Zach Dempsey - Blog Posts

wishyouloveme

2 months ago

The first time 18+

Song rec: Birthday cake (Rihanna)

Warnings: Smut, Eating out, swearing, inexperienced reader, sort of experienced (?) Zach, Reassurance, Insecurity, SPOILERS, sheltered reader.

A/N Note: Hey lovelies!! First time writing for Zach, so I hope it's good. Minors DNI!!! Xoxo, asks are always open <3 Also, somehow this short one shot turned into over 2,500 words??

Further links: main blog

Pairing: Zachary “Zach” Shan-Yung Dempsey

Further information: Request by 🪷anon (request here) Timeline is after Hannah died, before Tony leaks the tapes.

Tag list: @boundbyeclipse @bloodlinemadness

“Have you ever been with someone?” You turned your head, seeing your boyfriend, your very shy, very gentle boyfriend, fiddling with his jacket sleeves. Despite what everyone thinks due to him being in with Bryce, He was very...non-problematic when it came to you.

“Babe, please tell me you didn’t hit your head. I’ve been with you” You chuckled out,totally missing the fact he meant sexually. You’ve been with him, mentally, and physically, just not sexually. The farthest you two have ever gone is making out at one of Bryce’s parties, and grabbing each other from over your clothes, before he was pulled away to play beer pong by Bryce and Montgomery “I didn’t mean like that” He let out a quiet laugh, looking at you “I meant like…Have you ever been with someone sexually?” The meaning hit you so fast it made your head spin, and you felt the heat rush between your legs the second the blush hit your face. “Oh!” You considered lying to him, knowing he was at least somewhat experienced, having been with Hannah over the summer before she committed, before you decided otherwise.

“No” Expecting the embarrassment to hit, you looked away. But it never came. Zach had made you so comfortable about being around him and being with him, that you didn’t feel embarrassed in your answer. When you finally looked back, He was watching you with love in his eyes. “Do you ever want to be?” His question shouldn’t have surprised you, since he was always so focused on what you wanted, but it still did. Most boys would have just assumed that was their go ahead to try and have sex.

“I think so. At least, one of these days.Sometimes I wish it wasn’t something I was judged for, y’know? Like, sometimes it feels like there's a giant flashing sign over my head saying virgin, and it doesn’t feel good. Especially when there's guys like Bryce in our school, or Justin who claim to be so experienced, it's just-” You go off on a tangent, not even realizing you’re doing it, it just comes spilling out. He could tell it annoyed you how your school was so over sexualized. You pause in the tangent when you see him moving closer to you, despite the bed being small enough that you were touching legs almost the whole time. He grabs your face as carefully as he could and pulls you into a kiss, and not just one of those small pecks when one of you wants the other to be quiet. No, this was a fucking soul snatching kiss. You kiss him back, your hands automatically going to his chest like you had done this a million times. You hadn’t, but your brain didn’t need to be experienced to figure out you wanted him close. You are anything but happy when he pulls away from the kiss, so you lean up again and kiss him. He lets out a shaky groan into the kiss the minute you grab at his hair, and he pushes his hand from your face down to your thigh, gently pulling you up and onto his lap. Despite being nervous about going further with him, you felt like this was exactly where you needed to be. In his arms, feeling him beside you, it just felt right. He carefully brings his other hand into the mix, cupping your cheek as his hand that was on your thigh slides under the hem of your shirt, just caressing the side of your stomach. He knew you were nervous about going further, since you don’t hide it very well, So until you said the word, he was content to just stay like this. You pushed at his chest a little as you moved back, chewing on your lip until you just decided to say what's on your mind. “I don’t wanna have sex tonight” You admit, despite your hand’s having minds of their own and going under his shirt to press into the abs and the muscles under it, the muscles that had to have been made by a Greek god, otherwise it was impossible.

“That's okay, we don’t need to” He promises with a gentle kiss to your jaw, just gently dragging his nose down your neck, leaving a few gentle kisses there. He wasn’t pushing, he never pushed. He was just making sure you knew he loved you, and would be okay to do whatever. If you wanted sex, great. If you didn’t, he was content with just sitting here with your freezing cold hands on his abdomen. “Is there…something else we can do?” You ask, unconsciously licking your lips as you carefully bring a hand out from under his shirt to run it through his hair.

