I will warn you that I am not a very good writer, nor a very descriptive one. So read at your own risk. Also, the characters in this are older than they are when they appear in the show. However, not that much older (they’re not, like, thirty years in the future). And yeah, it’s an older season, but it is my favorite season, and May is (in my opinion) the hottest Pokemon Girl trainer on the show, so I made her the main point. No copyright infringement intended. I simply wanted to read a certain kind of story, I couldn’t find it, and so I wrote it. Again, it’s not good, but I think it’s fairly fappable.
“AAAAAAH!” she screamed, “GET OUT OF HERE!!!” A boy in a green shirt and thick glasses ran away from her yelling and covering his eyes. The reason for his disgust was evident; lying on the ground, with a young man lying on top of her and forcing his cock into her pussy, was his sister May. “Oh Ash,” she’d been moaning, “oh more, please. Deeper!” Then she’d seen him, Max, staring in disgust and bewilderment at the tangled two-some. Every word cut into him like a razor. His sweet, idiotic sister was actually having sex with the boy he’d thought was his best friend!
Max found a small break in the trees and sat on a stump with his face in his lap. A thousand different emotions were running through him at once. Betrayal, anger, hatred, fear, sadness, grief, and… yes, it was there… lust. He shook his head. Surely he couldn’t seriously be turned on by his own sister…
May scrambled quickly up, leaving Ash to tumble to the ground. “WHAT TH-“ He shouted, and then he realized that she was crying. “What’s wrong May?” he asked. She turned toward him.
“Didn’t you see what just happened!?” She shouted. Ash shook his head, completely confused. “Max just saw us fucking!” Ash’s jaw dropped. “WHAT!?” He shouted. “Oh no. This is bad. This is really, really bad! Maybe if I talk…” May cut across him. “No,” she said, “I’d better do it. He’s my brother. He has to forgive me. You, on the other hand, he may not forgive so easily.” Ash hesitated, and then nodded reluctantly.
May quickly got on her clothes and ran off into the forest, leaving Ash by himself to panic quietly. She wandered through the trees, and finally she saw him; sitting alone on a branch. He looked just like he always had, since they were little kids; mopey and confused. Of course, and she would never admit this to him, he was far smarter than she was, or at least more knowledgeable about Pokemon. But she was more devious, and May was sure that she could talk her brother into forgiving them.
She went over and sat down quietly next to him. He sat up quickly when he heard someone sit down. “WHAT ARE YOU DOING HERE!?” He shouted incoherently. May pulled him into a hug. Try as he might to escape her grip, it was stronger than his, and finally he gave in and let her hug him.
“Max,” she muttered, “oh Max.” He grumbled. “It’s all going to be alright. I’m older than you, so there are things which I can do which you just can’t. You need to understand that it is my choice if I want to have sex… Oh Max, grow up!” Max had exclaimed angrily. She patted his head. “One day you’ll understand Max. You’ll have the same urge. Though,” she said quietly, “I believe you already do.” He finally managed to extricate himself.
“WHAT!?” He yelled, “I DO NOT!” May giggled and pulled him in again, laying his head against her breasts.
“Oh no?” She said. “Then why did you take that picture of Misty from Ash’s backpack?” Max blushed, and May continued. “And why do I sometimes catch you staring at my ass?” Max forced her grip off of himself again and glared at her. “I d-do not!” He stammered. May giggled again. “What’s wrong Max? Ashamed that you find your sister’s ass beautiful?” Max looked down in defeat. She rubbed his head.
“It’s alright, Max. It’s alright to think I’m hot.” She stared down at him. “In fact, I think you’re pretty cute too.” He looked up in surprise. “Oh yeah. I have sometimes imagined… well, let’s just say that my mind is just as dirty as yours.” She hesitated. “You know what? Yeah. Let’s get it all out in the open.” She took a deep breath, and let it out slowly. “I think you are cute. And I have sometimes masturbated thinking about you. I like to imagine you fucking me at night sometimes. And you know what? When I was fucking Ash, I was imagining you.”
