❯❯ First times - A NSFW Eltingville Club Fanfiction ❮❮
The boys are »18« now, and ready to have their first romantic experiences with the F! reader. I originally published it on AO3, there's extra stuff in the link! »»» HEAVY NSFW ««« with straight sex ahead. Don't like, DON'T PROCEED. 7k +/- words. (￣^￣ゞ
《 Kiss + Making out: 》 Once he realizes you want to kiss him, he dives all in, hungry. He wants it to be cinematic, epic, and feel like you will be head over heels for him. But he's clumsy and eager, so the kiss is messy; he opens his mouth too much, teeth clash, and he has no idea what to do with his tongue. Once it sinks in he’s actually kissing a girl, he gets nervous, but plays it cool, like he’s in control of the moment (he’s not). He’s a quick learner, and once the kisses evolve into make-out sessions, he becomes comfortable in exploring with you. He wants to be the center of attention; he wants to be good enough so you’ll never let go. He’s performative, grabs your waist, and lets his hands roam wherever you’ll allow. He mutters things, trying to sound bold but coming off dorky. His hands go under your shirt and he tries to unhook your bra, but when he can’t, he fondles your breasts over the bra. He tries to pull your hair, but you deny him and pulls his instead; he pops a boner instantly, and his alpha act crumbles in a second. He then grinds softly against your thigh, hoping you’ll notice his boner and do something about it.
《 Handjob: 》 He sits there stiff as a board, trying to look unfazed, but the moment your hand wraps around him, his brain just blanks. Shit, shit, she’s touching my dick, don’t make a face, act cool. Then you give one stroke and he grunts like an animal. He’s embarrassed at how fast he’s twitching. “Y-yeah, keep going.” he manages, voice cracking. He wants to bark orders, but secretly he’s melting, barely holding back whimpers.
《 Fingering: 》 He dives in cocky, acting like he knows what he’s doing. Except he doesn’t. He shoves his fingers in too quickly, without exploring your folds first. Then panics when you squirm. Crap, crap, I blew it. Slow down, idiot. He tries to adjust, sneaking glances at your face for approval. You help him by guiding him to do it exactly like you do it to yourself, he adjusts quickly. When you moan, his chest puffs out, ego instantly restored. “Y-yeah, I knew you’d like that.” he lies, hiding that inside he’s both terrified and thrilled you're actually wet around his fingers. He loves how warm and moist the walls of a girl are, nothing like he had imagined it would be.
《 Blowjob: 》 He sits on your bed, all puffed up, leaning back like he's a King on his throne, trying to put on this alpha male act he's seen in porn. You are on your knees, his arms crossed like he's in charge. "Yeah, good girl. Do it just like I told you." He wants to sound though, commanding. But the moment your mouth actually takes him in? His whole façade cracks. He gasps, his eyes go wide, lips parting. Shit shit shit it's so fucking warm, oh my God what is she doing with her tongue?!? Inside his head is chaos. His hands twitch like he wants to grab your hair but he's too stunned, then a moan slips out way higher pitched than intended. He sings in his head the Spider-Man's theme to delay his orgasm but to no avail; Soon his thighs tremble, he sweats. He finished way too fast, and stares down at you like he's just seen God. "Yeah, bitch. Swallow my seed, take every last drop. Tell me how good I taste." Too bad you just did, or else you'd probably spit it back in his face, just to remind him who's in charge.
《 Going down: 》 He smiles like an idiot when you open your legs and invite him in. He sees himself as a warrior about to conquer an uncharted territory. He is confident that he knows what he is doing, despite never doing it before. However, once his face is inches away from your pussy, he mildly freaks out. He’s seen porn, sure, but when he gets that first taste, he freezes. His brain screams: It’s... different. Warm. Real. Fuck, what do I do with my tongue? He thinks the taste and smell are way better than he imagined they would be. He licks it sometimes too fast, sometimes too slow, too rough, not really knowing how to keep a rhythm that is going to make his girl come. When you moan despite it, he jolts, staring up wide-eyed. Wait. She likes this? I made her make that noise? His ego balloons instantly. He tries to stick his tongue inside like a dick, and when he fails, he sucks on your folds until he finds the clit. He loves the idea of being trapped between your thighs, being forced to pleasure you. When you come, he feels like a sex God.
