I Became the Maid of the Lout Prince

Chapter 296 [First Time (2)] - R-19!



T/N: This bonus chapter is sponsored by Soothsayer (4/10) and is rated R-19! Read at your own risk.

“Ahhh, ngh…! Haa, haaa….”

 

Lilith let out a pained moan as Ethan’s length was swallowed by her lower entrance.

For the first time in her life—or rather, across both of her lifetimes—she was experiencing the pain of losing her virginity.

It was the throbbing sensation in her lower body that overwhelmed her entire being.

The only saving grace was that she hadn’t said out loud everything running through her mind. No matter how much Ethan loved her, he would have been caught off guard by the string of crude curses she was suppressing.

 

‘Shit… it hurts like hell….’

 

Was it supposed to hurt this much? In books or games, they didn’t seem to show this kind of pain.

On the contrary, sex between people who loved each other was supposed to be blissful and painless, or so she had heard.

Of course, she knew media exaggerated things, so she wasn’t naïve enough to believe all of it uncritically. But even taking that into account, this was unbelievably painful.

As these thoughts swirled in her head, Lilith focused on trying to calm the storm of pain overtaking her lower half.

 

‘At least I’m the one on top… that’s a relief.’

 

If Ethan had been moving forcefully beneath her in this state, she might have fainted from the pain.

Just inserting it hurt this much—she couldn’t imagine how much worse it would have been if he’d started moving.

Choosing to be on top and take control herself, even after a proper prelude, might have saved her from an even greater agony… or so she thought.

 

‘…Oh.’

 

And then it hit her—a critical mistake she’d just realized.

She had skipped over the foreplay that would’ve prepared her body and dove straight into the act.

 

‘God, I’m such an idiot….’

 

If she’d just held still, Ethan would’ve taken the lead and properly prepared her body, making the whole thing smoother. At least, it wouldn’t have been this painful.

Regret washed over her too late. Ethan’s length was already deeply buried in her unprepared body, stretching her mercilessly.

 

“Are… Are you okay, Lilith?”

“Nngh, y-yes… I’m fine….”

“For being fine, there’s quite a bit of blood….”

“This is something every woman has to experience at least once in her life… Did you think I’d be weak enough to be defeated by something like this…?”

“No, I didn’t mean it like that, but—”

“This is… really nothing at all… Just… I’m not the kind of woman who would let something as simple as physical union make her crumble….”

Schluck.

“Hngh, HAAAAAAH?!”

 

As she took him in a little further, another wave of sharp pain ripped through her, pulling a loud cry from her lips.

Her expression was undeniably more in pain than in pleasure, which left Ethan looking flustered and concerned.

 

“Haa, haah, haaah…”

“It’s okay, Lilith. Take your time. I’m not in any rush.”

“Y-Yeah, hehe… In that case, can I just… rest like this for a little while?”

“You can rest as long as you need. If it’s too much, we can even—”

 

Ethan stopped himself before finishing his sentence. He was about to say, “We can just do this another time.

Having been with Lilith for years, he knew her too well. One of the things he had come to understand about her personality was her pride. 

If he said something like, “Let’s stop for today and try again later,” she’d only push herself out of sheer stubbornness, forcing herself to endure the pain just to prove a point. That was just how she was, and Ethan had learned that the hard way over the years.

If he waited patiently, she’d recover and start moving on her own. He had spent enough time with her to learn how to handle her quirks, whether he liked it or not.

 

“Haa, ngh, haaah…”

 

Just as Ethan had predicted, Lilith adjusted herself on top of him and began moving again.

She deliberately quickened her pace, as if trying to mask her pain.

 

Schluck.

“Ngh… haaah…”

Schluck, schluck.

“Urgh, ha… haaah…!”

 

Ethan couldn’t help but feel a sense of disarray at how different this was from what he had imagined their first time together would be.

While the part of his dream where Lilith shared her first time with him had come true, everything else was starkly different.

