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Nigel chuckled, evidently sensing her confusion. "The test part is this: if you don't cum yourself, then that's it. We're done, you're free. You get the pill, and I will never, I repeat, never attempt to engage in any sexual interaction with you again. If however..." he smiled "If you cum once yourself... well, it means you do enjoy this... and so whenever you come her you will do whatever I wish, until you have paid off half the debt. Whatever I wish."
Ahh... the bastard! He was trying to ensure he could continue to exploit her for months on end! She was about to open her mouth to respond, but her older neighbour continued.
"If you cum twice, well, then the same deal but it stands for the full time it takes you to pay off the damages."
Cum twice? She almost laughed - she'd never orgasmed twice in one go before. Then her heart sank as she realised the one exception to that: yesterday... at Nigel's hands. Could he do it again?
But Nigel wasn't finished.
"If you cum three times, though..." he grinned wickedly. "If you're such a desperate little slut that you cum three times on my cock tonight, then you will obey me entirely and absolutely, day-in day-out, twenty-four seven, until you pay off the full debt."
Anna's eyes opened wide in outrage - how could he possibly think that was fair? She opened her mouth to give the old prick a piece of her mind.
"How can you think it's ok to expect me to obey you every hour of the day for months on end!" she shot out angrily.
"Well," he chuckled. "That's only if you orgasm three times isn't it?"
Well... true... And she'd certainly never done that before. She'd brought herself to orgasm three times in a day a bare handful of times, but that was counting morning and evening both. Never in one sitting. Still, the other outcomes were horrible enough. Be at his utter mercy twice a week for months! Oh hell...
"It's... it's still not fair," she said. "You already came today - I haven't. You've got an unfair advantage!"
"True enough," Nigel responded. "But, you had ample opportunity to have a little solo-time when you weren't here. And, as I recall, I did order you to cum earlier."
True. Ahh hell.
"It's still not fair!" Anna insisted, though less convincingly.
"Perhaps," Nigel conceded. "But, unless I'm mistaken, you have an distinctly unfair advantage over me."
Anna laughed incredulously, "Oh really? And how is that?"
"Take a look in the mirror, princess," he said. "You're a fucking mint piece of work that any man would literally die to fuck, while I'm... well, I'm what 30-odd years older than you, grey in the head, and not nearly as attractive as the young studs you probably pick up and fuck every second night of the week."
Well... he did have a point there. She was way out of his league, and the only hope he had of cumming with a chick like her was if he watched porn. But the last bit... her face turned bright red in pure outrage! He thought that she was some light-skirt who hooked up with random guys? The prick! She'd only ever had sex with one guy other than Nigel: her dickhead ex. Well, maybe three times if her ten seconds with Dave the night of her party counted.
"Fine," Anna said, sourly conceding the point. "But I am not a slut!"
"Whatever," Nigel said, dismissing her final point. Asshole. She was not! "Besides, I'm willing to give you one other distinct advantage. You'll have complete control over the situation. You're the one riding me: you control the tempo, you control how deep I go. I'm just going to lie back and enjoy the show."
Anna paused, considering. That was a decent advantage... If she could figure out how he liked it, then she could focus on those certain actions and maybe avoid over-simulating herself...
"I'll give you a few minutes to think about it," Nigel said, turning to leave. "Don't take too long though. In five minutes my patience will wear thin and I'll flush this tablet down the drain, in which case... I hope you like babies."
He took two brisk steps, then paused again. "Oh, and if you do come upstairs, make sure you turn on the video camera as you enter the room. If I cum first, you can keep the memory chip, but if you don't... well... consider it a down payment to ensure you stick to our bargain after tonight. Provided you honour our arrangement, no eyes but mine will ever see the footage."
***
And with that, Nigel turned and left his young neighbour kneeling stunned in the open-plan living room. His heart was pounding in his chest. Fuck. He hoped that he hadn't completely misjudged the young slut. He knew that part of her enjoyed their encounters - he'd seen how wet she'd gotten earlier. He knew that she had a deep inner sexual need. And he knew that she desperately wanted to avoid getting pregnant.
