“Do you wanna talk about what just happened?”
Jake stares at the sidewalk, like he hasn’t heard my question, his toe poking at a dead leaf, illuminated by the streetlight above us. His skinny frame is hunched against the cold, the breeze ruffling his shaggy blonde hair.
“I mean, I feel like maybe we should talk about it,” I try again.
“What’s there to say?” he asks, looking up to meet my gaze. “It was fine, I guess.”
Fine. I’ve been waiting for this moment for five years. And all he has to say about it is, “Fine.”
A gust of cold October wind hits us, a few drops of moisture landing on my face. He shivers a bit, pushing his hands deeper into his pockets.
“We should probably get going,” he says. “Looks like it’s gonna rain.”
An hour earlier, we’re standing in the same spot, the sun easing towards the horizon. We met five years ago through a mutual friend and have hung out semi-regularly since. We’re the same age but he’s a late bloomer sexually, the product of being raised in an intensely religious household.
He’s got other gay friends, but I’m the one he comes to for all things sex-related. I took him to his first bathhouse, advised him on losing his anal virginity, and walked him through his first case of crabs. It’s always been a bit big brother/little brother. But through it all, the crush I’ve been harbouring on him has been growing. And now we’re finally going to have sex for the first time. The only catch is that there will be an audience.
A regular client has asked for a threesome. He’s a curmudgeonly old bastard, but demands little and pays reliably. Our sessions involve chatting for a bit (usually him complaining about immigration) followed by me sucking him off while he huffs poppers.
Today is going to be a little different. The chatting and sucking off will still happen, but in between, Jake and I are going to put on a bit of a show.
When you book a duo with a regular client there’s always a concern the other escort might try to swoop in and steal your john away. Here though, that’s not a concern. Jake is curious to know what sex work is like. But he’s not really interested in breaking into the business, which is part of the reason I’ve asked him.
An hour earlier, we had met up to take the subway. He was quiet, but also seemed a little bit excited. I’ve laid out the particulars on the ride. Our host is a remarkably easy client. After a little small talk, he’ll watch the two of us fool around. When he’s ready, we’ll suck him off together, which will only last a few minutes.
Afterwards, we’ll sit for another chat and then, when the hour strikes, we can leave. For this client, sex is largely incidental; as much as he proclaims his hatred of humanity, his main reason for hiring boys is the company.
On the sidewalk near a cluster of suburban high rises, I spark a joint take a deep inhale before passing it to him.
“Don’t worry,” I say. “It’ll help you relax.”
After passing it back and forth a few times, I take one last puff and drop the roach onto the sidewalk, putting it out with my toe.
“Okay then,” I say. “Ready?”
He nods silently, smiling a little, and we walk towards the building.
“Once we’re inside, just follow my lead.” I say, as we step into the lobby. “If he starts to talk politics, smile and keep your mouth shut. He’s not interested in alternate perspectives.”
The door is ajar when we get to our host’s apartment. I knock gently before stepping inside, closing it behind us. As usual, he’s seated at the dining room table, puffing on a cigarette. There’s a can of Diet Coke in front of him and his bathrobe is barely covering his substantial belly. His dark hair is combed into a sharp part, held in place by a handful of Brylcreem.
I introduce Jake and then start stripping down to my underwear. He looks at me and I give him a quick nod, indicating he should do the same. It’s a typical middle-aged single gay man’s apartment: a China cabinet crammed with plates inherited from his mother and a cluster of ceramic dog figurines on the shelf he gave up dusting a few decades ago.
A large oil painting of a forest hangs above the dusty-blue sectional sofa. Opposite, there’s a brown leather recliner where he likely spends most of his waking hours. In the corner, a large flat-screen TV, probably the only new thing to enter the apartment in a decade, plays a grainy scene of three barely legal boys sucking each other off.
I haven’t told the client that Jake is about to lose his sex work virginity. Maybe he would have been even more interested if he’d known. But it might also have turned him off. He only hires, as he says, “real professionals.” No matter how much sex you’ve had in your private life, you can’t really claim that status until you’ve got three to four hundred clients under your belt.
We each take a seat at the table and our host offers us a drink. I suggest a beer and Jake nods in agreement. Our host walks to the kitchen, returning with two cans of Molson Canadian, and places them on the table in front of us.
He’s in his early 60s and has worked in the service industry for decades, so he’s got that slightly uncomfortable customer service politeness. We open our beers and I chat with our host while Jake stares at the lace tablecloth.
Noting around 20 minutes of the hour have passed, I stand and invite Jake to the living room where our host has pushed the coffee table aside and laid out a baby blue blanket over the faded Persian rug. There’s a small suitcase open on the floor next to the recliner with condoms, lube and a bunch dildos in varying sizes. Our host lights another cigarette and leans back in his chair, his bathrobe falling open.
Jake is a resolute bottom. But he’s told me in advance his ass is really tight so I might not succeed in getting in. The client hasn’t insisted I fuck him, but I know he’ll really get off on it, so I’m hoping we can make it work.