In his mind, he had pictured laying her down gently on the bed, taking the lead, and moving in a way that made her feel cherished. He had envisioned soft foreplay to relax her, followed by her welcoming him with a blissful smile, pulling him close with warmth and affection.

Instead, here they were, with Lilith on top, pushing through her pain and stubbornly forcing herself to continue despite how unprepared she was.

 

‘Looking back, we didn’t even bother with proper foreplay,’ he realized, feeling a pang of guilt.

 

Everything about this was a mess. Could something like this even be considered a proper first time?

Ethan made a silent promise to himself: this wouldn’t be the memory that defined their intimacy. They’d have to cover this rocky start with better, more meaningful experiences in the future. This one, raw as it was, would have to be overshadowed by something gentler, something filled with shared pleasure rather than pain.

Not just once, but multiple times, until this awkward first attempt was buried under sweeter memories.

 

Schluck!

“Ahhh, nghhh!” 

 

Lilith suddenly collapsed forward onto his chest, letting out a pained cry.

Her body was trembling, her strength clearly at its limit. The process that was meant to express their love for one another had turned into an ordeal that left her gasping for air.

Seeing her like this, Ethan felt a pang of helplessness. He wished he could take on her pain himself, to carry some of the burden she was feeling, but that wasn’t physically possible. All he could do was be there for her and try to ease her suffering in the ways he could.

 

Pulling her closer.

“Ugh… Y-Young Master Ethan… ?”

“This isn’t the time for formalities, Lili. Just call me Ed,” he said softly.

“Y-Yeah… Ed…”

 

She was… adorable.

Lying atop him, her face buried in his chest as she stammered his name, she was irresistibly endearing in her vulnerability.

Ethan couldn’t help himself. Gently, he placed his hand on the back of her head, pulling her closer, until her lips met his.

 

Chup.

“Mmm… nngh…”

Slurp, schluck.

“Mmh… nggh… ahh…”

 

Every time their lips touched, every time their tongues danced and mingled, every time her soft moans escaped her, Ethan’s desire for her flared hotter.

He started moving beneath her. Just barely.

He pushed into her slowly, cautiously, almost imperceptibly. He was careful to keep his movements subtle, afraid that anything too sudden or forceful would only hurt her more.

 

“Mmnh… ngh… hhaa…”

“… … …”

“Ahhh… nnnghh…”

 

Even so, there was no way Lilith wouldn’t notice.

She had to feel him moving inside her, pressing deeper, pushing through her sensitive walls. But she didn’t protest.

Instead, she kept her lips locked with his, her arms trembling as she clung to him. Whether it was an act of quiet endurance or her own blossoming desire, she made no move to stop him.

Taking her reaction as silent consent—or perhaps even encouragement—Ethan gradually began moving a little more. His hands found her hips, guiding her subtly in rhythm with his movements.

 

Schluck.

“Ahh… nnngh…”

 

Her voice changed.

For the first time since they’d begun, the tone of her moans shifted. It was still laced with pain, but there was something else there too—something softer, sweeter.

Pleasure.

Or at least, that’s what Ethan dared to hope. Maybe he was imagining it, a wishful illusion conjured by his desire for her to feel good. Maybe it was just his longing to see her experience something more than pain.

Even so, he clung to that hope.

Taking it as a sign he was doing something right, he kept his pace steady, his movements gentle and deliberate. Slow enough not to hurt, yet persistent enough to keep them both aware of each other’s presence, their connection.

 

Schluck. Schluck. 

“Haa… nghh… Ed…”

“It’s okay, Lili… just take your time.”

 

Her breath hitched as she nodded against his chest. Her body trembled, but now there was less resistance. Slowly but surely, her pain seemed to give way to something else.

Something warmer.

Ethan moved with deliberate care, each motion deep and slow, designed to stimulate the deepest, most sensitive parts of Lilith’s body.

 

Schluck. Schluck. Schluck.

“Haa… mmnh… ngh! Haah, ahhngh…!!”

 

Lilith’s moans gradually changed in tone. What had begun as sharp cries of discomfort transformed into softer, more sensual sounds, not unlike the noises she made when he’d teased her breasts during their past intimate moments.

