My partner wants me to bottom, and I’m not sure I can. Let’s talk.

I’m a sex therapist, and I’m also a gay man. Personally, I mostly top, and I’ve had my fair share of struggles when it comes to bottoming. When I’ve bottomed, it’s been incredible, but I’ve also had some awful experiences that left me feeling unsafe and hesitant to try again. I want to be transparent with you — this is not just from a place of professional expertise, but also lived experience.

Queering sex is something I deeply care about. It doesn’t always have to fit the traditional, heteronormative models of what we think sex should be. Dr. Joe Kort coined the term Sides a few years ago, a term that’s been helpful for me and many others because it normalizes different ways of engaging in intimacy without feeling like we have to fit into rigid boxes like “top” or “bottom.” This is important because, in our community, sexual roles still hold a lot of weight.

If you’re reading this, you may be struggling to bottom or feel unsure if it’s something you can do. This essay is for you, to help you understand what’s getting in the way, and to guide you through approaches that might make bottoming less daunting and more enjoyable.

Trust, Trauma, and Attachment

The idea of bottoming — especially if you’ve never done it or have had a bad experience — can feel like standing at the base of a mountain, looking up, and wondering why anyone would willingly climb it. Your mind might race, your heart might pound, and bottoming may seem like an impossible task. But before you clench any tighter, let’s talk about why this is happening. Spoiler alert: it’s not just about your body. It’s about what’s happening in your head.

As the trauma expert Bessel van der Kolk once said, “the body keeps the score.” Trauma related to intimacy can lodge itself in the body like an unwelcome house guest. Maybe you’ve had an earlier relationship that went sour, leaving you distrustful, or perhaps something deeper took away your sense of safety. For many of us, past experiences leave us feeling vulnerable, and bottoming requires vulnerability in a big way. So, when you’re exposing your most intimate self, it’s understandable that your brain might shout, “Danger, danger! Get out of there!”

The truth is, your brain isn’t trying to sabotage you — it’s trying to protect you. Anxiety and avoidance are its tools for keeping you safe from perceived threats, even if those threats are just echoes of the past that no longer exist. But the good news is that you can learn to make peace with these echoes.

Enter Therapy. A good therapist can help you work through past traumas, like a mental gym where you reframe negative thoughts. Cognitive Behavioral Therapy (CBT) is particularly effective for this. For instance, you might write down thoughts like, “What if it hurts too much?” and challenge them with evidence-based, balanced perspectives like, “If I take it slow, use lube, and communicate with my partner, it can be manageable or even pleasurable.”

Attachment Styles and Trust-Building. The way we attach to others — whether anxiously, avoidantly, or securely — can greatly influence how comfortable we are with bottoming. If you’ve been holding back because of trust issues, building emotional safety with your partner is crucial. Rebuilding trust is like laying bricks, step by step. You can start by having open, low-pressure conversations about your comfort levels. Share what feels good during non-penetrative activities, and take small steps towards intimacy. Trust isn’t rebuilt overnight, but with consistency and honesty, you can reach a point where bottoming feels safe both physically and emotionally.

Cognitive Behavioral Therapy (CBT)

CBT is like a gym for your brain, helping you reframe those negative thoughts that tell you bottoming is scary or unsafe (Grabski & Kasparek, 2020). Therapy can also bring in techniques like Mindfulness to teach you how to stay grounded in the moment, rather than letting your mind spiral into fear.

Here’s an example of what CBT can look like in this context:

Automatic Thought # 1: “What if it hurts too much and I can’t handle it?”

Evidence For:

• There is some discomfort involved in bottoming, especially if it’s a new experience.
• I may have read stories or heard from others about it being painful.

Evidence Against:

• I’ve heard that using enough lube and being relaxed can reduce the pain significantly.
• Some people enjoy bottoming and say it gets easier with experience and good communication.
• My partner has said they want to take it slow and make sure I’m comfortable.

