The First Time I Cheated With a Man

Robert, a Canadian I met in London, blue eyes, massive cock and so hot we aimed for a 3 day marathon.

  • Score 9.3 (15 votes)
  • 987 Readers
  • 3518 Words
  • 15 Min Read

The year had already worn me down. I was feeling burnt out, bored stiff, and a bit stuck in a South London routine that felt like a grey loop of spreadsheets, squirrel-watching, and low-grade depression dressed as normal life. Calum was off living his glamorous, jet-setting work life while I was mentally dry-humping nostalgia and thinking about Milan like it was salvation.

I did not envy Calum for all his travels and the realisation of his lifelong dream, but I did feel a little bit of resentment that I was stuck exactly where I’d never wanted to be.

Then, out of nowhere, Robert messaged me on a lesser-known fuckapp.

The first thing that struck me was the Canadian flag and a massive, uncut dick. I suspected he might be as sexy as he sounded. That morning, his profile dick pic looked good, and his bio said, "blonde," "toned and muscular," and "visiting."

I was already more than interested. Then he sent me his face pic and that inner saboteur instinctively told me, "he will ghost you."

But he didn’t. We spoke for less than a few minutes and he sounded very keen.

"You’re exactly my type," he told me.

My suspicion demanded a second verifying face pic. I got that pic and he got my address.

"Do you look like your pics? Are they current?" he clarified.

"Yeah. I’ll take a selfie for you now if you like," and without waiting for confirmation, I took a pic and sent it.

Again, that small part of me expected this to be where it ended. It’s not that I don’t land good-looking guys, it’s just not usually this easy.

Another friend in my age range once told me it took him a week to find a good shag, and another week to get him into bed. I called him desperate. He called himself picky. 

Canadian Robert

Married but with “an arrangement,” which for once didn’t set off any alarms or trigger the usual internal sirens, Robert was on holiday in London with his husband but normally lived in Atlanta, USA. Everything about our chats had felt light, easy, flirty, and, miraculously, drama free. There was something in the way he messaged, the tone, the timing, the lack of drama that made me pause and think, maybe, just maybe, this guy wouldn’t be a complete waste of lube.

I stepped into the shower with a grin already forming across my face, not from nerves or uncertainty or even that familiar gut-check of wondering if he might turn out weird, but from genuine excitement. That golden, pre-sex buzz had already started its slow rise from deep in my belly, spreading outwards and crawling behind my zipper, waking up a cock that had been mostly hibernating through a depressing stretch of uninspired weeks. I took my time, trimmed, scrubbed and shaved my balls with the kind of hopeful precision usually reserved for date night or someone I was at least semi-invested in. I even chose a pair of underwear like it would make a difference. Realistically, if this guy showed up and matched the photos, those briefs weren’t going to stay on long enough to matter.

His hotel was about fifty minutes from mine, give or take and like some kind of punctual sex god, he arrived in forty-nine.

I opened the door and, for a brief second, genuinely wondered if I’d accidentally conjured him. Blonde, fit, relaxed, with a big, warm smile that felt like the opening line of a conversation we hadn’t technically started yet. His face, cuter than the pics, which almost never happens, lit up as those piercing blue eyes met mine and just connected. He looked like he was about to say we already knew each other, and in that moment, I would have believed it.

I smiled back, stepped forward, and offered my hand, half-charmed, half-fuck-it curious. “Hey... I’m Luca.”

He took my hand without hesitation, stepped inside as if it were the most natural thing in the world, and gently pushed the door shut behind him with his foot, sealing us into something that already felt charged.

He was a couple of inches taller than me and just stood there, calm, casual, wearing a grin that didn’t ask questions or make assumptions, just... waited. There was an expectation in the air, but it didn’t come with pressure. It came with ease.

I didn’t know what to say, and so, true to form, the first thing out of my mouth made me want to throttle myself.

“Like what you see?”

It wasn’t the first time that week I’d wanted to punch myself in the balls for opening with a line like that.

But he laughed, a kind of real, relaxed laugh that makes you feel like the universe isn’t actively punishing you. His eyes lit up, and with the kind of unfiltered joy that should be bottled and sold to bitter gays everywhere, he grinned. “Oh yeah.”