How long had they been like this, locked together in a slow rhythm, lips meeting and parting as their breaths intertwined? Ethan wasn’t sure. Fifteen minutes? Maybe more?

All he knew was the rising heat pooling in his lower body, an inevitable tension building as his movements continued.

 

‘Should I… finish inside?’

 

It was a simple thought, but one that brought hesitation.

Given their relationship, it felt almost absurd to worry about asking her permission. Yet, Ethan didn’t want to risk doing anything that might upset or inconvenience Lilith, no matter how small.

He knew the risks—pregnancy wasn’t guaranteed, of course, but if it did happen, it might disrupt her life in the academy, her studies, and her goals. 

And if that happened, he knew she’d carry resentment, and he couldn’t bear the thought of being the cause of such regret.

Breaking their kiss, Ethan met Lilith’s gaze, his question lingering in his expression even as his lips remained silent.

Lilith, still panting softly, was the first to break the silence.

 

“I-It’s okay. You can finish inside.”

“…Really?”

“Y-Yeah… we can use Clean later. That should work as contraception too…”

“Oh…”

 

It was so obvious. How could he have forgotten something so basic? Apparently, having Lilith like this, vulnerable and beautiful, had turned him into a complete fool.

 

“And… well…” she added, her voice dropping to an almost inaudible murmur. “I wouldn’t… really mind if it happened.”

“What?”

“…N-Nothing, Ed.”

 

Her cheeks flushed with embarrassment, and Ethan decided to let it go, pretending he hadn’t heard. Instead, he focused on her, on them, and on the need now overwhelming him.

Lowering his hips again, he moved deeper into her warmth, his length gliding against her tight walls. Every motion sent wet, sticky sounds into the room, the slickness of their union filling the air alongside Lilith’s increasingly fervent moans.

 

Schluck. Schluck.

“Ahh… mmnh… ahhng…!”

 

Her body responded instinctively, her trembling hips pressing down in rhythm with his thrusts. Their pace remained slow but purposeful, each movement drawing them closer to an inevitable climax.

Ethan could feel it now, the pressure coiling tighter at the base of his spine, ready to snap. His movements grew slightly more insistent, his hands guiding her hips to meet his.

Finally, the moment arrived.

 

Throb. Throb.

Splurch! Splurch!

 

Thick, hot liquid spilled into her, coating her deepest walls and filling her completely.

 

“HAAAAH… OHHHH! HNGGGGH…!!”

 

Lilith’s back arched as the sensation overwhelmed her, a tremor running through her entire body as she cried out. The warmth that filled her, the sheer intensity of it, sent shudders through her limbs.

Ethan pulled her close, his lips finding hers again as he rode out the waves of his release.

Their kiss was deep and desperate, their breaths mingling as the room was filled with nothing but the sound of their union and the wet, sticky aftermath of their climax.

 

Splurch… splurch… 

 

When it was over, they finally broke apart, their lips parting with a string of saliva connecting them. The same sticky connection mirrored the mess they’d made between their bodies, a tangible reminder of their shared intimacy.

 

“E-Ed…”

“…Yeah, Lili?”

“I… I just wanted to call your name.”

 

Her voice was soft, almost shy, as she snuggled closer to him, her arms wrapping around him tightly.

Ethan couldn’t help but smile, his heart swelling with affection for the woman in his arms. Pulling her closer, he held her tightly, savoring the warmth of her body against his.

For hours, they stayed like that, wrapped in each other’s arms, letting their shared warmth banish the world outside.

T/N

They finally did it!

Sincerely apologize these chapters took too long, I’ve just been way too busy with everything going on and finally had time to finish these now. In line with this, I do find it hard to commit to finishing what I started past Chapter 319. 

I’m really hoping I’ll have as much availability as I do now over the coming days and rest assured I will finish the remainder before handing them over to Ruminas.

Thank you for your support and I look forward to seeing you in the next one.

Next chapter will be updated first on this website. Come back and continue reading tomorrow, everyone!

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