7 min

Anal entrée

A first-timer's account

I went ahead and unzipped his pants, writes Heinel Wong (above) of his initiation into anal sex. There was a python in there, drooling. I pointed it out to him. "That means I'm very attracted to you. My body is responding to you," he said. Credit: Joshua McVeity

He positions for another thrust as I think to myself: I don’t love him, I don’t know him, and he’s being too rough to a virgin.

He has already repositioned twice, but it just couldn’t get in. I’ve read about people who help first-timers by walking them through the process and preparing them for the fuck. I get none of that. Either I look too calm or I’m unlucky. Probably both.

I met him through that magic window others call the internet. I had always thought dating sites were not for me. The whole profile thing is basically a marketing offer, and people pick mates by checking off their grocery list of characteristics. I didn’t think typing a tagline beside my picture would be the way to meet the man of my dreams. I mean, what would I write about? But I had no other options — I didn’t want to go to clubs. Vancouver can be cold sometimes, and in any case I wasn’t going to find a man if I continued to hang out with my small circle of straight friends. Internet dating is mechanical, but it wouldn’t hurt to try, right?

I filled in all the blanks in the profile — it even asked for my shoe size. I also included some of my poems. No one would ever read those, but at least I tried to distinguish myself. I got some messages from people who found me cute, but nothing much came out of those. I wasn’t hopeful. Then he messaged.

“Do you have a phone number I can call you at?”

I introduced myself.

“Can you give me your phone number?”

I gave him the number. People might think it unwise to give out personal information to a stranger, but hey, I’m not a 14-year-old girl. He suggested we meet right away. I said yes to that, too. He was assertive, a go-getter. I was intrigued.

It was 10pm. Cambie St was deserted in typical Vancouver fashion. I had always thought the bright lights of a city should be accompanied by a bustling street full of people, no matter what time of day it was. That’s what it’s like where I came from — Hong Kong — but as I walked out of the SkyTrain station I was completely alone, aside from a couple of cars on the road.

His voice cut through the silence as he emerged from the shadows. His attire reflected his nondescript online profile: black sweater, black pants and a black cap. Maybe he was prepared to run away in case I didn’t look anything like my profile picture. I passed the first test.

He said there was a Starbucks nearby and suggested we go. I agreed without putting too much thought into it.

He got himself a cup of coffee right away. Was I wrong to assume that he would buy me a drink? I got myself a cup of hot chocolate, extra cream. It was a fireworks night and he suggested we watch the sky light up from his place. I agreed, knowing I was being reckless, but I had been too careful, and careful was lonely.

His apartment was so well kept it looked like a demonstration unit. There was not an item out of place. Spotless carpet, stainless kitchen, nothing on the coffee table, only cushions on the sofa, neatly placed. It was something even my clean-freak dad would put his seal of approval on. I could already imagine myself living in this place, typing away in the sun room. It took me a few seconds to appear blasé. He didn’t need to know my opinion.

He turned on the TV and asked me what channels I watched. I said I’m not a TV person but Discovery Channel. He switched to Discovery but quickly surfed away. Why did he ask if he was not going to let me watch what I wanted? He liked sitcoms and soap operas, he said, and started telling me about the hostesses in talk shows. He told me his favourite was what’s-her-name-again, and I just nodded. He kept talking. Okay, I was bored. I forgot about the fireworks until he said it was time to move to the balcony to watch them.

It was a bit chilly outside. He asked if I was cold.

“Not really. My sweater may not look like much, but it’s cotton, it’s warm,” I said.

“You’re not cold?” he asked.

Maybe he didn’t get what I said. There was silence.

He wrapped his arms around me anyway.

Well, it’s about time.

I had expected him to act sooner, and without stupid excuses like “It’s cold.” I continued to stare impatiently in the direction of the fireworks that had yet to start. He saw no reaction and slipped his hand under my shirt. He laid his palm right on my heart. Was he checking my heartbeat? My heart rate was normal. He wasn’t unattractive, but neither was he attractive. That’s not to say I wouldn’t fool around with him, but I wanted him to want me. We watched the fireworks quietly that night. As I pulled on my shoes, he said we should meet again. I said okay.

I was not through with him yet.

“Where are you?”

