Back on Leo’s bed, Brett’s fingers withdrew from Leo’s ass, leaving his sensitive area feeling strangely empty but primed. Brett moved back slightly, picking up the bottle of lube Leo had brought over. He squeezed a generous amount into his palm, his eyes still fixed on Leo’s hole waiting for him.
“Alright, let’s do this,” Brett said, his voice low and gravelly. He knelt behind Leo, his gaze running over the powerful muscles of Leo’s thighs and the curve of his ass cheeks, tense with anticipation.
“Damn, you’re built, man. You hit leg day well.” He leaned forward, and smacked Leo’s cheeks before smearing the thick lube around Leo’s hole.
Leo flinched at the slap and the cold lube. He squeezed his eyes shut, biting his lip and feeling Brett’s hand push against one of his ass cheeks, pressing him down slightly, into a better position for entry.
Brett’s hand lifted, and a HARD smack echoed in the room. It stung and sent a jolt through Leo that lowered his confidence considerably for what as coming. He felt, despite his muscular strength, that he was to submit to the All American man, which he embraced.
“Hear that?” Brett’s voice was right behind him, close to his ear now, rough and laced with triumph. “That’s the sound of me taking what I want. You hear me, Leo? This ass? It’s mine now. I own it. Even if you get a girlfriend here, I own this ass until I graduate, got it?”
The words hit Leo like the smack, stealing his breath. He felt Brett’s thick, hard cock press against his entrance, slick with lube, a hammer about to burst through his virgin hole. Leo let out a deep moan.
“You like hearing that, don’t you?” Brett taunted, his voice dropping to a husky whisper. “Little virgin ass, ready for my cock? Gonna stretch you open, make you feel gaping.”
Leo swallowed hard, his throat tight. He tried to find his voice, to throw back some witty retort, but was obsessed with finally submitting to a man sexually, “M-make me feel it then.”
Brett chuckled, a deep, satisfied sound that vibrated through Leo’s core. “Oh, you’re gonna feel it. All of it.” He positioned the head of his dick against Leo’s opening, pushing.
The sensation was intense, a deep pressure that made Leo tense up. It was wider, harder, more than anything he had ever used down there. He felt the thick ridge of Brett’s head pressing, stretching, forcing its way inside. He gasped, his knuckles clenching, “fuck fuck fuck…”
“Easy, easy,” Brett murmured, though there was no gentleness in his action, only a relentless push. His muscles, though not ripped, had the solid, working-man strength of someone used to physical labor, and he was using it now. Unlike Kieran’s tenderness, Brett just continued pushing, a millimeter a second, giving Leo little to no time to adjust to the massive tool ripping him open from the inside.
A tear pricked at the corner of Leo’s eye as the thick head ventured further inside of him. A sharp, ripping pain flared with a sense of being filled and stretched to capacity. He cried out, a raw, uncontrolled sound, his body arching even further, trying instinctively to escape the intrusion from behind. Kieran, Frederik, Dev, and Adam all paused what they were doing to look over to see if Leo was ok. Brett shot them a hand wave to focus on themselves.
“Scream for me, bitch,” Brett snarled with a note of excitement in his voice, fueled by Leo’s reaction. He paused for only a moment when he got the first four inches in, letting Leo’s body try to adjust, only because Leo’s muscles were completely resisting him from going further, “cmon, relax, stop squeezing shut.” The grip was like a vacuum seal. He pulled back, enough to feel the edge of his head slip out, then thrust forward again, harder this time, putting about five inches inside of Leo in a burst, breaking past the inner ring that had been resisting his huge cock.
“FUCK AGGHHH,” Leo screamed out in the room.
“BRETT! Take it easy!” Kieran called out from Frederick’s bed.
“Okay okay. Leo, you okay?” Brett checked in briefly, dropping the dominant act.
“Ugh it hurts but fuck yeah, I want it,” Leo ground his teeth through a tear.
Brett smiled and pushed the remaining three inches in as fast as he could, his balls hitting Leo’s hairy ass cheeks with a moist embrace.