And yet, she had proven to be bold and resourceful. Could she figure out a way around his trap? Given time, she would probably spot his bluff, but hopefully he'd instilled enough urgency in her. She could, of course, source the pill elsewhere. But the fact that she was here proved that she wasn't prepared to open up to anyone and that her parents had cut off financial funding for the time being.
This whole setup was a risk. Perhaps a needless risk. But he'd carefully considered it, and there were reasons behind each of his decisions. Firstly, he'd learned through business it made for much smoother sailing in the future if people agreed to something beforehand, and more so if they had a choice about it at the front end. He wanted, craved, to be able to extend his time with his young neighbour, but short of physically restraining her for months - which was completely out of the question for him - he needed to, somehow, ensure that she would stick to an arrangement. Hence, he'd given her the 'choice' to leave. Not much of a choice, but still, it had been offered.
The next part, well, if he could outlast her just once with her in control of the motions then it showed that she actually enjoyed his attention; to him, to the camera, but most importantly it would plant the seed in her own mind. If she came twice, then it would only make that realisation all the more convincing for her. Three times... No. Thrice was a futile target for him, but one that he'd thrown in there in an attempt to build more pressure on the young blonde. Perhaps the erotic fear of complete domination for months would be enough to drive her to her second orgasm.
Besides, he was confident that if she did accept the challenge then he could make her cum at least once. She'd been so close earlier that he was certain she couldn't resist the urge now. If she came once, well, he could continue to enjoy her for some time yet. But, he figured making her orgasm twice was achievable also - he'd done it yesterday after all. And, she'd been driven to the verge a number of times earlier today: with any luck she had enough built up sexual need that was simply bursting to be released. Surely twice was a possibility?
He didn't really have much realistic hope of the third outcome. He'd been with a number of women over his lifetime, and only two of them had ever cum more than twice in one go. His ex-wife had actually managed it on a handful of occasions, but that was once they'd been together for a few years and he'd managed to figure out all the right buttons to press. Even then, it had been a rare occurrence. And the bitch had still cheated on him.
And besides, Anna Wade's juicy young cunt was so incredibly tight and her orgasms pictures of so unbelievably raw ecstasy that he doubted he would be able to last through two such experiences in any case.
Closing the door to his room, Nigel checked the positions of the cameras and waited. His best camera sat on a tripod with a carefully selected angle that would capture a 45-degree front-on view of the busty blonde as she rode him on the bed. That was the one she would need to turn on as she entered. Two other cameras were tucked about the room, partially hidden, and they were already running. Contingency plans.
Surely this film would be enough to force her continued compliance, at least until their agreement ran out. Surely.
That was, if she came up at all.
***
Anna's mind raced. What should she do?
She could leave right now, Nigel had said as much. Except... well except that she couldn't. Not really. Not without the pill. It galled that her asshole neighbour could predict her so easily! He was so confident that she would come to him, desperate for the pill. She had half a mind to leave just to prove him wrong. But her heart fluttered dangerously in total panic.
No. She couldn't leave. It was no choice at all.
Which left her one option: to go upstairs and accept the dickheads 'test'. It was bad enough that he would ram that pole of his inside her tight pussy. If he pinned her down and forced it in, well, at least she could defiantly grasp to the lie that she hadn't wanted it. However, it would be an entirely different matter if she were the one guiding that engorged cock to her own waiting love-hole...
It's still the same: he's still forcing you to do it, she tried reasoning with herself. Even to her it sounded like a complete and utter lie.
Still, perhaps it was a blessing in disguise. She was pretty certain that if he were to ram that thing in her hard and fast that she wouldn't last a minute before cumming, such was her built up tension. But if she were in control... maybe, just maybe, she could finish him off before she climaxed herself.
Could she do it?
She had to, didn't she? She couldn't leave without the pill. And she couldn't allow herself to cum this time. Her stomach did a backflip at the mere thought of having to submit herself to Nigel for months.
Perhaps she could stick to her original plan: do whatever it took to get that tablet, and then just ignore him. The video camera. Well fuck. If she went upstairs then he would have a horribly explicit film of her fucking him, and completely willingly, or so it would appear. Shit, if she orgasmed on camera while riding her neighbour's cock... she really would do whatever it took to keep that video a secret. Twice a week for almost half a year or whatever it was would be a small price to pay to stop her friends and family from seeing that shameful film...
