Surf and Swallow
© Broken Boundaries Gay Erotica
Aiden and I caught up to the others on the beach just past the paddleboard hut. The afternoon sun had climbed higher, casting hard shadows across the white sand. A couple of sails were already set up near the waterline, flapping lazily in the wind. The boards were stacked in twos and threes beside a folding table with life jackets and waterproof bags. Grant and Bryson were poking around the equipment while Connor and Tyler watched from a log nearby.
“Well?” Bryson called out as we approached. “Did he drain the main vein?”
I rolled my eyes.
“Don’t be shy,” Grant added. “We saw you walking off with him. Pretty intimate.”
Aiden didn’t miss a beat. “Tommy had a very hydrating experience.”
“Fuck off,” I muttered under my breath.
“You looked like you were enjoying it,” Aiden said quietly, grinning as he stepped past me toward the gear.
I ignored the flutter in my stomach and tried to act normal. The piss had washed off in the outdoor shower by the hut, but the mental residue clung to me. I still felt slightly stunned from the whole thing, my skin too aware of the breeze, the sun, my cage.
“Boards are sick,” Tyler said, stepping up to the stack. “They’ve got the straps already set. Should be easy to figure out.”
I nodded, pretending to pay attention. Honestly, I was hoping we’d just mess around with the gear and no one would notice me too much.
Grant glanced at his phone. “Should be here any minute.”
“Who?” I asked.
“The hotel guy. They send someone to do the lesson.”
My chest tightened. “There’s a… lesson?”
“Yeah. You didn’t think they were gonna let us wreck ourselves with no instruction, did you?”
I didn’t answer. My mind was already spinning. They hadn’t said anything about staff being involved. I looked toward the resort, half expecting to see that leathery old manager with the bad comb-over trudging across the sand in flip-flops.
A knot formed in my stomach. I turned to Aiden. “Do you think I could… like… wear something for this?”
He tilted his head. “Why?”
“There’s going to be a staff member here. A stranger. I’m already—”
“Nah,” Bryson said, cutting in. “You’re good.”
“But—”
Connor looked over. “They know about you.”
“They what?”
“Yeah,” Grant added. “We told them when we booked the trip. Explained your situation.”
“My situation,” I repeated.
Aiden gave my shoulder a squeeze. “They’re chill. I promise.”
I looked down at myself—bare except for the cage, my skin already warm from the sun. The idea of being seen like this by someone not in the group made my stomach twist. I swallowed hard and kept still, hoping whoever showed up wouldn’t make it worse. Though somehow, I already knew it would be.
I spotted him first.
He was coming down the path from the hotel, a board under one arm and a mesh bag slung over his shoulder. Not the old manager. Not even close.
He looked around twenty-eight or twenty-nine, tall and broad-shouldered with a deep tan and lean muscle packed into a tight sleeveless rash guard. His brown hair was thick and cut in a textured push-up crop, styled like he’d run his fingers through it with some gel. It made his whole face look boyish and casual, even though his body was absolutely grown. His board shorts rode low on his hips, and when he waved, I noticed how defined his arms were, veins running down to his wrists.
“Hey guys,” he said as he reached us. His voice was warm, friendly, and totally unaffected by the fact I was standing there naked and caged.
“Ready to get started?”
The others all nodded or greeted him. No one introduced me.
I stood there awkwardly, trying not to fidget, though every instinct screamed at me to cover myself. The instructor gave a quick glance across the group, taking us in, then set his board down and unhooked the bag.
“Name’s Shane. I’m the water sports instructor for the week. We’ll go through a basic paddle session, then move to windsurfing once you’ve got your footing. Should be fun.”
He didn’t even blink at me.
I felt the blood rushing to my face, my entire body reacting to the quiet acknowledgment of nothing. Like I wasn’t even unusual.
Shane picked up a paddleboard and turned it around. “Anyone surf before? Paddle or wind?”
“Connor did sailing camp in sixth grade,” Tyler offered. “But I think he spent most of his time there owning the basketball courts.”
“Hey,” Connor said. “It was seventh grade.”
Shane chuckled. “Alright. So probably a good idea to start from the top.”
As he began explaining how to balance on the board and shift your weight, I tried to stay focused. But I kept catching his eyes drifting across the group, and I couldn’t tell if he was checking everyone out or just cataloging his class. When they landed on me, they didn’t linger. But they didn’t avoid either.
