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The Gay Butt Doctor Is In to Answer All Your Questions About Keeping Your Ass Happy

Evan Goldstein gave up heart surgery to pursue his true calling: helping gay men understand the ins and outs of anal sex

Ever since I gave my trusty dildo a chance under quarantine, I’ve grown hysterically concerned with the fitness of my asshole. While I’ve enjoyed giving my sphincter a rest, what if she’s rusty come the end of quarantine? 

To better understand my sexual health and how I might approach fucking in an era of face masks ya and temperature controls, I called up a bottoming expert for advice. 

Evan Goldstein is the founder and CEO of Bespoke Surgical, a gay men’s anal and sexual health clinic with offices in New York and L.A. I first heard about Goldstein through NYC’s bottom whisper network (i.e., my slutty friends). He’s a pioneer of anal botox, known for treating anal injuries and advocating for bottoming without pain.

What started as a conversation with the Good Doctor (No, not Freddie Highmore) about specializing in gay men’s sexual health loosened into a top-to-bottom discussion spanning the dangers of over-douching to why everyone ought to try fisting.

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What allows me the freedoms to provide medical and surgical care to our community is having an amazing partner, an outstanding and dedicated father to our twin boys (Phoenix and Sebastian), and now more importantly, a terrific and avid tennis player. Having someone at home to run the entire household and all the comes with it, is harder work then me operating on all your asses. It allows me to travel from NY and LA, bringing my overall skill set and more importantly, our mission of community -specific bottoming education to the masses. Relationships in general are hard work, as is ours, and we have both finally, somewhat, got into a groove of our responsibilities, which in turn makes this all possible. It’s not seamless that’s for sure, but it seems to be ripening with age (he may disagree). He has though managed to perpetually stay the same age as when we met (28), year in and year out; the smooth, beautiful boy I met that many years ago. ? Andy wishing you the best of birthdays and many more years of putting up with this moody old man. I thank you and I know our community thanks you as well. Oh and BTW, you are stuck with me! 521

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To start off, tell me about your practice and how you wound up focusing on gay men’s health?
I actually went into heart surgery first. I was miserable. Times were changing, people were dying and it just wasn’t what I wanted to do. I came out a little bit later in life. I was married to a woman first, then finally came out with my current partner. Over the course of the next 14 years — with two kids and the usual gamut along the way — I really started to focus on my own internalized homophobia.

I began to look at LGBTQ issues and see what people were doing on a surgical level for the community. Everybody was still back in the Dark Ages and treating only HIV-related issues, not analyzing the communities and figuring out what they needed from a specific health problem. 

Then I started to really look from a bottoming perspective and say, “Where do bottoms go to learn preventative approaches and education? If injuries happen — which they’re going to for anybody — how do they have spaces that are nonjudgmental and take away all of the shame and provide higher-end surgical sexual care?” That was what spawned Bespoke Surgical. 

I remember walking home in Central Park with my partner, and he’s like, “Why do I give a shit if I go to a gay practitioner? I just want to go to the best practitioner.” And I kept saying, “No, no, I think people want to go to where they feel comfortable. And that practitioner not only needs to be gay but needs to have taken it up the ass to understand all the issues associated with sex.”

Many of us aren’t educated on gay sex when we’re adolescents or even afterward, so what’s a common misconception about gay sex?
That you can go from nothing to something big right away. When you look at most stories of youth finally trying to take it up the ass, the first experience is usually a bad experience. It’s all because of the lack of education. Sex shouldn’t be painful. You shouldn’t be bleeding from it. If you’re having these issues happen, clearly we as practitioners and/or educators have failed. Because the reality is, it should be pleasurable. It should be fun. You should feel sexy, and you should be able to get off. There’s all these positive, positive things that should be associated with bottoming. 

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What do you think about when you’re getting it on? Are you analyzing your performance? Thinking about how you look? Or maybe wondering how much they’re into what’s going on? ⠀⠀⠀⠀⠀⠀⠀⠀⠀ Thoughts like this are common and can make it harder to, well, stay hard and to come. They can also make bottoming uncomfortable or even painful, because you aren’t able to fully relax. ⠀⠀⠀⠀⠀⠀⠀⠀⠀ Try being more mindful. Learn to stop letting your mind wander and focus instead on the sensations and the pleasure. ⠀⠀⠀⠀⠀⠀⠀⠀⠀ Another strategy is to mix it up when you hook up. Part of the reason the mind wanders is because people often fall into routines and get bored. ⠀⠀⠀⠀⠀⠀⠀⠀⠀ Good luck getting lost in the moment. ⠀⠀⠀⠀⠀⠀⠀⠀⠀ #FutureMethod #TheScienceOfSex

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I was playing with Future Method, your pH-balanced formula douche, and was shook when I read the instructions to just use a minimal amount of water and not go beyond the sigmoid colon. It was a radically different idea of douching from what I’d learned or practiced in a career of professional bottoming. It was a piece of advice I’d never heard before, in spite of me living openly and being really involved in gay sexual culture. So I can only imagine what it’s like for people who are a lot more private or conservative, or just less informed about their sexuality.

We don’t even know the basic anatomy of what’s happening when we’re having sex. One of the biggest things that’s helped me understand anal sex is fisting people.
You hit on a couple of points. Number one, everybody in the entire world should play with toys and/or get fucked to tap into the prostate and all of the pleasure zones of the pelvis. If you don’t take it up the ass, you’re never going to get that orgasm we all strive to achieve. 

