“Obviously, we need someone to watch you and the house for a week.”
“Aw, mom,” Chris whined, “I’m too old for a babysitter.”
“Honey,” his mom rebutted, “I know you’re growing up, and if this were just for a night or two I’d be fine, but this will be a whole week: 7 days! I just want to make sure you’re in good hands.”
Chris was crushed and started to get down in the dumps, but his mom then said something completely unexpected.
“I tell you what, if it makes you feel any better, why don’t YOU choose the sitter."
This was DEFINITELY going to be the best start to summer EVER. Why, you might be wondering? Two words: Sue Ann.
Sue Ann was the absolute hottest girl in the whole world to Chris. She was about 5’4, but had long, slender legs despite her height; had short light brown hair with dark brown highlights, and had just turned 30 before the start of summer. The truly amazing thing about Sue Ann is that she didn’t date much, primarily because she was so busy running several side businesses, one of which was house-sitting. Last summer just before he turned 13, Sue Ann became the object of Chris’s “sexual awakening”.
Sue Ann came over to watch Chris while his parents were on a weekend getaway. Chris was sitting at the kitchen table waiting for her to get ready for a dip in the family pool, when Sue Ann came into the room wearing only a bikini – he literally didn’t know what to say. All he could do was stare at her slim body, perfectly sized boobs, beautiful legs, and bare feet. Not to mention, as she was going through the cabinets looking for a quick bite, she unknowingly gave Chris a great view of her huge ass. He had never seen anyone so beautiful in his entire life. Sure, he had girls at school that he kind of liked, but never standing before him, practically half-naked.
He began daydreaming about her. Sure, she was almost twice his age, but she honestly looked like she was in her early 20s. He imagined running his hands through her hair and down her slender back, untying her bikini top as he did.
“Chris, are you OK?” Sue asked.
Chris didn't realize how out of it he was until Sue had started poking his arm.
“Um….yeah.” He managed to sputter, snapping back to reality.
Sue Ann could see right through Chris; he was drooling over her….and she teased him non-stop because of it: Shamefully posing in front of him; rubbing her arms and legs sensually; plus, she actually asked Chris to rub suntan lotion all over her. Chris could hardly stand it watching her sunbathe by the pool, waving and winking at him; he was hooked.
To top it all off, before Sue Ann left when Chris’s parents returned that weekend, he shared the most amazing moment with her. They had asked Chris to help Sue Ann out to her car with her overnight bag; after Chris placed her bag in the trunk, Sue Ann dropped a bomb.
“Chris, look,” she began, “I know what you think about me.”
“I….uh, don’t know what you mean, Sue,” He stammered.
“Sure,” she said sarcastically. “I had fun this weekend, Chris.”
Sue came closer, her radiant smile beaming from cheek to cheek; Chris remained speechless as she approached and whispered in his ear.
“You know, if you were a bit older, I just might let you take me out.”
Then, she gave Chris a peck on the cheek.
And now, the only reason Chris woke up before noon today was because, besides his parents leaving late that morning, the world’s hottest house-sitter was coming over.
Chris wasn’t new to having sitters stay with him, even at his age. He was used to it; both his parents do a lot of traveling for their jobs, and Chris had several house/baby-sitters over the last few years: MaryAnn, the cutie with long black hair and a New York accent; Noreen, the work out guru; Guerly, the tall, black Haitian who could easily be a model; one other who shall not be named; and, of course, Sue Ann.
"Chris, the sitter’s here!" he heard his mom call out.
Chris’s heart began racing, he rushed to finish getting dressed, and quickly glanced at the clock while he put his T-shirt on: 10:32 AM. He practically jumped down the stairs, made a B line into the living room – perhaps a little too eagerly – and slammed right into a plush wall.
Chris stumbled back, and realized just who he ran into….Shannon.
That sitter who shall not be named….Shannon. She had been Chris’s babysitter for most of his life; despite his efforts to get someone else as he got older, especially when he met some of the other, better choices.
Shannon was 35 and just about the same height as Chris (about 5'3", which offered him some relief) with dark brown hair, which she usually tied in a bun. She was also slightly tan; it wasn't overly obvious until you compared the tanned and untanned parts of her body.
Despite the fact that Shannon was the same size as Chris now, she still had an edge: She was huge, not really fat mind you, but beefy, and loved to wrestle, normally easily overpowering Chris when she did.
