My best one-night stand isn’t one that sounds really impressive.
The sex wasn’t athletic. We didn’t try fourteen different sex positions. Neither of us even came.
But it’s still my favorite short-term fuck and one I know I’ll never forget.
Everything just kind of fell into place perfectly. It felt like fate and a few other bullshit concepts I don’t fully buy into.
I was feeling emotionally vulnerable but also bold. I needed someone who could make me feel like I was worth a damn — and I found him in a train car.
The Meet Cute
I was on a train with six of my friends. Two couples, two unattached guys, and then me.
One of the unattached guys, John, was an off-and-on friends with benefits. I really liked him and he liked fucking me, but we’d kept our hands off each other for a while.
We were on our way to Montreal for a Megadeth concert. A bunch of young, excited metalheads who still lived with their parents finally getting a real taste of freedom for a weekend.
Soon after boarding and settling into our seats, a guy who looked to be in his early twenties approached us. He asked if we’d like to hang out at the bar with him and his friends. Hanging out at a bar was an exciting prospect for a bunch of kids who were just on the verge of the legal drinking age, so we eagerly accepted his invitation.
At the bar, we met a few guys, but one of them moved in on me immediately. I don’t remember his name — that’s fine, he’s not the guy I’ll end up fucking — so I’ll call him Adam.
Adam was stocky and strong, built like a wrestler. He had a cocky, aggressive attitude that matched his muscular frame. It immediately rubbed me the wrong way.
He planted himself next to me, kept addressing me, and tried his best to get me to take an interest in him.
But I couldn’t. And definitely not once I met his friend, Jason.
Jason was kind and respectful. He seemed interested in talking to me, but kept ceding the conversation to Adam. He seemed to be adhering to the bro code — his friend had already “claimed” me and all he could do was sit back and watch him fail to impress me.
Jason intrigued me, so I kept steering the conversation back to him. Adam tried repeatedly to bring the attention back on himself, but I would always find a way to place it back on Jason.
Adam wasn’t the subtle type, so it took a while for him to get the hint. But after an hour, he gave up his attempts at showing off to me and he got up and went to give someone else his attention.
Soon after, I was exactly where I hoped I’d be, sitting alone with Jason on a bench in the train lounge. Our conversation started off with music — as it turns out, we were both heading to the same destination and to the same concert — and moved to hobbies and whatever the fuck else.
Honestly, I can’t remember what we talked about. The conversation just flowed. I know we sat together for hours, but it felt like minutes flying by. It was the kind of conversation that could have lasted for days and still feel like it ended too soon.
What I do remember was how I felt drawn to him. It felt like there was a magnetic force gently pulling us together, and I wanted so badly to stop fighting it.
There was just something that attracted me to him. The most obvious thing is just how hot he was. A fit body and a face framed by deep brown hair and a well-groomed beard. And he seemed so mature — he was charming, interesting, and seemed so at ease.
I was the shy type who had a hard time looking people in the eyes, but that night, it didn’t matter. I couldn’t stop looking into his piercing brown eyes.
As our conversation unfurled, we slowly moved closer to each other. When our knees touched, the whole energy changed between us. There was no more will-they-won’t-they between us — we knew we were both into each other.
We started flirting more overtly. When he told me I was cute, all I could do was blush and thank him.
I should have splashed him with compliments in return. I should have told him he was hot as hell, that the only thing I wanted to do more than listen to him talk was put my lips on his, that he just had something about him that I found irresistible.
But I was too busy mentally comparing myself to my friends. They were thinner and prettier than me. He probably just went after me instead of them because I was the only one without a boyfriend.
Not being more open with my compliments wasn’t my biggest regret of that night. That one came soon after.
Our train came to a jerky halt and an attendant came to announce that the train had broken down.
We were slowly ushered out and herded onto a bus that would take us to our destination.
The entire time, I kicked myself for not making a move.
I should have pulled this guy into a bathroom, pulled his pants down, and stroked him until he was firm enough for me to climb on his cock.
I was sure I had missed my only opportunity to fuck the first guy I really felt drawn to in a long time.
We climbed aboard the bus at four in the morning. He sat in the seat in front of mine. He leaned his head back into the padded seat, and I hunched forward to rest my head against the hard plastic shell that held it in place. It was as close as we could get with a few inches of material between us.
Most of the other passengers soon fell asleep, but I wasn’t going to miss my last opportunity to spend time with this guy. We picked up our conversation and spoke softly to each other until the bus stopped at the train station.
We hugged. We smiled at each other. I tried to hide my slight sadness under a sheepish grin and a few layers of awkwardness.
How do you part gracefully from someone you feel such a strong connection to?
How do you even get over feeling silly — crazy — for having such a deep feeling for someone whose last name you don’t even know?
He squeezed me tightly, and in that moment, everything felt clearer. I never wanted him to let go of me, but at the same time I felt a sense of gratitude that I had met him, even though it was going to end as soon as he pulled away from me.
When we let go of each other, he told me he was really happy to have met me. I told him I was, too. And, more as a reflex than anything, I added “See you around.” I walked away feeling embarrassed at those last three words — what a stupid thing to say to someone you’ll never see again.
