Whether you’re a beginner at anal sex or a seasoned bottom, Honey Wyatt speaks to anal sex doctor Evan Goldstein about how to prepare for safe and hygienic anal sex

For individuals or couples looking to get into anal sex, there seem to be two extremes to the conversation – wanting to dive straight in, or being terrified by the implications. 

Some straight men still worry that engaging in anal sex could mean they’re gay, while others are way too keen to get into it, without considering the impact on their partner. 

To find out how to prepare yourself for a safe and comfortable anal sex experience, Sextras spoke to Dr. Evan Goldstein – anal surgeon and founder of sexual health clinic Bespoke Surgical and sex care brand Future Method. 

Breaking the stigma around anal sex

There is a lot of stigma that prevents people from exploring anal sex, Goldstein explains, which is a hangover from the AIDs epidemic of the 80s. 

“We’re the first ever living out gay population”, he says. “Everybody else before me died, and how did they die? Anal.” People in their 40s and above, understandably, “still don’t want to engage in anal”, even with the advent of PrEP and PEP and anti-HIV. “Clearly when you’ve lost all your friends and family, it starts to create even more of a stigma.” 

In the heterospace especially, Goldstein adds, there is a lot of stigma surrounding anal sex. Putting anything up your butt is equated with being a homosexual. People also worry about pooing on their partner during sex, having gas afterwards, or their anus becoming “loose”, as well as shame that comes from stigma around it being dirty, 

“In Gen Z there’s a lot more fluidity, and there’s a lot more thinking differently as it relates to just pleasure. Instead of saying it’s gay pleasure, anal pleasure, oral pleasure, just thinking it’s entirely what makes you feel good”, Goldstein explains. 

“They really want to learn the right way. Early in my career, the gay boys were always like ‘I got this, I’m good, I know the right way’. And then you start to be like ‘Wait a second, you’ve been doing it wrong for all these years’.”

“It’s all about a positive feedback loop,” he says. “If I were to get people to start enjoying sex, where they feel comfortable in whatever it is – external play, finger play, internal play, toys, penis, fist, whatever – you start to say ‘Okay, I get this. It’s fun, it’s pleasurable’.”

Who is anal sex for?

“It’s for everyone that has an ass,” Goldstein states. “Every asshole can enjoy anal sex.”

Now that access to medication like PrEP and PEP has become more standardised among the young gay male population, fewer are using condoms. Although the risk of contracting HIV through anal sex has reduced, it’s still important to protect your sexual health, according to Goldstein.

“I always think: How do I reduce the risk as much as possible for the way that person engages in anal?” This involves looking at their thoughts and beliefs about anal, what people like to do during anal sex; the muscle ‘architecture’ of their anus and what the skin around it looks like – which is different for everyone, Goldstein explains.

Cisgender women have much thinner skin, for example, as do people who have transitioned from male to female. This can cause skin to tear much more easily, and create difficulties when bottoming. 

So, while anal sex might be for anyone with an anus, not everyone should approach it in the same way.

Physical preparation for anal: Tips for a safe experience

“Everyone has the same misconception, which is just ‘stick it in’,” Goldstein observes. But (shocker) it doesn’t work like that. “People get injured when they go from nothing to something big. The skin is very thin, so if you just go straight in with the penis, the skin splits.” 

What Goldstein tells anyone who is looking to explore anal for the first time, or who is getting back into it, is “it’s going to be six to eight weeks before you’re able to have a penis in your ass.” He encourages people to better understand their anatomy, and most importantly: to relax. “We have three sets of muscles: two that you can control, and one you can’t.” 

Then, there are three types of asses in the world. “A third of people, if they said ‘Tonight I want to bottom’, their muscles, their skin, their anatomy allows them to achieve success.”

The second third might be able to learn to do that by following the correct instructions, and the last third have something in their anatomy that prevents them from safely bottoming – like haemorrhoids or tears. This is when Goldstein speaks to people about the potential for surgery, or anal botox, to help them relax the muscle they won’t be able to naturally.

For the third who can build up to anal, Goldstein suggests using a dilation method to prepare the skin around the anus. This involves spending two week periods using a small, medium, and large dilator, or cone, to stretch the skin around the anus two to three times a week, over a period of six weeks. 

“During that process, we’re strengthening the skin,” he says. Stretching the skin in this way allows it to get tougher and more pliable. 

