No. 9 | Bottoms Up!

One of the things that excited me the most about visiting the United States was the possibility of losing my virginity. With the tragic turn that my online dating experience had taken in the last three years, I gave up on the idea that I would find a boyfriend, or at the very least, a hookup, in Manila. Besides, I’ve always had better-looking Tinder matches when I went abroad, and they’ve had more substance than any local I’ve conversed with.

On my 18-hour-flight, I began to fixate on wanting to have sex—real, penetrative, anal sex with a man—for the first time. Sure I’ve had my fair share of encounters, like that blowjob in a school bathroom when I was 16 and that awkward meeting with the Quebecois less than a year before, but I’ve never gone all the way. I was dying to know what bottoming felt like, why some men hated it when it looked like it could make me scream with pleasure. I also wanted to know if I was confident enough to be a top. One of my strangest beliefs was that a top needed to be masculine, and I wasn’t sure if I had that much masculinity in me.


It wasn’t my first time to visit the States, but it was the first time that I felt comfortable enough to try and find a man who would do the honor of deflowering me. I didn’t just feel comfortable; I craved it. It felt a lot like I was missing out on sex.

See, when I was one of the boys back home (read: with my ultra-masc, alpha-male cousins who were right around my age), I always felt left out when they talked about sex. They were womanizers who could have been the subject of one of Carrie Bradshaw’s columns had we been living in New York. They would swap tips on how to make a girl squirt using their tongues, argue about the location of the clit, and exchange phone numbers of girls who were an easy fuck. They presented themselves like sexual masters of the world, and they would always shoot me with a pitiful look that told me either “we know you’re a virgin,” “we know you’re gay,” or both. Not that having sex with a man would solidify my membership in the boys’ club… but something about being with them told me that now was the time to explore.

In a desperate effort to lose my virginity, I downloaded not one but five hookup apps on my iPhone, excluding Tinder because I thought that the latter could be used for finding actual dates. Three of those hookup apps were specific for my body type, somewhere between bear and chub, which was appropriate because I was generally attracted to guys who shared a similar size and weight.

Soon enough, I found a few guys who seemed worth the effort to meet in person. That would have been great, except they wanted to meet me while I was cooped up at two in the morning in my cousin’s Hello Kitty-decorated bedroom, which I temporarily shared with my mom and my sister, in a quiet house in a New Jersey suburb. I didn’t know how to sneak out of the house, nor did I know how to get back in. I knew nothing about the surrounding area, except for the general demographic that it was mostly occupied by Italian immigrants.

Who seemed the effort? you might ask. Well, I wasn’t very choosy because I didn’t want to make losing my virginity such a big deal. For one thing, I believe that it’s a mental notion that is subject to open interpretation; I wasn’t even sure if I was a virgin because I had engaged in oral sex before any of this. Still, if a guy had a job or was enrolled in a major that seemed interesting, he was worth the effort. If I was physically attracted to him (and he had to be physically attracted to me in return), he was worth the effort. If he looked like and he actually said that he would take me out to dinner after having sex, he was worth the effort. Among other things, and most importantly, he had to be clear of STD’s and had to have a place because I surely couldn’t host anyone in a relative’s house. My standards weren’t low for a man whom I would have sex with for the first time. They’re just standard, and that was okay because I wasn’t one to look for a relationship abroad. Those could be messy, especially when one of us realizes that we’ve fallen in love even though we’re eight thousand miles apart.


I didn’t meet anyone until a few hours before I needed to catch a flight heading to Toronto. Growlr buzzed while I was absentmindedly scrolling through Twitter in the bathroom. A doctor named John had sent me a message, and asked why I was on the app. Figuring I would never bump into anyone I talked to after meeting them for the first time, I was blunt and said that I was looking for someone who was interested in virgins. Our conversation lasted no longer than ten sentences, but I did get an address and an invitation to meet that would expire in 20 minutes.

Being the stupid millennial that I was, I quickly WikiHow-ed what to do before having sex  as a bottom for first time. One of the things that highlighted itself in the article was douching. I’ve heard about it from YouTuber Miles Jai, who once did a video of himself trying out sex toys, and explaining briefly the importance of douching. And because I was, by nature, a highly insecure individual, I had to figure out what to do to avoid the shit-on-a-dick situation, sans douche. Just like that, I shoved a bottle of drinking water up my ass and sprayed, giving myself a very wet and liquid preview of the things to come.

Running late, I hopped into an Uber that took me from Riverdale to East Bronx. Taking interest in my Asian appearance, the driver took the opportunity to talk about Filipino politics and our “exotic” food. He got so excited talking about pancit, he missed a turn that now made me 20 minutes late for my date, if that was an appropriate term to describe our meeting.