Balanced Perspective:

• “It’s possible that it could hurt a bit, but I can take it slow, use lube, and communicate with my partner. If it starts to hurt too much, I can always stop, and my partner will understand. With practice and relaxation, it may even become pleasurable for me.”

Automatic Thought #2: “My partner might think I’m not good at this or that I’m not attractive if I mess up.”

Evidence For:

• I feel insecure about my inexperience, and I worry about being judged.
• Porn often portrays everyone as perfectly experienced, which makes me feel like I need to be perfect too.

Evidence Against:

• My partner has shown me patience before in other contexts.
• Everyone starts somewhere, and most people are understanding about learning curves when learning a technical skill.

Balanced Perspective:

• “My partner is with me because they care about me, not because they expect me to be perfect. It’s okay to be new at this, and I can learn at my own pace. If I communicate openly, my partner will likely be understanding and supportive.”

Automatic Thought #3: “What if I end up embarrassing myself somehow?”

Evidence For:

• I’ve read or heard that accidents can happen sometimes when bottoming.
• I worry about not having complete control over my body, which makes me anxious.

Evidence Against:

• Most partners understand that these things can happen, and it’s a natural part of intimacy.
• I can prepare beforehand, like eating lightly or making sure I’m comfortable, which might reduce the chances of anything happening.
• People won’t judge me for something that is a normal bodily function.

Balanced Perspective:

• “It’s true that accidents can happen, but that’s part of being human. I can take steps to feel more prepared, but ultimately, if something happens, it doesn’t mean I’m unattractive or unworthy. A caring partner will understand, and it’s not something that has to define my experience.”

The Psychology of Control & Sexual Flexibility

Bottoming requires you to let go of control, both physically and emotionally. This can be terrifying, especially when your brain tells you that letting go is dangerous. Ironically, it’s by relinquishing control that you can actually regain it — by relaxing, trusting your partner, and letting go, the experience becomes less about survival and more about pleasure.

Sexual flexibility is a crucial tool in achieving this mindset. Flexibility means being adaptable when navigating sexual experiences — being able to go with the flow rather than needing everything to happen in a specific way. People who are more flexible about their sexual scripts experience less distress when things don’t go perfectly. For example, if you’re used to a specific position, try switching roles or altering the pace. Let your partner take the lead for a while, and see how it feels. The goal is to become comfortable with a variety of experiences and to embrace the unpredictability of intimacy.

Learning flexibility takes practice, and it can start outside the bedroom. Let someone else pick where you eat or change your routine a little. Once you start practicing flexibility in your everyday life, you’ll find it becomes easier to let go in sexual contexts, too.

It’s Time for a New Script

We all have a story playing in our heads about how sex “should” go. These are called sexual scripts, and they’re often filled with ideas about power, control, and vulnerability. You might think, “Bottoming means being submissive,” or “If I bottom, I’ll lose control.” These thoughts come from societal expectations, past experiences, and what we’ve been taught to think about sex.

But these scripts aren’t set in stone — you can rewrite them. Start small. If your current script says, “Bottoming is scary, and I’m going to lose control,” rewrite it to say, “Bottoming is an act of trust, and I choose to trust my partner.” Or, perhaps: “Bottoming is a form of power, and I’m ready to own that power.” Changing the script changes the experience. It’s not just about what’s happening down there; it’s about what’s happening in your head.

Power, Pleasure, and Positions

In the queer community, there are still assumptions about what it means to top or bottom. “Real men top,” they say. But let’s take a moment to laugh at how outdated that is. Who says “real men” only do certain things? That’s like saying “real men only eat steak” — it’s ridiculous.

Bottoming doesn’t diminish your masculinity or femininity. In fact, being the one who chooses to let someone in can be incredibly empowering. Bottoms are often stereotyped as submissive, but bottoming can be an act of power. You decide who enters, when, and how. If you’ve hesitated because you don’t want to feel “less than,” remember that being a bottom doesn’t strip you of power — it amplifies it.