It’s not that Shannon wasn’t cute, Chris hated to admit, but she had features that one couldn't miss: first off, she had huge breasts, DD by Chris's estimate, that were almost laughably too large for her frame, but dialed back just enough so as not to be labeled "enhanced". Secondly, she had the biggest (not fat) ass Chris had ever seen, all the better to wiggle in his face and sit on him.
The final noticeable feature about Shannon was that she oddly had big feet. Not that Chris was really into that sort of thing, he just couldn't help but stare, probably because Shannon tended to go barefoot a lot of the time, her feet making loud stomping noises as she walked, and prepared to crush anything in their path. There was one time when Chris saw an ant walking across the kitchen floor when Shannon boomed in barefoot. His eyes grew wide in amazement when she stepped right on top of it, squishing it under her bare sole, and she didn't even realize it. Chris actually felt a little sorry for it, poor little thing; what a terrible way to go.
Chris didn’t want to stare at her features now that he was older (and “awakened”), but Shannon made it very difficult. Not long after his special moment with Sue, Shannon house-sit for a couple of days. At the time, she was wearing short shorts, a tank top that accented (to be perfectly honest, more like made one pay very much attention to) her DD sized cleavage, and was going barefoot around the house. As soon as she caught Chris checking her out (which, he wasn’t, it was just a quick look, and he hated his hormones for it), she really turned up the teasing: she took Chris’s writing pen and stuck it in her cleavage, telling him to fetch or else, and normally “or else” meant sitting on his head and farting. Then there was the time Chris was asleep on the couch when he woke up with a gigantic ass right over his face, Shannon saying "kiss my butt,” and then her letting out a huge fart. She even made Chris give her foot rubs and would stick her feet in his face if he refused. Shannon knew Chris secretly liked her figure and couldn’t help but stare at her; she was NEVER going to let him live it down.
Shannon was standing right if front of Chris in the living room, wearing a tight tank top that showed off her boobs like you would not believe, cut-off jean shorts covering up a pair of pink lace underwear – Chris could see the straps sticking out under her tank top when she lifted her arms slightly – and flip flops. She flashed Chris an all too familiar smile, and he responded with his usual deer-in-front-of-head-lights smile. Chris turned away from Shannon and saw his parents getting ready to take some bags out the front door.
"Mom?" Chris asked nervously, “what’s going on?”
"I’m, sorry sweetie,” she began, “but Sue had to cancel: something came up and she’s really busy this week. She wanted me to tell you she was really sorry. Shannon was the only sitter I could get on such short notice.”
“But mom,” Chris whined quietly so Shannon couldn’t hear, “I really don’t like her.”
“Honey,” his mom said sternly, “I know you’re disappointed, but you’ve known Shannon for years; you’ll be fine, so be nice, and behave. Shannon, make sure Chris gets out of the house for some exercise, I know it’s summer, but I don’t want him stuck in front of the TV all week.”
“Don’t worry, Mrs. Martin,” Shannon reassured her giving Chris a big hug from behind, “I’ve got plans for him. Were gonna have fun this week, trust me.” Shannon winked, giggling a bit. Chris only flashed a nervous smile; he wasn’t sure exactly what she had planned, but he just knew he wouldn’t like it.
“Bye hon, love you, see you in a week.” Mrs. Martin said as the door closed.
Chris still had Shannon hanging on his shoulders, grinning with anticipation. Chris knew exactly what was coming and tried to run, but he was too slow. Shannon grabbed him around the waist and wrestled him to the floor. Actually, she just fell backwards, pulling Chris to the ground by his shoulders.
“Shannon, wait! STOP!” Chris protested, but Shannon didn’t let up. She flipped over until she was on top of Chris with his back to the floor, then she flashed him a quick grin and licked her lips before smothering him with her huge breasts. The last thing Chris saw was two giant tits, muffling his shouts. He struggled to breathe, trying to push the Shannon’s huge figure off of him and get away, but that’s just what she wanted him to do….and boy did he try, because not fighting back usually meant a face full of ass. Chris’s shouts for mercy went unheard from being smothered beneath Shannon’s tits; it wasn’t long before Chris’s face was turning red, both from exhaustion and lack of oxygen. He started tapping her arms, desperately hoping she’d let him up.
Finally, Shannon removed her breasts from Chris’s head, gave him an unwanted kiss on the cheek, and sat on his chest, pinning his arms beneath her thighs.