He kept his tone professional. Relaxed. Normal. Clearly the staff had been prepped for this.
If he’d looked shocked, I could’ve sunk into the sand. If he’d made a face or asked a question, at least I could’ve reacted. But his calm, breezy attitude just highlighted how intentional this was. How planned. How expected.
The old hotel manager might have been better. At least I didn’t consider him a peer.
The old manager didn’t turn me on either.
I swallowed hard and tried to keep my face neutral.
Shane tossed a few boards down in a row and waved us forward. “Grab one and we’ll start with some dry runs on the sand.”
I bent down to lift one, aware of how my ass was fully exposed, my cage swinging slightly as I moved. Was he was watching? My hole completely exposed for him to check out if he wanted to.
I felt humiliated in an entirely new way, which didn’t seem possible after everything I’d experienced this week, but here I was.
I kept my eyes on my board, pretending not to hear.
Shane glanced over, brows briefly pinched. “He’ll be fine,” he said evenly. Then back to the demonstration. “Most important thing is keeping your core engaged and looking ahead, not down.”
Bryson backed off, but I could already tell this was going to be one of those sessions.
We spent a few more minutes going through the motions. Shane stayed focused, correcting posture, adjusting foot placement, and walking calmly among us. His voice was steady, relaxed. If he noticed my nudity, he didn’t let on.
He moved toward me to adjust my stance, stepping beside my board. “Widen your base just a little. Here—” His hand brushed the side of my knee to guide it outward.
I twitched slightly at the touch, not because it hurt, but because of the way it jolted through me. Just casual contact, but it made the cage shift slightly between my legs, tightening the edges. I kept my expression still.
Shane stepped back. “That’s better. Keep your weight even, and you’ll be fine.”
“Unless the cage makes him top-heavy,” Tyler said, loud enough to carry this time.
Shane paused for half a second, then turned back to the group without comment.
We transitioned to paddle basics next. Shane handed each of us a paddle and showed us how to grip and rotate through the shoulders.
“Not just your arms,” he explained. “Use your whole torso. It’ll save you from getting exhausted too fast.”
I followed the motion, trying to mimic what he showed us. The paddle felt awkward in my hands, like I was holding it wrong even though I wasn’t.
“Maybe his grip’s off because he can’t jerk it anymore,” Bryson said.
Grant snorted.
I flushed, gripping the paddle tighter.
Shane glanced over, pausing mid-step. There was the briefest flicker of amusement in his eyes before he spoke again—casual, offhand, but not entirely innocent.
“Could be,” he said. “Good thing paddling’s low-impact. We’ll build him up slow.”
The boys cracked up. Even I let out a quick breath through my nose, caught between humiliation and surprise.
He didn’t lean into it. Didn’t wink or smirk or pile on. Just that one line—and then back to the lesson like nothing had happened. But the air had shifted. He wasn’t just tolerating the teasing anymore. He was joining the rhythm.
We followed Shane toward the edge of the water, boards under our arms. The ocean was calm, the tide curling in soft loops at our feet. The sun reflected off the water, turning everything around us bright and exposed.
I felt twice as naked out here.
“Start by kneeling,” Shane called, pointing toward the break. “You’ll stand once we’re past the chop.”
I dropped onto the board, knees sinking into the grip pad. My skin was already wet from the earlier splash, but the new position made everything worse. My ass was up. My cage hung down between my thighs. I knew what it looked like from behind, and so did everyone else.
“Do you recommend sunscreen for locked parts?” Bryson asked, adjusting his paddle like a microphone.
Shane didn’t respond at first. He kept paddling.
“Just wondering,” Bryson went on. “His whole dick’s out, and we’ve got UV seven today.”
“Could get a weird tan line,” Connor added.
That got a snort from Tyler. “He’s gonna need a dick koozie.”
Shane slowed slightly. “If he starts burning,” he said, “he should let me know.”
I stared at the back of his head, unsure if I wanted to laugh or sink under my board and never resurface.
We started paddling. My strokes were uneven, and every movement made the cage shift, pulling tight against my balls. I could feel myself swelling again. The friction. The motion. The attention.
“Tommy’s got drag,” Grant said. “Someone should check if his junk’s creating resistance.”
“It definitely is,” Connor said. “That thing’s like a reverse rudder.”
“Hey, Shane,” Bryson called. “Any safety tips for caged surfers?”