Taking charge of the situation before you get to the bedroom can also be empowering. Set the pace, discuss your boundaries, and communicate your needs. Bottoming is about managing control in a way that works for you.

Being a Side: Alternatives to Penetration

Not feeling the whole top/bottom dynamic? Guess what: you’re not alone. There’s a whole category of men who don’t engage in penetrative sex at all — they call themselves SIDES, and they’re having just as much fun, thank you very much.

Sides prefer intimacy without penetration, focusing instead on oral sex, mutual masturbation, kissing, and other forms of connection. This isn’t a lesser form of sex — it’s just a different kind (Kort, 2019). And for some people, it’s the perfect way to maintain closeness without dealing with the anxieties or discomfort that can come with bottoming.

Being a side is a perfectly valid sexual identity, and it deserves to be recognized. If bottoming just isn’t your thing, or you’re not ready for it, that’s totally fine. There are plenty of ways to connect with your partner that don’t involve penetration.

If you and your partner both enjoy non-penetrative sex, explore it fully. Mutual masturbation, oral sex, and other forms of play can be just as satisfying, and they might even bring you closer emotionally because you’re not tied to expectations about “how sex should go.”

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The Trust Factor: Before, During, After

At the core of bottoming is trust. Trust with your partner is built over time, through open communication and shared experiences. It doesn’t just happen before or during sex; it extends into what happens afterward too.

Aftercare is about maintaining that emotional connection after sex is over. It reinforces positive emotional experiences, helping both partners feel safe and reducing post-sex anxiety. Aftercare could be cuddling, talking about what you enjoyed, or simply holding each other. It’s these small gestures that make both of you feel secure and cared for. Communicating before, during, and after sex ensures that both partners’ needs are met and that a sense of safety is sustained throughout.

Make it a habit to check in with your partner at regular intervals. You don’t have to wait until something goes wrong to have a conversation about trust and safety. The more you talk, the more comfortable you’ll both feel.

When Bottoming Hurts: Let’s Talk Pain, Prep, and Solutions

You might have been cruising through life, enjoying your role as a top, or sidestepping penetrative sex altogether, when suddenly — wham! Your partner gives you the look that says, “Maybe it’s time you try bottoming.” But if you’ve ever tried it and experienced pain, that suggestion might make you feel like you’d rather walk across hot coals.

Pain during bottoming is more common than you might think. In fact, nearly 12–18% of men who engage in receptive anal sex report chronic pain, a condition known as anodyspareunia (Grabski & Kasparek, 2020; Damon & Rosser, 2005). Whether it’s the result of muscle spasms, a too-tight sphincter, or a lack of proper preparation, pain can turn what should be a pleasurable experience into something you dread. But before you swear off bottoming for good, let’s break down the reasons behind the pain — and more importantly, how to make it better.

Anatomy Lesson: It’s All About the Sphincter

First things first: let’s talk anatomy. The anus is controlled by two key muscles — the internal and external anal sphincters. These muscles are like the bouncers of your club (aka your butt). The external sphincter is the one you consciously control, and it’s pretty chill. The internal sphincter, though? That guy has some serious control issues. It’s the automatic muscle that can clench tighter than your grip on a roller coaster when it senses something coming its way — whether that’s a partner or something else (Grabski, 2023).

The challenge? You can’t directly control your internal sphincter. It’s like trying to control your heartbeat — it does what it wants, when it wants. And when your internal sphincter freaks out, you can experience pain, tearing (ouch), or just general discomfort.

