Oh, That’s Why
© Broken Boundaries Gay Erotica
Dinner that night felt like a showpiece meal. If I’d had pockets to keep my cellphone on me, I’d have taken pictures for Insta. Really, it was magazine-worthy. Lobster tails lay split open on gleaming platters, their shells slick with butter. Prime rib sat thick and pink at the center of the table, steam curling off each slice. Bowls of roasted vegetables, soft rolls, and potatoes big enough to feed an army covered the rest of the spread.
I served myself sparingly, even when my stomach growled. Connor’s earlier advice: “don’t eat too heavy,” still echoed in my head, and I didn’t want to risk ignoring him.
The conversation stayed light. They joked about whose wind surfing form was the worst and how Tyler had nearly dropped the speaker in the pool earlier. Tyler leaned back in his chair, twirling a glass of wine lazily. “Man, I could live like this,” he sighed.
“Your dad could probably make that happen,” Bryson said, cutting into his steak with a smirk.
Tyler laughed, shaking his head like he’d heard it all before. “Yeah, right. He’d just tell me to get a job.”
Everyone chuckled. I doubted any of their parents would really force them to work for their vacations though. I smiled too, even if my mind wandered. Connor sat at the head of the table, steady and unreadable. He contributed here and there but mostly listened, hands folded loosely around his glass. I still couldn’t get over how attractive he’d become over the last year. Not that he hadn’t been a stunner before, but the one year had done wonders for him.
Grant and Aiden mapped out an early-morning surf session. “The waves should be perfect tomorrow,” Grant said, almost glowing at the thought.
Aiden groaned quietly. “Perfect waves aren’t worth waking up before sunrise, but fine, I’m in.”
The normalcy of it all made me wonder if I was overthinking everything. Maybe Connor’s warning about dinner really was just that: a warning not to overeat. Still, I kept my plate light and my nerves heavier than I wanted to admit.
By the time the last plates were cleared, Connor pushed back his chair and stretched, his posture loose, his voice casual. “Why don’t we head down to the cabanas? Drinks. Music. Chill for a bit.”
“Finally,” Tyler said, leaping up like he’d been waiting all evening. “I’ve got the perfect sunset playlist.”
Everyone stood. Bottles and glasses were scooped up from the table. I rose last, falling in step as we made our way down the stone path toward the beach.
The cabanas sat close to the water, curtains swaying in the salt breeze. The sky was a wash of gold and pink melting into violet. Tyler set the speaker down and hit play. Soft music floated into the air, mellow, almost lazy. A calm ease settled over us.
The guys collapsed into the low chairs as if they’d spent the day working as opposed to chilling and partying. Connor lounged back, legs stretched, looking completely at ease. Bryson and Grant rummaged through a cooler for drinks, passing bottles around, glass clinking against glass.
I hesitated for a second before dropping into a chair between Grant and Aiden. Tyler glanced over the cabana, nodded at his speaker like he was proud of it, and grinned. “This is the vibe. I could stay here forever.”
Bryson laughed. “You’ve been saying that since we got off the plane.”
Tyler smirked but didn’t bother to respond. He leaned back, eyes half-lidded, soaking up the last of the light.
Grant handed me a bottle. I took a long sip; it was cold, crisp and tasted expensive like everything else here. The ocean breeze tugged lightly at my hair, carrying a clean, ocean scent, and for a moment it almost felt like any other night with friends.
Grant looked over. “You good, Tommy?”
“Yeah,” I said, nodding. “Just taking it all in.”
“Can’t blame you,” he said with a quiet smile before turning back to the water.
For a while, no one spoke. Music hummed from the speaker, waves lapped softly at the shore, and the air felt so calm I almost forgot why my stomach had been knotted all evening.
Eventually, Tyler got up to tweak the speaker. He strolled past me, and as he did, his hand came down in a quick, playful slap across my ass.
I jerked forward, more startled than hurt. “What was that for?” I laughed awkwardly, half turning toward him.
Tyler flashed me that familiar grin. “Just making sure you’re awake, Tommy.”
Aiden chuckled under his breath, shaking his head but saying nothing. The moment passed though my face stayed warm a little longer than I wanted it to.
The sun sank lower. The sky deepened from orange to purple, shadows stretching long across the sand. Connor set his empty bottle aside, the soft clink pulling every eye to him.
“Alright, Tommy,” he said, his voice calm but carrying weight. “Time for something big.”
My pulse stumbled. The unease I’d managed to tamp down all evening came rushing back.
Connor’s gaze didn’t waver. “Come here,” he said, nodding toward a thick log bench a few feet away. “Lie down on your stomach.”
I stood, every movement stiff and deliberate, and crossed to the bench. The others watched without a word. I lowered myself onto the log, my legs spreading naturally to either side, stomach pressing against the wood.
The second my body settled, I understood. The realization shot through me, hot and thrilling. My cock swelled instantly in its cage, pressing hard against the metal.
I turned my head slightly, catching Connor’s calm expression.
“Good,” he said quietly. “Just relax. We’ve got you.”
Relaxing felt impossible, but I nodded anyway. The thought hit me with full force: my first time wouldn’t be with one guy; it would be with all five. The excitement and the fear tangled together, impossible to separate.
A chair creaked softly behind me. Tyler’s voice, low and amused, drifted over. “Damn, Tommy. You look like a natural in that position.”
Bryson laughed breathily. “He’s not wrong.”
I felt like a pig on a roast, spread like that, my body burning with humiliation and desire. My skin prickled as I lay there, exposed, aware of every glance, every breath behind me.
Grant cleared his throat softly. “Take it easy on him,” he said, voice quieter than usual.
Connor didn’t look away from me. “We will.” He offered a faint smile. “Don’t worry, Tommy. This is going to be good.”
