My [f] encounter with a stranger [m] at a Hawaii resort

Hey everyone, heard about this place from a friend, been reading the stories for a few weeks, and finally decided it’s time to share a story of my own! It’s a little long and kind of stream-of-consciousness, so apologies for that, but still hope you guys enjoy :)

A few years ago, when I was still in college, I went on this summer vacation trip to Hawaii with my family. We stayed at a really bougie resort in Maui that was just absolutely beautiful: white sand, palm trees, clear blue water, the whole thing. Unfortunately for me, though, I’d just gone through a bit of a rough patch relationship-wise (my boyfriend of all of freshman year got drunk and cheated on me with some slut), so I wasn’t really feeling the whole vacation thing as much as I usually would. That is, until I met Jason…

Let’s backtrack a tiny bit. On my second or third day at the resort, towards the evening, I was coming back to my room from the pool when I walked past a group of three teenagers, looked about my age or a little younger. They were very clearly smoking a joint just behind this palm tree that they must’ve thought hid them (it didn’t, like, at all). I don’t usually smoke weed, but I’ve tried it a couple times of course, and that night I had been feeling pretty down in the dumps so I figured what the hell and approached them to see if they’d share. I must’ve looked pretty dumb looking back on it, approaching some people I didn’t know in just a towel and bikini, still wet from the pool, but at that point I was feeling like just doing whatever and not really thinking things through.

So I walk up to the three teenagers and see that it’s one girl and two guys—one of the guys looked local, and the other two were white. As it turned out, the local guy was their plug, and the two white kids were brother and sister (the local was totally just doing this to get with the sister too, I don’t think Jason even realized). Yeah, the brother was Jason. He was a year younger than me, just out of high school at 18, with his sister another year younger than him. But let’s focus on Jason: wearing just his swim trunks, with a gorgeous cut body and that amazing thick dark hair that some guys have that seems to just always flop over their face in this perfectly artful way. So yeah, pretty hot.

He was holding the joint when I walked up, and offered it before I even finished asking. I remember smiling at him and asking his name, and him not even finishing saying ‘Jason’ before sliding his arm around me. I was surprised to find that I didn’t even mind—it just felt like part of some weird adventure. The four of us smoked a while longer (the local dude had like, three joints on him, it was crazy), just talking about our various lives. I found out Jason was going off to study engineering at Purdue. I told him about journalism school in LA (not naming my school for anonymity reasons), and he had some questions about college, etc etc. Eventually, the sister said she was feeling tired, and the local guy offered to walk her home. Don’t worry guys, I pulled her aside to see if she was feeling okay, and she was definitely fine with him, so there wasn’t any problem. After they left, Jason turned to me grinning and asked if I wanted to ‘hang out.’ I told him no, but we exchanged numbers and I said I’d text him the next day when I was sober.

The next morning comes and I’m feeling horny as hell from the dankover, so when my parents knock (we had those adjacent rooms) to see if I’m coming down, I tell them I’m feeling a little sick and probably coming outside later. Immediately I think of Jason, with his hair and his smile and all his earnest questions—he had treated me like some kind of mentor, someone worth listening to, someone experienced. It was different, and I liked it. I texted him, a simple ‘what u up to?’ to test the waters. Within seconds, I received a ‘idk, depends ;).’ Well someone doesn’t play around. ‘Room 305, ____ building’ I responded (don’t wanna give away the hotel). ‘Be there in 30.’ Amazing. A true millennial love story.

I took a really quick shower, minimal makeup, and was just pulling on my shorts when I heard a knock at the door. Electricity flowed through my body—I legit almost shivered. Trying to suppress my grin, I went and opened the door to see—housekeeping. Disappointed, I told the woman that my room didn’t need servicing today, and closed the door again. Not long after, another knock, and this time it’s Jason. I open the door—we exchange like four words—he leans in—I lean in too—we start furiously making out, hands all over each other, I’m feeling up and down his back with my other hand on his face, pulling him in, holding him close to me. He picks me up and I let out an involuntary gasp, wrapping my legs around his waist and laughing. He closes the door and carries me to the bed.

Hooking up with a stranger, I was expecting, like, rough and fast stuff, but we lay there kissing on the bed for probably twenty minutes, almost tender. It was like he instinctively knew what I wanted, what I needed. We held each other tight, passionate but slow, intense but measured, and I felt my whole body getting warmer with anticipation. Finally, I couldn’t take it anymore, and pulled away from him to take his shirt off. He turned over, lying on his back, and pulled me on top of him, kissing me some more before pulling my own shirt above my head and undoing my bra. It took him a couple tries to get my bra off, and I felt bad for laughing.

