Dr. Evan Goldstein from Bespoke Surgical writes about the ins and outs of anal sex – helping beginners and experts alike to have healthier, more enjoyable sex.

So you wanna take bigger, huh? How big? Like horse hung? Well, we have all been there, some more so in our dreams, but the fact remains that the end of the spectrum – enormously long, ridiculously thick, or the good old fist – is hard to achieve.

Two guys gay anal sex guide
Photo: Bespoke Surgical / Maxwell Poth

The key to successful engagement, specifically under these difficult demands (you hung tops are motherfuckers), requires the utilization of science, proper technique, and an overall understanding of what comprises the truest bottom.

Is that you? Whether it is or it is who you want to become, maybe we can help. But hold on to your butts, OK? Before we get to the big stuff, we should start at the bottom and take a refresher course on how to get there.

Pre-game Warmup

Let’s begin with getting your ass primed and ready for entry. The key is dilation, practice, and patience. Even though some of us might want to sit right down on the first cock we see, it’s critical to train your anal sphincters to accommodate and that takes time.

Your anal sphincters are muscles and just like your biceps or deltoids, they need periodic exercise in order to increase their flexibility and overall distensibility.

My recommendation might sound like something you’d expect from your personal trainer, but remember, with the ass always in contraction mode, deliberate muscle relaxation is key for getting your hole into tip-top shape.

Butt Plugs 101

My best suggestion is to invest in an anal kit with three gradual dilators. Next, use tons of lube with gentle play until you feel pressure amongst the anal sphincters.

Sex toys for anal sex
Photo: Bespoke Surgical / Maxwell Poth

Try to consciously relax to accommodate and then slowly remove – all in a continuous motion. Re-lubricate and insert again with a similar technique of slowly in, meeting resistance, and then slowly pulling out.

One should not feel pain at all and most may require this technique to be done 4-6 times before complete insertion. If it’s too much, it’s OK to end that session and then try again another day.

Most of my clients are instructed to use the small plug for two weeks, then both the small and medium plugs for the following two weeks, and then finally adding the large plug the two weeks after that.

Once you’ve gotten to the point where you can accept all three sizes with ease, pat yourself on the back (or the butt) for completion of this dilation accomplishment.

Under the Sheets

Now that you have perfected dilation, the key to being able to engage anally requires relaxation, good communication, lots of lube, and the proper position(s).

When first starting out, I recommend pre-dilating before the first show, all the way up to the large plug, not only to accomplish muscle relaxation, but also to lubricate the entire anal canal.

The best initial position is the bottom on top, so that the bottom is in complete control. It’s much easier to dictate the depth and speed that feels comfortable.

Once the bottom feels themselves opening up and there’s no longer any discomfort, feel free to switch things up – change positions, increase the depth, and adjust the speed.

Everyone’s internal map, if you will, is different, so you might find certain positions work better than others based on the length, girth, and curvature of your partner’s cock and the overall position of the bottom’s pelvis.

Don’t be afraid to experiment and let your partner know what works and what doesn’t. The goal is for the both of you to get off, after all.


Ok, so now that you are a somewhat seasoned bottom, let me give you some pointers. If you are a true bottom, then the key to continued success is to not only bottom, but bottom often – doctor’s orders!

Two men gay sex anal
Photo: Bespoke Surgical / Maxwell Poth

Though if you are like the rest of us and it’s more of a periodic anal party, then anal dilation is key during the dry spells or downtime.

Remember: the asshole is in contraction mode for almost 24 hours a day and if it is not periodically dilated, it will never be able to fully relax, especially when the demands are present. It is a use it or lose it muscle. So be consistent!

OK, OK – Now on to the Big Cock (or Fist)

The anatomical barriers of the bottom, in an attempt to achieve these “beyond capacity” acts of pleasure, may get restrictions from either the external anal skin not being able to fully stretch to accommodate the new girth, or similarly, the anal muscle not being able to fully relax.

