A Bet, Little Sister?byTheDarkCloud©
Paul stood at the large window of the student residence living room he shared with his sister and adjusted the binoculars he held to his eyes. He looked out onto the beautiful sunny day and the scattered groups of students on the lawns and benches sunbathing, chatting or just fooling around. These really were the beautiful people, especially the young women in their light coloured short tops and shorts or skirts. Paul liked to observe the young women on campus.
He ran his fingers through his slightly curling, short, light brown hair and focused on two girls in particular, sharing a rug under the slight shade of a poplar tree. His sister Julie came at once into focus and he couldn't help a wry smile cross his lips as he saw her body language to the other girl. She was so transparent. Still it would prove to be amusing to watch for a while so he picked up his glass of wine and took a sip as his sister, a masterful flirt, worked her magic.
"You see Selma, guys don't really like kissing so you've got to make the most of it" Julie addressed her younger listener and smiled inwardly at the ease of this task. Really Selma may be extremely attractive, with her deep brown eyes, her silky dark hair and a smile so cute you couldn't help but be attracted to her, but she really was so naïve.
"But Tommy likes our kisses, he said so."
"Selma, listen to me, liking something isn't good. He's got to LOVE it, and once he does you'll have him in the palm of your hand, you can do anything with him. Men are like that, useless creatures that we have to guide carefully around to make sure they get things right for us. Understand?"
Selma, two years younger than Julie and a whole lot unwiser nodded her understanding, but really she didn't. However, she didn't want to let the coolest girl on Campus, Julie Duncan know she was such a dork and so inexperienced. Julie really was so cool to take her time to talk to her like this. I mean a cool girl like Julie could be hanging out with all her other cool friends or with the guys but here she was speaking her, Selma Newton, amazing. Julie was staring intently, almost hypnotically into Selma's eyes and Selma couldn't help reflect upon how strong and sexy Julie came across as being. Julie was 20 years old, had long, dark brunette hair (that until recently had been a bottled blonde), a perfectly maintained face and figure and a habit for wearing the most revealing outfits on campus. And she was spending some quality time with Selma this afternoon. Julie plucked a strawberry from the hamper and held it up for Selma to take a little, tentative bite from, her lips brushing Julie's soft hand in the process.
"You know Selma I really do worry about you, I think I need to show you exactly how to kiss properly, here lean closer and I'll demonstrate."
Selma nearly choked on her fruit and barely managed to mumble back.
"B-But you're a girl!"
'Glad you've noticed' thought Julie as she leaned forward deliberately so more of her cleavage was revealed to the younger girl. She reached up and cupped Selma's chin in her hand and spoke in her most trustworthy voice, maintaining eye contact at all times.
"I know Selma but who knows better what a woman likes and should do but another woman? Here let me show you."
Without another word or action Julie bent in towards her young protégé and planted her big, soft lips on Selma's and passionately began to kiss her. Her feelings confused and not knowing what to do, Selma's body took over and reacted by returning the kiss and when Julie's tongue slipped out and began to probe Selma's mouth Selma's did just the same until these two young , nubile students were French kissing in the full view of the college. But they were in a world of their own and didn't care, Selma's eyes closed and enjoying this passionate demonstration. Those eyes popped open quickly when she felt Julie's hand move under her skirt and start to pull at Selma's knickers. Was this part of the demonstration? Surely not. She should stop this, but oooh! As Julie's skilled fingers found Selma's pussy lips and then her clit she could not find the desire to prevent this happening.
Back in their apartment Paul finished the wine and chuckled to himself, his shameless slut of a sister had done it again. He headed to the kitchen to fetch another bottle and await Julie's return.
She came into the apartment twenty minutes later twirling Selma's red, lacy panties on her index finger, a smile on her face like the cat that got the cream. Paul sat back in the leather armchair by the window and mock applauded her efforts. Julie just held out her other hand for payment of the bet. Paul held out the keys to his Italian sports car, at least making his sister have to come and get them (a minor point but a point scored nonetheless). Julie came forward, bent right forward to get the keys and purposefully gave her brother a revelling look down the front of her loose, low top. She looked up smiling at where Paul's eyes were directed and spoke.
