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Chapter 27 - Re: Vacation Trip - Part 19 (R18)

"I'm going to—"

"If you're ready, then put it in. Don't make me wait a second longer, Jeff."

Sitting in front of Jess, her legs spread wide as she lay on the bed, Jeff slowly rubbed the tip of his throbbing, erect rod against her soaking wet entrance to gauge her reaction.

And as he suspected, despite her bold and perverted behavior, Jess was still anxious about her first time. She instinctively tried to close her legs at the sensation of his tip pressing against her entrance.

Still, it was too late to back out now.

With his hands on her thighs, keeping them apart, their eyes locked. Jeff slowly moved his hips forward, pushing the head of his rod inside her.

"Ahh~!"

A surprised moan escaped her lips as Jess felt him enter her. She instinctively tried to close her legs again, but his grip kept them spread. Her body arched beautifully, stiffening from the unfamiliar sensation. Her hands clutched at the pillow, nails digging in, while her head tilted back, exposing her slender neck.

Seeing her reaction, with just the head inside her, made Jeff even more excited. His rod throbbed as he slowly pushed deeper into her.

Jess continued to moan in pain, her voice trembling as his rod as thick as her forearm stretched her open.

"Ah~ You're so tight, Jess..."

Jeff groaned in pleasure, feeling not only her tightness but the way her walls seemed to embrace every inch of him that had entered.

Even though he hadn't gone halfway in with his 9-inch-plus rod, Jeff already felt something tear inside her. And in that instant—

"AHH!"

A loud, pained moan came from Jess.

Looking down where they were connected, Jeff realized what had happened. A trace of blood dripped from Jess's entrance, confirming it. Then, a holographic screen from the Returner Fantasy System appeared at the corner of his vision.

---

[RETURNER FANTASY SYSTEM]

[Quest 8 – Jess's First Time (Complete)]

[Reward – Perfect Compatibility]

[Objective – Take Jess's virginity]

---

Regardless, Jeff didn't have the time—or rather, didn't care—to look at the reward.

What mattered now was easing her pain and making her feel good.

"This is the only time you'll feel this pain, so you better remember this moment, Jess."

With those teasing words, Jeff started moving his hips even though Jess was still trembling from being deflowered.

Jess continued moaning in pain as Jeff pulled out slightly, leaving just the head inside her, then slowly pushed back in to the depth where he had taken her virginity.

The way her hole resisted every pull, clinging tightly as he withdrew, and then embraced him again as he pushed deeper—each movement made it harder for Jeff to control himself. His rod throbbed wildly.

It wasn't just the feeling of penetrating her that was driving him crazy—it was the erotic sight of Jess beneath him, lost in the act.

Her eyes closed, her lips bitten as she endured the pain, her slender body arching beautifully beneath him, and her ample breasts bouncing in rhythm with his movements—it was all too much.

Each pull made him want to thrust again.

Each thrust let him go deeper inside her.

Bit by bit, her moans shifted—from pain into pleasure.

At the moment her moans became purely of pleasure, Jess opened her eyes, now filled with lust and desire, and looked at Jeff as if begging for more.

And as if answering her silent plea, Jeff's next thrust brought a new kind of stimulation.

---

[RETURNER FANTASY SYSTEM]

[Perfect Compatibility – Activated]

---

The moment his rod went deep enough for its tip to kiss the entrance of her womb, the Perfect Compatibility Function activated.

But Jeff didn't care what it meant.

Because at that same moment—

"AHH~!"

Jess experienced the most intense orgasm of her life.

And somehow, Jeff could feel her orgasm resonating through his rod and into his body.

No matter how much he tried to resist, his own climax was only seconds away.

He hurriedly tried to pull out, not wanting to cum inside and risk impregnating her. But as soon as he began to withdraw, Jess's legs locked tightly around his hips, preventing him.

"Jess… ah… unlock your legs… or else..."

Jeff pleaded, fighting the urge to finish inside her. But Jess, lost in the throes of orgasm, couldn't even hear him.

Realizing she wouldn't let go, Jeff gave in—not to climax, but to the urge to keep pounding into Jess despite her trembling from her orgasm.

He leaned down, embracing her tightly, wrapping his arms around her to feel the tremors coursing through her body.

Then, without holding back, he started thrusting again—faster and rougher. He wanted to savor every second of this sensation, his throbbing rod buried in her soaking wet hole, before surrendering to the inevitable climax.

Jess was still mid-orgasm, but each powerful thrust only pushed her higher, drowning her in wave after wave of stimulation.

Her legs stayed locked around his hips, refusing to let him go. Her arms clung to him tightly, nails digging into his back—deep enough to draw blood, painful enough to excite him further.

The room echoed with the sounds of her loud moans and the wet slaps of his thrusts. His rod slammed into her again and again, kissing her womb with every deep stroke.

And then it happened.

Jeff couldn't hold back anymore. With one final thrust—so deep it felt like he was trying to penetrate her womb—he climaxed.

Instead of a scream, Jess bit down on his shoulder at the base of his neck as she was rocked by another, even more intense orgasm, feeling his release flood her womb.

They didn't know how much time had passed.

They just kept holding each other, trembling together with a pleasure that seemed endless.

When they finally calmed down, Jeff sat up, slowly pulling his still-erect rod out of her clinging hole. The moment he did, a warm mixture of his release, her juices, and a trace of blood began dripping from her entrance, soaking the sheets.

The sensation of the fluid leaving her gave Jess another small orgasm, her body trembling again as she lay on the bed, exhausted and breathless.

Seeing that scene before him, Jeff couldn't help but feel aroused once more. His rod, still covered in the mix of their fluids, throbbed again with renewed desire.

He wanted to go another round—maybe even more.

But he didn't want to overdo it, not on their first time.

However, it seemed that wasn't up to him.

"What? Don't tell me you're done after doing it just once," Jess teased with a lustful smile. "Aren't you going to keep making me feel good, Jeff?

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