Knocked Up with Hailee Steinfeld

[TheLW]

Knocked Up
With Hailee Steinfeld
Written by TheLW
Codes: MF
Disclaimer: This FICTIONAL story was written for entertainment purposes only.

The apartment was warm, the low hum of the oven and the faint aroma of garlic and rosemary filling the space, but the atmosphere was heavy with unspoken truths. I had been invited under the pretense of a casual dinner, yet every glance, every pause, carried a weight that made my stomach tighten. Josh and Hailee both moved with a restraint, as if each action were measured to keep their nerves in check.

Hailee poured a glass of wine and set it in front of me, her fingers lingering just slightly longer than necessary on my hand. I felt a spark of something complicated, comfort, desire, loyalty, all tangled into one. I cleared my throat, trying to keep my voice steady. “So... what did you want to talk about?”

Hailee looked at Josh first, silently passing the baton, and he nodded, swallowing hard. His voice was quiet, almost strained, far from his usual easygoing tone. “We need help. Hailee and I... we’ve been trying for a baby, and... the tests... the doctor... it turns out I can’t...” He paused, looking at me with an intensity that made the words even heavier. “I can’t give her what she wants. I can’t give her what we want. And we... we need you to step in.”

My chest tightened. I’d suspected something serious, but hearing it stated so plainly, the weight of it all pressed down on me. “Step in... how?” I asked cautiously.

Hailee took a slow, steadying breath, her eyes locking onto mine. “We want you to sleep with me,” she said. Her voice was calm, and unwavering. “Until it works. Until I get pregnant. You’re the only person we trust to do this. You’re... our first choice.”

The words hit me like a physical blow, leaving my mind reeling. Every instinct screamed at me to pause, to object, to run, but then I looked at Josh. My friend’s face was open, vulnerable, tinged with desperation and hope. Josh wasn’t asking casually, he was asking from a place of complete trust, a recognition that this was more than just a favor. It was their lives, their family, their dreams laid bare in front of him.

Josh leaned forward, his hands clasped tightly in front of him. “I know it’s... a lot to ask,” he said, voice low and almost pained. “But Hailee... she’s my wife, my life. And you… you’re my friend. The only person I could imagine helping us like this. We want this so badly. We need this.”

Hailee reached out, her hand resting lightly on his, a mix of reassurance and intimacy. “I’ve always found you attractive,” she admitted softly, the vulnerability in her eyes surprising me. “This... you’re the first person I thought of. I trust you completely. I wouldn’t ask anyone else.”

I swallowed, feeling the enormity of the request pressing on me from all sides, the trust, the desire, the moral weight, the emotional entanglement. I looked between them, seeing the love, the fear, the vulnerability. And then, slowly, my own decision settled into place.

“Okay,” I said, my voice low but steady. “I’ll help. I’ll do it. But... I need to know we’re all clear on what this means. That we understand the stakes.”

Josh exhaled, relief washing over his face, and nodded. “We’re clear. We understand. And we mean it. You’re our only choice. Always have been.”

Hailee’s lips curved into a soft, grateful smile, and for a moment, the tension in the room softened, replaced with an acknowledgment of the path they had chosen. The air between them was thick, not just with desire, but with trust, responsibility, and the fragile beginnings of a plan that none of us had expected, but all of us were committed to seeing through.

I sat back, letting it sink in. This wasn’t just a favor. This wasn’t just a night, or even a few nights. It was the chance to help build a family, to fulfill a dream for two people I cared about deeply. And despite the shock, despite the complexity, I felt a strange clarity, I would do whatever it took to help them, even if it meant stepping into a role I had never imagined for myself.

I shifted in my chair, the quietness stretching between us again. “If we’re really doing this,” I said carefully, “when were you thinking of starting?”

Hailee’s fingers tightened slightly around her wineglass. She didn’t answer right away. Instead, she looked to Josh, an unspoken question passing between them. He nodded once, subtle but decisive.

Josh cleared his throat. “She’s... she’s ovulating now,” he said. There was no embarrassment in his voice, just blunt honesty. “So... tonight makes sense. If we’re going to do this, there’s no reason to wait.”

The words landed heavily. Tonight. Not someday. Not after planning or distance or time to recalibrate. I turned to Hailee, searching her face for hesitation, for doubt.

“Are you sure?” I asked quietly. “Really sure. Because once we cross that line, there’s no pretending this didn’t happen.”

She met my eyes without flinching. There was a steadiness there, but also something deeper, resolve layered over years of wanting. “Yes,” she said. No pause. No wavering. “I’ve never been more sure of anything. Starting a family... that’s all I’ve ever wanted. This isn’t impulsive for me. It’s overdue.”