"Mwa ha ha ha haa! I win!" Shannon cackled, smiling down with a big grin. "Now then, what shall we do next?"
"How about getting off me!" Chris demanded.
"Oh, come on," Shannon egged on, "you know you like it."
"Not really," he responded.
"Well that's not what your pants say," she continued.
"I can't help the way my body reacts.” Chris said self-consciously, embarrassed by his slight boner. “Please get up."
"Alright, but I'm not through with you," Shannon relented, pulling herself up of the floor. Chris was already sick to his stomach from the situation. Meanwhile, Shannon was contemplating what to do next and, after a long pause, she started grinning again.
"I have an idea..." she began.
"I don't care," Chris cut her off, “I don’t want to hear it!”
Shannon crossed her arms and grimaced, "Oh come on! You don't even know what I was going to say."
"I don't care what kind of idea you have, I'm not doing it."
"See, now that's not fair. You're treating me like some sort of enemy."
"You are the enemy!" Chris said bluntly.
"Aw!" Shannon scoffed with a dubious look of false hurt, "I can't believe you think of me that way. I mean, I'm your sitter. It's my job to look out for you and keep you safe. I'd never do anything to hurt you. Remember that time you ate your dad's fungal cream?"
"You promised you'd never mention that again!" Chris snapped in embarrassment. "And furthermore, you're the house sitter, NOT my babysitter!"
"Yeah," Shannon reluctantly agreed, "but haven't I always helped you out when you needed it?"
Unfortunately for Chris, it was true: she had helped him in the past, but she had also caused him a lot of trouble, too.
"Shannon," Chris stated, giving her the cold shoulder, "I just want to enjoy my summer; I'm just going to go upstairs and play X-box, OK?"
"Alright, I see how it is," Shannon relented, "but before you go, have you ever had a beer?"
"Of course not, I'm 13." He responded bluntly.
"Well, come on," she beckoned, "we'll split one. Your parents wont mind."
"But..." Chris began to object, but Shannon was already halfway to the kitchen. He wasn't quite sure exactly how it happened but he was about to split a beer with the house sitter. Chris sat on the barstool at the counter over looking the sink while Shannon moved about the kitchen. Chris's view was momentarily blocked by the refrigerator as Shannon spent some time getting the drink. She finally emerged carrying two glasses and the bottle of beer -- A small glass and the bottle in one hand and a stein for her in the other, Shannon being quite the avid drinker.
Then, she shut the door with her foot, and placed two glasses on the counter.
"Are you sure this is okay?" Chris asked as she poured.
"Just lighten up," She pegged, "Let loose. You said it yourself, 'it's your vacation'."
After finishing pouring, Shannon arched her brow thoughtfully for a moment and then ejaculated:
"Hey, Chris. Let's make a bet. I bet I can finish my drink before you."
Chris was fairly sure accepting this bet would be a mistake, yet still inquired, "What do I get if I win?"
"If you win," she replied, "I won't fart on you for the rest of the day."
"Yeah," she continued, wiggling her hips and giggling, "we're having chilly for lunch....with beans."
Now, Chris was really worried. Shannon never bluffed when it came to her ass; when she said she was going to fart in his face, she did it.
"Or sitting on my face," Chris added.
"Oh, come on," She teased, "you know you like it."
"I also like hot showers," he chimed in wittily, "except any pleasure goes away when there's a gas leak."
Shannon giggled a bit at the witty comeback, then continued: "So, is it a bet?"
"Wait a minute," Chris protested, "what do you get if you win?"
Shannon giggled rather sinisterly, then smiled a Cheshire smile.
"Well, If I win....I get....you."
"What do you mean 'You get me'?!" Chris asked harshly.
"If you don't win, I get to do whatever I want with you for the week!" Shannon replied.
"I'm NOT going to agree to THAT!" Chris stated, flabbergasted at the very notion.
"Oh, come on," Shannon whined, "What have you got to lose?"
"A lot," he shot back. "I am NOT agreeing to that!"
"Well, what would it take to get you to accept?" she asked desperately. "Anything, just name it."
"I want you to leave me alone this week and let me enjoy my time with no parents." Chris answered firmly. "I actually want to enjoy this summer. I want you to stop wrestling with me, sitting on me, farting on me, putting your feet on me...I just don't like it and I want it all to stop!"
