Authors: Ryan O’Connell
When Dan arrived, I took his hand and led him to my room. It was in the middle of the afternoon and the sun was still peeking through the curtains. There was no Sade playing in the background or a dark night to hide our bodies. Years later, after having so many wasted hookups at 4:00 a.m. with a playlist blaring from my iPod, I realize now that my first hookup was actually pretty intimate. There were no excuses to make. No alcohol to place the blame on. I was, for the first time, being completely honest with myself about what I wanted.
Dan and I started kissing on the bed. After a few moments, he had to stop and show me how to make out with someone without mistaking their mouth for a jar of Nutella. Once the kissing tutorial was done, I pulled down his underwear and found a dick so huge it would make Ron Jeremy's dick enroll in a self-esteem workshop.
“Your dick is, um, very large, Dan. Are you aware of this?”
Dan looked down at it with casual indifference. “I mean, I guess. It's not that big.”
“Nopeâit's big. I don't know dick very well, but I do know that this one means business.”
He shrugged. “Okay. Sweet.”
I studied it carefully like it was cafeteria mystery meat. I wanted to wrap it around my wrist like a watch or, at the very least, poke at it a little bit. Instead, I did what every normal Bicurious George would do: I went down on it.
Giving your first blow job is terrifying, but giving it to a dick that is only meant for advanced users is a legit nightmare. I didn't know what my gag reflexes were. I didn't even know how to purse my lips to avoid an unfortunate teeth situation. Thankfully, teenage boys aren't the harshest critics when it comes to getting head. Most of the time they just feel so blessed to have a mouth on their penis that they're going to keep quiet. They won't stop you in the middle of it and be like, “You know what? Before you go any further, I have some notes I'd like to give you.”
After going down on Dan for some time, I was starting to get painful lockjaw. He was taking forever to come. I'm sure as soon as he was starting to get somewhere, I would accidentally take a bite out of his penis and send him right back to square one. I finally just threw up my hands in defeat and decided to give him a hand job instead.
Big mistake. Hand jobs are everyone's least favorite thing to do on the sexual activity tree. I don't know a single person who's like, “Oh my God, you know what I just love to do to a guy? I love to spit on my hand and then rub it on their dick awkwardly for about ten minutes. I'm, like, really good at it.” Hand jobs are designed to make us feel bad about ourselves. I've been fired from a lot of them, including the first one I gave Dan. (Well, technically, I quit.) It took me only six jerks to realize that this was not going to be my sexual journey, so I stopped and politely suggested that we jack ourselves off. Dan agreed, and ten seconds later, we both came in unison. It was super cute.
The second I climaxed and exited the sexual fog, I told Dan that he needed to get going. It wasn't because I was ashamed of what I had just done. On the contrary, I was overjoyed. I got my first kiss, my first hand job, and my first blow job out of the way in a single day. Talk about killing three birds with one very sexually frustrated stone. I just had no feelings for him. I had hooked up with someone who was essentially a gateway gay, someone who could carry me over to better prospects. There were no real emotions involved. Plus, there was no way I was going to have my first anal sex experience with a dick that massive.
Instead of focusing on boys, I decided to spend the next few months riding the natural high you get from living your life the way you want for the first time ever. But then something took me by surprise. I fell in love with a boy. When I saw Charlie, a beautiful Latin dude with huge lips, from across my school quad, I thought, “This guy is going to change my life.” I introduced myself to him. He was wearing a Smiths T-shirt that had been cut into a muscle tee, and he looked like something out of a blissful gay fantasy.
“I love your shirt,” I said. “What's your favorite Smiths song?”
“Thanks! âFrankly, Mr. Shankly' for sure.”
“Oh my Godâme too!” I lied. It was really “That Joke Isn't Funny Anymore,” but whatever. I would've told him that I liked Nickelback if it meant that he would be into me.
