What Makes Anal Sex Pleasurable + Why You Should Bring it into Your Sex Life

Though not everyone is interested in trying anal sex, we are going to venture to say that most people have had their curiosities. The thing is because anal is still dancing on the oh-so-thin line of taboo (dependant on who you talk to), it’s not something that everyone is comfortable asking questions about; and, in most cases, what feels mysterious or confusing to us can seem scary. We get it, anal sex is may seem kind of weird when you really think about it, but so are all types of sex if we’re going down that path!

Anal has the potential to feel really good for both parties, and if it’s something you often find yourself thinking about, it might just be worth a try (with a consenting, equally interested partner, of course).

The more information we have about something, the more freely we can experience it. With knowledge comes comfort, safety, ease of mind, and maybe some room for excitement! So, who do we go to when we want to learn about sexual acts? Likely friends or peers who have experienced them. Though hearing about other individual’s first-hand experiences can be incredibly beneficial, it is also important to understand that your friends aren’t medical health professionals (unless of course, they are), and just because they’ve done something doesn’t mean they know how to do it safely, properly, or in the way that’s best for you. So, in an effort to help you make an informed decision about trying anal or not, or to ensure you’re using the best practices during your current anal endeavors, we’ve consulted a professional: Dr. Evan Goldstein.

Not Your Average Doctor

Dr. Evan Goldstein is a particularly remarkable individual as he has fused together the medical word with the world of activism, inclusion, sex positivity, and so much more. We were delighted to learn about Dr.Goldstein’s practice, Bespoke Surgical, and all that he does, and we could not be more pleased to share his story with you.

Dr. Goldstein is the founder and CEO of Bespoke Surgical, a practice which specializes in gay men’s sexual health and wellness. Goldstein seeks to destigmatize gay sexuality and sexual health while spreading education and awareness among both the heterosexual and homosexual communities. You can find Dr. Goldstein featured as The Advocate’s Sexual Health Expert, in Gays With Kids, Vice, Out, and Refinery29. Additionally, he is an active member of the LGBTQ+ community supporting organizations such as the Human Rights Campaign (HRC), Callen-Lorde Community Health Center, AIDS Community Research Initiative of America (ACRIA), and Gay, Lesbian and Straight Education Network (GLESN).

Dr. Goldstein is passionate, innovative, fearless, and so very important to his community and humanity in general. Sex positivity means accepting and celebrating ALL types of sex for ALL types of individuals, sex isn’t one thing, love isn’t one thing, so we shouldn’t treat them as such. Everyone needs resources and spaces which cater to them and their needs, and we adore all that Dr. Goldstein has done and continues to do for the LGBTQ+ community.

All this said, anal sex is not specific to the gay community by any means, it can be enjoyed by anyone. So, no matter your gender or sexual orientation, if you’re interested in learning more about anal sex or perhaps trying it in the future, the below information is for you! If you’d like to hear Dr. Goldstein’s first-hand advice regarding anal sex, keep reading!

Why Anal?

First and foremost, what’s the draw? If you’ve never tried anal, your first thought might be “ew, that’s gross” or “why would I want to do that?” and we totally get it. At first thought, it does seem a little different, but if it’s practiced properly (as per the below guidelines), there’s nothing weird about it! Also, we’re human beings, and when human beings find something that feels good, we do it again. Think about all forms of stimulus, if something tastes good, we’ll eat more of it, for example. So, we think it’s obvious that people are gaining pleasure from anal sex and this is why it’s being practiced more and more. But, let’s hear it from a doctor. When asked why anal sex can be pleasurable, Dr. Goldstein shared the following insight:

DR GOLDSTEIN: Where there is skin, there is sensitivity. And where there is sensitivity, there can be immense pleasure. The relaxation of musculature and the acceptance of one’s partner’s overall length and girth not only provides localized and systemic stimulation but by milking and penetrating the prostate glands, one builds onto an already elevated orgasm. These enhanced pleasures may take time to build, since some experience initial urgency and discomfort. But with practice, dilation, and patience, one’s overall acceptance of the practice will improve. If not, we at Bespoke Surgical have Botox and pelvic floor manipulations to assist. 

THE Talk

As we’ve mentioned before, sexual communication is beyond important, especially when it comes to new partners or new sexual acts. Needless to say, if you or your partner are embarking upon anal sex for the first time, some words need to be exchanged. We asked Dr. Goldstein about the important topics to discuss with a partner prior to engaging in anal sex.

