Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
Click here
"Who knows? Had you waited just another minute, maybe you would have caught me topless or even naked," she said laughing. "You could have masturbated the rest of your perverted life over what you may have seen of me," she said in her sexiest voice along with a big laugh while teasing him. "Only, you weren't quiet enough and were too impatient. You opened my door too soon. If only you had waited, God only knows what you may have seen of me," she said.
While fanning her face with her hand as if she was heated up from embarrassment, she spoke to her brother as if she was Tara in Gone with the Wind and she was talking to Rhett Butler. After giving his big sister a sexually excited look while imagining her in her panties and bra, topless, and naked, he gave her a big Cheshire cat smile.
"I would have liked to have seen you topless or naked," he said.
He was dreaming if he thought his sister would show him any part of her beautiful body. He was dreaming if he thought his sister would strip off her clothes in front of him. Before she graduated college, he'd have to be an audience member at a Spring Break wet T-shirt contest to have seen his sister' topless and/or naked body. He was dreaming if he thought his sister sexually and incestuously wanted him in the way he sexually and incestuously wanted her. Instead of being her annoying, pervert of a little brother, he'd have to be one of her hot boyfriends for him to have any chance of having sex with her. She rolled her eyes and let out an aggravated sigh.
"God, you're such a pervert," she said. "Why are you such a pervert?"
He gave her a fuck you nod of his head with a shrug along with a cynical smirk.
"You have a lock on your door. Why don't you use it? I wish I had a lock on my door for Grandma to quit bothering me. As if she knows what I'm doing, she always opens my door while I'm masturbating. If you don't want me to catch you undressing, you would have locked your door. Yet, this is all bullshit," he said not believing anything that she said.
She looked at him with hurt mixed with anger.
"Eww, Grandma caught you masturbating? That's too much information," she said waving her hand at him while making a bitter face. "You're right though. I should have locked my door but I thought I could trust you, my own brother, from invading my privacy and violating me," she said. "Yet, with you such a pervert, I should have known better. You're unable to control yourself from being such a dickhead."
He wondered what she meant by violated. Before he could even ask his sister his real question, the reason why he was standing in her bedroom, he persevered. Ready not to take no for an answer, he had the cash burning a hole in his pocket to hopefully persuade Jennifer to undress and strip naked in front of him.
"I know you're as much of an exhibitionist as I'm a voyeur. I know you're just as horny and incestuously attracted to me as I am to you," he said. "I know you're as much of a whore as I'm a pervert."
She pushed him back towards her door.
"A whore? Did you just call me a whore to my face? Are you crazy? How dare you call me, your own sister, a whore? Have you lost your mind? What's wrong with you? Sexually attracted to you my ass, my own brother. I'd never have sex with you. How dare you? Fuck you! Get out! Get the fuck out of my room," she said.
She pushed him aside to walk by him to open her bedroom door. Then, she pushed him back in her doorway.
"Wait. I need to talk to you," he said.
An immovable object of sexual, incestuous lust, she pushed at his chest in her effort to evict him from her room.
"Frigging pervert. If we were stranded on a desert island or if you were the last man left on Earth, I wouldn't be sexually attracted to you," she said. "Get out! Get out of my room! Now! Go! Leave!"
# # # MyMomChristinetheIncestWhore # # #
"Wait, before I go, I need to ask you something," he said.
She tried closing the door on him while pushing him out of her bedroom but he was too big and too strong to budge him.
"Ask your question from outside of my bedroom door," she said.
Still not taking no for an answer, Jason stood his ground by keeping his foot in her door. Always bullied by his sister before, with her always mean to him, for the first time, he stood up to his big sister, Jennifer. He needed to give her his incestuous, sexual proposition. He needed to tell her what he so wanted. With his fat wads of money weighing down his pockets, he was prepared to give her money, if she agreed to strip naked. He was prepared to give her a lot more money if she agreed to had sex with him. As if he was a Mafia Boss, Don Jason, he wanted to make his sister an offer that hopefully she wouldn't refuse.
"I'll give you one-hundred dollars in cash, right now, if you let me watch you get undressed," he said stepping inside her room again when she let go of her door.