I grinned too. “Me too.” It felt honest and it felt good. And it felt like this wasn’t going to be one of those soulless, mechanical shags that leave you checking your phone before your jeans are even zipped. Robert exuded something rare, something worth leaning into. So I did. I stepped closer, tilted my head slightly up, and kissed him.

 The First Kiss

The moment our lips touched, something electric surged through me and my cock snapped to attention like it had been waiting for this kiss its whole life. His arms wrapped tightly around me, pulling me in, and without hesitation, I wrapped mine around him too. Those lips were warm, thick, juicy, and melted into mine with a kind of ease that made it feel like we’d done this before. I didn’t think, I didn’t hold back. My tongue slid forward, gentle at first, just to see, and his tongue met mine without hesitation.

That kiss in the hallway shattered the last of any resistance. No fear, no inhibition, no internal monologue asking if this was too soon. All of it vanished the second our cocks pressed together through layers of denim. The tension was unbearable. I needed him upstairs in my bed, naked and hard and inside me as soon as possible. I smiled into the kiss, pulled away just enough to grab his hand, and led him to the stairs.

We barely made it into the bedroom before we were kissing again. Fiercer now. Our dicks pressed and ground against each other, aching through our clothes. I slid my hand down, palmed the bulge in his jeans, and stroked him through the fabric. It was massive. That kind of thick, heavy cock that comes with its own gravity. I kept kissing him, somehow keeping pace while my fingers fumbled with his button, then his zip, then that last bit of denim standing between me and the heat I wanted in my hand.

I got it. I reached in, wrapped my fingers around the thick shaft, and felt it throb in my grip. My brain went quiet. I was in trouble. The good kind. The kind of trouble that keeps you sweaty and smiling for days.

He slid his hand into my briefs and wrapped it around my cock like he’d been planning to since breakfast. I nearly came on the spot.

“Naked nuns,” I whispered in my head. “Year Nine maths teacher. Cold porridge.” Anything to stall the climax that was threatening to turn this into a one minute encounter.

I pulled him toward the bed, stripping us both as we moved. His T-shirt disappeared behind him. Mine hit the floor. Jeans came off. Socks, who cares. In seconds we were naked, hard, and kissing again, like two men possessed by lust and gratitude that neither of us had flaked.

 Round One

I pushed him onto the bed and climbed on top, our cocks sliding against each other, slick with precum and an almost absurd amount of unfiltered desire. He moaned as I leaned in, my lips finding his neck, licking slowly, tasting the heat rising from his skin, while he tilted his head and sucked gently on my earlobe like he already knew it would make me melt. It felt incredible, filthy in the best way, and so goddamn real that for a second I forgot we had only just met.

But my mouth wanted his again, and clearly the feeling was mutual, because before I could even pull back, we were kissing with the kind of intensity that blurs everything else. That kind of kiss that makes you question whether this is just a hookup, or the beginning of something that might destroy you in all the right ways. Our tongues found each other again, and the way he moved, the way he kissed, it was like his whole body was asking mine to give in.

The buildup started to hit me. That swelling pressure in my gut, the one I recognised too well and tried desperately to ignore. I clenched, adjusted, shifted my weight, kissed him harder, but the friction, the kissing, the sound of him moaning into my mouth... it tipped me over the edge. My cock throbbed and I came, shooting a hot load between our bellies, gasping as I pulled my face back just far enough to breathe.

“Shit,” I muttered, almost annoyed at myself.

Robert looked down at the mess and frowned. “Oh no…”

I knew that look, so before the vibe could dip even a little, I played the card I always kept in my back pocket. “Oh, I cum multiple times.”

His eyes lifted with genuine surprise, and then, delight. “Oh…”

We both laughed, and just like that, the spell wasn’t broken. It was deepening. I kissed him again, harder this time, with all the renewed enthusiasm of a man who knew he was just getting started.

 Multiple Rounds

I licked his chest, then moved slowly to his nipples, spending far longer there than I probably should have. I sucked on them, circled my tongue, and let him squirm beneath me while I kissed my way down his stomach. A trail of saliva, sweat, and leftover cum followed behind my mouth as I travelled south, tasting remnants of myself as I reached his cock. That thick foreskin peeled back like a surprise waiting to be unwrapped, and I took a second just to savour the sight of it.