《 The first time: 》 He’d been thinking about this moment all week, bragging in the way only Bill could; loud, confident, like he had it all figured out. In his head, sex is supposed to be just another fight he could dominate, something he could face through with swagger and bravado. He thought about this moment for years. When he got a girl, he’d make her beg, she wouldn’t walk straight after. All his comic book macho fantasies had built up to this moment. But now, with your fingers tugging at his shirt hem, reality hit him like a fist to the gut.
You pull over his T-shirt up and over his head. His chest had a few moles and a bunch of zits, if you traced your fingers over them, you could draw constellations. You realize how nervous he is, and hugs him, kissing his neck and whispering into his ear. "Relax."
That word, stabbed him. He wasn't supposed to relax, he's supposed to dominate. To own the moment. His palms are sweating when he touches you, and he swears you can feel his hands shake. You're soft everywhere, too soft, and he doesn’t know where to put his fingers, his lips, his eyes. Every time you giggle, his pride stings, and he doubles down, kissing back rougher than he meant to, forcing his tongue forward, grinding his body against yours like he had something to prove. Like he can force himself into knowing what he’s doing. He is able to unhook your bra, and he tosses it on the ground.
When your hands slipped down, fumbling with his belt, he nearly choked. Fuck this is really happening. He yanked at his jeans himself, clumsy, desperate, half-tripping as he kicked them off. His boxers did nothing to hide how hard he was, and when your eyes flicked down, he felt a flash of both pride and panic.
“You ready?” you asked softly, fingers brushing his waistband. “Of course I’m ready.” he snapped too quickly, voice cracking, as if offended you’d even ask. Inside though, he was dizzy. His heart pounded so loud it hurt. He tore open the condom wrapper with shaking hands, trying to look smooth but fumbling the foil. The rubber nearly slipped from his sweaty fingers.
Get it together, man. She’s watching. Don’t screw this up. Rolling it on felt surreal, the tightness stretching over him, a signal that there was no turning back. For a second, he wanted to gloat, to throw out a line like: You’re lucky to be my first. But he didn’t, his throat was too dry.
You guided him onto the bed, pushing him onto his back. Bill froze at the role reversal, his temper twitching. No, I should be on top. I should be in charge. But when you straddled him, his brain shorted out at the sight of your naked body.
“Holy shit.” he breathed, the words escaping before he could stop them. And with no prior warning, you grabbed his dick and lowered yourself onto him. And thus, everything else; his pride, his fear, his anger, burned away under the raw overload of sensation. His hands grabbed your hips like, holding on too tight, leaving marks. He pushes inside, slow and clumsy. His body locks up. For a split second, his brain screams that he can’t handle it, that it’s too much, too good.
“F-fuck, you’re... tight...” he gasped. His body jerked forward instinctively, thrusting, as if to prove he could take control back. Inside his head, he clung to the fantasy: I’m the man. I’m the one fucking her. She’s mine. He tries to hold back the moan clawing its way up his throat. His rhythm is messy, uneven, hips jerking like he’s caught between holding back and giving in. He tries to control it, to be the guy he always pretends to be; the leader, the one who takes. But every thrust makes his façade crack wider, as he firmly grasps the sheets.
Every squeeze, every slide of warmth around his dick, walls clenching, made his body betray him. His teeth clenched, and a moan slips away. You leaned down, kissing him, and whispered, “You’re doing good.” The words were meant to comfort, but they pierced him, feeding both his pride and his humiliation. She thinks I’m some kid she’s coaching. No. I’m better than that. He bucked harder, rough, making you gasp. For a moment, he felt powerful, triumphant. He slaps your butt. But already, heat was rising too fast, tension spiraling. His whole body was on fire.
No, no, not yet, not this quick... “Fuck!” he shouted, as his climax tore through him. Too fast, too desperate. His back arched, hips jerking wildly, hands clawing your waist as though holding you down could disguise how fast it happened. Shame burns into his chest, and he blurts an apology before he even pulls out. You stroke his hair, tell him it's fine, smiling like he didn't just shatter every illusion he had of being "the man in charge."
