What to Expect When You’re Expecting to Bottom

how to bottom

I had my butt surgically replaced with a larger one. At least, that’s what I told my friends. Then again, a doctor put me under and sliced my sphincter, so it’s closer to the truth than you’d think.

In my early 20s, I developed an anal fissure. If you’re not aware of what a fissure is, I’m envious of you. It’s a tear in the thin tissue that lines the anus. Yes, anal sex is one of the common causes, but others include straining during bowel movements, childbirth, and chronic diarrhea. Fissures can affect a person of any gender or sexual orientation. Given the importance of anal sex in the cis gay male community, the focus of this article is on their (and my) experience.

A Lack of Sexual Education Hurts Gay Men


I don’t know exactly when I got my anal fissure because I didn’t know the right way to have anal sex. I grew up in Texas where, after one assembly about sexual health, we were asked to sign an abstinence pledge. (I did.) So, of course, there was never any education on anal sex or gay-focused content. And Texas isn’t alone. According to the Guttmacher Institute, only 10 states require inclusive content about sexual orientation, while, surprisingly, 7 states require negative information on being gay. It’s no wonder I had to learn about sex from gay porn, which is where unrealistic expectations start for many of us. I also learned from my gay friends, who themselves learned about it from gay porn. Finally, as I started to have sex myself, I learned about sex from my partners, which didn’t turn out well for me.

Questions to Ask Before You Have Anal Sex

Rather than jump right into how it’s important to start with self-reflection. The first question is, do you actually want to have anal sex? And if so, why? There’s pressure in the gay community to have anal sex. It may feel like it’s a requirement for any hookup or relationship. It’s not. There’s a difference between romantic interest and sexual interest. Asexual people, or aces, experience little to no sexual attraction, but can still have a romantic interest in the same gender. You don’t need to have any interest in anal sex, or sex at all, to be in a happy and fulfilling same-gender relationship.

Even if you do experience sexual attraction, anal isn’t a requirement. We talk about top, bottom, and versatile as if those are the only options. They aren’t. “Sides” are men who don’t prefer and often don’t have anal sex. Take anal sex off the table, and there’s still plenty of fun to be had. Sex is not defined by penetration. (And from one non-side gay man to the others, side shaming isn’t cute. Stop it.)

You don’t need to have a definitive answer to these questions. In fact, your feelings may change over time. If you know you want to have anal sex, or are curious about it, learn how. It’s okay to experiment. It’s okay to decide it isn’t for you, even if that means stopping in the middle of it and walking away. Explore if and how you want to.

The Myth of Pain

The biggest lie I believed is that I should expect pain. I was fortunate that my first experience bottoming was with someone I trusted, and he helped ensure I was safe and enjoying myself. (I was.) I remember, weeks later, a female friend asked me and our mutual friend, also gay, if it hurt. I immediately said, “no, not if you do it right.” At the same time, my gay friend replied, “yes.” We looked at each other. He was more experienced than I was, so I believed him. A lack of education, combined with my lack of self-confidence, meant that I had the right information but didn’t know it at the time. I believed him when he said to expect sex to be painful.

This belief was compounded by the partners I had sex with. It was common for them to tell me, “relax,” as if that ever helped anyone. One of my friends with benefits said to me during a particularly painful encounter, “you can take a lot more than you think.” What I heard was, “stop whining.” I wanted to enjoy it, and gay men expect it, so I kept trying. It never changed. Sex ranged from uncomfortable to flat-out painful.

My Body Is Different Than Most

After bottoming (incorrectly) for years, I was confused. Maybe I just don’t like to bottom. But then why do I still want to? And then I’d try again, and I still wouldn’t like it. Maybe there’s something I’m missing. Maybe this is just how it feels. Maybe I’m just whining. Maybe there’s something wrong with me. All the while, my gay friends talked about the fun, hot, steamy sex they had. Their stories sometimes overwhelmed me. It seemed all too easy for them. What’s wrong with me?

As it turns out, my body worked very differently than theirs. When I got my fissure, I tried all of the non-invasive options I could: sitz baths, topical creams, and nitroglycerin. None worked. My doctor referred me to a specialist. When she was examining me, she informed me that I had a “very tight sphincter.” It was an uncomfortable thing to hear while her finger was inside me. But this realization was vital. I am tighter than most people. Not in a fun, hot, sexy way either. In a way that explained why I never enjoyed bottoming. It explained why everyone expected me to just “relax.” They didn’t understand my body, either. My fissure was treated by a surgery called a lateral internal sphincterotomy, which I was come to refer to as my butt replacement surgery. In the procedure, the doctor cut one side of my sphincter, which releases the pressure and allows the fissure more “breathing room” so it can heal. After that surgery, I had to re-learn how to have sex. While I’m not a doctor or sex therapist, I’d like to share what I’ve learned in my journey toward fulfilling sex.

Start By Exploring On Your Own

beautiful man laying on bed

It can be tempting to want to start exploring with a partner. After all, climbing Mt. Everest is way more exciting than walking up a hill. But fulfilling sex starts by understanding your own body. I started exploring on my own. Without tools or penetration, rubbing the outside of my anus or the perineum (the area between the testicles and anus) felt good. When I was ready for penetration, a finger was an easy way to start because I have complete control over it and where it goes. Lube is key and should be applied liberally to your finger and butt. I used my pointer finger and started slow, a little at a time. If it ever hurt, I would stop and add more lube. I tried not to move forward until I knew I was ready. It was slower than I expected, and that was the key that I had been missing. Once I was ready, I would go deeper or add more fingers. For some, this is a good time to find your prostate. For me, this was a more advanced move I didn’t learn until later as it takes some poking around and understanding yourself to get there. Masturbating during this exploration helped establish a connection between pleasure and anal play, and it also felt better than masturbation alone.