Shane turned back toward the group, still moving. “What kind of cage are we talking?”
“Small,” Connor said. “Tight. Stainless steel.”
Shane nodded, keeping his eyes on the horizon. “In that case... no belly flops.”
Laughter exploded around me. Even Grant lost it.
I looked down, trying to steady my hands on the paddle. My cock had pressed so hard against the front of the cage I could see the metal bowing slightly. It wasn’t built for ocean sports.
“Are those things waterproof?” Tyler asked.
“I mean, we rinse him off in the mornings,” Bryson said. “Seems to hold up.”
“Let me know if the saltwater starts stinging,” Shane said, tone still light.
“I will,” I muttered.
“You might want to hydrate more,” he added, now fully in rhythm. “Guys in steel tend to overheat.”
I felt like I was overheating. My chest, my cheeks, the base of my spine. Everything was flushed and tight and pulsing. The sun felt heavier now. Or maybe that was just my brain melting from embarrassment.
“Doing alright?” Shane asked over his shoulder.
I nodded quickly. “Yeah.”
“Cool. Let’s try standing.”
God help me.
Standing on the board was harder than I expected. My legs shook the first few times, and I nearly fell twice before getting my balance. But Shane was calm, patient, and clear. His instructions stayed focused. No more jokes. Just steady guidance.
The boys were scattered across the water now, paddling in lazy loops or deliberately bumping into each other. Aiden and Connor had already moved ahead, racing each other toward a buoy. Tyler was trying to kneel-paddle with one leg up like he thought it would look cool, but he kept tipping sideways. Bryson was doing circles around Grant, splashing him on every pass.
For the first time all day, I felt like I was just… part of it. Not a toy. Not a target. Just one of the guys, out on the water.
I kept my strokes steady, switching sides every few pulls. The breeze off the ocean felt good on my skin. The sun had warmed my shoulders, and even though I was still fully exposed, I felt a little less raw. I wasn’t sure if I was getting used to it, or if being active just made it easier to forget. The cage didn’t stop reminding me, though. It bounced gently with every shift of my stance, a dull constant pressure, like it was part of me now.
“Looking solid, Tommy,” Shane called from a few feet away. “You’ve got the best stance out here.”
I smiled before I could stop myself. “Thanks.”
“Don’t let it go to your head,” Connor shouted. “He’s only saying that so you don’t cry.”
“Shut up,” I said, but even I was laughing a little.
We rotated back toward shore, boards gliding in easy arcs. Shane demonstrated how to pivot using the paddle and angle the nose into the wind. I tried it and nearly flipped but recovered just in time. The rush of it—the balance, the control—it felt weirdly good.
By the time we came back in, I didn’t want it to be over.
“Alright,” Shane said as we regrouped near the shallows. “Wanna switch to windsurfing?”
The boys cheered and started dragging their boards up the beach while Shane unhooked a couple of sails from the rack. The wind had picked up, enough to catch the edge of the fabric and make it snap loudly as he unfurled it.
Grant stepped beside me as we waited our turn.
“You looked good out there,” he said.
I gave him a look. “Yeah?”
“Dead serious,” he said. “Could see your whole cage working hard.”
I rolled my eyes. But part of me liked hearing that. Too much, probably.
Windsurfing was harder to get the hang of. There was more movement, more chance of slipping, but I pushed through. Every time I reached up to adjust the sail or shift my stance, I could feel my whole body exposed in ways I couldn’t control. My legs were spread wide, the board wobbly beneath me, my ass fully out, and the cage jutting forward like some humiliating badge. The boys shouted and joked across the water, their voices drifting over the waves. I couldn’t hear all of it, but I didn’t need to. I already knew I was the punchline.
It was worse knowing Shane was still there. Not teasing, not staring, just watching. Focused. Quiet. Professional. Like he saw everything and filed it away without a reaction. My naked body. My cage. The way I kept trying to keep up like nothing was wrong. That should have made it harder. It should have made me want to curl up and die. And maybe part of me did.
But another part of me, some messed-up piece I didn’t want to admit existed, didn’t mind. Not really. I didn’t like being embarrassed. But I liked being noticed. Even by someone like him. Even when I wasn’t supposed to be.
I wasn’t trying to show off. I wasn’t trying to be sexy. But I was still hard in the cage, and I couldn’t pretend I didn’t feel that heat buzzing under my skin. Not anymore.
God. I was turning into a total slut.
