Chapter 1: Brittany

Fifteen-year-old Rob Kramer was worried sick about becoming a sixteen-year-old virgin. He wasn't a bad looking guy. Just an ordinary kid. Brown Hair. Brown eyes. Average build. Not tall enough to be a basketball legend and not wide enough to be a fullback. He rarely got less than a C or more than a B. Rob thought of himself as Mr. Average. He had a few brief encounters with girls but sexually had never gotten past the feeling-up stage.

Lately, Rob was having a hard time understanding the mixed feelings he was having about his twelve-year-old sister. Even though he was less than three years older, he had always been protective of her. Sure, they argued and fought as typical kids always did, but he still always made sure that she caught the school bus, had her lunch and the other things that a protective brother would do. And he knew that she looked up to him as a "big brother" even though she did sometimes act bratty.

Brittany was always "Little Miss Perfect". Straight A's in school. Room always immaculate. Her clothes always matched. Her chestnut brown hair was always precision cut with perfectly straight bangs in front and straight across her back. She had big brown eyes that could radiate whatever expression she was feeling. They had a habit of making people want to do Brittany's bidding. Until now, he had always thought of her as a little kid. She had been in elementary school. She never paid attention to boys. Her body had not yet started the adolescent development... until now.

The first thing he noticed was the way she started wearing adult clothes. Her washbasket always used to be school uniform, plus tee-shirts, jeans, socks, white cotton vests and pants. Now it contained short skirts, brightly-coloured silk blouses, wispy panties and almost-invisible brassieres. He noticed all this because, since Mom left, Rob and Brittany had shared most of the chores, including loading the washing machine. OK, she was turning from a little girl into a big one - but where was the money coming from for all this? Rob thought about asking his dad, but decided that if Dad wanted to spend extra money on his little girl to make up for not having a mother about the place, asking about it might sound like sour grapes.

So, Rob was fifteen and horny. Handling his sister's scraps of underwear had stirred his loins pretty badly that evening. As he sat in the chair, the thought of jacking off made him want to go to bed. His Dad sat watching TV and drinking his third glass of wine... he would be asleep soon... usually right there on the couch. "Night, Dad," he said, getting up to go upstairs.

"Goodnight, Robbie," his dad said and then added, "make sure Brittany's light is out on your way upstairs."

Rob didn't remember the light until he had tossed his levis over the chair and started to climb into bed, anxious to start stroking his cock. He knew that if his Dad noticed the light he would come upstairs to turn it off and he didn't want to risk him looking in and maybe catching him beating off. He started to grab his levis but then shrugged and proceeded without them. It would just take a second and it was just across the hall. Dressed only in his jockey shorts, he went to his sister's room as he had done several times. She left the light on a lot, especially if she thought there was a chance of a night time storm.

He entered her room and as by familiar feel turned off her light. He was surprised that the room did not darken and noticed that she had left the closet light on as well. "Damn," he uttered under his breath as he crossed the room to turn it out. On his way to the closet he stepped on a pair of his sister's panties. When he looked down and saw them, he looked next over to his sister. She slept in an oversized tee shirt and was on top of the covers, on her stomach, her face buried in her pillow. The thoughts that quickly ran through Rob's mind frightened him but the fear of getting caught was quickly overcome by the excitement of getting away with it. If Brit had nothing on under that shirt and he could lift it up without her waking, he could have a great view of his sister's butt. Wow. That would make his upcoming masturbation session worth the wait.

He picked up the panties in his hand and closed and locked her door on his way to the bed. The dim closet light was perfect and just enough light for him to see his sister clearly. Then, realising that if she woke up that there would be hell to pay about the locked door, he opened it again. He could hear snores over the sound of the TV downstairs, so the chance of Dad spotting him was zero. Now, if she woke, he wasn't doing anything more than covering her up. He went quietly over to his sister's bed and stood beside it for a few minutes watching her sleep. Her breathing was deep and steady and he was sure she was asleep. Brittany always had been a pretty sound sleeper and hard to get up for school in the morning.

Rob's heart raced so loud that he could hear it as he reached down and gently lifted the bottom of his sister's shirt into the air. There it was. With the glow of the closet light bouncing off of it, the girl's round, smooth butt looked like a beautiful sculpture. Rob was having trouble breathing quietly because he was so excited and his heart was pounding wildly. His cock reached full stiffness almost immediately. After a few minutes of staring at his sister's cute petite little ass, it was too much for him to bear. He took his free hand and started massaging his cock through his jockey shorts.