The receptionist at John’s building took a long look at me before letting me enter, asking me if I would be staying long at the sight of my small suitcase that I was bringing with me to the airport directly after. I politely said no, and descended to the basement level, where his apartment was. I kept ringing the doorbell, but nobody answered the door. I checked my watch to see that I was twenty-five minutes late, and remembered that Americans took punctuality seriously. If I had been in the Philippines, I would still have been early to the date even if I arrived twenty-five minutes late.

Feeling defeated, I went back up to his lobby, but remembered that John mentioned he wanted to get a workout, so I asked where the gym was, now making it clear that I had never met John and that I was there for a quickie. At the gym, I searched frantically, catching the attention of a heavy-set black lady on one of the treadmills. She approached me to ask why I was there. I casually said that I was meeting someone, but that he didn’t seem to be there. We apologized to each other, and I made my way back to the doors when a silver-haired boy approached me.

John looked like a different person from the one I was talking to on Growlr. For one thing, his haircut was far from the dark, clean undercut. His was a merman swoop that explained the silver dye. His glasses, which were absent from his profile, made him unrecognizable. He was also a lot shorter than I had imagined, but his chest, at the very least, looked just as exercised as it did in his nudes. Fortunately, he was nice. He didn’t mention how I was half an hour late, and he hugged me to say hello after confirming that I was the guy he invited over.

We went back up to his apartment, which was a huge one bedroom that had a beautiful view of a bridge. That was the only beautiful thing about his home. The mess made it seem that a tornado wrecked the place. There were boxes everywhere, shoes on the table, sex toys sitting on a shelf in an open closet, messy plates on an unmade bed whose sheets were hanging from an edge for dear life. It prompted me to ask him if he had just moved there, and to my embarrassment, or his for that matter, he said that he had been living there for a year.

He invited me to the shower, but I declined, having just hopped out of the shower before hopping into my Uber. He asked me to wait in the bedroom to make myself comfortable, and I ended up cleaning it while he cleaned himself. Now sitting on a made bed, I basked in the last moments of my virginity. I tried to take everything in, how white his walls were, how nice my new jacket that I got from Woodbury Commons yesterday looked on his hardwood floors, how good his voice was while he sang in the shower, how I was awkwardly sitting on a stranger’s bed waiting to be fucked for the first time…

And then it hit me. I was about to have sex with a man for the first time. For me, it felt like a total acceptance of my sexuality. I was gay, and I liked dick (or wanted it, at least). The sight of a hot, naked man approaching me told me that there was no turning back now.

We started kissing, slowly at first then really fast. Before that moment, I had never had a tongue run across the length of my body, reaching nooks and crannies that made me pause and take a deep breath out of pleasure. John flipped me over, and told me that he was going to finger me first, to loosen me up. With his teeth, he ripped open a sachet of lube and poured its contents all over his finger. He toyed around my hole before pushing his finger in. No amount of mental preparation could have braced me from what I was about to experience.

I didn’t like it. It felt weird, and that was just a finger inside of me. It felt a lot like a plunger was stuck up my ass, pumping to relieve me from a week-old constipation. I was wildly disappointed, but I reminded myself that this was just a finger—maybe a penis would be different… It was, and it was worse. With a penis inside of me, it felt like I was passing poop back and forth in my anal cavity. Except for the initial pain of it sliding in, it didn’t really hurt. I was suddenly sweating out of nervousness. I couldn’t stop thinking about pooping, so I had to pause and say, “John, stop. Am I shitting on your dick?”

I thought that I absolutely ruined it, but he told me that it’s supposed to feel like that and that I should relax for it to feel pleasurable. Ten more minutes of whatever the fuck that was later, I told him that I wanted to go back to making out. We did. We came. We showered.

While in the shower, I asked John to grade my performance in bed. He said that I was too tense, but that he understood why. For one thing, it was my first time, and bottoming just wasn’t for everyone. It wasn’t for him, either, he admitted. He shared the same sentiments as I did, that it felt like pooping but not really. He also told me that if I wanted it hard enough, or if I got used to it, I might like it. I appreciated him telling me that. I appreciated him making me brunch after, too.

So that’s how I lost my virginity, and how I found out that I didn’t like sex. I didn’t feel giddy after; I thought I would be dancing on the streets when I got out of John’s building, but I was just in a hurry to catch my flight. Inside the plane bathroom, I discovered that my neck was covered in hickeys, and instead of seeing them being a trophy for what just happened, it worried me that my aunt in Toronto might find out that I was up to something.

I still had a lot of questions about sex, questions whose answers can only be obtained through experience, so there were plenty of reasons for me to continue seeking and having it.

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