I Had Sex With a Stranger on a Train

It completely changed the way I look at casual sex

It ended with amazing sex, but started when I stepped foot on the train.

I boarded with half a dozen of my closest friends. We had concert tickets, a hotel room booked, and plenty of time to wander through Montreal.

A lot happened on that weekend. But what I remember most is one guy. Well, two guys really.

I met them in the train’s bar car.

I wasn’t quite old enough to order drinks for myself, but old enough to meet someone who would buy some for me.

That’s where I met Adam.

He had a strong, stocky build. Looking at his body made me guess that he used to be on his high school wrestling team.

More than his body, I noticed his attitude. He was cocky and slightly aggressive — a weird mix that felt alluring and annoying at the same time.

He was the kind of guy who would give you confused feelings. He rubbed me the wrong way but didn’t repulse me. He was sleazy, but in a way that was kind of hot — the kind of trashy guy you knew you might end up fucking anyway.

And who knows. Maybe I would’ve ended up under him, feeling the weight of his hefty body while he thrust into me.

But I’ll never know how a night with Adam would go because he also introduced me to Jason.

They were clearly close friends, but I could tell right away that Jason was nothing like Adam.

He dressed in a way that made his body seem fit and lean. He 8had deep brown hair and a well-groomed beard, which is something that just works for me.

What really struck me, though, is how charming he was. I had hooked up with attractive guys. I had fucked a sweet guy or two. Cocky guys had made their way into my pants. But I almost never got the opportunity to meet someone who was actually interesting — and seemed genuinely interested in me as a person.

He was kind and respectful. Talking to him felt easy and natural, even for a painfully shy girl like myself. I was drawn to him and I wanted to spend the entire train ride by his side.

I forgot about everything else. I didn’t care about scoring drinks. I lost track of where my friends were. And even though Adam was trying to hit on me, I kept bringing my attention back to Jason.

When Adam got the picture that I wasn’t going to fuck him, he gave up and I got exactly what I wanted — this hot stranger all to myself.

We talked for hours, but I can’t remember any of that conversation. All I remember is the way it made me feel. The more we spoke, the more I was turned on. As the hours went on, our connection felt deeper and deeper.

I had to fight the urge to squirm in my seat. I wished I was bold enough to make a move — all I wanted to do was climb on top of him, grind against his crotch, and fuse my lips with his.

I wanted him to grab me, shut me up, and have his way with me.

I couldn’t stop the filthy daydreams — of him going down on me, of his fingers playing with my pussy, or discovering what kind of cock was hiding behind the zipper of his pants.

My brain was full of dirty thoughts but my reality was tame. We shifted our bodies as we spoke, slowly moving closer to each other. I felt my heart beat harder when our knees touched.

I tried to keep up with his flirty banter, but all I could manage was to be awkward and coy. Even when he told me I was cute, all I could do was blush and thank him.

The more he showed his attraction to me, the more self-conscious I got — and I barely had any game to begin with.

I already hated that about myself. But I never hated it more than when the train came to a stop and I still hadn’t taken advantage of the situation I was in.

The chance meeting with the hot, irresistible stranger — it was a scenario straight out of an erotic story.

The only thing missing was the erotic ending.

No hot fucking in a sleeper car. No getting fingered in a cramped washroom that wasn’t built for two. Not even a discreet handjob so I could hear him moan, watch him come, and feel proud for being such a naughty girl.

Nope.

Just a long, tight hug before parting ways at the station.

I didn’t want that hug to end. It wasn’t nearly enough — not after I had spent hours falling for this guy. I hadn’t felt that much sexual desire for someone in a long time and I fucking blew it.

“See you around,” I said before walking away.

I hated how cheap those words were. They weren’t right — not for the kind of feelings I had. They came out of my mouth because I didn’t know what else to say.

But I was about to find out that they weren’t just a reflex. They were foreshadowing.

Who Knew Fate Could Be So Hot

I wandered through Montreal, trying to get Jason out of my mind. There was no point in obsessing over a guy I’d never see again.

But the bright city lights weren’t enough to keep me from replaying our conversation and all the opportunities I missed. Every moment I could have escalated things, all the things I should’ve said, everything the girl I wish I could be would’ve done in my place.

I did everything a girl could do to forget a guy.

I almost lost my voice at a heavy metal show. I got a tattoo to symbolize my most recent breakup. I fucked a friend with benefits on a big, soft hotel bed.

I told myself that it hadn’t been all that bad. It was a decent weekend if I focused on all the positives. I had a new tattoo, enjoyed some easy sex, and spent hours with a guy who knew how to make me feel special and attractive.

It could’ve been a whole lot worse.

And then it got a whole lot better.