Slowly, he put Brittany's shirt up with the bottom of it just above her waist. Now with both hands free, he held the front of his shorts down with one hand while he stroked his cock with the other. This was the best jackoff he had ever had, with a girl's bare ass just a couple of feet from his erect cock. Never taking his eyes off his sister's bare ass, Rob went into a full stroke masturbation, forgetting the short, slow, quiet strokes he had started with. Suddenly, with no warning at all, his climax erupted. He managed to snap his shorts over it, catching the torrent of cum as a sticky mass inside the material.

Rob waited for the feelings to subside, for his breathing to return to normal, for his legs to stop wobbling. Then he carefully replaced her shirt, switched off the light and went back to his room. The ruined shorts would have to be hidden until his next washday, but that was a small price to pay for a jackoff like that. And there would be more to come when he replayed the scene in his mind.

For the next week, he did exactly that. Four or five times a day the vision of a cute little backside, glowing in the soft light from the closet, would come into his mind. He made his way to the bathroom, straight away if he could, or as soon as possible if not, and jerk off. A couple of times he was stuck in a lesson, and had to wait. The first time he felt that his erection was all too visible as he stood up at the end and stumbled out.

Rob, like any fifteen-year-old boy, was sensitive about that sort of thing. He thought about it, and came up with a pretty neat scheme. He made a slit inside his pants pocket, and made sure that he had a wad of tissue handy. The next time it happened, his hand took the tissue through the slit and wrapped it around his cock. Now all he had to do was take his daydream to its conclusion (gently... no sudden moves or heavy breathing!), wait until the tissue had soaked up his cum, and remove it. Fine entertainment - better than Geography, any day!

A week or so after his first adventure, he found that once again Brittany had left her closet light on when she went to sleep. Ah! A chance to refresh his memory!

Rob had played out this moment so often in the last week that it was like being back in his daydream. Again, he tiptoed over to her bed and stood beside it for a while watching her sleep. Again her breathing was deep and steady. Again his heart thumped as he reached down and gently lifted the shirt to her waist. Again, he started to jerk off. Suddenly, Brittany moved! He panicked and was away from her and by the door in an instant. It took him a minute to get back control of his shaking hands, and in the interim he looked back at the bed. Brittany had turned completely over! She was still asleep, but this time she was on her back. It only took him a minute to realize that he could have the same view of her pussy that he had had of her butt. In the time that it took him to get over to the bed, his panic had subsided.

Again, Rob lifted Brittany's pajama-tee shirt and gasped quietly at the sight of her tender, hairless mound. Rob lay the shirt down just above her navel and again started his jerking off, watching his sister's bare pussy while he did it. He was once again into a steady rhythm when Brittany moved again. This time he didn't panic and his only reaction was to allow his undershorts to snap back up over his swollen cock while he watched carefully to make sure that she wasn't going to wake up. If she did, he was just going to cover her, right?

This time Brittany's move allowed both legs, which had been raised slightly and bent at the knees, to flat in opposite directions. The result gave Rob a clear view of her slit, little hole and all. Throwing caution to the wind, Rob pulled his shorts down below his hips and stroked his stiff cock as he massaged his balls and he scrutinized his sister's open pussy below him. He didn't realize until it was too late to do anything about it that his cock was erupting, spewing wads of cum all over the bed and his sister below him. By the time he returned to reality from the fantasy world of his orgasm, a ribbon of pearl glistened, reflecting the closet light, as it crossed his sister's bare, flat stomach. Another wad had impacted the inside of her thigh and flowed down her leg until it soaked into the bedspread. Yet another had made its way to the top of her mound where it impacted just below her soft patch of hair and cascaded down her crack, crossing her open hole and dripping the rest of the way down the crack of her ass making a pool where her butt met the bedspread.

It took Rob a few moments to get his senses and even longer to catch his breath. Thinking rationally now, he decided not to try to clean up his sister for fear of waking her. "The shirt should soak up the semen," he thought, "she won't even notice it in the morning." After one long last look, he lifted her shirt and covered her. Quietly, he turned towards the closet to turn off the light. He was horrified to hear her voice behind him. "Yuk! Look what you've done, Rob!"