She made a sick face as if she was about to vomit while looking at her brother as if he was nuts.
"What? Watch me undress? Are you crazy? No! Why would I do that? I'm your sister, you pervert," she said before falling silent as if rethinking his offer for her to earn an easy one-hundred dollars. "Besides, where are you going to get a hundred dollars? As if you're still in high school, you need Mom to pay for your books, for your lunch, and give you bus fare back and forth to college," she said with a mean spirited laugh.
He shrugged off her insult and persevered.
"As I said before, I'll give you one-hundred dollars in cash, if you let me watch you undress," he said.
# # # MyMomChristinetheIncestWhore # # #
Like his MILF of a mother, like her sexy daughter, in the way his mother once did, his sister had a shapely body. His mother, Jessica, still looked hot but his sister looked even better. Jennifer had one Hell of a body. With his sister bragging to her friends and potential boyfriends on the phone that she was a perfect 36-24-36 with C cup breasts that were too big for her bikini top, if he was to guess, he'd guess his sister was a small D cup. If the magazine still had topless and nude pictures, she could pose for Playboy.
Something that ran in the family, just as his grandmother and mother had big tits, his sister had big tits too. Something else that also ran in the family, just as his grandmother had full, red lips, and a very pretty face, albeit wrinkled now, so didn't his mother and sister have full, red lips and very pretty faces. Something else that ran in the family of females, just as his grandmother was a whore, his mother was a whore, and his sister was a whore. Enveloped in a family of whores, yet the only one he had ever seen anything of was his grandmother.
He was physically ill when thinking of his grandmother in her huge bra and granny panties, topless, or naked. Yet, having seen old photos of her, he could only imagine what his grandmother must have looked like when she was younger. If he thought his sister and her mother were pretty and shapely, his grandmother was even prettier and shapelier. He wondered if he could have sex with his grandmother while holding an old photo of her in his hand and pretending that she still looked like that.
With him having already seen his grandmother's naked breasts, three generations of tits, just as he'd love to see his sister's naked breasts, he'd love to see his mother's naked breasts too. Trying to imagine what his mother's and his sister's naked breasts would look like after seeing his grandmother's naked breasts, he couldn't even imagine how better, firmer, and higher up their breasts would be. Without a doubt, prepared to offer her so much more, it was well worth a hundred dollars to watch his sister undress. Without a doubt, prepared to offer her so much more, it would be well worth giving his sister money for her to agree to have sex with her.
Always masturbating in his room, he was sexually and incestuously attracted to both his mother and his sister. In the same way that he always masturbated while imagining his sister without her clothes, he couldn't even count how many times he had masturbated over imagining his mother in her bra and panties, topless, and/or naked. Again, in the same way that he masturbated while imagining his sister fucking and sucking him, he couldn't even count how many times he had masturbated while imagining his mother having sex with him too.
# # # MyMomChristinetheIncestWhore # # #
She looked again at him as if he was nuts.
"A hundred dollars?"
She made a bitter face. As if she was deciding which door to pick on Let's Make a Deal or the price of an item on The Price Is Right, oddly enough, she looked as if she was considering his offer.
"Yep. I'll give you one-hundred dollars to watch you undress," he said again.
As if the bubble burst of her making an easy one-hundred dollars, she looked at him as if he was crazy.
"You'd have to pay me a lot more than one-hundred dollars to watch me undress this body," she said with a dirty laugh. "Besides, where are you going to get a hundred dollars? You have no money. You don't even have a job," she said with an emasculating laugh.
He pulled a fat, loose roll of one-hundred dollar bills from his pants pocket and peeled off one. She stared at the wad of money that filled his hand.
"I have money," he said holding a one-hundred-dollar bill over his head. "Is this enough for me to watch you undress?"
As if she was a sexy prostitute and he was a John with deep pockets, she looked from him to look down at his hand stuffed full of one-hundred-dollar bills before looking back up at him.
"Where'd you get all of that money?"
He gave her a smile as if he had picked the perfecta in a horse race, won big at a casino, or won the lottery and had already collected the cash payout after taxes.
