First Everything (Ellie & Jacob - Book 1)
Copyright© 2025 by Taylor Darkwood
Chapter 1: A Nervous Conversation
Erotica Sex Story: Chapter 1: A Nervous Conversation - Two virgins. One library. Zero idea what they're doing. Ellie and Jacob's first time is just the beginning of an explicit journey through sexual discovery: from fumbling failures to complete intimacy. This is realistic erotic romance where the sex is detailed, the communication is awkward, and the love is real. Book 1 of 3. All books written and available on ZBookStore shortly.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Anal Sex Exhibitionism First Facial Safe Sex Tit-Fucking
The coffee table held the remnants of Thai takeout neither of them had finished—pad thai cooling in its container, spring rolls picked at but abandoned. Ellie sat on one end of Jacob’s thrift-store couch, her legs tucked under her, wearing the oversized cardigan that made her feel safe and the jeans that actually fit her hips without gaping at the waist. Rain drummed against the window behind them, Seattle doing what Seattle did best in November. The apartment smelled like lemongrass from dinner and the sandalwood candle Jacob’s roommate had left burning before disappearing for the weekend.
That disappearance hadn’t been accidental. They’d planned this—not explicitly, but in the way couples did when they’d been dating for eight months and kept stopping themselves at the same point, kept pulling back before things went further, kept saying “not yet” until “not yet” started feeling more like fear than caution.
Jacob sat on the other end of the couch, his long legs stretched out, one foot bouncing slightly. He wore the faded Modest Mouse shirt she’d once borrowed, sweatpants that hung low on his narrow hips. His dark hair fell across his forehead, and he kept pushing it back only for it to immediately flop down again.
She’s been quiet for ten minutes and I don’t know if that means she’s changed her mind or if she’s just thinking and fuck, why is this so hard, we’ve talked about it, we both said we wanted to, but talking about it and actually doing it are completely different things—
“Do you want to watch something?” Ellie asked, her voice softer than usual, and Jacob recognized the tone as the one she used when she was offering an out, a way to pretend they weren’t both thinking about the same thing.
“We could,” he said, which wasn’t yes or no, which was safe.
Ellie picked at a thread on her cardigan sleeve. Outside, a car alarm briefly wailed before cutting off. The building’s heating system clanked somewhere in the walls. She could feel her heartbeat in her throat, that anxious flutter that made her want to simultaneously jump off a bridge and hide under blankets.
He’s going to think I’m backing out. Maybe I am backing out. No, I’m not, I want this, I want him, I’ve wanted this for months but Jesus Christ actually doing it is different than thinking about doing it in the shower where everything feels easy and uncomplicated—
“Or we could...” Jacob started, then stopped, his foot bouncing faster.
Ellie looked at him, really looked at him, and saw the same nervousness reflected in the way he held his shoulders, the way his fingers drummed against his thigh. That helped somehow—knowing he was just as terrified as she was.
“We could go to your room,” she finished for him, her voice barely above a whisper.
Jacob’s foot stopped bouncing. “Yeah. We could do that.”
Neither of them moved for a long moment. Then Ellie stood, and Jacob stood, and they navigated the small apartment like they were walking through a dream, hyper-aware of every step, every breath. His room was at the end of the short hallway—door half-open, string lights he’d hung at Ellie’s suggestion casting everything in warm amber.
The room smelled like him, that specific combination of Old Spice deodorant and the mint chapstick he was addicted to and something else that was just Jacob, something she’d come to associate with safety. His bed was made—he’d made it this morning, she realized, which meant he’d been thinking about this too, planning for it, hoping for it.
They stood beside the bed, both suddenly aware of how momentous this was supposed to be, how it carried weight that neither of them had asked for but couldn’t shake. Ellie’s hands found the hem of her cardigan, fingers working the fabric.
“I’m nervous,” she said, because saying it out loud felt better than letting it sit in her chest.
“Me too.” Jacob’s voice cracked slightly on “too,” which would have been funny in any other context. He reached for her hand, threading their fingers together. His palm was slightly sweaty, and that was comforting in a weird way—proof that his body was as amped up on adrenaline as hers. “We don’t have to—”
“I want to,” Ellie interrupted, squeezing his hand. “I’m nervous but I want to. Both things can be true.”
God, she’s perfect, how is she perfect, how did I end up with someone who gets scared but does things anyway, who’s honest about being scared instead of pretending—
Jacob kissed her then, pulling her closer, and kissing was familiar territory at least. They’d been making out for months, knew the rhythm of each other’s mouths, knew that Ellie liked when he bit her lower lip gently and Jacob melted when she ran her fingers through his hair. This kiss was different though—slower, more deliberate, carrying the weight of what came next.
Ellie’s cardigan hit the floor, and then Jacob was pulling his shirt over his head, revealing the lean torso she’d felt through fabric but never seen fully. He was pale, a small constellation of moles across his left shoulder, the faint outline of ribs visible beneath skin. She ran her hand across his chest, feeling the rapid thump of his heart, and he shivered at her touch.
