Spending Money

Here is an original big brother/little sister incest story I wrote combining three of my favorite things: brother/sister incest, masturbation with a vegetable and deflowering a virgin.

This story is approximately 4,000 words and would be, at my current rate of commission costs, $40.

Title: Spending Money
Word Count: 4,015
Incest Type(s): Older Brother/Little Sister (approximately 19 years-old/14 years-old)
Summary: Siblings Toby and Allison go shopping. When little Allison buys a squash, big brother Toby suspects it's for her to masturbate with. When he catches her in the act, he's the one in for the surprise!
Notes: This is an original story with original characters and belongs to Daniel Kay.  This is a work of fiction and any resemblance to real people or events is unintended.

“All right, sis! Your brother is a money saving fiend! After setting aside what we need to take the bus home, we’ve still got three dollars extra we could spend on anything. That’s what you get for buying deals and bargain hunting.” Toby put his hand into his pocket and pulled out three crumpled dollars. “They’re all yours. You never get anything nice.”

Allison looked at the money but didn’t immediately take it, but her eyes had widened.

Toby grinned. It was probably the first time someone had ever offered Allison money. Even though three dollars wasn’t much, she knew Toby could use that money to buy himself something. He was stuck babysitting her, unpaid, for nearly a month while he was home from college and their parents were on the road, trying to earn money. She expected him to be as greedy as the rest of the family. “Go on. Take it.”

She tugged on the hem of the dress she’d nearly out-grown. “Are you sure?”

“Positive. Come on, let’s find something nice. What about a new ribbon for your hair?” He led the way through the outdoor market, looking at the stalls full of wares. “Or candy? You could get a lot of candy for three dollars.”

Allison trailed behind him, eyes wide in wonder now as she looked at the wares in a new light.

They passed booths full of mirrors, handmade shoes, woven purses and hemp jewelry, none of which interested Allison. They passed the candy stall and the one selling hot roasted cinnamon-sugar almonds, but she turned away from that. She stopped for a while at a store selling handmade wax candles, fingering one slender candle after the other, before eventually pulling herself away.

“What about a book? You like to read, don’t you?”

Allison glanced at the stall shelved with books, but her eyes soon drifted off the spines and on to a fancy glass paperweight the shop keeper had holding down some fliers. It was smooth and roughly shaped like an eggplant with many little bubbles frozen inside it. Toby stood back watching as Allison gently touched the thing.

“H-how much is this?” she asked the shop keeper in a small voice.

Toby knew without looking it was well beyond their budget of three dollars.

The shop keeper was a kindly looking old woman. She stared at Allison and then at the paperweight. “It’s twenty-six dollars, dear.”

“Oh.” Allison’s face fell. She stroked the paperweight again. “Do . . . do you have a smaller one?”

The old woman raised an eyebrow and glanced around until she saw Toby. She relaxed slightly then. “I do have one a little smaller. It’s twenty-two dollars, and a bit blue.”

“I only have three dollars,” Allison sadly said.

“You can’t get much for three dollars these days, my dear.” Watching her, the woman thought a little and leaned closer.

Toby pretended to flip through a book as he watched the old woman whispering to his little sister.

“If you’re after what I think you’re after, continue on down that way a little. There’s something Italian within your price range that I think you’ll like.”

Toby wasn’t sure, but he was fairly certain Allison’s cheeks were red as she hurried out of the stall past him. He had to break into a jog to keep up with her as she navigated through the stalls and into the farmer’s market, where huge amounts of produce was on sale.

She looked this way and that, and gravitated toward the banana display. She squeezed a few bananas, but her eyes kept roaming, clearly searching for something.

Toby said nothing, curious and baffled by her behavior. She passed up the sweet white peaches and the ripe, delicious strawberries. She passed melons as big as her head and tomatoes and potatoes. She drew up short suddenly in front of a large cucumber display, staring down at them with a puzzled expression. She picked one up and frowned. It was a large English cucumber, nearly as long as her arm with rough edges. Sadly, she put it back on top of the others.

