The girl's thoughts seemed to confirm 263's assumption that it was in the clear. The monster woman appearing here didn't seem likely, and most other monsters, it would be willing to fight to stake its claim. If another student were to show up, 263 would be able to just drag the interloper into a corner and rape her too while it finished this game with Rhaine. And if too many students approached for it to handle, it would probably just cut its losses and pull Rhaine into the vents, having fun with her there for a while.

For the time being, though, 263 was perfectly happy to continue the game as was, especially since the girl didn't seem to be doing all that well. Things certainly weren't about to get easier for her, either. Immediately, the tentacles around her torso moved to her bra-clad breasts, circling around them and starting to squeeze. Two tentacles raised their tips to each of her tits, pressing against her bra cups and indenting her breasts in on themselves. It could feel her stiff nipples even through the protective cloth, further evidence of her growing excitement.

The monster wasn't content with her chest, though. Around her legs, the tentacles had traveled all the way up the length of her thighs. Two of them uncoiled from her legs, and slid up, passing under her skirt. Underneath her clothing, they pressed against her mound, gently stroking her sex through her panties. One of the creatures eyes floated under the desk, staring up her skirt and enjoying the view of her moist panties as its tendrils went to work pleasuring her.

"Pleasure. Keeps. You. From. Focusing," it observed. "I. Wonder. If. You'll. Be. Able. To. Finish. Like. This." It teased her as it continued to stroke her chin, and another tentacle brushed across her lips.

Her bra was little protection as he poked at her nipples causing them to indent. Other tentacles continued to work all over her further distracting her. Soft pants as he played with her chin which felt no different then any other student's. Yet their was something about it that she could not explain, either something new that she did not know about or a reaction of some sort. In the future she would find out though that had not been the only place he directed those tentacles.

They rubbed against her, almost demanding her attention.

Her panties, a matching yellow coloration, had displayed a damp patch even before the additional touches from the pair of tentacles that dipped beneath her skirt.

“Oh … ahh ...” Next puzzle. Next. Next. Each on harder to complete then the last. Some of the magazines had a couple of puzzles in them too some just had two, that week's and the answer to the week before.

When she opened the newspaper there was the Sudoku puzzle, a challenge with all those tentacles upon her but then she paused hit by a bit of dread. A crossword puzzle. She hated them, not only weren't they math problems but her grasp of words had been inferior. That and she always had to skip around and needed more concentration.

She was afraid. She couldn't complete this! And even if he had there were others. Fear motivated her to try. She tried to shut off everything else but failed to do so.

“No ...” she finally answered him with a whimper to that word.. Seven across … skip it, Nine across … skip it too … Ten across was time which made seven down teddy given that she had the T now and had several others from other words.

But he had never set a time limit in which she had to finish by she just realized, her eyes widened at that then she attempted to relax, her pencil quaking in her hand. The next question, it should have been an easy one, the name of the baby on the Simpsons and yet why was she having trouble with it now? Six letters. Thelma … no that was one of Marge's sisters if memory served. She was quickly becoming unhinged ...

263 enjoyed watching her squirm as she struggled to stay focused. It could tell she was having a particularly hard time with one of the puzzles, and that there were many stages to work through it, all of which gave her trouble. It was really quite perfect. Here, it had been worried that thirty puzzles would be too few, and let her off the hook too quickly. It seemed to be just right, though, especially given how hard it was becoming for her to focus.

Not that it was going to make it any easier on her, of course. In fact, this was the part where things were going to get interesting. One of the tentacles hooked into her bra, yanking it up and letting her naked tits bounce back down. Its eyes stared eagerly at her chest, and several of its tentacles gave her breasts a soft caress. However, the mass of tendrils didn't fall upon her chest as they normally would. Instead, one each circled the base of her breasts, holding them up to prominence, as two new tentacles emerged from behind her. Unlike the others, the ends of these tentacles were concave, and quite narrow. They snaked up in front of her breasts, and fitted themselves over her nipples like suction cups. Seconds later, they began to do exactly that. They sucked against her breasts firmly, pulling on them as they held her nipples captive.

Down below, the tentacles were getting even more eager. After a few moments of petting the girl through her underwear, one of the tentacles looped through the crotch of the garment, pulling it aside to expose her naked, wet sex. 263's eye stared at it approvingly. "You. Have. An. Enticing. Pussy," it told her, as its tentacles began to grope it. One of them began to slide its shaft between her lips, grinding against her. Another, much more slender tentacle wrapped around her clit, massaging it.

Her bra was pulled up and he used tentacles she had not seen before where hey slipped over her hard nipples. He suctioned on them and while she felt similar effects before there was no mistaken that it felt nice.