The sun was dipping low as we dragged the boards back up the beach. My legs were sore, my arms felt like rubber, and my skin was tight from salt and wind. Shane gave us a short nod as he packed the last of the gear, then headed off without another word. No fanfare. Just gone.
As soon as he was out of earshot, everything changed.
Grant stopped in the sand and looked straight at me. “Alright,” he said, brushing his wet hair back. “Tommy’s already had two luxury meals today. I haven’t even had one blowjob.”
I blinked.
“I mean,” he went on, looking at the others, “seems kinda rude, right? Everyone’s had theirs except me.”
That got some laughter from behind.
Connor grinned. “He’s got a point.”
“I’m not waiting until after dinner,” Grant said. Then his eyes cut back to me. “On your knees.”
There was no room to hesitate. I dropped instantly, the warm sand pressing into my shins as I looked up at him.
Grant didn’t tease. He didn’t build it up. He just reached into the waistband of his swim shorts and pulled out his cock.
It was already hard—seven inches, thick and smooth, flushed a deep pink at the head. I couldn’t help staring for a second. It looked perfect. Better than most porn stars. Better than anyone I’d seen in real life.
Then he grabbed my hair and yanked me forward.
No warning. Just cock in my mouth.
The others whooped behind me.
“Damn,” Bryson said. “Grant’s not fucking around.”
“Tommy better be ready,” Tyler added. “That’s the prettiest dick he’s had in him all week.”
I sucked him fast, trying to match the pace he set. His hand stayed firm in my hair, guiding but not forcing. At first. My tongue moved under him, tracing the bottom of his shaft as I worked him deeper. I could already feel the spit building, strings of it slipping down my chin as I took him in again and again.
Grant let out a low breath. Then he started thrusting.
Not wild. Just steady. Deep. Possessive.
My throat tightened around him. I gagged once, and the sound made the others laugh louder.
“Fuck,” Connor said. “That’s hot.”
I blinked up at Grant. His face was calm, focused. He didn’t say a word. Just held me there and fucked my mouth like it belonged to him.
And I let him.
The cage was painfully tight now. My dick pulsed uselessly inside it, every nerve lit up, every muscle taut. I couldn’t even shift. I just stayed there on my knees, lips stretched, eyes watering, letting him take what he wanted while the rest of them watched.
Some part of me still felt humiliated.
The rest of me didn’t care.
Grant adjusted his stance and pulled me tighter, his cock pressing deep into my throat. I gagged again, harder this time, and he didn’t let up. His grip in my hair was firmer now, less guiding and more controlling. My hands instinctively came up to brace against his thighs, not to push away, just to steady myself.
“Getting messy already,” Bryson said, circling behind me. “What a shock.”
“I give it another minute before he starts drooling,” Connor added.
I was already drooling. I could feel the saliva spilling down my chin, strings of it dripping from my lips to the base of Grant’s shaft. My nose was buried against the soft skin of his lower stomach. I couldn’t breathe unless he let me.
He didn’t.
Not at first.
He held me there, deep, just long enough to make my lungs burn before pulling back and letting me suck in air. I coughed once, eyes watering, but then he shoved back in with a low grunt, and my throat opened again on instinct.
I wasn’t even trying to show off. It wasn’t performance. I just wanted to do it right. I wanted to take it. All of it.
“You’re lucky he’s into this,” Tyler said. “I’d have puked by now.”
“He is into it,” Grant said calmly. “You can feel it in his throat.”
That made them all groan in amusement.
“God, that’s disgusting,” Bryson laughed. “Hot, though.”
I moaned softly around him, not even meaning to.
“See?” Grant said. “He likes it.”
I did. Not in the way I liked ice cream or being told I looked cute. This was different. It was heat and shame and something thick in my chest that made it hard to think. The cage was so tight I could feel every twitch, every helpless throb. My knees were starting to ache, but I didn’t shift. I didn’t want to mess anything up.
“Slap his face with it,” Connor said. “Just for fun.”
Grant pulled out abruptly, his cock slick with spit. He slapped it once against my cheek—light, but loud. I flinched, then looked up at him, eyes glassy. His cock twitched, and he guided it back to my mouth.
I opened wide.
The head slipped past my lips again. Then the shaft. Then his hips were moving, a steady rhythm that built with each thrust.
“Fuck,” he muttered. “He’s actually good at this.”
I felt a flicker of pride. Then more drool.