Tattoo My Heart
Exploring Montreal was a real thrill for a small-town gal. Everything seemed so bright and promising, like we could just walk down any street and have an adventure.
I walked down Saint Catherine street with one of my friends and we came across a place that did hand-drawn temporary tattoos. We each got one on our legs for the hell of it, but it left me feeling a little unfulfilled.
“That was fun,” I told her. “But do you know what would be even more fun? If they were real.”
She looked down at the art on her leg and offhandedly said, “Yeah, that would be fun.” And then her eyes slowly met mine when she realized I wasn’t kidding. “Wait. Are you serious?”
I nodded excitedly and I grabbed her arm and pulled her down the street until we came across a tattoo studio.
Once we got there, we realized that we were missing one important little detail: what tattoo we wanted.
We agreed on matching tattoos. She wanted a cute heart — something as sweet as sunshine. I didn’t really dig sunshine. I wanted something a little less sugary. But the heart motif made sense to me. I had just been dumped, and after spending an entire summer in an abusive relationship, I was feeling broken down but ready to find my path to healing.
Plus, I was seventeen, kind of emo, and super dramatic, so I declared that if I was getting a heart tattoo, it would be a broken one.
She grabbed a pen and sketch pad and drew a compromise: a black line drawing of a heart, cracked at the top.
We handed it to the tattoo artist and soon after we each had the same tattoo. Hers on her lower back and mine on top of my breast. I’d tell everyone that it’s because that’s where my heart is, but the truth is we both just needed a spot our parents wouldn’t see.
Marked with a broken heart, I felt ready to take my life into my own hands. I wasn’t going to try to make myself into the girl guys want — I was going to find a guy who liked me for who I was. I was through having bad sex to try to make someone fall for me — I was going to fuck for all the right reasons (because it’s fun, because I’m in love, because I’m horny).
That night, I did just that. I went back to my hotel room with John and took advantage of having a friend with benefits. I used to wish he would just like me, make me his girlfriend, stop playing games with me. Now, I realized I deserved more. But I was so fucking horny from flirting with Jason and fantasizing about the sex I could’ve had with him. I released some of that tension with some harmless hotel room fucking.
I spent a day with a charming man, saw an incredible concert, got a tattoo, and capped it off with some half-decent sex in a hotel. What more could I have wanted out of Montreal?
Semi-Strangers on a Train
On the ride back home, I couldn’t get Jason out of my mind. But I knew I had no chance of meeting a second powerfully attractive stranger, especially not on such a dead ride. Each train car we walked through was practically empty.
I decided to just stare out the window at the passing landscapes, fall asleep, and let the train carry me back to my boring, humdrum life.
My daydreaming was broken by a familiar voice. “Well, look who we have here.” It was Adam. My heart skipped a beat, hoping he wasn’t alone. I turned and saw Jason standing next to him.
I tried to keep my composure while I freaked out on the inside. I don’t know if I believe in fate, but being in the same train car as him again made it feel real.
We smiled at each other, and with all the fake confidence I could muster, I said “I told you I’d see you around.”
“I never doubted you,” he said and smiled at me a moment before inviting me to sit with them.
We made or way to their seats. I sat in the aisle across from them and we talked about the concert and our weekend.
I declared, with more showiness than I’m proud of, that I got a tattoo. Adam made praying hands, looked to the ceiling, and exclaimed, “Oh please tell me it’s on her ass!”
“You wish,” I snarked and tugged down my shirt to give them a peek at my freshly tattooed cleavage.
“Aww, did someone break your heart?” Adam asked in a mocking, condescending tone. “I bet I could make you forget about him.”
While I was still rolling my eyes, he turned to Jason and loudly whispered “I bet she tastes really good.”
Jason, seeing I wasn’t into any of this bullshit macho display, asked Adam to switch seats with him so he could be next to me. Adam begrudgingly agreed, moved to a seat behind us and fell asleep within minutes.
Night time rolled in, the lights were dimmed, and what few passengers were in the train nodded off. But we stayed up for hours, picking up our previous conversation like we were old friends. We rehashed all the good, the bad, and the ugly of our past relationships while he traced circled into the plaid pattern on my pants.
As the conversation became more flirtatious, his hand slowly made its way from my knee to my thigh. And just as I was starting to feel so wired with anticipation I could barely talk, he leaned in to kiss me.
Our lips touched softly at first, slowly lingering. It was so long overdue — it didn’t take long before we kissed firmly and passionately, making out with heart-racing eagerness.
I climbed onto his lap and straddled him, feeling his erection pressing against my crotch. I stroked his beard while we kissed. He ran his hand through my hair, down my back, and then up my shirt. He traced my curves with his palms before sliding them lower to caress my ass.
I spent what felt like hours grinding against his hard cock, wishing we were somewhere just a little more private so we could take things further.
In the middle of the night, a train attendant made her way to our car. I discreetly climbed off Jason and took my seat, hoping she would leave quickly.
