Work Header

The Pursuit of Pleasure

Work Text:

The story begins with a young human boy, "Riley", and his older sister, Lucy, an anthropomorphic cat. (From the webcomic "Better Days").

In this incarnation, Lucy's character is almost entirely re-written from Jay Naylor's, and Mat Sherer's versions. Used without permission. Written by: Nineball

Special thanks to everyone whom has left kudos on this story for me. Half of the reason for my creating these, is to have other people enjoy them. Even if it's just one person.

Cleaning a pellet rifle would likely be a chore to somebody else, but not to Riley. Even at eight years old, the boy had a flaming passion for guns, and anything related to them. He did not, however, enjoy trying to clean rust off from them. Lucy, Riley’s ten year old sister, had left his favorite rifle out in the rain and caused it to rust. She had brought it outside while she gave his room an unsolicited “organizing”. Fortunately, his mother offered to take him to get a new tomorrow. His train of thought was lost though, as he heard his sister coming down the hall and likely towards his room. As Riley expected, there was a series of knocks at his door.

“Open up, Riley! I’ve got a game we can play that doesn’t involve maiming you!” Lucy asked politely.

“No way! You’re not coming in here, you pest! You already ruined my BB gun, y’ain’t breaking anything else!” Riley yelled at the door.

“You shouldn’t even get an allowance to buy those with! Mom won’t even give me money to buy some new clothes I want! Oh yeah, and Mom said you have to listen to me!”

“Mom ain’t here!”

“She called me on the phone and said that I have to watch you!” Lucy countered.

Riley was beyond mad, he had to spend all day with his sister, and if he didn’t listen then he’d get it good from his mom. “It” wouldn’t be a new pellet gun either.

The boy put his gun down, and braced himself for the hell that waited at his doorstep. He walked over to the door, and unlocked it for her. The moment he opened it, Lucy had already begun her advance into his room.

“Wow, Riley, your room looks much nicer now that I’ve cleaned it,” Lucy praised herself.

“You just moved everything into the closet.”

“That’s where your garbage goes,” Lucy bent over to say to his face as she sneered at him.

Riley caught himself before he said anything he’d regret. He had to be around her all day until his mom got home. It wouldn’t be smart to make her mad. “What’s all this about a game?” Riley asked, deadpan.

“Oh, I’m so glad you asked. We’re gonna play the dare game!” Lucy cheered.

“You said it didn’t involve maiming me.”

“It won’t this time, I swear. Scout’s honor.” Lucy said.

“That doesn’t mean anything when a girl says it," Riley explained.

“Go to hell, Riley.”

“I’m already there,” Riley deadpanned again.

“Not yet you’re not. Now, let’s start playing,” Lucy said as she took Riley’s hand and brought him over to his bed.

Lucy climbed onto the bed and rested on her knees. Riley gave in and sat across the bed from her.

“I’ll let you go first, as a handicap,” Lucy taunted and started laughing at the jab she’d made.

“Well...I-...I!...I dare you to take off all of your clothes!” Riley managed to demand.

Lucy stopped laughing and stared at her brother with wide eyes. Riley immediately regretted what he said and looked away from her in shame.

“L-Lucy, I’m really sorry! I didn’t mean it! I-”

“Wow! When did you turn into a little weirdo? Get ready, I’m gonna be way more than you can handle, Riley!” Lucy declared as she began to remove her top.

Riley was blown away by his sister’s counter-offensive. He sat slack-jawed with rapt attention as he watched his sister’s double N’s drop free from the grip of her tight shirt. Her huge nipples were already hard, poking out loud and proud from the fur on her chest.

The cat gave him no time to appreciate the sight. She approached him, moving on all fours across the bed like a true predator. Having backed her prey into a corner, and trapping him against the wall, Riley got nervous.

“Whoa sis, take it easy, I didn’t dare you to do this!” Riley pleaded.

“Nuh-uh, I have to do the dare. Same goes for you, Riley.” Lucy said.

Riley’s sister stood on her knees, towering over her cowering brother. Tantalizingly slowly, she began to take off her skirt right in front of the boy’s face.

“You ever see a vagina before, Riley?”


“You wanna?”

Riley had no idea what that was, but he guessed that it was something under Lucy’s remaining clothes. The name itself sounded so foreign, exotic even, to him. With his child’s curiosity piqued, he couldn’t resist.

