**Background**
I was 18 at the time and had just graduated high school. Up to that point I had only slept with my high school girlfriend, but we had broken up a few months prior. Just a few days after returning from a Hawaii vacation that I got as a graduation gift, my family took its annual trip to a resort in Cancun this time. I really shouldn’t have spent so much of my graduation money in Hawaii, because in Mexico I was of age and could have had way more fun at the clubs. My family prefers the convenience of filling up our hotel suite’s kitchen at the start of any trip. Knowing I would be stuck at the resort, I made sure to stock up on beer for myself when we were at the store.
**Lead up**
It was my second night in Cancun and I had so far only spent time with my family. I was college aged now, and legal to drink. With college around the corner, I wanted to do what I thought always happened in places like this to people my age: get drunk and hook up. I had always been shy around girls and extremely insecure, which most people wouldn’t expect because I was known for being outgoing and flirty. Knowing I wouldn’t have a problem making friends I filled my backpack with my first legally purchased beers and let my family know not to wait up for me.
I ventured off into the sprawling beach resort, feeling like a real adult. But really, I was just a horny teenager hoping to have his first real hook up. I made my way to the massive pool. This thing reached all over the resort. At some points it was just a shallow water feature with a fountain and a bridge to walk over, others it was a play area with slides, sometimes it was a jacuzzi, just this big connected pool by the beach surrounded by jungle, ocean, and luxury.
I was out on my own for the first time and hoping to find trouble. As I’m walking I hear a ton of banter in the distance. Drawn to where I think the fun might be, I stumble on a section of pool with a volleyball net and a swim up bar. There’s a big group of people playing, chatting, drinking, and goofing around. Perfect. I’m looking for a place to leave my stuff and notice a mostly empty cabana with a group of drunk older women nearby. Ready to take advantage of my teenage charm, I ask if they mind me leaving my stuff there. They don’t mind one bit and start chatting me up right away. Before I know it they let me in on their plans to catch the next shuttle to the clubs. Unsure about having enough to spend and on my own, I was too nervous to leave the resort. Instead I decline, grab a beer, and jump in the pool to join the shenanigans.
Next thing I know I’m playing volleyball, chatting with strangers from all over, and getting increasingly drunk. I was a bit surprised at how quickly I got along with everyone and was disappointed when the last shuttle showed and most of my new friends (including the cougars) left. There was a small group of us left, all dudes except for a few couples that were slowly trickling back to their rooms. We were still having a blast, though.
Eventually, a girl shyly walks up and distracts the game. The light from the pool shining on her pale skin was hard to ignore. Plus, she had an amazing ass. My closest teammate blurts out to me, “dude”. Me responding, “I know”. Not wanting to be obvious, the game picks back up immediately, rowdier this time. She’s sitting with her feet in the water when I swim over to offer her a beer and invite her to join the game. She accepts. It went something like…”Hey, I’m Ben”, she giggled, “Sabrina”, “want to play with us?”, “sure”. She strips down to her thong bikini and hops in. I’m pretty proud of myself.
Our teams were uneven since someone played waterpolo and we wanted to keep things fair. Unfortunately this meant she went to the other, smaller team. Waterpolo guy was in good shape, and what do you know she’s positioned right next to him. Great, I just set them up, there goes my chance. “Smooth move, idiot”, I think to myself.
Waterpolo guy starts getting cocky and my team gets a huge lead. Now the smaller team is complaining and they start re-picking teams. I hop out to grab my Nth beer from my now empty cabana and what do you know, the only single girl there swims up me to ask me for another drink. The group interrupts “BEN! Which team?”, I let them know I’m sitting this one out. “What about you?!”, they ask Sabrina. She glances at me and smirks then responds back, “I’m sitting out too”. I help her out of the pool while the rest of the guys continue the game, deflated.
We sit down next to each other in the cabana bed while I grab our drinks out of the bag. Making small talk we find out we’re both here from California and stuck on a family trip. In an effort to assert my adulthood I had bought a pack of cigarettes with my beer. I make sure she doesn’t mind me smoking as I l light one up and lay back on the bed next to her. Turns out we’re also the same age and listen to the same music. She asks about my festival experiences but I hadn’t been to my first concert yet. “You have to go”, she tells me. As I’m laying there listening to her rave stories, she leans back into my arm. Instinctively, I wrap it around her and start moving my thumb up and down against her side. Keep in mind, it hasn’t even been an hour since we met. My drunk and horny teenage self is losing his mind.
Not only do we like the same genre of music, we’re fans of the same artists. She lives a few hours away from me and we play with the idea of going to a show together back home. Are we hitting it off? I think so. At some point I had started running my hands through her wet, dark, curly hair. The contrast to her light skin was intoxicating. We both pause and she looks up at me. We kiss.
**Sexytime starts here**
Our kiss gets deeper and my hand runs down her back closing into a fist inadvertently tugging her hair. She leans her head back and moans, exposing her neck. I dive in. I start licking and kissing her neck. Her fingernails dig into my back as I let her hair go and let my hand wander to her hip. “That was hot”, I think. We continue our conversation gradually leaning further into each other. Her head was on my shoulder, but now it’s on my chest. Our legs were side by side, but now they’re tangled up. Fully cuddled, I was trying not to make my boner obvious. We quickly got back to making out. I grab her ass and press up against her. Now she knows I’m hard, oh well.
