Cancun with Kyle Gay Male

All parties are 18+.

I met Kyle freshman year in a Humanities 101 class. He walked in 5 minutes late to the class and sat next to me in one of the last open seats available. It was obvious he’d taken a nap before class and overslept; he had bed head and he was in sweats and a muscle tee, obviously no underwear on underneath as I could easily make out his dick swinging back and forth before he sat down. He smiled at me, cracked some lame joke I forgot immediately, introduced himself and that was that, apparently we were friends.

After the end of that first class we exchanged cell numbers, I figured a dopey straight dude as a friend we be fun at least and he seemed the type that overflows with golden retriever energy. Over the next couple of years, Kyle and I became fast friends. He had no issue with me being openly gay, making a joke about being my wingman when I came out to him and never once changing the way he treated me.

Kyle and I would work out two to three times a week at the university gym, he’d go almost daily but my schedule was a little tighter than his so I couldn’t always make it. It never failed, after we finished working out that he’d strip down in the locker room almost immediately, shamelessly strutting his stuff without a care in the world who saw. At first I’d avert my gaze, but it got to the point where curiosity won out and I looked. Kyle was hung, even soft. His uncut dick must have hung six or so inches soft and was girthy even completely limp and hung over two huge, low hanging balls.

Kyle’s size became well known in the dorms within a couple of weeks, his overall lack of care about clothing carried over to trips to and from the showers and most people quickly got a full sight of his summer sausage. All of this to say once word got around, Kyle was extremely popular with the girls. The man had a constant stream of women coming to his dorm room and he always seemed to treat them well. He didn’t date long with anyone, moving on quickly, but he also never strung anyone along. Kyle all in all was an upstanding dude and just about everyone liked him.

Our Junior year in college a group of eight of us decided to go on a big trip for Spring Break, settling on Cancun pretty quickly. The weeks leading up to it were filled with group planning, laying out a general budget, places to stay, traveling logistics, etc. Kyle laid claim to me as a roommate fairly early, to no one’s surprise. Out of the entire group we definitely were the closest, spending most of our free time together when we weren’t otherwise engaged.

The flight down was pretty nondescript, all eight of us got on the plane and mostly passed out for the ride. Once we landed we got to our hotel and setup shop, four double rooms each with a queensized bed.

Walking in, Kyle threw his suitcase in the corner of the room and immediately made his way to the bathroom to take a piss. “Dude I can’t wait to go down to the beach and start checking out women! There’s got to be so many smoking hot ladies out there just waiting to meet me!” Leaving the door open was nothing new for him, boundaries weren’t much of a thing for Kyle and I was used to talking with him through various activities.

“Yeah, what you going to do with them if you do meet someone? We’ve got the one bed and I’m not down to join in.”

“I dunno man, we’ll figure it out once we get to it. I’m just horny as hell and want to see what I can pull out here. It’s been a while since I last got laid.” Walking out of the bathroom, Kyle started shucking his clothes, stripping naked as he walked over to his suitcase and started rooting around. “I think I’m going to go down to the pool at least and check it out, you wanna come with?”

“Yeah, let’s see what we’ve got out there, water sounds nice.” I quickly stripped as well and hunted down my swim trunks. I wasn’t as ripped as Kyle was after all the work he put in at the gym but I did pretty well for myself. I was just short of a cut six pack and was damn proud of it and kept what hair that grew on my chest and junk trimmed short. While I didn’t pack what Kyle had, I was doing pretty good in the dick department as well, I hung maybe three to four inches soft and got up to seven when fully hard. Hadn’t had any complaints from the few guys I had hooked up with.

“Come on gay boy, let’s get going!” Kyle was already out the door by the time I tied my trunks and got some flip flops and the room key. We head down to the hotel pool and were met with an expanse of mostly naked people, most around our own age and all looking for fun. The next few hours were filled with fruity drinks, stupid shenanigans and eventually a run for food at some touristy burger restaurant with the other dudes.

Around 9 that evening I was mostly drunk, tired from the travel and sun and ready to chill for the evening and pass out. Kyle had given his best to see what he could pull on the first day here and struck out, his brand of charisma not seeming to match up with any of the girls he talked with. Our group all decided to call it for the evening and headed back to our perspective rooms to chill with an agreement to meet up for breakfast the next day.

