First Time Bottoms | 5 Bottoming for Beginners Tips

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 below you should take on your own to get you set up.

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.

You may also want to check out our article about lube, which has more advice you might find useful.  

1. Get into training

First, some science: 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...

2. Your butt workout routine

  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... 


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3. Next: the real deal

Once you’ve succeeded in using all of your plugs with ease, you’re ready for your first time bottoming with the real thing. Continue using the plugs before or during butt play for the first few times, as well as taking a more dominating role in the beginning.

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 STD’s. 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. Bottom on top? Best positions for new bottoms

Once dilated and ready to go, I recommend sitting on the “D” and maneuvering until you find the experience comfortable and pleasurable. Take more of a dominating role in the initial stages: 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!

5. Keep it up

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 the 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 bottoming 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. 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 also the Founder and CEO of Bespoke Surgical, the leading private practice specializing in an elite standard of health and wellness care for the modern gay male. He received his medical doctorate from the University of Medicine and Dentistry School of Osteopathic Medicine in 2002. As the preeminent expert and thought leader in the field, Dr. Goldstein is committed to education and awareness—not only bringing the important issues surrounding intimate health to the forefront, but also eliminating the stigmas attached to it and has become the go-to butt and bottoming expert in mainstream media, having been published in Huffington Post, Cosmopolitan, Shape, Healthline, and Men’s Health, among others. If you'd like to find out more about the medical aspects of a healthy sexual life, visit Dr. Goldstein's practice,

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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