"Mine for the week I believe (the keys) if I provided the panties (worn of course) of the Principal of the University's daughter?"
God the letch was still staring at her tits! At last his stare was broken and he met her eyes.
"Have fun doing it little sis? I looked like fun from where I was watching."
"God no. The stupid little bitch knew nothing, I wouldn't fancy being the boyfriend of that uptight idiot! She wouldn't know what to do with a cock if it rubbed against her lips!"
Paul smiled at this crude comment from her, knowing this to be the real Julie Duncan. She rarely lost the bets he set her, though in truth he rarely lost the ones she set him. They usually involved sex or seduction and played to their, well developed kinky natures. After all with multi millionaires as parents, who showed little interest in them they were pretty much free to amuse themselves in what ever fashion took their fancy. They had a love-hate relationship and although close , seemed to enjoy spiting each other.
"And where are you taking my darling car this weekend, I wouldn't want it damaged you know."
Julie smiled back at her brother.
"I'll see if I can find a real man, one who can satisfy me, I haven't found anybody up to the job yet."
With that comment she exited the apartment and went about the rest of the weekend, it was just mid afternoon Saturday, there was plenty of time for her to find a lay somewhere. A building site, a bar, a truckers diner, Julie wasn't picky so long as he had a big, hard cock to stick in her.
Paul was lost in thought for a moment before resuming his vigil by the window with the binoculars spying his own next target. He watched all the beautiful young girls pass by, recognising some as having fallen for his, not inconsiderable, charm in his three years at the university. Some flash of bright colour suddenly caught his attention and he turned to capture it in his lens. Zooming in on it, it assembled into a blonde haired vision of loveliness. Focussing on her face he did not recognise her and was sure he would have noted her if he had seen her about campus before. Maybe it was her outfit that was throwing him, wearing a brilliant, virgin white, pristine white summer dress that gave her the look of an angel and white matching shoes, it was not the typical attire around here. All too quickly she was gone and Paul was left to his thoughts again, his continued viewing of the people below now cursory and disinterested.
It was a full week before he discovered who this girl that had captured his attention was. She had been visiting the grounds the preceding Saturday, further to joining the University the following one. Her name was Lisa Winters and had moved up from down South with her father joining the University as the religious Pastor. His investigations soon threw up that she was famously a spokesperson for keeping her virginity until she met the "right" man. She had been featured in the papers and TV and was quite the minor celebrity for a few months but the furore around her was all but died down now. And now she was here and Paul was becoming besotted with her. Something that quickly came to the attention of his sister.
Julie came back one afternoon to find Paul studying Lisa's progress across the lawn outside and silently crept up behind him to observe his voyeurism. After some moments she spoke up.
"So what is it about that little goody-two-shoes you like brother? Do you want to corrupt her? Take her precious virginity? Or is she just a fuck for you? Is that it?" there was no hiding the sneering, mocking tone she used.
"You really are a vulgar little piece aren't you Julie? What's the matter, jealous of the attention I'm giving her?"
This last comment seemed to hit home and there was a bit of a stare off, each daring the other to speak the unspeakable truth about their sibling relationship. It was Paul that broke the stare and Julie seized upon that to drive home, what she saw as her advantage.
"Alright Casanova, I'll bet you your famous Duncan charm can't get you in Miss I'm -A-Virgin's panties within a month."
Paul thought long and hard. He didn't want to make this girl another bet, there seemed to be something a bit different about her. But there was something in his genes, it was in Julie's as well, something that powered him towards sexual situations and challenges and he thrust his hand out to shake on the bet in their time honoured fashion.
"A right, your on. What are the stakes?"
Julie smiled malevolently, as she had given this some thought beforehand.
"Oh I thought high stakes dear brother, very high stakes."
He didn't quite like the way she purred these words but asked her what she meant. The atmosphere in the room was heavy and electric as she spoke the challenge.
