âËËŕźŘ late night confessions
synopsis: after confessing how you've never had any of your firsts, frat boy!caleb is there to listen (and help  á´ÂŹ) but he also has something to confess aswell?
tw: MDNI +18, p in v (use protection), virginity loss, fingering, cummin inside, oral, squirting, teases a bit, caleb is a bit of a groaner, your pleasure comes first!!
author's note: hihi lovelies! so sorry i took awhile to post, life has been busy. i wanted to make something extra long because i will continue to be busy these next few weeks so i dont know when i'll be able to post but thank you so much for the love on held close, it was my best work and i wanted to capture the essence on how caleb is hehe. happy reading!
this wasnât unusual. you and caleb always ended up like this after nights out. he might be the life of the party, but he never let you walk home alone. not when he could just let you crash here, giving the two of you privacy while his roommate was away.
he took a sip from his water bottle, tilting his head to the side as he studied you. âyou looked miserable down there,â he said, a smirk tugging at his lips. âdonât tell me youâre finally admitting frat parties arenât your thing.â
you rolled your eyes. âthey never were.â you take a sip from your water bottle that caleb handed to you.
he chuckled, setting the bottle on the nightstand. âthen whyâd you come? you know i wouldnât have invited you if it meant you would feel terrible.â
you hesitated, tracing patterns on his blanket. âi dunno. just figuredâŚwell itâs college. i should probably try to enjoy it like everyone else.â
caleb hummed like he didnât quite believe you. âuhuh and did you?â
you shot him a dry look. âi spent half the night dodging drunk guys who couldnât take a hint, so what do you think?â
his smirk faded. âwho?â
ârelax, nothing happened,â you said quickly. âbut thatâs kind of the problem, isnât it?â
caleb frowned, pushing himself up so he was properly sitting. âwhat do you mean?â
you let out a slow breath, you looked down at the floor. âi just⌠i feel like iâm behind.â
âeverything,â you admitted. âiâve never had a real boyfriend. never had my first kiss, never-â you paused, suddenly regretting saying anything at all. ânever mind. itâs stupid.â you dismiss your comment with a slight chuckle.
caleb was quiet for a moment. when you finally glanced up at him, you expected teasing, maybe some cocky remark about how he could âfix thatâ if you wanted.
but he just looked⌠thoughtful.
âthatâs not stupid pipsqueakâ he said finally. his voice was quieter now, more serious.
you sighed. âcome on, caleb. you..youâve lived. youâve had hookups, flings, relationships or whatever you call them and iâve had nothing.â
he gets closer and sits next to you on his bed, keeping his gaze. âand? why does that matter?â
âbecause,â you huffed, frustrated. âpeople expect you to have certain experiences by a certain age, and i just⌠havenât.â
calebâs brows furrowed. âwho the hell cares what âpeopleâ expect?â
you bit your lip, shrugging. âitâs just embarrassing sometimes. i feel like iâm missing out.â
he was watching you closely now, something unreadable in his gaze. âyouâre not missing out on anything, pipsqueak,â he murmured.
your stomach flipped at the nickname, but you ignored it. âeasy for you to say. youâve had all your firsts.â
caleb froze but leaned closer, something like a smirk tugging at his lips, but it wasnât cocky this time. he cups your cheek. âyeah? and you wanna know something?â
you hesitated before nodding.
âthey were forgettable.â
that caught you off guard. âwhat?â
he exhaled, running a hand through his hair. âi mean⌠there were moments. but i could never look them in the eye. i just couldnât..â his fingers curled into the fabric of his hoodie, gaze flickering away. i always made sure i wasnât facing them, like if i did, itâd make it real and something in me would just freeze.âÂ
he let out a short, almost self-deprecating laugh. âlike some part of me knew it wasnât supposed to be with them or other times i would call them the wrong name.. and it would be the same name every. single. timeâ his jaw tightens, now his gaze never left yours.Â
your stomach twisted. âcalebâŚâ
he shook his head, forcing a smile that didnât quite reach his eyes. he ruffles your hair. âyouâre not behind, pipsqueak. youâre just waiting for it to actually matter.â
your breath caught. âyouâve neverâŚ?â
he shook his head once, a small, almost embarrassed smile tugging at his lips. ânot in the way you think.â
the room felt smaller somehow, the space between you charged with something unsaid.