Once in the room Kyle immediately flung himself on the bed and started channel surfing. Wanting to get the chlorine off me, I ducked into the bathroom and jumped in the shower for a quick rinse down. I didn’t spend long in the shower, just enough to quickly get clean and dry off. Dropping the towel to the bathroom floor, I walked out into the bedroom naked and came out to Kyle watching some cheap softcore porn with his hand down his shorts.

“Dude, what’s going on?” I laughed, shocked at what I had walked into. While Kyle had always been fairly open with nudity and his body, we had never done anything remotely ual around each other. I’d only ever seen his limp dick, never him when aroused even the few times I had tried to sneak a peak of his morning wood hadn’t worked out.

“Sorry dude, I’m freaking horny as hell after all that today! It’s been so long since I’ve got any and I’ve just been super keyed up.” He only briefly glanced over at me when replying but never stopped what was going on under his shorts, a large bulge extending the front out obscenely.

“I thought you and Kaley were going out pretty frequently.”

“I mean we were but she never wanted to do anything and then she got busy with class and that ended. Haven’t had much luck after that.” Finally he pulled his hand out of his trunks, still leaving a massive tent for me to see. Despite my best efforts, blood rushed to my cock and I could feel it lengthening at the sight of my friend’s covered hardon.

Kyle glanced over at me again, doing a sweep of my naked self, seeming to pause on my crotch which was something I’d never observed him doing before.

“I actually wanted to ask you about something but you’ve gotta promise not to say anything to anyone.” His tone was serious and somewhat hesitant, something I wasn’t used to coming from Kyle.

“Yeah dude, what’s up,” I started moving over to my suitcase to grab a pair of boxers, trying to cover up my hardening dick anyway I could without drawing attention that I was getting turned on by the scene in front of me.

“Well you remember how I was seeing Erin at beginning of the semester? She was into some kinkier shit and got me to try some stuff out. And I liked it a lot but then she turned out to be a bit too out there and I ended it.” Again his voice was quieter, hesitant to bring it up.

“Nothing wrong with trying out some new stuff. What kind of kinky stuff was she into?” Kyle and I rarely talked about stuff but it came up occasionally. Even though he was extremely gregarious, Kyle kept a lot to himself until it built up and then he’d turn to me once he needed a sounding board or someone to vent to.

“She really liked pegging and turns out I really do too. But how do you bring that up with someone without weirding them out? And since I broke it off with her it’s all I can think about.” He seemed distraught as he confessed, like he had tried so many things and couldn’t find a solution to his problem.

“I mean if you can’t find a girl that’s into it, just get a dildo or something and do it to yourself. There’s plenty of stuff out there, you should be able to find something that works for you.” I was a bit thrown off by the topic honestly, Kyle was the last person I would think to be into ass play, while he had never shown himself to be homophobic in the least, he seemed outwardly to be more conservative in his ual desires.

“Dude I’ve bought three of the damn things and it just doesn’t quite work for me. I keep wanting something more and it’s annoying as hell.” Kyle took a deep breath, seeming to gather himself. “I’ve been thinking about it a lot lately and I want to try something.”

“Like what dude?”

“Would you help me out?” Kyle’s question was quiet and a little pleading. “It’d be a bro thing, something between us but I really want to try it and you’re the only person I could trust with something like this.”

“Dude, what, you’re asking me to do what? Fuck you?” I was completely taken off guard by this. Kyle was straight from everything I’d experienced in the last few years and this was messing with my head. “This is the liquor talking, you’re drunk.”

“Nope, I didn’t actually drink that much. I’m just a bit buzzed. Please dude, help me out? Jerking off isn’t really doing it since I came with Erin’s toy in me and now I keep thinking about the real thing being out there and it’s all I can think about.”

Having my best friend in front of me, obviously hard and pleading with me to fuck him was doing crazy things to my head. I would have never bet in a million years that he’d ask anything close to this of me. The more I thought about it, the hornier I got at the idea, my boxers covered cock quickly rising to attention and causing a large tent.