Gently, I ran my hand along the length of it, enjoying the heat radiating off his skin. He was pale, spotless, freshly showered, and he smelled clean in that way that made you want to bury your face in him. The moment my lips touched the head of his cock, I paused to taste it. Warm. Smooth. Fresh. Then, without warning, I swallowed it whole. He gasped and grabbed the sheets with both hands.

His balls were perfect. Shaved, tight, and heavy. They smelled good enough to make me moan, and I sucked one, then the other, then both, before licking back up his shaft slowly. I did it again. And again. Teasing him. Edging him. His cock pulsed with every pass, and I could feel how close he was getting. One more stroke and he probably would have lost it.

Before that happened, his hands grabbed me and pulled me up toward him. He kissed me hard, and I pressed my body onto his, letting the weight of me settle between his legs. He responded immediately, wrapping those legs around my waist like he wanted to keep me there forever.

Then he flipped me over. Suddenly he was on top, grinding his cock against mine, lips tracing hot lines down my chest, my belly, and then down to my hips. His mouth found my cock and swallowed it in one smooth, perfect movement.

I came again.

He looked up at me, mouth still full, eyebrows raised. "Already?"

"Second round," I said, breathless.

He swallowed, grinned, and went right back to it. My cock didn’t even think about softening. I could go for six. That was my record.

Robert sucked me until he couldn’t take it anymore, then climbed back on top and kissed me, reaching for the lube like a man on a mission. He lubed himself quickly, like he’d done it in this exact drawer in this exact bed a hundred times before.

He looked into my eyes. "Okay?"

I nodded. My legs spread instinctively. His cock pressed against my hole. I tensed.

"Slow," I whispered. "It’s been years."

He kissed me again, pushed gently, and slid in. And fuck me, it was unreal.

Thick. Hard. The perfect angle. He took his time, watching my face, pausing when I gasped, moving only when I relaxed. My legs wrapped around his waist and I pulled him in deeper, adjusting until the stretch gave way to that sweet pressure I hadn’t felt in too long.

Each thrust came with a kiss. Each moan came with intent. He wasn’t fucking to impress me. He was fucking me to erase everything that had come before him. All the loneliness. All the dead sex. All the silence.

And it was working.

He held himself up with one arm and cupped the back of my head with the other, locking our mouths together as he moved inside me. Deep. Rhythmic. Controlled. Our tongues stayed connected even when our eyes couldn’t. When they did meet, that kiss got stronger.

"Want me to jizz?" he asked, panting.

I shook my head. "While I’m fucking you."

He smiled, pulled out, and let me climb on top.

We started grinding again. Our cocks pressed together, and I leaned in for another kiss. His eyes were locked on mine, hungry, present. It was almost too much. I reached for the lube while still kissing him, lubed up quickly, tossed the bottle aside, and guided myself in.

As the tip of my cock pressed against his entrance, we both moaned into each other’s mouths. I pushed in slowly. He gasped. Another kiss. Another inch. His legs wrapped around me and pulled me in deeper.

"Holy shit," he whispered.

I fucked him slowly, deeply, letting every inch find its place inside him. I kissed him, licked his neck, his ears, his mouth again. Then I sped up. My cock moved in and out of him while his legs locked tighter around me.

It was building again.

"Are you cumming?" he asked, reaching down to stroke himself.

I stopped him with a shake of my head. "One more time," I said as I thrust deeper. His face twisted in surprise, even as I came inside him. I felt the load fill him.

"Shit," he said. "I felt that."

I grinned but didn’t stop. I kissed him again.

I knew I had one more left. Still partially cumming, still hard, still hungry. My cock was staying put.

"You want to cum?" I asked.

He nodded. But instead of giving him his hand back, I pressed my belly against his cock and kissed him harder while I looked into his eyes and kept thrusting.

He moaned, louder now. This was the moment I used my second superpower.

I adjusted slightly, making sure every thrust dragged my belly perfectly across his cock and balls. I could feel it in him. The tension, the need and the desperation.

His face gave it away. Pleasure. Surprise. Eagerness. All at once.

I kissed him deeper and fucked him harder. My cock slid all the way in, again and again. I could feel the pressure mounting in both of us.

"Oh fuck," he shouted.

And that was it.

