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Otherwise, he would test his luck and win big. But there was nothing he could do about that. Laws were laws, and when it came to gambling, it was highly regulated. So much so that even if he could successfully lie to the dealers about his age, he would never be able to cash out his chips.

Thus, Alex returned to the penthouse, rather than test his fortune. Upon entering his room, and tossing his gym bag to the floor. Alex was immediately surprised by what he saw. Waiting for him on his bed was none other than his older sister Kristina, who was dressed in nothing but a bathrobe, which was open to reveal her sinful naked body.

When she saw Alex enter, the young woman blushed before rising to her feet and begging Alex to do to her what he had done to their sister.

“Alex… I can’t take it anymore! I need your cock inside me right now!”

Alex wore a completely stoic expression on his handsome face, as he snapped to attention and saluted the woman as if he were in the military and she was his commanding officer. He then made a joke that thoroughly annoyed his older sister.

“Yes, Ma’am!”

Kristina could not take Alex’s bullshit, not now, not after she had spent the last hour in the man’s bed, inhaling his pheromones. She instantly grabbed her little brother and dragged him into bed with her. Despite having zero experience with sex and romance.

Alex naturally took the lead from here, as he kissed Kristina on the lips, before working his way down to her neck, breasts, stomach, and eventually her virgin pussy. It did not take long for the young woman to climax after her little brother had begun licking her twat like he was a master at the art of cunnilingus.

And once Kristina had cum, Alex smirked as he pulled down his pants and revealed his large shaft. Which he shoved in the girl’s face and demanded reciprocation.

“Alright, now it’s your turn!”

Though Kristina had seen Alex’s cock before, due to his shamelessness, and tendency to walk around the house nude whenever he could get away with it. She had never seen it up close before. And Immediately grabbed hold of her little brother’s cock where she began to stroke it in disbelief at its overall length and girth.

“It’s so huge!”

Alex simply smirked at his older sister’s compliment, as she began to suck on the tip with almost zero skill. After all, this was the girl’s first time seeing a cock in person, and because of this, she had no idea what she was doing. But Alex walked Kristina through the process before he eventually released a hearty stream of his thick semen down his sister’s throat.

Once Kristina had tasted Alex’s semen, it was almost as if it were the most potent aphrodisiac, as her body lit aflame, causing her to become even more impatient than she was before.

“Alex, I can’t wait any longer! Please! I need you inside me now!”

Alex, of course, nodded his head as he lined the tip of his cock with his older sister’s virgin pussy. And without warning, he forced it inside, penetrating past the young woman’s hymen, and claiming her virtue for himself.

The man grunted in pleasure as he slowly moved his hips forward in a gentle yet firm display. One that, though initially painful for Kristina, quickly turned to pleasure, as her face flushed red, as if she had suddenly become intoxicated with lust. She then asked a shameless question, wanting to know the truth now that she and Alex had finally united as one.

“Tell me, little brother… Whose pussy is better than mine, or Maddie’s?”

Alex simply scoffed when he heard this, before increasing the intensity of his thrusts, while mocking his eldest sister for getting ahead of himself.

“The two of you are identical twins! Did you seriously think there was that much of a difference between you? You are getting ahead of yourself, Kristie? Perhaps I should punish you for your arrogance?”

Contrary to what Alex was expecting, Kristina simply mocked him, despite the fact that she was moaning like a bitch in heat, her attitude had always been far more forward and arrogant of than her twin sister’s. And this proved itself to be true even in bed.

“If you think you’re man enough to do so, then go ahead, little brother!”

Since he had been given the go ahead, Alex flipped his older sister over, and began to ruthlessly pound her from behind, while also choking her to the bring of unconsciousness. An act which caused the virgin to cum all over his cock, as she began to plead with Alex to release her, while apologizing for her arrogance.

“Oh shit! I’m sorry Alex! I promise to behave myself! Please don’t choke me out!”

Alex scoffed once more while he thrust his hips entirely forward, and shot his seed deep inside his older sister’s womb, while also choking her out on the spot. He immediately released the chokehold once the woman had passed out, allowing her to regain consciousness not long after. But soon enough, she went to sleep, believing her little brother would stay by her side the entire night.

—

Diana and Madison were forced to listen to Kristina’s loud moans, which echoed across the penthouse. After all, it was a much smaller penthouse than the one Alex had in Seoul, and because of this, the moans were much louder than the two women were used to.

After her discussion with Alex earlier in the day, Diana had begun to feel an intense sense of guilt, among other emotions. Though she was used to the sounds of her son ravaging other women, the fact that the man had now claimed both of her daughters, and her older sister, meant that Diana was incredibly sexually frustrated. So much so, she began masturbating to the idea of Alex fucking her instead of Kristina. All the while cursing him out for making her this way.

“That little brat! I can’t believe he fucked both of my daughters and my older sister! I am such a terrible mother!”

Yet no matter how hard Diana tried, she couldn’t herself to cum. Almost as if her body was refusing to do without her son’s phallus inside of her. Eventually, when Alex and Kristina were finished, Alex left his room behind and went to get a glass of cold milk.

Where he was surprised to see his mother waiting for him. Her expression wasn’t one of anger like he expected, but rather one of pure jealousy, as she asked Alex why… Why had he fucked her daughters, and her sister, but not herself?

“Just answer me this… Why? Why not me? Have I really wronged you so much that you will fuck my sister and my daughters, but not me?”

Upon seeing that he had thoroughly broken his mother, Alex chugged the milk from the carton itself before wiping his mouth. Once he had done so, he smirked before responding to the woman who had raised him.