Looking over at my friend on the bed, I allowed myself to look at actually look at him instead of avoiding horny thoughts like I had forced myself to all this time. Kyle was maybe 5’10” with the epitome of a jock frame, with large pecs and a solid six pack that he so loved to show off at the barest excuse. He kept his chestnut brown hair long enough to occasionally pull back into a small manbun that everyone hated but he thought was y as hell. With his bright green eyes and killer smile, it was no wonder he was able to keep his bed occupied most nights. Now those eyes were turned on me with an almost desperate, pleading cast to them.

“If I agree to do this, you don’t get to bitch out tomorrow when you’re sober and starting thinking things through. You have to be the same friend tomorrow as you were yesterday to me, no ghosting me. If you struggle with this, we talk it out.” I couldn’t take that look, I never could. This dude could talk me into anything, even crazy shit like this.

A grin lit up Kyle’s face at my response. “Zach, dude, you’re stuck with me. Even if it’s not my thing and I’m not about it going forward, we’re still going to be best buds.”

Sighing in resignation, I just nodded at him. “We better be. Alright, how we going to do this?”

Grinning even harder, Kyle lifted his hips off the bed and shucked his swim trunks. Coming face to face with his massive hardon, my breath hitched for a second. This thing was easily pushing eight inches or more and thick as fuck, his foreskin was pulled back completely and the head of his cock was engorged and an angry red. Kyle never kept any pubes on him, shaving them off consistently, causing his massive cock to stand out even more on his body.

“Damn that thing is huge dude!” I was gob smacked at the size of it, I knew it was large but not that big.

“You can play with it later but I really want need to get fucked right now.” Kyle scooted to the edge of the bed, planting his feet on the bed and canting his ass up a bit to present his clean shaven hole to me.

Sighing somewhat in resignation, I grabbed a small bottle of lube I brought with me and dropped my boxers, my pin straight hardon pointing directly at my friend. Approaching him, I quickly lubed up a finger and began playing with his hole, applying a good bit of lube to get things started. As soon as I made contact with him, Kyle closed his eyes and a quiet moan escaped him. He was immediately into me playing with his asshole, anytime I put a little pressure his cock twitched and a bead of precum leaked out of him.

Taking a breath and deciding to take the plunge and pushed my index finger slowly into his waiting hole. As soon as I broke into him Kyle let out a persistent, low moan. “Yeah dude, go for it.”

I worked my single finger in slowly until it was all the way inside, probing lightly until I found the small knot of flesh I was looking for and applied pressure while gently working it over. Kyle immediately grabbed the bedspread with both hands and inhaled deeply. “Don’t know what the fuck you’re doing but please don’t stop!”

I grinned back at him. “Dude I just started, don’t worry I’m not stopping anytime soon.”

I pulled my finger out and quickly lubed a second before working that into him, cautiously to not cause him pain. It wasn’t long before I picked up where I had left off, using both fingers to work his prostate and beginning to spread them to loosen his hole for my cock to fit in. Kyle responded to my work with a series of grunts and low groans, obviously enjoying my efforts. His cock remained rock hard, lying on his stomach and emitting a steady stream of precum onto his abs.

Considering that only one of my hands was busy at the moment, I decided to check out the other equipment while I had the chance. Taking the initiative, I wrapped my other hand around his cock and gave it a couple of strokes. The thing was heavy and hot, I could feel his pulse strongly in his cock as I played the loose foreskin over the length of him.

I kept up this way for a bit, one hand buried deep inside my best friend and the other stroking his massive cock, my own dick immeasurably hard and sticking straight out in between my legs. Gauging the time was right, I repositioned a bit and pulled my two fingers out of him to add a third. This time I really wanted to prep him for the main event so I began spreading them a bit while inside of him, something he seemed to like.

“Zach seriously, just go for it man. I’m so ready for that cock of yours!” Kyle raised his head to look down his body at me. “Go for it dude, I wanna see what that big thing of yours can do.”

At this point I wasn’t going to argue with the man so I pulled out of him and used a good bit of lube to prep my cock before positioning myself between his raised legs. Pressing my head against his entrance, I looked him full in the eyes. Grabbing on to one of his legs with one hand, I kept a slow, steady rhythm going on his cock with the other and began pressing into him.