He collapsed back onto the mattress, panting, sweat dripping off his forehead. His chest heaved like he’d just run a mile. You kissed his cheek gently. “That was nice.” Bill turned his head away, scowling, humiliated but trying to mask it. “Yeah. Told you I’d be good.” His voice cracked, betraying him. He's feeling humiliated. But beneath that shame, he was furious. At you for seeing him vulnerable, at himself for not lasting, at the whole damn idea of sex not living up to his fantasy. But under that, buried deep, was a tiny ember of awe: I actually did it. She wanted me. Someone actually wanted me.
You curled against him, trailing your nails down his arm. Bill almost flinched at the intimacy. Shit. Don’t look weak. Don’t let her think she owns you. “Was it... good for you?” you asked softly. He snorted, rolling his eyes like it was obvious. “Please. You’re lucky you got me. Bet no one else ever fucked you like that.” His words were cocky, but inside, his stomach flipped. He wanted your approval desperately, needed you to say it.
You smirked, kissed his forehead, and said: “You’ve got a lot to learn.” Anger and arousal tangled in his chest. Learn? I’ll show her. Next time, I’ll prove I can make her beg. His hand slid back to your thigh already, his temper hiding the fact that deep down, he was terrified of how badly he wanted to be touched again. But he'd brag to all his friends about what he'd just done, saying you were at his mercy, how he lasted forever, how you went for seconds with him. What an asshole.
《 Kiss + Making out: 》 Josh doesn’t lean into the kiss so much as freeze in place until it actually happens. He hesitates, brain screaming a thousand possible wrong moves; Is my breath bad? Should I tilt left or right? Until your lips meet his and everything feels right. His hands twitch at his sides, useless, until you reach for one, threading your fingers through his. When your tongue brushes his, every rational thought burns out of him, before clumsily trying to mirror you. He doesn’t think he’s doing it right, not really, but the fact you haven't pulled away yet makes his chest ache with relief. It sinks in he kissed a girl, and he freaks out, because he never thought this would ever happen. By the time you start making out in earnest, his instincts override his paralysis. His hands, trembling at first, find their way to your hips, then to your back, gripping like he’s afraid you’ll vanish. Inside, his head is chaos. She’s letting me touch her. She’s touching me back. Holy shit, I’m kissing a girl, and she’s not laughing at me. Do I taste weird? Am I heavy on top of her? Fuck, I must look ridiculous-no, she pulled me closer, she wants this- When his hand accidentally brushes the curve of your breast over her shirt, he nearly jerks away in apology, but your soft intake of breath roots him in place. That’s when something changes: his touch grows bolder, not smooth but determined.
《 Handjob: 》 Josh's sitting back, but his whole body is tense, like if he realizes even a second, he'll lose control of himself. The first touch makes his breath hitch so sharply he chokes on it. His face burns, and he blurts out: “Wait-uh-are you sure?” even though you're already sure, already moving. Your fist wraps around his dick, slow at first, and his entire body shudders. His eyes squeeze shut. Oh fuck, this is real, she’s really doing this, she’s touching me there. He lets out a low, desperate sound in the back of his throat he didn’t even know he could make. You stroke him just right, and his whole body jerks as he comes undone in your hand, groaning your name so loud he scares himself.
《 Fingering: 》 His hands are trembling before he even touches you. What if I mess this up? What if she thinks I’m gross? But when you guide his hand down and he feels your heat, his brain shorts out. He slips one finger in cautiously, then freezes when you moan. Wait… she likes this? The tension in his shoulders break, replaced by awe. He starts slow, careful, watching her reactions like they’re holy. Inside, he’s gleaming in joy: She’s wet because of me. I’m making her feel this way. That thought nearly makes him dizzy with happiness.
