Learning to Date My Dildo

Opening my heart (and ass) to a new type of isolated pleasure

I recently had some exciting sex during quarantine. No, I haven’t breached our nationwide social-distancing contract by meeting up with fuck buddies or my boyfriend. Nor have I propped up a sheet with a hole cut in it on my rooftop and taken anonymous loads through it, thereby avoiding any infected respiratory droplets. And while it’s true that I’ve been begging my roommates to spoon me to satisfy my desperate need for physical intimacy, that’s not what I’m talking about either. 

I recently had a very romantic date with my dildo.

My dildo’s name is Dawn, like the dish soap with which I wash it before and after. Alternatively, it can be spelled Don — like a mobster boss who loaned me money that I want to repay “some other way.” It’s obsidian black, made of a firm silicone and measures seven-and-a-half inches long with a six-inch girth. I like all kinds of cocks, but this one’s perfect. We met back in college, and we’ve had an extremely casual thing ever since. I don’t need what Dawn gives me on a regular basis. So when we hook up, it’s usually a special occasion. 

Those occasions tend to be late, late at night when I’ve said yes to various bathroom stall offerings, but wound up back at home alone and have to stop myself from inviting over an equally blasted stranger. Ravenously, I tear open the top dresser drawer and rekindle my most long-standing sexual relationship in a sloppy fit of self-pleasure. I feel a little depraved and a little desperate as it’s happening, but mostly, I feel relieved. 

The other evening, though, was different. It’d been a gay decade (a month) since a phallus penetrated me. As I got very stoned, I could hear the slow trickle of time under quarantine and the whimper of my prostate begging like a dog at the dinner table. I knew I had a perfect window for prolonged masturbation. But I also felt uneasy about playing with Dawn before dusk. I wanted things to be nice this time.

As such, I felt obliged to douche for my dildo, especially with all that time on my hands. For a man, I usually don’t bother. They can deal with my shit. That said, I usually do end up wishing I had douched. Not because I love the process of douching, but because I love the feeling of being rinsed. When you’re not speed-purging while a stranger with a fragile erection waits alone in your bedroom, it’s quite relaxing.

I took my time with my shower shot. I’d just bought one a few months ago after years of exclusively using a bulb douche, and I was just beginning to get used to its more efficient approach. But as I got comfortable inserting and removing the thin, smooth shaft of the shower tool, I became prematurely aroused and even a little worn out. I felt my motivation to bottom slip down the shower drain. I’d unknowingly cheated on my dildo. 

What was I supposed to do now? Walk back into my room and tell my dildo I wasn’t in the mood anymore? 

Overall, I felt disoriented attempting to prepare myself mentally and physically for sex with an inanimate object. Which is to say, I didn’t know how to prepare for sex with myself. There was no one with whom to share power and no audience to entertain. My adult sexuality — developed in the density and openness of New York queer life — hinged increasingly on the unpredictability of other people. But alone with total control and privacy, nothing felt erotic. 

I swished some Listerine around my mouth to subdue my self-consciousness. Thankfully, it worked. I was rebalanced, rinsed from both ends. 

Dawn, meanwhile, was waiting patiently, so I continued to set the mood, lighting a stick of incense and putting on the new Dua Lipa album. I started dancing, but Dawn glanced at me suspiciously.

Staring back at Dawn — the ever-patient, perfectly molded cock — I took a breath and decided to keep my mind open to different forms of pleasure than the ones I idealize the most. We started carefully and gradually like I normally do during sex. But without any concern for keeping another person entertained, I could draw out these warm-up stretches for as long as I liked. I moved the toy around and explored for points of pressure and sensitivity. I breathed deeply as if in a yoga pose. Pressing Dawn in and out of myself more carefully and more commandingly than most lovers know how to do, I felt wonderful.

When I finished, I wrapped Dawn in a towel and stared at the ceiling. It made me sad to register how disconnected I’d become in only a few weeks. I struggled and strained for sex, which once felt second nature. There’s a difference between getting fucked by way of a silicone dildo and having a dick inside of you. I don’t know if I want sex without the latter. I want the weight of a living body, its warmth and its sweat. I want to surrender to sex and the power of the person giving it to me, not strain my own arms and legs trying to satisfy myself.

Lately, I’ve seen at-home workouts on the internet propagating like, well, a virus. The people we know for their glamorous vacations and sponsored content are trying desperately to foster some optimism by encouraging us to stay limber. Exercise is a cornerstone of mental health care, so I’m not hating on this effort. I just can’t seem to find the motivation to work on my body when my life lacks both the work and the play for which I need my body to be strong.

In fairness, my date with Dawn was lovely. It just made me feel like a recent divorcee hesitantly trying to get back out there, and in the process, feeling hopelessly out of practice. (Maybe I’ve been watching too much of The Good Wife.) But I also keep telling myself that the point isn’t to fake a sense of normalcy. It’s to open yourself up wider than before.