“Yeah...please…” Riley quietly accepted.

His sister smiled, and put her hands on the wall behind and above Riley. She looked down at him with that frightening, sly grin.

“You know what? You’re gonna do it, since you’ve never seen one before.” Lucy explained.

Riley nodded, and gulped a bit out of fear. Mustering his courage, he reached up to the top of his sister’s skirt, and slowly pulled it down revealing bit by bit of the place between her legs. She wasn’t wearing any underwear, giving Riley a full view of the fabled “vagina”!”

“Is that it, sis?” Riley asked.

“Sure is…”

Lucy’s vagina was only inches away from his face. Inquisitive, he touched it right in the middle with one of his fingers. The folds gave way to his digit, and he felt a warmth, followed by soft, wet tissue that had a lone bump on it.

His sister gasped sharply, which startled Riley.

“I’m sorry, Lucy! I didn’t mean to hurt you! Riley vigorously apologized.

Lucy began to giggle at him, and her eyes closed a bit, becoming a sultry gaze.

“I did my dare, Riley. Now it’s your turn. I dare your tongue to lick it. Inside and out.” Lucy whispered.

Using a finger was bad enough, but using his tongue would’ve been right out. However, Riley’s sense of honor made sure he’d see the game through. He had to go on.

“Alright, Lucy! Get ready, I’m gonna clean your...Vagina good! Riley exclaimed.

“Remember Riley, inside and out,” she reminded him.

Her lower body dwarfed Riley's in every way. It became especially intimidating as she leaned over him. Lucy's hips were already wider than her mother's, and her ass and thighs barely fit underneath her personally-hemmed plus-size skirt. More accurately, it could've been called a lower-bodysuit instead. Her vagina was just as imposing. It was puffy, tight, and only two inches away from the front of the boy's face. He thought it looked big enough to fit his entire arm inside. The unfamiliar nature of her body made him nervous, and he froze up.

"Uh, Earth to Riley, are you, uh, going to lick me or not?" Lucy nagged him.

She distracted him from his paralysis, and the boy was able to regain his grasp on the situation at hand. There was no turning back for him, now.

"Ok Riley, you can do this...Here goes nothing!" He thought.


Riley’s lips sucked as hard as possible on Lucy’s flower. He’d never done anything like this before, but he was a quick learner. Using his tongue to lick past her thick folds, Riley almost recoiled at the intense heat coming from his sister’s vagina.

“Oh goodness, Riley! Lick a little higher, please! Just below the top!”

There was a bump that Riley could feel. Using his intuition, he assumes that it’s the spot that made Lucy feel good. Licking up and down as fast and hard as he could, he focused all of his attention on it.

“Oh! Oh! My word! Riley! Yes! Be louder too!”

The boy puckered his lips around her folds, and sucked as hard as he possibly could. It was almost too big for his mouth to fit around entirely. Sloppy, obscene sucking noises filled the room, and it aroused Riley, too. His penis grew to its full length almost instantly from the din he caused. With the erection in play, his sucking and licking became even more passionate.

Lucy’s fists balled, and she pressed the top of her head against the wall. Unfamiliar to the pleasure, she wails, her moans rising and falling in pitch according to her brother’s tongue. The girl’s vagina began to contract around Riley’s tongue, and copious amounts of fluid flowed from deeper inside her depths. She grabs her brother’s head and forces it as deep as possible into her warmth. The boy is barely able to breath, but amused by her sister’s reaction, his motivation and cunnilingus only increases.

“Riley! Don’t Stop! Don’t you ever stop!”


Mouth open and mind blank, Lucy is overtaken by one of the first orgasms of her life. It’s immensely powerful, and all consideration for her brother’s ability to breath falls to the wayside. She howled continuously as Riley lashed at her vagina relentlessly during her most vulnerable moment. The cat’s legs buckle under the pressure of her climax, and she fell onto Riley’s head, pinning him to the wall. Though her over-endowed and soft thighs threatened to crush the boy’s head, and her pummeling thrusts crushed his face into her wetness, he held on and attacked her with all the intensity he could muster. The boy jabbed at her sensitive spot, and sucked on her with all of his might. The sound of his assault impressively competed against the volume of his sister’s moaning and screaming.

