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.
Jess brushed off his frustration. "Whatever. Are you going to make sure I don't die or end up permanently disfigured or not?
Winston briefly considered suggesting that their Aunt Barb could come and look after Jessica but the irony was she actually was gay. And frankly, she was a bit of a wackadoo. She talked about alien abduction. A lot. Nobody rushed to sit next to her at holiday dinners.
Winston weighed the available choices. He knew his sister well enough to understand that changing her mind was not an option. His parents couldn't back out of their trip - a small fortune was tied up in their summer-long plans. His sister's friends were sweet but, frankly, none of them were terribly bright - they were a collection of cute jockettes. They'd be no help either.
After circling the predicament, Winston finally let his own self interest tip his decision - he had been looking forward to the approaching summer completely unsupervised. He knew his sister was too. If he agreed, there'd be nobody around to spoil it.
"Fine," he sighed, "I'll do it."
"Thanks, Tunny," his sister said softly.
Winston looked up immediately for two reasons.
First, the genuine appreciation in Jessica's voice was nearly unrecognizable. He realized it was a sad commentary on their relationship that jeers and sarcasm were the norm and kindness felt out of place. But right now Jessica's gratitude was real. No sarcastic remark followed. She didn't roll her eyes either.
Second, and more importantly, "Tunny" was a nickname that Jess hadn't used for him in years. When she was little, Jessica couldn't pronounce "Winston" so she'd latched onto its last syllable "ton" and that eventually became "Tunny." He watched her nod then exhale slowly. Her shoulders relaxed too. He felt her smooth leg brush up against his under the dinner table. When their eyes met again, she mouthed the words "thank you" at him silently.
He only then understood that this had been the last potential weakness in her plan. If he'd balked she might have been screwed. She had been depending on him to come through for her. This was an interesting turn of events.
They cleaned up after dinner and everyone went their separate ways that night.
The next morning, Winston was heading back to college. Jessica helped him load his things into his car. As they were trading goodbyes, Winston said his peace.
"Jess, about your surgery…"
She smirked. "What about it? My mind's made up, Tunny. No changing it. I've been thinking about this for awhile."
"I know better than to try to change your mind, my little pigheaded sibling. It's just... if you're doing this has anything to do with the teasing I used to give you."
"You mean how you called me 'LT' - 'Little Tits' that one summer? The whole summer?!"
"Yeah, I'm really sorry about that now."
"Thanks, Tunny. That means a lot. But no, I'm doing this for me. I want a nice big set of boobies," she made a funny face as she held her hands out in front of her slender chest.
"Fine, just don't go freakishly big, okay? You're pretty already, sis. Go too big and people will only be looking at your chest. They'll miss out on the rest of you."
Jess's hazel eyes went large and soft at the unexpected compliment. "That was one of the sweetest things you've ever said to me. I'll think about it. No promises. If it makes you feel better, it might help if you call me 'BT' for a little awhile after it's done. It might soothe my pride."
"That has got to be one of the weirdest requests you've ever made."
"Meh, it's a girl thing. How would you know, what with being gay and all," she needled him.
"That's it, I'm leaving before we get into a fight."
"Suit yourself. Be good at school OK? Don't suck too much dick."
"Yeah, Yeah. I love you too." And off Winston drove to school.
Almost three months and a decent round of finals later, Winston came home. His parents had hopped their flight to South Africa two days before to join their first safari of the summer. He called his sister from the car on the way home to let her know he was coming.
She bounded out the side door to greet him as he pulled in the drive. Winston's eyes tracked up her incredible long, tapered alabaster legs sheathed in a small pair of khaki shorts. Her tiny blue tank top showed a bit of her smooth flat belly. Her long dark hair was damp and gathered in a loose ponytail that swung wildly as she dashed across the driveway to crash into him as he got out of his car. She hugged him fiercely.
In the crush of her embrace, he felt the full length of her tight, athletic body. His sister was a firm in all the right places. He also smelled her rosemary-mint shampoo. She guarded that shampoo jealously. He flashed back to her shrieking at him a few years ago when he'd used some out of curiosity. She'd smelled it on him immediately and flipped out. Smell sometimes triggered odd memories for Winston.
"Err... happy to see me then?" he said, a little confused. What had come over her?
"Very happy! This is day number one of the best summer ever," she said into his chest.
She was in good spirits. He credited it to their parents' absence and the fact that her boob surgery was only two days away.
She helped him carry his stuff inside and even up to his room.
