Jack and Phoebe Ch. 02

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Jack and Phoebe's week continues as does Tom's suffering.
8.6k words
4.82
4.7k
2

Part 2 of the 14 part series

Updated 06/11/2023
Created 06/25/2022
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Author's note: There are absolutely no characters under the age of 18. All sexual acts take place between adults over the age of 18 years.

Jack and Phoebe 2

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"Pip Pip Pip, Good morning, it is seven am on Tuesday the 19th of September, and you're listening to BBC Radio Four, the headlines today are."

Jack's hand came crashing down on the radio, which gave its little plasticky squeak of complaint as it shut off. He rolled onto his back and stretched out, enjoying the warmth of his bed and thinking back to the previous day's activities with Phoebe. His cock, already hard, grew even harder and without thinking his hand drifted down and began stroking himself. He kicked off his duvet, and lying naked on his bed stroking himself, he closed his eyes as he tried to recall how Phoebe looked and felt yesterday. His stroking became more frenzied as he approached climax, and soon he was overwhelmed as he reached orgasm, his abdomen tensing up, his back arching and his cum cascading down onto his stomach and chest in several voluminous gouts. He released himself, and breathing hard opened his eyes and looked at the mess he made of himself. For a second, he felt rather proud of the size and quality of his emission, that is until he noticed that his bedroom door was slightly open and he was sure it was shut before he started his morning activities. He felt embarrassed that someone had caught him having a wank, until the thought crossed his mind that someone might have actually watched him having a wank. Someone watching him would be a different matter to just being caught, but he had to admit that he found that notion a little titillating. He reached under his bed and grabbed an old t-shirt and used it to clean himself up, and then started his morning routine.

Maggie had just come out of the bathroom, towel wrapped tightly around herself when she heard her mother shout up the stairs for Jack to get up. Without thinking she walked to his door and opened it, intending to pass on her mother's wake up call. She stuck her head round the door and was confronted with the sight of her brother, completely naked on his bed, vigorously stroking his hard penis with his eyes screwed tightly shut.

The right thing to do would have been to quietly close the door, back away and never mention this again. Maggie knew the right thing to do, but she found herself rooted to the spot and her hand wandered beneath her towel and between her legs. She watched as Jack's muscles flexed and strained, she saw how hard he was, and how slick his dick had become as he sped up his strokes. She found herself contemplating what it would be like if she joined him on the bed, and this thought caused her fingers to circle her clitoris with just a little bit more fervour. As Jack's cock erupted, sending great spurts of white crashing onto his chest and stomach, she was shaken out of her fugue. Catching herself, she suddenly realised what she had been doing and that it was not acceptable behaviour for a sister to watch, let alone, to enjoy watching her brother in such activities. She carefully backed away and went into her bedroom and it was only after she had closed her door and collapsed onto her bed, that she remembered that she had left Jack's door open. She felt a combination of shame and arousal, half of her wanting to curl up into a ball and cry with guilt, whilst the other half screamed out for her to finish what she had started in Jack's doorway. She opened her bedside table drawer and reached inside for her little bullet vibrator, but her eyes caught her clock and she realised that she did not have time this morning. Her punishment for her filthy, incestuous thoughts was going to be her frustration throughout the day.

Jack left for school, toast in hand, the thought of being caught this morning still fresh in his mind. He got on the bus and for the fifteen minute journey tried to put it out of his mind, drowning his thoughts with the final five minutes of his favourite football podcast and some loud music. He arrived at Phoebe's and pushed the doorbell, wondering whether he was in for a treat like yesterday, his body beginning to prepare itself for her. He was, however, to be bitterly disappointed as Phoebe's mum answered the door.

"Hello, Jack," she greeted him with a big smile and turned her head to face into the house, "Phoebe, Jack's here!" she shouted.

"Hi Dr Harrington, how are you?" he asked politely.

"I'm fine Jack," she replied, "it's good to see you, with my shifts I've not seen you for ages! Come in, I'm sure Phoebe will be down soon."

Just as she finished speaking Phoebe appeared from behind her and pushed past. With a quick wave to her mother, Phoebe marched Jack down the garden path and out the gate.

"I'm sorry, we can't start the day like we did yesterday, but it was a full house this morning," she whispered, her bottom lip sticking out accenting her comedy frown.

