Bespoke Surgical: A Guide To Bottoming

Feb 10, 2018
Bespoke Surgical: A Guide To Bottoming
Our friends at Bespoke Surgical provided a guest blog about ‘bottoming’ on the site today. It serves as an addition to my ‘Painful Sex’ content. Read along and also check out Bespoke Surgical for more resource information.

Bespoke Surgical: A Guide To Bottoming

Our friends at Bespoke Surgical provided a guest blog about ‘bottoming’ on the site today. It serves as an addition to my ‘Painful Sex’ content. Read along and also check out Bespoke Surgical for more resource information. Here’s a link to their Instagram profile.


By Dr. Evan Goldstein

Bottoming is not as easy as most people are led to believe. Painful sex isn’t just experienced by women – it’s very common for both sexes when it comes to engaging anally. Of course size plays a “big” role, but learning how to receive is actually hard work and it is imperative to have a clear understanding of proper and safe preparation for appropriate engagement — identifying correct lubricants with intra-anal placement, pre-dilation rituals, and initial correct positioning. Without the truest understanding of the LGBTQ+ community’s needs, one might not only limit their sexual potential, but also get injured during novice attempts.

Recently, a patient of mine shared an all-too-common story, where he bit off a little more than he could chew because of a “how hard could it possibly be?” mentality. He found himself in a relationship with a total top and, wanting to make it work, he sat right now. What happened? I’ll let him tell you first-hand…

A few days prior to what I anticipated would be my anal debut, I did some research by watching a couple gay YouTubers as they discussed their approach to being on the receiving end. Their recommendations were all over the map, without clear and concise directions, and I was quite surprised that almost all of them lacked commentary from physicians or other medical experts. After a few days of research, I decided to take matters into my own hands, combining all of their advice, and as best as I could, I began the preparation. Before I showered, I used store bought Fleet enemas. I found myself having to use several of them since each time I flushed out more and more stool. Even after an hour, as per instructions for continued applications, I still wasn’t clean. Finally, I decided to give up and proceeded to shower, freshening up my exterior.

Now smelling great and ready to go, my boyfriend came over and after a romantic dinner and me downing some wine (all in the hopes of it helping me relax), we started making out. Before I even knew it, we were naked on the bed and I could sense all he wanted to do was stick it in. I was eager, too, but with all the preparation I went through, I totally spaced and forgot the lube. My hole was already wet from him rimming me and the area felt so numb from all the alcohol we drank. I let him be the aggressor and he proceeded to enter. Right from the onset, I knew it didn’t feel right. Part of me was in severe pain and knew he should stop, but the sadistic part of me wanted it even more. We both came simultaneously and I must say, I was relieved for it to be over. As I was cleaning out his fluids, I started developing excruciating pain that was accompanied with bleeding. I knew something was wrong and found myself in the emergency department of my nearest hospital. Clearly, I was so fucking embarrassed and no one could even look at me, let alone understand the woes of a newbie bottom. I was diagnosed with an anal tear, called an anal fissure, and since acute enough, was able to heal with localized creams, suppositories, and warm baths. It finally improved after two weeks time, but now I am a little reticent to open my hole (as you can imagine). I have to keep reminding myself, though, that sometimes you have to just get back on that horse, but not without a trainer first.

The good news is – this unfortunate situation could have been easily avoided with proper education. The bad news is – there isn’t a lot of medically sound information available to newbies (and even experienced power bottoms).

First, let’s tackle the act of preparing. We all have created a culture where everyone feels the need to be overly clean. And yes, some of you are saying right now, “the cleaner the better!”, but the fact is that most people are actually empty of any shit with little required effort. Proper intake of fiber and appropriate eating habits should establish and maintain a once-a-day bowel regimen. This rids of all contents, leaving the anal canal — the dark hole that will receive the cock — without residue. Even if one defecates regularly, yet they still want an extra cleansing spritz, then for the most part, a gentle rinse with a saline enema or water-based delivery system — bulbs or shower adaptors — can be used. I don’t love these and at Bespoke Surgical, I tend to refrain from recommending any of them. Why? They all can cause dryness and irritation to the rectal wall and associated trauma to the anal region. Unfortunately, there are no enhancing solutions available currently out there. However, if you still must clean, I recommend gentle irrigation with less distention — one doesn’t need to fill themselves up like a balloon to achieve their desired cleanliness. A few times of this approach is all that is required, finishing with an exterior cleansing using your favorite scented soap to make the entrance enticing.

As for optimizing entry, the key is dilation. Ideally, it should be started at least a weeks prior, using a three-set anal trainer kit. The art of relaxation and total control takes practice and patience, with as little time as 3–5 minutes, 2 to 3 times per week. This should lead up to “the main event” and can even be done right before attempting, specifically to pre-lubricate the entire canal. Lubrication is also critical — not spit, boys (even in desperate times) — and foreplay doesn’t hurt either. With that said, water or silicone-based lubricants are the best and each are called for in different situations. Which brand is best is purely based on one’s individualized taste level, but regardless of what is chosen, please make sure the runway is slick and wet for landing!

Bespoke Surgical: A Guide To Bottoming

After pre-dilation and lubrication, optimizing initial entry is imperative, all with the receiver being in control. The best way to ensure this is to have the bottom sit on the tip and — just like dilating — engage the muscle, letting it fully relax, then removing the big daddy and doing it again. It may take three to four times to completely receive. Remember: there are three sets of muscles that need relaxation. Once fully in, control the tempo until it slides in and out smoothly. Once it’s rockin’, you can alter positions, remembering to choose ones initially with the receiver in control, until both parties are jiving. Appropriate sexual relations take time to perfect so don’t get discouraged. The more you bring the science into it, the better the results will be.

We at Bespoke Surgical are striving to optimize, not only this individual’s story, but all those who engage anally, with the hopes of improving plans for longevity through prevention, expert preparation, and scientific knowledge in the field. And to all you millennials out there, regardless of how many followers someone has on Instagram, Facebook, or YouTube, don’t take this as them being leading authorities, specifically as it pertains to sexual health and wellness. And to medical providers out there, us included, let’s get into the game to make sure an inclusive community has the essential tools to form a skill set that minimizes risk and maximizes pleasure.