Despite the prep work I’d done, his asshole was so very tight and felt amazing on my cock. As soon as my head entered, Kyle’s eyes rolled back in his head and he let out a deep moan that easily overtopped the cheap porn that still played on the tv. Keeping it slow, I started gently rocking forward, myself deeper into him a little at a time, trying to give him time to get used to me inside him.

“Yeah, just like that babe. Keep going!” The babe threw me off, even with my dick inside him it didn’t really click what we were doing until then. My heart leapt and I lost a bit of control, sinking my dick fully inside him in a spasmed thrust. “Of fuck yeah, do more of that! Don’t be a pussy!”

“Seriously calling me a pussy right now? Suck my balls dude.” The banter was easy, it was very much an us thing and I fell into with no effort.

“Sure, later though. Right now you’re supposed to be me!” Smirking down at him, I let go of his dick and grabbed his other leg, pulling both over my shoulders to get a better angle. Seeing the challenging look and shit eating grin he gave me in response, I grinned back before pulling almost completely out of him and slamming myself home, picking up a punishing rhythm, into him hard.

Immediately Kyle started a loud continuous moan, punctuating every thrust with a spike in volume to go along with the sound of my balls slapping against his ass.

“Dude, shut the fuck up! Everyone’s going to hear what’s going on in here if you don’t shut up.” But it seemed like the noise was uncontrollable for him, continuing with thrust into his tight, hot hole. Breaking for only a moment, I grabbed the boxers I had just discarded and forced them into his open mouth, muffling the noise that was issuing out of my best friend as a fucked deep into his guts.

Deciding to test how far I could push it, I redoubled my efforts to fuck Kyle’s brains out, slamming into him harder and harder, only to be met with louder moans from my cock impaling him. It wasn’t long before the weight of his legs and the position being slightly awkward caught up with me and I decided a change of pace was in order. “Here, I want to fuck you doggy. Flip over.”

Pulling out of him, Kyle nodded before crawling further up on the bed to make room and getting into position. His legs spread and his back arched with his ass in the air, he was an amazing sight. His large balls hung low between his legs with his massive cock visible and angry; his slightly gaping hole winking at me and waiting for my cock.

Kyle looked back at me and smiled, “You going to just stare at me or are you going to come fuck me?” Grinning, we wagged his ass at me invitingly, his cock and balls swaying back and forth.

Not having to be told twice, I jumped up on the bed and took my place behind him. Sinking my cock back in his hot hole, I grabbed his tight waist and picked up where I had left off, pounding into him incessantly. Having taken the boxers out of his mouth at some point, the loud constant moan started up again and this time I couldn’t care less. Let them know, I was having the fuck of my life and I didn’t care who knew.

This kept up for a couple of minutes, sweat beading down mine and Kyle’s bodies when suddenly Kyle’s moans started rising in pitch, getting more and more feral before his body seized up, his asshole tightening and spasming on my cock. I could hear the sound of jet after jet of cum firing out of his cock and onto the bedspread, the heavy splats evidence to the size of the load.

Knowing that he was cumming from my him and the suddenly tighter hold his hole had on me sent me over the edge, my balls tightening against me. “Dude I’m going to cum, I’m going to cum!”

“Cum in me dude!” With one final thrust I buried myself deep inside of him and emptied my balls into him. Pulse after pulse wracked me as I pumped my best friend full of cum, my orgasm seemed to last forever before I slowly came down off my high. Gingerly, I pulled out of Kyle’s ass, rolling to the side and on my back, my still mostly engorged cock laying across my stomach.

“Fuck that was amazing,” Kyle moved to lay beside me, doing his best to avoid the mess he made. “We absolutely have to do that again.”

“I’m game. As much as you want.” Closing my eyes, I started drifting off, Kyle wrapping himself around me.

The rest of the week in Cancun was a blast, Kyle spent absolutely no time chasing women for the rest of the trip, instead looking to me to drain his balls. It was only mildly awkward that next day when we met up with the other guys, everyone knowing something had happened but not wanting to broach the topic.

On the flight home, Kyle started rubbing my leg rhythmically and looked me in the eye. “You wanna join the mile high club.” I knew I was in trouble when his face lit up with a massive, mischievous grin. I never could tell this man no.

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