First Time Bottoming: A Beginner’s Guide

Dr. Evan Goldstein

fundamentals January 08, 2020

Are you a first time bottom? If you’re new to bottoming, you probably have a ton of questions—and worries—about what’s in store. It’s human to worry, but know this: when it’s done properly, bottoming should be a fantastic—and pain-free—experience. Before anyone else gets involved, there are a few steps outlined below that you should review and run through before you start bottoming.

What Is Bottoming?

When it comes to anal sex, there’s typically a top and a bottom (and any combination of the two). The top is defined as the insertive partner and the bottom is defined as the receptive partner. And if you like both, you’re considered “versatile”. While these are all common terms within the LGBTQ+ community, they can be used to describe anyone of any sexual orientation or gender identity.

Common stereotypes include tops being seen as more dominant or aggressive, while bottoms are passive and enjoy submitting or being dominated by the top. But these are misconceptions and only further stigma and shame around anal sex, especially within the LGBTQ+ community. Whether you like it on top or on the bottom, these roles should not define us both inside and outside of the bedroom.

How to Prepare for Your First Time Bottoming

First, prepare for anal by getting into training and learning to relax your bottom. We spend most of our time with our butt muscles clenched. So you need to train them to relax on demand, in order to allow in toys, the ‘real thing’ or anything else you want to put in there (if that’s your goal).

We have three major muscles in our butt—all of them need to be relaxed for complete (and successful) entry.

Next, invest in a kit with three gradual dilators (small, medium, and large plugs). You’ll also need a water-based or toy-safe lube (as silicone lube can ruin silicone toys).

Finally, you’re ready for your workout… Follow a pre-bottoming anal training routine to ensure the best experience. Your routine can look something like:

  1. Using your kit—and tons of lube—start some gentle butt play with the small dilator until you feel pressure from the muscles in your butt.
  2. Try to consciously relax to accommodate and then slowly remove once you hit resistance—all in one continuous motion.
  3. Re-lubricate and insert again with a similar technique of slowly in, meeting resistance, and then slowly pulling out. This shouldn’t be painful at all—most people need to repeat this 4-6 times before complete insertion.
  4. Keep this cycle going for 12-15 times for a complete session. If it’s too much, it’s OK to end that session and then try again another day.
  5. The more experienced you get, the longer you’ll be able to play comfortably. You’ll notice everything relaxes over time—gradual progression is key.
  6. Playing with yourself while doing your workout is a good idea, as it helps you learn to control your pelvic floor. Also attempting real-life scenarios will allow everything that follows to go smoothly.

Repeat this 2-3 times per week. Use the small plug for two weeks, then both the small and medium plugs for the following two weeks. After that, add the large plug, which can take 4-6 weeks to work your way up to. The large is quite large: most people are ready for the real thing once they’ve managed with the medium. Speaking of which...

How to Bottom

Once you’ve succeeded in using all of your plugs with ease, you’re ready for your first time bottoming with the real thing. In order to help ensure a smooth ride from start to finish, try incorporating the following tips:

  1. Prep your booty the right way. If you’re looking to feel “ready”, make sure you’re sticking to a diet that’s high in fiber, which should include fiber supplements to help keep things moving along, and avoid foods that you know will cause some distress. For added confidence, some people choose to douche beforehand. If you choose to do so, make sure you’re using an Isotonic Douching Solution for safe and gentle cleansing.
  2. Don’t ditch your butt plugs just yet. Continue using the plugs before or during foreplay for the first few times. This helps pre-dilate your sphincter muscles, while also pre-lubricating your entire anal canal.
  3. Foreplay will help get your body – and mind – ready for what’s to come. When you’re relaxed, you’ll be able to enjoy bottoming more easily and fully. Start with kissing, body contact, oral sex, and rimming. You can also incorporate your butt plugs or other toys to help get you ready. Check out more tips for amazing anal foreplay.
  4. There’s no such thing as too much lube. Make sure you have copious amounts of lube on hand–preferably silicone–and keep reapplying as you play. By keeping things nice and slick, you’re helping reduce the bad kind of friction that can lead to injuries, like anal fissures. It’s important to not only have the top lube themselves up, but also your hole.
  5. Be in control. Despite common misconceptions that bottoms must be submissive, it’s important to start out by taking the lead, preferably with you sitting on top of your partner, which will help you control the depth and speed of penetration until your sphincters have relaxed and you’re ready to speed–and deepen–things up. Don’t be afraid to start slow and go at your own pace.
  6. Keep open lines of communication. Don’t be afraid to tell your partner what isn’t working (and also what is working). Sex should feel great and if it’s not bringing you pleasure, or if there’s any discomfort–or worse, any pain–stop, take a moment to reassess the situation, and then decide if you want to continue or call it a night. There’s no shame in taking a break or stopping entirely.

What Are the Best First-Time Bottoming Positions?

