Big Sister's Big Toybystago©
Tim Brady was old enough to finish high school, but he still didn't think that there was anything at all strange about spying on his older sister. It was easy to do. Their rooms were across the hall from each other, and the doors had old fashioned locks, with big fat keyholes. A curious young man could peek right through the keyhole and into his sister's room. Most days the view was boring, just the same old posters of rockstars, scattered cds, rumpled clothes and empty slurpie cups. Tim wasn't sure why he got such a kick out of watching her, but he knew that it was exciting. He got a strange thrill watching her when she thought she were alone.
The two siblings were only a year apart, Lisa was older, and working part time at a clothing store downtown. She was prim and proper, and kept her strawberry-blonde hair up in a ponytail. She always said that short skirts looked trashy, and she never wore low tops or tight clothing. Still, she'd inherited her mom's curves, and they were impossible to hide. Tim had definitely noticed her burgeoning womanhood. Family vacations and days to the beach had become more distracting than they used to be, and he found himself sneaking glimpses of her plump new breasts and rounded ass. He had to admit that maybe his motives for spying on his sister weren't entirely pure.
She'd always been uptight, and he knew that she'd be shocked if she caught him peeking. He was the problem-child, not her, and it was always him that came home with skinned knees, lost his school books or got caught stealing chocolate from the freezer. Maybe that was why he, despite being old enough to drive, saw nothing shocking about kneeling on the floor at his sister's door, and peeking through a keyhole.
Inside the room, Lisa had been getting ready for bed. Before Tim had taken up his post outside the door, she had come into her room wearing a thick, fluffy beach towel. She was still fresh and rosy from her shower. She'd had a long day at work, and made it even longer by running a few quick errands on the way home. Dinner and a long shower had relaxed her though, and left her with a warm, lazy glow.
Tim tucked his palms under his knees and squirmed for a better view. He could see the centre of the room, but whenever his sister strayed to the edges where the dressers or the shelves were he lost his view. He watched with his heart in his throat as she reached behind her to unknot the towel, and then, maddeningly, stepped outside of his view. All he caught was a flash of pink skin and the sight of a fluffy towel crumpling to the floor.
It just wasn't fair. He sighed, and then, a second later, winced, realising that she might hear. But if she did, she didn't show it. Inside the room there was a shuffling sound of clothes as Lisa dug through her dresser. When she re-emerged in front of the peep hole she was wearing a filmy nightgown. She'd grown up some since first getting the gown, and at the bottom it barely fell past her hips, while on top, her breasts bulged against the fabric.
Tim watched anxiously as his sister went through her routine and tied up the room a bit. Then, against all hope, she bent to pick up the forgotten towel, and he got his first precious glimpse of her perfect round ass, and the soft cleave of her teen-aged cunt beneath it. His first glimpse of a real girl's pussy only lasted a second, but he'd remember it forever. She kept it trimmed and shaved, so that it was smooth and bald, and he had just the slightest glimpse of curly red hairs between the soft swell of her thighs. Then it was gone, and Lisa hitched her nightgown back down, threw the towel in the dirty laundry and finished getting ready for bed.
The next few minutes were hell for her brother, who was desperately waiting for another slip, and another stolen glimpse. It didn't matter that it was his sister, and it didn't matter how guilty he felt. He wanted to see those forbidden fruits again, the ones that had previously only existed on computer screens and stolen magazines.
While her brother thought guilty thoughts, Lisa finished her routine. She turned off her computer,and set the alarm on her phone to get herself up for work in the morning. She paced around the room, tidying up, and settling down. For a while, it seemed that her poor brother would be disappointed. That's not how it was though. Luckily for her watcher, Lisa couldn't relax. She'd broken up with her boyfriend the week before, and without him around, she was constantly, intensely horny. It was unbelievable. She'd never have guessed that she'd miss sex so much; they didn't do it that often, and when they did it had always been sort of quick and disappointing. But now that she was single it was all Lisa could think about. it wasn't something she could talk about, her friends knew she had a boyfriend, but she'd never opened up about sex, and her family... well there were some things you just couldn't talk to them about. Still, Lisa was horny, and it had been all that she'd thought about at work all day.
That was why she'd stopped at the sex store on the way home. It was horribly embarrassing. The store was the kind of place that she was sure only sleazy old men went to, and she'd spent the entire time nervous and trembling as she picked through novelty props, dirty movies and sex toys, tons of different sex toys. She hadn't been able to stop blushing as she'd paid for her selection, but the girl at the counter chewed her gum and hardly looked up. Now Lisa was ready to try out her toy.
It was a dildo. But it wasn't just any dildo, it was a huge dildo. Lisa nervously tore the cardboard and plastic box apart, and drew out her new friend. Suddenly she felt overwhelmed. It hadn't looked so big in the store! Not by half! Sitting in her room, it seemed bigger than anything she'd ever seen. The heavy plastic dong was easily twice the size of her ex-boyfriend's cock, and was ridged and floppy, with a fat suction cup on the base and two fat plastic lumps like balls. It felt heavy in her hands, and despite her arousal, Lisa hesitated, chewing on her lip. Too much?
Outside the room, Tim shifted on his knees. His posture was totally uncomfortable, but that didn't matter, his sister was finally doing something worth spying on. He couldn't tell what it was Lisa had unwrapped, but the way she was eyeing whatever it was, it had to be something good. Lisa ran her fingers up the fake cock, measuring it with a caress. So long, so fat. She thumbed the little slit at the top, and wrapped her fist around the shaft, pumping it curiously, like it was a real boy's cock. Her fist fit around it, but her fingertips barely touched on the other side. Could she ever take something like that? Surely not. Even the thought sent her heart pounding and her breath quickened to catch up. She had to find out, but if she was going to take it, first she'd have to get it wet.
Tim squirmed. There was no way that his stuffy sister was holding what it looked like she was holding. His prim, perfect sister, kneeling on her bedroom floor, pumping a giant dildo? It was impossible. But there was no denying what his prying eyes saw. No way! It had to be a mistake. But then Lisa shattered any last lingering doubts, by lifting the dildo up to her mouth, and kissing the head of the huge prick. Very slowly she took the dildo into her mouth, slurping at the rounded head. The tip was the size of a fat plumb, but it wasn't too big. Her jaws yawned wide, and she took it into her mouth, feeding in the first inches until the blunt head nudge at the back of her throat.
It wasn't enough. Lisa had to get the whole thing wet, and now, with the tip wedged between her pretty lips, it was like the fake cock was daring her. Could she swallow it? She knew girls did, but could she?
Watching from outside the room, Tim squirmed. He knew it was wrong to watch, but his own cock wasn't listening. It was hard and stiff, aching at the fly of his jeans. He draped a hand over it, adjusting it to a more comfortable position. He should look away. But he couldn't tear his eyes from the sight inside the room.
Lisa closed her eyes, and tilted her head back, turning her face up to the ceiling. She took a deep breath. Inch by inch she slid the cock deeper into her mouth. It was impossibly thick, but it slid easily past her pink lips and nudged under her tonsils. Her gag reflex started to kick in as it filled her throat, and Lisa knew it was now or never. With a final thrust, she punched that thick shaft down into her throat.
Tim watched in shock as his sister's neck bulged obscenely with the nine inches of dildo crammed inside. The world had closed into just that scene. All he could see was his sister, so sure that nobody was looking that she'd utterly debase herself with a plastic toy.
Lisa knew she'd taken the entire dick when the fake rubber-balls rested came to rest against her chin. Her eyes bulged, and the shaft pressed against the back of her throat so that she thought she'd puke, but the tingle between her thighs told her she loved it. She couldn't hold it though. Panicking for a second, Lisa tried to suck air, and couldn't. Frantic, she drew the dildo out like a sword swallower finishing an act, and sucked in air to replace it. She'd done it! Not the kind of thing you could show off, but she'd done it! Panting, she caught a sight of herself in her dresser mirror, and didn't recognise the girl she saw. Lisa was utterly dishevelled: long strings of saliva kept her connected to the fake cock, and her nipples begging to escape her flimsy nightgown. It was totally obscene.
It wasn't over though. As far as Lisa was concerned, she'd barely begun. Now more than ever she needed to feel that cock inside her. The suction cup would make it easy. That's what it was there for right? Except that her floor was carpet, and the dildo wouldn't stick. Still breathing hard, she searched the room. An old Biology text would be perfect. With a big lick she wet the dildo's suction cup and smacked it down onto the glossy cover of the high-school textbook. Seconds later she was kneeling over the spit-soaked rubber cock with bent knees. Her legs trembled as she sank down onto the massive sex toy, spearing it into her teen-aged cunt. Lisa's pussy-lips spread to accommodate its girth, stretching and pulling at the wet plastic. Inch after inch of the cock sunk into her, and as the pleasure shot through her. If she hadn't just swallowed that same toy, Lisa never would have known she could take it. It split her like nothing she'd ever felt before, driving deep into the centre of her aching need.
As she sank to the base of the toy, Lisa's lips stretched and her knees trembled, her dimpled ass flexing for her secret watcher. Soon her vanishing act was complete. Her sweat-soaked butt cheeks were pressed against the Biology text, and the dildo's full nine inches were hidden inside her greedy pussy. After she caught her breath, Lisa lifted herself up, and dropped her weight again, letting the dildo's slippery shaft appear and disappear in a quickening rhythm. Soon she was deliriously fucking the toy, totally caught up in the wanton act.
Outside, Tim watched his sister's cunt spread wide with each thrust, swallowing the toy. Above that stuffed cunt hole, Lisa's asshole winked back at him, tight and brown. He'd never thought about it as a sexy part of a girl before, but on her it was perfect. He was totally enraptured with the way that his sister's tiny sphincter squeezed tight and bulged as each thrust of the toy pushed her insides outward.
Somewhere along the line, Tim's hand had found its way back into his lap, and he'd begun stroking herself through his jeans. His cock was thick and swollen, at least as big as the one his sister was impaled on, he was sure. His mind was racing, imaging what it would be like if he was someone else -- someone brave enough to barge in through that door and offer her his very real, very erect cock. He imagined her lips around it as she fucked the toy, his throbbing length buried deep in her gagging throat. His forehead was pressed to the door jam, and he stared in stunned silence, caught in the obscene act before him and the electric pleasure he felt each time his hand grazed the bulge in his jeans.
Lisa's breasts shook and heaved under her thin nightgown, and her mouth hung open as she flung herself at the cock again and again. It didn't take long at all for her to cum, shaking and jerking at the cock. She bit her lip, smothering a cry of pleasure that shot up into her brain as she sank to the base of the cock again. Suddenly, it was too much, and she was losing her balance and cumming all at once. A squeal escaped Lisa's tightly sealed lips, a high keening, "Yeeep!" that made Tim cringe in the hallway. Lisa fell forward onto her knees, shaking and moaning and biting down on her knuckles as the orgasm washed over her.
The last thing Tim saw stuck in his head, the image of his sister, on hands and knees, the cock jutting from her spasming cunt, as juice rolled down her thighs and her asshole clenched and winked with each jolt of passion. His own horniness was overwhelming, a tight, driving need in his gut. He only had a few seconds, but he managed to unsnap the top button of his jeans and thrust his hand in. He'd made himself cum before, alone in his room, but never like this. All it took was a grasp and a few frantic jerks and he was there, wet seed spilling out over his hand and into his shorts. The whole time his eyes never left the keyhole, or the sight of his sister lying there, panting, a dildo protruding from her cunt like king Arthur's sword, begging for him to pull it free and replace with his own aching meat.
Afterward, Tim stumbled back to his room, grateful to have escaped detection and still shaking with the aftermath of his own orgasm. He was sticky, tired and vaguely ashamed, but he knew he'd be back. After what he'd seen, he'd be kidding if he thought he could stay away.