“Your hands are cold,” he murmured against her mouth.
“Sorry.”
“Don’t be.” His fingers found the hem of her shirt, hesitated. “Can I?”
Ellie nodded, raising her arms, and Jacob pulled the fabric up and off. She’d worn the nice bra—black lace from Target, nothing fancy but better than the sports bras she usually lived in. She fought the urge to cross her arms over her stomach, over the soft curve of her belly that romance novels never mentioned and Instagram filtered away.
He’s looking at me and I want to hide but also I want him to keep looking, want him to want me the way I am, want this to be okay—
“You’re beautiful,” Jacob said, and his voice carried such genuine awe that Ellie felt tears prick her eyes for reasons she couldn’t fully articulate.
They moved to the bed, crawling onto the mattress that was too small for two people but would have to work. The sheets were navy blue, soft from being washed too many times. Ellie lay back against the pillow, and Jacob settled beside her, half-covering her body with his, still kissing her like if he stopped the spell might break.
His hand explored her side, following the curve from ribs to waist to hip, learning the landscape of her body. When his fingers brushed the underside of her breast through lace, they both inhaled sharply. He did it again, more deliberately, and Ellie arched slightly into the touch.
“Can I take this off?” His fingers hooked the edge of her bra, and Ellie nodded, sitting up enough for him to reach the clasp. He fumbled with it, couldn’t get it to release, tried again. “How do these ... there’s no ... fuck—”
“It’s okay,” Ellie reached back, undid it herself with practiced ease, let the straps slide down her arms.
And then she was topless in front of another person for the first time in her life, and Jacob was staring at her breasts like they were holy relics, and she didn’t know whether to laugh or cry or cover herself.
Don’t overthink this don’t overthink this don’t—
Jacob’s mouth found her nipple, and suddenly overthinking became impossible because oh, oh that felt—his tongue circled the sensitive skin, lips closing around it, and Ellie made a sound she’d never heard herself make before, something between a gasp and a whimper.
“Was that okay?” Jacob pulled back immediately, concerned.
“Yes,” Ellie managed, her hand going to his hair, guiding him back. “Very okay.”
He continued his exploration, alternating between breasts, learning what made her breath hitch, what made her fingers tighten in his hair. Ellie’s hands wandered too, tracing the planes of his back, feeling muscles shift beneath skin. When she reached the waistband of his sweatpants, she hesitated.
“Can I?”
“Yeah. Yes. Please.”
She pushed the fabric down, and Jacob kicked the sweatpants off the end of the bed. He wore boxer briefs, gray with a small hole near the elastic that he probably didn’t know was there, and she could see the outline of his erection straining against the fabric. Seeing it made it real—made what they were about to do feel imminent rather than theoretical.
Jacob’s hands found the button of her jeans, worked it open, dragged the zipper down tooth by tooth. “Lift up?”
Ellie raised her hips, and he tugged the denim down her legs, taking her socks with it in a practical move that made her love him even more. Her underwear was basic cotton, Thursday printed on the waistband because she bought in packs of seven and never paid attention to which day she was wearing, and she felt a flash of embarrassment before remembering that Jacob had a hole in his boxer briefs, that they were both just people with regular underwear and regular bodies about to do something that felt anything but regular.
They lay facing each other now, mostly naked, close enough that she could feel the heat radiating off his skin. Rain still pattered against the window. String lights cast shifting shadows across his face.
“I don’t really know what I’m doing,” Jacob admitted, his hand resting on her hip, thumb rubbing slow circles against skin.
“Me neither.” Ellie kissed him again, tasting mint chapstick and Thai food and nervousness. “We’ll figure it out.”
Together. We’ll figure it out together. That’s what this is supposed to be—figuring it out together instead of one person knowing and the other person following—
Jacob’s hand slid from her hip to her thigh, up and then down again, not quite reaching where she wanted him to touch but getting closer with each pass. When his fingers finally brushed over cotton, over the heat between her legs, Ellie’s hips jerked involuntarily.
“Is this okay?”
“Mmhmm.” She couldn’t form actual words right now, not with his fingers moving against fabric, applying pressure that wasn’t quite enough and too much simultaneously.
He pushed her underwear aside, and then his fingers were touching bare skin, slipping between folds, exploring with the tentative curiosity of someone reading a map in a foreign language. He was too high, too light, then too rough, trying different pressures and locations to see what worked.
“There,” Ellie gasped when he accidentally brushed her clit, and Jacob focused his attention there, circling the sensitive bundle of nerves with more confidence now that he had direction.
Ellie reached for him in return, slipping her hand inside his boxer briefs, fingers wrapping around heated flesh for the first time. Jacob groaned—actually groaned, a sound from deep in his chest—and his hips thrust into her grip involuntarily.
“Fuuuck,” he breathed, the word drawn out and shaky.