《 Blowjob: 》 He is already apologizing before you even start. “I-I don’t know if you wanna... I mean, I’m not really-oh my God.” His words cut off in a strangled groan as your lips close around him. He freezes, hands hovering awkwardly in the air before he slowly rests them on your shoulders, terrified of messing up the moment. She’s actually doing this. With me. I don’t deserve this. She’s gonna hate it, I’m too heavy, I’m sweating. He bites his lip so hard it almost bleeds, trying not to moan too loudly, but his whole body is trembling. The heat, the suction, the way your tongue flicks at him; it undoes years of insecurity in seconds. The warmth of your tongue around him is too much, he doesn’t want to finish so soon and ruin the moment. He keeps telling himself Star Wars lore in his head to delay it. He is able to delay his orgasm a bit, and when he finally comes, he gasps your name, eyes stinging. He sees you swallowing his load, and he swears he could cry at this small gesture of trust and affection. He turns his head, embarrassed, whispering, “Thank you.” like it’s the sincerest thing he’s ever said.
《 Going down: 》 He tries to approach you in a more logical way, despite being extremely anxious. He is overwhelmed with joy for being chosen for this task and parts your legs gently. He remembers the videos he watched and guides he read on how to give a woman pleasure; he knew someday that knowledge would come in handy. His face is inches away from your vagina, and once he dives in, he finds your smell and taste intoxicating. He starts slow, shyly even, until you grab his hair and pushes him further. He gets the permission to do it really hard then, so he uses his tongues to explore every inch of your parts, and keeps paying attention to the little ways you react, trying to find what works the best for you. He works on you until his jaw is sore. When you come, he is actually surprised he was able to make you come and is proud of himself.
《 The first time: 》 Josh had built sex up in his head as something distant, like a movie scene other people starred in. Something it would never happen to him. In his own mental reel, if it ever happened, it would be clumsy, darkly funny, humiliating. Not this. Not your fingers at the hem of his T-shirt, tugging upward like you actually wanted to see what was underneath.
“You’re shaking.” You told him. He gave a weak laugh. “That obvious?”
“Relax.” You murmured against his jaw, lips brushing his skin. The word hit him like a nerve. Relax. As if he’d ever been able to. He let you lift his shirt off. His first instinct was to cover his stomach, hide the soft fold at his waist, but your eyes weren’t mocking. They were drinking him in.
You liked him, and all of him, which included his body, even if he couldn't love it. He was soft, warm. Hugging him was like hugging a teddy bear, it felt right, it was comforting. You told him he was cute. He snorted bitterly. “Sure. Cute.” As if anyone could love this body.
But then your palms slid across his chest like he was worth touching. The bitterness faltered. His cock stirred in his jeans, betraying him. Holy shit, I'm hard from this??? Don’t look pathetic. Don’t look needy. Please.
You kissed down his neck, nibbling lightly, and his breath hitched. The self-hatred in his head quieted, drowned under a rising tide of want. He clutched at your hips, not knowing where to put his hands, just needing to hold on.
When you opened his jeans, his erection sprang against his boxers. Heat rushed to his face. He wanted to apologize, wanted to explain himself, but you just smiled. your palm brushed over him and he groaned, hips jerking before he could stop himself. Fuck. She’s really doing this. This is real.
You gently kissed him, reassuring him it was fine, he was doing great. You unhooked your bra, and helped him out of his underwear, before asking for a condom. “Y-yeah.” He fumbled for the foil packet on the nightstand. His hands shook so badly he nearly tore it wrong. “Fuck-sorry.” he muttered. “Take your time.” you purred, as you got rid of your panties.
He rolled the condom on, awkward and unpracticed, the latex tight around him. For a heartbeat he stared, dizzy. That’s me. That’s my dick in a condom. It’s real. Holy shit. He looked at you, completely naked, in bliss at your pure beauty. His hands hovered like he wasn’t allowed to touch. “C’mere.” you coaxed, pulling him into a kiss, guiding him to lay over you.
Josh was nervous, afraid of hurting you by laying over you. The moment you guided him between you thighs, he thought his heart would stop. The heat of you gainst his tip made him whimper. He pushed in slowly, terrified of hurting you, terrified of finishing too fast. And then... warmth, wetness, a tightness that swallowed him whole. His head dropped to your shoulder. “Oh my god.” he gasped.
Every inch going inside you felt like a live wire. He clung to you, groaning at each thrust, the old voice in his head still trying to whisper You’re clumsy, You’re gross, She’s pitying you But the way you moaned, the way you pulled him closer, shut those voices up.