Number two, you’re 100 percent right — when someone is fisting someone else, you have to be so on your game that you understand every nook and cranny of someone’s ass, right? Understanding where the tension points are in the skin. What about the muscles? What about that third ring that’s a little bit higher that sometimes things get stuck on? The angulations? All of that is by people actually playing and analyzing what they’re playing with.

That’s the key to sex: You don’t want it to be so mechanical that people don’t enjoy it, but at the end of the day, there needs to be communication, especially in an act like fisting. When you’re doing that, you’re so attuned on an anatomical perspective. It’s such a pleasure to work with the fisting community because everybody wants to just get better and better. Does that make sense?

Totally. They’re super bottoms!
When you look at douching, the Future Method system is in place for run-of-the-mill cock-in-ass. For fisting, porn sessions or whatever it is that’s longer, clearly people have their own routines of cleaning out. 

Water in and of itself or an enema solution is very, very caustic to the insides. So the solution needs to be appropriately pH-balanced specifically for the ass. Second, most people are over-douching. They’re either using shower hoses or large bulbs. What happens is the first time — and this is a classic — someone uses [a large douche], a little shit comes out. Great. Second time someone uses it, they feel super, super clean. Then the third time, they’re like, “Well, you know what, I want to do it one more time to make sure,” and there’s shit coming out again. That’s because it’s gone way higher than where the cock actually is gonna sit. 

I like to think that we’ve been in something of a gay sex renaissance for political, cultural and pharmacological reasons over past five years. But what do you think gay sex might feel like on the other side of this pandemic?
I look at COVID-19 from an STD perspective, which is how we should have looked at it to begin with. It’s the people who don’t know that they have STDs — and who harbor it and then give it to the community — that are the issue. 

I’m not saying don’t take risks and enjoy your sexual nature. I’m saying, do it, but own it to the point where now you’re able to create specific protocols to minimize your risk as well as everyone else’s risk.

Bringing it back to COVID-19, at the end of the day, it’s all about risk. It’s all about everybody now having it put out there in public. Now you’re able to say, “Hey, I’m with this person, how are we going to engage in the right way?” It’s a new era of sexual engagement because a lot of people, including myself, aren’t hooking up because of all this. But clearly, that’s not what everybody wants. People want to be fucking, right?

Right. It’s scary to think of the new risk paradigm that could follow this — especially when so much of our most open sexual cultures take place in the context of a lot of large gatherings.
The question is, now that you’re looking at risk from COVID-19, how do we look at it in specific communities? How do we better you as an individual and all these sexual acts we partake in? How do we make it safer for everybody? That, to me, is the key message. We need to bring it back to everyday life of saying, “If I’m going to the sex party and I’m using meth or I’m the bottom in a sling, what are my risks by doing X, Y and Z?” 

That’s where Bespoke Surgical takes a look at that to say, “Okay, how do you like to engage? How many STDs have you had this year? Are you on PrEP? Do you party-dose PrEP?” All these things where now we can say, “This is your risk. These are the certain things that we recommend doing.” It’s no different now that COVID-19 is in place.

I guess it’s my hope in this moment of pause that we take the space to think critically or process matters of sexuality that we’ve previously only pursued on impulse or circumstance.
One hundred percent. Look, I see 75 people a week. When we were pre-COVID, I did 15 surgeries a week. There are a tremendous amount of people that do care about their sexual lives and bottoming and how to get better, that’s for sure.

So I want to wrap this up a lighter note. I saw a tweet recently that was joking about how we finally all have time to let our anal fissures heal. Do you have tips on self-examining for hemorrhoids and fissures at home?
The main issue is toy play. If you’re not bottoming two to three times a week, you need to supplement with toys. It’s no different than going to the gym. You want to use toys in a way that’s going to allow the muscles and the skin to fully relax but also contract and build like you would build your glutes or any other muscle. 

As they’re using the toys, they can kind of feel fissures and hemorrhoids. It’s super hard, though. I know you’ve seen your ass and others, but it’s hard to examine your own ass. No matter what angle you’re trying, it’s always just a little bit off. The iPhone doesn’t do the ass justice. It’s usually like a 20 to 30 percent error in what it actually looks like. That’s probably why when I see someone in person, I’m like, “Dude, your ass is perfect. What are you talking about?”

Well, I always Facetune my ass pics just to make sure they’re nice.
[Laughter] With that said, now’s the time to self-evaluate your own bottoms, using toys, fingers, butt plugs and vibrators, and really doing good work to understand your anatomy and how everything is working and functioning. Clearly, if you’re having pain or you’re having burning sensations, there’s some element of a potential tear and/or hemorrhoid. Then it’s figuring out, “Hey, is it just over-the-counter medications and things to help it relax and then restart again? Or do I need to seek professional help?” 

We’re definitely open. I’m seeing people one day a week for semi-urgent emergent stuff where we’re able to help them understand where they are. A lot of these people need surgical correction or some element of guidance. I do a lot of Botox work to relax the muscle or the skin where people are constantly having fissures. The problem is, people let fissures go a little too long. The scar tissue that develops is never strong enough for them to actually engage sexually. That’s when I need to do surgery to clean it up. 

So, yes, if people have caught it in time, we can definitely work, especially now, to let it heal. Then they can get back on the horse in a controlled way so it doesn’t cause a larger issue.