To my surprise, she grinds into my hard dick and I can’t help but moan and throw my head back. This time she’s in my neck I am loving it. I’m groping her ass and her bikini string is wrapped around my thumb while she goes to town on my neck, biting and sucking it while running her nails through my chest hair. The second she stops I dive back into her, kissing my way down to her cleavage. She loves it. We’re basically dry humping now and I’m doing my best not to pull her bottoms down when my free hand reaches up to feel her c-cups and pulls her top down just enough to set a nipple free. Of course I suck on it. The people in the pool notice, we can sort of hear their comments over our slurps and moans. We decide we need some privacy and head towards the beach holding hands. At this point I was rock hard and using a towel to cover it up as we walked.
We find the beach a few steps away covered with lounge chairs and day beds with no one around, hell yes. Being both from California, we love the ocean and let each others hands go to run into the water. We splish, we splash, we laugh, we bring our bodies back together to make out more. The tide goes up and down around our feet and she presses herself against me. I can feel the warmth of her pussy against my leg. The head of my now throbbing dick pokes its way out of the top of my shorts. Knowing she’s just as wet as I am hard, I’m not embarrassed anymore. She notices, grabs onto it, and gives it a stroke, pulling my shorts down a bit. By this point we’re struggling to maintain balance and giggle our way to one of the resort’s beach beds.
We’re standing next to it and I push her backwards onto the bed. She’s on her back and a climb up onto her, cock lined up to her pussy. She’s grinding my shorts down further and I decide to just pull her off her top and kiss all over her body, down towards her pussy. My dick still peaking out of my shorts with her top now completely off. We were both exposed and neither one of us cared. Waves crashing. Damn, this is awesome.
With my shorts falling off, I kneel into the sand and move her bikini over so I can start eating her pussy. It tasted amazing. Eventually her bottoms are up to her knees and I’m underneath them with her foot on my shoulder, finding and licking her clit with my tongue. Having had a girlfriend before, I slid my finger into her hoping to find my second g-spot. I quickly learned that as sexy as the beach can be, sand is not your friend. So, I went back to just eating her out. At some point her bottoms came off too and she was completely naked. I would take a break from eating her out to kiss her and she would grind her wet pussy against my exposed dick. But we couldn’t have sex, we just met. By about the third time I stuck my head between her legs she grabbed the back of my head and slammed her thighs into my ears letting out a huge moan. Using just my mouth and not my sandy hands, I managed to make her cum. I didn’t stop licking her until her legs were in the air shaking and she couldn’t take anymore. I stoop up proudly, letting my shorts finally fall to my ankles. She laid there for a second and caught her breath then eventually looked up and let out a quiet, “damn”. I wasn’t sure what she meant but took it as a good thing because she sat up and grabbed my ass, eagerly taking my dick into her mouth. It was my turn.
She grabbed onto the back of my thighs and started sucking. There I was, with a beach breeze on my ass, getting a blowjob. Fuck yeah. I noticed a hotel employee putting things away in the distance. Worried about getting caught I told her to stop. By the time she stopped and looked around he was gone and we realized we didn’t care anyway. I grabbed the back of her head and guided her mouth back onto my dick, thrusting forward. She gagged. “Sorry”, she said. I ask why and she answers, “I’ve got a small mouth and you’ve got a big dick.” Really? Hell yeah what a compliment! “It feels great, don’t stop. How about we switch spots and you do your best?”.
Now I’m on my back on the bed and her hands are crawling up my legs as she bring her mouth back onto my dick. Oh what a feeling. I’d get close to cumming but she kept needing to stop to give her mouth a break. She’s got the biggest rack I’ve played with up to this point so naturally I ask if I can try fucking her tits. She’s down, so we get as much sand off ourselves as we can and she pushes big soft pale her tits together. Now she’s on her back and I give her chest some sloppy kisses before straddling her. Hormones raging, my hips were eager to thrust. With my ass catching the ocean breeze and balls resting on her, I start fucking her tits. It feels amazing. Having never done this before, I was surprised to find my dick slid through her tits out far enough to reach her mouth, like in some porn. She noticed too and leaned her head forward enough to pop my tip in and out of her mouth as I thrusted. The head of my cock was literally making popping sounds as I slid between her tits and mouth. I would occasionally still try to play with her pussy but gave up as I was in heaven myself.
Teenage lust took over as I thrusted away. “Mmm yeah how’s that feel?”, I asked hornily. “Ehh, like you’re sliding your dick on my chest”, she answered honestly. We laughed. Realizing my lust was the only thing needing taking care of at this point and how uncomfortable the titty fucking blowjob was for her, we decided I should just lean back and let her take care of me.
She said she’d do her best, only being able to fit about a third of me into her mouth. She’d kiss and lick my dick where it wouldn’t fit into her mouth while gently massaging my balls. I had no complaints. Occasionally my hips would jerk forward reacting to the pleasure and make her choke. She’d tell me to be careful then let off and find somewhere else to put her mouth to catch her breath. I could feel my orgasm finally building and did it again, accidentally. This time her mouth found its way to my balls and I found my new favorite feeling. Getting my balls licked. I was too close to not cum and reached down to jerk myself while she lapped away at my balls. My junk was covered in slobber and I loved it. It only took a few strokes and I let her know I was about to explode. She pushed my hand away and sucked my tip just in time to catch the first spurt. I twitched in ecstasy while unloading into her mouth. Like every guy, getting my dick sucked while I cum just makes me cum harder. She swallowed every drop. After our heavy breathing subsided the realization that we were butt naked in public set in so we got dressed. We headed back to the pool expecting to find our friends, but it was empty. Apparently we had been gone awhile.
Our rooms were opposite of each other so we parted ways and headed back to our separate rooms, glowing. I ran into a volleyball teammate on my way back. “Someone had a good night”, he said. “Oh yeah”, I replied. I reached my room and went straight to bed, feeling accomplished.
Source: reddit.com/r/gonewildstories/comments/iywcc3/my_first_hookup_ever_cancun_pt_1_mf