Anal Safety 101 with Dr. Evan Goldstein

Photo by Charles Deluvio on Unsplash / Edited by Caroline Colvin

When it comes to sex education, the focus is often the youth: the curious kids who need to know  about the physiological, emotional, and social developments to come in their (pre-)teenage years, once  sex comes into the picture. LGBTQ+ inclusive sex ed is no exception. Still,  conversations about inclusive sex ed can be made even more so by keeping older populations in mind. It’s not uncommon for LGBTQ+ people to experience a “second adolescence” when it comes to sex. Especially if they weren’t out in their youth, queer people in their 20s, 30s, 40s, and 50s are tasked with figuring out how to navigate queer sexual encounters (and the rush of emotions that come with them), as if they were an adolescent again.

One person in particular who is doing the work — and did the work in his personal life, out of necessity — is Dr. Evan Goldstein. Identifying, in his own words, as a “total homo or more simply put, a gay male,” Goldstein  was previously in a straight marriage. In that process, he experienced first-hand the daunting landscape of queer sexual encounters and the expectation that because he was older, he was “supposed” to have years of experience under his belt. Goldstein combined his surgical expertise and his drive to fill a decidedly queer void. In 2010, Goldstein founded sexual health care and anal surgery practice Bespoke Surgical. Combining sex education with the three principles of “prevention, restoration, and reconstruction,” Goldstein and his practice are dedicated to providing the full package to nurture their patients’ well-being.

 With his professional and personal expertise in mind, Cherry spoke to Goldstein about anal sex and all the (useful! important!) things you didn’t learn in high-school health class.

This interview has been edited and condensed for clarity.

Photo by  Charles Deluvio  on Unsplash / Edited by Caroline Colvin

Photo by Charles Deluvio on Unsplash / Edited by Caroline Colvin

Caroline Colvin: Can you talk a bit about Bespoke Surgical and how you came to establish it? How and when did it come to be?

Dr. Evan Goldstein: I was beyond unhappy studying heart surgery and after finally coming out (with my sexuality), I did a full introspection on who I was — and more so, what I wanted to be. This process in surgery’s “boys club” environment was not easy. But through this insight, I had an epiphany: I wanted to provide specialized surgical care to a community — my gay community — that had been so underserved for way too long.

Founded in Manhattan in 2010, Bespoke Surgical is now the leading practice delivering concierge-style medical services to address the unique health and wellness needs of the gay community — as well as the queer community at large, and now straight, cisgender men and women looking to engage anally. I am beyond proud and thankful that I was able to reinvent my path by specializing in and developing a much-needed space for the LGBTQ+ community in holistic care and an elite standard of surgical offerings. And so, Bespoke Surgical was born! We now have offices in New York and LA, and are continuing to grow. It’s an exciting time to pioneer the scientific and surgical approaches to my community.

CC: So, when it comes to anal sex, what should bottoms keep in mind when having anal sex for the first time?

EG: For the bottom, there are both mental and physical preparations that should be made. It’s crucial to have a thorough understanding of all ramifications. This may sound crazy, but in order to really prepare your ass for anal penetration, I would suggest “training” 4-6 weeks before your bottoming debut. [CC: OK, love this term!]

Why? The anus is a very sensitive area and it’s naturally in a clinching state (it spends most of the day tense and contracted, whether consciously or subconsciously). Because of this, your mental connections and physical relaxation abilities are not ready for you to just start sticking things up there right away — whether it’s as small as a finger, or as big as a toy or penis. One should treat their anal orifice and sphincter just like any other muscle: It requires a dedicated workout routine in order to get into working conditions of relaxation mode.

Anal Trainer Kit , Real Vibes on Amazon ( $10.99)

Anal Trainer Kit, Real Vibes on Amazon ( $10.99)

The best “equipment” for this process is investing in a good anal training kit and water-based or toy-safe lube (and lots of it).

The kit will usually consist of three butt plugs in small, medium, and large sizes. You’ll want to start with the smallest toy and only after using each size with ease should you move on to the next size (generally about two weeks each). The process goes like this: insert the dilator until it meets resistance (usually only about two inches). Hold it there for three to five seconds before removing it altogether, applying more lube, and then doing it all over again. For the best results, I recommend repeating this process with eight to 12 reps per set, and two to three sets per session. If you’re thinking this is too much of a commitment, rest assured: Anticipate spending about three minutes doing this, two to three times per week.

If it slides nicely, you can go further. Everyone’s anatomical roadmap is different, so you may find you need more or less time to get used to the depth and girth.

