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Author's Note: Ever have a story that screamed away in your head until you got it out? Yeah, this was like that. This is longish, but reads quickly because it is dialogue heavy. I wanted to try one big story as opposed to the multi-chapter thing. For the squeamish - there's some, you know, moderate butt stuff in places here. Sue me.
~~~***~~~
Jessica paused in the dark only a few yards from the rear of her house and crouched by the base of a large pine tree. She'd heard giggling on her walk home from her friend's house. Sure enough, her brother, less than 20 feet away, was with his new, hot, but incredibly vapid girlfriend.
"So you want to see them?" she heard the curvy blonde tease. Jessica realized the question was largely rhetorical. She wondered if the blonde could spell 'rhetorical' or use it in a sentence.
"Yes, please." Well, at least her brother was polite.
"Okay." The blonde yanked her yellow tank top over her head. "Ta-da!" Her large D-cup breasts sprang free into the cool night air.
"Wow, they're amazing," his compliment sounded sincere.
"Now pull down your pants, I'll show you something amazing," giggled the bare-chested girl as she fell to her knees.
Jessica watched as her older brother was serviced behind their tool shed. It turned out that the kneeling girl's skills weren't linguistic - they were oral. She watched as the blonde's head bobbed expertly. Instead of running away or getting nauseous as one might have expected, Jess watched with keen interest. And her mental wheels began to turn.
~~~One Year Later ~~~
"Hiya Winnie. Hey, have you ever had a guy whose dick was so big that when he stuck it in you he didn't even need to move it and it already felt good?"
The casually delivered question nearly caused him to spew breakfast cereal all over the couch. It was wrong on three levels. First, "Winnie" was just an irritating nickname for Winston. (Winston's full name was Winston Churchill Kendall. Only a history professor and his avid anglophile wife would conceive of naming their 21st century American son after Britain's greatest statesman). The point is he was a guy. And no heterosexual man wants to hear a question like that. Ever. Second, this was not the kind of talk people had over breakfast. Third, it was his baby sister asking the question.
This was a little game Winston and his sister Jessica had started to play recently. Well, it was a game that Jessica played with him anyway. It involved her surprising him periodically with nasty thoughts like this that made her sound like a slut at the same time they accused him of being gay. But he wasn't gay. And, as far as he could tell, Jess was not a slut - although you wouldn't know it based on the things that popped into her head and then came flying out of her mouth.
Her odd behavior was not entirely out of character - Jessica had always been clever in a crazy sort of way. She liked to make things up. She was good at it. She had an amazing imagination. Lately she'd been using it towards nefarious ends. Torturing Winston like this was a prime example.
It hadn't always been like that. He thought back to the days of "stolen kisses." He missed that nicer game.
Little Jess was barely seven years old - he was eight - when she explained the rules for stolen kisses to him. She even summarized the history of the game as having been played on the palace grounds by the ten illegitimate children of King William IV. She'd said she read it in some notes their Dad left out for his research into 19th century British royalty.
According to Jess, the game's object was to sneak up on another contestant and surprise them with a quick kiss on the lips. If the frontrunner got three smooches ahead of their victim, they could demand a favor. Usually it meant doing one of their chores or loaning out a favorite toy for the day. Then the kiss count reset to "even" and the game began again.
Of course, she'd made the whole thing up.
They played the game for years until she'd turned twelve. Puberty made her tall, gangly, shy and awkward. She didn't want to kiss him anymore.
As for Jess's sick new I'm-a-slut/You're-gay game, well, he chalked it up to her being bitter about him leaving for college and sticking her all alone with their parents for the last year of her high school term. But in the past six months, her comments had been getting increasingly explicit. Stuff he'd never even considered. It was a little unsettling.
The present 18 year-old Jessica was a tall beauty. At 5'10" she was only four inches shorter than Winston. She was naturally athletic - the captain and best outside hitter of her high school volleyball team. She had filled out nicely since her awkward pre-teen days. Even Winston realized that his kid sister's long slender legs were dynamite in a skirt and she was the only girl he'd seen that actually made those strange women's volleyball bathing suit bottoms actually look good. In fact, male fan attendance at the girls' volleyball meets had increased dramatically when word got out about his hot little sis.
Overall, Jessica's dark hair, large green expressive eyes and general facial features made her look very much like a young Jennifer Connelly, circa Career Opportunities. The likeness was uncanny, with one particular difference - one that chafed her to no end - Jess had small boobs. If her bikini tops were any indication, Winston estimated them at an A-cup. They were cute, round, and perky. Still, she raged at their smallness.
Boobs aside, Jessica was literally a model, or had been. She had done a fair amount of print and TV clothing modeling in her early teens. For awhile there, she was a go-to model for department store advertisements for jeans and skirts. Her perfect little heart-shaped ass could make just about any clothing look good.
Her parents had put a stop to the modeling when Jess's high school grades had slipped though. It took up so much time that she didn't even put up much of a fight - a blessing. Jess's particular blend of smart, pretty, and bold meant she usually got her way with their parents. She also wasn't above a little dirty pool when it suited her either. For these qualities, their dad called her "the irresistible force."
Winston was her flipside - stable, cautious, rock solid and honest. Winston was, and always had been dependable. When he put his mind to it, he could even manage to keep his sister in check. Their sometimes comedic battles growing up inevitably led to him being dubbed "the immovable object."
During what would have otherwise been a quiet family dinner the night before Winston went back to school after his spring break, Jess dropped her sizeable bomb.
"I'm having breast augmentation surgery in three months. Right after I graduate. I want it over with before I start college in the fall." She said it casually like she was commenting on the weather and she did it just as Winston had stuck a forkful of cake into his mouth. She seemed to enjoy doing this sort of thing while he was trying to eat.
"What?!" cried everyone at the table.
"Out of the question," their father objected.
"I wasn't asking permission, Dad. I was letting you know."
"We are not financing this," he replied calmly.
"No prob. I'm paying for it." And there was the trump card his sister had never played. Jess's modeling stint had brought in some pretty good money for a little over three years. Their parents put three quarters of it towards her college. The last quarter they'd given her and she'd stuck it into a savings account. She'd never touched it. Not even a penny. She drove their mom's old car and waited tables on the weekends with her friends for spending cash. It was almost like she'd forgotten about the money.
In the middle of what should have been a titanic blowup, their mom kept quiet. It was partly out of her habit of deferring to her husband, but mostly because she didn't have much of a leg to stand on. She'd had the same surgery ten years earlier. Small boobs, and a desire to remedy that perceived flaw, ran in the family.
"Who's doing it?" her mother asked instead.
"Dr. Nelson." Jess delivered the reply smoothly like she'd been expecting the question. She had expected it and she'd sought out the same surgeon who'd operated on her mother. Even Winston had to admit that was pretty slick.
"Nobody will be around to help you with post-op care. You're mother and I are going to be away for the whole summer," their Dad reasoned. He was taking a sabbatical from the university and they were both headed to Africa on a series of safaris and archaeological tours. It was a legitimate point but it was also a sign that Jessica was winning the argument. The dispute had shifted towards a challenge to her timing.
Jessica smirked, there was a clearly an answer in waiting for this too. "Winston will take care of me." She turned to smile at her brother sweetly. "Won't you, bro?"
"Huh?" was all Winston could get out.
His mother did a better job of articulating the awkwardness of the situation. "He's your brother, he shouldn't be..."
Jess cut her off. "Pfffh, he's gay. I'd be more worried if I was his brother and getting a penile implant. Plus, he's at least partially qualified - he IS studying to be a nurse."
"For the hundredth time, I am NOT gay," Winston seethed.
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