The key is to risk assess oneself, assuming that the other sexual partner is not going to disclose any of their related issues. With that said, minimizing HIV exposures through PrEP and condom usage, or if HIV+, using TasP and making sure one’s viral load is undetectable. Also, getting the HPV vaccine, if applicable, even if over the age of 26. Most people are not high-risk HPV positive and can benefit from this protection. Also, HSV and whether on suppressive Valtrex or if going to be a high-risk exposure, one may take preventatively to minimize risk. 

In a perfect world, honesty always wins and understanding one’s partner’s HIV, HPV, HSV, and other STD status would be ideal. Also, establishing whether one’s partner wants to engage with or without protection, will provide a better understanding of exposure and risk. 

The other questions are related more to sexual experience and making sure everyone is meeting each other’s expectations, specifically in the beginning stages of intimacy. The initial set of engagements has a higher risk of injury, so having a full understanding of everyone’s sexual “level” not only gives clear guidance but also allows for room for growth (cock and all)!

And finally, what is everyone’s expectation in this intimacy? Upfront understanding allows for proper risk-adjusted engagement and good old fashioned fucking fun!

Always Be Prepared

Though it may sound silly, anal sex actually requires some preparation from both parties, mental and physical. Though, the preparation process is different for the top and for the bottom (obvi). Here’s what Dr. Goldstein had to say in terms of preparation:

For the bottom:

There are both mental and physical preparations that should be made, absolutely with a thorough understanding of all ramifications. This may sound crazy, but in order to really prepare your ass for anal penetration, I would suggest starting to “train” 4-6 weeks before your bottoming debut. Why? The anus is a very sensitive area and it’s naturally in a clinching state (it spends most of the day tense and contracted, whether consciously or subconsciously). Because of this, one’s mental connections and physical relaxation abilities are not ready to just start sticking things up there right away — whether it’s as small as a finger or as big as a toy or penis.

One should treat their anal orifice and sphincter just like any other muscle – it requires a dedicated workout routine in order to get into working conditions of relaxation mode. The best “equipment” for this process is investing in a good anal training kit and water-based or toy-safe lube (and lots of it!). The kit will consist of usually three butt plugs in small, medium, and large sizes. You’ll want to start with the smallest toy and only after using each size with ease should you move on to the next size (generally about two weeks each).

The process goes like this: insert the dilator until it meets resistance (usually only about 2 inches). Hold it there for 3-5 seconds before removing it altogether, applying more lube, and then doing it all over again. For the best results, I recommend repeating this process with 8-12 reps per set and 2-3 sets per session. If you’re thinking this is too much of a commitment, rest assured. Anticipate spending about 3-5 minutes doing this, 2-3 times per week. If it slides nicely, you can go further — everyone’s anatomical roadmap is different, so you may find you need more or less time to get used to the depth and girth. After comfortably dilating for about 4 weeks, you should be ready for the real thing.

While it may seem that a butt plug is meant to literally plug you up, I don’t recommend going all the way in because it can go beyond the muscle and then cause unnecessary tearing when you remove it. The one thing to pay attention to is pain vs. mild discomfort. If it’s your first time doing this, it’s natural to feel uncomfortable with something up your butt — don’t worry. However, if you notice there’s persistent pain and/or bleeding, stop immediately and get in touch with your doctor (or us). 

 

For the top:

it’s primarily understanding the appropriate mechanics and relaxation phases of the receiver, along with proper pelvic placement for all engaging. Patience, proper communication, and relinquishing control will help allow your bottom to safely and pleasurable ride on into the sunset. So many tops just want to go balls deep at full speed and while that may be the goal, it’s definitely not going to happen on the first try.

The physical component involves proper foreplay. Some tops don’t like this and that’s OK, but you’d be surprised how much rimming can help put the bottom at ease and also warm up (and relax) their hole. It is imperative for tops to be a part of the bottoming experience while understanding the art and science behind it.

Still Apprehensive? Dr.Goldstein Debunks the Most Common Myth and Fear

The most common fear is that anal sex will hurt like crazy

If you properly prepare there may be mild discomfort, but it will certainly not hurt. If it hurts, you are likely doing something wrong like not using enough lube or using a position that doesn’t work for your pelvis.

