Tales from the Tail —We Ain’t Seeing Hole to Hole
I do not wanna talk bad about my ex, but (you knew there was a butt)… He had a small cock. Me (the bottom) plus his cock? It was more than manageable. Sometimes so accommodating that I didn’t feel a fucking thing. That wasn’t why we broke up, though. It’s just a matter of fact. We ended things because his job required him to relocate. And now, with me being back on the dating scene, I must say that there are some rather large penises out there.
Recently, I had an encounter with someone I just couldn’t handle. I tried, but he tore me up instantly upon entry. I am no quitter, though, so I let it heal and then set out on my conquest again and again—some successful, some not so much. I wouldn’t bleed—there was just a good deal of pain. My 💩 were also somewhat irregular for about three days following each session.
Fast forward a few months—I met the boy of my dreams. We have been dating on and off for weeks and finally we have decided to be a thing (whatever that means). The caveat? He is fucking HUGE. His cock and I currently do not get along. I follow Bespoke Surgical on Instagram and decided to preventatively seek some advice, in hopes of learning how to have a successful bottoming experience. I had also heard of Dr. Goldstein through some friends he successfully operated on and I decided it was time to give him a call.
I met for my forty minute consultation and we discussed my entire situation. After a thorough physical examination, we discussed two friction points (skin and muscle) that were my limiting factors. Since I had been abstaining from anal sex, nothing was evident in terms of pathology during visual inspection. We mapped out the plan and since it has only recently been a dilemma of mine, we decided to first take the non-operative approach—a more preventative route—and then we’d discuss performing surgery only of this failed.
What was first on his list? Seeing if I can gradually dilate both the skin and the muscle. He had me order a set of plugs—three to be exact—and then start with the smallest one. I also made an appointment with Bespoke Surgical’s in-house pelvic floor physical therapist, Mr. Steven Lavender, to not only help evaluate the restrictive points, but also give techniques for manipulation that would indeed allow for successful penetrative sessions. I had never even heard of this type of therapy before, but I felt like it was a great option, so I set up a consultation right away.
I didn’t understand at first why Mr. Lavender was asking me all sorts of questions that didn’t seem to have anything to do with my ass. He asked about my job, activity level, diet, stress, anxiety, goals for the future (both personally and sexually), and even the shape of my stool. He looked at my posture, breathing pattern, felt my gut, lower back, and hips, and then did a few other tests with a computer that measured pressure in my ass.
I was relieved to find out my bottoming issues were all explainable and fixable. Because of stress and long hours at work, as well as some anxiety, the muscles in my ass had become overly tight, along with an isolated area of the skin being restrictive. Not only did it cause a problem with getting fucked, but also it made shitting difficult for days after. And don’t forget how big my beau is.
Mr. Lavender provided me with the proper education, exercises, relaxation training, and tips for before and during sexual activity, as well as a simple change in diet, and things have already improved. I couldn’t be happier (and neither could my lover!). Within eight weeks of mostly at home techniques and three in-office sessions, I am happy to say I am fully accepting my boyfriend in all positions. And the best part? No tearing at all! Just pure orgasmic cock in my ass—the way it should be!
Cock in ass is a wonderful thing; however, there are plenty of limitations that can prevent successful penetration. Whenever I evaluate a client, I am always reminded of my residency director, Dr. Joel Horovitz, who constantly reminded us to “approach everyone as if they are not a surgical candidate. And as you delve into one’s medical history and physical examination, you have to convince yourself otherwise.” This approach is just as relevant in my tenth year of practice as it was in my training. The ultimate goal is to not operate and, with that said, I decided it was time to take on a pelvic floor therapist to help in this preventative management.
Our community’s sexual education, as it pertains to anal sex, has been quite limited—actually, non-existent. With that, if we took the time early on in our bottoming careers to discuss the correct ways in which we can accommodate, many injuries can be prevented. The above client is like many of us—he has eyes bigger than his hole and the process to achieve is of the utmost importance. I repeat “the process to achieve” because it is critical and we hope with our social media education and the addition of an in-house pelvic floor therapist, we can work on the psychological and physical facets of everything anal. So let’s talk a little more about it…
Skin and muscle. That’s it. No, I lied. Skin, muscle, and the brain—that’s the hole-y trifecta. How do we get all functioning in synergy is the question. Some are fucking blessed, but most need to learn full control. It can be a learned technique, a mastery of bottoming. But the real understanding is to know one’s limitations—knowing when too big is simply too big. There will always be one not to take.
Study your skin, listen to your muscle and see if you can actually control, contract, and relax your sphincter. Periodically, use a set of butt plugs and study how it enters. Is your skin taught? Too taught? Is the muscle fully relaxed or do you feel constriction and discomfort? What sizes can you take fully and comfortably? Mark that and periodically make sure this diameter matches your partner(s). If there is any discrepancy, then dilating in a controlled manner, slowly beyond your normal capacity, can start to stretch the skin and allow full muscle relaxation.
Also, a thorough anal evaluation can be advantageous to identify all factors as it relates to successful engagements. Having one’s pelvic floor evaluated and analyzed allows for us to understand all the principles that come into play with one’s limitations. With those measurements and modifications, we can do in-office therapy treatments that then allow one at-home regimens to take all of the above into account.
Now, if we choose the non-operative route, with the aforementioned tangible and significant data collected, and one still continues to have failures, it will lead us down other paths. Can we do in office localized Botox to the restrictive skin and muscle to allow improvements? Does the constant tearing need a surgical cleaning and intervention with or without Botox? Maybe there’s a small fistula in the region causing swelling and noted the pain?
The reality is we will totally find this out through that initial non-operative approach—if we or you do the above and this fails, clearly, we now need to choose a more aggressive approach. And this goes back to the “convince me that one needs a surgical intervention” mentality.
Taking a multidisciplinary approach is key and, now having pelvic floor therapy in our office, adds to all of our successes. Preventative bottoming is a new term that empowers all of us to understand our goals, all the while mastering our limitations. It is to empower you, the bottom, to not only create your own sexual narrative, but also to do it in the most successful ways possible. Deeper and deeper, or rather, further and further, we go.
Don’t forget to stay in touch on Instagram: me and Bespoke Surgical.
b-vibe Vibrating Snug Plug
Fun Factory B Ball Uno
Fun Factory Bootie Butt Plug
Doc Johnson Crystal Jellies® Anal Initiation Kit - Clea
Master Series 5 Piece Anal Trainer Set
Doc Johnson Mood™ Naughty 1 Trainer Set
Dosha 3-Piece Glass Anal Plug Kit
Lube Applicator Set
FLIP Water Based Personal Lubricant 4oz
überlube 100ml Bottle
überlube 50ml Bottle
überlube Good to Go Traveler Black
Pure for Men Fiber Capsules 120 Capsules
Pure for Men Fiber Capsules 60 Capsules
Dr. Evan Goldstein is the Founder and CEO of Bespoke Surgical. Dr. Goldstein has extensive experience educating and shedding light on health care issues relating to the gay community, and has been published in several national publications including The Advocate, OUT Magazine, Vice, Refinery 29, NY Mag and more.