Dr. Evan Goldstein

Dr. Evan: Any medical problems, blood pressure, cholesterol, diabetes?
Michael: Nope.
(mouse clicking) Do you take medication daily?
PrEP.
Sure. Shitting okay? No bleeding, discharge, mucus?
Everything’s cool.
Got it. (mouse clicking) From a bottoming perspective — You feel comfortable?
Yes.
Very good.
So are most people coming into your office for maintenance?
Most of our work is concerned with functionality. With bottoming comes a lot of trauma. Some people come in because they’re crazy tight, and they’re limited sexually. We also do cancer prevention. Most people do annual pap smears.
And you perform surgeries too?
Yes, for hemorrhoids, fissures and obstructions. But my surgeries aren’t crazy. Most are around 15 minutes.
Did you always dream of becoming a colorectal surgeon?
I originally studied to be a heart surgeon. I was on that trajectory, but realized mid-way that I was throwing myself into that work because I didn’t want to admit to myself that I’m gay.
When did you fifinally come out?
I was closeted until I was 32.
Really? That late?
That late. I mean, I was hooking up with guys and girls, going back and forth, kind of questioning. I even got married to a woman. I wish someone would have just said, ‘Evan, it’s cool to do this. Go figure out who you are.’ But, you know, in my teens I volunteered at a hospital, and I saw so many gay men die. “You can’t be gay” was imprinted upon me, and then when I was 14, my cousin died from HIV/AIDS.
How old was he?
He was probably in his late-thirties.
It must have been really scary for you. Did it stop you from experimenting? Were you having sex with men before you came out?
The problem with anal was that I was fucking crazy tight. In med school I developed fissures and I had ass surgery twice.
So your life’s work evolved from personal experiences?
I could never just drop my drawers, open my hole and take dick. I envied the people that could. Now I’m trying to provide that for my patients.
If I would’ve heard about your practice ten years ago, it would’ve sounded like science fiction.
Totally. And now people come in, they’re so happy that a place like this exists. ‘Why doesn’t it exist everywhere?’ We’re pushing the narrative and normalizing anal care. I even see patients from the Vatican.
Wait, men from the Vatican come all the way to New York City to see you?
Yes.
Wow. What are some common problems that patients come in to treat?
Tons of people come in because when they bottom, they can’t get off or they lose their erections during sex. It’s hard when someone’s inside of you. Literally. This is normal because what happens is the mechanism for the ass can take away the mechanism for the dick to work. Some people, no matter what they do, can’t cum when someone’s inside them. They feel good, they feel pleasure, but the erection is not there. And it has nothing to do with them not being capable of getting an erection.
I’d love to hear your scientific breakdown of how and why bottoms experience pleasure during sex.
First of all, externally, the skin is so sensitive. Internally, pleasure comes from pressure, and for those who have one – hitting the prostate, milking it, directly stimulating that gland and then, BOOM! You ejaculate! Does that make sense?
Yes. How do you fix patients that come in with a worn-out hole?
I’ll introduce you to Steven Lavender, our physiotherapist. He’s a great resource on that topic. You can chat with him about that.
I’ve always heard that over-douching can strip out the anal flora. Is that the term?
Yeah. The reality is if you’re shitting normally, there shouldn’t be stool present when you’re having run-of-the-mill anal sex. Now there are phobias, there’s stigma. I understand why people douche. Naturally, enemas and douches strip the rectal lining and cause swelling. Supplementing fiber, changing diet, exercising can help so you don’t have to douche as often.

And water is very harsh?
What happens is water kills the cell lining. That’s why a lot of people have more mucus, and they think their ass is cumming.
So this idea of cumming out of your ass is not…?
You probably have an STD or you’ve over-douched.
Got it… In our current gay sexual renaissance, many men are trying fisting at younger ages. It used to be something that you experimented with in your late-thirties, when you’re loosened up and needing bigger…
I equate it to gauges for ears – you have to keep going bigger as the skin stretches. The fisting community is super amazing. They’re very communicative. And I don’t see a tremendous amount of fisters coming in with pain or prolapse. Remember, many are muscular dudes that squat and that offsets looseness.
How does squatting affect the hole?
When you’re doing squats, you’re doing pelvic floor work, like Kegel exercises. It’s building strength and stretching the rectal muscles. I always say the best bottoms are the ones that have sex at least twice a week. Either with someone or with toys. But you’re right, I am seeing a lot of younger guys that are into fisting. Their bodies are not as mature yet and haven’t developed enough strength, so they’re getting prolapse much earlier.
Gen Z has grown up watching extreme porn since they were 12.
We just need to make sure people understand – your hole is muscle and skin. There are three types of bottoms. Bottom number one – I can open up and take anything, whenever. That’s about a third of bottoms.
That’s pretty high. I thought it’d be a more specialized group.
The second – I need practice. I can’t open at will. I do have some discomfort. And the third type is door closed, I’m tight. I tear. I’m irritated. If you’re in these last two groups, you can’t go from nothing to a massive dick, and I often suggest anal Botox.
I heard about anal Botox for the first time just this year. When did you start offering it?
I’ve been doing it for around 12 years.
So you’re a “hole-tox” pioneer?
It already existed for fissure management, but I normalized it for bottoming. Botox is a game changer for many men that want to bottom. It works towards relaxing the muscles and allowing people to dilate and stretch the hole.