That’s the question he liked to ask every time he called. It had taken me long enough to get used to the English “How are you?” greeting, and now he gave me this. At least “Where are you” is easier to answer, but I couldn’t help but feel interrogated, like he was trying to take charge of me.

“I want you to be my only one,” he said. “You must not let any other guy touch you.”

I wasn’t sure what to make of that. He hadn’t struck me as material for a long-term relationship. He asked about my history, but not my future.

To his credit, he always gave me something to look forward to. He promised a massage for our second date. Of course, that was an excuse to get my clothes off, and getting naked in front of him still gave me pause. He accommodated by giving me a tiny swimsuit to change into.

I lay on his couch and let him explore my body. Then I thought to check out his crotch. His loose-fitting black fleece masked all the shadows of the contours on his body, and it was impossible to see what was underneath. I knew he was no supermodel, but I still wanted to see. He saw where I was looking and told me to take a peek.

“Really? I can?” I asked, actually talking to myself, but he answered anyway.

“You can do whatever you want.”

I unzipped his pants. There was a python in there, drooling. I pointed it out to him.

“That means I’m very attracted to you. My body is responding to you,” he said.

I liked that answer very much.

“It’s big,” I said.

“You like it big?” he asked.

“Eh, wouldn’t it — hurt a lot?” I looked at him.

“Yeah, it would hurt.” He made no attempt to hide that fact. “My first boyfriend cried when I fucked him for the first time.”

Crying in sex, I thought to myself. That must not happen to me. I didn’t know if he said that only so I wouldn’t back off. Regardless, challenge accepted.

He led the way into the bed-room. It was dark. He shed the black clothes that kept his naked body hidden from view and told me to suck his dick. It was long, hard and straight.

I had imagined what fellatio would be like for a long time. I’d read about it: tongue, lips, work on the tip. But as soon as I wrapped my lips around it I knew it wasn’t going to work. My mouth could barely fit around his dick and it completely stuffed my throat. The only thing I could do was to keep my jaw in the screaming position so as not to bite him. I froze there.

He pulled out and asked me how I was feeling.

“I couldn’t do it,” I said, feeling a little disappointed in myself.

He sighed lightly but quickly pushed me onto his bed. I didn’t know what to do, so I just lay there without moving and let him touch me. I remembered reading on the internet about “dead fish” and how unsexy it felt to be with one. Maybe I should do something. I grabbed his ass. He didn’t seem to notice. Okay, what now?

He seemed to be preoccupied with kissing my neck and grinding his hard cock on my thigh. I wondered if he was enjoying it. I didn’t think it was all that interesting — just a guy wriggling on top of me. Sure, I was rock hard, but I was rock hard when I played by myself, too. I didn’t see what was so amazing and different with this. He changed his position and rubbed his dick on my butt cheeks.

“I want to fuck you,” he said.

So this is what it feels like, I thought to myself. It wasn’t as much of a tease as pornographers made it seem. I wondered if it was because I couldn’t see it? I closed my eyes and started to imagine his penis: long, thick, smooth, white shaft with a pink head — round with a perky tip and oozing — a fine specimen, inviting and flawless from any angle. I remembered how I used to fantasize about playing with a dick just like this. I’d make it squirt over and over, I told myself.


“I want to fuck you,” he repeats. His movements turn brisk. He is breathing hard.

And what am I doing? Waiting for something to happen? Why can’t I just take this opportunity and enjoy myself? Something is stopping me. I’m too self-conscious. I can’t even trust myself let alone anyone else. It’s just the way I have always behaved — it’s like second nature. Somehow I manage to push people so far away I no longer know what it is like to be with other people, to interact. Maybe this man can help me. He is experienced. He can penetrate my defences. He will.

He stops moving and presses his body tight against mine.

“Can I fuck you?” he whispers.

“Yes,” my response is loud and clear.

Yes, I’m in someone else’s bed at this moment. This someone is right on top of me and is going to be the first person to fuck me. From now on he will be a part of me in my memory, no matter where my life brings me.

I suddenly realize that my muscles are all tensed up. I’ve been clenching down so hard he can’t find entrance. I have held this tension in my body for so long — far too long. I want to change.

I feel him squeeze my ankle as he gets ready for a final thrust. I let go of myself, feeling the force of his drive. He gets in — deep. It hurts.