Jack smiled and gave her a peck on the cheek.

"It's not a treat if you have it all the time!" he replied.

"That's very true, but it is looking like we won't be getting up to any fun at my house for the next few days. Mum and Dad are going to be home in the mornings and Mum has a few days off because she worked those lates last week," she said, a little disappointed.

"We might be able to have some fun round at mine, after school," he suggested, "Maggie might be home but she'll turn a blind eye if we keep it confined to my room."

He glanced at Phoebe, wondering if she would go for it.

"Let me think about it, I'll have to ask one of the girls to cover for me," she paused, "I can't very well tell Mum I'm going round to yours after school, she'll instantly know we're shagging."

She giggled at the thought, and slipped her hand into Jack's trouser pocket and gave him a little stroke, and got an instant response.

"Phebes, please don't!" he implored, "we're almost at school and now I've got to think about Mrs Bouchet naked to make it go down!"

Phoebe laughed and leaned up on tip-toes and gave him a kiss on the cheek.

Just as yesterday, when they arrived at school, they split up and found their respective group of friends. Mike and Dan were standing over by the fence on the far side of the playground, as usual, so Jack headed over.

"No Tom?" he asked the pair, looking around for his missing friend.

"Haven't seen him since afternoon reg yesterday," replied Dan, "I tried texting him last night, but he didn't reply, which isn't like him."

"I tried calling him, but it was going straight to voicemail," replied Mike, "I'm at a loss, I hope he's okay."

Tom was back in the disused classroom where his ordeal began yesterday. His head was buried between Jasmine's legs as she sat in one of the old chairs at the back of the room. They were arranged so that no one entering would see anything with Jasmine sitting down, Tom, under the desk, would be completely hidden. Aria was sitting on a desk watching over the scene, her hand between her thighs lightly playing with herself.

"Hurry up, Tommy, I want to have some fun too." Aria demanded.

Tom briefly wormed his tongue as far into Jasmine as he could, he then brought two fingers up to her and after getting them wet with her moisture, slipped them both inside and felt for that special patch just inside. He concentrated his tongue on her clitoris and started rubbing on that spot.

Jasmine grasped the edges of the desk in front of her.

"Oh, fuck, oh shit," she gasped, "I'm going to cum, don't fucking stop!"

Tom, wanting this to end, wetted the index finger of his left hand as best he could with his saliva and her juices. He pressed hard on her G-spot with his right hand, and shoved his left index finger hard against her anus. Taken completely by surprise, just as her rosebud relaxed for a second, the finger speared straight through both sphincters and all the way to the third knuckle. Jasmine almost launched herself into orbit, the penetration of her arse sent her over the edge and forced her to come hard. She made a sound that was whale-like, keening and completely unintelligible, her head crashed onto the desk and her body twitched.

Tom climbed out from where he was as Aria stared at Jasmine, still playing with herself.

"My turn," Aria commanded, "but I'll give you a choice."

She gave Jasmine a final look and then brought her bag up onto the desk beside her. She reached into her bag and extracted a black velvet bag, about the size of a paperback book.

"Here's your first choice," she began, "the contents of this bag and nothing else until tomorrow, or," she paused again for effect, "I get what she had, and then we go round to mine tonight for some more fun like yesterday. You have 5 seconds to decide."

She began to count down from five. Just as she got to one, Tom interrupted her.

"I choose the bag," he said, sure that it was going to be terrible but hoping that it would at least allow him an evening of freedom.

"Oh goody!" she exclaimed with an evil giggle.

She stood up and started manhandling Tom, she pushed him up against a desk and forced him to bend forwards at the waist. Tom acquiesced, not wishing to prolong his misery any longer than necessary. Once his head was on the desk, she reached round to his front and undid his belt, button and zip. She tugged his trousers and boxers down, leaving him naked from the waist down. Next, she kicked his feet apart forcing him to widen his stance.

"I want you to remember my next act as one of kindness, remember that I'm doing this because I want to and not because I have to." she stated, leaving Tom a little confused.