"If you can't give your little 'angel' a good, hard fucking within four weeks then you are going to be fucked yourself, in your very own bed by James Jacks (James was a fervent homosexual on campus, a real predator he took pleasure in bedding straight guys just to see how they reacted-Julie was well aware how he would react to get a shot at her brother). You'll suck him off and allow him to show you what it's like to be on the receiving end of a big cock in the ass."
She spat this last part out, having heard Paul boast many times of taking girls anally and how he loved anal sex with them.
Paul was taken aback by this challenge and was about to dismiss it out of hand when Julie quietened him and detailed his incentive for succeeding.
"Harsh, eh? But I'll tell you what, if you succeed you can stick this (and at this point Julie groped her brother's dick through his trousers) in any hole you like on my body."
Julie let that comment hang in the air for a second, Paul just staring at her shocked at what she had just suggested. He had been right, she was jealous of his growing obsession for Lisa and this was how she had reacted. This had been a twisted fantasy of Paul's for as long as he could remember, to make it with his sister and here she was offering it up on a plate. Plus it would mean a fuck with the delectable Lisa. How could he turn this down? So he accepted, trusting in his charms being enough to win over Lisa and aware that he would have to live up to his bet if he failed. That was not such an enticing prospect. That night as they lay in their separate bedrooms both brother and sister masturbated frenziedly in their beds, Julie with the image of her cocky older brother being humiliated, on his knees reluctantly sucking cock as she watched, while Paul alternated between fucking Lisa and Julie in a red hot threesome.
For the next two weeks Paul launched a stunning charm offensive, the likes of which he definitely had never attempted before on any of his conquests. At the start progress was easy; Lisa was a very personable young lady who was looking to make new friends and was only too happy to have this handsome guy paying her attention and complimenting her and helping her settle into the University. She was the same age as Julie and in some of her classes, which was both a benefit and a hindrance as it meant he could be speaking to Julie and 'accidentally' bump into Lisa but he was also concerned that Julie may attempt to influence her (though they had rarely interfered in their wagers previously). But by the end of that first fortnight he was somewhat stymied and was feeling more like her tour guide than anything more substantial. And it worried him. So with failure an unthinkable prospect and success such a glorious one he decided he would need some tricks to succeed.
Blackmail. An ugly word but certainly not beneath Paul and he certainly knew enough about many of the girls at this college to unduly influence them. There was Jennifer, who liked guys shitting on her after sex, and Holly who had made some very dodgy videos in her past. Both unprepossessing young students in some of Lisa's class and Paul charged them with convincing her of what a gentleman and a catch Paul was. Paul himself kept up the pressure, delivering flowers and showering her with poetry and compliments, he was the complete smitten suitor. It began to work, Lisa started to see him in a better and better light and was soon believing he could be "the one". But he was running out of time and every time he saw James Jacks around campus he got a cold shiver down his spine.
Julie kept her distance during this whole period from her brother. Ever since she had made the astounding challenge things had changed between her brother and her. No longer were they trading barbs at the kitchen table but instead they were staring intently at the other when they though they weren't looking. What was she thinking? Simply whether she wanted Paul to win or lose the bet. To begin with she was certain that she wanted to see him brought to his knees (literally) and humiliated because of her but the more she brooded on the thought of Paul fucking her the more the idea pervaded her consciousness and the more she thought harder about that prospect. But still, Paul sucking James's cock was quite the thought too and in the end that was what she wanted to see.
With one day to go until the bet expired things were looking bleak for Paul. He had managed to wheedle his way sufficiently into Lisa's affections that he could be described as her boyfriend but pecks on the cheek and slightly risqué chat were as far as he had gotten, and there seemed no indication she wanted anything more at present. That evening as he prepared himself for meeting her he knew he would need to up his game significantly and take a real chance. Julie saw that as well but said nothing and just smiled as he left the apartment.
To this end the evening began in as posh a restaurant as he could find and he made sure to be as liberal with his wine pouring as he could manage. This certainly loosened her up a bit from the very straight laced, proper young lady he had been dating up to that point. And as the alcohol and talk flowed freely and they moved from the restaurant to a nearby bar she became more and more bubbly and vivacious and at last Paul thought all his month of effort and hard work were going to come to some fruition. And as he laughed and joked with Lisa in the bar he looked in her eyes and realised that maybe, just maybe, this could be the girl for him. All the nonsense that his life had been and accounted for up to then was forgotten. Julie and her schemes and plans and bets were forgotten. He convinced himself this wasn't about the bet any more (though he would collect, no doubt about that), this was bigger than that.