âyou donât regret that?â you asked quietly.
he hesitated, he huffs. âi think iâd regret it more if i gave my firsts to someone who actually meant something⌠and they didnât feel the same.â
your heart stuttered in your chest, the weight of his words pressing down on you. but before you could say anything, caleb just gave you a lazy, lopsided smile, like he hadnât just dropped a big piece of his life on you. he grazed your cheek, his touch lingering for just a second too long.
âdonât stress about it, okay?â he murmured. âyour firsts should be with someone you want them with. not just someone convenient.â
a heavy silence settled between you, but your mind was spinning now, turning over every moment, every lingering touch, every look he had given you that you never understood, until now.
âall those girls,â you said hesitantly, your voice quieter now. âthe ones youâve been with⌠did none of them ever mean anything?â
caleb stiffened, his jaw tightening. he looked away, exhaling sharply through his nose like he was debating whether to tell you the truth.
then he muttered, almost too low for you to hear. ânone of them were you.â he finally admitted.
you felt your cheeks heat up by the sudden change in tone.Â
he scoffed at himself, scratching the back of his head. âitâs silly, huh? iâd go out, find someone who-â he let out a humorless laugh. âsomeone who looked just enough like you if i squinted. your hair and that same kind of smile that i adore too much. sometimes they even smelled like your vanilla perfume.â
you stared at him, your heart beating against your ribs.
he shook his head, laughing bitterly. âand for a while, it worked. iâd close my eyes and pretend it was you. just for a little bit.â his voice dropped lower, ashamed. âbut then itâd be over, and iâd wake up, and it wasnât. and iâd hate myself for it.â
you swallowed hard. âcalebâŚâ
his eyes met yours again, and for once, there was no smirk, no teasing glint. just raw honesty.
âbut that didnât stop me,â he admitted. âbecause i thought..heh i convinced myself..iâd never actually have you. and if I couldnât, then what was the harm in pretending?â
a heavy silence settled between you. your chest ached, not just for him, but for yourself, for all the moments you never realized he was looking at you like that. the only thing that echoed now was the faint music from the speakers coming from the party downstairs.
ââŚand now?â you whispered.
caleb exhaled, something almost resigned in his expression. âand now i donât even wanna pretend anymore.â
âyou donâtâŚhave too..â you whispered as both of your faces were mere inches from each other. a quiet breath came first followed by caleb looking down at your lips before he traced his hand down your chin. then, caleb kissed you.
he was slow at first but hesitant, as if he was still trying to convince himself this was real. his hand slid to cup the back of your neck, pulling you in deeper. he places your back on his bed, the weight of him settling over you while fighting for dominance with his tongue.Â
he kissed you like he was making up for every stolen glance, every moment spent pretending. his tongue brushed against yours, coaxing, claiming, demanding in a way that sent heat pooling in your stomach.
then he slowed, breathing heavy as he pulled back just enough for his forehead to rest against yours. his thumb traced your jaw, his voice barely above a whisper.
"tell me to stop," he said, but his voice wavered, like he was terrified of what heâd do if you actually did.
you swallowed hard, your hands turned to knuckles."i donât want you to."
a sharp exhale, like he had been holding his breath. his lips ghosted over yours, his grip tightening ever so slightly. his breath hot over your lips "then tell meâŚ" his voice was desperate. "tell me that whatever happens next, you wonât regret it." he grabs your hand to kiss it before looking into your eyes once more awaiting your answer. âi want to be your first.â his puppy eyes now settling upon you.Â
you lifted that same hand, brushing your fingers through his hair. âcaleb,â you whispered, soft but certain. âi could never regret you. i want this more than you could ever know.â
with a warm smile, he kissed you again, harder this time, more sure of himself. his hand slid down your waist, grounding himself in the feeling of you beneath him.
his hand traced the curve of your cheek before trailing lower, his lips followed.