She paused when she got to us and asked if we wanted anything. Jason asked for a blanket, and I knew I was finally going to make up for not pulling him into a bathroom the night I met him.
The attendant handed us two blankets and promptly left. We covered our laps and I reached under his blanket and impatiently tugged down the zipper on his pants. His cock surprised me the moment I grabbed it. It was shorter than any I’d ever encountered, but also massively thick. (To this day, I still refer to him as Soda Can Cock, with absolutely zero exaggeration.)
I stroked his cock while watching his face to gauge his enjoyment. He was hot when we were having a conversation. He was even hotter leaning back and letting me pleasure him.
He reached down and unzipped my pants, ready to repay the favor. I slouched and spread my legs as wide as I could so he could slip his hand down my panties.
We sat side by side wordlessly, quietly panting — my hand on his cock, his fingers inside me.
I could have let him finger me without end. Even in those awkward positions, he managed to make my pussy feel better than anyone else had. But I wanted to know what else he could do — and I wanted to know how that girthy cock would feel inside me.
I asked him if he had a condom, and he rummaged for it while I looked around to make sure no one was awake.
I turned around and kneeled on my seat, resting my arms and head on the back of it. I tugged my pants and underwear down to my knees while watching the two men sleeping in the seats behind ours.
I shivered from anticipation and the cool air tingling my bare ass. I arched my back and pushed my ass up, waiting for Jason to fuck me.
He positioned himself behind me as best as the cramped seating would allow and then slid the tip of his cock inside me. Even though my pussy was as wet as it had ever been, it took some easing to get him in. His thickness made me feel like I was being slowly stretched open.
I gasped from this entirely new sensation and buried my face in the seat to muffle my moans. It was too late though, I had already woken up Adam. But for the first time since I met him, he stayed quiet. He just watched as his friend fucked me from behind.
I didn’t even feel a tinge of embarrassment and I sure as fuck wasn’t going to stop. I was so fucking turned on at this point that I would have let the entire train car watch if it meant I could fuck this guy.
I felt absolutely blissful as he fucked me. I was praying he wouldn’t come too quickly. I wanted this to last.
Well, it didn’t. We heard the door open and he pulled out of me, scrambling back to his seat. (I guess he didn’t feel the same way I did about the whole train car watching.)
We threw the blankets back on our lap and the attendant announced that more passengers would be boarding soon so we would all have to go back to our assigned seats.
We zipped up, gathered our things, and wandered the train until we found a spot with some privacy. But the sun was up now, and the dawn’s rays made everything clear and bright. We wouldn’t be able to fool around anymore. I cuddled him quietly the rest of the way, still flushed from our unresolved fuck session.
My destination came first. We kissed one last time, said goodbye one last time, and parted ways for good.
There was no reason to cling to him. This time, when I stepped off the train, I wasn’t full of regret. I left Montreal believing for the first time that I deserved kindness, fun, and passion. My two nights with Jason confirmed that for me. I walked through the station feeling warm, satisfied, and completely alive.
Never More Than It Was
I spent years trying to understand that night.
What made it so damn good? What made it so perfect?
How does a one-night stand have any right being that amazing?
For one thing, he was good. Not every guy I had been with bothered using their fingers on me, and the ones that did usually made me more uncomfortable than aroused.
Jason knew what he was doing. He seemed to have some experience and put it to good use. No one else would finger me that well until I met my future husband a few months later.
He was also really into me, and that made everything feel so fucking sexy. There was some genuine chemistry between us and it sparked some real passion.
It’s sad to say, but very few of the guys I fucked would have spent that long just talking to me. And the ones who did couldn’t sustain a decent conversation to save their lives. This guy was interesting and interested, and that’s a combination that can’t be beat.
But a lot of it also had to do with knowing that this would be it. That I would never see him again.
When I fucked John, I had to go back to hanging out with him and the guys after. When I fucked people at parties, I knew I might see them around town.
When I fucked Jason, though, there was no pressure at all. We lived hours apart. I was seventeen. I wasn’t interested in a long-distance relationship. We didn’t have cell phones back then to bridge the gap. As much as I liked him, I knew there was no future between us. There was no reason to exchange numbers and promise to find a way to be with each other again.
It was just one night (well, two) and that’s it. Then we could forget about each other (not that I could ever forget him).
There was no need to worry about what he thought of me. No need to impress him. I didn’t have to worry that I’d somehow embarrass myself or not live up to some pornstar standards. Because I’d never see him again, I could just get out of my head and just be in the moment.
I could speak freely. I could touch him how I wanted to. I could explore his cock with my hand and find out what made him feel good. I could let him touch me and just experience it. I would bend over and take his thick cock while blocking everything else out of my mind (even Adam’s jealous stare).
It was the perfect one-night stand. But it might not have been if we didn’t part ways completely at the end.
Jason’s not a part of my life anymore, but I think back to that night often. That’s the night I learned I was worth more than the shitty treatment I put up with. That’s the night I created a memory that I still remember vividly today.
Now, when I look at my tattoo, I don’t think of the asshole who broke my heart. I think of the handsome stranger who helped mend it.
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