“Well that depends.” He replied in a slow drawl. His head tipped back a little as your fingers ran through the silky threads. He knew you loved his hair, but hadn’t known the extent of it until you two had started dating. Now, you practically always had one hand in his hair. “On what?” You said, almost losing your breath in that second due to how strikingly handsome he looked. “On whether you wanna be sexual, or you wanna just hang out” Losing the confidence you barely possessed wasn’t something lost on him, and wasn’t something new to you. You get off his lap, trying to ignore the look on his face. “We should just….I don’t know. Relax, maybe?” He could tell that you wanted him. He knew he wanted you. But he could also tell something was holding you back on this. “Baby” He grabs your warm, tugging you back and onto his lap, trapping you with his arms in case you try to get up again. “I don’t know where this shit is coming from, but shut it out” His stern voice brought you back, even though you didn’t like the situation, He was one of the ebay people to come back to from it. “I’m sorry” You say quietly, knowing he hates when you say that, but you can’t help it. “Don’t. Stop that. Stop apologizing for thinking you’ve hurt my feelings” He says, kissing your forehead, and exhaling into your hair. “Being with you, no matter how, is the best fucking part of my life. So never apologize for it” That. That right there is when you made the decision in your head that this man would be the first of everything, he’d already been your first kiss, been your first make out session. “What else is there to try sexually? Other than…y’know..actual sex?” Came your small response. He let out a small chuckle as he kissed above your ear. “There's a lot. Mostly oral, but there's other things.” He says, almost like he was educating a child, but he didn’t have the condescending tone in his voice like most would. “Tell me” You say softly, rubbing circles into his arm. You didn’t have much knowledge, Even though you pretended to at school, this was as new to you as it could be. You had imagined a million different things, and it never came to this. This conversation. The conversation that should feel degrading, that should feel embarrassing. But somehow, with him, it doesn’t. It shouldn’t surprise you, because nothing with him ever is, but he often managed to still surprise you. “Well, I wanna do something. I promise it won’t be sex, but I want you to trust me, yeah?” He says into your ear, a low undertone in his voice that makes you shiver, your thighs struggling to close around his hips. “Okay” You agreed, a small tremble to your voice at the idea of what's gonna happen.

“Take off your clothes baby” He said slowly, his eyes scanning over your body. Despite the tension in the room, his touch on your thighs was gentle, the rubbing on the inside of them reminding you he was right there, and he wouldn’t let you fall into another overthinking episode. Your mind spiraled, down, down, down into the pit it’s known for so long. The familiarity and the suffocating all enveloped you in one. The idea of him not liking your body, the thought of how he would react to you naked, despite his constant compliments about how fucking beautiful he found you. All of it closed in at once, and while it was comforting to be back in a place you knew all too well, It scared you. Because as wrong as you might be, you could also be-. “Stop it” His voice snapped through all those words like he was shattering glass with a bullet. “I don’t care what the fuck your head is telling you. You’re perfect. It’s not a guess, it’s not a thought, It’s a fact. Now stand up and get undressed so I can show you just how perfect you are.” You exhaled a small shaky breath as his hands left your thigh, the small feeling leaving, and you hated the cold feeling it brought on. “Babe. If you aren’t comfortable with this, just tell me. I’m not gonna get upset.” He promises gently, cupping your face. “I wanna do this, I just ... .What if you don’t like me anymore after?” Came the anxious thoughts, all spilling out like a puddle into the open, and that was terrifying. Because now he knew. He knew the thing you had been hidin-. “That is like someone saying a typing monkey is gonna be the next shakespeare. It’s impossible. Now. Do you wanna do this, or no?” “Yes!” Came a stubborn reply, before you even had time to think about it. You pushed yourself off of his lap before your brain had time to process your actions, because the minute you started to think about this your brain will fuck you over. It’s the equivalent of saying Karma will always and forever be a bitch. It’s a fact that has been proven. You pull off your top, exhaling gently. You had never let him see your stomach. You shake off that thought and the small voice in the back of your head, and you reach for the jeans you had been wearing, pulling those down after you’ve undone them, too. Standing in your bra and black underwear, you felt genuinely stupid. How would he, Zach fucking Dempsey, be attracted to this? “I said, all of your clothes, pretty girl” The nickname seemed to roll off his tongue so naturally, that it had your brain short circuit. All you could do was nod, and reach up to take off your bra with shaking hands. Letting the bra slip through your fingers and fall to the floor, you made yourself busy taking off your underwear before your brain could react to the fact you were standing naked, in a room, alone with Zach Dempsey.