“This can’t be your first time taking off a girl’s bra,” I remember teasing.

“No, but it’s my first time taking off a woman’s,” Jason responded. I think I might have literally melted right then, were he not holding me together with his body. To this day I’m impressed with him for having that line ready so quickly—I hope that boy looked into improv in college or something!

I came away from his mouth and began kissing down his body, first his chin, then his neck, making sure to leave a nice mark. Then his chest, enjoying the tightness of his muscles, then down his abs, which were also amazing.

“Did you play a sport in high school?” I asked. I know, I do great dirty talk, it’s a prized skill of mine.

I think he said he played lacrosse, or basketball, or something. I was barely even listening at that point, because I’d just unbuttoned his shorts and pulled free his dick. I don’t know if it’s the most impressive I’ve ever seen, but to this day it’s the most impressed I’ve been upon seeing, if that makes any sense. Unlike most authors here, I didn’t have a ruler or a tape measure handy, so I’ll just hope it’s enough to say it was really thick, and definitely long enough ;)

I breathed it in for a second before wrapping my lips around it, slowly pushing it deeper into my throat. I’m no superman—I got about half of it down my throat before gagging, but I kept at it, running my tongue and lips up and down his smooth, thick shaft. His appreciative grunts and gasps only served to make me hornier (pro tip guys, y’all can make noise too) as I blew him, and before long I’d had enough of the appetizer. It was time for the main course.

I came up for air, and more making out, before rolling onto my back and uttering the magic words all boys love to hear: “fuck me.” Jason was only too happy to oblige. He pulled my shorts and panties down at once, pawing at me in an almost animalistic way. He positioned himself above me, dipping his head down for another series of intense kisses, before rubbing his tip against my clit and eliciting a loud moan. There was a brief interlude as I asked him to put on a condom, he asked why, I stared at him for five seconds, and then he grinned and put one on. Then we were right back at it. He teased me endlessly, rubbing up and down, pretending he was about to push in before pulling right back out again, until I grabbed his hips and told him I needed it NOW. He laughed and then suddenly thrusted deep into me—all the foreplay plus the sudden shock made me immediately come, which was such a surprise I think I almost came again. Shit was wack, man.

He began thrusting in and out, long, deep strokes, measured and rhythmic. I lost myself in the motion, in the sensation of being full, of him sliding against my inner walls. I don’t even remember if I made noises—I could’ve been silent or as extra as a porn actress. All I know is that it felt amazing. He rolled over, still inside me, and I started to ride him, barely holding myself together on each thrust. His fingers drew circles around my nipples, then started to lightly pinch and pull at them, which only increased the intense arousal I was feeling. We fucked in that position for what felt like hours, and I came two more times, which is almost unheard of for me. Finally, he gasped something out.

“I’m close!”

Something took hold of me then, some wild, animal mania. I pulled off of him, pulled the condom off, and lay on my back. “Inside me,” I moaned, knowing somewhere in the back of my mind that I was on the pill, but more importantly in the front of my mind not caring about any of that. He paused for an instant, but something about my expression must have convinced him—he slid in fairly easily, my wetness and his precum more than enough lube. The feeling of him without a condom was unbelievable—it was like I could feel every ridge, every part of his penis. It was like we were truly connected. He gasped suddenly and I felt a warmth within me. Believe it or not, at that instant, with his final thrust, I shook with yet another orgasm. He collapsed on top of me, leaving his dick inside for several moments before pulling out and rolling off. Immediately, I pulled him in for a kiss, no longer of passionate hunger, but of simple sexual connection.

Of course, minutes later I realized what a f***ing idiot I’d been, and we had a frantic conversation about whether or not he had any STIs. I assured him that I was on the pill, that no, I’m not a crazy woman trying to have his kid, etc etc. After that, we ended up cuddling on the bed for almost an hour, watching dumb cooking shows on the hotel TV. He asked if I wanted to go again, but I felt like more sex would tire me out too much—at that point, I was perfectly energized, refreshed from an exhilarating encounter with a stranger. We put our clothes back on and kissed each other deeply.

He said he’d see me again soon. I said nothing. Ten days later, I got on a plane back to San Francisco. He never did see me again, but we still sometimes snapchat, sending hot pics or nudes every once in a while with barely any other context. I don’t know why I didn’t text him again that vacation, but something made me feel like that one-time encounter was the perfect way to leave things.

Sorry for the stream of consciousness writing but I was just feeling rly horny and wanted to write this all out quickly while I was feelin it. Hope you guys and gals enjoyed the read!

Source: reddit.com/r/gonewildstories/comments/7atqmu/my_f_encounter_with_a_stranger_m_at_a_hawaii