Chapter 12: Popping Cindy’s Cherry!

"Tomorrow, we take over the North District. Raccoon City will be ours. From now on, you better stick to my rules. Don't pull any stunts once you're paid. I won't tolerate robbery or petty theft here. Everything happens according to my way. I won't accept small-time games."

Tristan's eyes narrowed slightly as he spoke. 

He had bigger ambitions in mind, and though these hoolingans weren't suited for running legitimate businesses, they could still be used as tools to quickly accumulate funds in the early stage.

With his work done for the day, Tristan returned to his pub and then went to his apartment—with Cindy.

In the world of Resident Evil, Cindy was a lesser-known character from Outbreak. However, unlike main characters such as Claire, her fame was almost nonexistent.

But Cindy had her own strengths. She was gentle yet strong and wouldn't break down at the sight of a zombie.

Most importantly, she was obedient, a quality Tristan valued above all.

He needed a woman who could manage his assets, someone who would remain loyal, and Cindy fit the role perfectly.

Speaking of Cindy, as she entered Tristan's apartment, she was tense, aware of what awaited her.

This was her first time, and she was quite nervous, but she didn't regret her decision because her mother was truly happy and relieved when she received so much money today. 

Her father's illness was severe, and the daily medical costs were crushing. As a bartender, she had no means of covering the expenses.

Rather than watch her father die slowly, Cindy chose to become Tristan's mistress. At least this way, her family would have financial security, and her own life would change for the better.

And if she had to choose, a young, handsome man like Tristan would be the best option.

Holding the beautiful girl close in his arms, Tristan gently caressed her delicate body.

"Relax, and just leave everything to me. Since I have promised, I will save your father at all costs. Once he's better, we'll figure everything else out. Money can always be earned again, but life is precious. You're my woman now, and your father is like my own. As your man, I won't let him suffer."

Cindy was deeply moved by his words. She wasn't naïve—she knew exactly what this arrangement entailed, but given the circumstances, this was the most beneficial outcome to her.

"Thank you, boss. Without your help, I wouldn't know what to do. I'm just worried I won't be good at handling finances."

Tristan tilted her chin up and kissed her softly.

"You'll be fine. I trust you. And remember, call me 'dear' or 'honey,' not 'boss.' You're my woman now."

"Okay… h-honey. Let's… take a break."

Cindy's eyelashes fluttered as she blushed.

Despite her outward confidence, she still felt nervous and shy. She didn't love Tristan—not yet—but she could see herself falling for him in time. After all, feelings could grow.

But Tristan wasn't focused on emotions. What mattered to him was the physical connection. He understood that after being fucked too many times, women would naturally develop feelings.

So he directly ignored her request for a break and kissed her again.

"Mmm…"

Cindy's body trembled slightly, aware of what was about to happen. She didn't resist. Instead, she chose to embrace it.

Tristan laid her down on the bed and began to undress—both himself and her.

His hands trailed over Cindy's skin, skillfully exploring and playing with her body. His fingers found their way to her most sensitive places, teasing and stimulating her sexual desire.

Before long, under Tristan's tender touch, Cindy's fear began to fade away. Her body responded, and a subtle warmth grew between her thighs, making her a little wet.

The sensation left her feeling strange—nervous yet somehow expectant.

Her pink labia parted slightly, revealing a delicate slit.

Cindy was untouched, her innocence was on display, and even her labia, small and untainted, seemed like fragile petals waiting to bloom.

Tristan positioned himself between her legs and gently pressed the head of his cock against the opening of her vagina. Then he smiled down at her, whispering in her ear.

"Cindy, I love you."

With those words, he began to push forward, his hips pressing against her as her body welcomed him slowly.

"Haaa~!" 

Cindy exhaled, her eyes closing tightly as she felt his hot rod parting her vagina for the first time and moving forward.

The sensation overwhelmed her. Soon, Tristan could feel it too—the resistance to her innocence, her hymen.

Tristan grinned, and with one firm thrust, he broke through her hymen.

Plop!

The sound of her hymen being ruptured echoed like a bottle being uncorked, and Cindy let out a sharp scream of pain.

"Ahhhh!!!"

Her virginity was taken away!

Seeing her bright red virgin blood on his cock, Tristan became even more excited and continued to press hard, watching his penis being gradually swallowed by her pink vagina.

He could immediately feel his cock being tightly wrapped by her vaginal walls as soon as it entered deep inside her. It was as if a flesh sleeve was wrapped around him, and it continued to squirm, sucking his penis into it inch by inch.

"Ah!"

Cindy's voice was trembling with both pain and shock.

Tristan paused and bent down to soothe her. His hand caressed her body, fingers tracing over her sensitive spots as he pressed gentle kisses along her cheek.

Their lips met and tongues tangled as they kissed deeply, which eased the pain and stirred her sexual desire, pushing her body into a state of arousal.

Tristan was also lost in the moment, enjoying the overwhelming sensation of popping Cindy's cherry. After Jill, this was the second virgin he had claimed, and for some strange reason, it made him calm down a little.

Slowly, he began to move again, thrusting gently at first, mindful of her discomfort.

"Haaa… Mmm…"

Cindy's breath came in soft gasps.

Too shy to moan, she bit her lip, her body trembling beneath him. The scent of her perfume, mixed with the heat of their bodies, fueled Tristan's desire.

"Does it feel good?"

His voice was a little husky as he moved slowly. At the same time, his cock swelled inside her, stretching Cindy's virgin vagina to its very limit, filling her completely.

Their bodies fit together as if they were made for one another.

Upon hearing his voice, Cindy finally opened her eyes, her breath hitched as she hesitated for a moment. Then, with a delicate touch, her fingers brushed through Tristan's hair.

"Hmm...comfortable...are you tired? Take your time... ah."

Her voice was soft, a breathy whisper, caught between pleasure and the lingering pain of her first time.

But it was this unexpected tender gesture—that fragile, vulnerable surrender, like a lovely little wife—that surprised Tristan. He felt his blood rush to his cock.

He had tried to be gentle, but the tightness and heat of her body were overwhelming. His cock throbbed, and despite his best intentions, he found himself moving faster, unable to resist the sensation.

Certainly, he didn't want to finish too soon, but the way Cindy's slippery, tight vagina gripped him was indescribable.

Warmth, wetness, and intense pleasure enveloped every inch of his cock.

Her pussy pulled him deeper, and the friction between her vaginal walls and his shaft sent waves of different sensations over him, pushing him closer to the edge of release, making him want to ejaculate.

"Cumming!"

"C-cum... inside... Haaang~"

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