Vacation fling, with a twist [MF]

Anyone who’s been to a destination wedding knows that it’s the people you’re with that makes or breaks the experience. For me, a late-twenties male, the best destination weddings I attended were the ones where the other wedding guests were fun, energetic, and adventurous. This was not one of those times. I love my family, but I’ll be the first to admit they can be boring people. They’re too shy to try new things, they go to bed early, they only stay on the resort, etc. So as a result, the first few days of a distant cousin’s wedding in Cancun were less-than-ideal.

Although the weather was great and the booze was free and unlimited, there’s only so much sitting by the pool that I could handle while my father lounged in the chair next to me, finishing his 138425th Sudoku puzzle. I had cabin fever, and it was clear that the people in our wedding group weren’t going to help me solve it. So I got up and wandered off to try and find something to do.

I walked along the beach and observed all the classic resort staples: local vendors trying to sell overpriced boat trips to naive guests, overweight retiree couples slathering thick sunscreen on each other’s backs like mayonnaise on a sandwich, wanna-be instagram models doing their staged photos in skimpy bikinis in the shallow water, etc. I kept walking along the beach until I heard laughter among the background music blasting from the swim-up bar. I walked in that direction. I found a game of beach volleyball going on with 7 people playing; 4 dudes and 3 girls, seemingly all around my age.

Maybe it was the boredom, maybe it was the Blue Hawaiians, but I felt emboldened enough to ask the nearest girl playing if I could join in. She quickly looked me up and down, smiled, and said “Sure! You can join our team since we’re down a man”. I took off my shirt, revealing my 3rd-day-of-vacation tan and visible abs. Her gaze lingered a bit longer and I returned the favor. She had a very nice body, mostly fit but with a hint of extra curves in the places you’d want them. Her hips looked like something you could grab onto for days. Her tits were average size, matching her frame, and they were held in place by a thin, floral bikini top. She was wearing blue workout shorts which wrapped around her plump ass.

I played a few rounds with her squad. We didn’t keep score, we just played for fun. It was clear to me that her gang did not have much athletic experience, as most of the rallies were short. But I did notice I was getting turned on watching the girl’s body move. After about half an hour, the other side said they were done. The girl and I looked at each other.

“I’m Jess, by the way” she said to me.

“Tyler, thanks for letting me play!”

“Anytime, but I feel bad because you’re clearly a lot better than us.”

“Nahh you guys were fine, I just played a bit back in high school. But I’m clearly out of shape now because I’m bushed. Let’s go get a drink?” I asked.

“You are very much not out of shape,” she flirted, “yeah, let’s go to the beach bar, this rounds on me!” Classic, lame, all-inclusive bar joke.

We sat under an umbrella with our cervezas and chatted about what brought us here. Surprise surprise, she was also here for a wedding, for her friend from University. I lamented about being stuck at a wedding with extended family I wasn’t really close to. She sympathized with me, saying “..and it must be hard when weddings make you horny and you’re only surrounded by relatives.” This girl wasn’t playing around, and I wasn’t one to miss a hint like that.

“Fortunately the resort is full of hot girls who might be willing to take me in.” I said back with a smile.

Our flirting went back and forth, and it was painfully obvious we were going to fuck. I was ready to go back to her room right then, but unfortunately it was her last day at the resort, and her squad was doing one last get-together dinner before going home. We made plans to meet up in her lobby later that evening. We hung out a bit longer that afternoon, until she took off to go get ready for dinner.

In the meantime, I ate my dinner and then jerked off in the shower. You guys know how it is. It had been a while since my last time, and I didn’t want to bust a load as soon as I got her clothes off.

9 o’clock rolled around and I met up with her and her group in the lobby. She was in a classic tight little black dress. Her long brown hair was loosely curled, and her face was fully done up in makeup. She looked amazing. I tried to dress up a bit too, wearing casual pants and a dress shirt. She smiled when I walked up to her and she introduced me to her friends, most of whom were at the volleyball game. It was a little awkward socializing with them. They had all known each other for years, and with how much Jess was hanging off my arm, it was pretty clear what was going to go down between us.

Nevertheless, we all moved to the night club and had a great time drinking and dancing into the late night. Or at least I thought we all were having a great time. It was late and Jess’s seemingly closest friend pulled her aside and was saying something in her ear before hastily exiting the club. Jess then took me outside into the quiet night and explained to me that her vacation-roommate, Kelly, was involved in a dramatic love triangle with one of the guys and another girl in the group. I guess she tried to hook up with this guy tonight but the other girl ended up winning out, so Kelly just went back to their room to go to bed. Jess said she was done with dancing too, and wanted to go back to my room.

Uh oh. I never told her that I was sharing a room with my father, so that wasn’t going to work out since he was probably fast asleep.

“Ugh, fuck. Okay. Guess we’re going back to mine.”

“Is that okay? Is Kelly going to be pissed?”

“She’ll be fine, she’s done it to me before.”

Still tipsy, we stumbled back to Jess’s room. We sneak inside and Kelly was in her pajama shorts and a tank top, brushing her teeth in the bathroom. She was clearly surprised to see us, and she raised her eyebrows at Jess as if to say, “Really?”. Jess brushed it off and just said “Hey!” and we collapsed on the bed, making out. Kelly turned off the lights, went to her bed, got under the covers, put in her earbuds, and turned her back to us.