After comfortably dilating for about four weeks, you should be ready for the real thing. While it may seem that a butt plug is meant to literally plug you up, I don’t recommend going all the way in because it can go beyond the muscle and then cause unnecessary tearing when you remove it. The one thing to pay attention to is pain vs. mild discomfort. If it’s your first time doing this, it’s natural to feel uncomfortable with something up your butt — don’t worry. However, if you notice there’s persistent pain and/or bleeding, stop immediately and get in touch with your doctor (or us!).

CC: And then, what should tops keep in mind when having anal sex for the first time (whether with a biological penis or a strap-on / dildo?

EG: For the top, it’s primarily understanding the appropriate mechanics and relaxation phases of the receiver, along with proper pelvic placement for all those engaging. Patience, proper communication, and relinquishing control will help allow your bottom to safely and pleasurably ride on into the sunset.

The physical component involves proper foreplay and you’d be surprised how much rimming can help put the bottom at ease as well as warm up (and relax) their hole. So many tops just want to go balls deep at full speed and while that may be the goal, it’s not going to happen on the first try. Remember: there are three sets of muscles in the ass. And it takes time for all of these to fully relax.

Just like the above dilating, take your time and go slow. Oh and please use a lot of lube. And no, spit doesn’t count! Using lots of appropriate lube throughout the entire shaft allows the glide to happen. It is imperative for tops to be a part of the bottoming experience while understanding the art and science behind it. Good tops are hard to cum by!

Photo by    Charles Deluvio    on Unsplash / Edited by Caroline Colvin

Photo by Charles Deluvio on Unsplash / Edited by Caroline Colvin

CC: What in particular should older people who are looking to engage in anal for the first

time keep in mind (whether they’re topping or bottoming, whether with a biological penis or a strap-on / dildo)?

EG: Young or old, what I’ve mentioned thus far applies to everyone. The ass is non-lubricating and doesn’t discriminate against age. With that said, the skin does thin over time and one should take that into consideration. Lowering the pressures with additional lube, taking more time with the initial entry, and/or dilating is imperative. Also, depending on stamina and positioning, take it slow and choose what you know can be successful. Sex can be quite stimulating. No one wants any complications to arise, specifically during good ol’ anal.

CC: Do you have any brands and/or specific kinds of lube to recommend?

EG: Selecting the right lube truly depends on the situation, personal preference, and budgetary

requirements. [OK, tea!] There is no one correct answer to finding the best, but the key is to educate yourself  on all the pros and cons of each category, and sample many different types and brands to determine suitability and performance. The most important thing to know is that there is no such thing as too much lube — the real stuff, no spit!

Photo by  Annie Spratt  on Unsplash / Edited by Caroline Colvin

Photo by Annie Spratt on Unsplash / Edited by Caroline Colvin

A lube breakdown

1. Oil lube

Oils are all the hype these days, but they can also bring you to premature ejaculation. That’s

how good they feel and how long they last! So, beware. In fact, they become more slippery as you add heat/friction, which can really amp things up.

It’s important to note that oil- based lubes are not condom-safe (sometimes not toy safe either; check the toy’s packaging), will stain sheets and surfaces, and technically are not supposed to be used for internal anal play. They, however, are used extensively in massages and have scents that can be quite stimulating, producing elevated releases of endorphins.

2. Water-based lube

Water-based lubricants are completely toy-friendly and a great start to anal play. They are condom-safe, so they can lead from toy to cock seamlessly and (usually) offer natural ingredients that many people love. And one can’t forget the easy washability of not only your asshole, but more importantly, your beautiful sheets (can’t forget about those!). Water-based lubricants are not the ultimate lubricant, though, as many fail to commit to a smooth ride. They may be a little clumpier in application, but remember they are often a cheaper alternative, and therefore come in more generous quantities.

3. Water and silicone lube

Another alternative is a hybrid (water and silicone) toy-safe lubricant that takes the lubrication to the next level, but dives deeper into your wallet. We do like these because you do not have to think about changing mid-play from one lube to another. You have the enhanced lubrication and slippery feeling, with the above-mentioned benefits. However, they won’t entirely match the slickness of a pure silicone lube.

CC: Is there anything else you’d like to add?

EG: We covered a tremendous amount on a diverse range of anal topics. The key is breaking down the taboo and providing a non-judgmental space for professional conversations on important subjects. I thank you for taking on this narrative and being part of a movement that is so necessary in not only my gay world, but also the entire world at large. 🍒