he dove into your neck, attacking you with nibbles. what started as slow, lingering kisses turned into teasing bites that sent a shiver down your spine. his teeth grazed over your skin before his tongue followed, soothing the marks he was leaving behind. your clear skin was now painted with his touch, evidence of his undying love for you. he thought, what could be just a one-night fling to you, felt like more than everything to him. if what was happening now was just for one night, he was determined to make this into a memory that was worth to keep him going.Â
he trails a free hand to the base of your skirt, tugging on the zipper while his lips stay latched on your neck. with a sudden âzzzipâ filling the room, he continues his path, guiding his hand lower and successfully reaching inside your underwear. you felt shivers down your spine as caleb rolls circles on your clit, sending a gasp out of you.Â
you grip at his shoulder, feeling the fabric of his jacket wrinkle under your grasp. you didnât know how to comprehend the amount of pleasure he was giving you. moans started to escape your lips as caleb continued to caress your clit, his every touch left you almost breathless but wanting more. your body started to tense up, an unknown feeling that only escalated your arousal.Â
caleb let out a low chuckle before trailing a series of soft, lingering kisses along your lips. just as you try to keep up with your breath, he captured your mouth again, tilting your head to deepen the kiss, his touch both teasing and possessive. his tongue slipped past your parted lips, prying your mouth open as he explored you further, muffling your shaky moans with an intense and consuming kiss.
âthis feels s-so good..â you managed to whisper in between kisses, your body responding to every relentless touch. caleb still not losing his rhythm on your clit, his lips never leaving yours as he pulled back just enough to smile.
"i'm glad..because I wonât be stopping anytime soon," he said, his voice low and teasing.
his words sent a thrill through you, a mixture of excitement and anticipation pooling in your stomach. the more he kept playing with your clit, the more this..unknown sensation was rising inside you and he didnât want him to stop.Â
pulling his fingers away, you immediately missed the feeling, a whimper catching in your throat. before you could make a fuss on the loss, caleb dipped his head down, his breath warm against your skirt, nearing your cunt. you sucked in a shaky breath, trying to regain some semblance of control. your eyes, heavy-lidded and hazy with pleasure, flickered to the window. the stars had never looked so bright, distant, shimmering, and endless, just like the party still going on downstairs.
his hands found your hips, thumbs pressing into your hip bones in a slow, soothing motion before he hooked his fingers into your skirt. with a smooth tug, he slid it down, taking your underwear along with it, leaving you bare beneath him. caleb glanced up, his eyes smoldering as he murmured, "after tonight, i promise..this is all you'll ever think about."Â Â
before you could even form a response, he lifted one of your legs over his shoulder, keeping you open for him. then, without warning, his mouth descended on your exposed pussy. Â
the first swipe of his tongue was slow, deliberate, as if he wanted to savor you, to let the taste of you settle on his tongue. but that restraint didn't last long. his groan vibrated against your core, low and needy, like he was already losing himself. his hands gripped your thighs tighter, fingers pressing into your flesh like he needed something to ground himself. but even then, he was slipping, unraveling with every lick, every sound you made. Â
his tongue moved with an eager desperation, tracing over your folds, as if he was memorizing the way you felt against his tongue. he devoured you like a man starved, each groan growing rougher, throatier, as his self-control decreased. his movements became sloppier, greedier. his lips sealing around you, sucking just to hear you gasp, his tongue lapping up every drop like he couldnât get enough. Â
when he pulled back just slightly, his lips glistening, his breath ragged, his pupils were blown wide, almost black with hunger.
 "fuck..." he exhaled, his voice rawly thick. his grip on your thighs tightened for just a second before he dove back in, dragging another long, almost desperate lick through your folds, like he had lost all sense of anything else but you.Â
your fingers tangled in his mullet without thinking, pulling him closer as your hips rocked against his tongue, chasing every wave of pleasure he gave you. the heat pooling in your stomach burned hotter with each flick of his tongue, each hungry suck that left you trembling beneath him. Â
"calebâ" his name slipped out in a breathless moan before you slapped a hand over your mouth, trying to stifle the sounds spilling from your lips. "that feels⌠s-so good," you mumbled against your palm, your voice barely holding together. Â
but caleb wasnât having that. Â
still buried between your thighs, he hummed against you, a deep, satisfied sound that sent vibrations straight through your core. without pausing, he reached up, his fingers wrapping around your wrist, pulling your hand away from your lips. he laced his fingers with yours, his grip firm, grounding. Â
his lips curled into a smirk against you before he murmured, voice thick with want, "you donât have to hold back. be as loud as you want⌠iâm right here."
