Like most young men in America, I had gone my entire life believing I was meant to be with a woman. I had some satisfying sexual and romantic relationships with them, fell in love with one once, and truly convinced myself this was my path. But, I wasn’t being honest with myself. An unexplored side of me felt drawn to men. And so, right around my 33rd birthday, my body turned off to women completely. I just couldn’t get it up with them anymore.
So I did the right thing. I hunkered down, loaded up Grindr, and began engaging personally and sexually with a variety of gay men.
And, as it turned out, I liked it. Actually, I loved it. I loved being flirty with guys. I loved getting naked with guys. I loved hooking up with guys. And I loved being gay. After years of my sexuality laying dormant, it was like learning a whole new language. Men were the new frontier and I was climbing every tree and journeying through every dark cave to be with them. For the first time in my life, I got to experience being hard all day and night, ( I had missed out on that as a teenager) thinking about the sculpted arms of a man I’d seen at the laundromat or the graceful eyelashes of the barista at my local coffee shop.
One problem, though. There was so much that I didn’t know! You know, like, how to be gay? I had spent so much time in the closet, missing out on what could have been a truly gay twenties, that I was playing catch up, and it was intimidating. I felt I needed to do everything within my power to become as gay as possible. And what could be more gay than hooking up with dudes, right? So, rather than go through these first time experiences in an organic way, I chose to confront my lateness by plowing ahead and going after all the men I could find.
I did a bit of this, did a bit of that, liked it, hated it, and really, really loved it. After a few months, I deemed myself accomplished. Yet, something was lacking. A big thing. A scary thing. I was still holding on to the fear of what would happen when I lost what I coined my Gayginity. True, I’d been hooking up with a lot of guys, and what I did with them would certainly be considered sex, but I hadn’t yet gone all the way – AKA insertion – AKA penetration – AKA you get it.
I was completely insecure about my ability to go through with having that kind of gay sex for the first time. After all, there was never anyone who pulled me aside to say, “Hey, being gay is cool, and if you want to engage in anal sex, there are ways to prepare yourself for it.” So of course my fear of being jackhammered or of being expected to pound a twink on my first go had me reeling.
Was I a top or a bottom? Did I have to choose? Would it hurt? Would I hate it? I felt I had to find out as soon as possible, so I could be ready for a real relationship when the opportunity came. My biggest fear was that I’d meet some dude, fall in love, and get rejected for my lack of experience. Therefore, I quite unromantically forged ahead on a quest to have legit gay sex. Yes, penetrative gay sex. I didn’t know who I’d have it with, or when, or how. But I made the decision in my head to go for it as soon as I found an opening.
And, so, after one particularly late night waiter shift, I messaged a sweet-faced guy on one of the apps and invited him to my apartment. I made sure my place was clean and presentable, gave myself an Italian shower, and downed a shot of rye whiskey. I was ready for him.
As soon as the guy arrived, though, I felt bummed out. He looked exactly nothing like his photo on the app. He was about five inches shorter and 35 pounds heavier. I wouldn’t have cared about him being short or on the heavier side at all, it’s just that I felt deceived. My fantasy had to be adjusted. But I was definitely horny. I looked at him and thought, “Well, he came all this way.”
He waltzed in and immediately started to disrobe. I followed suit. We peeled off our t-shirts, his belly bouncing out in a cute way as he kicked off his sandals. As soon as his small-ish dick popped out, already hard, I knew what to do. I bent down and brought him into my mouth, like a big slurp off an ice cream cone. He moaned. And I worked him. And he writhed. He even arched his back! Before he could cum though, he pulled me up to his face so we could make out.
“Not so fast.” He teased.
“Can we fuck now?” he whispered into my ear in a heavy Filipino accent.
He grinned and gingerly revealed a bottle of poppers. I had actually used them before in prior conquests and learned that poppers make me wild. I’ve definitely done things I wouldn’t do without the rush they can give you, so I figured this would be a good way to provide some additional courage. I snatched them out of his hand, yanked off the top, and sniiiiffffffeeeed away.
“So do you want to fuck me, or can I fuck you?” he asked, quite politely.
“I’ll fuck you, I guess?” I offered. As a former straight guy, I imagined I’d be a natural top. I went to my bedside table to pull out a condom.
“What are you doing?” he complained.
“I’m just grabbing a condom.” I said, confidently.