And the bastard knew that full well. Fucking asshole.
The very thought of being caught on camera like that... it made her want spew. No. Surely she couldn't go through with this?
***
Nigel exhaled in relief as his bedroom door opened slowly and the luscious blonde crept tentatively into his bedroom. Despite her clear unease at what was about to happen, she still managed to sway her hips mesmerizingly. Wearing only her purple panties and the dark fitness bra, the sight of her exposed tanned legs, round hips and toned stomach made his mouth go dry instantly.
Hell yes...
As the young blonde glanced anxiously at the camera, Nigel decided to try to draw her attention elsewhere. It wouldn't do to have her so petrified that she ruined his central piece of leverage.
"Glad you made the intelligent decision," he said casually. "Remember the rules. You ride my cock, and you are not to stop until I cum. If you don't cum yourself, then you win, and we're finished. You cum once, and I have you twice a week for about three months. You cum twice, and I have you for double that. Three times, and, well, I'm sure you remember."
The pretty blonde nodded silently, face glowing red.
"When you're ready to get started," Nigel continued, "you can stand in front of that camera and turn it on. Blow it a kiss and a wink, then I want you to completely forget it exists. Unless of course you want to start the whole thing over again..."
She nodded obediently.
"Good. Now, take a few deep breaths to get control of yourself, then no more delaying". He paused. "The only other thing is that you need to be wet before you climb up," Nigel added, and the near-naked blonde scowled at him. "That's entirely for you own good by the way. You do not want to be dry when you try to take a cock this size in your tight little cunt, trust me." He paused again, seeing the comprehension in her eyes as she blushed deeper. "If you need a minute or two, then you can suck my balls while I finger you."
***
The red light on the front of the camera blinked at Anna like a watchful eye as she blew it a kiss. Her stomach churned anxiously as she thought about what that little blinking light meant. Her body, her actions, her shame would be captured and stored for all eternity. Who would see this footage? Would Nigel stick to his word? Could she trust him with that?
After the way he'd taken advantage of his neighbour's innocent daughter? No, she couldn't trust him with anything.
He was right about one thing though - she did need to just try to ignore the camera. So, as she turned her back on it, she turned her focus to the other source of immense anxiety for her.
Nigel lay on his bed, his predatory eyes freely following the curves of her mostly-exposed body. His shirt was off and sure, he wasn't fat per se, and he certainly didn't have a beer gut like a lot of men his age, but he was far from the toned, muscular men she always imagined in her fantasies. Ugg... hairy and flabby. Disgusting.
He still wore his pants however, and although he didn't have a full-pitched tent, her eyes were drawn to a bulging shape. Well, he might not have the body of a pinup boy, but at least his cock was - Shut up! She was not going to let herself complete that train of thought.
Anna took a deep, steadying breath, then approached the bed.
***
Nigel felt his heart beating in his chest as the fit and curvy teenager climbed onto his king-sized bed and approached him on all fours, giving him a front-row view of her generous cleavage down the front of her bra. He wanted to rip it off her, to fully expose her full bosom but restrained. Why rush? He had plenty of time to enjoy her body tonight. Might as well savour every moment for what it was.
Besides, he was confident that he could outlast her at least once. Unknown to the young blonde woman, he'd deliberately finished himself off again not long before she'd arrived. While he was sure there was a good amount of sexual tension built up inside his luscious target, if she had in fact masturbated herself earlier to release her hunger... Well, he had no intention whatsoever of giving her up after tonight, so he was not going to risk blowing his load before she'd climaxed at least once herself.
And the fact was, she was truly exquisite, and even though he was well past the heyday of his twenties and thirties he would be driven to the brink just by having her slide his cock inside her incredibly tight and wet cunt. Throw in her own orgasm clamping down on him...
No, he had planned this night, this trap, and he would not let himself lose nil-to-one. One-all, yes. Preferably one-to-two, but not nil-to-one.
He smiled to himself as he noticed Anna's bright green eyes were fixed on only one thing: his parcel.