He came hands-free, thick ribbons shooting up across his chest, his abs, his neck, while his eyes stayed locked on mine. I came too, one last time, emptying myself inside him while watching him unravel.

We stayed like that for a quite a while. Sweaty. Spent. Grinning.

And it still wasn’t enough.

 Afterglow

By the time we collapsed next to each other, soaked in sweat and cum and spit and lube and whatever the fuck else, we were grinning.

"I needed that," I said.

He nodded. "Me too."

He kissed me again, slower this time. Not goodbye. Not yet.

Then he asked, "You made me cum hands-free!"

I smiled. "Yeah. Angles."

"So, you’re married too?" he asked.

I nodded, snuggling up to him as we both looked up and enjoyed that post-sex intimacy.

"Yeah. Open, same as you. My husband’s a bit younger. Blonde, blue-eyed and toned and muscular too."

He laughed. "My husband’s your age, muscular, slightly stocky, hairy... I have a type."

"It seems we both do," I said.

We lay for a while and I started thinking about work. It was a working day after all.

"So... I don’t suppose we can get a second round in again?" he asked me.

I turned to my side and kissed him. He was open to it and pulled me on top. His intense eyes just penetrated me like his dick had. We kissed for a bit longer.

"When do you leave? Are you around tomorrow?" I asked him, returning to another kiss.

That dopamine hit was huge. I wanted more.

"I’m here two more days and yeah. I can do tomorrow." I loved to hear that Canadian accent.

We spoke for a bit longer, but eventually got him dressed and out, kissing occasionally on the way to the door.

The next day he messaged me mid-morning. I told him to come over, and within the hour he was at my door again. Same smile and warmth along with that soft Canadian charm that made my stomach flip.

The second round was even better than the first. Our bodies moved like they had known each other forever. There was no fumbling or hesitation, just pure rhythm. That kind of sex where you forget who you are for a while and just become touch and breath and hunger.

We didn’t speak much during it. We didn’t need to. His hands knew where to go. My mouth knew what he wanted. Every touch was confident, like our bodies had memorised each other in a past life. He kissed me slowly at first, then with increasing urgency, rolling us back and forth across the sheets as our cocks pressed together and slid against each other with each grind.

I sucked him for what felt like hours, taking my time, watching his eyes flicker every time I changed rhythm. He moaned my name more than once. I rode him slowly, bouncing in sync with his hands gripping my thighs. At one point, I came while kissing him, his cock still deep inside me.

As soon as I shot my load, he forcefully flipped me over and got on top, then gave me this big cheeky grin as he sat on my dick. When he leaned forward to kiss me, he also moved his hand back to put my dick in his arse.

As soon as I felt the head slip in, he gasped and looked up. A few seconds in, he slowly let me in more, each time leaning in with his tongue deep in my mouth.

That second hands-free orgasm made him grin like he’d unlocked a cheat code. That same shocked look on his face, like he couldn’t quite believe it happened twice. We laughed into each other’s mouths, still moving, still hard, still hungry for more and kissing like we’d been lovers for years.

We switched positions like it had all been choreographed in some shared dream. I came more than once. While he didn’t jizz again, he seemed just as enthusiastic about continuing.

And by the time we were done, we were holding each other like we were supposed to fall asleep right there.

We didn’t. He had plans, and I had deadlines.

"Same time tomorrow?" I asked, already knowing the answer I wanted.

"Yeah. I’d like that. Third time’s the charm," he said, kissing me again before leaving.

I floated through the rest of that day with that stupid post-sex buzz that makes you check your phone every ten minutes just to make sure they haven’t vanished. I thought about him more than a few times that day, with a flutter in my chest that I wasn’t ready to name.

The next morning, I got a message from him.

“Hey, some friends from Atlanta are in London unexpectedly. Going to hang with them today. I’m really sorry. If you ever end up in Atlanta, look me up.”

That was it. No kiss emoji. No false hope. Just a gentle end to a perfect two-day dream.

I stared at the message for a bit, not sad exactly, just... disappointed and annoyed that life and timing have such a knack for ruining a good thing.

Still, I smiled. Because it had been worth it. Every second of it.


Want the full explosive story? That two-day dream turned into a months-long nightmare that nearly ruined my life. Read what really happened and what he did next over on Patreon (The Robert Encounter).

Report
What did you think of this story?
Share Story

In This Story