My next step was to get a sex toy. I was skeptical that I’d be able to use or enjoy anything, but I went with a friend to a sex store, and he helped me find a butt plug. I selected the smallest one I could find, which had a circumference of roughly 3 inches at its widest point. I was surprised that, even with my medically-verified tight sphincter, I was able to put the butt plug inside me easily with a minimal warm-up. I like butt plugs because they have stoppers at the end so I didn’t have to worry about getting anything lodged inside me, which Grey’s Anatomy has led me to believe is very common. If it’s not going in easily, I either go back to using a finger or only use the tip of the butt plug, which should be very small. Once I’m warmed up enough to place it all the way inside me, I often leave it there while I go about my regular masturbation routine. Again, having something inside you while experiencing pleasure and orgasming is a useful association to make, and it can make orgasms feel even better, even without manipulating it.

Butt plugs come in graduated sizes, and I use them to work up to bigger and bigger sizes. Even today, I still start with the smallest one as a warm-up and build up to the bigger ones. I’ll sometimes work up in size as I’m masturbating by myself. More often, I use the graduated butt plugs to warm up for sex. Sometimes, I’ll use them on my own before I meet up with my partner if I want to jump right in. I’ve started to use them with a partner as a regular part of foreplay. I’ll set out the graduated butt plugs in preparation for sex. In my experience, not only are guys willing, but they are excited to use them with me. It gets me ready for them, and it builds up the excitement.

Yes, Mental Health Is Important When Bottoming

Before I get too deep into anal sex with a partner, let me take a step back. This part is exciting. It’s fun. It’s hot. It’s also complicated. You’re not just adding a penis to the equation. You’re adding a human being with their own feelings, expectations, and intentions. This is where therapy and self-improvement played an important role for me. It may sound odd to bring up mental health in a discussion about how to bottom, but I can’t overstate how important it has been in my growth. I am working on my assertiveness, which helps me stop a sexual encounter if it doesn’t feel right, even if that means angering my partner. I’m more in tune with my body. I define clear expectations and boundaries. More and more, this includes a direct conversation about my tight butt. I do it in a way that is both flirtatious and direct. I make it clear that it’s not a joke or a brag. Most times, it’s a non-issue. On occasion, I’ve ended a conversation on Grindr because it was clear he wasn’t willing to listen and take it slow.

Finally, the Actual Anal Sex

how to have a prostate orgasm

Once I’ve loosened myself up with the butt plugs, I start with the unfortunately-named cowgirl position. (Cowperson position doesn’t roll off the tongue.) My partner will lie down on the bed, or couch, or rug, or backset, allowing me to get on top of them. I get to control the situation. Either or both partners may be excited to get to the full-blown penetration, but it’s important to continue taking it slow. I tend to put his penis inside me and ride just the tip of it. As I get more and more comfortable, I’ll go further and further down, taking more and more of it. My partners sometimes instinctively start to thrust their hips, but I tell them directly that I need to continue to be in control until I saw otherwise. During this process, I’m typically able to sit all the way down, taking their full penis. I enjoy sitting, without moving, on top of them as I continue to relax and get used to the sensation. This is a fun time for kissing or tightening and then releasing my sphincter muscles for added sensation. The slower I go during this process, the more relaxed and comfortable I am, and the better the rest of the sex will be.

I see the “cowgirl” position as a good litmus test. How receptive (sorry about that one) is my partner with me taking things slowly? Does he listen and respect me during this? Am I sufficiently warmed up? Does it feel good? If it’s not feeling right, this is a good point to stop and re-evaluate. That could mean going back to the butt plugs to loosen up more. It could also mean opting for other, non-anal activities, or even ending the sex right then and there. Telling someone you need to stop can be uncomfortable, at least it can be for me. But trust me. Dealing with that discomfort is a million times better than dealing with an anal fissure. If I’ve gotten to this point with my partner, all bets are off. I’m ready to switch positions, let him take control, and have the fun, exciting sex I had only dreamed was possible. In fact, the sex I have from that point on isn’t so different from the sex I was having before, at least not mechanically. The difference is I’m ready for it now.

Pain Is An Important Signal During Sex

Yes, anal sex can be uncomfortable. There can be a feeling of pressure. But it should never be painful. This is why you should never use numbing lubes. Pain is an important sensation. It’s your body’s way of letting you know you need to stop. Listen to your body, and speak up for yourself. In my experience, simply saying “that hurts too much” is enough for my partner to immediately stop what they’re doing. However, if your partner gives you any pushback after this, you should probably end it with them and throw them out. He should want both of you (or all of you) to enjoy the experience, not just himself.

Enjoy The Process

During this exploration process, you should learn about yourself. I’ve felt excited, nervous, turned on, confused, and almost any other emotion available to me. As you experiment, you’ll learn what you like and what you don’t. It’s okay if that means you discover you don’t like anal sex, or sex at all. It’s okay to change your mind. It’s okay to change it back. At the same time, it’s okay for you to love it. It’s okay for you to want it. It’s okay if your experience is entirely different than mine. Listen to yourself, trust yourself, and respect yourself. Ultimately, I’m not disappointed I got a fissure. I’m disappointed I didn’t know how to bottom. I’m grateful that I’ve learned. So. So. Grateful.

Kyle is the co-host of Gayish, three-time nominee for Best LGBTQ Podcast. Kyle’s writing has been published in literary journals such as The James Franco Review, Arkana, and Cat on a Leash Review. More info available at kylegetz.com.