How quarantine made me a better bottom

As a sex writer, I’m fortunate to receive new sex toys on a fairly regular basis for reviewing purposes. Having written on the subject for nearly a decade, I’ve amassed a sex toy collection that rivals Christian Grey’s.

The volume is overwhelming, so I’ve donated some of these provocative playthings as stag and doe prizes and gifted others during the holidays. The remainder are stored in backpacks shoved deep in my closet (where I also spent the majority of my 20s).

But with COVID-19 keeping us indoors and at least six feet apart, my closet doors have inched open—no doubt a response to circumstantial loneliness. When we were first told to isolate, my roommate fled the city to spend time with his girlfriend (the two recently purchased a puppy). Now I’m alone, re-watching the Real Housewives and taking physically-distanced walks to break up my day, strutting to Lady Gaga’s Chromatica.

My boyfriend lives hundreds of miles away in New York City and my libido has been craving something more substantial than my left hand. It wasn’t long before this mounting sexual energy swept me from my poorly assembled IKEA bed toward the closet, where I reached for my two grade-school backpacks and a large suitcase filled with a colourful collection of phallic-shaped devices and tangled charging cords.

I dumped them out and examined each toy. There must have been a hundred. To better manage the collection, I tossed the novelty toys aside (there isn’t much regulation regarding body-safe chemicals in adult toys, so “novelty items” can contain harmful materials), as well as the masturbations sleeves (I’ve never been fond of them, TBH), until I was left with lube and butt toys. Prostate massagers, dildos, vibrators, dilation kits—I had them all.

Admiring the medley spread across my bedroom floor, I concluded that I was going to master each and every one of these toys—both to reach that next-level climax I’d been craving, and to proactively prep my body for the day we’re able to have sex with individuals outside of the home.

I’ve used anal toys on occasion in the past, but I found them time-consuming. Between the douching, the lubing, the dilating and the cleaning, I just didn’t have the energy for it. My libido is a demanding mistress and she doesn’t wait for no man—or toy.

My relationship with bottoming has always been complicated and a major source of insecurity. As somebody who is sexually versatile (which means I’m open to being both the insertive and receptive partner), I often assume the top—or side—role because it’s where I feel most adept. I want to bottom more than I do, but for me (and many men who have sex with men), receptive anal intercourse doesn’t always go over well.


Sometimes, my experiences with anal sex is pure, toe-curling euphoria that I wish would never stop. Other times, it feels like I’m being gutted and things can’t end quickly enough. As a result, I’ve always felt that, if my bottoming skills aren’t up to par, I should assume the position that I’m more confident in even if it doesn’t necessarily match my desires.

Now, with nothing but time, I was finally going to learn how my body best responds to receptive anal sex, and do so at my own pace.

As one should, I started small with butt plugs no bigger than my index finger. As it had been a while since I last bottomed, insertion was uncomfortable at first, so I used a healthy dollop of lube and re-applied often. I gradually upgraded to a slightly larger size every two days or so (this is why dilation kits are so great) and if I felt resistance, no biggie, I’d stick with my current toy for another day or two.

Did I make mistakes? Yes. There were moments on my journey where I got too confident and there was blood (though very minimal). This is fairly common; the bum is very sensitive, even when taking all possible safety measures. (I would recommend being completely sober when training, as any substances that may be used to ease discomfort can also mask pain and signs that you’ve gone too far.)

In the beginning, my body responded best to butt plugs—once they’re in, they’re in, and, well, that’s about it. The majority of plugs have a thin tip, a wide centre with a notch to hold it in place and a flared base to prevent complete insertion into the rectum. A butt plug gets your body comfortable with a fullness that your bum doesn’t often experience, and in that way it’s a fantastic tool. But in terms of penetration, it doesn’t have much to offer. As I started feeling more confident, I’d insert a plug before going out to grab an iced coffee. The experience, while a little uncomfortable at first, was deliciously taboo and I highly recommend it.

As my body gradually got used to plugs, I felt comfortable moving on to prostate massagers. These toys, with a shape similar to a finger, usually have a slightly curved head to effectively massage the prostate (or “P-Spot”), a muscular gland that produces the seminal fluid in ejaculate. The prostate, located roughly two inches inside the rectum, is covered in nerve endings, and those who stimulate this gland claim their orgasms are 33 percent more powerful.

I started small and slow: I pushed the toy deeper until it was completely in, then I pulled out, re-applied the lube as needed, and repeated. After I opened up, which didn’t take long, I decided to turn on the toy’s vibration setting and the rest is history. My toes curled and my back arched as pleasure-induced muscle spasms surged through my body. As I descended from that heavenly orgasm, I felt accomplished, like I had achieved what I set out to do.

But to fully honour the task, I continued working my way through various dildos and vibrators as well, but found them less fulfilling because, in my mind, I was already in an exclusive relationship with my prostate massager.

I’ve been alone since the pandemic started, so I’ve convinced myself that the amorous feelings I’ve developed toward this inanimate object is not pathetic; instead, it’s a glimmer of hope when things feel hopeless.

I’ve been able to do things with my ass that I never thought were possible, which—in addition to giving me incredible orgasms—is brewing a new confidence in me, one that never existed prior. I’m hoping this feeling will no longer convene in my reluctance to bottom, but only time will tell.

I can honestly say this experience has opened my eyes (among other things) to the full spectrum of pleasure one can glean from anal intercourse. Needless to say, there are no longer toys hidden in my closet: They’ve instead become trophies of personal accomplishments that I likely wouldn’t have achieved under other circumstances. This pandemic has given me time to explore anal stimulation on my own terms, separate from the pressure and insecurity of in-person encounters.

I don’t know—maybe I’m too excited about something mediocre. It’s difficult to find something to be grateful for or to accomplish during this scary time, so I’m going to ride this wave for a while (fittingly, my favourite toy is called the LOKI Wave).

As businesses begin to open their doors and rules are cautiously lifted, I will emerge from lockdown as a new man with a skilled b-hole. Isolation is hell, but the circumstances have helped me get to a place where I can confidently—and comfortably—explore sex in ways I wouldn’t have otherwise—particularly bottoming. So I’m going to celebrate.

Now, if you’ll excuse me, I have a date with a butt plug and some iced coffee.

Bobby Box

Bobby Box is a queer writer and certified sex educator in Toronto whose work has been published in Greatist, Playboy, Elle Canada, Toronto Star, NewNowNext, Them., The Advocate and more.

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