Urban Sex Vacation

I use hook-up apps as a way to travel I suppose. I don't have the luxury to flit about the globe taking selfies with landmarks, so more often than not, when I get to chat up a guy, I'm dipping my toe into a completely different life. To a degree, if and when we hook up, I become a different, more adventurous guy. And perhaps, ashamedly - when I'll leave town, there's no looking back.

There was one time though, that my travel actually took me somewhere other than a bland condo lobby.

One particular night, I had a taste for older men, a real 'daddy' type. I was 32 and well out of my twink phase; still fit and trim, but couldn't be bothered shaving or waxing anymore. Average height, average build, average look - I cut my hair in a floppy hipster style, wore thick framed glasses, and often passed for straight. Beneath the flannel, I had a circumcised penis that hung around 7", and a hairless ass that could still fill out a pair of khakis. In a few years, I might be the one a younger guy is calling 'daddy', but for now - I wanted to be the one on his knees for an older man.

I had been at work late, and was walking along down by the waterfront perusing the apps when such guy messaged me. His name was Bert.

Bert was a former ballet dancer, and current instructor, who rarely stayed in the same city for too long. He was handsome and well muscled for someone in his early fifties, probably in better physical shape than I was. He had a big wide chest, his pectoral muscles barely showing a sag. The front of his torso was covered in a thick salt and pepper rug of fur. I salivated, thinking about what lay below.

I noticed our proximity, and sat down on a nearby bench, hoping to not lose my chance at play. Old couples and kids straggled by as we exchanged our sexual interests and histories. I was in. Bert was just the guy I wanted right then. So I asked him for his location.

- I've got a place on the island -

I looked up from my phone and over the water to the island. The sun was lowering in the west, and I got an electric jolt in my brain that said, 'you have to do this'.

The island in question was no more than a 10min ferry ride away. It had a little children's amusement park in the middle, a small community of houses at one end, and some great beaches. Most importantly, was the Hanlan's point beach, a clothing optional stretch along the west side that had a reputation for being pretty 'cruisy'. It was always packed on the weekends, and I tended to avoid the crowds - but I wondered what it was like after dark, when the last of the visitors raced to the final ferry, and the island emptied of all but the residents.

I texted Bert back, and he told me where to meet him once I got off the ferry. Looking around the lake, I noticed that a ferry was just about to dock, so I dashed over to the terminal to buy a ticket and run onboard. One of the captains shouted out the final schedule for the evening as we steamed towards island.

Disembarking, I saw Bert off to the side waving and smiling. He wore a simple peach tank top, faded blue shorts and flip flops. He looked just like his picture, but in person seemed taller. The hair on his chest and legs and arms was thick, and I felt it brush the back of my neck as he put his arm around me. I grew uncomfortably hard in my pants as we walked, and I realized that I had put myself completely in the hands of this strong and handsome, older stranger.

I can't even remember what we talked about as we walked down the path, I just kept smiling and nodding, staring at Bert's strong face in the twilight. At one point, he pulled me in close, into his side, and I could smell the natural smell of an unwashed man. I was beside myself with desire. Bert guided me off the concrete walk and through a dirt path amongst the trees. Even in the dark, I could see the odd shadowy figure here and there. My heart raced. As we stepped out of the wilderness, I felt the loose sand underfoot. We were at the beach.

The last gasps of the sun reflected on the water, and I squinted to see the stars. Bert's hand wandered down to my ass, slipping into the waistband of my work khakis. As we walked, we passed people who were heading to the last ferry, exchanging glances. Bert nodded at one or two, obviously a regular. At a certain point, Bert took his hand out and stopped. He raised the tank top over his head, giving me a glimpse of his full, hairy torso. Holding the shirt in his hand, he hooked his thumbs into the waistband of his shorts and pulled them to the ground. Stepping out of his shorts, and standing straight up, I was finally able to see the gorgeous, uncut monster he had been hiding this entire time. He smiled at me and kept walking.

"If I were you kid, I would be feeling mighty overdressed about now," He called back over his shoulder.

I stood there a bit stunned. I knew where this was all going, but I had reached the point in my fantasy projection where the rubber met the road. Bert turned to me, grinning, with his arms folded and his cock calling to me. I began to unbutton my shirt.

Slowly, my meagre chest hair came into view, and my nipples felt the cooling air. I dropped my shirt onto the ground, along with my bag and started to unbuckle my pants. Stupidly, I forgot to take off my shoes, and I nearly fell trying to struggle with everything. Soon though, I stood there in nothing but my underwear - a pair of black American Apparel briefs with white trim. They barely contained my erection. Following Bert's lead, I hooked my thumb into the waistband and dropped them to the sand.

I stood naked and erect, looking at Bert for approval. He clapped his big hands, and started to sprint to the water.

"C'mon! Let's go swimming!"

Caught off guard, I took up a jog and dashed into the water after him. It was cold at first, but warmed the deeper I got in. I looked around and tried to find Bert, but couldn't find him. Just then a body swam between my legs and shot me upright out of the water. I flopped and splashed, listening to Bert's deep laugh.

As I steadied myself, water just at my chest, Bert swam towards me, grabbing my body and pulling me to his lips. I was enveloped by this strong, hairy, muscular man. His tongue felt rough in my mouth, and I moaned as our cocks mingled under water. I instinctively wrapped my legs around his waist as we continued to make out. His hands massaged my ass, spreading them, kneading them. I felt like I had completely given over to him. I resisted the urge to call him 'daddy'.

