Slut For Cabo – Part 5

Everyone in this story is 18+

Jake lay back against the pillows, his chest rising and falling, a faint sheen of sweat still on his skin. I stared down at him, still breathless from what he’d just done to me—my first orgasm with someone else, my body still tingling, brain floating somewhere just beneath the ceiling.

But I wanted to do something for him too.

“I, uh… I want to try,” I said softly, eyes flicking down to his cock, still hard, thick, glistening slightly from the condom he’d rolled on earlier.

Jake raised an eyebrow, then grinned. “Yeah?”

I nodded. “I’ve never… y’know. But I want to.”

He sat up a little, resting back on his elbows. “You don’t have to.”

“I want to,” I said again, firmer this time.

He didn’t argue.

I moved down between his legs, heart racing, hands awkward as I touched his thighs. Up close, his cock looked… big. Like, intimidatingly big. But I wrapped my hand around the base and leaned in, tongue flicking out for a tentative lick along the underside.

Jake let out a soft breath. “Take your time.”

That helped.

I licked again, slower this time, then let my lips slide over the head. The taste was strange but not bad. Just… different. I bobbed down a little, sucking gently, then back up. My teeth grazed him once—I flinched, mortified.

“Easy,” he said, chuckling. “Less jaw, more lips.”

“Sorry,” I muttered around him.

But I kept going, trying again. Slower. Smoother. My hand moved in time, stroking what I couldn’t fit, and I listened—to his breathing, the way his thighs tensed, the way he muttered quiet little curses under his breath when I did something right.

“God, Isaac,” he groaned. “You’re… actually really good at this.”

I pulled off for a second, panting. “You don’t have to lie.”

He laughed, then reached down and brushed his fingers through my hair. “I’m not. Enthusiasm counts for a lot.”

That made me smile. I leaned in again, sucking deeper this time, my head bobbing a little faster, hand still working the base.

Then he gently pushed me back, breath hitching. “Okay—stop. Stop, or I’m gonna cum.”

I blinked up at him, lips wet. “Isn’t that kind of the point?”

He smirked, pulled me up for a kiss, and whispered against my mouth, “Nah. I’ve got other plans for where I wanna finish. If that’s fine with you, of course?”

Was it going too far? Maybe. But I didn’t care.

“I want to try it. Anal.”

He grabbed the lube.

My heart slammed in my chest.

Jake looked at me. “This is your first time, right?”

I’d already been painfully honest up to this point, so I decided to just say it. “Yes.”

He gave me that knowing smirk again—the one he’d done a lot—like he could see right through me. “And you’re sure you want to lose your v-card like this? To a frat guy you just met, while not entirely sober, in Cabo?”

I didn’t hesitate. “Yeah, I want this. And I do know you... a little, Jake. Listen, I want to do this. And let’s face it—either I lose my virginity now, to you, or I lose it to some other frat guy who might not be as nice when I start college.”

Jake chuckled. “Fair enough. Just one more question. Do you want me to use a condom?”

Again, I responded without pause. “No. I want to feel it. To feel you. And… I assume you’re, like, healthy and stuff?”

Jake nodded. “Yeah. I mean, being in a gay frat? Let’s just say we’re all on PrEP and get tested a… lot.” He grinned.

I had no clue what PrEP even was, but I desperately wanted to get this show on the road. “Then get over here,” I said, patting the space beside me.

He crawled up next to me, still wearing the biggest grin in the world, and I was still coming down from my first-ever orgasm with someone else’s hands—or mouth—on me. Now, I was about to find out how it felt to have a dick inside my ass.

“You still good?” he asked.

“Yeah,” I breathed, eyes locked on him. “More than good.”

He lubed up quickly, his fingers slick, warm, and surprisingly gentle as he reached between my thighs. “Relax,” he murmured, leaning in to kiss me again, slower this time. “Let me take care of you.”

I nodded, biting my lip. I tried to relax, but the tension in my body was impossible to hide.

The first finger slid in, slowly. I gasped—part shock, part heat. It was intense, unfamiliar, but not bad. Just… new.

“Breathe, Isaac,” Jake said, voice low. “You're doing great.”

His finger moved slowly, curling slightly. Then another joined it, stretching me more. It burned a little, but the way he kissed me while doing it made the rest of the world feel far away.

“I’ve got you,” he whispered, and I believed him.

By the time the head of his cock pressed against me, I was flushed and panting, legs spread wide for him, and he paused, giving me one last chance to back out.

I didn’t.

“Please,” I said, barely above a whisper.

He pushed in—slow, steady—until just the head was in. I gasped, my whole body tightening, and he paused, giving me time to adjust. He leaned in, kissing me gently, his hands soft and reassuring as they roamed across my chest and sides.

“It’s okay,” he whispered. “Breathe.”

