Client’s Tale.

I feel discomfort while I’m bottoming. Nothing crazy, but enough to make me avoid anal sex at nearly all costs. Independently, I recently began experiencing some other gastrointestinal issues that prompted a colonoscopy. The findings were not overly helpful, but after the procedure, I wound up developing an anal tear called a fissure. Shit happens, right? But fuck me! What a literal pain in the ass. I went back to the doctor who then referred me to a local colorectal surgeon. This doc placed me on suppositories and creams. Unfortunately, my situation wasn’t getting any better. Actually, it…


What’s the most important requirement for enjoyable, pleasurable, and successful bottoming? Is it the skin in the anal canal accepting what is being inserted into it or is it the underlying muscle in your anal canal that must fully relax? Could it be both? I’ll ask you another question. Let’s say, during my initial consultation, I found out that the asshole-in-question (literally) had previously been able to be successfully penetrated without any issues (and with all of the pleasures they sought)? Does that help you decide whether it’s a skin issue or a muscle issue?

Believe it or not, it’s…


Client’s Tale.

Ten years ago, with a rougher-than-usual partner and a thicker-than-usual cock, my asshole split. A literal tear occurred and holy shit did it fucking hurt. The scene was bloody and painful, and I would never wish it on my worst enemy. Even worse, it fucked up my relationship because I could no longer bottom. Crazy, right?

At that time, I saw a local surgeon and was placed on pretty standard creams, but they didn’t do much. I finally went in for surgery and had a lateral internal sphincterotomy. That’s where they cut the muscle inside your hole to…


Client’s Tale.

While my fissure gently weeps.

I can always trust my ass to be up for any task — whatever or whomever may come its way. But many moons ago, my booty finally broke down. It happened when I got overly confident one evening. Surprisingly, it wasn’t even a noticeably long or thick dick. Quite average, actually. I remember it like it was yesterday. First, I was in a weird position. Then, immediate excruciating pain. I suddenly felt wetter, but it was hard to tell with all the lube whether it was that or blood (or both). Unfortunately, I…


Client’s Tale.

I have a fucking grape on my asshole. Not literally, of course. But I do have a big piece of who-the-fuck-knows that recently appeared after some amazing bottoming (if I don’t say so myself). But before I go any deeper, let me frame the situation: my precious hole needs to be working 100% this weekend. My primary relationship (a long distance one with the man who provides for me), is flying in for some one-on-one time and good old-fashioned love making. I sure do miss our physical and mental connection.

Since we’re long distance, our open relationship allows…


The Peloton craze skyrocketed during the pandemic (if you were able to even get your butt on one), but what no one realizes is how their pelvises are being transformed forever by riding them so often. The pelvic floor is responsible for all these anatomical changes, both good and bad. Some of my own personal favorites — Ally Love, Dennis, and Jess King — are behind our experiences. All those “turn the resistance to the right” and “up in third position” help give us enviously high, tight, and round glutes (read: asses). But what it also does is produce excessive…


Client’s Tale.

Every single time I get fucked, I feel the urge to piss. No joke. And that’s not really the best sensation I want to be experiencing. I want the mind blowing, fuck-me-in-the-ass-and-fill-me-up-with-all-your-gooey-warmness kinda sex. You know what I’m talking about. However, my bladder instead feels like it’s going to burst no matter whose dick is in my ass. And for all those thinking it right now — yes, I use the bathroom before bottoming. It doesn’t make a difference.

I do get rock hard when someone is inside me. No issues there. I am able to fully relax…


Client’s Tale.

“You can take your Prince Albert and shove it up your — I mean my — ass!” I told him. Spoiler alert: he did. And it didn’t end well. Boy, was it a beautiful looking cock, though, with that shiny silver ball going right through its head. I’m getting hard just thinking about it. Can you really blame me?

Let’s start from the beginning. I dated (yes, past tense) a guy with a Prince Albert piercing and he loved to fuck. As you can imagine, so did I. But when it came to our first time, I was…


Client’s Tale.

Let me start by saying: I fucking love getting rimmed. Spit on it. Lick it like it’s an ice cream cone in 100 degree weather and you don’t want it to melt. Go to town while you admire its beauty. And when we’ve both eventually had enough, let’s both get off.

I used to think of my asshole like a Tootsie pop — people couldn’t wait to lick their way to the center — but now I feel like it’s that off-brand, clearance bin candy that no one wants.

Believe it or not, getting rimmed is the only…


Year in and year out, especially during the holiday season, I make an attempt to play Santa — listening to all my client’s naughty (and nice) bedroom wish lists. And just like Santa’s sled, our asses break down every now and again. But while Santa may cheer “Ho! Ho! Ho!”, Bespoke Surgical treats anal injuries (and whatever else may bring you into our office) with an open mind and without fear of judgement. So for our last blog of the year, I thought what better way to end it than with a listicle of reasons why an asshole (said lovingly…

Dr. Evan Goldstein

NYC Gay Surgeon discussing ASS: A\rt, S\cience, and S\ex www.bespokesurgical.com/

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