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Evan Buckley had fucked everything he could think of. He'd fucked his hand, humped his pillow, splurted his cum into various pieces of clothing... He even tried to fuck his own mouth, folded his overgrown limbs into himself with his knees on his shoulders and his cock leaking pre-cum onto his lips, but never quite reaching his mouth. He'd crafted a fleshlight with some towels and a condom he got in Sex Ed, and he even once got very close to sticking his dick inside a peach.
See, that morning, Maddie had dug her teeth into a peach and sucked on the skin as the juice dripped past her lips, down her fingers and along her wrist. It had turned Evan on so much that he'd had to excuse himself to go to the bathroom, jerked off fast and frantic until he came into his hand while thinking of his sister. No, not his sister, he'd been thinking about fruit. It had been the fruit, wet and juicy and soft inside, that had turned him on so much he probably could've rubbed himself to climax through his sweatpants right there at the dinner table. Except, once Evan was alone in his bedroom, holding the offending fruit in his hand, his dick in the other... It didn't actually seem that appealing to have fruit juice squirting everywhere and getting his pubes all sticky.
Having abandoned the peach-fucking, Evan was still left with an insatiable horniness surrounding that scene. Maddie, the juice, the sucking. Her fingers, dripping with it. After a multitude of sleepless nights, Evan decided that maybe he should suck it up, and realize it was, in fact, his sister that he wanted to fuck.
Once he'd accepted this one simple fact, it was like his brain was working overtime to supply him with endless fantasies. Maddie on her bike, arching her back and rubbing her pussy all over the seat. Maddie laughing so hard at one of his jokes that it made her tits bounce underneath her T-shirt, not bothering to wear a bra at home. Maddie getting home late from a date, maybe aching from her boyfriend's cock ramming into her over and over again until he emptied his balls inside of her. Did that stuff feel good for her? Did she moan, writhe in the sheets, grab onto Doug? Did she touch herself at night like Evan did, push her fingers inside of herself and drag her slick across her pussy and her thighs?
It was driving Evan crazy, and one night, nothing was satisfying him anymore. Not even the panties he stole out of her laundry, one on his face and one wrapped around his dick, could get him to orgasm. He was too curious. He had to know how it would really feel, what she sounded like.
It was late enough that he was pretty sure everyone was asleep, so it would actually be the perfect time to do some exploring in Maddie's room. She had been busy working on her college applications, so each night she was so tired she passed out hard. Whenever she fell asleep on the couch, it was hard to wake her up. Evan was pretty confident she wouldn't notice a thing if he took a little peek at what she had going on under the sheets.
With everyone else in the house asleep, he hadn't bothered to put on sweatpants, or any clothes for that matter. He snuck into Maddie's room with his erect penis out and his bony chest bare. His sister was sleeping on her side, knees pulled up and hands tucked under her pillow. Her lips were slightly parted, and Evan could feel his dick twitching at the thought of sliding in there. Maybe he could, just a little bit.
Carefully, and as silently as he could, Evan shuffled across the floor to the side of Maddie's bed. If he just crouched down a little, bending at the knee, his dick was the perfect height to hang the head straight in front of Maddie's open mouth. It was at that same aching almost-touching distance as he could get to by himself.
Holy fuck. Evan had never looked down to his cock and seen a girl's face below it. The sight of it was so hot, he was pretty sure he could jerk off right then and there and he wouldn't even need to touch her. But... he wanted to touch her. That's what he came into her room for, truthfully.
Tentatively, Evan held his dick in one hand and touched the tip to Maddie's lips. Some of his pre-cum stuck to the corner of her mouth and immediately created a slick strand between them when he pulled away.
The next time he pushed forward, he gently nudged the head of his cock between Maddie's lips. They parted easily for him. Then, as if she was awake and wanting, her tongue moved, and pressed against him. It felt good, and wet, and he needed more of it, so it encouraged him to push in further. There was a slight scrape of her teeth as he pushed into her mouth, but it wasn't painful. It just reminded Evan that her mouth was small and tight, and he was invading it, he was going to use it, to get himself off. He could feel his blood rushing with the anticipation of it, making his dick twitch as it got even harder, growing until Maddie's lips were stretched around the girth.
Inside his sister's mouth, it was warm and slick. He could easily thrust back and forth, feeling the drag of his cock on her tongue, her sleepy swallows and murmurs, spit sticking to the skin of his dick every time he pulled out.
Evan could feel himself getting close like this, but he knew there was more. He didn't want to just cum on the first part of a girl his dick had ever touched, not knowing if there might be something better. He knew Maddie had a pussy, and that the fleshlight he'd made was meant to emulate pussies, and that had felt really wet and tight, so he was pretty sure he'd like fucking that part of her even more.
More importantly, it was becoming more and more obvious that Maddie and her boyfriend were having sex, which meant that Doug was sticking his dick inside Maddie's cunt, and Evan was justifiably annoyed at that. Maddie was his sister, and she lived in his house, and he hadn't even gotten to touch her there yet. Maybe if Evan could fill that part of her too, she wouldn't be talking about going away to college with him. Maybe she'd be happy to stay.