The ride home was supposed to be boring. I was exhausted from too many late nights in a row. I’d spend the next one reclining in my seat and getting whatever sleep I could manage.

Then I heard a voice that made my heart skip a beat.

It was Adam’s.

I almost jumped out of my seat. I turned around quickly and laid eyes on Jason.

I didn’t believe in fate, but this moment shook my conviction. It felt improbable and a little too perfect. Maybe I was in an erotic novel after all.

I tried to be chill even though I felt like I might melt into my seat. I could feel every single organ in my body tingling.

“I told you I’d see you around,” I said. Maybe I had game after all.

“I never doubted you,” he replied and I was charmed all over again.

He invited me to sit with them and we picked up our conversation. Except this time, Adam wasn’t going to give us space and they spent the next few hours trying to seduce me.

Like any good hot sleaze, Adam’s approach was overt. He teased me with condescending remarks. Sometimes it shaded into negging. For the most part, he just made endless horny comments about my ass, my tits, speculating about how I taste — and a lot of joking-not-joking about turning our pleasant threeway conversation into a proper threesome.

Jason was much more subtle and way more effective. He had a personality built for chemistry. He didn’t have to say a word about fucking — just being with him gave me the urge to do anything and everything with him.

I’m sure Adam got laid plenty — his hot horny bastard schtick wasn’t the worst thing in the world. But feeling drawn to someone is so much hotter than having them push themselves on you, so it’s Jason I was touching knees with again.

Adam couldn’t wear me down, but trying so hard wore him out. He got so tired of all the talking and no action that he fell asleep soon after the sun had set.

With Adam out of the way and several hours before reaching my destination, I hoped desperately that I would have the nerve to put the moves on Jason. Or better yet, that he’d put them on me.

I was smitten, horny, and ready to be taken. I would be his for the night — all he had to do was touch me and we’d take it from there.

I have no idea what we were talking about. I just know it was flirty. And once the few other passengers in our train car had nodded off, he started tracing his fingers on my thigh.

That killed the conversation. His touch made me so nervous that I could barely speak.

But I didn’t have to say a word. He leaned in and touched his lips to mine. Softly at first — slow, lingering kisses that felt long overdue.

We couldn’t hold back. The soft kisses turned into a passionate makeout session. I wanted my lips on his and I didn’t care how sloppy it got.

I climbed on his lap and felt his stiffness get even harder. I felt shivers at the thought of finally getting to play with that cock, to give it pleasure, to have it inside me.

I have no idea how long I spent grinding against him. I lost all sense of time. I just fell into the experience — the pleasure of rubbing my pussy against him, how soft his beard felt, the way he reached up my shirt to run his hands on my plump curves, his hands grabbing my ass in a way that made me feel wanted.

I could have spent the entire night on his lap. I only climbed off because I knew I’d regret not experiencing more of him.

He threw a blanket over our laps, undid my pants, and slid his hand in my panties. His fingers rubbing my already wet lips was incredible. His eagerness to pleasure me turned me on almost as much as the fact that he was touching me.

I couldn’t resist touching him back.

I reached under the blanket and impatiently fumbled with his button and zipper.

I tugged his underwear down, grabbed his cock, and stopped moving for a moment.

I had been so eager to find out what he was packing, but I was completely shocked when I found out. I would have never guessed that he was so thick.

I honestly didn’t know girth like that existed. His cock was short, but it was massive.

It felt familiar in my hand, like I had muscle memory for it. Not because I’d handled a guy that size before, but because it felt exactly like holding a soda can.

Except I didn’t know what to do with this human soda can. My usual handjob technique wouldn’t work. I experimented a little, played with it, tried to figure out different ways to pleasure him. I loved the challenge, but seeing on his face that I had done something right was even better.

His fingers working my clit could’ve easily made me come. I’m sure my hand would’ve eventually brought him there too.

And as hot as it would be to have a guy with very capable hands finger me all the way to a climax, I wanted nothing more than to feel him inside me.

He rummaged for a condom while I looked around to make sure no one was awake.

I pulled my pants and underwear down to the bottom of my thighs, kneeled on the seat, and bit my lip while waiting to find out if I would be able to take his cock.

He positioned himself behind me, pressed the head of his sheathed cock against my pussy, and steadied himself by gripping my hip. I was as wet as I’d ever been, but he was still slow and deliberate — the way a guy wielding a massive cock should be.

I gasped when he slid inside me — not just because I was finally getting fucked by the hot stranger, but because my pussy had never been stretched like that before.

I tried to stay quiet but I couldn’t hold back my moans. I tried to muffle them on the back of the seat, but it was too late. I could see Adam’s eyes looking back at me.

When I look back at that moment, it’s one of the things that makes the memory so hot.