The ocean and the music seemed to fade, replaced by the heavy sound of my heartbeat. Footsteps approached. Bryson’s shadow fell over me.
He placed a hand on the small of my back, warm and steady. The touch sent an involuntary shiver up my spine. His hand lingered, rubbed lightly, and then lifted returning in a sharp smack against my ass.
I gasped, the sting jolting me. Bryson laughed quietly, pleased, and slapped me again, harder this time.
“Easy, Bryson,” Connor’s voice cut in, even and calm. “First time. Don’t get carried away.”
Bryson chuckled, his palm smoothing over the sting. “I know. Just warming him up.”
He nudged my legs further apart, opening me wider. The vulnerability was intense, the air against me cool and strange, but it only made my cock strain harder inside its cage.
Tyler’s voice broke in, “Hold up. We should probably give Tommy a little extra help.”
Bryson glanced back. “What do you mean?”
Tyler grinned. “We all spit on him first. Get him nice and ready.”
No one argued. Bryson moved around to face me, his cock already hard, veins standing out along the shaft.
“Open up, Tommy,” he said, tapping it lightly against my lips. “Get it wet for me.”
I obeyed. My mouth closed around him, tongue swirling over the head. He groaned, low in his throat, his fingers brushing my hair.
When he pulled out, slick with spit, he moved behind me again and spread me with both hands.
The first drop of spit hit my hole. Grant’s voice murmured close, “Relax, Tommy,” as his finger pressed the wetness in, slow and deliberate.
Aiden followed, his spit landing messier but just as warm. He pushed it inside with a slow drag of his finger. Tyler and Connor added theirs, each fingertip pushing past the rim, spreading me open, leaving me wet and trembling.
Bryson leaned over me last, his spit hitting dead center, his finger sliding in deeper than the others. A helpless sound slipped out of me.
“That’s it,” he murmured, moving into position. “Now you’re ready.”
I squeezed my eyes shut as the blunt head of his cock pressed against me.
He pushed forward. The pressure was relentless, my body clenching tight around the intrusion.
“Breathe, Tommy,” Connor said softly.
I tried. Bryson wasn’t patient, he shoved harder, and the head punched through.
I gasped, a sharp, involuntary sound. Pain flared hot, making every muscle seize.
“Slow,” Connor reminded him, a thread of command in his voice. “Let him adjust.”
Bryson stopped, panting, gripping my hips so tightly his fingers dug in. The pain ebbed to a deep ache, and after a few breaths, I managed a nod.
He took the signal and eased forward. Inch by inch, the ache grew more intense, stretching me wide, until his hips met me.
The fullness was all-encompassing, like every nerve in my body had been pulled into that single point.
“You good?” Bryson asked, voice tight.
“Yeah,” I managed.
He started to move. He drew back slowly, then pressed in again, testing. Each stroke dragged against me, every movement sharp and new. The pain dulled but didn’t vanish, mixing with an insistent twinge that felt almost good.
Bryson’s rhythm was clumsy, too careful one moment, too rough the next. It hurt, then it didn’t, then it hurt again but there was always pleasure too. Undeniable, unbelievable pleasure.
I clutched the log, breath coming in short bursts. The cage bit into me as I leaked helplessly inside it, a humiliating mix of frustration and arousal. If this had been any other first time, I’m sure I would have been furiously stroking my own cock, but truth was, I wasn’t that upset. This was kind of perfect.
“God, Tommy,” Bryson groaned, his voice rougher now. “You feel incredible.”
Heat rushed through me at the praise. I arched slightly, pushing back, asking for more even as it burned.
Bryson caught the cue. His thrusts grew more confident, harder. His hips slapped against me with a wet sound.
Without warning, his hand cracked across my ass. The sting made me jolt. Another slap followed, harder, the sound sharp in the quiet.
Laughter rippled softly from the others, but my embarrassment only spiked my arousal.
“You like that, Tommy?” Bryson teased, voice hungry.
I nodded quickly, face hot, not trusting my voice.
He gripped my hips tighter and drove into me harder, his rhythm steadier now, his breath ragged. The sting from the slaps mingled with the friction of his cock, every thrust pushing me closer to the edge of something I couldn’t reach.
“God, you’re tight,” he muttered, his voice fraying. “Fuck, I’m getting close.”
His pace faltered, then sped up, uneven, his body straining.
A final thrust buried him deep. Bryson groaned, long and raw, as he came, warmth flooding into me in hot, pulsing waves.
He stayed there for a few breaths, then slowly pulled out. Cum slipped from me immediately, wetting my thigh.
“Damn,” he muttered, breathing hard. “That was incredible.”
I stayed draped over the log, cheeks flushed, body trembling, knowing this wasn’t the end.
Bryson stepped aside, still catching his breath. The others shifted slightly, the quiet rustle of clothes and sand signaling their turn was coming.
Footsteps approached. Grant’s voice, softer than the rest, came from just behind me. “My turn, Tommy.”
His hand rested on my lower back — steady, warm. The difference was immediate. He wasn’t rushing.
“You’re doing great,” he said, his tone calm and reassuring. “Just breathe for me, okay?”
I nodded, breath shaky, as he lined himself up. Bryson’s cum made everything slick, the sensation strange and filthy and exciting.
Grant pressed forward carefully, inching in. His patience was different from Bryson’s clumsy eagerness, but no less thrilling.
“That’s it,” he murmured as I tried to relax, letting myself open to him. “You’re perfect, Tommy.”
A sensation I couldn't quite explain spread through my chest at the words, easing the tension in my shoulders. I closed my eyes and let the sound of the ocean and the steady pressure behind me blur together. That was cock one, I had four more to go.
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