The next thing Tom felt was something cold,wet and slippery drip into the crack of his arse, and then a pair of fingers sweep the length of his crack, home in on his anus and push straight into him. His head shot up, and he balled his fists and tried to buck Aria off and out of him, but he was not able to. Aria had pushed two fingers, thankfully greased with lube, completely into him right to the third knuckle. His anus clenched and relaxed in an erratic rhythm, but she forcefully stroked in and out, pushing sideways, up and down, and started stretching him out.

"In a moment, you're going to thank me for this," she said.

Jasmine had recovered her senses and was taking great delight in Tom's discomfort, she was finding his pained expression quite arousing, soon her hand drifted down between her legs.

Tom's face was bright red as he realised he was starting to enjoy being treated this way, he was fully erect and leaking pre-cum all over the desk, he was fairly sure he would cum from Aria's fingering if she hit his prostate a bit more frequently. He struggled to contain his groans, he really did not want Aria knowing he was not just not suffering, but actually beginning to enjoy himself.

After a few minutes of pumping her two fingers in and out of him, Aria was satisfied that he was opened up enough. With her free hand she reached for the cloth bag and extracted a weird t-shaped plastic object, it had two bulbous heads on short, thin, but stiff, stalks. She pulled her fingers out of Tom, wiped the lube over one of the bulbs on the object and pressed it to Tom's ring. The lube and preparation made it almost painless, as it slipped into Tom without too much effort or discomfort. Once it was in place, Aria gave it a little tug to check it was in properly and secure and then she pulled up his boxers and trousers.

"Right, stand up and straighten your clothes out," she ordered, "all you have to do today is leave that inside you until you get home. You can take it out and clean it when you get home, and I want it back tomorrow."

Tom was confused again, it was not comfortable, but it was hardly tortuous. His erection had begun to subside and he started to walk towards the classroom door to leave.

"Oh just one more thing," said Aria, causing Tom to turn round to look at her.

She had a small black object in her right hand, her thumb on the top.

"This," she said, pausing to wave the object in front of Tom's face, "this is the remote control."

She pressed a button on the object, the remote control, and immediately Tom's legs gave out from under him causing him to fall to the floor, his back arched. The object inside him had begun to vibrate directly on his prostate and perineum, stimulating both and sending waves of pleasure throughout his body. Tom lay on the floor, gasping for breath, on the edge of cumming, when the vibrations stopped.

"Did little Tommy enjoy that?" asked Aria.

Jasmine giggled behind them both.

"That was level 5 of 6. Oh yes, it goes one higher, let that sink in for a moment," she smiled that cold cruel smile as the ramifications of his predicament sunk into Tom's brain, "I think you'll find today's lessons quite interesting. Oh and don't think you can go to the toilet and take it out, if you do a little indicator will let me know, and I will make your punishment for disobeying me, fucking delightful for me and horrific for you. Now, off you fuck to class, you don't want to be late."

Tom hauled himself up, and after a moment straightening out his shirt, he walked quickly out of the classroom.

"You really going to make him cum in the middle of class, then?" asked Jasmine.

"Probably not, just going to make him squirm and think that I will. Remember, there's a long game here and little Tommy is just the first step, that bitch Phoebe is the prize, Tommy just gets us a little closer." replied Aria.

"What are you going to do to him tomorrow?"

"I think tomorrow, we'll save our fun until after school, and you're more than welcome to join in for that." Aria said, her evil grin spread from ear to ear.

Jasmine found herself equally aroused and terrified as she realised that should she ever fall out of favour she might end up on the receiving end of this treatment. She resolved there and then to never let that happen.

Jack, Mike and Dan were sitting at their desks in the form room when Tom walked in. Jack noticed Tom limping slightly.

"Have you hurt yourself?" Jack asked as Tom sat down rather gingerly.

"Err, yeah. Slipped in the shower last night and banged my hip," Tom paused, feeling rather pleased with his ad libbed excuse, "should be okay in a day or two."

"Where'd you disappear off to yesterday then?" asked Dan quietly.

"Oh, I had a dentist appointment after school, and was worried about it all day." Tom replied, again rather pleased with himself for his quick thinking, "turns out there was nothing to be worried about, no fillings needed!".