He buried his face in your neck, panting, murmuring broken words. “Feels-fuck- feels so good-” His hips stuttered, uneven, every nerve ending on fire. He wanted to hold back, to last, to be good for you, but his body trembled, traitorous, riding the edge.
You cupped his face, whispered, “You’re doing amazing.” and it nearly broke him. No one had ever said that to him. He thrust harder, hips shaking, wanting to believe you, wanting to give you something. When release came it hit like a wave breaking, violent and overwhelming. He groaned into your shoulder, clutching you too tight. His whole body shuddered.
Then he collapsed beside you, sweat cooling on his skin. Hyper-aware of the smell, the mess, the way his stomach folded when he sat up slightly. The condom still on, half-slipping. Every awkward detail screaming at him.
“You’re so quiet.” You said, brushing your fingers along his face. He hesitated. “Just... thinking.” “Don’t think.” you teased gently, kissing him. “Just be here.” The words hit harder than he expected. Josh swallowed, staring at the ceiling. She doesn’t hate me. She stayed. She’s touching me. Slowly, he relaxed into the bed, letting your warmth ease his nerves. His hand hovered, then finally rested on your hip, tentative but sincere. Inside, he admitted something he’d never say out loud: For once, I don’t feel alone. He tells his friends he had sex, he knows Bill will freak out that he did it before him. He spares the details in a way to protect your privacy.
《 Kiss + Making out: 》 He kisses you first, very rough, very sloppy. But it’s not bad, it’s just messy and quickly turns into a raw, addictive rhythm. While kissing, he grabs the back of your head with both hands and moans into your mouth. Afterward, he is happy and relieved to finally have had his first kiss, like a dam of hormones has finally cracked. It seems he was made for make-out sessions. He firmly grips you everywhere, squeezing your thighs and grabbing your waist, smiling into your mouth at each wince of surprise. He has fun exploring, biting your neck and earlobe. He wants to leave a nasty hickey and wouldn’t mind having one too. His hand eventually finds its way under your shirt, and he goes straight for your nipple. He practically humps your leg, not caring how messy it is. He lives for the chaos, for the primal instincts. He hopes you grind back.
《 Handjob: 》 Pete practically salivates when it starts. “Ohhh fuck, finally, babe.” he groans, leaning back with zero shame. He’s loud, dramatic, making comments like: “You’ve got magic hands.” and “Yeah, keep that rhythm.” In his head, he is burning. The thought of your hands around him is extremely stimulating. He thinks: Way better than jerkin' myself off. This is perfect. I could cum just from lookin' at her while she does it. He’s all dirty talk and moans, shamelessly vocal, milking the moment like a porn star. He directly looks you in the eye while you stroke him.
《 Fingering: 》 He's been waiting his whole life for this moment, and he treats it like a mission. Two fingers in, thumb working your clit, like he's seen in porn. He’s grinning smugly the whole time. Hell yeah, porn wasn’t lyin'. I’ve got this. He loves watching your face, loves hearing every wet sound, loves feeling you clench around his fingers. He’s messy but enthusiastic, pumping eagerly, whispering filth in your ear. "C'mon, moan for me, babe." If you squirm or gasp, he doubles down. For him, it’s not just turning you on, it’s proof he’s a goddamn pro (even though it’s literally his first time).
《 Blowjob: 》 The moment you go down on him, he loses his mind. He’s seen it in porn a thousand times, and in his head he knows exactly how it should look. The reality? Way messier, way wetter, and way better. He’s loud, shameless, leaning back with one hand covering his eyes, the other gripping the edge of the mattress. She’s really doin' it-FUCK, it’s wetter than I thought-FUCK, don’t cum yet, don’t cum yet, you idiot! He peeks down at you, sees your lips around him, and almost loses it right there. You wink at him, that mental image of your lips around him will be in his wank bank forever. He’s half trying to enjoy it, half trying not to explode in 30 seconds, trying to remember quotes from movies to help him delay it. “Fuck, careful there, I don’t wanna-” Too late. You swallow his seed with pride; he grabs your chin and tilts your head up: "Good girl." He loved seeing you swallow, he feels like he owns a part of you now and prays you'll swallow everytime.