The cat’s orgasm died down, but only after an entire two minutes of hammering every fiber of her conscious mind. Riley, who was still eating away at his sister, decided to pull away and make a few jabs at Lucy. His sister’s vagina almost refused to release his tongue. It made a loud sucking sound as his tongue escaped, followed by a pop as he was released. From hair to his shirt he was covered in viscous liquids both clear and white.

Sis! Look at what you did to me! I’m a mess! My mouth’s all sticky now, too." Riley complained as he licked massive, copious globs of girl-cum from his face.

Lucy opted to say nothing, instead, she fell down onto her brother. Hugging and purring against the side of his face, ignoring the mess of fluids that clung to her fur from contact. She moves to face her brother, sitting in his lap. Without warning, she leaned in and began to vigorously make out with Riley’s. Her hands grabbed the sides of Riley’s head again, forcing him to her affection. Upon her embrace, her bare double K’s were crushed into her brother’s chest, and rubbed around with her movements. The cat’s kissing and sucking is just as loud as his was before, though she preferred to draw out the sounds rather than focus on speed. The boy found the kissing sounds embarrassing, but he knew that trying to fight it would be hopeless. For the time being, he was doomed to be a prisoner of his sister’s humiliating face-sucking.

Breaking the kiss, albeit leaving behind several trails of gooey fluids between them. Exhausted, Lucy gazed at her brother with the same loving eyes as before. Riley blushed even harder in response, but returned the gesture. He’d loved the experience, and so longed to please his sister again. Though, her wordless move to slide down his sweats and trousers clearly promised him much, much more...

The cat’s little brother didn't struggle, and his zipper was down in an instant. He didn't know what she was doing, but had a hunch that his member was likely involved in her plans. The little boy waited, excited for whatever his sister would do to him next.

"It's a bit smaller than I thought it'd be, but...I think it'll work."

Riley had no idea what she’d meant about his length. He thought it was plenty big, about four inches long. The clear liquid that dripped out from the top puzzled him, though. He'd never seen that before. Regardless, it felt good to let it leak out.

Taking a hand down to her flower, Lucy retrieved a handful of her honey. She rubbed it all over, and into her little brother's rod. With it wet and slippery, Lucy held Riley's penis still, and positioned herself above it.

"Here comes the best part, Riley. This is where we have a lot of fun!”

No words were spoken as Lucy sat down onto Riley's shaft. The boy gasped in amazement and pleasure as he watched his sister's over sized warmth easily take his rod all the way inside of it. His entrance accompanied by another wet, and loud sound of suction from his lover’s flower. With his member devoured entirely to the base, both siblings closed their eyes and relished each other's warmth. The girl leaned in close to her brother, intent on whispering her instruction and encouragement into her brother’s ear.

“How do I feel, Riley? Amazing, right?”

“Ye-!...Yes, sis! You feel amazing!”

“I’m going to start moving, now. Hug me by the waist, and hold on tight.”

Riley listened, and nestled his head between his sister’s cozy breasts.

Lucy ran a hand across the top of her little brother’s head as she lifted herself above and away from his length. Then, she came back down, causing both of them to moan from the feeling.

Riley would only last for another thirty seconds of their movement, before a strange sensation began to build up inside him. The boy’s penis felt better than ever before, and it only became stronger. He had no idea what it was, and it frightened him a little bit.

“Sis! I think I’m gonna pee…stop...”

“That’s not pee, it means...I uh, need to go...faster.”

Her pace quickened, and the movement of the cat’s thrusts lost a bit of its distance. In the final moments before his first orgasm, Riley himself began thrusting upwards into his sister. Reassured by her, he freed himself to move as he pleased. In no time, he closed his eyes, seeing stars as a powerful orgasm slowly dominated his perceptions. He didn’t want to see, or hear, the boy just wanted to feel. Massive waves of pleasure and warmth overtook him, body and mind. Feeling something amazing being let loose from his length, his climax reached its peak. There was no better feeling in existence to him.

His orgasm reached its ceiling, and started to come down bit by bit. When he came to, he looked up from the blackness of his lover’s chest. The first thing he saw was his sister’s face, happy, and glowing with love.

“I love you so much, Lucy.”

“I love you too, Riley”. She whispered.

Worn out from their lovemaking, Riley pulled his sister down to the bed’s sheets with him. With his sister’s soft breasts around his head, and her warm body enveloping him, he closed his eyes and lost himself in Lucy’s embrace.

“I think you’ve got the right idea, a cat nap is...certainly in order...” Lucy said between a yawn.