"Don't you like me?" Shannon pouted, actually somewhat hurt.
"It's not that I don't LIKE you, I just don't like you teasing me all the time."
"Chris, you KNOW that you like what you see!" Shannon defended herself, showing off her body like a model. "I've caught you staring at me plenty of times; you're just too afraid to admit it."
"Look," Chris attempted to explain calmly and rationally, "I'll admit....that I do think you're.... kinda cute, but not when you treat me like crap. I....can't control my hormones, they kind of take over. I've never thought of you as anything more than my babysitter, though now I really don't need one."
"So, you DO think I'm pretty," Shannon blurted out. Then, the sing-song voice started. "Admit it, you love me, you wanna kiss me, you wanna date me."
"Knock it off, Shan!" Chris protested. I do NOT like you like that! You're like TWICE as old as me!"
"So," Shannon shot back, "you're saying that if you were OLDER, we'd hook up, huh?"
"NO, and I'm not talking about this anymore!" Chris said, having had enough. "Furthermore, I'm NOT taking that bet!"
Shannon started to get discouraged, displaying a sense of anxiousness, but came up with a sneaky idea.
"I tell you what, Chris. I'll sweeten the deal, just for you."
Chris started to get down of the barstool, but Shannon grabbed his arm quickly and firmly.
"Just listen," she pushed, still having a hold of his arm, "if you take the bet, not only will I agree to all your terms and promise to leave you alone for the rest of the week, provided you win, but....I'll give you something I think you'll REALLY like."
"I probably won't," he responded.
"Oh, I'm pretty sure you will," Shannon rebutted, pulling Chris closer, much to his dismay. "If you win....I'll give you...." she paused for a moment, glancing left and right as if to see if anyone else was nearby to hear, "....I'll give you....a peek."
Chris's ears immediately perked up, both for surprise and confusion.
"A peek?" he replied, befuddled. "What do you mean 'a peek'? A peek at what?"
"You know," Shannon repeated, her eyes motioning toward her chest, "a peek."
Chris was completely speechless, his mouth hanging open in utter awe. He couldn't believe what he had just seen or heard, and Shannon just kept going.
"And not just for a second," she added, "I'll let you look as long as you want."
Shannon knew she had him; it was a win-win scenario for her now: if I win, he's mine for the whole week, she thought to herself, and even if I lose, he'll be putty in my hands after staring at my tits.
Chris didn't want to even contemplate the bet, but it was impossible now. How could he pass up this chance? Everything left to his imagination would be gone. He wouldn't have the impulse to stare anymore: he'd already know; that might be worth it.
But what if I LOSE, he thought to himself, do it really worth it to be at Shannon's every whim the entire week, just for a look at her boobs?
"You're joking," Chris said, dubious to the sincerity of the offer.
"Mm-mm," Shannon objected, shaking her head.
"Seriously?!" Chris ejaculated, still in disbelief.
"Mm-hm," Shannon reaffirmed, nodding her head sweetly.
"And if I win, you'll leave me alone for the WHOLE week?"
"Mm-hm," Shannon repeated, again nodding her head. Shannon could see the conflict in Chris's mind, so she threw one last punch:
"Who knows, maybe I'll just decide to walk around TOPLESS at random points this week....you know, IF you win."
Now, Chris was completely hooked. His boner was growing bigger by the second, and Shannon knew it by the way he was squirming in his seat. Chris didn't really want to but this was too good of an opportunity to pass up; besides; it this didn't seem like a difficult challenge, as HIS cup had about half of what Shannon's had.
"So," Shannon continued as she pushed Chris's glass towards him, grinning slyly, "is it a bet?"
Chris thought about for one last moment before making his final decision: "Deal," he blurted, still having some reservations.
"Cheers," Shannon said as she raised her glass. Chris obliged.
"On three," Shannon said. "One...." Shannon signed 'two', then 'three' and the chugging commenced.
Chris immediately started drinking from the glass, trying desperately to win, but as WAS the first time he'd ever had a beer, he started gagging: it tasted like crap; still, he forced it down, trying to ignore Shannon and concentrate on winning.
When Chris finished, he slammed the glass down on the counter at the exact moment Shannon did. Damn it! A tie, he thought as he heaved a sigh. Chris almost felt like throwing up; his head was spinning and he started feeling dizzy.
I can't be drunk already, he thought; that's when he realized something was wrong....WAY WRONG!