Anything could’ve happened. My amazing fuck could’ve turned into a threesome. These guys could’ve taken turns pleasuring me. Adam could’ve stood up and slipped his cock in my mouth while his friend pounded me from behind.

He could have just pulled his cock out so I could watch him beat off to the action happening in front of it.

And there’s just the fact that I was being watched. I was getting fucked from behind and losing my mind with pleasure. I love knowing that the look on my face wasn’t wasted — that someone got to witness it.

Those are all hot fantasies, but none of them happened. And I didn’t want them to. In that moment, I wasn’t really thinking about Adam. I registered him looking at me, but that was it. I didn’t care at all.

That was almost as shocking as the girth of the cock inside me. I’m normally incredibly self-conscious and easily embarrassed. But turns out that if the dick is real good, I don’t give a fuck who’s watching me.

All I wanted was for it to keep going.

I wanted to keep feeling every single one of those mindblowingly pleasurable thrusts.

I wanted him to last as long as he could — maybe even long enough to make me come.

I wanted to feel everything about him coming. I wanted to feel his cock twitching in my pussy while his come filled the condom. I wanted to feel his muscles tense and his grip tightening around my hip. I wanted to hear him struggle to stay quiet. I wanted that satisfying feeling of him slowly pulling his slightly softened cock out of my pussy.

But I didn’t get any of that. My train fuck didn’t have a proper finish.

Just a cockblocking train attendant showing up before either of us could come — or even try out a few other positions.

I wasn’t too disappointed, though. Even without an orgasm, I felt incredibly satisfied. It was cut short, but it was still an amazing fuck. It was one of the hottest experiences of my life and I would replay it in my mind for years to come.

We composed ourselves and I cuddled him the rest of the way. My great conversationalist didn’t say much. He didn’t have to — feeling his body so close to mine was more than enough.

I stepped off the train seriously underslept but not tired in the least. Nothing will wake you up and make you feel alive like the cold morning air and incredible sex with a guy you barely know.

A Good Fuck Can Change Your Life

That night might not sound like much — lots of buildup, some quick sex, no climax, and a threesome that never was.

But to me, it was perfect.

I didn’t want it to be any more than that. I didn’t want to get Jason’s number and track him down. I didn’t really want to get to know him any more than I already had.

He was perfect the way he was. A guy who literally charmed the pants off of me. A guy who means a lot to me even though he was only part of my life for a weekend. A guy who’s still mysterious enough that I can believe he really is the fantasy I’ve built around him.

He turned a boring train ride into an unforgettable experience.

He was one of the few hookups I’ve had that’s actually worth talking about.

And he completely changed the way I looked at casual sex.

Until running into Jason, my one night stands had been okay at best.

I fucked guys because it felt better than not fucking them. I fucked them because I was hoping it could turn into something more. I fucked them because they wanted to and I’m a nice girl like that.

Getting fucked by Jason was the first time I really learned that casual sex doesn’t have to be cheap.

You can have a real connection even if it’s just for one night. You can get fucked with genuine passion, even if you’re never going to see each other again.

It doesn’t have to just be another number in your body count. A guy can actually make you feel desirable, make you feel cute, make you feel interesting, and make you feel appreciated — even if he has zero intention of making you his girlfriend.

A guy can make you want to fuck him so badly you lose your senses — and you don’t regret a single second of it.

You can have one-night stands, friends you mostly fuck, hookups with strangers on trains — and it can be absolutely beautiful.

The only sad thing about my story is that I never got to feel that way again.

I met my future husband soon after, quickly settled down, and built a small cozy life with him. Except for a few threesomes, a foursome, and a couple of long-distance flings, I basically gave up on casual sex. I definitely stopped looking for strangers to fuck.

I’m not sure it would be worth pursuing anyway. My heart breaks too easily. I’ve become really fussy about sex and I don’t have the patience to put up with bad fucking. I’ve read way too many bad hookup stories for me to bother with any of that.

I dabbled in it for a while, but I don’t really think I’m a casual sex person.

But at least I can still daydream about it. Thanks to one charming guy with a nice beard, I know that the reality can be just as hot as the fantasy.

And who knows, maybe another attractive stranger will seduce me into some incredible train sex someday. Fate helped me out before — I don’t see why it can’t happen again.

If you liked this article, you should totally check out the Rail Me on the Rails (Train Sex, the Thickest Dick, and Pulling Out Triumphantly) episode of my dirty and intimate sex podcast, Pillow Talk With Emma Austin!

Let’s keep in touch! Sign up for my weekly newsletter for updates about new articles, podcast episodes, and spicy content! (I won’t send you anything without your enthusiastic consent!)

❤ If you liked this post, you might also love: