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"Thank so much for arriving on such short notice, I don't know what we would've done if you weren't here," Jimmy's relieved mother said, one foot in the door. His father was waiting in their car outside, and he was growing more impatient by the second.
"Oh, don't worry about it. Jimmy's a really good kid. We'll have a lot of fun like we always do, right Jimmy?" Anya smiled while looking down at him, and Jimmy smiled back insincerely. She was a nice enough woman, but she was so annoying! Always telling him what to do, what to eat, when to go to bed, she wasn't his mom! She was simply a stupid babysitter who'd never leave Jimmy alone; nevertheless, he had to act innocently tonight in order to enact his plan.
"Definitely! Lots and lots of fun," he said, holding onto Anya's arm. Jimmy grinned ear to ear while looking up at Anya, and his mother laughed.
"Oh my! It looks like he likes you!"
"Really? I'm so glad." Anya patted Jimmy's messy head of hair with her other hand.
"Yes, and I don't mean to sound like a broken record, but we're really so grateful for you. You're the only babysitter we've found who has accepted such low prices. We feel so guilty, we'd give you more if we co—"
Jimmy's mom was interrupted by the sound of his father honking the car extremely loudly. "Get a move on, woman! We don't have all day here. I payed good money for these reservations!"
Jimmy's mother sighed and closed her eyes tightly shut, forcing a thin lipped smile. "Well, mommy and daddy have to go now, but be good for Anya, alright Jimmy? We'll be back in the morning." She knelt down and gave him a quick peck on the cheek before leaving, Anya waving after her and Jimmy sticking his tongue out in childish disgust.
"Eww…" he said, wiping his cheek clean of any drugstore lipstick while watching his parent's beat up car drive away. Anya and Jimmy were completely alone now. The sound of crickets and their own breathing were the only things that they could hear.
"Well, what do you wanna do now?" Anya closed the door in front of her, locking it and looking back at him as they both stepped back.
"Uh…" What was something Anya liked to do? Jimmy pondered for about a second or two before he got it. "How about a board game?"
Anya looked amusedly surprised, raising her eyebrows. "You usually tell me you want to play outside, what's with the sudden nerdy interest?"
Think, Jimmy, think. "I thought we could do something fun for you as well, since I know how much you like them." Jimmy wasn't the sharpest tool in the shed, but he wasn't completely idiotic. It was obvious that he had to know a few personal things about Anya if he wanted tonight to go smoothly.
"Isn't that sweet?" She knelt down on the floor and pinched his cheeks, and Jimmy had to stop himself from slapping her hand away. "But I can't, I have to study for my psychology exam that's coming up." She frowned like she was genuinely apologetic, which Jimmy found difficult to believe. "I'm really sorry, Jimmy. Maybe next time."
Now it was time to pull out the big guns. Jimmy sulked and looked away, furrowing his brows. "It's ok, I guess. I just never have the chance to play with anyone because my parents are always away, working. And my friends… they don't want to be with me, lately."
Anya turned her head to the ground, her mascara heavy eyelashes weighing her doe eyes down. Jimmy didn't like to admit it, but Anya was extremely pretty. Prettier than any of the other girls in his school, that was for sure. "Oh, Jimmy… how could I say no to you? We can play a board game… but only one round. Ok?"
"Yes! Thank you so much, Anya!" He tightly hugged her, and she was noticeably taken aback by the sudden physical affection. He was pressed right in between her large breasts, like the ones his mom used to breast feed him with. How he wished he could continue getting breast fed by her. 'You're getting too old for it,' she said. That simply wasn't fair. Anya hugged him back, pulling his tiny body closer to her bust.
"Now, which one do you want to play?" She pulled away from the hug and got up, much to Jimmy's dismay. He would never say it out loud, but he would've liked to keep hugging her for at least another moment.
"Candyland?"
"Sure." She took a few steps to the coffee table and bent down to get the board game underneath it. As she bent down, Jimmy noticed her fat ass. God, she really was a cow. But for some reason it made him want to put his private parts inside of her, which should have made him want to puke. That was totally gross, right? Well, if he truly thought that it was, there'd be no point in his plan.
Jimmy wasn't as naive to not even know about the birds and the bees. Sometimes, he'd catch his mom and dad fucking in their bedroom. They normally wouldn't be aware Jimmy's presence, but there was this one time where his mom locked eyes with him while she was getting rammed from behind. Neither of them ever spoke about it.
Leading to the deed, Jimmy's dad would keep begging and begging, and his mom would start off by saying no, but his dad would always win in the end. Whether his mother lay there like a dead fish as his father pumped his dick in and out of her, or she was fast asleep and he quietly humped into her privates, it didn't matter. He always got what he wanted in the end. Jimmy was going to get what he wanted in the end as well, and nobody could do anything to stop it.
He snapped back to reality as Anya sat on the couch next to him. It seemed like he automatically sat down while thinking about his parents having sex. "Don't think I'm gonna go easy on you just because you're a little boy, alright?" She mischievously grinned, setting up the game.
"Hey Anya, which do you like better? Coke or Pepsi?" Jimmy promptly got up from the couch, heading into the kitchen.
"Umm… Pepsi? Why are you asking?" Anya called out from the living room, still setting up the game.
"I wanted to make a drink for my favorite babysitter, of course!" Jimmy shouted, pouring the Pepsi into a cup.
"Aww. You're too sweet."
What she didn't know, is that Jimmy had mixed crushed pink tablets of Benadryl in her drink. He swirled it around in her cup with a spoon hurriedly. A memory came back to Jimmy of him not being able to sleep, and his mother reluctantly giving him some. "Don't get hooked on these, alright?" she had said to him before kissing him goodnight.
At the time, Jimmy was confused. All that the antihistamine did was make his sleepy, how could he get addicted to that? Nonetheless, he was curious, and one day while his parents were particularly busy, he took a bunch of them with a huge gulp of water. He expected wild hallucinations, not falling asleep yet again within only a few minutes. Lame… well, what did he expect? At the very least, he figured out a way to assault his babysitter.
Jimmy walked back into the living room with the cup in hand, smiling as he handed the spiked drink to Anya. "Thanks." She took the drink, placing it on the coffee table. Jimmy frowned, gritting his teeth.
"You're not going to drink it?"
"Oh, no, I will. Just give me a moment. Jeez, Jimmy… girls don't like it when you're pushy, y'know?" Shit, he had come on too strong.
"Sorry, Anya… hey, what color are you?
She chuckled at the quick change of subject. "I'm blue, and you want to be green, right? That is your favorite color, isn't it?"
Jimmy blushed, even though it was such a stupid piece of information about him. His favorite color, he couldn't help but scoff internally. He wasn't a little kid! Although, he couldn't lie, he was kind of fond of green. "Yeah, how'd you know?" Ugh… how could she get him so flustered like this? It was repulsive.
"I listen to you while you talk. I like you, Jimmy," she said, her smile warm.
Jimmy's face instantly turned into a deep red, and he stopped himself from breaking into a dumb smile at her comment, looking at the ceiling. "That's gay." It was hard for Jimmy to tell whether she meant it romantically or platonically, but he knew that deep down she wasn't a pedophile. He didn't know if he wanted her to be one. If she was a man, he'd hate it. But it's not like a woman could take advantage of a child in that way, right?
She chuckled at and raised an eyebrow at the unexpected response, but not she didn't want to go out into a full lecture on why it wasn't okay to say those types of things. She looked too tired for that, as much Jimmy knew she'd love to educate him and make him feel even stupider. "…Whatever you say," she said, rolling her eyes and smirking.
Anya let Jimmy roll the dice first, and she bared with Jimmy's annoying mini temper tantrums whenever he was set back a few spots on the game. She didn't know what he had to be so upset about, Candyland was purely a luck based game. During the middle of the game she sighed and grabbed the glass off the coffee table, bringing it to her lips and drinking the sugary soda.
Jimmy watched in anticipation as she drank the beverage. If this didn't go right, his whole night would be ruined. Not to mention how rarely the stars ever aligned this much for him, he likely would have never gotten this chance again.
She swallowed the liquid, wiping her mouth clean of any remaining soda. Jimmy frowned, his plan really didn't work. If it did, she would've fainted immediately! That's what all the movies showed him, so it must've been true. What a shame. He might as well continue playing this stupid board game with her for a few more minutes, and he'd win eventually, obviously. When she'd inevitably force him to go to bed, he'd jerk off to the thought of spraying his spunk all over her cute face. He could shoot pretty decent loads for his age.
Just when Jimmy was starting to lose hope, Anya yawned. It was a few minutes after she had drank the Benadryl laced Pepsi, and she placed a hand over her gaping piehole while closing her eyes tight. An image of Jimmy forcing his penis into Anya's mouth soon erupted, and Jimmy grinned at the thought of it. Be patient, he told himself.
"Jimmy, you don't mind we cut this game short, right?" Anya rested her head upon the back of the couch, blinking her tired eyes.
"Yeah, that's fine," he said, holding back his excitement.
"Thanks, you're so considerate…" Her eyes got to the brink of closing, but shot quickly open as if she remembered something. "I have to study for my exam!"
Jimmy got off the couch and moved over to Anya, covering the bunched up blanket in the corner of the couch over her body. "You'll pass anyways. You're one of the smartest women I know." Saying any lie to get what Jimmy wanted wasn't uncommon for him, even if that lie made him want to burst out laughing.
"You're such a sweetheart," she said absentmindedly. "I guess it'll be ok, I can always study in the morning…" Anya changed positions, laying her head on top of the throw pillow that was against the arm of the sofa. "And you'll be okay with not getting tucked into bed tonight? You won't have any nightmares?" The mention of his semi frequent nightmares somewhat embarrassed Jimmy, but he brushed the feeling off as he thought about his mission.
"I'll be alright, Anya. Go to sleep, okay?"
"Mhmm…" she said, drifting off into slumber.
Jimmy must've been dreaming, this was too good to be true. He decided to wait a few minutes before having his way with the older woman, but he couldn't wait too long. What if she wakes up too soon? He'd get himself erect in the meantime. Pulling down his shorts and tossing them aside, his penis was barely visible out of his tighty whities. Calling it a dick would be too generous, the thing was so cute and tiny that when hard, it hardly surpassed Jimmy's thumb. Jimmy was still a little boy, so that was to be expected, but he had still felt insecure about his lack of size.
He remembers having compared his dicklet to Curly's in a cramped bathroom stall that one day, but he really didn't want to think about that when he was right about to fuck his fat tiddied babysitter.
With a finger and thumb, he gently stroked his little thing, and he got hard almost instantly. Removing the blanket off Anya's body, he climbed over her and straddled her. He hoped that she was a heavy sleeper; otherwise, he was screwed.
Anya's udders were so lewd, what was she thinking? Flaunting them around such a young kid, she was practically asking for it. What did she expect, after all? Boys will be boys.
He lifted her colorful sweater above her breasts. The action revealed two beautiful, large sacks of fat that were begging to be sucked on. They were dressed in a plain black bra, like one that Jimmy's mother would've owned in her dresser, through which Jimmy would discover by snooping. He couldn't help it! If she didn't want him going through her stuff, she should've locked it in the first place. He slipped the bra down so that Anya's nipples could be displayed. Those large, brown areolas so like Jimmy's own mom's. It was strange he was thinking so much about his mom at that moment, but he brushed off the responsibility of having to unpack his feelings.
Instead, he wanted to see if Anya would provide him any milk. Quickly, he started sucking on one of Anya's nipples with his annoying, bratty mouth. He fondled and groped Anya's other breast with his opposite hand, twisting and squeezing her nipple. She tasted of sweat and sugar cookie lotion, but alas, no milk. He tried biting very gently to see if that was the issue with the lack of dairy, but doing that only produced muffled moans and whimpers from Anya.
It was Jimmy's lucky day, she was a heavy sleeper. To her, it must've only been a bad dream, one where she was getting assaulted by a monster, not a little boy, although it was unclear which one Jimmy was supposed to be. But he couldn't deny that if he kept this recklessness up, she was bound to break from her slumber. He still wanted to have his fun, though.
Jimmy swirled his tongue around her nipple while still pinching her other one with his grubby fingers, dirt underneath his nails. He was humping against Anya's fat thigh, his hips pathetically and desperately thrusting like a dumb dog. It was impossible to hold back anymore. Jimmy's willy was throbbing, if such a minuscule thing could even do that.
He pulled Anya's long skirt to her upper thighs as he struggled to lift her legs, momentarily separating himself from her tits to do so. Pulling aside her frumpy panties, he saw her hairy cunt. It was a jungle down there. Jimmy would have found it revolting if he wasn't so horny. Plus, it looked weird! Jimmy saw pictures of vulvas before, and he never liked the look of them. He didn't have to look at her pussy any longer, though, not when he was too busy fucking her to do so. Anya wasn’t the slightest bit wet, but that was no problem, considering that Jimmy’s miserable excuse for a dick had no chance of injuring her.
Excitedly, he finally entered her, a warm squishing sound being made when he did so. She immediately enveloped him within her warm, tight walls. “F-fuuuuck…!” Jimmy whined. He almost didn't want to move at all, it felt like he didn't even need to if he wanted to cum. But he wanted to make the most out of his experience, so he started to nudge a little bit into the older woman. Even if she was awake, she wouldn't have felt anything because of how tiny he was.
He started using Anya's breasts as handles, grabbing onto them while he began ruthlessly fucking her. Well, as ruthlessly as he could, if one took into account his inexperience and small size. If the boy wasn't so weak, Anya's boobs would have surely gotten bruised. His hips slammed into her, making wet squelching noises as he panted. Her tits would've been bouncing up and down if he hadn't been holding onto them so kindly.
Jimmy kept fucking her, grunting and whining like a little boy should. Her face looked so unpleasant as she slept in her makeup, her frowning evident. That made Jimmy even hornier, knowing that Anya wasn't feeling good at all. So soon, he was gonna cum into his hot babysitter. He slowed his thrusting down as he felt his orgasm come closer. Finally, he unloaded his hot load of sperm into her. Jimmy didn't know if it would get her pregnant, given his young age, but in the end, he wasn't exactly thinking with his brain.
Sighing, he removed his penis from her. He creampied her like how he always wanted to! She was stuffed by him, stuffed with his dicklet and his cum. The greedy boy still wasn't finished, though. He moved upwards on her body, and placed his cocklet in between her milky tits, his hands forcing her breasts to wrap around his genitalia. The friction caused by his movement wasn't an issue because he was already covered in Anya's juices.
Just like her vagina, her breasts were so warm and inviting. "Hah…. hah." Jimmy's body was coated in sweat, and the living room smelled like Anya's and Jimmy's scent forcefully mixed together. Biting his lip almost enough to draw blood, he was nearing climax yet again. For the second time that night, he came. Pearly white strands of liquid decorated Anya's breasts. Jimmy would clean it up eventually, although he'd hate to ruin his stunning work of art.
This night had been long, but he still had one more thing left to do. Thinking back to his thought about cumming all over Anya's face, he grinned. All good things come to those who wait, he thought. And he was right. Removing his penis from Anya's boobs, he hovered over her face, jacking off profusely. Young boys had so much stamina and energy, it was truly amazing. Anya should be grateful that she got raped by such a little kid. Younger is better, after all.
After only a few seconds, he came all over her face. Some of it landed on her lips, some on her cheeks, some in her eyes, but the point was that he completely desecrated her beautiful face. Grinning, Jimmy pulled Anya's lower lip down, and rubbed his semen into her gums with his thumb. He chuckled at the thought of her being confused about the salty taste in her mouth when she woke up.
The spiked soda was still on top of the coffee table, and Jimmy peered over it. Staring at the bubbling liquid, he noticed that he forgot to put a coaster underneath the cup. When his mom came home, she'd totally be pissed.
Anya woke up in the middle of the night. The blanket was still covering her body, but in a different way than before. She couldn't put her finger on it. Warmth and sweat overwhelmed her, so she quickly tossed the blanket aside. Her limbs were heavy and hard to keep up, although that wasn't too strange. She was simply dehydrated.
Yawning, she got up from the couch and headed into the kitchen for a glass of water. She was parched because the last thing she had to drink was that Pepsi, and it tasted awfully odd for some reason. She disregarded that, Jimmy probably just made it weird.
She filled her glass up with water and walked back to the living room, sitting on the couch. Except… her hand felt a wet and sticky substance on one of the cushions. She lifted her hand up only to see… nothing.
Definitely. It was nothing at all, she told herself. If it had been something, that would've been awful, and it would've changed everything. If it had been something, she would have to tell someone about it. But what would there be to tell? She'd be the predator in the situation because how could a child do something… like that? How could she let that happen? She was the adult in the situation, and adults aren't supposed to be victims, especially not to snot nosed little boys. That's why it wasn't real.
Anya grabbed a paper towel and wiped the stain off the couch, though it was difficult to see because of the darkness in the room. When the sofa was clean, she collapsed on it and brought the cup of water to her lips. Before she could drink it, she noticed the weird taste in her mouth. Feeling around her lips, gums, and teeth with her tongue, she tasted salt.
It was probably because she didn't brush her teeth before falling asleep. She took a chug of water, but couldn't fall back asleep that night, no matter how hard she tried. Even if it wasn't real, she'd get a Plan B pill the next morning. Just to be safe. Our worst moments don't make us monsters, she told herself.