he pushes you back, pinning you against the bed with ease, his face still hovering over your pussy. Â
a sharp cry cuts off your words as his fingers sink into you, stretching you open inch by inch. the sudden fullness sends a jolt of pleasure through you, making your body arch into his touch. before you can even catch your breath, his tongue joins the mix, dragging along your folds with a slow, deliberate lick that has your thighs trembling. Â
"you taste so sweetâŚ" he groans against you, his voice dripping with hunger. "i could do this all night..all day even", he chuckles.Â
your slick coats his fingers as he pumps them in and out, the pace teasingly slow, as if heâs memorizing every reaction, every little sound you make. your whimpers fuel him, a spark igniting in his chest as he watches you come undone beneath him. Â
then, he curls his fingers just right-Â Â
your back lifts off the bed, a choked moan escaping your lips as your body tenses. his smirk deepens, dark and knowing. heâs found it. Â
"there it is," he murmurs, his voice dripping with satisfaction. he doesnât waste a second. his fingers pick up speed, thrusting deeper, pressing against that same spot over and over again. every movement is deliberate, every stroke meant to unravel you. the room fills with the slick sounds of his fingers working inside you, the wet heat of his mouth still teasing your clit, and the way your moans spill out, growing louder with every calculated thrust. Â
caleb hums against you, his own pleasure building just from watching you come apart. "thatâs it⌠let me hear you."
your grip on his hand tightened, fingers trembling as your body squirmed beneath him. a desperate whimper escaped your lips.
âc-caleb⌠iâah⌠i think iâm close,â you gasped, your voice breathless, barely above a whisper.
his response was immediate, âcome for me, princess⌠iâm right here.â
a shiver ran down your spine as his words alone sent you teetering on the edge. your back arched, muscles tensing as pleasure coiled tight in your core. caleb didnât stop, his touch was relentless, his tongue and fingers working in perfect sync, dragging you through wave after wave of ecstasy.
your release crashed over you, sending you spiraling. a gasp came from your throat as warm liquid flooded through you, coating his face and fingers soon part of the liquid dripped down to the bed. caleb groaned against you, savoring every moment, every sound, every taste. he pulled away only to lick his lips, eyes dark with satisfaction as his thumb traced soft circles on your inner thigh.
âthatâs my good girl,â he murmured, his voice dripping with praise, a smirk tugging at his lips. even now, with your body spent and breath uneven, the hunger in his gaze told you..he wasnât done with you yet.
he wastes no time before hovering over you, caging you beneath him. his fingers fumble slightly as he works at the buttons of your top, eager yet unsteady. one by one, they come undone, revealing more of your skin to his hungry gaze. his pupils darken, widening with sheer desperation. he had imagined this moment countless times, but nothing compared to the reality of seeing you like this. Â
âyouâre even more stunning than i imagined,â he breathes, voice thick with longing. the last of the buttons popped off and you help him as he gently swifts it off your shoulders, putting it to the side. thereâs no hesitation in his movements as he expertly unclasps your bra with a single hand, discarding it just as quickly.Â
for a moment, he simply stares, enamored, breath hitching as if he doesnât know where to begin. but desire overtakes him, and he dips his head, capturing one of your sensitive buds between his lips. the moment his mouth latches on, he sucks greedily, the same feeling he had between your thighs now channeled into worshipping every inch of you. he makes sure to give the other breast the same attention, his fingers kneading your soft flesh while his mouth continues its worship. caleb was always the type to ensure you were taken care of, and this was no different. his touch was deliberate, yet dripping with desire. Â
your whimpers slip past your lips, each sound fueling him further as he overwhelms you with sensation after sensation. his tongue flicks and rolls, alternating between slow, teasing swirls and desperate, heated sucks, never giving you a moment to recover. every movement was a silent promise. he wasnât stopping until you were completely undone beneath him.