Max stared at her in shock and embarrassment. He looked down and mumbled something. “Oh come on.” May said, “I shared my feelings with you. Now you share yours with me.” Max looked up at her and nodded. “Okay,” he said. “I think you are amazingly hot. I do stare at you. And yes, I jack off thinking about you. I know it’s not right, but… I do. And when I cum thinking about you, it is so intense… Lord, I just love your body. Your… but, you face… but especially, your boobs. Oh my god, I just want to stick my face in your chest and lick, and nibble on your nipples, and…” He looked down, and the image on his face was one of humiliation at his outburst, and aggravation that he had let out so much of his inner thoughts.
May sat there, trying to process all this information. But in all her bewilderment (she hadn’t realized just how perverted her brother was) there was one thought at the tip of her mind: he thought her boobs were beautiful. She had always thought that they were too small, and Ash wasn’t exactly a “tell you how beautiful and hot you are” kind of guy, so much as a “Misty was tighter than you” kind of guy. Sure, he was kind most of the time, but when it came to sex, he could be a real bastard.
“You really like my boobs?” She asked. He looked up in amazement. “Of course!” he exclaimed. “They’re perfect!” She thought for a minute, and suddenly she had an idea. A fiendish, horrible idea. But an idea which she could not leave behind. “You wanna… you wanna see them?” She asked. Max looked at her. “I kind of already did. You know, earlier…” Now it was May’s turn to blush. But she tried again anyway. “I mean… would you like to see them, and, maybe, you know… feel them?” Max’s eyes shimmered. “For real?” She nodded. “Well, the OF COURSE!”
May giggled at his excitement, and slipped her shirt off. She stood in front of him wearing just her shorts and her bra. “I need a little help unhooking my bra, if you wouldn’t mind.” Max went around behind her and unhooked her with shivering hands. She let the bra fall away to the ground. Max slowly came around her, and laid his eyes on the most beautiful site he’d ever seen: his sister’s bare boobs, out in the open just for him. He gingerly reached a hand out, and she let out a little laugh. “Go on,” she said, “you can touch them.” Max slowly, as if in a dream, cupped his sister’s right breast in his hand. It was so warm and soft. He could feel the tense little nipple digging into his palm.
May shifted a bit. Max rubbed the breast, moving his fingers down to her nipple. It was pale pink and stuck out about half an inch. He gently twisted the nipple, back and forth, back and forth, between his fingers. The friction he created made May shift slightly, and breathe a little more shallowly. She closed her eyes. “Do the other one.” She said softly. Max nodded, and moved his left hand to his sister’s other breast. He began twisting that nipple, and making circles around the right one, caressing May’s areola. She breathed a stuttering breathe. Something was different about this. It felt… better, than when Ash grabbed her boobs. They felt: more tender. She arched her back.
Max realized that he was making May feel really good, and he decided to take a chance. He slowly, so she wouldn’t notice, lowered his face to her right breast. He moved its nipple into his mouth and began sucking gently, while licking around the tip with his tongue. May’s eyes shot wide open, but it felt too good to stop. She closed her eyes again, and placed her hand on the back of his head. Max smiled around the nipple and moved his attention to his sister’s left breast. May gave a soft moan in response to her brother’s adoring mouth. Then she opened her eyes and pushed him away.
“Max,” she said, “Do you wanna see more?” Max’s eyes widened, and he nodded rapidly. May smiled. “Okay, then.” She pulled down her shorts and stepped out of them. Then she turned around and bent over, showing her butt. Slowly she pulled down her panties, revealing more and more of her beautiful body. As the panties came down, Max could see her ass cheeks, and then the back of her bloated, dripping pussy. If the boner in his pants could have gotten any harder, it did at that moment.
May slipped her panties off and held them aloft. She turned around and, dropping the panties on the ground, posed in the sexiest pose she could think of. Max’s legs wobbled. The most beautiful girl he’d ever met, and his sister to boot, stood completely nude in front of him, just for him. May spied the tent in his shorts and gave a little pout. “It’s not fair if you can see me naked, and I can’t see you!” Max nodded quickly and started stripping, but May laid a hand on his shoulder. “Stop,” she said, “I want to do it.”