"You unpack. I need to shoot mom and dad a quick e-mail. I promised I'd tell them when you got here."
"Okay," Winston watched his sister leave, still wondering at her improved behavior.
Over the next half hour, he unpacked his things and shoved the assorted duffel bags into the closet. He was sitting at his desk stuffing books onto the bookcase above it when his sister gently knocked on his doorframe. Her eyes kept darting down to her feet shyly. Her cheeks were a little flushed.
"Tunny, I kind of have a favor to ask. This is going to sound weird but Doctor Nelson wanted me, well, you to do something before my surgery."
"Yeah?" Winston had resumed stuffing books away.
"You... ah hah ha... you need to look at my boobs," Jess stifled a nervous giggle.
"Huh?" his head whipped back to her. She had his undivided attention now.
"So you have a reference point," she winced. "So if something looks funny later you'll be able to tell."
"Hey, what do I know, I didn't argue with the guy. He's the surgeon," she shrugged.
"I, ah, okay," Winston wrapped his head around what was going to happen. "So... when do you..."
Jess didn't answer. She just took two steps forward and her hands drifted to the bottom hem of her little tank top. She looked up from the floor finally and her eyes locked on his. She caught her bottom lip in her teeth and gnawed at it gently.
"What? Now?" Winston asked.
His sister nodded. She started pulling her shirt up, exposing more of her smooth flat belly. She paused, and through the shirt she pleaded with Winston, "First, promise no laughing or teasing okay?"
"Promise," Winston replied fidgeting in his chair. His sister was beautiful and like any normal heterosexual male who laid eyes on her he'd wondered what she looked like naked. Now, with very little warning he was going to find out.
She resumed pulling her shirt off. Winston held his breath. Jessica's round pert little breasts popped into view. They were the definition of perky. Their skin was a smooth unblemished ivory like the rest of her. Her light pink nipples were perfectly centered on each breast. His mouth fell open. Lord, his sister truly was hot as hell. He used the moment it took for her to get the shirt over her head to compose his face.
"Soooo... these are my boobs," she said sheepishly, nodding her head. Her lips were pressed together in a line.
"Yep... those are my sister's boobs," he chuckled, "Sorry, I was laughing at what you said, not at your body. You're a good looking woman, sis."
"Thanks. There's more though. The doctor says you have to touch 'em beforehand too so if you need to pulpitate me..."
"Palpate," Winston corrected automatically.
"Yeah, that's it, palpate me after the surgery you'll be able to tell if something's weird."
"So, you want me to feel you up too?" he smiled, trying to make light of the situation. Humor had always been his defense mechanism for awkward situations. Hers too.
"Doctor's orders." She shrugged as she stepped forward until she was barely a foot away from Winston. Seated, he was eye level with her chest. "Try not to enjoy yourself too much. If you switch sides, you'll piss off your boyfriend." She smirked.
Winston's hands, thankfully perpetually warm, rose until he began to gently touch his sister's left breast with the first two fingers of each hand as he had been taught. Her breasts were warm and soft but firm. If his hands shook a little, his sister didn't notice or pretended not to. She looked at the bookcase behind him as he worked, feeling first one breast then switching to the other one.
Reluctantly, he let his hands fall away. "All right. I now know what your boobs feel like."
Jess looked down to meet his eyes again and smiled. "Well, that wasn't as bad as I thought it would be. Hey," she reached over him to his bookcase. The sudden forward movement brushed her right breast against Winston's forehead. Winston stiffened in various places in response. "Ooops, sorry. I was reaching for this." She held his little digital camera. "Does this thing still work?"
"Here, take a few 'before' pictures of me? So I can remember what I looked like before my new superboobs." She handed him the camera and stepped back.
Winston knitted his eyebrows together.
"Go on. You can e-mail them to me."
He snapped a front picture of her. She turned to each side. He took more pictures. She got a bit silly and started posing, making funny faces, pushing her boobs up between her arms, then cupping them in her hands. Two dozen pictures later, she thanked him, picked her shirt off the floor and left.
Winston was left sitting in his room. Less than an hour from getting home, he'd seen his sister topless, felt her boobs, and now had pictures of her to boot. What was it his sister had said - "this is day number one of the best summer ever"?
Day number two would top it. He didn't even have to wait all that long.
It was late the next morning, nearly noon, and Winston was finally fighting off the vestiges of his hangover from drinking while reuniting with his high school buddies the night before. Jessica knocked on his closed door then opened it a crack to peek inside.