With some difficulty, Evan was able to tear himself away from Maddie's mouth, stroking himself with her saliva a couple times while feeling her steady breath on the wet skin. He took a deep breath. It was time to venture further. And he'd actually be allowed to cum, finally. His cock jumped at the thought.
Forcing himself to slow down his excitement so he could continue to be careful and quiet, Evan peeled away Maddie's purple sheets. She was wearing a long, oversized T-shirt. He'd seen her wear it around the house and it usually covered her ass and some of her thighs, but right now, with her legs pulled up, it almost looked like a normal-sized T-shirt, leaving just her panties on display.
They were simple panties. They weren't like the ones Evan had fished out of the laundry, which had been sexy ones. These were a simple cotton, gray or maybe a light blue. They were stretchy enough that Evan could hook his fingers into the back and pull them right down to the backs of her thighs, exposing her completely. She didn't even stir.
Maddie's pussy did not look like the diagrams he'd seen in Sex Ed, or even like the ones in the magazine one of his friends had recently brought to school, although the girls in those pictures had their legs spread. Maddie's cunt also didn't look too much like the fleshlight, although maybe if he used his imagination, and her slit was a little shorter. Instead, the slit went all the way from next to her asshole to somewhere between her thighs, and Evan wasn't sure where he was supposed to fuck his dick into.
Exploratively, he pressed his index finger against her slit. She was dry, too. Should he spit on his fingers? He dragged his finger up, and then down again. If the diagrams were correct, and she did have a vagina hole, it should be about... here. Evan pressed a little harder, his finger slipping past her folds, and then suddenly, he slipped into her down to his knuckle. And she was slick, in there. His cock jerked excitedly back to full attention as he moved his finger around. Pulling his finger away, he coated the rest of her skin around the hole with her wetness, and then he knew she was ready. He was going to put his dick in Maddie's pussy.
Holding her ass-cheek with one hand, and his dick with the other, Evan kneeled behind his sister and pressed his cock against her slit. He knew now where the opening was, he just needed to push a little - and - he slipped inside.
Maddie stirred, this time. A little wiggle of her hips, a jitter in her muscles, like her body was surprised at the intrusion. Evan didn't mind the movement, and pushed in all the way until he had no more dick left to put inside her. And then, like when he humped his pillow, he started thrusting.
It felt so good, hot and velvety and wet, and like she was gripping his cock with her insides, squeezing him and begging him to finish inside of her, to fuck all his cum inside of her, make her moan and maybe make her walk funny tomorrow. Make her boyfriend see a difference in her, make Maddie feel good and bred well- He might have moved a little too fast, gotten a little too excited, or grabbed her ass too hard, because at one point, Maddie's eyes opened and her head whipped around to him, her hands reaching back to grab at his arms.
In his panic, the first thing Evan did was surge forward and slap his hand across her mouth. If she woke their parents up, it would be really embarrassing, and Evan just needed this one time, so she just needed to chill out until he was done, and they'd go back to normal.
But Maddie wasn't understanding that, so she wrapped her fingers around Evan's wrist and pulled. She was struggling, writhing underneath him, and it was grinding her ass against him so deliciously that it felt like she was fucking him. Or fucking herself on his dick. For a moment, Evan let himself imagine Maddie on top, slamming herself down on his cock, her tits bouncing like they did when she ran down the stairs, except without a shirt, this time.
His hips stuttered, and Maddie managed to rip his hand away from her mouth, was about to yell for their parents or maybe scold them, but then he grabbed onto her hip and thigh, and he came so hard he could feel the spurts of cum hitting her insides, squirting into her and coating both of them with it.
"Jesus Christ, Evan," Maddie whispered. When he looked up at her, still catching his breath, her eyes were wide and her cheeks flushed dark.
"I- I'm sorry," Evan stuttered. Now that his dick was just uselessly inside his sister, and he would be sticky with cum when he pulled out, and she clearly didn't really want him in her bed, he suddenly felt ashamed. How could he explain that he'd needed this?
After a pause, and Evan struggling to get his dick out without hissing at the sensation, Maddie sighed and said, "It's... It's fine." She pulled up her own panties, and dragged the sheets back on top of her when Evan got up on wobbly legs. "Just go back to sleep, now."
Maddie wasn't mad. On his short walk back to his own bedroom, Evan had a hard time not getting horny again. Maddie wasn't mad that he'd fucked her pussy, she'd even said it was fine. Even though he just wanted to do it this once, maybe he could do it more often, now. Since she'd said it was fine. Maybe she could learn to love it, and she wouldn't try to get him to stop right before cumming, and she'd be happy with Evan's dick and won't need Doug anymore.
Back in bed, Evan jerked off one more time, dick wet with his own cum and Maddie's pussy slick. He thought about fucking her mouth while she was awake, looking up at him and encouraging him with suckles and wet moans. He thought about how good he did waiting to cum so he could fuck her pussy next, and he'd do that again next time. He'd spread her legs so she'd look like the girls in the magazine. Or put her on her stomach and covering her like a blanket, now that he was taller than her, and almost as tall as her boyfriend. Maybe he could even fuck her asshole. That had looked even tighter. Biting down hard on his lip, Evan came into one of his sister's little thongs, coating the part where her pussy would go, and then he finally passed out asleep, happy and sated.