I knew Charlie was gay. Not because of what he was wearingâalthough a Smiths T-shirt didn't hurtâbut because I felt it. It's an indescribable feeling, one you get when you're young and grow up in a town with people who don't look at things the same way you do. I had come out of the closet to much fanfare, but it really only solved half my problem. I still hadn't found someone to be part of my gay tribe. That's why, when I met Charlie, it was as if I was seeing everything clear and queer for the first time. He was the peanut butter to my jelly, the one who was going to make me feel like less of a weirdo.
After we parted ways, my whole body was vibrating. It felt like I was high out of my mind, and in a way, I was. The most powerful high is the one you get when you're a teenager who's about to fall in love. There's nothing quite like it.
Charlie and I became attached at the platonic dick. We had sleepovers at each other's houses, drove to LA to go to concerts, and had bonfires on the beach. The benefit of Charlie being closeted to his family was that I could share a bed with him without his parents worrying we were hooking up. When summer started, it wasn't uncommon for Charlie and me to spend three days together just walking all over our town, talking for hours. That's the thing that's always baffled me about being young. Your life is so boring and yet you never run out of things to talk about.
Charlie and I had been friends for only a few weeks when he told me he was gay. A few of his friends knew, but to everyone else he was closeted. “I still plan on marrying a woman and having a white picket fence and all that,” he told me in my room. It was in the middle of the day, around the same time Dan and I had hooked up a month earlier. “We'll see if that happens.”
Spoiler: it never happened. As Charlie and I got closer, all our interactions became more and more sexually charged. Finally, one day on AIM, Charlie asked me if I'd like to be his boyfriend. My stomach went into a free fall. Here was someone who was beautiful, warm, and funny, and he wanted me? Unclear.
What followed after that felt like some coming-of-age gay teen movie you'd rent On Demand. Charlie and I spent every moment together, mostly in my bed getting to know each other's bodies. We were like two scientists poking around each other and being like, “Okay, what happens when I do this to you?” I told myself I'd wait until Charlie and I were like
really
in love to have gay sex, which, in teenager time, only took about two weeks.
There was one issue with losing my virginity, though: I didn't know a single thing about anal sex. My private Episcopalian school left that section out during sex ed. So I went to my local Barnes & Noble and bought a book called
Anal Pleasure and Health
and read all the chapters, studied the illustrated pictures, and took notes.
“Charlie, you have to read this book I just bought. It's all about anal!” I squealed.
Charlie looked at the book and made a sour face. “Babe, I think you've been watching too much
Sex and the City
. Can't we just try it and take it from there?”
I couldn't argue with that. Ten minutes later, I found myself flat on my stomach and ready to go. (We tried having my legs up in the air but, um, it didn't really work. Cerebral palsy problems!)
“Okay, tell me when it's going in,” I said.
“Of course.”
A few seconds passed before I screamed out in pain. “Charlie, I told you to tell me when you were going in!”
“Ryan, I literally just grazed you with my dick.”
“Oh. Fuck. Well then, slower, please.”
“Okay, babe.” Charlie started again with trepidation and went in very delicately. “Is that okay?”
“Sure,” I squeaked. The truth was that it felt like a bowling ball just entered my asshole. Having a dick in your ass, even when it feels amazing and your prostate is doing a happy dance, feels strange. There's no way around it. The whole thing just feels so unnatural, which is partially why anal sex feels so hot. When you're letting a dude fuck you, you immediately feel close to him because it's such an intense act. I mean, you're letting someone go inside your butt. Sometimes it feels like they're going so far inside that their dick is going to pop out of your stomach like that little baby in
Alien
! It's that crazy. And if you're like me and don't do anal that often, your asshole is probably tighter than the door at Studio 54. Tight assholes are beneficial for the person who's giving but not for the dude who's receiving.
So here we wereâCharlie was putting his hot dog through my keyhole and I was actually starting to like it. I was still lying on my stomach in pain, but I was beginning to experience these flashes of pleasure I'd never had before. It's hard to even articulate what this kind of pleasure feels like. There's a lot of involuntary moaning. I'll just be getting fucked when all of a sudden my mouth will start to contort and this whimpering, animalistic sound will escape my lips. Afterward, I'm like, “How did that sound come out of my body without any warning? That was cool!”