《 Going down: 》 You open your legs, and invite him in. He dives in immediately, like a man starved. He is just so fucking happy to finally be able to go down on you. It's messy, it's sloppy; he is trying a lot of things at the same time, but he makes up for it with his enthusiasm. He moans against you, half for himself, half because he knows it looks hot. "You taste amazing." He says, while nibbling your thighs. Inside, he’s ecstatic: This is real. I’m tastin' her, makin' her moan. Fuck, it’s better than anything I imagined. You are laughing between gasps, tugging his hair, and he’s eating you out like he’s trying to win a medal. When you come, he wipes his chin and pats himself on the back for a job well done.
《 The first time: 》 Pete had joked about it a million times: "First girl I get, I'm gonna wreck her." He watched too much porn and trained a lot with his right hand, in his mind he'd been ready for sex for years. But now, with your lips pressed to his and your hands tugging at his T-shirt, his swagger doesn’t save him from the punch of nerves that hit the second you pull his T-shirt over his head.
Oh, shit I'm shirtless he panics a little, but he keeps smiling. He's not fat nor thin, just soft in the right places, with tree thin hairs on his chest. He goes for a kiss, you reciprocate while your hands go all over him.
You bit your lip. “You’re cute.” He didn't like to be called cute. He wanted to be hot, dangerous, the monster under the bed. But he kissed you again, rough and sloppy, hands roaming everywhere, because he couldn’t hold back. Your palm brushed over his cock through the fabric, and he groaned, louder than he meant to. His whole body shivered.
Your fingers slid lower, teasing his belt. Pete hissed, grinding against you before he could stop himself. “Damn, babe, you’re really-” His voice broke with a laugh, half horny, half giddy. He was drunk on your warmth, your smell, the way you let him touch you. When you shoved his jeans down, leaving him in just his boxers, he felt his erection straining, painfully obvious. He swallowed and joked, “Ya like whatcha seein', huh?” because he couldn’t stand the silence of being looked at.
You smile at him, and place his hands on the back of your bra. As he unhooks it, you help him out of his boxer, fully freeing him. You lay on your back, and point to a condom on the nightstand.
"Yeah, yeah." He stammered, reaching for the prize. His hands shook as he tore at the foil. The wrapper ripped jagged, almost snapping the rubber inside. “Crap- wait, I got it, I got it.” he muttered, laughing nervously. His cock twitched in his fist as he rolled the condom on, snug and almost surreal.
You stripped out of your panties, and Pete had his eyes locked on you. "B-babe, you're so fuckin' hot." He managed to say, as you guided him to lay over you. Pete grinned; he liked the show of power, but inside his heart was sprinting. Your hands slid over his back, squeezing, as he lined up, nudged forward and went in.
The second he thrusts into you, he lets a loud "FUCK!" out. Nothing could've prepared him for this sea of emotions. His eyes wide, brain blanked out; white noise filling his skull as tight, wet heat swallowed him whole. He twitched over you, bucking, unable to control his hips.
“Fuck, I’m inside you.” he moaned, voice cracking. He lets his body fall over yours and kissed you everywhere he could reach: mouth, neck, shoulders, sloppy and desperate. His tongue dragged over your collarbone, leaving wet marks. Finally, Pete’s teeth sink into your shoulder as he pounds into you, and he can’t help but snarl when you yelp. Mine. I’m leavin' proof. I want her covered in me. He smirks at the thought of you seeing yourself in the mirror tomorrow, marked like prey. He wants you to know how good you made him feel.
Every move you made milked more gasps from him. He tried to thrust up in rhythm, but his excitement broke it into messy, uneven jerks. He wanted to last, wanted to make you cry out, but he was already on the edge, the intensity too much. You reach for his neck, and bite him. Leaving marks, as you sunk your nails on his back again.
“I can’t-fuck-I’m gonna-” His words spilled before he could bite them back. He groaned, bucking wildly as he came, clutching your body to his like he could fuse them together. When it was over, he flopped back onto the mattress, sweaty hair plastered to his forehead, panting. He laughed, breathless, because he couldn’t stop himself. “Damn, babe. You're goin' to be the death of me.”