The most common myth that we talk about all the time is anal douching

Most people will tell you that unless you clean yourself out, you’re guaranteed to have a mess on your hands. This simply isn’t true, unless, of course, you feel the urge to use the bathroom. Believe it or not, if you maintain a healthy diet that is full of fiber, your body will naturally clean itself. Feces doesn’t reside in the rectum, which is where the penis goes, but rather higher up in the colon.

Sure, there may be a fleck here and there that got stuck to the inside of your rectum, but that’s not a cause for concern. If you’re still paranoid about *something* coming out, there are two things you can do: stick a well-lubricated plug up your butt to see if anything comes out, or, you can use a small bulb with warm water about 30 minutes before sex to ensure you’re good to go. Stay away from store bought enemas as they can cause local irritation and dryness, which increases your chances of getting tears and/or contracting STD’s.

Another bad practice is using spit as lube. Unfortunately, spit doesn’t last very long and the anal canal isn’t naturally lubricating (like the vagina), so while it may seem fine at first, over time, the spit will dry up, once again increasing your chances of tearing.

Kick it Up a Notch: Best Toys for Anal Sex

If you’re currently enjoying anal sex, you may want to elevate your experience through the use of some toys. We always advocate for toys when it comes to the bedroom, they’re a great way to increase pleasure, explore your own and your partner’s body, and have fun! There is a plenitude of toys specifically for anal play, and Goldstein would like to recommend a few.

As I mentioned before, the best toys to buy are butt plugs, specifically an anal training kit. They have been designed in a way that their sizes help prepare your hole for proper engagement. As you become more experienced, investing in high-quality silicone dildos are a great way to go. I typically tell my clients to stay away from using fingers because sometimes your nails are jagged or too long, which can cause irritation and tear, or they can hit you at angles that can also do damage.

I also recommend finding lube, toys, and condoms that you love. While silicone lube is the best for anal sex due to its long lasting slick texture, it doesn’t play well with silicone toys (it will eventually break them down) and natural oils aren’t compatible with condoms. Water-based lube is great for sex because it washes off instantly and doesn’t stain your sheets, but it quickly dries out, requiring repeat applications. Toys are a personal preference and with so many options out there, the sky’s the limit. But, man, these new sex robots seem quite the innovation!

 

Last, But Certainly Not Least: KNOW YOUR RISKS

Safety and sexual health should always be first on your priority list when it comes to your sexuality, no exceptions. So, in order to ensure you are engaging in anal sex in the safest possible fashion, Dr. Goldstein shared with us some of the risks:

Besides preventing HIV and STD transmission, as with any sexual act, there are precautions people should take when considering anal sex. The external skin, rim, and walls of the anal canal are quite thin and are more prone to several types of injuries (some examples are: tears, hemorrhoids, skin tags, and abscesses).

Next: lube, lube, and more lube! Seriously, you can never have too much. You’ll thank me later. Also, using enemas/douching in its current form causes internal cell damage leading to higher rates of STD transmission and should be modified or avoided altogether. Many other concerns have been discussed prior, but lack of dilation, experience in receiving, or again, limited knowledge on the correct way to be the top, place both parties at considerable anatomical risk (i.e. injury). 

It’s Not For Everyone

It is important to remember that everyone’s sexuality is their own, meaning they should never be pressured to do anything they don’t want to do. If anal isn’t something that interests you, that’s totally cool, and if it’s something that does, that’s great, too. Anal sex is not just for gay men, it’s not just for heterosexual couples in which the penis owner is the top, and it does not have to look a specific way.

Like all sex, anal is different in every case and no circumstance is better or more “normal” than the next. Listen to yourself and your desires, if something doesn’t excite you, don’t bother, if it does, do a little research and get talkin’! If you have any questions after reading this article, please don’t hesitate to reach out. We’d love to chat!

Britanny Burr

Britanny is a Freelance Writer and Editor with a Bachelor of Arts in English. She grew up in the Rocky Mountains and is currently dwelling in Vancouver. She loves pool parties (though they are few and far between because she lives in Canada), hairless cats (though she hasn't yet met one in real life), and people who make her laugh. You can find her dancing, reading, drinking coffee or wine (dependent on the time of day), and watching Boy Meets World re-runs. @britburr

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