I thought it was cosmetic, more like anal rejuvenation, but it’s actually for functionality.
Totally. So let’s get back to why you’re here today – I’ll take a look inside and out.
Okay.
(examination paper rolled out) What you’re going to do is take off your underwear, lie on your side, and face the wall.
(undresses)
If you can help me grab the cheek here. Good. So this is called an anoscope, which has a camera magnifier at the end. First, I look externally in the creases for warts, ingrown hairs or lesions.
Alright.
All is good. Now this will be cold…lubrication. This is how I tell people to do toy stuff. Lots of lube. Now, little pinch. Three, two, one. Each time I feel pressure, I gently remove and relubricate until I’m able to pass without resistance. Now I’m looking through a small microscope. (looking inside the anus) Everything looks great. Squeeze for me.
(squeezes)
Good. Relax.
How much would you say not being able to bottom is psychological?
Nine times out of ten, people choose to identify as a top because bottoming is not pleasurable. Personally, my psyche was very restrictive.
And up until now there wasn’t a medical professional to talk to?
That’s right. I couldn’t perform surgery on myself. That was the impetus for me starting Bespoke Surgical. I wanted to develop a community-based practice. A study shows that 90 percent of gay physicians don’t talk about gay sex. Which is not okay. Their philosophy when it comes to the ass is only focused on taking a shit. And it’s like, yeah, my shits are fine, but my boyfriend can’t fuck the shit out of me.
So you obviously engage in the same sexual practices as your patients?
I always humanize the situation, in terms of how I communicate and make people feel comfortable. People have stigmas, biases and they’re coming in with an anal issue? I try to take that shame away. Another problem is a lot of physicians don’t take Medicaid. How do you take from the rich and give to the poor? I’ve always taken Medicaid. I have ten surgeries planned for today, six of them are insurance-based. And four of them are covered by Medicaid. I get maybe two dollars for a Medicaid surgery, and it doesn’t matter. My goal has always been to care for our community.
Have you experienced any pushback from your colleagues, or in your social world, for the type of care you provide?
Quite the opposite. I’ve never felt any negativity. Everyone is beyond supportive of what we’re achieving. Even my neighbor Martha Stewart sends me tons of patients. I love Martha – she’s such a champion of what we’re doing.
What? Martha’s your neighbor? (laughs)
She’s just across the street. Alright, I’m going to remove the device now.
Thank you.
Now let me make sure your ass is all clean and dry.
Okay.
While you get dressed, let me shut down the machine… (machine powers down) Everything looks great. No warts, no masses, everything is where it should be.
How does looking at asses all day impact your sex life?
It’s just a hole, it’s not sexual. In the office, it’s the professional side: how do I get patients to where they want to be? A sexy hole is always going to be my sexy goal. Clearly, as you can tell, I’m a butt guy. I love ass.
Please describe your perfect hole?
When anyone asks me that question, I always say the only reason why I’m still with my partner is because he has the best hole. (both laugh)
Wow, okay. He’s fine with you saying that publicly?
Of course! For me, I’m not into hair. I’m much more into the twinkier holes. I like youth. That’s what gets me off. I don’t know if it’s because I’m more dominating-controlling — I’m a Leo. Does that help?
Defifinitely gives me an idea. (both laugh) Thank you for your work. It’s amazing that you’ve taken the initiative to build this much-needed practice.
I work my ass off. Literally. I’m out the door at six in the morning, and I don’t get home until eight at night. It never ends. Now let’s get you introduced to my colleague Steven.
(a quick walk down the hall)