“Fuck, you took it all,” Brett groaned, sweat starting to bead on his forehead despite the relative ease with which he usually took his partners. He held eight inches of thick cock inside of Leo, amazed that the virgin had so much meat inside his ass for him, “fuck that’s hot, how’s that cock feel?”
“So fucking big…” Leo whined, his voice jumping an octave from its usually deep tone.
Brett began to move, feeling the tight resistance, then pulling back almost to the start before driving in again.
“AHHH FUCK,” Leo whined.
Each thrust of almost all eight inches sent a jolt through Leo’s body. The pain was immeasurable but slowly, his body turned numb from the psychological pleasure overwhelming his senses. He felt a burning ache in his abdomen, a rising orgasm from nothing other than the gigantic meat destroying him from within.
“You feel that?” Brett asked, his voice strained with effort but still laced with dominance. He grabbed Leo’s hips, holding them firmly, controlling the angle and the depth. “That’s all cock, stretched out inside you. Feels good, doesn’t it? Feels like I own you. You’re not bi anymore, you’re just my bitch now.”
Leo’s breath hitched with a sob that was half pain, half pleasure. “Mm-hmm,” he whimpered, unable to deny the overwhelming sensation. The pain was real, a sharp edge to the experience, but the pleasure was a tidal wave threatening to drown him, a deep hammering that intensified with every rough thrust as he lost his anal virginity to this man.
Brett’s pace quickened, his thrusts becoming more forceful, more relentless, turning to jack-hammering Leo with about six inches of dick. He was breathing hard, his face flushed with exertion amid the high of the power trip. His dick felt amazing buried inside Leo’s muscular ass, stretching him wider and wider with each deep pump. His balls slapped hard against Leo’s cheeks, turning him on even further despite the light taps against them over and over and over again.
“God, I’m gonna stretch you out good. Make sure everyone knows who’s been in here.” He leaned down, grabbing a handful of Leo’s hair, pulling slightly and driving his cock all the way in again. “You’re gonna remember this forever, pretty boy.”
Leo cried out again, the pull on his hair adding another layer of sensation. His hips bucked, meeting Brett’s rhythm, chasing the intense pleasure that was now eclipsing the pain. He felt himself getting closer, the unfamiliar searing ache in his ass replaced by a building pressure low in his belly. His cock drooled pre-cum underneath him onto the sheets.
Brett let go of Leo’s hair, his hand going to his lower back, pressing down, ensuring maximum depth with each thrust. He could feel himself getting close, the pressure building in his balls, the friction inside Leo’s tight ass pushing him over the edge.
“Fuck, I’m close. I’m gonna breed that ass. It’s mine,” Brett groaned. His thrusts became frantic, faster, harder. He slammed into Leo again and again, burying himself inside.
Leo reached down with a shaky hand and wrapped his fingers around his own hard, large in its own right, seven inch dripping cock. He stroked himself underneath, mirroring the rhythm of Brett’s thrusts inside him.
Brett threw his head back, a roar escaping his mouth as he felt the hot, thick flood of his cum pump into Leo’s ass. He groaned, collapsing forward slightly, burying his face on Leo’s back, pumping his seed into the warm cavity beneath him. Leo cried out as Brett’s cum filled him, fullness washing over. He came with a loud groan of his own, his body convulsing and his own hot cum spurting from his tip onto the bedsheets underneath.
They panted heavily, Brett pushing all eight inches back inside him, stretching Leo to his absolute brim. Leo felt completely drained, his body trembling with the aftershocks of his first time taking a cock, of losing his virginity to Brett. He felt open and owned, and collapsed onto the bed, laying in a pool of his own cum. His strength was completely gone.
Once he was ready, Brett pulled out in as quick a motion as he could muster, watching Leo’s startled, shocked response in going from completely filled by thick meat to wide open and gaping, his hole stretched out at the entrance and red from the beating it’d taken.
“Oh god,” Leo moaned, feeling empty, as if he was missing a body part.