“Uhmm. Yes. Definitely not going to have sex without a condom tonight. Sorry.” I declared.
“Damn. Okay.” he acquiesced, as he bent over the edge of my bed, ready for me.
The moment of truth. I went and stood behind him. It was so weird. I’d never even had anal with a woman before, let alone a stocky Filipino man, and he was just, well, in position. I slipped the condom over my semi-hard dick and without using a drop of lube, started to shove my member into his ass, but it wouldn’t really go in. Like smashing a Twinkie into a pillow, I kept trying and pushing.
“You have to be very hard if you want to fuck me. I am so tight,” he turned around and said.
I went limp. Something about the way he emphasized “so tight” made me lose my boner. I gave up and stood there, a bit freaked and embarrassed.
“Can I fuck you, then?” he asked.
“I guess…” I uttered hesitantly.
He got up, grabbed my waist from behind, and bent me over, ready to get in there, but I stopped him and said, “Condom.”
“Awww. Come on.” He begged.
“Dude, we don’t even know each other.” I reasoned.
“Alright, okay,” he acknowledged.
He put a condom on and passed me the poppers to sniff as he readied to insert himself into my behind. I was bent over the edge of my bed now, naked and vulnerable. I took a deep breath and sniffed. It was intoxicating.
“Ooh. So hot. You ready?” He teased, slapping my ass.
“Mhmm…” I moaned, bracing myself.
And then…he went for it. I felt his hot flesh piercing me. I was tight and he was breaking me open. At first it felt, I dunno, burny?
“Sniff more. It will help.” He promised.
So, I sniffed. And he kept going. And it hurt. But I was determined. He slowly kept pushing further. And deeper. I felt like I might have to take a shit. But, I had read this was normal, so I stayed the course. He was moving towards the point where I knew I had a choice. I could ask him to stop, or I could let him push past my tight wall and screw me into the next phase of my gayness.
I took another deep popper sniff and let him in. All the way. In. And out. And in. And out. And he started pumping away and moaning and groaning. And I just looked straight ahead.
“Welp, here I am, bent over, with a dick up my ass.” I thought.
And then, a strange thing happened. I left my body and floated up to the ceiling.
“Okay. Well, this is interesting.” I joked to myself.
I looked down and watched him ram it in over and over again.
“He’s loving this, at least. Maybe, this is what hookers feel like?” I wondered.
I watched the scene from this angle as he writhed away until he managed to hit something completely new to me. An uncomfortable pleasure.
“Ungggh!” I yelped, feeling myself rush back into my body.
“You like it?” He paused.
He kept going. And, we both kept moaning. And then…it happened. I came. All over the place. So much cum and all without anyone even grazing my dick. My body shivered as I collapsed onto my stomach and gently pushed him off of me.
“I need to stop.” I told him.
“Oh. Okay. No problem.” He said as he followed me to lay side by side on the bed.
A couple beats of silence passed. I was in my own little world now. That world you enter after you’ve cum and realize that all you want in this moment is to be alone and free of the stranger lying next to you.
“So, now, we are boyfriends?” He interrupted as he wrapped his arms around me.
“Uhhh…I think we’d need to go on a date first?” I suggested.
“Okay, so let’s go eat,” He said, sitting up with a big smile.
“Uh…no, that’s okay. I’m good. And it’s pretty late…” I insinuated.
He stared back at me with bewilderment.
“Maybe you should go?” I managed.
“Oh, yes, it’s already 2:30! Why not come home with me?” He proposed.
“Nah, I’m good here. But thanks, man. This was cool. I’m gonna’, ya know…go to sleep now,” I pressed.
“You’re funny. I’ll call you tomorrow.” He laughed as he slipped on his t-shirt and shorts. He went to the door and looked back to blow me a kiss.
“Okay. Have a good night!” I yelled, turning over.
I waited for the sound of the door to click shut.
“Well, I did it.” I thought, as I sat up, inspecting my body for any changes. I could feel a physical ache from the experience, but overall, I felt released.
“That was pretty chill, actually,” I mused. “I guess I’m a bottom? Maybe, I’ll be able to top if I’m in love with the guy? Will it always hurt? What about poop?” I still had so many unanswered questions.
But, all that really mattered was that I had done it. I had lost my V-card again! I claimed the experience for myself and could now move forward with another little piece of my gayness in position, so-to speak. Now, all I needed was the courage to hold out for guys I was actually attracted to.