Steven: Thank you for coming in.
Yeah. Nice to meet you.
Your magazine is amazing. How long have you been working with BUTT?
Basically since it started. I was happy to see a copy in the waiting room.
That’s amazing. So you’ve come in today for a couple of tests. You just need to drop your pants, lie on your left-hand side. Don’t worry, the window is one-way.
Okay. (undresses)
Evan and I have been working together for a long time now and I adore him.
What I do here is take care of the in-house research, the medical testing and rehab.
Can you tell me more about your research?
Of course! (grabs device) This is the anorectal manometry device. It is the gold standard. It involves me putting this into someone’s bottom — there’s a balloon here that goes into your rectum that I gently inflate to elicit spinal sensations and reflexes.
How does this all come together?
In three different graphs and a reading of the anus’s shape. Everyone’s ass is different. There’s the classic tunnel, then a slightly cone shaped, the hourglass and so on. Each type affects the position that you can get fucked in.
Got it. So, is achieving maximum pleasure about a cock finding the right shaped hole?
Oh, for sure! Alright, let’s have a look and see what your overall pressure is. Three, two, one… (inserts device) Here we go, now squeeze.
(squeezes)
That’s a very good squeeze. Okay, relax. With this reading, I can compare your numbers with the data we’ve collected from your peers, and we’ll see if you’re normal, tight, not tight, and whether there are other problems.
So this is how you gather your useful in-house research?
Yes, and it’s very helpful! For example, someone comes in because they’re having trouble bottoming, we can run this pressure test and go, ‘Based off your physiology you will never be the best power bottom in the world. No amount of poppers or booze will help you.’
Oh, that’s tough.
No, Michael, never compare yourself to other bottoms. Do what’s best for your body. Research done in the Netherlands said that 60 percent of men have pain during or after sex and our research shows the exact same numbers.
So one’s capacity to take dick is not just psychological?
Guilt, previous painful experiences, internalized homophobia will play a part. There’s no doubt about that. But if someone says all you have to do is sit back and relax to bottom, well, that’s bullshit.
My friend, Bobby Ryker, is an adult actor that specializes in fisting. He says that his fisting approach actually builds muscle and doesn’t lead to prolapse.
We have people come in who want to learn how to get fisted or want to take more than one fist. Others ask for us to teach them how to prolapse.
A prolapse, from a health perspective, is a medical condition?
A prolapsed anus is a medical condition. However, it is a fetish. And it’s highly prized for many people. What we do is offer counselling. We teach our patients how to keep basic continence, to have control over the muscles to be able to squeeze, relax and prolapse at will.
Oh, yeah? How?
We test them regularly and teach them how to do pelvic floor muscle training. Rosebudding is now a big fetish. So we offer advice and strategies to mitigate the risk. We monitor them very closely, and measure the prolapse, we exercise them. Now, why don’t we do the other tests?
That’s what I’m here for. (laughs)

This is very conversational. We’re going to be talking all the way through. Now, give me one big COVID cough.
(coughs hard)
Excellent. Give me a squeeze.
(squeezes)
Excellent. Give me a big, beautiful push.
(pushes)
You are so good at that. You can tell a lot about a man’s character by the way they attempt that request. (both laugh)
What do you do socially?
Evan and I don’t like to go out too much, because you know, if Dr. Goldstein or myself walk into a gay bar it could really kill the vibe. (both laugh) You know what I mean? Especially the fuck places. As much as everyone likes us, no one wants to see their health care provider ramming someone in the butt.
Mhm.
Alright, everything’s good. You have very good bottoming pressure!
Yeah. No complaints. (laughs)
The quality of your tissue is excellent. Everyone has got different amounts of connective tissue and muscle tissue.
(points to photo) Is that The Beatles?
No, the Rolling Stones when they were young. I bought that photograph for Evan because he sees himself as a little rock’n’roller. Are you into large play?
Not really, not yet at least.
I think you have the capacity for it. And I really mean that in a lovely way. You don’t need to limit yourself. Alright, now can you squeeze the muscles that twitch your cock.
Uh… (twitches cock)
There you go. Those are your proper Kegel muscles. You’re going to squeeze just those muscles as hard as you can until I say stop. Squeeze like crazy.
(squeezes)
Keep squeezing. Come on, you can do it! Now, relax.
So all of this is to test pressure?
Sensation, reflexes and pressure. Now we’re gonna get all these balloons out of you and you can put your pants back on.
(dresses)

Now your results: you have lower than normal internal pressure, which means a dick doesn’t have to fight too hard to get inside. Michael, I’m guessing you don’t have any trouble getting railed – you were built for bottoming.
Thanks, I’m happy to have official medical confirmation.
Poppers, which relax and soothe the muscles, would only be the icing on the cake for you.
So you’re pro-poppers?
They have their place, and they are part of our world. We have to acknowledge and embrace them and not be stupid about it. You shouldn’t use poppers to get a false sense of confidence about progressing to larger sizes. That’s a good way to get a nasty fissure.
Noted.
Then we’ve got your external anal sphincter test, and you knocked that out of the park. Your squeeze is so strong that you could send your top to the hospital with a broken dick. Congratulations!
Thanks, I guess? Do your patients ever get aroused during treatment?
Oh, sure. And that’s beautiful too. I’d never make them feel bad about that in any way. We don’t want men to stifle their ability to become erect. It only takes two or three deliberate attempts before you give yourself erectile dysfunction.
Really? It’s that vulnerable?
You never want someone to be thinking, ‘Oh this is a medical office and I shouldn’t be getting a hard-on.’ Like whatever, get a hard-on! The whole idea is we’re getting people to know, love, trust, respect and be proud of their cock and hole.
That’s a good philosophy.
The gay community needs more of that in every way. What we do here is teach people how to develop endurance and to understand themselves forwards and backwards. If you’re prepared, do the exercises, know your body, then even on the worst day of your life, you can drop your pants in the middle of SoHo and go, ‘Fuck me!’ (both laugh) Now, who’s not a winner?
That’s probably the only time I’ll ever hear a medical professional say that.
You were so wonderful. I’m so glad that you came to visit. Do keep in touch.
Do I have your card? Oh, yeah, I do… I also work with an architecture and design magazine.
Oh my god. Two of my favorite things – ass and architecture.