You Wouldn't

A gay story: You Wouldn't “-So then he storms out of the bar expecting me to just run after him. But like, also I just KNOW that he’d be just as happy if I ignored him, because then he gets to accuse me of being mean and shit. UGH, like what do I do?!”

“Well, I-”

“It was a LOSE-LOSE situation right? Ughhh,” Jam took a breath before hot swapping a swig of his iced coffee for his vape. I realized he was on a monologue again, and slunk down in the cabin staring off at the waves. The ferry surged forward, as Jam cackled and resumed.

“So I pulled a maneuver on him, I got blitzed! Can’t be held responsible if I can’t hold my liquor!” Again Jam laughed too loud, causing other passengers to glare in our general direction. I pushed my sunglasses up along the bridge of my nose and cursed my life. Slowly we lurched to the dock, the water churning up around us and giving me a reprieve from Jamil’s braggadocio. We pushed to the front of the boat and ambled onto the path. Jam began another outrageous story as my mind began to drift.

I had been a 23 year old college student, newly out and utterly lost when I’d met Jamil at a bar. He had actually been the quieter part of a group I had gotten drug into, and it was a friend of his I ended up hooking up with that night. Our connection would come later as we bumped into one another on the apps. The conversation was gentle and flirtatious, and we chastely promised to wait a date or two before getting naked. In hindsight, I think the two of us were playing at a relationship, two young guys unsure of how to navigate their sexuality just crudely imitating a loving relationship so we could feel better about having sex. The whole thing lasted a month, and it was Jamil who pulled the trigger on the exit. With the safety of me as his quasi-boyfriend he quickly bloomed into an aggressive, sexually ravenous -in HIS words “homo-who-couldn’t-say-no-no” who just about exploded onto the scene. Comparatively I was still a shy, unassuming bottom still looking for my footing. Jamil was concise and polite, he cared but was no longer interested- thus starting the tumultuous relationship we’d developed ever since.

He was out there and I was left out, too keen to bask in any attention he would offer, and embittered about his continued absence in my life. He grew his friend circle to include an array of sexual adventurers who remained impenetrable to my meek desires. I kinda hated myself for accepting his invitation to day drink at the nude beach on the island; not simply for how pitifully empty my social card was, but because I’d hoped to maybe get a little playtime with my ex.

Jamil just kept bouncing from one story to the next, spilling all the tea about who had cheated on whom as we shuffled through the dunes and walked beyond the Clothing Optional signs. It was a Monday so the sand was sparsely populated. A large breasted young woman sat on a towel reading a book and eating fruit while a leathery old man stood at the edge of the water watching the horizon, his long tanned cock waving in the breeze. I started to entertain idea of going completely nude, an act that might shock my ex into making a move- but when Jamil stopped to declare the “perfect spot” I was dismayed. The further down the beach you went, the more daring a couple of guys could be, and here we were, stopped about 50 yards shy of the promised land. Jamil began to spread out the towels as I let out a quiet sigh and dropped my backpack.

Figuring I could work to show my intentions, I decided to make a show of stripping down to my speedo. I pulled open my belt and slowly unzipped, hoping to catch Jamil’s eye. He stayed kneeling and unaware as I hooked my thumbs into the sides of my shorts and slid them down. In my heart of hearts I was imagining him looking over and seeing my tropically printed bulge, being overcome with lust and uncharacteristically being the one to service me. Instead he glanced over as my shorts hit the ground, making eye contact and standing before pulling off his shirt. It was hard enough to maintain my composure with his hairy, dark brown tits out. A chest I had loved laying on and nuzzling my face into after sex- but when Jamil dropped trou, revealing he’d gone commando, and his cock uncoiled in the sun. I was about to lose my mind.

“Here, let me do you first” I nodded and looked off into the horizon as I raised my arms to the side and resigned myself to this torture. Jamil squirted a copious amount of sunscreen onto my back and began to smear the cream into my skin as he nakedly circled my body. There was part of me that wanted to tear off the speedo now, inviting him to “finish me off” but again, I wanted to maintain our friendship. Closing my eyes I could smell the coconut scent of the sunscreen as my body was covered. I could feel a brush of skin glancing across my thigh that I imagined was Jamil’s limp, long cock. I was feeling exposed but far too protected. I’d left my speedo on, but it was really the way my ex had made me a docile, neutered being in his presence that removed any sense of danger or adventure. Perhaps I’d even had a twinge of humiliation in allowing this naked man to order me into position so he could chastely apply sun screen to my sexless form.