“Think about shitting and pooping,” Goldstein prompts. “That is forceful. But now think about how much more force can happen with the penetration of sex; the body needs to learn to withstand that force.”

If you experience bleeding or pain during the process, over the counter remedies like creams or suppositories are available to help people through the process. If you’re still feeling discomfort after that, Goldstein recommends people figure out how they can mentally feel comfortable with sex. “I tell people, ‘What I do is 60% functional work, 40% mental.”

Hygiene tips for anal sex safety

At this point, you might be wondering why it’s worth going to all this effort. The answer is twofold: anal sex, when not properly prepared for, can cause issues like incontinence and bleeding in later life, according to a 2022 research paper. 

And it can cause an enormous amount of pleasure: for those who don’t already regularly engage in anal, engaging the prostate (P zone) or A zone unlocks new routes to orgasms. 

“Men that are born with a prostate cannot get a normal prostatic orgasm through regular penile play, or oral to penile play,” Goldstein explains. “Because you’re directly stimulating that prostate, it starts to engorge in a really good way and your orgasms through it are much more enhanced.” 

Stigma surrounding anal sex can sometimes cause straight men to feel ashamed that they have the strongest orgasms from someone putting a finger up their ass. He says: “Then you start to dispel those myths to be like: look, it doesn’t only need to be a finger. It could be toys, it could be other things, maybe a woman wants to peg you and feels comfortable in that situation. And it’s all about pleasure.”

Goldstein’s brand, Future Method, also offers exfoliants and prebiotics “so you don’t have to clean much, or clean at all”. This is all part of Goldstein’s mission to encourage people to start taking their sexual health as seriously as their skincare or physical health. 

“People that work with their faces do facials and exfoliants and masks. Everyone is so attuned to working their face, but we aren’t working our sexual parts in a way to make sure they are clean and aerated.” 

As a parent, Goldstein is used to telling his kids how to wipe their bum and not to use wet wipes, but that care and attention to our genitals doesn’t continue into adult life.

“The positive feedback loop is ‘if I put in the work and have really great sex, then it doesn’t become work.”

Read more: How to masturbate with a penis

Best positions for first-time anal sex

Once you’re ready to have anal sex, it’s about finding what works for you, Goldstein explains. Bringing dilators or sex toys into sex can help bridge the gap between preparation and full-blown anal sex. 

“What does it do? It pre-lubricates you; it pre-dilates you,” he says. “It allows you to get into the groove of everything.” For those with a partner who has a penis, “use their penis as a dilator”, he advises. “Sit on it, and create space.” 

Once you’re comfortable, he encourages people to incorporate different positions. Those where you can see your partner are ideal for beginners, as it’s easier to read one another’s facial expressions, which can foster better communication after sex. 

“There are different positions that create more stress, like doggy style,” he explains. This all depends on someone’s pelvic anatomy, so taking it slowly and testing what works for you is important.

Rebuilding confidence after negative experiences

While experimenting with anal, as with any kind of sex, there is a possibility that you could experience pain or discomfort afterwards if you haven’t taken the necessary precautions to protect your health.

In these cases, not having anal sex and rest is key, Goldstein says. “With any anal trauma, it’s a three to five to seven day rule – meaning it should get better with over the counter [treatment], whether it’s a suppository, a lotion, or taking a bath.”

Once you’re fully recovered – or your symptoms have gone away – go back to the start of the dilator routine, Goldstein urges. “Now you need to go back to the beginning of the toys because there’s scar tissue.

“Let’s say you tear the skin, the skin heals, but the scar is weak. What we need to do is coach it to heal correctly. By starting the toys and creating that friction, we’re getting the tissue to be tougher.”

Eventually, the scar should heal and you should be able to get back into sex, Goldstein explains. But if the same discomfort or pain keeps occurring, this is when it’s worth consulting a doctor who can advise you on what changes to make or further treatment you might need. 

Regardless of any major, or minor, problems, keeping an open dialogue with your doctor about your pelvic health will be useful as you age, as how you engage your pelvic floor, during anal sex or not, will change throughout your life.

“A lot of people are coming to pelvic floor therapists because they’re having pain: vaginal sex is painful; erections are off; they have discomfort when they ejaculate, and the ass, the penis, the vagina are all connected.”

“Anal sex is a gateway to allowing people the betterment,” he says. 

Bottom: someone who ‘receives’ during anal sex