“You did good…” Brett gave him one more loud smack on his ass and got up to pull his underwear back on. Leo collapsed onto his bed again, unable to move, exhausted, every ounce of energy gone from his body.
———————————————
Adam chuckled softly with amusement realizing he was the first person to work Dev’s dick. “Yeah, okay, fair enough, mate. Didn’t realize I was popping cherries tonight.” He pulled back fully, giving Dev a moment to catch his breath, his own member still standing at attention, sleek and dark against his skin.
Dev swallowed, his throat dry. His heart was still racing, the echoes of the blowjob buzzing through him. He looked down at himself, still hard and glistening, then back up at Adam, whose smile was easy and understanding. The awkwardness was there, a faint shimmer.
“So,” Dev started, his voice a little stronger but still shaky, “my turn?”
Adam nodded. “Yeah. No pressure thought, yeah?” His eyes held Dev’s for a second.
Dev took a deep breath and shifted his position on the bed. He wasn’t sure how to start. He glanced at Adam’s cock, only slightly bigger than his own, perfectly formed and dark. It was fascinating. He hesitated for a moment, his hand hovering awkwardly.
“Just take your time,” Adam said softly, repositioning himself slightly to make it easier for Dev. He leaned back on his elbows, his legs spread open invitingly.
Dev knelt between Adam’s legs, feeling clumsy. He reached out, his fingers brushing against Adam’s skin. It was warm and so hard. He tentatively cupped the head, feeling the firm shape, the slit at the tip. It felt strangely natural, not all that different than his own.
He leaned down slowly, opening his mouth, lips slightly parted, and lowered himself until his mouth closed around the tip. It wasn’t what he expected. The texture was rough, the taste just skin, maybe a little salty, but not nearly as gross as he would’ve imagined. He flicked his tongue tentatively against the head, mimicking what Adam had done to him. Adam let out a low groan, a sound that made Dev’s skin prickle. It was a sound of pleasure, and it was because of him.
“Yeah, like that, mate,” Adam murmured, his voice tight.
Dev tried to take more of Adam into his mouth, sliding down the shaft slowly. He struggled a little to get his mouth around more of it, the thick head pushing against his soft palate. He gagged slightly, pulling back reflexively.
“Whoa, easy,” Adam said quickly, reaching out a hand to Dev’s hair. “Just go as far as you can. You don’t gotta take it all, it still feels good…”
Dev nodded, embarrassed. He focused on Adam’s eyes above him, trying to gauge his reaction. Adam looked calm, a small smile returning. Dev tried again, keeping his mouth only about an inch or two down the shaft, working his lips and tongue, trying to find a rhythm. He started moving his head up and down, awkward at first, then finding a tentative pace. He focused on the warmth, the smooth feel, the subtle pulsing beneath his tongue. He glanced down at his own cock, still hard, and felt a disconnect doing this…to a guy. The thought of fitting in, of being part of this shared experience with his new friends, spurred him on.
Adam’s breathing grew heavier. “Oh yeah, Dev, that’s good. Just like that.” He gripped Dev’s hair gently, guiding his head slightly. Dev felt Adam’s hips start to grind up slightly into his mouth.
He continued for what felt like a long time, becoming more comfortable. He sometimes focused on the head, running his tongue over the ridged crown and extra foreskin, other times trying to take a little more of the shaft, his movements becoming more fluid. He was surprised by how much he was getting into it. He didn’t care much for the fact that it was a penis in his mouth, but felt responsible for delivering pleasure, treating it almost like an exam or a workout to ace.
“Feeling good, mate?” Adam asked eventually, his voice slightly strained with pleasure.
“Yeah,” Dev breathed, pulling back for a second. He was breathless, his knees aching slightly, his own cock throbbing.
“Fancy trying something else?” Adam suggested.
Adam shifted, pulling Dev up towards him. Before Dev fully understood, Adam was rotating Dev around to straddle him from behind, Dev realizing his ass and dick were now hanging near Adam’s face as he looked down at Adam’s dick from the inverted angle now.
