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Bespoke Surgical

The Ultimate Guide to Anal Sex 

The Ultimate Guide to Anal Sex

The Ultimate Guide to Anal Sex

Finally, a medical professional gets to the bottom of anal.


Evan Goldstein knows a lot about butts. He’s the lead surgeon at Bespoke Surgical, which caters to gay men’s sexual health at two centers in New York and Los Angeles. Patients appreciate his frank talk about gay sex, ass prep, and proper douching. Sexperts have weighed in on all the common questions about anal, but Goldstein knows a thing or two. Do gay men over-douche? What about painful anal fissures? We’re answering them all with The Ultimate Guide to Anal Sex.

When You Know You’re a Bottom

You can’t say how it happened. Maybe you started topping, then met a guy in college who you fell in love with. One problem: he was a total top. After a painful, messy first attempt, you tried again. And again. One day the flip switched and you came from getting fucked.

Many queer men say they’ve grown versatile with age and experience. But considering the time it takes to hone bottoming or topping skills, plus all the social stigmas and challenges these roles contain, it’s no surprise that many guys love one or the other more.

I’m a bottom. I knew it in high school watching porn. I loved group gangbangs and wanted to play like that — brutal, marathon fuck sessions with ten tops and a little spit. I can do that now, but only after years of training and practice. When you’re starting off, you should play gentle and respect your body’s limits. Start with the basics.

Cleaning Out 101

Step One: Eat Plenty of Fiber

A good diet will do most of the ass-cleaning work. Consume a high-fiber diet or take fiber supplements so that when you poop, your stool is collected together in one smooth mass. When you make fiber part of your daily regimen, you’ll reach a point where the most important step of your cleaning regimen is simply using the bathroom. Your body will get rid of most everything.

“Most people don’t consume enough natural fiber daily,” Dr. Goldstein says. “People should take additional supplements in order to help keep yourself regular. Metamucil is fine. I personally take Colon Cleanse Daily Fiber. It can’t hurt to increase your intake of leafy greens also!”

Step Two: Clean up the Leftovers

Over-douching (cleaning too deep, with too much force, or with too much water) can cause problems. It can lead to douche dependency and prolonged anal irritation. Goldstein, along with various pro bottoms (porn stars, escorts, and others) agree that you’re probably douching too much, or too deep.

I asked him what he tells patients. “Think of it like a colonic. What goes in comes out right away, a flow of water just within the immediate anal canal.” The anal canal is about 12 centimeters deep, he says. “A minimal amount of preparation is what’s needed, contrary to common belief.”

Bottom Like A Champ

Step One: Train Like a Champ

The anal sphincter (essentially your hole) is a muscle – one of the strongest in the body. You involuntarily clench this muscle closed for most of your life, and relax it when you use the bathroom. When bottoming seems painful and uncomfortable at first, it means you haven’t trained this muscle to relax and open. That’s why butt plugs exist.

I struggled with bottoming for years until one day when my boyfriend at the time found an old butt plug in my toy drawer. I had used it maybe once before. He wanted to try it in me. I bent over, gave him a big gob of silicone lube, and told him to go as slow as possible.

When it got too painful, I told him to stop, retreat, then gently push in again. We slowly, gently worked it in. Then we waited a few minutes letting me relax. Then he slowly, gently pulled it out. That’s when something happened.

“Babe,” I said, “push it back in again. Slowly.”

He did.

“Now tug it out, but don’t tug it out all the way.” My eyes were rolling back in my head. I liked the feeling of it pulling out. Over several months we did this, maybe once a week, gradually increasing speed until he could slam it in and out – fast. Then we got a bigger plug. I began to actually enjoy the feeling of something in my butt, and our sex took off.

I needed some training. So do most guys. I thought I was the only one with this story, but apparently this is something Goldstein encourages many of his patients to try.