Once dilated and ready to go, the best first-time bottoming positions–whether it’s literally your first-time bottoming or if you’re a pro–are ones where the bottom takes more of a dominating role in the initial stages. Therefore, I recommend sitting on the “D” and maneuvering until you find the experience comfortable and pleasurable. This allows you to make sure you’re in complete control of the speed and depth, until your butt relaxes to its max potential.

This may take time—in one or several sessions—to allow you to truly embrace it all and feel beyond comfortable. Once this occurs, you can start experimenting with other positions, all the while analyzing the best angles for entry and enjoyment. Your top will probably have some pointers too!

Choosing a Partner for Bottoming

When it’s time to play with someone else—and this is important—find a top you trust. Someone who’s happy to go at your pace. Remember: it’s your butt, so you call the shots, including when the fun is over.

In addition to this guide, you may also want to check out our article about how to use lube for your bottom, which has more advice you might find useful. For now, let’s get into some tips for becoming a bottom safely and smartly.  

1. Follow a healthy diet

Most people think that douching is the panacea for getting ready to bottom. But the truth is that it starts long before you fill up your favorite reusable bulb (hopefully it’s ours) – it starts with your diet, including fiber and water intake, as well as a pre+probiotic, especially one that was designed specifically with the rectum in mind. If bottoming is on your mind, foods that you should seek out include fresh fruits, vegetables, leafy greens, whole grains, and unprocessed bran, while you should steer clear of processed foods, artificial sweeteners, fermented dairy products, spicy foods, and oily/greasy foods. Unfortunately, no matter how healthy someone eats, it’s near impossible to ingest enough fiber throughout the day, which is why I’m a huge advocate for incorporating fiber supplements into your daily routine. The best time to take them is right before bed because this allows fiber absorption and optimization to occur while you’re asleep and when your colon and rectum are also at rest. When we wake up, the natural change in the angle of our pelvis when standing stimulates our bowels. It’s why most people feel the urge to go to the bathroom shortly after waking up!

2. Don’t worry about accidents

A lot of "being ready” is psychological and that’s because there’s still so much unnecessary shame and stigma around bottoming and “mess”. As a result, we overcompensate and become so self-conscious about what may happen (but in reality probably won’t). You should find a partner who understands that shit may happen (literally). We’re all adults and there’s no need to stress over it. A big part of being able to enjoy anal sex is being able to relax. And if all you’re thinking about is cleanliness, then you’re setting yourself up for an unpleasurable experience.

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3. Have your supplies handy

You’ll want to make sure you have some essential supplies at your fingertips: a handful of your favorite condoms (if you use them), ample amounts of your favorite lube (make sure it’s compatible with your condoms), and a small towel to help clean up. With the rapid adoption of PrEP, condom use has declined; however, using condoms for added protection is still an effective way to reduce the transmission of STDs. Nowadays, there are plenty of options that are so thin they feel like you aren’t even wearing anything, so pick a couple and find the one that you and your partner like the most.

4. Communicate openly with your partner

Most people underestimate how important it is to maintain open lines of honest feedback with your partner. Anal sex is supposed to bring pleasure for everyone and the only way you’ll know this is if you and your partner discuss what feels good and what doesn’t. For example, you may feel discomfort, especially at the start, but you should never feel pain if you’re practicing safe anal sex. You can minimize any possible discomfort by applying more lube, switching positions, slowing things down, or even taking a quick break. When the fun is over, I also encourage partners to not only practice physical aftercare but also psychological aftercare so that each person knows what to do more of next time and what might be good to skip.

5. Keep it up - bottom regularly

The best bottoms bottom regularly. You know that feeling when you skip the gym for a couple of weeks and then you try jumping right back in? It doesn’t go well. And it’s the same in the bedroom. You need regular dilation to allow for full relaxation – not only to enjoy butt play – but to minimize injury. It takes time to get hardwired for complete and full control of your butt muscles.

There is a true art to being a bottom and thinking about it in a step-by-step process is key to its success. We promise you it will become less methodical—and way more fun—as you make progress. This guide will hopefully help get you started, but your own experience will really help inform your approach. Whether you’re a top or bottom or vers, get in contact through The Forum if you have any more specific questions. And good luck!

About the author

Dr. Evan Goldstein is the Co-Founder of Future Method and the Founder and CEO of Bespoke Surgical, the leading private practice in health and wellness for gay men. He received his MD from the University of Medicine and Dentistry School of Osteopathic Medicine. Dr. Goldstein is the go-to butt and bottoming expert, having been published in Huffington Post, Men’s Health, Healthline, and more. Learn about Dr. Goldstein by visiting his practice, bespokesurgical.com.

The views expressed in this article intend to highlight alternative studies and induce conversation. They are the views of the author and do not necessarily represent the views of Future Method, and are for informational purposes only, even if and to the extent that this article features the advice of physicians and medical practitioners. This article is not, nor is it intended to be, a substitute for professional medical advice, diagnosis, or treatment, and should never be relied upon for specific medical advice.

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