She grabbed the bottom of his shirt and pulled it up over his head. Then she bent down and began to undo his shorts. She hooked her fingers through the belt loops and pulled them off. Now all that stood between them and total nudity was Max’s boxers. These, too, were discarded. Now his erect manhood was directly in her face. It was smaller than Ash’s, about six and a half inches, but it was thicker too. Much thicker. May gasped; her brother was rather well-endowed.
She looked up at his amazed face and gave him a sexy wink. Then she wrapped her hand around his stalk, and began to lick at the head. Her tongue curled around the head, slurping up and down the hole at the top, curving around the thick, purple-pink body, and the tip of her tongue rimmed around the edge. Max’s legs were really weak, and he almost collapsed. It felt really good. Finally, May began sucking on the stalk as her tongue took care of the head. She got it all the way to the back of her throat before gagging on the head. Suddenly, Max grabbed the back of her head and began thrusting. Not hard, but none too softly. She pulled herself free of the boy’s cock and looked up at him. “Ha-ha! Don’t do that, silly, or you’ll finish too quickly!”
Max nodded. “Can you do more of the back-of-the-throat stuff?” She nodded and went back to sucking his dick. After a little while, Max began to moan and started thrusting again. When it finally got to the point where it seemed like he was going to cum, May pulled away. “Not yet, Max.” She winked at the now aggravated boy. “Now it’s time for you to do something more for me.”
She laid down on the soft mossy ground and spread her legs. “I want you to use your mouth on me, Max.” Ash had never eaten her out before. He always said it was gross. She wanted to try it out. “Don’t worry, I’ll tell you what to do. But I need you to try this.” Max got down on the ground and laid his face near his sister’s pussy. “What do I do?” He asked. “Try licking the outside.” Max complied, licking up and down her moist, swollen slit. There was something about the way she smelled down there that made him go crazy. He lapped at her pussy, moving his tongue freely from the inner lips to the outer. May gasped and clawed lightly at the ground. Max tapped at the little button which was sticking out, and May let out a strong gasp of air. “Too strong Max. Don’t do that yet.” Max nodded and returned to simply lapping at her slit. Occasionally he would worm his tongue into the pussy itself, and that would make her squirm around.
He decided to try the little button again. He put his lips around it and gave it a little suck. Then he released. Then he sucked on it again. And he released. May was moaning at this point, and he decided to move back to the vagina itself… for now. He began to push his tongue into her more vigorously, basically fucking her with his tongue. May moaned and squirmed on the ground, and then her hands were on the back of his head again, holding him firmly over the sacred garden which was her pussy.
Max moved his head up a little, back to that little button that she seemed to like so much. He circled his mouth around it and began sucking, softly at first, but increasing in pressure. He began flicking his tongue over the button every few seconds, from different angles. At the same time brushing her slit with his fingers. He began sticking a finger into the vagina, penetrating her shallowly. He discovered a spot which was more rough than the rest of the inner wall, and rubbed at it. The effect was immediate. May’s back arched and her moans became interlaced with words and sentences. “Oh yes; yes, yes, yes!” and “Oh my God, it’s so good!”
After a short time, her sounds got progressively louder and louder, until finally she grabbed the back of his head and pulled his face forcefully to her pussy. She was screaming and shaking, her whole body seizing up like she was having a seizure, and had no control of her muscles. The inside of her pussy was doing the same thing, and Max’s tongue (which had gone back to orally fucking her) was trapped between two walls as hard to move as cement, and a delicious liquid was pouring into his mouth. Finally, after what felt like an eternity, she stopped shaking and lay on the floor, breathing deeply. Max swallowed the liquid May had squirted, and waited for her to recover. This, he rationalized, must be the female orgasm. He had to admit: he was jealous.
Finally, May came around. She sat up and looked at him with amazing love in her eyes. “Thank you, oh Thank you! No one’s EVER made me feel that good!” And she lunged forward and grabbed him into a hug. Then she laid back on the ground and said “let me recover for a bit, and I’ll make you the happiest guy in the world.” Max was happy to sit there for a minute, imagining the up-coming bliss.