I was getting the hang of this whole anal sex thing. After thirty minutes of Charlie fucking me, I went from feeling weird and vulnerable to being a full-fledged lesbian who wanted to shout out Ani DiFranco lyrics during sex. With every thrust, I was thinking, “Okay, so we're definitely going to get married, but where? Maybe on a vineyard in Napa or on the beach in Provincetown, although I would hate to make both of our families travel that far. And after the wedding, we're going to hire a surrogate to have our biracial babies. One will be named Donovan, and he'll play the clarinet. Let's pray he's gay like his daddies!”
But just as I was about to scream, “Oh my God, you're the best. Just put a ring on it!” I smelled something weird, something funky, something you should never smell during sex.
“Charlie, do you smell that?” I asked, turning slightly to see him pounding into me, drenched in sweat.
“What?” he panted. “No.”
“Okay . . .” I continued to lie there on my stomach and pretend that what I feared was happening was actually just a figment of my imagination. But then time passed and the stench grew. It was getting to be undeniable. I was smelling the scent of my shit on Charlie's dick.
No one really talks about how common it is for a little shit to come out of your ass during anal sex. This is, after all, why gay men do enemas and colonics. I didn't know this then, though. I thought I was the first person in history to poop on their boyfriend.
“Charlie, stop! I think I'm pooping!”
Charlie, who had a front-row seat to the production of my asshole, already knew what was going on and didn't care.
“I'm almost there,” he told me. “Don't worry. Just hold on!”
“No, please!” I begged. “Let's stop. I'm freaking out!”
“It's not a big deal. Just wait a sec.”
After an agonizing two minutes passed, Charlie finally came and I pushed him off me to run to the bathroom. So much for a tender postcoital embrace. I had shit I needed to clean off my body. People often look in the mirror after they have sex for the first time to see if they look different, and in my case, I actually did. I had an expression of pure panic on my face that I had never seen before and shit smears on my leg. Charlie remained cool throughout the whole thing, which was as much of a blessing as it was disconcerting. The next day, I Googled “anal sex poop” and learned I wasn't a freak with irritable bowel syndrome. People have been pooping on their partners during anal since the dawn of time. Phew. Good to know.
Despite getting off to an, um, shitty start, Charlie and I continued to have sex more or less without incident. It was nice. It was special. It was, at times, almost too intense. And sex would never really feel that way again. This is not a good or a bad thing. It just is.
Right before I left for college in San Francisco, Charlie and I broke up. As sad as I was to be single again, I left my small town thinking I was about to be up to my chest in dick. If I could get laid in sad heterosexual Republican Ventura, imagine the possibilities that awaited me in the swinging liberal city of SF!
It turns out that the only thing that was waiting for me at college was a ten-pound weight gain and a long stretch of celibacy. I lived in San Francisco for two years and didn't so much as kiss a boy. You know how they say that being gay gets better? Well, when you come out and get the complete acceptance of your family and friends, throw yourself a killer party, and fall in love all in less than a year, being gay can only get worse. Much worse.
It gets worse when you sift through gay personal ads and find that most guys are only into “straight-acting men,” which loosely translates to, “I don't want to date a femme queen.” Oh, the misogyny of it all! To the boys who don't want their lovers to act girly, I suggest you just spend your time getting frat boys drunk and fondling them. That's what you really want, right? A big guy named Bob who will ignore you after you give him a blow job?
It gets worse when you're expected to have a vested interest in the lives and careers of Beyoncé and Lady Gaga. Bombshell: I don't really listen to either of those ladies. I'll put some “Drunk in Love” on when I'm blotto and want to turn the mother out, but I'm more interested in listening to music that makes me want to kill myself. It's a personal preference. Just because I was born with dick loving in my genes doesn't mean my body starts to involuntarily move at the sound of a dance beat.
It gets worse if you're fat, ugly, or short. Actually, JK on the short part, because it seems like 75 percent of the gay population is 5´6Ë or below. What's up with that, anyway? Are they making gay people smaller these days? They would.