Josh exhaled slowly beside her, his hand finding hers again. He didn’t look away this time. “We’ve talked about this for months,” he added. “You’re not walking into something we haven’t already made peace with.”

Silence settled again, thicker now, charged with inevitability. This wasn’t desire driving the moment, it was purpose, urgency, and a shared understanding that tonight wasn’t about indulgence. It was about commitment, trust, and crossing a line that none of us could uncross once we stood up from the table.

I nodded once, feeling the weight of it settle fully into my chest.

Hailee’s lips pressed together in a small, grateful smile. Josh gave a short nod, the tension in his shoulders easing just enough to show relief, but not enough to hide the gravity of what came next.

I stood as Hailee did, but I hadn’t taken a step yet when she reached for my hand. Her grip was firm, as if anchoring herself as much as guiding me. She didn’t say anything, she didn’t need to. She simply turned and led me down the short hallway toward the bedroom she shared with Josh.

Behind us, Josh rose from the table more slowly. “I’m going to head out for a bit,” he said, his tone controlled but tight around the edges. He grabbed his jacket from the back of the chair, pausing just long enough to look at Hailee. There was affection there, and resolve, but also something else he didn’t try to hide. “Call me when you’re finished.”

Hailee stopped at the doorway and turned back to him. “I will,” she said.

Josh nodded once, then again, as if reinforcing the decision to himself. “Take your time,” he added, before forcing a small, reassuring smile.

In the bedroom, Hailee released my hand and took a step inward, standing at the foot of the bed. She turned to face me, searching my expression one last time.

“This isn’t easy,” she said, not apologetically, but honestly. “But it matters.”

I nodded. “I know.”

She drew in a steady breath, then gestured subtly toward the bed, not as an invitation driven by impulse, but as the next step in something already decided. Whatever happened next would stay between us, shaped by restraint, trust, and the understanding that this moment was about far more than either of us alone.

Now, I hate to admit this, but getting things started was awkward at first, understandably so given the circumstances and all. Things eventually got going though, the two of us naked, me on top of Hailee, in the same bed she shared with her husband Josh.

Hailee’s legs parted beneath me, knees folding at the edge of the mattress, her body offering itself with a bravery that left me unsteady. Her eyes never left mine as I lined up, breath caught between promise and apology, and then the head of my cock breached her, impossibly warm and slick, a slow and inevitable invasion. She gasped, a ragged, open sound that ran through me, and her fingers gripped my biceps with a strength that surprised me.

The first thrust was gentle, more careful, than erotic, but even so she arched up to meet me, a shudder of relief erasing the tension in her shoulders. I pulled out slowly and pressed back in, deeper this time, and watched her lips part around a word she never quite said. It was a coordination of bodies, a joining, a purpose, not a conquest or a seduction. I fell into a patient, steady rhythm, like an answer to a question she’d spent years asking.

I tried not to think about Josh, about what it meant that I was here, inside his wife, in their bed. But every time her eyes looked to the door and then back to me, I could feel his presence, the space he took up in the air between us, dense and undeniable and, surprisingly, reassuring.

I could feel his trust in the measured tempo, the way Hailee let me in, the way I kept my hands braced on either side of her stomach instead of roaming to her throat or ass or hair, the way we both held back. It was the most restrained, the most deliberate, the most respectful sex I had ever had.

“Is this okay?” I whispered.

“I want it,” Hailee replied.

Hailee’s breathing grew shallower with each stroke, her legs curling tighter around my hips, heels digging in as if to keep me here. She never broke eye contact. It was as though she were daring me to look away, to let myself or her off the hook. Her whole body moved with a logic that was almost mathematical, arcs of her back, the tilt of her pelvis, the clutch of her fingers, designed to maximize not pleasure, but connection. It was the most intimate, and the most emotionally exposed, I’d ever been.

I braced myself on my forearms, feeling sweat beneath my skin, determined not to lose pace, not to falter. Her hand came up, fingers threading into my hair, holding me in place. “Don’t stop,” she breathed, but I hadn’t even thought about it.

The rhythm changed before I even realized it, my hips pulling back farther, the slide into her less tentative, our bodies finding an ease that cut against the premise but not the intent. Hailee shifted, raising her knees higher, locking her ankles over the small of my back, and I fell into her, the length of me sheathing fully on each thrust. Her face tugged tight in ecstasy and then softened, the muscles in her jaw unclenching as I learned the pace she wanted, and needed me to set.

The first few minutes had been all caution, but now there was nothing polite about the way she moved against me, chasing each thrust with motion of her own. Her breath stuttered in my ear, broke off into choked whimpers, then resumed, faster, more urgent. She let go of my arms just long enough to fold them over her head and clutch the pillow, her body bowed up to meet me, breasts grazing my chest.