You tuck yourself into his side, stroking his hair, smiling. Pete threw an arm around you without thinking, grinning like a fool. He kissed your forehead, then your nose, then your lips again, greedy even in exhaustion. Inside, he was ecstatic. Finally. Finally got to do it for real. And it wasn’t gross, or weird, or disappointing, it was fun. Hot. Better than any porn I’ve ever seen.
He trailed his fingertips down your back, playful even now. “Round two later? Or three, or four or five? I mean, I ain’t sayin’ I could keep up, but I will gladly die tryin’.” You smacked his chest lightly, laughing. Pete laughed with you, too warm to care. In the back of his mind, he swore he’d make every time after this just as good for both of you. He'd tell his friends later that he finally did it for real, and would show the scratches on his back and hickeys on his neck as proof.
《 Kiss + Making out: 》 His first kiss comes naturally, awkward but gentle. He opens his mouth carefully, and once he feels your tongue, he reciprocates, mimicking your movements. Once the kiss deepens, he feels comfortable enough to put his hand on the back of your head. When it sinks in that kissed a girl, he freezes, his face red as a strawberry. Once he enters make-out territory, he gets lost in it. He pulls you closer and melts at the warmth of your body. Eager to learn what you like, he kisses your neck and immediately offers his to be kissed in return. He uses his hands to explore your back and eventually finds his way under your shirt, but asks first if it’s okay between kisses. He eventually buries his face between your breasts while kissing your collarbone, and he places your hand over the bulge growing inside his pants.
《 Handjob: 》 The second your hand wraps around his dick, he groans, deep and unashamed. His mind races: She wants me. She’s doing this for me. He can’t stop himself from thanking you between gasps. Every squeeze makes his hips jerk. Fuck, it’s so nice. I could come just from this. He’s sweet about it, but also way too needy, gripping your wrist gently, redirecting you to do it the way he usually does it to himself.
《 Fingering: 》 He is careful, reverent almost. His fingers start tentative, testing your reactions, brushing your lips, circling you slowly. Fuck, she’s so soft… she’s letting me do this. Every moan you make is like fuel to his confidence. By the time he slips inside, he’s biting his lip, nearly as turned on as you are. He finds your warmth and moisture very nice, different and exciting. He keeps murmuring, “Is this good? Tell me what you like.” desperate to get it right. When you arch into his hand, he feels like the luckiest bastard alive.
《 Blowjob: 》 He is on his back, his hands nervously grab the sheets. “You don’t... you don’t have to this if- AH!” His voice breaks the instant you take his dick in. He looks at your face as you lick his length, and grabs your hair. Not to bury you deeper, but to stroke it. She wants to do this for me? Oh, she feels amazing, it’s so soft, so warm. I’m gonna lose it. His hips jerk despite trying to control, while you mumble in a way to tell him it's okay. He keeps thinking about different ways to build mana curves to avoid coming too fast. When he finishes, he’d immediately feel guilty for not giving back, but thinks you swallowing his load is a great way to show him trust. "Ah... Y-you didn't need to do that for me, you could've spat it out..." But he's so glad you did, he thinks it's so hot that a part of him is inside you. He wants to come on your face next time.
《 Going down: 》 He takes a good look at you while controlling his urges inside. He just wants to sink himself in you, but he has restraints to do the deed diligently. He kisses you along your stomach then goes for your thighs, savoring every moment, adjusting when you gasp louder. He goes for your clit and is instantly addicted to your smell and taste. He likes when you grab his hair, pulling his face closer to your core, and gets hard knowing he is doing a good job. His thoughts are a blur of devotion and perversion, he wants to memorize every reaction, he wants to keep his mouth there until you are shaking. When you come, he shines against your skin, dick aching just from how turned on he gets from your pleasure alone. He wears your fluids on his face as a medal of honor.
《 The first time: 》 He thought about this moment a thousand times, usually at night, under his blanket, hand working desperately while his brain made up half-believable scenarios. But no fantasy could've prepared him for how real it feels.