Toby swallowed at the sight as pieces started to fall into place. He blinked a few times, trying to make himself stop thinking such dirty thoughts. He was a horny college student, but not everything was about sex! Allison just wanted some fresh vegetables . . . or a phallic-shaped paper weight . . . or one of those candles . . .

He blinked out of his reverie when he heard Allison give a little gasp of delight, redirecting his attention on her. She was now standing in front of a display selling Italian squash, and if his perverted thoughts were correct, he knew exactly why she was so happy.

The Italian squash were smooth and shiny, with one curved end and one stem end. They came in varying sizes, from small to large, but over all they looked like slightly above average green cocks. As Allison ran her hands over the display, Toby’s own cock gave a throb of interest.

He tried to quell the interest of his cock, but Allison quickly sorted through the Italian squashes until she had one in each hand. “I want these,” she said, turning around. “Please.”

Toby couldn’t help but notice that she was blushing.

“Squash?” he managed to say in a neutral tone.

“Yes, please.”

Toby glanced at the price. “They’re a dollar-nineteen each. That’s a lot of money for two vegetables.”

“<I>Please</i>, Toby.”

Toby swallowed hard again, but kept his voice calm. “Well, I guess mom and dad don’t buy you enough fresh vegetables. All right. Two Italian squash it is.”

He felt ridiculous standing in line to buy only two squash with a pretty little girl beside him during the transaction, but it was soon over and they were on the bus home. Allison never let the bag of squash out of her sight, clutching it to her chest any time someone passed her on the bus.

Toby wanted to be upset that his baby sister was becoming sexually aware enough to want such things, or angry with his parents for not realizing it and providing her with something, but he wasn’t. He felt lucky to be here in this moment to watch his sister crush two Italian squash between her little breasts every time someone walked by her. He felt lucky she was so sheltered and poor that she needed to sneak out with her big brother and buy vegetables to masturbate with.

He knew it was wrong to be so turned on by the thought of his sister in sexual ways, but he couldn’t help it. It was a lot less fucked up than some of the things he found himself thinking in his sexually charged college days, and, now that he really looked, he realized just how attractive his little sister was.

She was way too young for him to notice otherwise, but she was definitely not the skinny, gawky child he remembered when he’d left. Her breasts had come in slightly, and were even more obvious in her too-small dress because she wasn’t wearing a bra. Undoubtedly their parents hadn’t thought about that enough to buy her one, either. Her skin was clear and her hair was shiny. Her eyes were wide and bright and she had inherited a lot of their mother’s natural beauty.

He noticed he wasn’t the only person admiring how much of her legs could be seen as her small dress rode up her thighs every time she clutched her squash close. Toby took the vacant seat beside her, held his breath and gently tugged her hem down. The action sent a chill coursing through his sister and she stared at him with those lovely wide-eyes.

“Be more ladylike,” he whispered.

“S-sorry,” she gasped.

When they arrived at their destination, he ushered her off in front of him. He glanced back at the creepy guy who had been staring at her the whole time, but that man wasn’t watching her leave. His eyes were on the bus seat, which had a small but visible damp spot drying in the middle.

Toby’s cock swelled as he hurried off the bus, trying not to think what else beyond a bra his baby sister wasn’t wearing.

The walk back to the apartment was difficult, but allowed Toby to gain some control over himself. “Are you hungry?” he managed to ask. “We could get those cooked up right away, if you want.”

Allison’s eyes widened again at the words, and she clutched the squash to her chest again. “No! I mean. I’m not hungry yet. Actually, all that walking has left me tired. I think I’m going to go lie down for a while.”

Toby knew exactly what that meant, and what control he had over his cock was once again lost as it throbbed in interest. He unlocked the apartment door and watched Allison hurry through the dim hall and disappear into her bedroom. He stood in the doorway a while before flipping on the lights in the living room and closing and relocking the front door.