A hundred explanations cascaded through his head, but he knew none of them would work. She hadn't sounded sleepy... she might have been awake through the whole thing, deliberately exposing herself!

Rob turned back, head bowed. She was sitting up, feeling between her legs.

"You'd better fetch me a towel, you creep. While I think about what I'm going to tell Dad."

He fetched the towel. "I'm sorry, Britt... I don't know what came over me. Please don't tell Dad. He'd be so hurt."

"Haven't you seen enough?", she snarled. "Turn around while I clean up." Rob turned, redfaced. "Perhaps not Dad. Maybe I should tell a few of the girls at school. Or some of your classmates?"

"Christ, no! I'll make it up to you, somehow. Anything!"

"Hmmm. You can do my chores for a while. I'll do some, while Dad's around - but you do the rest."

"Sure, sis. Anything you say."

"And you can give me a hundred dollars."

"What! I don't have a hundred dollars!"

"You're careful with your money. I'll bet you've got fifty in your room right now, and a lot more in your savings account."

Rob had. But not for long. Over the next few months, she had two thousand dollars from him. All his savings. His allowance. His paper-round money. Money from selling his computer games, his stamp collection... Money he borrowed from friends, knowing he wouldn't be able to repay. Every time he complained or pleaded, she reminded him about the cum-soaked sheet and tee-shirt, carefully hidden away. Her sheet, her shirt, his cum. And he knew he'd never be able to explain to his father.

"I used to like you. Everybody does."

"Maybe they don't know me very well. I like being a bitch. I love the sheep-eyes expression on your face when you try to explain why you can't pay me what you owe."

Rob ground his teeth. "One day, Britt. One day, you're going to need help. But you won't get it from me!"

She smiled sweetly. "Oh, yes I will, brother. If I need something from you, I only have to ask. Don't I? Don't I?"

She was right, of course. She had Rob over a barrel. His masturbation fantasies grew darker. They still usually involved Britt, but there was no sweetness and light now. Instead she was tied to a bed, being whipped. Or facing a loaded gun and pleading for her life. Meanwhile, he had to pretend things were normal. Britt's thirteenth birthday came round. He asked her to leave him some of his allowance, to buy her a present.

"How sweet!", she laughed. "You want to buy me a present."

"No, you little piece of shit, I don't. But I have to keep up this charade for Dad's sake."

"Wait here." She went to her room, reappearing with a small jewellers' case. "Give me this."

'This' turned out to be a fine gold chain, with a gold pendant set with some sort of semi-precious stone.

"And where would I have found the money for this sort of thing from?"

"You saved up. Because you love me so much!"

With no real choices in sight, Rob wrapped the case, and gave it to her on her birthday.

"Wow, Rob! This is really neat, thanks! What a marvellous brother I've got, hey Dad?"

"You certainly have, Britt. Well done, Rob! But that must have cost a lot of money!"

Rob muttered something about her being worth it, and needing something to set off her fine new clothes. His ears went red as he said it. Everyone thought he was being shy about being 'found out' in caring for his sister. Only Brittany and Rob knew different.

He'd searched for the incriminating shirt and sheet, but not too hard. Even if he found them, Brittany's accusations would work. She'd tell Dad, he'd believe her, Rob would go red. He was guilty, how could he not look it? But what was she doing with all the money? He decided to find out. Hell, he had plenty of time now. With no cash, his social life was shot.

At breakfast one day, as she did two or three times a week, she asked Dad if she could go home to a friend's for tea and study, and make an evening of it. He waited until she'd gone to school.

"Dad? OK if I stay out for a bit, too?"

His father grinned broadly. "Sure. You've been hitting the books pretty hard lately. About time you had some fun. Are you ok for cash?"

"Well..."

"Hah! Thought so! It's a girl, isn't it? Don't worry, I won't pry. Remember what it was like for me. Will twenty do?" He offered the money.

Rob managed a smile. "Thanks, Dad. I won't be too late."

After school, he lurked behind a wall, watching for her. She emerged with a couple of her friends, Nicole Ballard and Melanie Regan, and he followed them to Melanie's nearby house. A big, expensive house, with a couple of big cars outside. A half-hour later, they emerged, dressed in very smart gear and looking at least five years older. That told him where his money was going. Keeping up with rich-bitch mates!