I unzipped Jess’s dress and helped pull it off of her. She was wearing a strapless bra and no panties. I took off her bra as she fiddled with my belt buckle. Soon we were both naked, and I crawled down to start eating out her pussy. She gasped and quietly moaned as I worked my magic. Her pussy was smooth and tasted a bit sweaty from all the dancing. I licked up and down her slit as she tried to stifle her moans.

When she had had enough, she pushed me off, flipped me over, and began to return the favor. She took my whole cock in her mouth and started bobbing up and down. I sighed and grabbed a handful of her hair. It was especially hot outside today, so we were on top of the covers. I glanced to my right and Kelly’s back was still turned to us. I had never had sex with an uninterested participant in the room, so this was a new thrill I never knew I needed. I felt an urge to make more noise in an attempt to get Kelly’s attention. I wanted her to see us. When Jess took me especially deep, I let out a louder moan. Jess stopped and looked up at me with her eyebrows crossed, then over at Kelly who still hadn’t moved. She smiled a wicked smile and went back to business.

She eventually stopped and whispered, “Condom?” I grabbed one out of my pants that I brought and handed it to her to put on. “Ribbed condom, what a gentleman you are!” she whispered sarcastically as she mounted me in cowgirl. She started riding me quietly, and arched her back which presented an amazing view of her full tits. As she bounced, they bounced. I was mesmerized watching this girl I barely knew work her way up and down my cock. I reached out with my thumb to start rubbing her clit as she rode, and as soon as I made contact she let out a loud moan. She then quickly cupped her mouth with her hands and looked over at Kelly again. I pressed harder with my thumb and she groaned and whimpered as she tried to keep quiet. Feeling bold, I reached up with my other hand and pulled her hands off her mouth. She gasped and playfully pushed my hand away, but left her mouth uncovered and moaned loud enough that Kelly could definitely hear.

She started riding harder, and it became almost like “the penis game” between us where we would go back and forth moaning, each time tempting the other to be louder and louder.

“You guys are actually making it impossible to sleep” suddenly came a voice from the other bed.

Jess squealed and covered her tits with her hands. She looked over at her friend, whose face was illuminated by the moonlight through the window.

“Sorry! We’ll try to keep it down!” I could tell that she was generally embarrassed. I think she didn’t expect Kelly to actually say anything or look at us, even if she was listening to the whole thing.

“Don’t worry about it, at least someone is getting laid. Don’t let me cockblock you.”

Jess still seemed unsure, but I graciously took Kelly’s self-deprecating permission and resumed fucking her from underneath. I looked over at Kelly and her eyes were wide open watching us.

This whole experience was unlocking something inside me that I never knew existed. I loved having an audience. I felt like such a stud. I started fucking Jess faster, rubbing her clit harder, and squeezing her hip with my free hand. Jess was losing it, her moans were becoming more hoarse and she stopped bouncing, instead letting me do all the thrusting from below.

“I’m gonna cum” she whispered, right before she clamped down and let out a huge moan. Her legs were shaking and she squeezed my chest with her hands. I kept thrusting as her whole body trembled. As her orgasm subsided, she collapsed on top of me.

“That was fucking hot” said our audience of one, and we all laughed.

“Any requests?” I asked Kelly.

“What do you mean?”

“What do you want to see next?”

“Ohh, ummm.. whatever..” She seemed shy now that I had outed her on her voyeurism.

I gently pushed Jess off of me and positioned her on her knees, so that she was facing the head of the bed in doggy-style. I turned on a small lamp, then knelt behind her so that we were parallel to Kelly. I positioned the head of my cock in front of her wet opening and looked directly at Kelly as I slid inside. Jess moaned as I veeeerrry slooowly fucked her. I had both my hands on her hips and was pulling her onto me as I thrust. She reached back to rub her clit.

Although I couldn’t actually see Kelly’s body, the bed covers were thin enough that I could tell she had one hand on her chest and one hand between her legs. While I was thrusting, I imagined myself as a porn star and adjusted my posture to try and show off my muscles a bit for the crowd. Whether intentional or not, Jess seemed to also present herself to Kelly. Her back was arched, her legs were spread far apart, and her hair was flipped to the other side of her body so that Kelly could see her entire beautiful face. Jess was moaning louder and louder as I fucked and Kelly had lost all subtlety as she aggressively fingered herself.

I smacked Jess’s ass and reached forward to pull her hair as I fucked her faster and faster. I felt the need to cum start to build up, and knew I wasn’t going to last much longer.

“When I pull out, I want you to flip over onto your back” I told Jess. She moaned her assent.

After one more extended look at Jess’s amazing curves, I hit the point of no return. “I’m gonna cum” I said as I pulled out and ripped off the condom. Jess obediently flipped over onto her back, grabbed her tits, closed her eyes, and opened her mouth, sticking her tongue out. I shuffled up and hovered over her body while jerking off my dick through my orgasm. The waves of pleasure rushed through me as I unloaded several ropes of cum all over her tits and face. After a whole day of flirting and teasing, it felt amazing to finally release the buildup all over this beautiful girl. When my dick was spent, I sighed and laid down next to Jess.

“Wow, good work guys” was all Kelly said to us. Her face was bright red. She turned her back to us once again.

Jess and I cleaned up in the bathroom together, whispering about how crazy that was. Jess told me about a time where Kelly had slept with her ex in the same room as Jess once, but she never saw anything. After we cleaned up, we turned off the light and snuggled a bit, but decided it would be best if I went back to my room. We said our goodbyes, and that was the last I ever saw her. A single-day fling with some excellent company on an otherwise boring vacation.

Source: reddit.com/r/gonewildstories/comments/dah8et/vacation_fling_with_a_twist_mf