“Oh? So it appears you are finally starting to be honest with yourself… I could make you mine… You could join your sister and your daughters as one of my lovers. But… I feel as if you haven’t properly paid the price yet…”

Diana had no idea what she had to do to get her son to forgive her, and was quite offended by the idea that she still had to be tortured more before the man would do so. Thus, her tone was quite high as she asked Alex what exactly he had in mind.

“Not paid the price yet? What more do you want from me?”

Noticing that the woman was basically willing to do anything he wanted at this point, Alex smirked and motioned towards the woman to follow him. Where he led her up to his bedroom. Kristina was passed out naked in his bed with a river of cum leaking from her twat. A sight which only made Diana all the more aroused.

And then Alex did the unthinkable, and reached into his closet, where he pulled out a sexy prisoner costume, along with a pair of handcuffs. He tossed the outfit towards his mother with a sinister smile on his face.

“We’re going to play a little game… And if you do it right, I might just reward you… Don’t worry, that costume is in your size, so it should fit quite perfectly….”

Diana had no idea how Alex knew her measurements, but she sighed, and was just about to take the uniform into the bathroom, and change into it, when Alex began to strip himself, and dress in the outfit of a police officer.

The woman couldn’t help but stare at her son’s immaculate naked body and had without realizing it, began to strip in front of him. Once she was fully naked, Alex stared at his mother’s pristine body, and grew erect, despite the fact that he had just fucked his sister no more than five minutes ago. He couldn’t help but make a comment on the milf’s curves.

“Not bad… Not bad at all!”

This caused Diana to flush in embarrassment, as she finally got dressed in the prisoner’s outfit, which was beyond skimpy. She was just about to ask what next, When Alex took her down to the floor in some playful wrestling, and cuffed her hands behind her. Diana yelped out in shock, when she realized her son was now in full control of her, and there was nothing she could do about it.

“Wait! Alex! What are you going to do to me?”

Alex wore a sadistic smirk as he pulled the woman’s orange shorts down to her knees and rubbed his finger against her moist twat before licking it. There was an almost monstrous tone in his voice as he voiced his true feelings aloud.

“I have been waiting for this moment for a very long time…”

After saying this, Alex pulled out a leather paddle from his closet, one that had stainless steel studs across it. He began to motion it menacingly towards his mother’s ample bottom. Causing her to cry out in fear.

“Wait Alex, don’t! Please! I’m your mother!”

However, Alex immediately swatted his mother’s bottom with the studded leather paddle as hard as he could, causing her to cry out in agony. All the while he wore a sadistic grin on his face, while venting years with of frustration on the woman’s insanely curvy body.

‘It is precisely because you’re my mother that I’m treating you this way! Now take your punishment, bitch! You deserve it for leaving me!”

Alex continued to torture Diana’s body with any number of instruments which he had purchased from some website dedicated to BDSM. And as he did so, he crudely mocked the actions of a police officer.

“You got the right to… to… suck my dick, motherfucker!”

It did not take long before there were red marks on every part of Diana’s body, aside from her pretty face. Which was instead stained with tears. And Only after his mother begged him to punisher her with his dick instead, did Alex finally cease his assault.

“Please! I was wrong! I’m sorry! I should have never abandoned you! I’m sorry Alex! Mommy deserves to be punished! But please spare me the pain and instead punish me with your massive cock!”

Alex immediately tossed the whip in his hand away, where he the pulled his mother’s short curly hair back, and fulfilled her wish.

“That’s all I wanted to hear…”

After saying this, he shoved his massive twelve inch cock as deep into his mother’s twat as it would go. Though she had given birth to twins, Diana had never actually had sex with a man before. Yet, Alex did not go easy on the woman, and instead fucked her as roughly as he had ever been with a woman. At first, the ruthless pounding from such a large and thick cock had caused Diana to grimace in pain. But eventually, like every other woman Alex fucked, she began to moan in ecstasy, and demand more.

“More! More! Punish mommy! Punish her for being a stupid bitch!”

Alex continued to slap the bitch’s ass and fuck her well into the morning. Where she was found on the sofa, with a red body and cum leaking out of her pussy and ass. Interestingly enough, Shannon had decided to visit. Why had she done so? Well after not being able to cook dinner the night before, she wanted to make her new lover breakfast again especially since he had enjoyed it so much the previous morning.

However, after entering her sister’s penthouse, with the key that Diana had given her, Shannon was surprised to see the state that the woman was in. Yet she was not angry with Alex, instead she looked at her little sister and her nephew, who sat next to Diana, and pouted before expressing her jealousy.

“Damn Alex, you’re making me jealous… Shouldn’t you punish me as well for what I did to you during your childhood?”

Before Alex could answer this question, both of his sisters appeared in the living room and saw the sorry state their mother was in. It took the girls a few moments to realize what they were looking at, but when they did, they quickly voiced their own envy towards their mother.

“Aww… I wish I didn’t pass out last night… That could have been me!”

“Alex… Why didn’t you come to my bed last night? Was it because of our mother?”

Seeing how he had four women, all of which were his family members, longing for his cock. Alex simply scoffed and shook his head before posing a simple question to them all.

“How about we have some breakfast, and afterwards we can all do it family style?”

The four women had no idea how to respond to such shameless words. All they could really do was silently nod their heads in agreement. Thus, Alex relaxed for thirty minutes while the four women made him breakfast, before fucking them all in reverse gangbang.