Tom was starting to feel more like himself, he obviously had the plug in his butt and it was hard to ignore, but his worries seemed to lessen with a little normal banter with his friends. Tom looked at the classroom door and his mood dropped immediately, stood there, face pressed to the glass was Aria. She knocked and entered, he could see the remote in her hand. She walked towards Mr Smythe's desk, and just as she bent down to speak with the teacher she thumbed the button on the remote. Despite being prepared, the vibrations whilst seated were extremely hard to ignore, they were at a much lower level than before, but, it was still enough to cause Tom to instantly become erect and unable to concentrate on anything but the sensations in his groin. He put his head in his hands and rested his elbows on the desk and tried to get through this.

"What's the matter, Tom?" asked Mike, putting his hand on his friend's shoulder, "You okay?"

"I'm fine, twinge in my hip," Tom managed to croak out as he hoped Aria would take pity on him.

Tom looked through his fingers to where Aria was still talking to Mr Smythe, bent slightly at the waist, showing off a little bit of leg for the rest of the class. He saw her thumb toy with the button on the remote again, and as suddenly as the vibrations started they ceased. He breathed a sigh of relief and tried to calm down and collect himself. Aria, meanwhile, turned to look directly at him, and then strode out of the classroom looking very pleased with herself.

"Ahh, that's better," Tom stated quietly, "hip's stopped twinging."

As the other three turned back to their books, Tom, as casually as possible, attempted to wipe away the small wet spot on his leg that had formed from his leaking pre-cum. He was starting to worry that maybe the cloth bag was not the right choice after all and he would have been better off with another evening at Aria's house, no matter what she made him do there. He was really hoping that she did not make him cum in front of everyone, but the thought of doing it was beginning to excite him, he really could not win.

Phoebe was sitting with her friends, Stephanie and Sally, in their form room and all three of them were catching up on some reading in silence. Phoebe had her politics textbook open on the desk in front of her and her head in her hands, as she read about proportional representation for the third time. She was stuck trying to memorise the differences, benefits and drawbacks of the various voting systems when she felt something gently touch her thigh. Trying to be as subtle as possible, she looked down at her lap and saw Stephanie's hand there just like yesterday. Phoebe was conflicted, she loved Jack, but she had always had some feelings towards Stephanie. She placed her hand on top of Stephanie's, and wondered what she was going to do.

Tom walked into his English lesson, and lost deep in his thoughts, made his way to his desk on autopilot. He snapped out of it when he found Aria in the seat next to his.

"Surprise, Little Tommy!" she whispered as her evil grin crept across her face, "didn't think you'd see me now, did you?"

"You're not even taking this subject!" he protested.

"Ah, you see, I have a free period right now, and I thought it would be interesting to see what other people are learning and Miss Knighting kindly agreed to let me sit in today. Wasn't that kind of her!" she mocked him with her sing-song tone.

"Please, Aria," he begged.

"If I were you, I'd hurry and sit down, you don't really want to be standing for this." she replied.

Tom just about managed to sit down and pull out his books and binder when the vibrations started. He'd been slightly prepared, and they were on one of the lowest settings like in the form room, but it was impossible for him to do anything with them stimulating his prostate and perineum. He rested his head on his hand and pretended to skim through his copy of An Inspector Calls, whilst his erection threatened to burst through his trousers and waves of pleasure travelled all the way up his spine. Aria was watching him closely, his discomfort was arousing her much more than she thought it would, and she now worried that she was building herself up for a whole day of frustration, and then she had an idea.

"I'll turn it off and leave you alone for the rest of this period, but you have to meet me in our classroom at lunchtime and don't be late." she whispered into his ear as she turned off the vibrations and stood up.

Tom nodded in agreement, the relief he felt visible on his face.

"I'm terribly sorry Miss Knighting, I think I've got to be somewhere else," she smiled obsequiously as she left the classroom, "so sorry."

Tom sighed loudly and slid down as far as his chair would allow him to.

Phoebe and Stephanie walked towards their history lesson.

"Stephanie, we need to talk," started Phoebe, "properly, in private and uninterrupted."

"I know," replied Stephanie, "I'm sorry, it won't happen again."

"I don't think that it is as simple as that, Steph," said Phoebe, "we need to work out what's going on and we can't have that discussion here. I'm free tomorrow evening, but we can't meet at mine."

"My parents are in tomorrow, but I could borrow the car and we could drive somewhere and talk." suggested Stephanie.