I’m famously a bottom. I have been for several years—ever since I was 16, rummaging my finger around my trunk like I was looking for change in couch cushions. But when I actually started having sex, I couldn’t bring myself to “sit on it” like the good boy so many men were telling me I was.
This isn’t a new or interesting fear. A lot of gay men abstain from anal sex for a variety of reasons. For me, my bottoming anxiety came from the pain I experienced the first few times I tried it. When I started having sex, I was 17, and the tops that were trying to break my seal weren’t the sharpest pencils in the pencil case: they had untrimmed fingernails, lacked quality lube, and were disgusted by the idea of eating ass. (I really knew how to pick ’em back then.)
Because of this, I spent my peak twink years—featuring a 27-inch waist, skeletal body, and thick butt thanks to my Greek heritage—being a top. A terrible, terrible top. I sometimes lay awake at night thinking about all the hot dads I turned down because of my fear of bottoming. All because I didn’t have the courage to buy a butt plug.
I always figured my butthole would be “too tight” to be fucked properly. But through my recent years of experience, I’ve learned that everyone has a tight butthole! That’s how it’s supposed to be! Your butt is a muscle meant to push...stuff out of it. (I love how I freely talked about fingering myself, yet I draw the line at the word “poop.”) You don’t run a marathon without stretching, so why go into a marathon sex session with your butt as tight as a can of tuna? And though this reasoning may sound obvious to some, it’s something I never considered when I first became sexually active. I blame porn for not having enough behind-the-scenes content. We could really use an OnlyFans that just offers professional advice on how to stretch out our holes.
Unless you’re keeping your hole stretched out by getting plowed by someone on the regular—in which case, God bless—you should take the initiative to keep it stretched out. I feel an appropriate phrase is “use it or lose it,” but I think “loose it or lose it” is more appropriate. It’s like a pierced ear: once you start getting anally penetrated, you have about a day before your hole closes back up and you need to get pricked again. Treat your butt plug like the stud earring that’s used to pierce the ear and keep it in until you’re ready to upgrade to something flashier (or fleshier).
If you’re thinking about getting a butt plug, you’re going to have to go to a sex shop. Buying sex toys, especially ones that go up your butt, can feel like an awkward thing to approach. While I now have the confidence to walk into a sex shop and talk to the fine service people about my needs, it was overwhelming and terrifying when I was still figuring out my own butt journey. Talking to strangers about your sexual needs takes some getting used to, but it isn’t too different from a lengthy sext exchange. At least this way, you get useful information on how to set yourself up for properly fulfilling your pleasure, and your secrets have less of a chance of being posted on r/grindr. Don’t go buying butt plugs on Amazon—shop local and get good products. Jeff doesn’t need to know your business any more than he needs your money.
I own several things reserved for the entrance of my exit. They vary in length and thickness, but none of them are longer than five inches. Nowadays, I reserve these silicon buddies for when my boyfriend is away and I want to keep myself in prime bottoming shape. But there was a time when all my buddies got a turn keeping me company while I was on the go and about town.
That’s the beauty of a butt plug versus a dildo. While you can use both to simulate anal sex, the butt plug is dual purpose. You can just pop it in and it’s designed to stay there. There are also fun designs you can add to the “plug” end: some have a horse's tail or bedazzled gems, are inflatable, have USB storage, or even provide fidget spinner attachments for when you get bored. It’s about function and form.
Sporting a butt plug in day-to-day life came to me where most great sex ideas come from: a random man on Grindr. I mean, this random stranger later became my ex-boyfriend, but that’s how all good relationships should start.
Soon into our relationship, he introduced me to his training dildo set. He called them his “little friends,” though some of those friends were anything but little. It took a few weeks to get into the rhythm. I would put one in, we’d go on our date, and by the time we came back I was open for business. When we broke up, I bought my own set of butt plugs and kept up the tradition, because I’m nothing if not sentimental.
I certainly never got any complaints from the men I was sleeping with; most of them liked the little surprise of finding out I’d been keeping myself wide. It was less work for them and showed how dedicated I was to their fun.
At the end of the day, I don’t trust tops to open the door for me—let alone my hole. Aggressive sex can lead to unwanted tearing, and it can be a real mood killer when you have to pause the whole event to assess the damages.
I don’t think butt plugs should be something we’re afraid of using on a weekly if not daily basis, especially as gay men. While lube is an important part of intimacy, it shouldn’t be the only tool in the kit. Anal sex can be a messy, painful experience, and if the first thing you’re putting up your butt is a dick, it can feel overwhelming. So start small and set yourself up for success. Your butt is beautiful inside and out—so stick something in it and live your best life.