"I found it," he said.
She looked at him as if he was insane.
"You found it? Found it where?" She made a face of disbelief. "In this neighborhood? No way! Tell me. Where'd you get the money? Who did you have to kill?"
# # # MyMomChristinetheIncestWhore # # #
Instead of making eye contact with his big sister, he stared at the impressions her big breasts made in her blouse. Instead of making eye contact with her little brother, she stared at the fistful of one-hundred dollar bills in his hand. In the way he looked at her tits and she looked at his money, they each proved Jason's unproven assumption, sex for money and money for sex.
Nonetheless, nothing new there, he was always staring at his sister's big breasts through her clothes in the same way he was always staring at his mother's big breasts through her clothes. They both had such big tits, at least a C cup, definitely a large C cup, maybe even a small D cup. He'd love nothing more than to see his sister's and/or his mother's naked breasts. He'd love nothing more than to see his sister and/or his mother naked. He'd love nothing more than to have sex with his sister and/or his mother.
Whether with his sister or with his mother, something he had a habit of doing without him even realizing that he was doing it, he undressed them with his eyes while staring at their breasts. He imagined them without their blouses and standing before him in their bras. He imagined seeing their long, line of cleavage and their meaty breasts jiggling like firm gelatin with their every move.
Then, he imagined them without their bras. He imagined their naked tits. He imagined their pink areolas and their pink, erect nipples. He imagined both his sister and his mother topless before imagining them naked. He imagined having sex with his topless sister before imagining having sex with his naked sister. He imagined having sex with his topless mother before imagining having sex with his naked mother. In the way he always undressed them with his eyes, he was doing that now with his big sister.
# # # MyMomChristinetheIncestWhore # # #
Hoping to entice his sister with money, a lot of money, he gave her a sexy smile.
"I found it," he said again.
In the way he continued staring at the big impressions her breasts made through her blouse and bra, she continued staring at the wad of money he held in his hand. Then, staring up at him with her big, brown, beautiful eyes, she changed from being his bitchy sister to being his sexy sister. Lighting up him and the entire room, as if welcoming her baby brother home from war, she gave him a big, warm smile.
Sex for money, in the way he was mesmerized by the thoughts of his sister without her clothes, obviously, his sister was mesmerized by his handful of money. With him now having a lot of money and her having such a shapely, sexy body, maybe they could make a deal. Money for sex, perhaps they could come to sexually satisfying and financially agreeable terms for her to strip naked. Sex for money and money for sex, maybe his sister would even have sex with him.
"Where'd you find that much money?"
He laughed as if he was already delirious with the sexual anticipation of watching his sister undress and having sex with her naked body. Just as he knew how big of a whore his sister was, he knew how much his sister liked money. Whores and money go together like hands and gloves and shoes and feet. You can't have one without the other.
More importantly, what worked for him would surely work for her. He knew how little money his sister had. Willing to negotiate with her, if she willingly got topless and/or naked in front of an audience of drunken men during a wet T-shirt contest for prize money, he knew she'd undress for him for the right amount of money. He knew he not only could persuade her to get naked but also he hoped he could persuade her to give him sex.
"Right outside. When I came home tonight it was right there on the sidewalk in a brown, paper bag," he said. Not wanting to ruin his chances of having incestuous sex with his sister, he chose his words carefully. Instead of saying, as if coughed up from Hell, he said, "As if dropped from Heaven, I couldn't believe it."
She looked from him to look at his fistful of money again.
"Oh, my God. I don't believe it," she said as if she had found the money herself and as if the money was hers.
He smiled at her with pride.
"At first I thought it might be a bag of trash," he said. "Then, I thought it might be a bomb. Then, when I opened the bag and saw all of that money, I thought it was counterfeit money but it looked so real. I looked around to see if anyone was watching me before I ran down the alley with it and came in by the back door," he said. "Once safely in my room, I checked the money with that special marker that I bought to check for counterfeit money at the yard sale we had last month."
Not removing her eyes from his fistful of money, she stared at the money as if she had just won the lottery too. She asked her question without removing her eyes from his wad of money.
"How much is there?"