Come the end of the night and Paul suggested to Lisa coming back to the apartment for a 'nightcap', she agreed readily, Paul felt his moment had arrived. After all his plotting and scheming and the worry associated with failing it suddenly looked to him that he had a chance to pull this off. Lisa was giggling and giddy, squeezing Paul's hand in hers and acted totally besotted by him. They ascended the stone staircase that led to the apartment and almost fell through the front door. And there all laughing and merriment came to an almost dead stop.
Seated on the sofa was Julie, dressed more prim and proper than Paul had ever seen her and next to her was Lisa's father. They were apparently deep in religious and theological discussion and looked up in almost shocked outrage at this noisy interruption. And then Lisa's father saw exactly who it was that had stumbled drunkenly through the door. The very moment Paul saw him there on the couch, next to his scheming bitch of a sister he knew he was fucked. Lisa sobered up real quick when confronted by her daddy and the two of them disappeared sharpish, with Lisa sending a last longing, pleading look at Paul as she disappeared through the door. He slumped into a chair with head in hands and heard the soft snigger from his younger sister as she headed to her room, her meddling having worked. He had lost the bet.
Paul was in no hurry to rise the next morning, knowing what it would surely bring and when he finally showered and shaved and walked into the kitchen with the bright Saturday morning sun shining through it's windows he was not surprised to find a very smug looking Julie sitting reading the paper, waiting for him.
"Well, well brother dearest. You don't look too good. Something troubling you?"
"That was a fucking low trick last night, that should forfeit the bet right there" he argued but his heart didn't seem into it. Something Julie pounced on.
"Nothing in the rules says I can't ask the Pastor over to brush up on my bible studies. Don't tell me you're welching on our bet, I've never failed to keep mine. And if you had succeeded I would have done my part without complaint."
"You'd have enjoyed it you sick bitch. But no, I'll do it, when and where? I want to get it over with."
The truth was that Paul, like most young men had had dreams involving homosexuality and he wouldn't have put it past him to experiment at some point. But definitely he would have been the one to have his cock sucked and he would have been the one to fuck ass. He'd have probably enjoyed that knowing his love for anal sex. But not this not kneeling before James Jacks and sucking him and surrendering his virgin ass to that faggot, no way. But now he had no choice, to let Julie win by not fulfilling his obligations would be beyond him, so he listened in a daze as his little sister told him what would happen. He would go out and return at two in the afternoon where James would be waiting in Paul's own bedroom for him.
Two O'clock came far too quickly and as Paul inserted his key and entered their apartment it was silent, too silent. He walked on trembling legs to his bedroom and entered to find a hugely cocky James reclining on Paul's bed while speaking to Julie, who was standing by the bed dressed in an incredibly hot, white, lacy Baby Doll outfit. James stood and as he approached Paul there was a look of contempt in his eyes. Paul hated that this idiot would have him like this but at least it was agreed that no one outside this room would ever know about this. James had dyed blonde, frosted hair and clear blue eyes, he was incredibly fit and muscular and as he stood before Paul in white shirt and jeans he instructed him to strip naked and kneel before him. Paul paused and as Julie looked on with a smirk on her face and her hands fondling her breasts he stripped all his clothes off and fell to his knees before James. It did not escape either Julie or James's attention that Paul was somewhat aroused, not fully hard but getting there.
"Julie, do you want to take out my cock and feed it into your bitch of a brother's mouth?"
The brunette never looked sultrier or sexier as she slowly nodded and crossed the room and stood behind James's back. Her slim hands reached around his waist and felt for his zipper. It came down easily and she reached in to pull out a long, thick cock that was already hardening to her touch. As James ordered Paul to open up, and he reluctantly did so, she guided the member into Paul's mouth until it was in and playfully pushed James forward to bury the cock into Paul's mouth.