Finally, May called Max over to her. “You know what to do” she said, and spread her pussy lips with her fingers. “Just lay down and stick that big cock of yours right here!” Max was trembling with excitement and anticipation, and laid on top of his sister, trying not to put too much weight on her. He managed, with her help, to line up his cock head with her hole, which was so hot just on the tip of his dick that he almost came then and there. May placed her hands on his butt and steadied him. “Easy tiger,” she said, “take it nice and slow.”
Max gradually sank deeper and deeper into that hot, moist place which men would kill for. And now he knew why. The feeling was beyond compare; beyond description. It was so tight, and so warm, and so wet, and so… everything you could ever want to feel on your penis. He started to pull out and push back in, thrusting ever so slowly, just to make the moments last longer. The rough walls rubbed his dick head, and the only thought in his mind was the ecstasy his body was experiencing. “Oh yeah” he breathed. May giggled. “Oh yeah,” she said sexily as he thrusted, “you like your big sister’s pussy, don’t you? You like fucking me. Oooh, your cock feels so good in my pussy! Oh, I love how it fills me up!” Her words were having the intended affect. Max’s thrusts were getting harder and more rapid.
After a little while they got into a rhythm. Max would thrust down, and May would thrust up to meet it. Their bodies were all that mattered. Nothing else in the world existed; only the two of them, and the sweet love that they were making. Both of them were grunting and sweating with exertion, and their limbs seem to move of their own accord. They lost track of who’s bodies belonged to whom. Were those May’s fingernails digging into Max’s back, or the other way around? Was it Max who was shouting and moaning, or was it May? Was it both of them? It was like they were in some tribal mode, with each thrust and each cry an offering to some ancient god of sexual ecstasy. And they were in ecstasy. Never before had May felt so good, nor Max. And they were doing it together. And that’s what made it all the sweeter.
Between their grunting and moaning, each of them would call out dirty sayings. “Oh yeah,” May would say, “I’ve been a bad girl. Punish me, Max, punish me!” “Oh, you like me fucking you, don’t you?” he would reply, “You love my cock in your pussy, making you feel like this.” It felt like it went on for hours, until finally Max felt his orgasm building up in his groin. “Oh my god, May! I’m cumming!” “Wait for me, Max, I’m almost there!” Their moans were so loud that, had they been aware of their surroundings, they would have sworn that people heard them all the way in Kanto.
As he neared the pinnacle, Max stared down into May’s eyes, and she returned the gaze. Together, they looked into each other’s souls; what the other wanted, what the other needed, how the other felt. There were no secrets. They were in perfect union, as one person. And then their orgasms struck.
“Oh my God, may, oh my God! Oh my God, oh my God, oh my God…” Max’s orgasm overloaded his system. It was better than any other feeling in the world. And there was no other feeling. There was just the bliss, brought on by the person he loved most in the universe. As he shot load after load of cum deep inside of her, May, too, was in Heaven. Her body was no longer her own; she was on some astral voyage of passion and delirium. Her body acted like it was possessed, her limbs twitching every which way as they tried to take the climax, and she screamed like a banshee. But she didn’t care. Everything else in the world faded away to be replaced by frenzied rapture.
As their climaxes finally subsided, they lay in utter peace, not wanting to spoil the moment. Finally, Max got up and pulled his already-drooping penis out of his sister’s pussy. He looked down, and he could see thick ropes of his cum dripping out May. He grinned. He had just had the best experience of his life. Then, the exhaustion hit him, and he dropped back onto the log. He felt like he could have slept for days.
May, too, sat up and went to sit with him on the log. “You know,” she said, “we really need to do this again sometime.” Max nodded his sleepy agreement, and the two of them hugged. And that’s how they fell asleep, hugging naked on a log in the woods, with fresh cum still dripping down out of May’s pussy.
Little did they know that a certain friend of theirs had come to find them and see how everything had turned out. And he’d shown up just in time to have one hell of a show…