She stroked experimentally, learning the weight of him, the texture, the way his cock pulsed in her hand. Jacob’s breathing went ragged against her neck, his fingers losing their rhythm on her clit as he got lost in his own sensation.
“Wait, wait,” he gasped suddenly, catching her wrist. “If you keep doing that I’m going to come and I want ... I want to be inside you when that happens.”
Ellie’s stomach flipped at the words, at the directness of them. “Okay. Yeah. Okay.”
Jacob sat up, fishing in the drawer of his nightstand for a condom—one of the ones they’d bought together two weeks ago at Target, both of them blushing in the family planning aisle, neither of them acknowledging what buying condoms meant they were planning. He tore the package open, then stared at the latex like it might bite him.
“Do you know how to...?”
“I watched a video,” Jacob admitted, which was so endearingly him that Ellie felt a surge of affection strong enough to ache. “But watching a video and actually doing it are probably different.”
He rolled it on—backwards first, then correcting with fumbling fingers—and Ellie wiggled out of her Thursday underwear, kicking it somewhere toward the end of the bed. Naked. They were both completely naked now, no more barriers between them except fear and inexperience and the mutual understanding that what they were about to do would change things, would cross a line that couldn’t be uncrossed.
This is it this is actually it and I want this I really do want this even though I’m scared because being scared and wanting something aren’t mutually exclusive and he’s looking at me like I’m precious, like I matter, and that’s worth everything—
Jacob moved between her legs, positioning himself. “How should we...?”
“Like this is good,” Ellie said, spreading her thighs wider, trying to remember everything she’d read in those romance novels, trying not to think about how exposed she was right now, how vulnerable. “Just ... go slow?”
He nodded, bracing himself on his forearms on either side of her head, and she could feel him pressing against her entrance, hot and hard and insistent. He pushed forward experimentally, and it didn’t work—the angle was wrong, or maybe she wasn’t relaxed enough, but his cock just sort of pressed against her without going in.
“Sorry, let me—” Ellie reached down, guiding him, angling her hips differently.
He tried again, and this time the head of his cock breached her entrance, and oh—
“Ow,” Ellie gasped, because it hurt, not terribly but enough that her body tensed, trying to reject the intrusion.
Jacob froze immediately. “Shit, should I stop? Do you want to stop?”
“No, just ... give me a second.” She breathed through the initial burning sensation, willing her muscles to relax, reminding herself that this was supposed to hurt a little the first time, that she’d known this going in. “Okay. Keep going. Slow.”
He pushed further, inch by careful inch, and Ellie felt the stretch of it, the uncomfortable fullness of having something inside her body that had never been there before. It wasn’t like the romance novels—there was no sudden flash of pleasure overriding the pain, no perfect moment where discomfort transformed into ecstasy. It just hurt, and felt weird, and was somehow still meaningful despite those things.
“You okay?” Jacob’s voice was strained, his whole body rigid with the effort of going slow, of not just thrusting like his body clearly wanted to.
“Yeah. Are you?”
“I’m inside you,” he said, wonder evident in his voice despite the awkward circumstances. “I’m actually inside you.”
Holy shit I’m inside her, this is real, this is happening, she’s so tight it’s almost painful and hot and wet and I’m trying so hard not to move too fast, not to fuck this up—
He started moving—shallow thrusts at first, barely pulling out before pushing back in. Ellie wrapped her legs around his waist, trying to find an angle that felt less uncomfortable and more like what sex was supposed to feel like. Her body was adjusting, the pain fading to something more tolerable, though “pleasure” still felt like an overstatement.
Jacob’s rhythm was unsteady, sometimes too fast, sometimes losing the angle entirely and slipping out before fumbling to push back in. Sweat beaded on his forehead, his arms shaking with the effort of holding himself up, and Ellie could see the concentration on his face, the determination to make this good for both of them even though neither of them really knew what they were doing.
“You can go harder,” she said, because watching him hold back seemed worse than whatever discomfort might come from him letting go.
Permission granted, Jacob’s hips snapped forward with more force, and Ellie gasped—not entirely from pain this time, something else threading through the sensation, something that might eventually become pleasure if they kept doing this. She rocked up to meet his thrusts, trying to find the rhythm, trying to make her body work with his instead of against it.
“Oh fuck, Ellie, I’m—” Jacob’s warning came too late. His body went rigid, hips jerking erratically, a choked sound escaping his throat as he came inside her, the condom catching everything but not the sensation of his cock pulsing, the knowledge of what was happening.
He collapsed onto her, breathing hard against her neck, and Ellie held him, running her fingers through his sweat-damp hair. She felt ... she wasn’t sure what she felt. Tender toward him, certainly. A little disappointed that she hadn’t come, though she’d known that was unlikely. Relieved it was over. Glad it had happened. All of those things simultaneously.
“I’m sorry,” Jacob mumbled against her skin. “That was like ... two minutes. Maybe less. God, I’m sorry—”