As Jake and I stand in the middle of the living room, staring at each other, the weight of the situation sinks in. I’ve been fantasizing about hooking up with this guy for years. And it’s finally going to happen, a 60-something, chain-smoking retail store manager as our witness.
I put my hand around the small of his back, pull him close to me and stare into his eyes. Deep blue pools, like oceans, like sapphires. Our first kiss is slow, sensual, long. Our lips still pressed together, I pull him down to the floor and lie on top of him, my hands gripping his waist. I can feel his heart beating through his chest. Has he also been thinking about this for the last five years? Did he agree to do this so we could fuck?
Leaving him on his back, I sit up on my knees and start fondling his cock through his underwear. I glance over at our host. His cigarette is burning away in the ashtray and he’s leaning back, one hand in his bikini briefs, the other holding a bottle of poppers under his nose. He gives me a nod and I grab Jake by his waist, turn him over and pull him up to his knees.
Slowly, I pull Jake’s briefs down, red American Apparel style as I’d instructed — our host like boys to be dressed like boys. I bury my face in his ass, my tongue deep inside him, and he lets out a moan. I keep eating his hole, opening him up. When he’s wet with spit, I try to ease my finger in, but he’s so tight it cuts off the circulation. No way my dick is going in there.
I sit up on my knees and give his ass a little slap. He jumps.
“You ready to get that ass fucked, boy?” I say.
He whispers a yes. I start rubbing some lube into his ass with one hand while I riffle through the dildos with the other, trying to find the smallest one. I finally settle on a slim flesh-toned one, about four inches in length. As I play with his ass, I use my free hand to open a condom, slide it over the dildo and then glance back at our host. His briefs are pulled down and his cock is hard.
I try to gently ease the dildo into Jake’s ass. He resists, but after a minute or so he relaxes and it slides in easily. I fuck him with it briefly, but his body stiffens again, so I settle for leaving it inside him and crawl around to kneel in front of him. I take his face in my hands and he looks up at me, his eyes as intense as before. I pull him up briefly to press my lips to his, and then push him back onto his hands, bringing his face into my crotch.
He takes my cock in his mouth without being prompted and I begin gently fucking his mouth.
“That’s a good boy,” I say. “Take that cock.”
I don’t know if he’s just performing or if he actually likes this kind of Dom talk, but he starts sucking more enthusiastically. I look up at our host and nod at him, indicating he should join us. He goes over to the recliner, pushes the suitcase to one side with his foot, and returns to sitting.
“I’m ready for those boy mouths,” he says.
I ease my cock out of Jake’s mouth and push him slightly in the direction of the recliner. I expect him to hesitate, but he starts sucking our host hungrily. Maybe he’s got the sex-worker gene after all. Crawling behind him, I ease the dildo out of his ass, toss it on the floor next to the suitcase, and press my head into our host’s crotch alongside his.
As usual, he comes in less than 30 seconds. As he falls back in the recliner, I stand, taking Jake’s hand to ease him up and guide him to the bathroom. Returning to the living room a few minutes later, our host is back at the table, an envelope next to each of our beers.
I put my underwear on, Jake following my lead, and we return to our seats to finish our beer. As before, I chat with our host (today’s topic being all the money wasted on foreign aid) while Jake stares down into his lap.
As the hour strikes, I go to the living room and pull on my jeans. Jake looks around, slightly confused, but then realizes we’re leaving and starts to dress. Our host gives each of us a peck on the cheek and then we take the elevator back down to the lobby.
Half a block from the building, I stop and grab Jake’s arm.
“So,” I say. “Do you wanna talk about what just happened?”
He stares down, silent.
“I mean, I feel like maybe we should talk about it,” I try again.
“What’s there to say?” he asks, looking up to meet my gaze. “It was fine, I guess.”
We stand, me staring at him, him staring at the sidewalk, until a few drops of water hit our faces.
“We should probably get going,” he says. “Looks like it’s gonna rain.”
I’m lost. I have no idea what to say. Was this just a quick way for him to make $200? Did he not feel what I was feeling?
“Hey,” I say, stepping closer to him and putting my arms around his waist. “What happened back there . . . did you . . . feel anything? I don’t know but, the way you were looking at me, I just felt like there was,” I pause. “I don’t know something happening between us.”
He looks up, smiles and gives a little shrug.
“I get that a lot,” he says. “I just have these eyes that people always think I’m feeling things I’m not.”
I can feel my face getting red with humiliation. What the fuck was I thinking? We’ve been friends for five years and nothing has happened. Shouldn’t that have been clear enough? Whatever he feels for me, whatever this friendship is for him, that’s all it is.
I look up towards the streetlight, the droplets of water coming steadily now, sparkling in the harsh white beam. I can feel a single tear in the corner of my eye.
“Cool,” I say as I release my hands from his waist.
“Cool,” he says nonchalantly, looking up to meet my gaze. For the first time since we met up a few hours earlier, he seems confident. We both knew this would be the first time we had sex together. But now I realize what he’s maybe known since the beginning that it would also be the last.
We walk towards the subway in silence.
Why you can trust Xtra