eventually pulling his lips away from your breasts, his breaths were ragged, heavy with restraint as his fingers made quick work of his belt. âyou have no idea what you do to me,â he murmured, the sharp clink of metal echoed in the room, followed by the unmistakable sound of a zipper being dragged down.Â
his hands trembled slightly, whether from excitement or the sheer need to feel you, you werenât sure. but the moment his pants hit the floor, he wasted no time. he leaned back over you, the heat of his body radiating against your skin as he traced a hand along your thigh, his touch very worshipping. he releases his erection from his boxers and he was big. his tip glistened with pre-cum. he guided his cock before your pussy.Â
âiâll go slow, i promiseâ he breathed out, using your slick to coat himself. he aligned himself with your entrance, teasing you with the tip before slowly pushing in, letting you take him inch by inch.
a groan ripped from his throat as your walls wrapped around him, his fingers digging into your hips as he tried to steady himself. his head fell forward, his breath hot against your shoulder. "fuck," he rasped, voice shaking. "you'reâyou're squeezing me so tight." he shakily pumps in you slowly.
"c-caleb," you whimpered, voice breaking as you tried to adjust. "you're so⌠bigâ"
his grip on you tightened, his chest rising and falling in heavy pants. "god⌠you feel too good," he nearly whimpered, his voice filled with desperation. his body trembled, pressing his forehead against yours as he fought for control.Â
âif you keep squeezing me like that,â he murmured, his voice husky and uneven, âi donât think i can go slow.â
you swallowed hard, your walls fluttering around him at his words. âplease⌠donât,â you whispered, meeting his half-lidded gaze with your own. "i want to feel all of you." you tugged at his jacket, it being the only clothing left on between the two of you. you slipped your hands beneath the fabric, pushing his jacket off his shoulders before sliding it down his arms, letting it fall carelessly to the floor along with your clothes. you guided your hands on his chest, feeling every muscle he had. you were used to seeing caleb shirtless but tonight, it was in a different light that only increased your arousal.Â
once he was halfway in, his breathing started to become heavy as he studied your face for any sign of discomfort. âalright..â he hums, his thumb stroked gentle circles on your hip. âbut tell me if itâs too much,â he whispered.
your nails dug into his shoulders, your body desperate for more despite the slow burn. âkeep going,â you urged, your voice breathless and cheeks flushed.
caleb let out a shuddered exhale before pushing deeper, groaning as he finally bottomed out inside you. he buried his face in the crook of your neck, overwhelmed by the warmth embracing him so perfectly. his body trembled to move at a pace that wouldnât break you, despite the way your walls clenched around him.Â
your moans became louder as caleb continues to fill you, his hair becoming a bird's nest under your fingers. âc-caleb..moreâ you bit your lip, scratch marks forming on his back the more you cling onto him. âhhhgâŚi need moreâ you pleaded. a smirk tugged at the corner of his lips before he captured your mouth in a searing kiss, his restraint finally snapping as he began to move in a quicker pace, rocking into you with deep, measured thrusts that left you gasping.
caleb groaned against your lips before pulling away, his hands gripping your thighs as he adjusted his position, sliding his hands under your legs before lifting them onto his shoulders. the shift made you gasp, the deeper angle sending a shiver through your entire body. the perfect angle he knows to get you into a mess. he leaned forward, pressing your knees closer to your chest, trapping you beneath him.Â
"c-calebâ" you choked out as he pushed back in, deeper than before, the sensation overwhelming his grip on your thighs tightened as he adjusted, his thrusts being so deep, hitting that sensitive spot inside you with precision. every roll of his hips that kissed your g-spot sent sparks of pleasure shooting through your body, your moans growing louder with each push and pull.Â
calebâs breathing was ragged, his control unraveling as he watched you writhe beneath him. "look at you," he murmured, his voice dripping with admiration. "so beautiful like this..so perfect for me." he places a kiss on your calf.Â
you reached for him, hands on his chest to gesture him to slow down. something was building up in your core. sounds of skin slapping filled the room. "iâm-..so cl..close caleb.."Â
"i know," he cut in, voice strained as he instead quickened his pace, wanting your release to fall through for him and by him. "give it to me... please let me feel you.."Â
with a final, deep thrust, he angled himself just right, sending you over the edge with a cry, your body tightening around him as a warm liquid gushed out of you. the liquid coated on calebâs cock and inner thighs. witnessing this, caleb groaned loudly, his hips stuttering as he came completely undone by the way you pulsed around him. his movements grew more erratic as he felt your walls clamp down around him. the grip on your thighs tightened, as he tried to hold himself together.