Dev stared for a moment at Adam’s cock right there, inches from his face, and then he felt Dev’s mouth close around his own from underneath. It was dizzying. The overwhelming pleasure he’d felt minutes before surged back through him. He lowered his mouth down and took Adam back in. The sensation of being sucked while sucking someone else was fueling him. Adam’s mouth was hot and wet, working him, while Dev tried to figure out how to reciprocate in this inverted position.
They moved together, finding a rhythm. Dev looked back at Adam’s face, upside down, seeing his eyes closed, his brow furrowed in concentration. He tried to push down further on Adam, mimicking the feeling he was receiving, running his tongue along the underside, feeling Adam’s hips tilt slightly in response. Unconsciously, Dev found himself beginning to hump into Adam’s mouth, grinding his hips downward, his hole pointed upward felt the cool dorm room air in this position on all fours. He felt himself getting close
“Adam, I…I don’t want to swallow it,” Dev gasped out, pulling his mouth off Adam for just a second, the words tumbling out in a rush right as the feeling crested.
Adam’s eyes opened, meeting Dev’s. He nodded quickly, understanding immediately. “Got it, no problem.”
Adam quickly pulled them apart from their tangled position. Dev scrambled to sit back next to Adam, his cock throbbing, painfully hard, and drenched in Adam’s slobber. Adam did the same beside him. They didn't look directly at each other as they each grabbed their own shafts.
Dev gripped himself, stroking hard and fast, his eyes closed, riding a wave building inside him. Beside him, he could hear Adam’s rapid breathing, the soft, wet sounds of his own hand rubbing his cock. He opened his eyes and looked to his peripheral, seeing Adam’s ripped, large, muscles contracting.
Dev stroked faster, faster, pushing himself over the edge. He squeezed his eyes shut, his body arching slightly, and gasped, his muscles contracting as he collapsed back onto his bed and shot a thick rope of cum over his head, hitting the wall above. His panting orgasm mixed in with a mesmerized giggle at the crazy first shot as more semen poured out, onto his belly and pubes.
Adam let out a long, shaky breath and slowly opened his eyes. He turned his head to watch Dev fire off a wad of cum at least three feet through the air onto the wall above him. He let out a laugh just as his own orgasm peaked and released. He slowed his jerking, focusing on gripping and rubbing his ultra-sensitive head, thick cum dribbling out, just barely reaching his abs, contrasting his dark, smooth skin with slick, sticky, wetness. They both heaved and shared a glance and a chuckle.
—————————————
Frederik was hypnotized, completely lost in Kieran’s movements inside of him. He couldn’t even begin to explain how he went from disgusted by the thought of the act to feeling now more emotionally alive than ever before. Kieran felt Frederik’s body beneath him, tense with discomfort but emerging pleasure. He maintained a slow, steady pace, his focus entirely on the younger man’s well-being and determined to reach the point of him enjoying bottoming.
He could feel every tiny clench and release of Frederik’s muscles around his dick, strangling his penis from the inside. The virgin hole still fighting back as it was breached.
“Just breathe through it,” Kieran murmured, panting against Frederik’s neck. He pushed a little further, holding still for a moment, allowing Frederik’s body to acclimate. He felt a shiver run through Frederik, saw the white-knuckled grip on the pillow. He didn’t want to hurt him, only to make him feel good.
“Are you okay? We can stop.”
Frederik shook his head frantically against the pillow. “No. No, don’t stop. Just…give me a second.” He took a shaky breath, trying to relax his muscles.
Frederik bit down harder on the pillow, a muffled groan escaping him. The burning, stretching sensation was still there but he began to feel pleasure, sensing a spot inside that sent waves through him like an atomic bomb. He focused on Kieran’s pleasured breathing, realizing it was his ass bringing the older man pleasure. His mind was a confusing swirl of ‘what am I doing’ and ‘this is incredible.’
Kieran waited, his hand still stroking Frederik’s inner thigh, the smooth skin soft under his touch. He watched Frederik’s back tense and then slowly relax. It seemed soft and he felt the desire to caress and be with the younger Dane. He felt like he might be falling in love.