Pain during bottoming can stem from a lot of things. It might be physical, emotional, or some gnarly combination of the two. Here’s a breakdown of the most common culprits:

1. Tension: If your muscles are tense (either from anxiety or inexperience), your internal sphincter will clench up, making it harder for anything to enter smoothly. For tension, try practicing progressive muscle relaxation (PMR) before sexual activity (Grabski & Kasparek, 2020). This involves tensing and then slowly releasing different muscle groups in your body, which can help you become more attuned to your body’s tension levels and release tightness gradually. Pairing PMR with deep breathing exercises can make it easier to stay relaxed when the time comes.
2. Lack of Lubrication: Not enough lube is a recipe for discomfort. Make sure you’re using a high-quality, long-lasting lube (silicone-based is a favorite). The key is: if you think you’ve used enough, use more.
3. Improper Prep: Bottoming without preparation is like running a marathon without stretching. Take the time to properly douche if that’s part of your routine, and manage any anxiety about potential mishaps (poop). Preparation is key to feeling confident.
4. Past Trauma: Anxiety often manifests in the body, leading to tightness and discomfort. Addressing past trauma through therapy, and working on reframing negative thoughts, can help you approach bottoming with less anxiety.
5. Medical Issues: Conditions like hemorrhoids, fissures, or anodyspareunia can make bottoming uncomfortable. If you’re consistently in pain, it’s worth checking in with a proctologist or a specialist to rule out any underlying issues (Grabski & Kasparek, 2020; Hollows, 2007).

Anal Botox: Game Changer or Just a Trend? Botox can be a game-changer for those who experience significant pain during bottoming due to overly tight sphincter muscles. Dr. Evan Goldstein, a proctologist known as the “Bottom Whisperer,” swears by it. He uses it to help his patients relax their overly tight sphincters, making bottoming a more comfortable experience (Goldstein, 2023).Botox injections relax the internal sphincter, making penetration easier and less painful. It’s a quick procedure that can make a big difference. However, Botox isn’t a permanent fix — it wears off in 3 to 6 months. There are also rare risks, such as minor incontinence or discomfort at the injection site, so it’s important to weigh the pros and cons with a specialist.

For those considering Botox, pairing it with a dilation routine — a series of exercises using anal dilators — can provide the best long-term results by helping to stretch and relax the muscles gradually.

If you do decide to go the Botox route, pair it with a dilation routine — a set of exercises using anal dilators to gradually stretch and relax your muscles. This combo has been shown to provide the best long-term results for people struggling with tightness (Grabski, 2023).

How to Set Yourself Up for Success

Preparation is everything when it comes to bottoming. Think of your body as a finely tuned instrument that needs some warm-up before it’s ready to perform. Here’s a quick guide to set yourself up for success:

1. Silicone Lube: Get yourself a high-quality silicone-based lube for its long-lasting properties. The more lube, the better — it minimizes friction and makes the experience far smoother (Damon & Rosser, 2005).

2. Start Small: Start with something smaller, like a finger, a small toy, or a butt plug. Gradually work your way up, giving your body time to adjust. This helps you become more comfortable with the sensation of penetration (Grabski & Kasparek, 2020).

3. Dilate Regularly: Whether you’re using Botox or not, dilation can help immensely. Use anal dilators of increasing sizes to gently stretch the muscles over time. This gets your body used to the sensation and helps reduce tension (Grabski, 2023).

4. Breathing and Relaxation: Deep breathing can help relax the stubborn internal sphincter. Practice breathing exercises during your play or dilation sessions to keep both your body and mind calm.

5. Communication with Your Partner: Have an open conversation before any penetration. Start by explicitly stating your boundaries and what you’re comfortable with, and then invite your partner to share their feelings too. Address potential concerns, such as “What do we do if there’s unexpected poop?” This mutual sharing helps create a safe environment, and setting clear expectations will help ensure both partners feel respected.

6. Douche and Mental Preparation: Flushing your rectum with water will increase your confidence. Alongside douching, take some time to mentally prepare. Use affirmations like ‘I am prepared and in control’ to help reduce anxiety about the process. However, remember that despite preparation, the possibility of poop might still arise, and that’s okay. Managing your anxiety, shame, and any discomfort around this possibility is a crucial part of feeling at ease.