I was a mess. My hair stuck to my forehead. My chin was shiny with spit. My breath came in short bursts whenever he let me have it.
And they were still watching. Still commenting. Still laughing like this was all just part of the afternoon schedule. Like using my mouth was no different than windsurfing or volleyball or breakfast. I wasn’t a novelty anymore. It was expected.
And I couldn’t stop shaking.
Grant was breathing harder now. His thrusts had lost their rhythm, growing shorter and sharper, hips jerking with a kind of urgency I hadn’t felt from him earlier. His cock pulsed on my tongue, swollen and slick, every motion making my jaw ache.
“Fuck, he’s close,” Connor said, leaning forward.
“You better swallow,” Bryson warned.
Grant didn’t say anything. Just grunted softly and shoved deeper. His grip on my hair tightened. My nose mashed against his skin again, and I held still, swallowing down the gag as he stayed there, full length in my mouth, almost vibrating.
Then he pulled back. Not all the way. Just enough to start again. Fewer strokes this time. Just enough to push me to the edge with him.
“Tongue up,” he muttered, voice low.
I obeyed, flattening it beneath his shaft, letting it cradle him. My jaw ached. My throat felt stretched and raw. My knees were numb. But I didn’t stop.
I couldn’t.
He shoved forward one last time and groaned, his cock pulsing once—then again—then again.
Warmth flooded the back of my mouth.
He stayed deep, holding me there while he emptied everything down my throat. My eyes fluttered shut. I swallowed around him, gagged once, then swallowed again. It felt endless. Hot and thick and overwhelming. Some of it slipped out the side of my mouth and ran down my chin.
“God damn,” Tyler muttered behind me. “That’s how you finish a surf lesson.”
Grant finally exhaled and pulled out. His cock twitched once as it slipped free, a single strand of cum still clinging to the head. It dripped onto the corner of my lip.
I stayed where I was. Mouth open. Chest heaving. Knees buried in the sand.
“Look at that,” Bryson said. “Still kneeling. That’s manners.”
Grant tucked himself back into his shorts, brushing a hand through his hair like he’d just wrapped up a workout. “He’s learning.”
I didn’t say anything. Couldn’t. My mouth tasted like him. My chin was sticky. My cage was screaming. I looked up and saw all of them still watching me like it was normal.
And maybe it was now.
I’d just blown a guy on the beach with five friends watching, and I wasn’t even sure when the line had been crossed—only that it had.
I licked the corner of my mouth instinctively.
There was still cum on my lip.
Grant stepped away, stretching his arms like he’d just finished a set at the gym. The others didn’t say much now. A few exchanged grins. Tyler was already heading toward the board racks, brushing sand off his legs.
I stayed kneeling a moment longer, catching my breath. My lips were swollen, my knees were stiff, and my throat was sore. I wiped my chin with the back of my hand but didn’t get all of it. I could still taste him.
No one told me to get up. Eventually I just did.
The breeze was cooler now. The sun had dropped closer to the horizon, casting long shadows up the sand. The light had that golden-hour glow the influencers always talked about. I felt anything but photogenic.
We started walking back toward the path that led to the main resort buildings. I was a step behind them, not bothering to catch up. My whole body felt raw and tired in a way that wasn’t physical. Just drained. Used.
Grant looked over his shoulder once and squinted.
“You’ve got some left on your mouth,” he said, casual like he was pointing out dirt. “Might wanna wipe.”
I did; how fucking embarrassing.
He laughed. “No worries. It was a big load.”
The others chuckled.
We passed the rinse station and cleaned the salt water off ourselves before hitting the paved path again. We all grabbed towels the staff had left nearby earlier and started drying off. Bryson slapped Tyler with his own and got a yelp in return. It was already like the blowjob hadn’t happened. Like it had been just another part of the day’s itinerary.
When we reached the doors to the dining hall, the sound of the ocean faded and the conversation died out.
Connor turned around just before we went in and looked at me, smirking.
“Don’t eat too much tonight,” he said. “Or anything too heavy.”
I blinked. “Why not?”
The others burst out laughing. Not cruel, just loud.
Tyler clapped a hand on my back. “You’ll see.”
The doors swung open, and they walked in like nothing was unusual. I stood there for a second, still naked, still locked, still covered in the fading evidence of what I’d just done. The air-conditioning hit my skin and made me shiver.
I followed them in.
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