They didn't seem to do much. Just walked to a nearby bar, ordered drinks, chatted amongst themselves and with others. There seemed to be some light flirting going on with some of the boys, but nothing that would give him any kind of lever with her. Was she drinking alcohol? Rob didn't know, and couldn't work out how to check. The three girls left, went back to the same big house, and Brittany left a few minutes later, back in her uniform and with her school bag.

A couple of days later, the same thing. This was getting pretty boring! He had nothing on her. Ok, she wasn't studying like she said, but she was still getting straight 'A's, so Dad wouldn't worry about that.

Rob decided to watch her one more time. This time, it was different. After the last lesson, Brittany went into the girls' bathroom. When she emerged, she was wearing dark t-shirt and jeans, and a dark coat. She walked to the shopping mall. On the way she tucked her hair under a baseball cap and pulled the coat collar up. He realised that he wouldn't have recognised her if he'd seen her like that in the street.

Rob followed Brittany into one of the more expensive clothes shops. She didn't seem to be doing anything, just browsing. She worked her way over to a fairly crowded clothes-stand. A woman was holding a blouse up to herself, looking in the mirror. Nearby were several bags, containing stuff already bought in other shops. Casually, Brittany helped herself to a couple of the bags, and walked off. In the next twenty minutes, she did it twice more in other shops. Then, fully-laden, she headed back to the school, which was open late, for pupils who wanted to work in the library. She did another quick switch, and was soon heading home with her uniform and school bag, which presumably contained the stolen goods.

This was more like it! She could no more lie to Dad than he could, he was sure. And all the expensive clothes in her wardrobe would have to be accounted for. It wasn't Dad paying for it, after all. She'd have to own up to a combination of theft and blackmail, which made his teenage sin look very small beans indeed! In fact, he could probably start blackmailing her! Not for money - anything she got, she would have spent on those damned clothes. But she certainly wouldn't be able to object to him stripping her and wanking on her now and again... maybe he could get her to jack him off... perhaps even go further than that... his erection was suddenly painful, and he had to hobble off to the men's room.

A bit more evidence would be needed, though. At least he wouldn't have to get bored watching her with her mates. All he had to do was look for what she was wearing when she left school.

A week later, she followed the same pattern. Anonymous clothes, walk to the mall, steal, walk back. And a week later, the same. Only this time, things went wrong. As she went for her heist, the victim noticed.

"Hey! Come back with my things!"

Brittany dropped the goods and ran, but a security guard came after her. He grabbed her outside the shop, by the upper-floor railings. She fought to get away, but he had her arm in a tight grip. Two more rent-a-cops were heading towards them. She reached into her pocket and pulled something out. Suddenly the guard screamed in pain, clutching his eyes. Rob watched her running for the exit, while all other eyes, including the other guards, were on the man as he staggered blindly to the railings, and fell over.

There was an endless pause, followed by screams from above and below. Rob left, and headed home.

He got home before she did - she'd had to go via the school. But Dad was there, and there were chores to be done, so the confrontation would have to be put off.

The three of them watched the local TV news together. The guard was in hospital, not expected to live. He had a wife and two small children. Police were looking for a boy, age 13-17. They had some good fingerprints off the can of mace that the attacker had used. Dad tutted, and so did Rob. Brittany, he saw out of the corner of his eye, looked a little scared and greenish.

The next day, she looked better. She probably figured that she was home clear, with the police looking for a male criminal. They were talking about fingerprinting all the boys in the school. Brittany had said at breakfast what a good idea she thought it was! She was scheduled for one of her evenings out with her friends. Rob wasn't sure whether she'd go, but she did. Good! That left him enough time to look around the house, before Dad came in.

He found her stash fairly quickly, in a forgotten corner of the loft under some old carpeting. Cheque books, credit cards, keys... he removed some, being careful not to leave fingerprints, and dropped them into a plastic bag. Underneath was a stained sheet and t-shirt! These he put quickly into the wash. Now she had no evidence against him, and he had plenty against her!

The following afternoon, they were both in and Dad was going to stay out with friends. Now was his chance!

"Rob", said Brittany, "can you ask Dad for your allowance a bit early this week? I need to do some shopping."

"No, sis. I won't."

"Oh, yes you will!", she hissed, with a venomous smile on her face. "You'll do exactly as I want!"

"Sorry, Brittany, no. I need the money for myself."

"I'll tell Dad... I'll show him."