Slipping the underwear down your legs, a million thoughts ran through your head, none particularly likeable. Certain ones jump out ‘why couldn’t I have shaved before he came over today’ or ‘why aren’t I making this more sexy? He’s probably getting bored’. One glance down at his lap diminished the last thought. There was a noticeable bump in his jeans, and you might be insecure but you weren’t dumb. He was attracted to you. Why? You didn’t know. “Fuck” He said, his tone lazy as your panties hit the floor. “Do a spin for me, pretty” Complying, you do a small spin, hands pointed to the ground. “Jesus” You smile a little, feeling a rush to your head at the idea of him actually liking you. His reaction alone told you he wasn’t faking, and if his reaction didn’t, his boner definitely did. “On the bed baby” He exhales out, looking you up and down, but his eyes weren’t focused on your tits or anything sexual. His eyes were focused on your face, and his eyes were dark. You bite your bottom lip, thinking of disobeying but knowing you would regret it later, so you slowly move, getting on the bed. He watches you for a second before he pulls off his shirt, the belt going too but the pants didn’t. You admired the jeans that now hung low on his lips, letting a peak of his happy trail out as he climbed back onto the bed and over you. He kisses you, his hand going to hold your face, his other hand going to rest on your stomach, just feeling at the smooth skin. He’d done it before, when you guys were cuddling or when you were kissing and he wanted to feel some part of your skin. But this was different. It wasn’t the fact you were naked beneath him, which he’d imagined a million times, but it never compared to the real thing. No, it was the fact you now fully trusted him. He knew you liked to take the safe route all the time, so the fact you trusted him enough to not just say ‘let's just watch a movie’, but you went down the unknown road with him, He knew you trusted him. He chuckles into your mouth when you tug at his hair, obviously getting a little impatient. “Relax, pretty girl. I’ve got you” He mutters as he pulls away, kissing at your collarbone, his hand sliding down your body to rest at your thighs. “Open for me, baby” He purrs out, kissing down your body, kissing your boobs gently. You do just that, your thighs falling open like he had said a magic word. “Good girl” He cooes out, his voice soft and loving. He lets his body settle between your legs, his mouth paying attention to your boobs. He runs a finger over your right nipple, kissing at your left. “You’re so pretty. So fucking perfect” He groans out before he takes your nipple into his mouth, gently sucking. You let out a gentle sigh, your head falling back onto your black pillows, your hand going into his hair. If this is what you were missing with sex, it felt pretty fucking good.

He grins against your nipple, biting it gently before he switches, lavishing your other nipple with the same attention. He kisses down your stomach, pausing to gently lick at your stomach. “Fucking love this stomach. You’re so beautiful. Fuckin’ knew you were perfect. My perfect girl, hm?” It was a rhetorical question. You knew that. He kisses at your left him before he moves down, his hands splaying over your thighs. “Jesus baby” He exhales out as he sees your pretty pussy. You were so wet, but so fucking perfect. He ignores it for now, although it’s very tempting to just fucking eat you out on the spot. He leans down, kissing your right thigh, pushing him down on the bed. Your hands on his shoulders, and you whined a little when he was getting too far for you to reach him. “I know baby, It’s okay, I’m right here” He cooes out to you, kissing at your knee before he moves back up, knowing you craved the physical touch. You gently bury a hand in his hair, being careful to not scratch at his scalp, even though you’re pretty sure he would love it if you did. Finally, he couldn’t hold himself back, and he gently rubs at your pussy, hissing out at how wet you are. “Shit baby, so fuckin’ perfect for me. All for me” He groans out softly, feeling his dick strain against his zipper. “I love you” You mumble in between soft moans at the feeling, because holy shit. How was he so good at this? Oh right. Hannah. Hannah Baker. He could tell almost immediately when you slipped back into your mind, and he leans down, running his tongue over your clit. “Come back baby, come back” He says against your pussy, making you let out a squeak at the suddenness but gently moan at the feeling, your hips pressing down into his mouth. “Shit” You exhale out, a sound of content mixed with pleasure rather than just pleasure.

“There's my pretty girl. Hi baby” He hums, gently running his tongue up and down your pussy, his tongue circling your clit. You let out a low moan, your hand tightening in his hair, and, accidentally, scratching at his scalp. He lets out a groan, the vibrations making you gasp and cover your mouth with your unoccupied hand. “Oh shit. So that's what you like, hey baby?” He purrs out, and gently pushes his tongue into you, making you clench down a little at the feeling. “Shit. Now i know this is all for me” He cooes out, gently rubbing at your entrance with his finger after he pulls his tongue out. He just prods, never penetrating, since you had made it clear you didn’t want anything close to actual sex. His finger was just there with the possibility, knowing it felt good to barely push. “Fuck Zach” You whimpered out, tugging at his hair. It felt so good, and you were starting to feel a pressure in your stomach. “Yeah baby? What's up pretty?” He hums out, gently biting down on your clit. You saw stars on the back of your eyelids as your eyes snapped shut at the feeling, your hips flinching up at least a good inch from the bed. “Feels weird” You managed to moan out, exhaling shakily as you moan. “What does?” His mouth stops, making you whine out in protest as you tug at his hair. “Stomach, shit, please don’t stop” You beg out softly.

Rather than answering you verbally, he leans down and goes back to licking and sucking. Your breath hitches as your hand clenched in his hair, your hips arching up as you came. He pulled away after a minute, smirking as he swallowed. “Fucking amazing. You’re so perfect baby”.