“Ready?” Kieran asked softly.
Frederik nodded again, his voice trapped in his throat.
Kieran began to move again, still slow, but pushing deeper this time. Frederik gasped, the initial discomfort flaring, but this time it was quickly followed by a deep, throbbing pleasure.
“Fuck,” Frederik whimpered, burying his face deeper into the pillow. His hips instinctively lifted slightly, an involuntary movement that surprised him. It was a subconscious plea for more.
Kieran felt the subtle shift in Frederik’s body, the tiny lift of his hips, it was the signal he needed. He began to increase the speed of his thrusts, pushing a little further with each stroke, still careful, still watching for any sign of distress, but guided by Frederik’s silent cues.
He leaned down, his chest pressing against Frederik’s back, wrapping his arms around him, holding him close.
“You’re doing so well,,” he whispered against his ear, planting a kiss there. “You’re amazing”
Frederik felt Kieran’s embrace, the solid weight of him pressing against his back. He let go of the pillow with one hand, reaching back and finding Kieran’s forearm, gripping it tightly. The distinction between pain and pleasure blurred, becoming a single, intense wave of sensation washing over him. He felt the full length of Kieran inside him now, every inch of that Irish cock sliding in and out of his tight butt.
“Kieran…” he gasped, the name a soft plea. He didn’t know what he was asking for, only that he needed him.
Kieran tightened his grip on Frederik’s body, feeling the younger boy’s desperation. He increased the pace slightly, the thrusts becoming a little faster.
Frederik felt himself losing control. His hands gripped Kieran tightly, his fingernails digging lightly into his skin. He could feel his own dick underneath him, pressed against the bed, twitching again, reloading from the blowjob he’d received.
“Oh god,” he moaned. He felt the pain fade away, as an intense spot in his pelvis shot lightning through his body every time Kieran humped inward. Suddenly, heat hit his entire groin, a rush of sensation from head to toe. “Kieran…Kieran….it feels so good now…oh my god…that’s so good…” He felt tears at his eyes, a strange combo of emotion and physical release.
Kieran felt Frederik’s body tremble against his, heard the euphoric cries as he found the perfect angle to ram his prostate over and over again. He was close too, the grip of Frederik’s hole pushing him towards the edge.
Frederik felt his orgasm building again. His muscles tensed, his glutes squeezing, strangling Kieran’s cock even more somehow. He squeezed his eyes shut, holding tight onto Kieran’s arm, as release washed over him. He felt his asshole clench over and over and over again as he came onto his bed, squealing and whimpering from the best feeling he’d ever experienced in his entire life.
Kieran felt Frederik’s climax ripple through his body, violent tremors underneath him matching a series of clenches around his dick that literally milked the cum out of him. He groaned, plunging deep one last time, his body stiffening as he released inside Frederik.
“Ahhh aghhh ahhh,” He opened his mouth wide and unabashedly let out loud, deep, moans, pumping a gallon of his seed into the Dane for what felt like a full minute. He collapsed onto Frederik’s back, his chest heaving, their bodies stuck together with sweat.
Frederik lay still, his face still buried in the pillow, his body feeling like it might float away. He was fucking exhausted. Kieran carefully shifted his weight, rolling slightly to the side and removing his softening penis from the tiny ass below him. He rested his head near Frederik’s, his breath warm against his ear.
“I…I really like you,” Kieran whispered, his voice husky with shocked emotion. Frederik felt a tenderness swell in his chest.
Frederik slowly turned his head, his eyes, wide and vulnerable, meeting Kieran’s. His cheeks were flushed, his hair messy. He didn’t speak, couldn’t speak, still processing the whirlwind of feelings and sensations that had just consumed him. He reached out a shaky hand and gently touched Kieran’s face, his fingers tracing the scattering of freckles on his pale skin.
They embraced in a warm, sensitive kiss, silently expressing their shared, unexpected feelings for one another. Something neither would’ve ever predicted three hours ago.
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