What was he going to do? If he stood outside her door, he could undoubtedly listen to whatever little sounds she made as she explored herself. Perhaps it would be better if he took a shower and tried to think of something other than his sister while he took care of himself.

Somehow he found himself standing outside of her door, listening to the silence. Had she already started? Was she really that quiet? What if she really was napping?

He stood there for what felt like twenty minutes but was probably only five, before finally making up his mind. He had to know. He had to <i>see</i> her. He could act surprised and quickly let himself out again, but he needed to know. “Allison,” he said, turning the door handle, “I’m coming in.”

She was on her bed, on top of her sheets, legs spread, pussy bared, grinding the squash against her clit. She still wore her tiny little dress, but it was hiked up out of the way now. “Toby,” she moaned as he entered, her head lolling to the side to look at him. She rubbed the end of the squash over her pussy hole, but didn’t push it in. “All this time,” she gasped, “you knew what I wanted it for.”

“Holy fuck,” Toby gasped. What had before just been a half-erection was straining against his pants now to stand up properly. His heart was suddenly pounding and his eyes were drawn to the sight of that squash as it spread his baby sister’s pussy lips open, circled around her clit and then slid down over her wet, clenching hole.

Allison moaned and shifted her hips, angling herself so Toby could have a better view. “Toby,” she moaned. Her legs spread open further and she pressed the head of the squash against her tight little pussy. “Watch me, please,” she gasped. “Please. Oh.” Her pussy finally began to swallow the head of the squash, the tight pink ring of her hole stretching as she forced the squash inside her. She whimpered again, pulled the squash out slightly, and then began forcing it back inside her hole. “Toby, Toby. Ohhhh!”

“Allie,” he managed, but could form no other words beyond that.

“With a squash,” Allison moaned. “Fucking . . . my hole. My virgin hole . . . while big brother watches.” She squeezed her eyes tightly shut and forced the squash in deeper. She let out a gurgling noise of delight and began to pump her hand, forcing the squash in and out of her. “So good,” she gasped, shuddering.

Unable to help himself now, Toby began to unfasten his pants. He let out a sigh when he freed his heavy cock from the confines of his pants, and began to stroke it even harder as he watched. This was wrong, but he no longer cared. His little sister was getting off, masturbating with a vegetable while he watched. If she was going to enjoy this, so was he.

“Oh God,” Allison moaned. “Come closer. Want to see it. Big brother’s cock.”

It wasn’t easy to walk, but Toby did, leaving his pants and underwear in a pile by the door. He dripped precum as he walked, which he picked up with his hand and helped slick his cock. “You . . . you like it?” he whispered.

“Yeeeeees,” Allison moaned and shoved the squash deep and hard into her pussy. “Yes! Oh! Fuck me with that big cock, Toby!” she cried, slamming the squash into her pussy. “Yes! Oh my God, yes!”

“A-Allie!” He pressed his knee onto the mattress, finding it hard to stand. He kept stroking himself as he watched his sister’s pussy swallow the squash all the way to the stem. There were tears in her eyes, but she didn’t stop pounding it into her pussy.

“T-Toby!” She arched her back, but she wasn’t coming yet, he could tell. “Oh! My big brother. Finally.” She reached one hand up and pinched her nipples through her dress. “Finally watching me. Big brother. Finally wanting me.” She scooted back on the bed, giving him room. “You want me, don’t you, Toby? Your baby sister? Your baby sister’s pussy?”

Toby’s mouth was dry. He licked his lips and could only nod. It was so, so wrong, and he didn’t know at all what was happening or how or why Allison was saying these things, but, oh yes. He wanted his baby sister right now; wanted to stretch her tight little pussy even more than that squash was.

“I love you,” she gasped as he knelt on the bed, positioning himself over her. “I always have. Ever since . . .” she trailed off and reached up, grabbing his shirt and dragging him down to kiss her. She kissed rough and hard, moaning into his mouth as their tongues met.