“OHHHHHH!!!” A long drawn out moan. She squirmed and whimpered, her body heating up against those touches. “M-M-MAGGIE!” The answer to her latest question hit her and she jotted it down with a shaky hand. But now her panties had been pulled aside and she was touched. Her nethers rather heated, excited, her breathing increasing, the pencil falling to the floor though fortunately their were others within easy reach.

Her clit was on fire with those strokes as it moved against her. A tentacle rubbing between her puffy pussy lips. He was so close to taking her and yet so far. Being taken again was inevitable but how was the bigger question here.

“I ...” She gasped and clamped down a moan, his response from before had not been favorable and there was no choice but to continue as best as she could though it was shaping up to be a long night ...

263 watched the girl squirm in delight. She seemed to be enjoying herself almost as much as it was enjoying her. Her tender erogenous zones were making short work of her, constantly stimulated and teased, and it could feel the answers to questions coming slowly, having to burst through the fog in her mind. There was a very simple reason it hadn't given her a time limit for this trial: she was welcome to complete the puzzles any time she wanted. And if being fucked in the mean time proved too much of a distraction to allow that, that was on her.

And 263 would fuck her, but not just yet. It wasn't done building its own anticipation. Next came her lower clothes. Tentacles writhed around her waist suddenly, gripping at her skirt. With a few quick tugs, it met the same fate as her blouse, scraps flying and fluttering away as it was rent, leaving only scraps clinging to her waist. Her panties came next, tentacles seizing the waistband and yanking it down and out. More tearing noises echoed as the garment was puled completely apart, peeled from her body where it was doing little good to begin with.

With her lower body now even more naked, more tentacles began to swarm her crotch, rubbing against her vulva, while some even slid towards her ass. Still, none of them entered her. In fact, the one that had been grinding against her even withdrew. It was soon replaced by another, though. And as this one pressed her lips, it began to vibrate. The tentacle hummed against her slit, sending tremors in waves through her body.

Naked save for her shirt and bra Rhaine had been made to sit there and endure it. Her blouse had been torn open and problem solving had slowed to a crawl. Even the easy questions where harder though he had to be aware of that with the applied suction on her breasts which had been but one of the reasons she had been panting.

She had been half way trough reading the next clue when she cried out, those vibrations starting up against her clit just as it continued to massage her lips and other areas of her face.

Tentacles switched off as if one tired and needed a breather. Replaced by another tentacles even crept t her backside, deep breaths had her mouth opening further, the tentacle against her lips would have easier access now. Crimson eyes closed briefly trying to toss off all this pleasure, to refocus on the problems.

It seemed to work for the next two questions before the third tripped her up or was that his touch?

“Yes ...” she gasped, falling beneath the waves against so much pleasure as he did the reverse of last time bestowing pleasure in lieu of that pain, in either case she would have been overwhelmed by either.

The vibrating tentacle pressed deeper into her hole, not quite far enough to be considered fucking her, but deep enough to send the vibrations crashing through her inner walls. It started to move the tentacle in a slow circle, radiating pressure to all sides as it sensed her begging for more. She was moaning and gasping now, her body showing clear approval for its ministrations, even though the girl herself was still trying to solve the problems to escape her predicament. As futile as that was, it was probably wise of her. 263 had her in a world of pleasure right now, but once it got serious with her, it would tire her out very quickly.

"Can. You. Even. Leave. Naked. As. You. Are?" it taunted her, as its eyes drank in the state of undress it had reduced her to. "What. If. Someone. Sees. You?" The creature didn't know how bashful the girl was about her body. For some, even the threat of repeated rape at its tentacles wasn't enough to fully overcome anxiety over public indecency. And if she were trapped here by her nudity, it wouldn't go easy on her.

For the moment, it would have its own fun, however. The girl's mouth hung slack as she moaned and panted in pleasure. That was a great opportunity, although the tentacle that brushed her lips right now was much too slender for its taste in oral rape. It slithered away, only to be replaced a moment later by one of the much thicker ones, its bulbous head pushing into her mouth immediately. Without hesitation, it headed for her throat. 263 did its best to keep from blocking her view of the puzzles - fair was fair after all - but it wasn't about to slow down in claiming her mouth just for her convenience.

She was confused. Had he been asking a question he expected an answer to? It crept past the veil of pleasure. “Yes ...” she gasped again in answer and in pleasure at the same time. She wouldn't like it bu had been chased through the jungle while naked. It had been her past experiences though, the envisioning of broken bones and pain that had not been matched to anything else on the island.