He is over you, on your bed, hello kitty sheets smelling faintly of fabric softener. You're on your underwear, your breath warm on his lips, your hand tugging his T-shirt higher and higher. Until you command him to take it off. He swallowed dry, shy and self-conscious. He pulled the shirt over his head, and exposes his chest to you. Pale, full of freckles, so lean you can feel his ribs when touching him. His red face gave away his embarrassment, bracing himself for a look of mockery on your face. Instead, you touch his chest and traces your fingers over him, smiling, like you found something you wanted to keep.
What..!?! She likes it?!? She actually likes me like this?!? He thinks nervously, not long enough before you bring him to a kiss again, kissing down his collarbone, tongue mapping all of his skin. He hesitated a bit before touching you, but his hands go on your waist, before he slides them up, over your bra.
You grin at him, lean back and unhooks your bra, tossing it aside. His dick twitched painfully inside his pants, he wanted to look away and be polite but his eyes drank you in. Your breasts, skin, curves. His brain split between don't stare too hard and fuck I get to touch her. You tease him, tugging at his belt.
His hands shook as he fumbled it open, and you helped him push his jeans down. When his boxers followed, his face went crimson, his erection free, hard and flushed. Pointing at you like a confession.
You smile at him. "You are really ready, huh?" Jerry wanted to melt into the floor. Of course I am, I've been hard since I sat on your bed. He managed to say only a mumbled "Yeah." You kiss him again, pushing him back over you, straddling his lap. His hands clutch at your hips instinctively, your heat pressed against his cock trough your panties making him almost lose it already.
"Condom." You tell him. "Oh, yeah, yeah, right." Jerry scrambled, reaching for his wallet on the nightstand. He tore the packet too fast, almost ripping the rubber itself. He pinched and rolled it down his length, the feeling made his whole body tense. This is it. This is really happening.
When he looked at you, you were shimmying out of your panties. You spread your thighs, guiding him closer. His heart pounded so hard it hurt. "Relax." You say, kissing him again. He nodded but his body wasn't listening anymore. Every nerve screamed. His dick ached, he lined up, nudged forward and slid in.
The heat and tightness almost ended him. He gasped into your mouth clinging at your lips like a lifeline. "Oh God." You moaned softly, arching against him. He froze, terrified. "D-did I hurt you?!?"
"No". You reassured him. "Keep going, don't stop." Relief crashed through him, soon replaced by hunger. He thrusts into you again, slow, shaky then deeper. His body knew before his brain did. His skin buzzing when your nails dig through his back. His forehead meets yours. She feels so good... He tries to match your rhythm, hyper-focused on every twitch and gasp you make. For him, it’s less about his pleasure and more about the intimacy, driving himself into you feels like home.
He dissolved under the flood of sensation. He kissed you desperately, tongue clumsy, hands roaming over your back, your waist, your breasts. He wanted to touch everywhere at once, memorize every inch. You whisper his name, he groaned, thrusts quickening. His cock pulsed inside you, the condom the only thing keeping him grounded. Each squeeze around him sent sparks up his spine.
Fuck fuck fuck fuck I'm gonna cum I can't stop. "Jerry..." You gasp, and that was it. His body seized, ecstasy ripping through him. He buried his face against your neck, moaning helplessly as he spilled into the condom, hips jerking in broken rhythm. When it was over, he collapsed back against the sheets, chest heaving, sweat slicking his skin. His arms were still around you, unwilling to let go, tightened around your waist. He wanted to say everything at once: how beautiful you looked, how unreal it felt, how he didn’t deserve you.
He kissed your temple, whispering, “Thanks...” before he even realized he’d said it. His throat was too thick with emotion for much else. You laughed gently, patting his chest with lazy fingers. “You’re welcome.” He flushed, but didn’t care. Laying there, sweaty and spent, Jerry finally believed it: he wasn’t broken, wasn’t unworthy. Someone wanted him, wanted this. And as his body slowly calmed, another thought bubbled up: If it always feels this good to be with her, I’ll never want to stop. He doesn’t tell any of his friends that he lost his virginity, thinks it’s weird to talk about sex with them. It’s cooler to keep this between the two of you.