When he reached in his other pocket and pulled out another wad that was equally as big, her eyes bugged out of her head. Then, as if she was a starving woman, a little saliva was evident at the corner of her mouth. As if she was already having sex, with her face flushed and her breathing quickened, she was already aroused, not by him but by his money.
"I don't know. I haven't counted it all yet. There's too much money, so much money to count, but it's a lot. I have fifty-five more rolls like these two sitting on my bed and another three in my pockets," he said. "I counted one roll that had five-thousand dollars. I'm guessing that there's five-thousand dollars in each roll. Sixty rolls times five-thousand dollars would be three-hundred-thousand dollars."
He stared at his sister's tits again while she stared at the money he held in his hand. Normally denying him from ogling her, instead of folding her arms across her breasts in the way that she always does whenever he stares at her tits, this time she didn't. Instead, as if sexually teasing him, she took a big breath and stuck out her chest even more. Then, with the nursery rhyme "What are Little Girls Made of," coming to his mind and playing through his head, his sister acted as if she was suddenly injected with sugar and spice and everything nice. Obviously, as much as she was a whore for sex, she was a whore for money too.
'Wow,' he thought. 'Instead of her being the bitch that she always is to me; she was actually acting nice to me.'
She gave him a sexy smile and a naughty look while putting a loving hand to his chest.
"May I have some money, Jason? Please? I need a car," she said giving him a big smile while batting her big eyelashes. "Pretty please?" She gave him that smile that made her so much more beautiful. "I need a new Apple iPhone. Now that I graduated college and am working, I need a whole new wardrobe," she said flashing him that smile again while batting her eyelashes at him.
Whenever his sister smiled like she was smiling now, she reminded him of Eva Mendes. She was being nice to him in the way that only his sister could whenever she wanted something from a man. Always sexually attracted to her, he liked her even more now that she wasn't being such a bitch. Instead of always being so mean, nasty, and short with him, he wished she was always this nice to him.
Accustomed to using men for money who used her for sex, she was as much of a whore for sex and for money as his mother was. With his mother working as a cocktail waitress and with her always coming home late with a pocketbook full of unusually high tips, he suspected his mother had served men more than cocktails after work. In order to make ends meet, he suspected his mother moonlighted by serving cocks instead of cocktails by giving hand jobs and blowjobs to men willing to pay to play.
"Sure," he said. "I already told you. I'll give you one-hundred dollars to watch you undress."
She made a bitter face again. Oddly and encouragingly enough, instead of saying no, she was negotiating.
"A hundred dollars? Now that I know you have all that money, Jason, you'd have to pay me a lot more than one-hundred dollars to watch me undress," she said with attitude.
Excited that she didn't reject his incestuous proposition by saying no, obviously she was willing to negotiate her price to undress. He counted out two, crisp, one-hundred dollar bills.
"Okay. Sure. No problem. I'll give you two-hundred dollars to watch you undress," he said prepared to give her so much more.
She made that same bitter face again.
"More," she said staring down at his hand. "I want more than a lousy two-hundred dollars for you to watch me undress.
Ah, there's his bitchy sister again. He knew her being nice wouldn't last, especially when it came to money. He counted out five, crisp, one-hundred dollar bills.
"More? Okay. No problem. How much more? How's this? I'll give you five-hundred dollars to watch you undress," he said.
She made the same bitter face that she made twice before.
"Five hundred dollars? That's not enough. You'd have to give me more than that to watch me undress this beautiful body," she said moving her hands slowly down her body as if she was a Price Is Right model showing him a showcase.
Playing her game, he looked at her as if she was nuts when he was the nutty one to proposition his sister to undress for money. Besides with him having every intention of sharing his money with her by giving her and her mother one-hundred-thousand dollars each, it was more fun giving them his money in this way. Making them work for the money, he not only hoped to see his sister and mother naked but also he hoped to have sex with his sister and mother.
"If not one-hundred dollars, two-hundred dollars, or five-hundred dollars, how much more would you want to allow me to watch you undress?"
Seemingly fixated with the money, she stared at the money before staring up at him and before staring back down at the money.