To avoid the same matter she would live with a bit of embarrassment. But that shifted too in her mind, if she didn't have it so bad she would endure and attempt to do something with the torn clothes to cover her until she could get to others. She didn't like it but if she had to choose between the two embarrassment beat pain.

Yet this time there was no pain … at least not yet. She was afraid that there would be, that there was some sort of cut off point where puzzle time would be over and that was what caused her to try so diligently now. He pushed into her mouth with one of those thicker tentacles. It was even pressing against her nether lips more and she could feel the vibrations rip though her.

The second question was something that was tougher to answer. She didn't know. If she were seen like this by another student she supposed she would be alright depending on the context. During was one thing since the other was likely forced to join in but if discovered afterward once he had left her in a pool of her juices and blood she could not say. “I … ohhh … don't know.”

“Mmm …. ahhh ...” the sounds muffled against the tentacle pressing into her mouth and while her view of the puzzles had not been hinder to much her problem solving all but stopped as she found it even harder to concentrate with these additions to her own pleasure. Once more she could feel her own arousal building as she squirmed beneath the humming touch against her clit and the tentacle grinding against her as others assailed other regions, her tits tingling as that suction went to work on them further drawing her young body closer to release.

The fear of pain was still there in the girl's mind. Her memories of what 263 had done to her last time were still stark in her mind, and though there was no pain in the bargain for her yet, the risk of it would compel her to endure substantial humiliation. Were it not an ironclad rule that it never be found out, 263 would have been tempted to show her off to some of her peers just for asserting that.

Instead, it would have to amuse itself with her body for a while. It could feel her climax building even without reading her mind, and that building pleasure had nearly brought her problem solving capabilities to nil. Just a little bit more, and it seemed like she would be too busy cumming her brains out to worry about math or words.

"Isn't. Solving. Puzzles. Like. This. More. Fun?" it teased her as the coils around the base of her breasts began to squeeze more firmly. The suction cups began to move away from her body, pulling her tits with her. Their suction began to pulse, alternating breasts as it grew stronger, then weaker, then stronger again. Meanwhile, the vibrator moved up, away from her hole to focus entirely on her clit. It pushed its humming shaft against her pleasure button, diverting every vibration into it. Meanwhile, another tentacle raised its head to wiggle against her briefly vacated lips. Its intent seemed quite clear - it was only a matter of time.

Her breasts ached in an all so good way as those suction cups pulled stretching out her nipples as the vibration had been pressed more to her clit the full force causing her to press down with her pencil at the same time snapping the tip leaving her with but one pencil left …

A low moan followed, she did not know if that had been meant as a rhetorical question or not though it was clear that she was in more pleasure now then she had been before though she had been more focused then now. Her breathing was quick and shallow, her vacant passage trembled and clenched as she had been pressed closer to that edge.

“Ohh ...” she had her fingers on her last pencil when the orgasm hit, quite powerful spreading outward from her gut. She felt it everywhere, that explosion that felt so good and yet as her mouth was taken once more her eyes widened not at the action but at the sight of her final pencil rolling off the desk hitting the floor and bouncing a few times though it rolled some place out of sight beneath the desk itself she had been unable to see if the lead broke off from the tip.

It was over, she couldn't finish the puzzles now even attempting to hold answers in her head she couldn't keep more than a few of them there, right? As alarmed as she was another orgasm hit as powerful as the first.

“Plmphumph!” She tried to utter a single word, couldn't utter it clearly though it was over again and her mind was turning to last time rather than the price of spending the remainder of the evening in it's clutches.

The tentacle between her legs thrust itself into her pussy even as she reached for her final pencil. It entered her with a powerful force, filling her up all the way to her cervix in one steady movement. If 263 had a habit of making noises, it would have groaned at finally allowing itself to enter her. As it was, its other tentacles began to squirm in excitement, partially from fucking her, and partially from the sounds she was making.

As her pencil rolled away from her, and her last hopes of escape with it, the tentacle began to move. In and out, in and out it stroked steadily, shoving firmly against her tight passage as it felt her squeeze around its girth. Its movements weren't as unrestrained and animalistic as they had been last itme - not yet, anyway. Its vibrating tentacle remained near her clit, wet with her juices, and began to slide back and forth against the sensitive button.

More eyes appeared from her periphery, watching her beautiful form be fucked helplessly in her seat. One of its eyes even saw where her pencil rolled off to, and it briefly contemplated retrieving it and letting her continue. Ultimately, it decided such mercy was counter productive. However, every tentacle restraining her to the chair uncoiled, leaving her essentially unbound.

"Retrieve. Your. Pencil. If. You. Can." It taunted her. "You. May. Continue."