“I usually recommend the Colt Anal Trainer kit by California Exotic Novelties,” Goldstein said. “I find that most of my clients don’t want to spend a lot on plugs or dilators so this kit ticks the boxes for being seamless and coming in a range of sizes. Most often, patients will start small for a few weeks and gradually get larger – usually working from 2 to 5cm in size.”

We talked about the benefits of solid glass plugs — my favorite for being friction-free and hypoallergenic – but since glass seems to scare people, a high-quality seamless, small silicone plug is recommended.

Step Two: Bottom on Top

Going too rough in the beginning can result in injury and tears that can be very painful. Goldstein recommends riding it — seriously. Start by sitting on his dick so that it slides in at your speed until your ass stretches and relaxes.

After you ease up, play with speed. Switch to doggy style, which gives you the ability to pull off quickly if it hurts. If there’s pain, stop. Don’t try to mask sensation or go fast if your body is telling you to be gentle.

Step Three: Learn Your Lubes

You can’t have too much lube, at least not in the beginning. Unless you’re a bottoming pro, spit won’t cut it. Spit will actually dry out your skin and make it less elastic. Water-based lube works in a pinch, but it dries out quickly and gets sticky.

Silicone lube is commonly recommended for anal. It’s hard to find any lube that beats the slickness and endurance of silicone. If you use condoms, silicone and water-based lubes are both safe with latex condoms.

One downside of silicone: It will stain sheets and linger on surfaces. Put a towel down or throw your “fuck sheets” over the bed before you play. Make sure to wash your hands thoroughly before touching items in your bathroom.

Some guys love oil-based lubes. Oil based lubes are equally as slick as silicone (some say they’re even slicker) but oil is not latex condom safe. Many oil-based lubes will also stain sheets and surfaces.

Hybrid water/silicone lubes will not match the slickness of pure silicone, but many people opt for hybrid lubes because they are advertised as stain-free and easier to clean than silicone. Experiment and find the lube you like.

Pro tip: Avoid warming or cooling lubes. These will irritate your butt. Most of them are not designed for anal.

Caring for Those Pesky Anal Fissures

Step One: Ouch

Sometimes anal fissures are a delayed reaction. You might feel a stinging sensation a few days later when you’re using the bathroom. The sensation can range from an itch to a sharp pain. Anal fissures are tears of the anal tissue that range in size and severity. Tell your doctor the truth — you got fucked, and now your butt hurts. Tell your doctor if there’s any blood, or if you’re having any other symptoms. Most anal fissures heal on their own, but a doctor can help — particularly with more severe anal injuries and tears.

What Is Bespoke Surgical?

I talked to Goldstein a little about why he started Bespoke Surgical.

As a gay man, I’d had horrible experiences in small-town clinics where the thought of group gay sex was preposterous and evil. In my small college town, one particularly churchly woman once told me that “I really needed to think about my lifestyle choices” or I’d be back in her office again getting tested for STDs. I left on the verge of tears.

That changed when I made it to cities. I know the value of having a gay-friendly doctor I could talk to openly about my needs without judgement.

“My partner Andy and I have been together for 10 years and have two twin boys,” Dr. Goldstein told me.

“I was matched for a fellowship at Mount Sinai Hospital in heart surgery, but I quickly realized I was very unhappy, and hiding from my true self and not serving my passion. Access to quality health care and access to like-minded individuals and medical professionals that give non-biased, non-judgmental care is key. Having access to this is vital to our community and for allowing it to continue to thrive.”

Founded in Manhattan in 2010, Bespoke Surgical delivers concierge-style medical services to gay men, specializing in prevention, restoration and rejuvenation. Bespoke Surgical was established by Dr. Evan Goldstein. As the preeminent expert in this field, Dr. Goldstein brings the important issues surrounding gay sexual health to the forefront. An important part of Goldstein’s practice is eliminating stigma and offering patients a safe, sex-positive environment where they can talk frankly and openly about their needs.

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Alexander Cheves