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Cassie moved her head up and looked him in the eyes.

She could see his deep black pupils, and although she had seen them many times before, today something was different.

She could feel them in a much deeper way.

Many thoughts were running wild in her head.

She has taken him in her embrace, cried, and even asked for his forgiveness.

She didn't know how he would react, and she was afraid that this might even backfire and break their friendship too.

She didn't want that to happen, she wanted to stay with him, and the actions she had just committed could turn, upside down.

She needed him.

Her hands moved over his head, and she leaned forward to kiss him.

Jack, felt her kiss coming towards him and didn't resist.

Although he wanted to tease her, he still wanted to conquer her.

In his mind, she was already his.

Jack liked her before, and now that he could get her, he would not let the chance slip from his hands.

And he could tell that she had realised her mistake, and that was the reason why she was asking for forgiveness.

Jack let her come near him, and finally she landed her lips on his.

And soon enough, she realised what she had done, her face turned red, and she moved back.

"I am sorry..." She apologised again, but for a different reason this time.

She apologised for the sudden kiss.

Jack smiled at her and, grabbing her neck, he also landed a kiss on her lips.

"Ahh..." Cassie suddenly got startled, but soon she opened her lips and welcomed his tongue.

Jack closed the door behind him with his hand and picked her up in his arms.

"So you want this?" Jack chuckled, looking at her.

Cassie, who felt his gaze, burned her face into a red tomato.

She buried her face in his shirt, not wanting to make eye contact with him.

Her heart was jumping out of her chest, and she could feel every beat of it.

Tingles were moving through her body as anticipation rose in her heart.

She knew what was coming next, and her heart started beating even faster.

She kissed Jack in desperation and hurry, she didn't think about the consequences too much.

She was a virgin and never knew her first time would be so sudden, she wasn't prepared.

Jack placed her on the bed and took out his shirt and pants.

"You have become so bold! To think that you would kiss your best friend." Jack teased her as he got over.

His hand moved her red one piece up, revealing her black panties.

"Shut up... You are the one taking me to my bed." She murmured as shame flushed her face.

Jack chuckled.

"I was leaving, wanna know who came crying and hugged me?"

Cassie turned even redder at his words.

He knows how to tease her to death.

She was about to argue with him, when she felt his hand moving over her panties and a tingle moved through her body.

This was her first time, having an intimate act with anyone, and she doesn't know what to do.

She only felt embarrassed and ashamed at such acts.

Her hand moved, and she grabbed his, that was trying to take her panties off.

"This is my first time..."

Although she knew that Jack knew about her virginity, she still reminded him so he would stay gentle.

Both of them were best friends and shared everything about them, and Jack knew that she was a virgin.

Although she used to like Ron, Jack was sure that she had already forgotten about him and was now madly in love with himself. Her three hearts were the evidence.

Jack narrowed his eyes in a smile at her words. "I know, don't worry, nobody knows you better than me."

Jack moved her hands away, sliding his fingers over her navel. His hands slid down her ass, and then, squeezing her buttocks, he hooked his hand in her panties and pulled them apart.

When Cassie realised that her panties were gone and Jack was looking at her private parts, she covered her face with shame.

Her ears turned red, and she didn't dare look at him.

She was a girl after all, no matter if she was a tomboy, showing off one's private region without any shame was difficult for her, and on top of all that, she was a virgin as well.

"So you can act cute as well? I thought you were the devil reincarnated in a human body."

"Stop saying such stuff, or I will kill you!" she said while her face was still covered by her hands.

As both of them were best friends, insulting each other in a joking manner was common for them.

They have fought countless times and even cursed at each other, but in the end, they still managed to keep their friendship.

"Well, I have to say, not only are you acting cute, but other things about you are cute as well." Jack said, and his finger rolled through her vagina.

"Ahh..." A voice leaked out of her mouth, and Jack laughed in response.

"You!" Cassie playfully kicked her leg, to make him stop saying such embarrassing words.

Her hands moved away from her face, and she saw an evil smile on his face.

He was enjoying teasing her.

And the more reaction she gives, the more he will tease her.

"Don't move your legs so much, or you will hurt yourself." Jack caught her leg and placed it over his shoulder.

His body moved forward, and he leaned in for a kiss.

"Hmm..." Cassie groaned as her leg stretched in front of her, his bulge rubbed against her vagina, and her body quivered.

"Mmm..." Opening her lips, she welcomed his tongue. She could still taste the lingering beer on his palate, but she didn't mind it.

Both of them got engaged in a deep, passionate kiss.

Jack moved his hand, and his fingers reached her crotch.

"Mmm..." Cassie moaned as she felt his finger fondling against her clit.

"Ahhh...!" Her eyes widened as his finger inserted itself into her opening.

"ahh..."

Jack reached her inner wall with his finger and started rubbing it gently, making moans leak out of her mouth.

He could feel his finger getting wet with every stroke.

His nose nuzzled over her neck, liking it, and then he finally took a kiss on her neck.

"Ahh... Slow." Cassie grabbed his hair, her mouth open in pleasure.

"You are so wet." Jack looked at her with a smile on his face.

"Shut up!" Her cheeks were red from his constant teasing, she was a virgin, and this was her first time doing such things.

[Target Information.

Name- Cassie

Age - 23

Sexual Preferences: Would be fascinated by a big penis.

Kinks: massage sex with oil.

Current Mentality: She regrets that she got you so late when you were in front of her all this time, wants to please you by any means possible. ]

Jack saw her information and smiled.

'So she would do anything to please me?' He wanted to test the limits.

An evil smile crept up on his face, and he moved back, letting her leg move away from his shoulder.

"Remove your dress." He ordered.

Cassie listened to him; however, she didn't protest, and moving her hand, she pulled her one piece from her body.

Her red bra was revealed in front of Jack, hiding two big dumplings.

"Why are you wearing an unmatched bra?" Jack asked with a smile.

He remembered that she wore a black panty and now in front of him was a red bra.

He knew the reason, it was because, she was careless and never gave any thought to her dressing manner, it showed her slight tomboyish nature.

Although even tomboys have dressing sense, she is just more on the careless side.

"Does it matter?" She said this and took out her bra, revealing her jiggly peaks.

"No, it doesn't." With a grin, his hands reached for her bosom and started kneading her boobs.

"Gentle..." She tried to remind him, but he seemed to enjoy fondling them.

She had the squishiest and softest boobs Jack has handled till now, and they gave his hands indescribable pleasure.

He felt like he was holding two big marshmallows in his hands.

Cassie, on the other hand, was also feeling pleasure, her guarded chest, which she had never let anyone touch, was now revealed in front of Jack, and he was using it however he wanted.

She could feel the warmth and roughness of his hands on her chest.

"Turn around." After a fondling session with her chest, Jack ordered her to turn around.

Cassie gulped her saliva while listening to his deep voice, She was used to going against his words and arguing with him all the time.

However, now in this condition, his words were like ultimatums for her. She somehow can't seem to go against them.

Jack pinched her nipple as she was struggling to move. "Fast!"

"Yes, I am doing it..." Her body moved, and she turned around on all fours.

Jack could see the full view of her luscious ass.

"Ahh..." Cassie's eyes widened as she felt something rubbing against her entrance after she turned on all fours.

Her eyes glanced back, and her heart skipped a beat.

"Isn't that too big?..."