“All done,”

I’d opened my eyes just as Jamil was tucking himself into a burgundy thong, fully cementing the platonic nature of our outing. He handed me the greasy bottle of SPF50 as I eyed the shaved trunk of his cock just visible from beneath the fabric. I lingered too long as the silence between us grew. If I had wanted to demonstrate to my ex just how sexually adventurous I’d become, gawking at his dick like a lovelorn loser was not the way to go about it. Nonetheless, I squirted a gob of cream into my hand and went about applying the sunscreen. It was a tough balancing act between appearing nonchalant, and enjoying the intimate act between us.

Greased and safe the two of us settled onto the towels, our eyes wordlessly grazing the beach for anyone worth a catty remark or flirtatious look. Seeing little to comment on, the two of us grumbled into some magazines and began to soak up the sun.

About an hour later, I’d been feeling the heat and laid back with my sunhat over my face. Possibly losing some time to a brief nap, I was jolted awake by Jamil’s laughter. Sitting up I immediately took note of the two twinks who had been flirting with him, and the all too familiar posture he had. He was preening, and seemed all too familiar with the young men. Introductions were made and I was largely ignored. I imagine that if I’d been more welcoming and open minded the two of us could have spent time with the two of them, but my immediate mood was defensive, as if these two were here to replace me and not enjoy US. Jamil could sense this, and as soon as the conversation provided an opportunity he had scrambled up onto his feet an excusing himself to go get a popsicle with his new buds.

“Just stay here sweetie, watch the stuff- do you mind? Do you want something? I’ll get you an Icee,” I had no retort and no right to cock block. We had agreed we were done, and It would have been immature and petty if I got all huffy and caused a scene. The anger and hurt built inside of me though as I sat on the ground.

On the other hand, It would be JUST the right amount of immature and petty if I dragged our stuff further down the beach and into the naughty area.

So I did just that.

I most likely looked like an idiot while I bunched up our towels and bags in my hands, and leaned south as I pulled up camp. Fuck that guy, I thought. When he comes back, I’m totally going to gaslight him. Why would I move everything we had? That would be stupid, this is totally where we were the entire time. Did YOU have FUN? Grumble, grumble, grumble. I rounded a leafy bush and dropped everything in a clearing. Surveying the pebbly beach, I realized my prospects at gaslighting Jamil about our location were about nil. Ugh. Fuck it. I muttered the words “fuck it” out loud to nobody in particular.

And yeah, nobody WAS around.

So I awkwardly pulled off my speedo and freed my average sized cock. Granted by that time, it had all compacted into a tiny handful of flesh and balls, so I dropped to my knees and reached for the sunscreen. Hey, you gotta protect everything right? I squirted some cream into my hand and began to pull at my cock, attempting to bring it to life. Yeah, fuck it. Who says I’m not adventurous? I’m naked on the beach jerking my cock. Fuck Jamil. I scooped up a glob of sunscreen with my free hand and reached behind me to stick a finger in my ass. This felt insanely good. Dangerous, daring, crazy. I imagined how Jamil would react if he came around that corner with his Icee and twink friends. Just watch me bitch!

Then I heard a rustle in the tall grass behind me, causing me to completely disengage and turn over on my back. My face burned red as I stared up at a stocky older man in a red T-shirt and hat. I’d been caught, oh fuck! What could I do?! It was only when a younger man, naked, stepped out from the bush that I felt at ease. He had caramel skin and rough looking braids with a long skinny hard on that made my mouth water. It was then that I spotted the older man’s cock loosely hanging out from the fly of his khaki shorts, and my brain began to fritz. I was splayed out before them, this pale young white kid with his pink cock and greased hole, looking shocked, horny and available; safely hidden from the rest of the beach. The way the two of them approached me made me feel like prey, and it must have broken something inside me, because I’d suddenly lost all hesitancy. I was on the ground, prone and wanting and it was incredible to feel all this crude lust aimed in my direction.

Braids was the quicker of the two, moving to kneel down beside me as I instinctively laid on my back. He leaned down for a quick kiss, as I was falling back, which made the intimacy quick. I suppose he sensed my submissiveness because his follow up was to slap my face with his thickening penis. The older man slowly stumbled to the ground, pushing my legs up before rolling back on his butt to pull his shorts off. It was all the antithesis of smooth, just a handful of mismatched bodies bumping and rolling together in the sand. Braids moved to straddle me so he could plunge his cock straight down my throat. I gurgled and gagged, starting to struggle back for the first time which just seemed to invigorate the men. I began to feel my first twinge of fear, but with the weight of Braids across my chest and the dull prodding by the older man at my back door, I was utterly helpless. Out of the corner of my eye I could see a short young man with shaven head dart around beside us, seemingly on the lookout as his eyes bounced from the pile of flesh to the beach. He too had his cock pulled out from his shorts and was jerking himself off as he moved about.