She started to murmur against my ear. “Yes, yes, there, that’s it, right there…” and her hands began to roam, at first just braced on my biceps, but then trailing up over my shoulders, nails lightly digging into the back of my neck. Her touch was deliberate and sure, as if she was testing her own boundaries, seeing how much she could ask for and get away with, and it only made me want her more.

I ground into her, the friction building fast, every movement slicker than the last, and the sound of it, the wet, insistent slap and the soft thud of the headboard, filled the bedroom, louder than either of us seemed prepared for. Hailee’s mouth was at my ear again, her breath hot and heavy now, her words disintegrating into vowels and moans. I tried to ride the edge, but it was impossible to ignore the heat and the clutch of her around me, the way she never let me drift too far from her eyes. It wasn’t just a need.

Her thighs trembled as she worked herself against me, slow at first, then tenser, faster, with a need that proved she had thought this through far beyond this moment. I was in awe even as I grunted, holding her hips and almost losing myself in the way her hands pressed to my chest, then clawed, searching for purchase, longing, reassurance. She wasn’t delicate, this was needed. This was the purpose, and I was only the instrument, not the melody.

I slid my hand up between us, thumb moving in tight circles at the apex of her thighs. Her breath caught, sharp, involuntary, then she bit down on her lower lip, hard enough to draw some blood.

She bucked up, nearly arching me off her, and that’s when it happened, the subtle snap, the crack in restraint. Hailee wrapped both arms around my shoulders, dragging me down, her lips grazing my cheek, jaw, throat. “Harder,” she hissed, not as a plea but a command, and I gave her what she wanted, hips driving into her, one hard thrust after another, relentlessly.

Hailee’s head was thrown back, mouth open, eyes squeezed shut, and I saw all of her in that moment, her jawline taut with effort, her hands balled into fists, her chest flushed and quickening with each shallow breath. The noises she made went from whispered encouragement to full, desperate cries, a song of relief and release that poured out of her in time to the rhythm we’d built together.

The need to hold back evaporated. I gripped her hips, fingers digging in until she gasped, and moved with her, not above or against but with, every slide, every withdrawal, perfectly matched to her.

She came first.

It happened suddenly, a tremor passing up Hailee’s thighs and into my hips, her legs cinching so tight around me that I nearly lost balance. She shuddered, hands grasping fistfuls of sheet, eyes glassy and wide open, fixating on a spot just past me. The sound she made was low and guttural, a sob, a moan or maybe both, and it pushed me to the edge immediately, a gravitational pull that stripped every other thought from my head. I felt her around me, drawing me deeper, until I couldn’t have escaped if I wanted to. My own release followed, sharp and blinding, driven by the knowledge that this was not some aimless hookup but a collision of purpose and trust and all the years that had led to this night.

It left us both winded. I let my weight settle onto my elbows so I didn’t crush her, and for a few seconds we said nothing, oxygen returning in slow, ragged breaths. Her arms found their way around my neck and pulled me down, face to face, so close I could see the flecks of amber in her brown eyes.

Three weeks later, Josh and Hailee’s place was wrapped in the quietness of an early morning.

Hailee stood alone in the bathroom, barefoot on the cool tile, staring down at the small plastic test resting on the edge of the sink. She folded her arms tightly across her chest, heart racing, counting the minutes even though she already knew she wouldn’t look away.

When the timer finally chimed, she stepped closer.

Two faint pink lines stared back at her.

For a split second, she didn’t breathe. Then the meaning rushed in all at once, sharp and overwhelming. Her hands flew to her mouth as a laugh escaped her, half disbelief, half pure relief. Her reflection in the mirror looked different somehow, lighter, brighter, transformed by a truth she had been desperate to see made real.

“Josh!” she shouted, her voice echoing down the hall. “Josh, come here!”

Footsteps thundered toward the bathroom, panic flashing across his face as he burst through the doorway. “What’s wrong?” he asked, already scanning her for tears.

Hailee didn’t answer right away. She just smiled, wide, radiant, unmistakable, and held out the test.

Josh’s eyes dropped to it.

Two lines.

His breath caught. “Hailee...?” His voice cracked as he looked up at her, afraid to hope too hard.

“I’m pregnant,” she said softly. “It worked.”

For a moment, he just stood there, stunned, before emotion finally broke through. He pulled her into his arms, holding her as if she might vanish if he loosened his grip. The months of disappointment, fear, and grief dissolved in an instant, replaced by something almost unreal.

“We’re going to be parents,” he whispered.

She nodded against his shoulder. “We are.”

The End