"good girl.." he panted, his mind still onto the sounds and the expressions of you coming undone before him. he continued thrusting, now chasing his high. after a while, caleb announces âiâm ugg.. gonna..â his body comes to a stop as he releases his seed inside of you, coating your walls.
the world around you both seemed to have stopped, nothing but the feeling of him filled your mind. caleb's weight sank into you as he rested his forehead on your shoulder, trying to catch his breath.
a small smile curled at your lips as you traced your fingers through his damp hair, feeling his body twitch slightly against yours. "that wasâŚ" you trailed off, still breathless, your mind hazy from the intensity of it all.
caleb let out a weak chuckle, pressing a soft kiss against your collarbone before pulling back just enough to meet your gaze. his purple-pinkish eyes, still heavy with satisfaction, softened as he took you in. "yeah," he murmured, brushing his knuckles along your cheek. "it was."
he slowly pulled out of you, making sure to be gentle as he settled beside you, pulling you into his arms without hesitation. his hands roamed over your bare skin, his eyes full of adoration. caleb reached for the blanket, pulling it over you both, carefully covering you up as if protecting the moment, his moment. he held you close, his breathing still getting adjusted for his body to fit around yours.Â
you cleared your throat, lifting your head to face him.
âhey,â you started softly, your voice a little unsure. âearlier⌠when i said i felt like i was behind, that I hadnât had any of those firsts⌠i still feel that way sometimes. even now.â
calebâs gaze softened, and he shifted, lifting his head to look down at you. his hand gently cupped your cheek, his thumb brushing over your skin in a quiet gesture. âyouâre not behind, pipsqueak,â he murmured, tender now. âeveryoneâs timeline is different. and whatever you havenât experienced yet? iâm not going anywhere. iâll be right here, whenever youâre ready for all of it.â
a smile tugged at your lips, his words comforting you. âi know. i guess i just needed to hear that.â
calebâs smile was soft, his eyes full of warmth. he pulled you closer, holding you a little tighter. âitâs not about what everyone else does or what they think. itâs about what feels right for you. donât ever feel like youâre missing out, because with me⌠youâll always have all the time you need.â
you let out a contented sigh, your hand resting on his chest. âthanks caleb,â you whispered. âiâm glad i have you here.â
he kissed the top of your head, his voice with reassurance. âiâll always be here, pipsqueak.â you begun to doze off, leaving the memory of the night you and caleb in your head. he was right, this is all youâll ever think about. âgoodnight, pipsqueak,â caleb whispered softly, pressing a gentle kiss to your forehead. you didnât have the energy to respond, the last of your thoughts dissolving into peaceful sleep.
caleb smiled down at you, his heart swelling with affection. his hand came up to brush a stray lock of hair from your face, his gaze lingering on you with a tenderness that he had always felt for you before. you looked so peaceful, so content, and he could hardly believe you were in his arms, trusting and letting him help with one of your doubts could easily fill him for the rest of his life.
he watched you for a while, tracing the outline of your face with his eyes as you slept, aware of the way his heart beat faster with each passing second. with each second having him fall more and more in love with you. caleb smirked to himself, imagining the questions that would come once gideon finds you sleeping in calebâs bed. he let out a contented sigh, looking down at your sleeping form. âlet him ask. i wonât let out a peepâ he muttered.
not that gideon would believe any excuse, anyway. caleb could say you had a nightmare, that you tripped and conveniently landed in his bed, or that aliens abducted every other available sleeping surface but gideon would just wag his eyebrows and call it bluffing.
whatever. let him talk. let him annoy the hell out of him. caleb didnât care.
all that mattered was the pretty girl curled up in his arms, fast asleep because for the first time in a long time, caleb was exactly where he wanted to be. and nothing else mattered.