Oh yes, he thought, Whether you want to admit it or not, you do need it, don't you, slut?
Nigel lifted his hips as she tentatively tugged down the rim of his pants, and finally his cock sprung free. He groaned as his neighbour wrapped a hand around his waiting shaft, her soft skin warm on his cock. She stroked it absently, once, twice, then seemed to remember his instructions, and leaned forwards.
A shiver ran through Nigel's body as her moist tongue delicately licked his exposed ball-sack. Once. Twice. Then, still slowly stroking his shaft, the young woman opened her mouth and wetly kissed his jewels.
Oh hell yea...
He placed a hand on her head, feeling the silky blond hair under his fingers. For a moment he gently pressed down, and she instinctively opened her mouth wider to suck one of his balls fully into her wet mouth. He groaned again as her tongue traced over his nut.
Slowly he slid his hand down her neck then back, towards her perfectly round ass, feeling the softness of her skin. Sliding his hand underneath her panties, he slid a single digit down between her cheeks, not intending to give her a head start on arousing him. As his finger reached her waiting pussy, he froze.
"You're already wet," he said, surprised. Now that was entirely unexpected! He'd seen her deep sexual need, but to have her already wet under these circumstances...
***
What? Surely not... Anna thought at Nigel's statement, but here was no denying the excited tingles that had exploded at his brief touch.
A shiver ran up her spine as Nigel slid his thick finger between her pussy lobes. There was no hiding the telling slickness. Wet before he'd even touched her...
Fuck. You're such a... such a... she couldn't finish the thought, despite the fact that her mouth was filled by a repulsive saggy ball-sack as the man she hated toyed with her pussy.
On the plus side, if she was already wet then that meant she could take that disgusting thing out of her mouth. As spat out the heavy sack, Nigel deftly honed his attention to her clit and she gasped. Hell, she'd better get started with her main task, otherwise she risked being brought right to the brink of her own orgasm before she'd even had a chance to finish him off.
Anna looked up at Nigel and held his gaze, trying to draw his attention elsewhere as she shifted her ass out of his reach. Those eyes... they were ice cold and merciless, yet at the same time they burned hot with desire. That hunger, she felt it leaching into her, causing her heart to race excitedly.
Stay focused, she cautioned herself. Don't get distracted.
Just stick to the task.
One hand still stroking the thick, veiny cock, she used the other to slide her panties over her bum and down her legs. A shiver ran through her body as her moist pussy became exposed to the coolness of the air-conditioned room, and a horrifying thought suddenly occurred to her. She was giving that blasted camera a perfect rear-end view of her completely uncovered and clearly wet vagina, and she'd even given a her ass a wiggle as she'd pulled them off. Ah shit.
She simply had to ensure that Nigel came first. That was the only way she could keep that horrifyingly shameful video from his grasp. She had no choice. She needed to win.
As long as he kept his word.
Firmly pushing the camera out of her mind, Anna crawled forwards and swung one leg over Nigel's hips. With one knee on the bed at her neighbour's waist and the opposite foot in an equivalent position on the other side she could feel herself being stretched open in preparation. The 53-year-old man's eyes were now hungrily focused on her pink vagina as it hovered inches above his thick cock. Anna herself fought the urge to look down, knowing full well that the sight of that angry rod waiting would just send her into a tailspin of exhilaration.
As Nigel had pointed out earlier, she had two - and only two - advantages here, and she needed to use them if she were to have any hope of success. Firstly, her body: she knew she was hot, and she needed to use that to drive him wild. And secondly, she was in control.
So, for a few moments Anna remained poised in that position while she continued pumping his hard cock as fast as she could. Give him a nice, juicy view, let him drink in the sight of her, build his anticipation of what was about to happen... all to send his excitement as high as she could before she really got started.
She just needed to keep focused on not caving in to her own pent up cravings. She tried conjuring up a series of thoughts to suppress her arousal: He was so old. He's ugly. He's disgustingly hairy. His cock is too big. It wouldn't fit. It would force its way into her, stretching her wide, giving her the best - no force that thought away. He was a sick pervert. He was taking advantage of her. He was using her and it turned her on like never - no no ignore that part. He was old. He was...
