anxiety about the potential pain factor.

Having physically relaxed sphincter muscles are also a necessity for this to be a pleasurable experience and why you want to start small. Keep in mind that you have two sets of sphincter muscles. The external sphincter, which is closest to the opening, is easy to tense or relax with a little bit a conscious effort. The internal sphincter, on the other hand, does not respond to you or to commands because, like your heartbeat, it is governed by the autonomic nervous system. You cannot will these muscles to relax, but you can do things that will result in relaxation. This is important because, when a penis or object is inserted into tightly contracted muscles it will damage, tear, or bruise the area. Training your body to be relaxed during penetration is a learned skill. To master this, I recommend checking out the book How to Bottom Like a Porn Star the Ultimate Guide to Gay Sex — regardless of your sexual orientation.

Learning to receive stimulation in and around this part of the body can take some getting used to. This tends to be most successful when you are already turned on. You may want to experiment with touching yourself in the area or masturbating before experimenting with your partner. When you're ready to make it a couple's activity, make sure that you start with some good foreplay. Then, your partner can start by gently touching you around the area and at the opening. When he does eventually put his finger in (which I'd recommend as a next step), have your partner go slowly and, again, be sure to use lots of lube. This is not a self-lubricating area, so you will need to use lubricant, ideally, a silicone-based one, because it lasts longer and cuts down on reapplication.

Use anal toys to work your way up.

Anal toys can help you work your way up to your boyfriend's penis size or just provide some fun stimulation by themselves. When using toys, it's crucial to use ones that are actually meant for the butt. As an ER doctor friend of mine once said, "The butt is like a vacuum. It will suck things up there." Don't be her next ER patient. Toys should be body-safe, non-porous material with a smooth, flared base to prevent it from going too far into the anus. And if your boyfriend is inspired by anal exploration and wants to try some himself, do not share toys.

There are a plethora of fun toys to explore this new and exciting area of your body. You may want to try an anal trainer to help you train your body to accept larger size objects. Some anal beads can help you experience stimulation in the area to see if you like it. Butt plugs are a good beginner toy. They even have vibrating butt plugs that come in beginner sizes, or larger for more advanced play. Anal dildos are pretty classic. If you want to taste from the buffet to see what you like, try a sampler of anal toys. An upside to these toys is that they allow for a double-penetration situation. While your partner inserts one of them in the back door he can insert something else in the front. Or, during anal intercourse, he can use one to stimulate your clitoris.

Bottom line (no pun intended): It takes a while for your body to adjust to a toy or a penis. As Christian Grey told Anastasia in Fifty Shades Darker, when she asked about a generous-sized butt plug, "As an anal virgin, you don't want to start with this." Work up in size gradually and over time.

In Hump Day, award-winning psychotherapist and TV host Dr. Jenn Mann answers your sexiest questions — unjudged and unfiltered.

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