She reached between them and found his cock, wrapping her small, warm hand around his long hard shaft. She stroked him several times until he was moaning too. “Allie.”

“God.” She was panting hard now, her cheeks flushed, her eyes glittering. “Fuck me, please?” She tugged his cock and his hips instinctively lowered in the direction she was pulling him. “Please, big brother. Please.” She writhed beneath him, the squash still buried in her hole. “Baby sister needs big brother’s cock.” She stroked him. “You’re so much bigger than my squash.”

“And that’s too big for you,” he managed to gasp.

“So big,” she answered, stroking him. “Want to be filled. Want to be stretched. Waited my whole life for this, for big brother’s cock to fill me.” She reached down and began to pull the squash out of her. The head was slightly rounded and her whole pussy stretched as she tried to pull it out, refusing to let go. When it finally did, it made a wet, popping noise and she shuddered violently. “So empty! Toby!”

She threw the squash aside and grabbed his cock, pressing the thick head of his cock against her wet, swollen pussy. “Oh, God,” Toby moaned. Even after being fucked by the squash, she was so tiny and tight. He could still see the tight ring of her hymen straining to keep his cock out.

She was incoherent now, mewling and writhing on the bed, trying to spread her legs further in an effort to make her pussy big enough to swallow Toby’s cock. “Nownownow,” she finally cried. “Forceit,Toby,fuckmeharddoitnowplease!!”

Gritting his teeth, Toby pushed her legs back into the bed, nearly doubling her in two, and drove his hard cock right through the remains of his baby sister’s hymen. He felt the soft narrow walls of her virgin pussy stretch as his cock filled her. Allison screamed in pleasure and pain, but Toby hardly heard her. She was SO tiny and SO tight and SO wet. He had never, ever fucked anything like this before.

Allison began grinding her hips up into him, screaming as she did, but loving every second of it. Her ass and hips worked in circles, making the impossibly tight pussy feel even more amazing. Her inner walls were stretched too far by her brother’s cock to massage and pulse properly, but when he pulled out before driving back in, they tightened and he was able to stretch them wide open all over again.

She screamed nearly every time he did this, writhing against the hands that held her legs down, but working her ass and hips to fuck him at the same time.

“It’s too much,” Toby cried. “I’m hurting you!”

“Don’t stop!” Allison screamed. “Don’t stop! Don’t ever stop!”

It was all the encouragement he needed and he felt his balls tighten. “Oh god, sis! I’m gonna . . .”

“Yesyesyesyesyesyesyes!” Allison screamed and her ass and hips went crazy as she desperately fucked herself on her brother’s cock. “Fuckmefuckmefuckme, inside, Toby, come inside!”

Toby was going to pull out, but her hands came up and gripped around him, drawing him in. Her hold wasn’t so strong he couldn’t break free, but as soon as he had the IDEA of coming inside that tight narrow hole, he WAS coming inside her, shooting huge ribbons of come against her cervix, absolutely flooding his little sister’s tight pussyhole.

“Inside!” Allison screamed in ecstasy. “Inside! Big brother’s coming inside!” She went off in that moment, her body absolutely wracked with orgasmic spams. She twisted and shook, vibrated and convulsed. Her pussy began squeezing his cock hard, despite how stretched out it was. It wanted his cock and his come; the additional tightness made certain he couldn’t easily pull free, and the massaging pussy walls coaxed out even more come, milking him dry. Still Allison came, screaming and shuddering over and over.

It was beautiful and frightening and Toby wished he could come again because she felt so amazing.

When at last she subsided—though small orgasmic tremors still wracked through her occasionally—Toby looked down. His cock had softened inside his baby sister, but even flaccid he still filled her tiny hole. It was dizzing to think how big he had gotten and how much he had stretched her.

When he finally pulled out, an impressive amount of his come began to ooze out of her stretched out hole.

