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

By Dr. Jenn Mann
Oct 31, 2018 @ 5:15 pm
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Eva Hill

DEAR DR. JENN,

I’ve never had anal sex, but keep hearing about how great it is. My boyfriend is down to try it, even joking with me about "fifth base," and I have always been curious, but I’m nervous to go there. Can you give a first timer like me some tips? —Backdoor Bae

DEAR BACKDOOR,

You are not alone in your curiosity about anal sex. A recent study found that 46 percent of 25- to 29-year-olds have been on the receiving end, which means more women than ever are trying it. But you can’t just dive right in to booty play. Understanding how delicate the area is and educating yourself about the best way to start is crucial to having a positive and painless experience. First off, this area of the body is very sensitive because of the high concentration of nerves there, which can bring many women pleasure through touch or penetration. (Men, too; but this isn’t about them.) That said, not everyone likes to be stimulated in this area. 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 can help.

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No partner should ever pressure you into any sexual activity. Because anal sex is such a high-risk activity and a vulnerable one, it is especially important never to be pushed into trying it if really does not appeal to you. 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. And if you do like where you're headed? Well, I have all the info you need.

Safety First

Most people know that 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. Having your partner show you an up to date panel of STI tests that includes HIV can give you some peace of mind if you are in a monogamous, committed and trusting relationship.

If your main concern is pooping...

I am 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. For this reason, any kind of anal play is always best done after a shower. Some people opt to give themselves an enema before anal play in order to feel less self-conscious and reduce worry about pooping. You also may want to keep the following tips in mind:

- Try to avoid foods beforehand that can upset your stomach, or make your poop loose.

- Give yourself enough time to digest and let everything move through you, then go to the bathroom before you start your tryst. Try to empty your bowels before taking the plunge.

- FYI: More shallow penetration makes it less likely that poop will come out.

- Have a level of acceptance. When you put something in a hole where fecal matter comes out, it is likely that it will transfer to the object you have inserted. (This counts for body parts, too.)

- For the long game, work on strengthening your sphincter muscles by doing Kegels regularly.

More importantly — does it hurt?

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 and using a lot of lube can make the experience much more comfortable. Choosing positions that provide less opportunity for deep penetration, like spooning, can 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.

Your sphincter muscles have to be physically relaxed in order for this to be a pleasurable experience, which is 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.

It takes a while for your body to adjust to a penis. As Christian Grey told Anastasia in Fifty Shades Darker, when she asked about a generous size butt plug, “As an anal virgin, you don’t want to start with this.” The same could be said for a penis. Work up in size gradually and over time.

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 are ready to make it a couples activity, make sure that you start with some good foreplay. Then, he may want to 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), he must go slowly and 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.

Ready to take it to the next level?

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 in and around the tush, it is crucial to use ones that are 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. If you’re not into the toys, a healthy reach around can help you get off.

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That's pretty much all you need to know before your first go. But also, take this with you: An interesting study that examined sexual couples who reported being just as passionate years into the relationship as they had been during the first six months, found they 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.