Whichever the limitation, the question remains: what can we do to overcome this obstruction during entry, achieve improved success, and truly enjoy the (w)hole experience?

That was a trick question because the answer was already stated in the prior section. Whatever toys, cocks, or fists you use, analyze the sticking point and gradually dilate over time.

The overlying skin and muscle will stretch, but you need to utilize this new understanding—the science of gay sex – to push beyond its capacity. Patience is key.

Receiving help on this type of engagement from others is imperative – your partner can sometimes get a better sense of the “sticking” point than you yourself can with toys.

The key is surrounding yourself with others who understand proper mechanics. The act of fisting is wonderful, but just like flying an airplane, the takeoff (or entry in this case) is the toughest part.

Maneuvering the hand in positions that minimize girth allows for success and once beyond the muscles, the sky’s the limit. Well, maybe not the sky and rather the colon, but the space is essentially endless for penetrative fun.

Don’t get discouraged while exploring your new aspirations as it can take quite a while to finally reach your ultimate goal. But do pay attention to the maximal tension since injury can occur quite frequently when taken beyond what your body can handle.

And this leads us into the next section…

Booty Botox

So you have tried all of the above and still just can’t get to fully engulf the cock, toy, fist, or whatever you had in mind?

This is where Bespoke Surgical is leading the charge in helping people receive a better understanding of where the hiccups lie.

Botox injections have revolutionized our bottoming world by allowing full relaxation of the friction points – again, the skin lines front and back or the internal musculature.

Sometimes an operative evaluation is imperative to give a better understanding of the failed mechanics with surgical resolution being a necessity.

One-time Botox usually suffices, allowing full distention for time to come, as long as one continues the process of appropriate dilation and engagement. And here you thought Botox only helped remove your crow’s feet!

Injury is Inevitable

Anyone and everyone will at some point have an injured hole – it’s bound to happen and that’s OK.

Gay couple anal sex
Photo: Bespoke Surgical / Maxwell Poth

Some expected injuries may be an anal tear (called a fissure), dilated or clotted veins (called external or internal hemorrhoids), and/or extra skin folds (called anal skin tags).

Symptoms to expect can be bleeding, pain, discharge, or just a generalized swollen opening – none of which is pretty.

The general principle, if this occurs, should be to stop anal play until fully resolved, add stool softeners, drink plenty of fluids, take Epsom salt baths, and use suppositories like Calmol 4 or Prep H; for fissures, a prescribed compound medicine; and for hemorrhoids, steroid creams.

Since we shit regularly, it may take a week or so for complete resolution and sometimes there are some setbacks, which can be frustrating, but should be expected. It may seem simple, but it’s important to stay the course.

If things are persisting beyond two weeks, then it’s time to see a specialist. Earlier medical interventions may prevent surgical necessity. Regardless of any localized issues, with a better understanding of the above mentioned, hopefully overall trauma will be minimized.

The Bottom Line

The bigger the better right? Not necessarily. The key to better bottoming is using the science of gay sex to subscribe to better practice.

Full knowledge of anal dilation, initial cock entry, and proper positioning of anal play are essential whether you’re taking fingers, a toy, a cock, or a fist.

For play that goes beyond your body’s true capacity, understanding the proper skills to allow for larger objects of desire, along with all the potential mechanisms of injury, leads to fruitful and long-lasting engagements that are pleasurable for all partners involved.

And if your full desires have not been met yet with success, then see a gay medical specialist who truly understands not only the science of gay sex, but also harnesses the sensitivities of sexual identity.

Long live the bottom!

Dr Evan GoldsteinThis sponsored article was written by Dr. Evan Goldstein, the Founder and CEO of Bespoke Surgical, the leading private practice specializing in an elite standard of sexual health and wellness care for the modern gay male.

As the preeminent leader in the field and with offices in both New York and Beverly Hills, Dr. Goldstein offers concierge-style medical and surgical expertise to the gay community and is dedicated to not only bringing the important issues surrounding gay sexual health to the forefront, but also eliminating stigmas around gay sexuality.