Embrace Aftercare: The Overlooked Secret to Intimacy

Just because the sex is over doesn’t mean the intimacy has to end. Aftercare is an essential (and often overlooked) part of the bottoming experience. It’s crucial because it reinforces positive emotional experiences, helping both partners feel secure and reducing any post-sex anxiety. Whether you’ve had an intense, emotional session or just a casual romp, reconnecting with your partner afterward helps reinforce trust and intimacy. This could be through cuddling, talking about what you enjoyed, or simply holding each other. It’s these small gestures that make both of you feel safe, cared for, and connected.

Aftercare can be as simple as cuddling, talking about what you enjoyed, or even just holding each other. It’s not about the grand gestures — it’s about making sure you both feel safe, secure, and cared for. Plus, it’s a great way to debrief and strengthen your bond (McDonagh et al., 2014).

And, don’t forget the practical side of aftercare — clean up with a gentle, soothing wipe and hydrate. Your body (and your butt) will thank you.

Bottoming is a Journey, Not a Destination

Bottoming isn’t something you master overnight. It’s a journey — one that is sometimes challenging but ultimately rewarding. Whether you’re new to it, coming back after a break, or trying to improve your experience, remember that each experience is a chance to learn. Stay curious, communicate openly with your partner, and give yourself grace as you figure things out.

There will be bumps along the way (pun intended), but with a little preparation, a lot of lube, and a good sense of humor, bottoming can become one of the most empowering and enjoyable experiences you ever have. Remember: this is your body, and you make the rules. You’re not “defective” for needing to take your time or for navigating through someone else’s fantasy world at your own pace. This is your journey — own it, and make it yours.

References

Damon, W., & Rosser, B. R. S. (2005). Anodyspareunia in men who have sex with men. Journal of Sex & Marital Therapy, 31(2), 129–141. https://doi.org/10.1080/00926230590477989

Grabski, B. (2023). Treating anodyspareunia in MSM. Erotically Queer, 156–173. https://doi.org/10.4324/9781003260608-11

Grabski, B., & Kasparek, K. (2020). Sexual anal pain in gay and bisexual men: In search of explanatory factors. The Journal of Sexual Medicine, 17(4), 716–730. https://doi.org/10.1016/j.jsxm.2020.01.020

Goldstein, E. (2023). The surgeon general of bottoming: Anal Botox and proctology for better sex. Journal of Queer Medicine, 45(3), 192–207.

Hollows, K. (2007). Anodyspareunia: A novel sexual dysfunction? An exploration into anal sexuality. Sexual and Relationship Therapy, 22(4), 429–443. https://doi.org/10.1080/14681990701481409

Kort, J. (2019). Is there a side to gay sex you haven’t heard about? Psychology Today. Retrieved from https://www.psychologytoday.com/us/blog/understanding-the-erotic-code/201905/is-there-side-gay-sex-you-havent-heard-about

McDonagh, L. K., Bishop, C., Brockman, M., & Morrison, T. G. (2014). A systematic review of sexual dysfunction measures for gay men: How do current measures measure up? Journal of Homosexuality, 61(6), 781–816. https://doi.org/10.1080/00918369.2014.870452

Moskowitz, D. A., Rieger, G., & Roloff, M. E. (2008). Tops, bottoms and versatiles: Sexual self-labeling, gender roles, and sexual scripts among gay men. Sexual and Relationship Therapy, 23(3), 191–202. https://doi.org/10.1080/14681990802027259

van der Kolk, B. (2014). The body keeps the score: Brain, mind, and body in the healing of trauma. Viking.

Yessick, L. R., Gauvin, S. E. M., Salomons, T. V., & Pukall, C. F. (2022). Pain characteristics, sexual script flexibility, and penetration control cognitions in those experiencing anodyspareunia. Psychology & Sexuality, 14(1), 321–336. https://doi.org/10.1080/19419899.2022.2118069

Zheng, L., & Zheng, Y. (2016). Sexual satisfaction in Chinese gay and bisexual men: Relationship to negative sexual minority identity and sexual role preference. Sexual and Relationship Therapy, 32(1), 75–88. https://doi.org/10.1080/14681994.2016.1200027

This essay was first published on Medium on October 4, 2024.