The old man eased open my hole with the head of his cock, greased with sunscreen. He pushed into me and I could feel my ass painfully stretching around him. Desperately wanting the pain to leave, I bore down and pushed against him. The moment he finally broke through, my eyes rolled into the back of my head, and Braids cock slipped out of my mouth. The gentle part was quickly played out though, as “daddy” began to fuck me in earnest. It still hurt a little, but the physicality of my body bouncing around combined with the prostrate stimulation had me moaning like a little bitch. Braids couldn’t safely get his cock back in my mouth so he settled for tea bagging me and letting me inhale his dirty, manly stench. He began to quietly hiss at me

“Fucking little cunt, out here just begging to me used aren’t you?”

“Mmm, hmmm. Oh, yeahhh. Mmmmm” I’d whine and mew at this new master as me slapped his cock against my forehead. My tongue would lap at the underside of his balls as the old man pulled my thighs to his chest and began to race towards the finish line. My entire body felt small and owned by someone else, all I could do was purr and cry. Braids pushed off my shoulders and sat on my stomach, leaning into my face and making me look him in the eye as he called me his “filthy bitch”. He spat at me, while angrily making eye contact, suddenly pushing me to a new masochistic level. My mouth hung agape as his gaze dared me to give it all up. The play had become an attack, and it was an attack that made me feel sexual in a way nobody else had. It gave me a kind of desirability I hadn’t craved before, a fulfillment I’d never realized existed. As much as I revelled in the submissiveness and humiliation, it was the idea that men could want me with such depravity, with such raw primal disgust that blew my fucking mind apart.

“Dad” began to shoot his load inside of me, and with every waning thrust I could feel his seed seep out onto the towel. Before I could consider feeling empty, Braids had scrambled to take his place, quickly jamming his dick inside me and beginning an assault. Two other men had happened across the scene -including the leathery guy from the beach. They stood beside the shifty guy, all with their dicks in hand. It was then that I was aware of my body. My cock- which would always shrink from anal- shamefully bounced around, my little belly jiggling. I was being taken sure, but I was also being seen. Any of these men would run into me on the street and remember me in this moment.

As I took an absolute pounding from braids, my arms shot down and I bunched the towel in my hands. The other men standing were at a loss at how to get involved before our lookout took a couple steps forward. At first all I could feel were a few dribbly little drops on the hollow of my ribs. Then a quick gush which caused me to open my eyes, before I felt the full stream. Our antsy little friend had calmed down long enough to piss on me, giving me yet another brand new experience to add to my repertoire. He had aimed poorly to begin with, splashing my torso before moving up to wash my face in piss. It smelled, and I bit my lips shut to prevent myself from tasting it, but the dirtbag just kept going. Had I been able to see, I would have noticed one of the other men let loose a stream of urine, choosing to spray my entire upper body with piss, all while Braids fucked me and cursed them out.

By the time the two of them were empty, the leathery guy had knelt down and shoved his erect penis in my face. I was a little confused and scared, because I didn’t want to drink piss, but I felt him jerking his cock over my lips and instinctively knew he was there to feed me. I opened my mouth, tasting the traces of my baptism, and caught the first volley of cum. Strings of white painted my face, and I blindly tried to suckle my provider to no avail. Before I could react, my body was pulled up and flipped around, Braids choosing to roughly reposition us. My face was pushed into the terrycloth then off into the sand as I was fucked with all abandon. Braids began to cum inside of me but pulled out and sent a streak of cum across my spine. Another cock took his place, and then another.

By the time the movement around me stopped and there were no more hands nor bodies, nor fucks to give I had collapsed flat onto the ground, half on the towel half off. I laid still like that, collecting my pains and my pleasures for what seemed like an eternity. Turning over onto my back I could feel the sun provoking an erection as I relished in my exposure and in my use. I reached down to touch myself and had a memory of Jamil.

We were in bed awhile back, and he had been quiet and gentle because he wanted to explain to me how we were just on two different paths. He called me many sweet things, and laid his hand on the middle of my chest.

“There’s just so many things I want to try that I would like to do, and I just think that you wouldn’t,”

Crawling to my feet, I gave the sodden towels a glance and walked into the water.

Wouldn’t what?

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