She sat straight up, eyes widen at the sudden thrust into her that produced a long muffled wail of pleasure against the tentacle filling her mouth. It was deep, her body folded around it as others played with the remainder of her body even now. But he wasn't as savage this time.

He even freed her to an extent though that tentacle pressed into her. More eyes came into view, watching her, delighting in her no doubt. But others drew away freeing her from that seat.

He taunted her, though pencil or not she knew she couldn't finish. With the flat of her palm on the top of the table she had been seated at she bent forward practically setting her face on the surface as she groped with her other hand for the pencil, almost as if she had been unaware that he freed her from that seat in the first place.

Hearing the juices of her body with each of his thrusts he remained on target. Fully lodged inside her each time her special places were ignited with each thrust. Continuing her moans against the tentacle in her mouth she felt her finger tips graze the pencil … then it rolled …

The chair slide back and soon she was on her knees dipping her head beneath the table, stretching and grasping the pencil. Good, it wasn't broken but she was in a bad spot she knew. Unable to vocalize though she attempted a different tract.

Rhaine knew she had lost but she would continue to try but she thought she might be able to shift his attention from hurting her too much or just make him eager to do so once his fun had waned.

Her tongue began to slide against that invader swirling around it, caressing it as she retook her seat trying to focus on the puzzle where she left off but finding it harder to do as a wave of pleasure was growing larger and larger the closer it got like a tsunami ringing forth an incredible wall of water.

The tentacle inside her picked up speed and force, starting to fuck her even more thoroughly as 263 allowed her to try and retrieve her pencil. It didn't slow for a second, even as she reached for the floor, and in a fit of sadistic lust, thrust hard into her as she leaned down, nearly knocking her out of her chair. It kept fucking her like this, holding her at an angle. It liked having her off balance, the constant threat of gravity sending her toppling to the floor, pinned to her side and unable to recover for the rampaging shaft inside her.

The girl ended up on the floor anyway, crawling for her pencil. And still the tentacle thrust into her as she tried to retrieve it, every thrust threatening to shove her forward and knock her down, holding her there while the beast had its fun with her for the rest of the night. This allowance to retrieve it seemed more and more like a trap with every passing second.

Yet she returned to her seat, but the constant fucking didn't end. Both tentacles thrust into her relentlessly, pounding the spit roasted girl and leaving her body working against her mind. One of the tentacles even lifted her leg, forcing her hips to spread so she could be fucked more easily, and more deeply. Her tongues movements against the tentacle seemed to please the beast, but it made no indication of going easier on her, or changing any plans it may have had for her.

It had almost been as challenging retrieving the pencil and returning to her seat then the puzzles had been themselves. Kept off balance he was getting eager now hinting at that day at the sport's field as those tentacles drove into her deep and hard. Her leg moved to the side though the thrusting had not eased up.

And yet she knew that he could be far rougher too and that frightened her. Those thrusts though made it impossible to concentrate on what she was doing. She had read the same question three times but the clue just wasn't sinking in.

What was had been that tentacle pressing into her reaping that next release from her that had built up so much already. Her hands balling up into firsts, eyes wide she struggled to breath through her nose, struggled to read the question but still it was no good. Constant stimulus getting the better of he and the rougher approach mixed in was too distracting to keep focused on thing.

She was stuck there, held to that chair and now that price was to be paid as he shattered what remained of her focus with the combination of sensations entwined with those growing thrusts both eager and deep as she was made to stretch out about him.

263 could sense that the girl didn't really have anything left in her. Allowing her to continue at this point would mostly be a formality, and it was far more interested in what it could do to her than token rules. It had all night to rape her again and again, and it wasn't going to waste half of it pretending to wait for her to get her act together.

A tentacle wrapped around her other leg, lifting it and spreading it just as the other had been. her legs were now opened wide, her knees nearly lifted up to her stomach. This left her rear pressed against the chair, and her pussy exposed and spread, which the tentacle inside her quickly took advantage of. It thrust in to her hard, rocking her entire abdomen with every impact into her sweet young pussy.

As she was held open to be fucked, the tentacle inside her mouth reached its climax. It thrust deep into her throat, squirming as it begun to pulse, and spewed globs of warm, bitter goo down into her stomach. The tentacle pumped as much into her as it could, before finally withdrawing, leaving her mouth open.

"A. New. Puzzle. For. You," the creature stirred inside her head, recalling one of the configuration puzzles it had seen in her mind.. "How. Many. Ways. Can. You. Be. Fucked. In. One. Night?" It moaned in sadistic delight as it continued to fuck her roughly. It had no plans to injure her this time, but it would make very sure her body felt this for a while to come.