I did. Slowly. Letting my body settle, letting the shock turn into something else—deeper, heavier.

When I nodded, he moved again—pressing in further, inch by inch. The stretch burned, sharp at first, and I hissed through my teeth. My hands flew up to his shoulders, gripping tight, nails digging in just to hold on.

“Fuck, you’re tight,” he groaned. “You still okay?”

I nodded, teeth clenched. “Yeah. Just—keep going. I want it.”

That seemed to flip a switch in him.

He pushed in with a deep thrust, and we both moaned. The stretch was intense, bordering on too much, but it was also everything I knew I’d been craving.

He set a rhythm—slow at first, grinding deep with every roll of his hips. My body adjusted, the burn turning into pressure, then into something else entirely—something freaking wonderful.

“Jake—shit,” I moaned, bucking my hips up without even thinking.

He laughed softly, eyes wild with heat. “That’s it. Take it, baby.”

My whole body was moving with him now, every thrust making me gasp, the slapping of skin on skin echoing through the room.

“I can’t—It’s almost too good!” I started, but Jake leaned down and kissed me hard.

“You can. And you are.”

And I did.

Jake pulled back, still buried deep inside me, his body glistening with sweat under the soft light of the hotel room. His hands gripped my thighs as he slowed his rhythm just enough to breathe.

“Let’s switch it up,” he said, voice rough and low.

I blinked up at him, dazed. “What?”

He smirked. “On top of me. Trust me.”

I nodded, heart hammering, and scrambled to get on top of him. My limbs felt loose, like I was floating, barely in control even as I was on top of him. I felt Jake’s hands on my hips, lifting me slightly, pulling my ass up just enough. Then he pushed back inside, deeper this time—different angle, fuller, sharper.

I gasped into the pillow, eyes wide.

“Yeah, you feel that?” he grunted, hips snapping against me, the rhythm faster now, more intense. “Fucking perfect.”

All I could do was moan, the pleasure building like a wave I couldn’t stop. Every thrust hit a spot inside me that made my whole body light up. My cock throbbed beneath me, untouched, leaking onto his abs.

Jake’s pace grew frantic, his hands gripping tighter, his breath rough in my ear. “You gonna cum for me again?” he growled.

I couldn’t even speak. Just nodded, gasping, completely lost in the heat of it.

He grabbed my cock, jerking me hard and fast while still pounding into me from below. That was it. My body tensed, my back arched, and I came again—hard—groaning into the air as my vision went white. And speaking of white… yeah, his abs and chest were coated in it.

“Fuck, Isaac—” Jake choked out under me.

Jake picked up the pace, his thrusts growing frantic, but somehow still controlled—still careful. Each movement was rougher, deeper, but never careless. I felt his cock swell inside me, stretching me more, pressing hard against something deep that made my whole body twitch.

His breathing turned ragged. His moans louder, deeper. I could feel the heat building between us—his need, his focus. He was close. And I wanted it. I wanted him to finish inside me.

He slammed into me one last time—deep and hard—and then I felt it: the sudden tremble in his thighs, the tightness in his grip on my hips, and the sharp, desperate sound of his voice as he groaned my name through clenched teeth.

His cock twitched deep inside me, thick and unrelenting, and I felt him let go—warmth filling into me as his whole body tensed under mine. He held me close as he came, and I reached down to kiss him as he kissed me back.

And I just lay there, breathless, overwhelmed, full.

For a long moment, there was only our breathing—ragged, heavy, in sync.

“Holy shit,” I finally managed to say into the pillow.

Jake laughed softly, and whispered, “Good call, we didn’t need to split the beds.”

I eventually rolled off, flopping onto my back beside him with a satisfied sigh. My whole body felt like warm jelly—numb, tingly, wrecked in the best way possible. I stared up at the ceiling, trying to catch my breath, still unsure if any of that had really just happened.

He turned his head toward me, hair slightly damp with sweat, grin still plastered across his face. “You good?”

I nodded, dazed. “Yeah. That was... more than good.”

He chuckled. “Glad to hear it.”

There was a short pause, just the sound of the ceiling fan whirring overhead and the occasional shout from drunk spring breakers echoing down the street below.

Then he said, “Okay, so... I gotta admit something.”

I turned to look at him. “What?”

“The hotel room key?” he said, rubbing the back of his neck sheepishly. “Yeah, that would’ve actually been free to replace.”

I blinked. “Wait, what?”

He shrugged, biting back a grin. “I was kinda hoping you’d invite me over. Figured a little white lie wouldn’t hurt.”

I stared at him for a beat—then burst out laughing. “You manipulative bastard.”

“Hey,” he said, holding his hands up, “worked, didn’t it?”

I shook my head, still laughing. “Yeah. And honestly? I’m glad you told it.”

He grinned, and something in the way he looked at me then—easy, unguarded—made my chest feel weirdly full.