We swam apart, and began to grab at each others cocks under water. He goosed me good one time, before walking up out of the shore. I followed him back out, and plopped down on the ground where he sat. With no towels, it was nothing but sand beneath us. At this point, our cocks had deflated in the cold. We just sat there like two guys, enjoying the night.

Bert talked more about his work, and his travel - which did kind of make me sad about my boring life. I was reminded that I was just a tourist in his world, living out my temporary fantasy. He asked me about where I had been, and I gave him a distracting response before we went silent. Looking back over at him, Bert leaned in and kissed me softly on the lips, lingering for what felt like minutes. His hand fell between my legs and grasped at my penis. Extricating himself from our kiss, he bent his neck down, and took me into his mouth.

Bert's technique involved a lot of suction at first, his hands tugged gently at my balls while he coaxed me to hardness. He slurped at my length, creating a lot of saliva, that he swirled around my knob, before plunging my length down his throat. It was a mixture of wild sensations that put me onto my back and had me writhing in the sand. Bert kneeled and parted my legs, pausing to spit onto a finger he stuck in my ass. I moaned and my hands went to my face, covering my eyes and mouth as I began to lose control. Bert expertly played my ass with his finger and he sucked the sperm from my cock. I exploded in his mouth, whimpering as he continued to pull the seed from balls, draining me.

Laying in the sand and grit, my 'daddy' covered me with his body and kissed me once more. I tasted my cum in his saliva, and sucked greedily at his tongue. He lay on top of me, warming me with his body until I was recovered, then grabbing my hand and running me into the tide to wash off. As we walked from the water, I turned and embraced him, kissing in the moonlight, wet bodies clasping together. The only difference was that while my cock was limp, his was at full mast. I groped him, and said:

"If only we had a condom,"

Bert looked down at my face, gently kissing my forehead. "We can fix that," he rasped out, taking my hand and dragging me towards the trees.

While still in bliss, my heart started beating a mile a minute, unsure of what was to happen next. As we disappeared into the brush, twigs and rocks stabbing into our bare feet, I began to hear strange noises. Soon, shadows began to fill in the blanks. While the beach was deserted, the forest was still full of men. In the dark, I could make out shapes bent over, kneeling, arms moving. The slurping and the slapping and the smell of bleach alongside the greenery gave away the trees full purpose. Bert approached a man even older than him who was jerking off while watching the other shadows, and whispered something in his ear. The man moved to a rock, and pulled out a condom from his discarded clothes. Bert thanked him and returned to me, his cock bobbing in front of him.

"Still up for this?" I swallowed, and nodded. He backed me over to a bit of a clearing, and sheathed his cock. "It's lubricated, but I'll take it slow,"

I braced myself against a tree, feeling him spread my cheeks and blindly press the tip of his cock around my puckered hole. He stopped to drop a gob of spit for added lubrication and slowly pushed inside of me.

The initial pain nearly blacked me out, and I began to sweat as his length began to fill my backside. I felt the brush of his public hair along my back and breathed a sigh of relief that I had taken him in. He stayed inside of me for a moment, then slowly withdrew. I felt the lubricant working in my favor, and calmed. His subsequent thrusts became easier, and more pleasurable to take. I shifted in place and with a new angle Bert found my prostate. I nearly tore the bark of the tree I had clung to, as my head became dazed, and I began a sustained cry. As Bert sped up, our slapping flesh gained us an audience, and when I opened my eyes, I saw half a dozen dimly lit figures stopping to watch and jerk off as I was being fucked in the ass.

I was the centre of attention. I had never been responsible for so much spunk being spilled in my life. The men around us quietly came in waves, as Bert fucked me against a tree. There was one last thrust before he slipped out of me, tearing the condom off and cumming in a single jet that painted my sweaty back. My ass was raw and empty, and I could feel my hole struggling to close. Bert lay across my back to kiss my ear, and whisper

"That was fucking hot, son,"

I stifled a giggle as I tried to get my legs back underneath me. Bert put an arm under me, and helped walk me back to where we left our stuff. We took another quick run out in the water to rinse off, and I could tell that Bert was genuinely being affectionate and cared for my well being. I was touched. When we came back onto the beach, and I went to gather my clothes he told me not to bother.

"My place isn't too far from here, nobody will see us,"

And so we gingerly walked along the lit paved pathway until we came to a little cottage. Bert walked me in, and offered to make me tea. I dropped all my belongings on the floor, and begged off, wanting badly to sleep. Nodding, he took me to a small room, and laid down with me, spooning his body into mine. I drifted off easily, forgetting where I was.

* * * * * *

The next morning, I awoke to the smell of coffee and bacon. Brushing sleep from my eyes, and realizing I was naked, I smiled a little. It hadn't been a dream or fantasy. I mean, my ass still hurt - so no, it all happened!

Bert stepped into the doorway with a big grin on his face.

"Morning kiddo,"

I looked over at his hairy, finely muscled frame, his uncut cock falling along his thigh. "Morning Pops,"

I lifted the sheet off my naked body and dropped to my knees in front of him, I pulled back his foreskin with my hand, and tasted his tip with my tongue. I struggled to swallow his girth, but slobbered and licked away like a starving man. He ran a hand through my hair as I worked his cock.

"So, does that mean you're going to be staying for awhile?"

I pulled his penis from my mouth, and thought about where I was in that moment. Seemingly a world away, but just a ferry ride apart from my normal life.

"Yeah, I like where I am right now."