“Ohhhh,” Allison moaned. She shuddered with another little orgasm. “So empty. Big brother. Big brother’s cock. Big brother’s come.” Her fingers felt around on the bed until she found the squash she’d been masturbating with earlier. Without saying anything, she shoved it back into her pussy, sealing up the rest of the come inside her. Her legs were released now, and she squeezed them shut with the squash swallowed up deep inside her.

Toby sat back on his heels, panting. He pulled his sweat-soaked shirt off and stared down at his little sister. She had sweated through her dress too, so he could see her hard little nipples through the thin fabric. He thought about her tight pussy filled with his come and the Italian squash plug and shivered.

“What just happened?” he whispered to her.

“Mmm.” She reached up and rubbed his thigh affectionately. “I love you.” She smiled sleepily.

What they had just done terrified and slightly horrified Toby, but he kept his calm. It had been the best sex he’d ever had, and he’d been pretty wild in college. He wanted to run screaming into the street, but the rest of him wanted to keep calm and quiet in the hopes that this wasn’t a dream and he could have sex like that with his little sister again. “Since when?”

“Since always.” She closed her eyes, blissful. “I always thought of you like that. Always wanted you as my boyfriend. As my first kiss. As my lover. Always.” She opened her eyes. “Never thought you’d . . . you’d want me too.”

“Allie. You’re so young, and you’re my sister and,”

“Shhhh. I know. I don’t care.” She reached down and rubbed her belly, feeling the squash inside her. “I’ve tried not to want you, but it’s never worked. If I try thinking of something, or someone, else, I never, ever get off. If I think of you, I can get off in seconds.” She shivered as another little orgasm rolled through her. “Every time. I belong to you. She stretched slightly on the bed, displaying her blossoming body to him. “If you don’t want me, I will wither and die, but never take another lover. There’s no one else for me; now I’m certain of it. I am yours. I want nothing more than to be my big brother’s lover.”

“Allie.” He swallowed hard. Was this really happening?

“We could run away together,” she whispered. “Go somewhere no one knows us, so we can be married and do as we please. Or I can be your little secret. I can be my big brother’s mistress. You can lock me in a basement and only take me out to fuck. You can sneak home on weekends and fuck me in my bed while mom and dad sleep next door.” She squeezed her thighs together, shivering as it stimulated the squash inside her. “I can be your live-in maid. I can be a piece of furniture in your house with holes for fucking. I can be your wife, your girlfriend, your sister, your lover. Please, Toby. Love me, use me, fuck me. Please. Promise me. I’ll die if you don’t.”

Frightened but aroused by her words, Toby reached down, cupped her face and kissed her gently. “I promise. I don’t know what I’ll do yet, but I promise to fuck you again. I promise to use you.” He reached down and cupped her breast through her dress, then touched the curve of her hip and then her thigh. “I promise to love you.”

“Toby,” she whispered, and there were tears in her eyes again. She wrapped her arms around him, hugging him tightly. “Big brother.”

He shivered at her words and the embrace and what he was agreeing to. What a twist this babysitting trip had taken! “My baby sister.” He kissed her neck gently and laid her back down.

“When?” she asked, brightly.

“What?” Toby blinked. “When what?”

Allison smiled, her eyes shining early. “When will you use me again, big brother?”

Merriment and arousal shot through him and he laughed. “I need a little time to recover from that, sis. But, maybe later tonight, if you like.”

Allison carefully got up off the bed, careful to keep the squash from falling out, and gently straddled his thigh, so the stem of the squash just gently pressed into his skin. She rested her head against his arm and very gently rocked her hips, humping his thigh and vibrating the squash. “I think I can wait until tonight,” she breathily said, “if we’re like this until then.”

Toby smiled and slid an arm around his baby sister as she mewled and masturbated against his thigh. It had been an incredible day, and it was going to be an even more incredible night. He only hoped that he had a plan for what they could do before their parents returned home in a month.

THE END

Well, what did you think? I have considered continuing this story on, but I've been busy with other projects. What would you pay to download this story (or one of similar quality) assuming it wasn't available for free like this? $1.00? $5.00?

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