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Tim & Sara's Scheme - Part 2

"Tim and Sara, two hopelessly naive virgins, get together, scheming to get Miss Judy to punish them again."

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Author's Notes

"Part two of four of the Keep Those Grades Up series. <p> [ADVERT] </p>Enjoy!"

It had been more than a month since she’d seen Tim at Miss Judy’s, but she hadn’t seen him since despite keeping a keen eye out for him as she walked the campus to and from her classes. She didn’t have any idea what she would say to him if she did manage to find him but hoped that if nothing else, she’d find a kindred spirit with whom she could share these most secret desires. She had no close girlfriends with whom she shared any secrets, in fact, she had no good friends at school at all including her roommate, her only such friend back home whom she’d grown up with.

In the interest of getting to know more people at school, she attended a dorm party; something she’d avoided so far since she didn’t do well in large groups of people, especially those she hardly knew. She talked for a while with her roommate, probably more than they’d talked the entire school year so far, but it started getting strained and they separated to mix with the others.

Sara wandered around the large community room looking for friendly faces, classmates, and anybody who wasn’t a complete stranger and was having no luck. She was about to leave totally frustrated with the whole process when she spotted a familiar face sitting in a row of chairs in a remote corner. Is that Tim? It is!

She started walking his way cognizant of the effect seeing her would likely have on him. Within speaking distance, she slowed her eager pace noticing he seemed uncomfortable already, looking around the room as though he was lost and needed a lifeline. She approached cautiously but when just a few yards away he saw her and recognized her, he almost immediately got up to leave.

“Please don’t leave, Tim!?” she pleaded. “Please?” Still looking apprehensive, he stopped and seemed to look at Sara differently, taking more notice of her, maybe even interest.

Could it be any more embarrassing, he thought, to meet the person who’d seen him grab his cock after just having been spanked two hundred times over Miss Judy’s knee. The one person who may know his secret; that he loves getting spanked. ‘Maybe this is not a bad thing’ he thought to himself and that is what kept him from running.

A lifelong spanko, Tim had been spanked by his mother many times, an experience that was occasionally more than the punishment it was meant to be. He too was spanked when he’d gotten bad grades and as these were given with disappointment rather than anger, they had the potential to be somewhat pleasurable. The last two times before he left for college, he’d gone to the bathroom afterward to take care of his arousal. When his mother suggested the arrangement with Miss Judy, he had to consciously hide his excitement at the prospect of a professional giving him a spanking, a real spanking in his mind.

He had stood up when he was about to bolt and now remained standing as Sara approached. He noticed her subtle charm, what he’d once heard described as a girl-next-door look. She had a cute, friendly face with shoulder-length light brown hair. Her body was slim, but attractive again in a sort of innocent way, but when she turned a little his eyes fixed on her cute, round bottom, an obvious object of his desires given his love of spanking. He still found it difficult to make eye contact, given what she’d seen but he did look briefly into her green/gold eyes and motioned to a chair, inviting her to sit.

Sara could see how apprehensive he was and totally understood. She would have felt the same way had her roommate wandered in that first time she’d fingered her wet pussy to the memory of the paddling she’s just received leading to several orgasms. She decided she had to put his mind at ease as quickly as possible if they were to connect in any meaningful way.

“Tim? There’s no reason to be embarrassed,” she started in a voice just above a whisper, and, seeing his eyes questioning ‘why?’ she added, “I like it too! … getting spanked! I like it!”

“Really?” he asked, not believing her yet.

“Yes. Really,” she replied, but still seeing doubt in his eyes added, “When I left Miss Judy’s that day after getting the hairbrush, I went straight to my dorm room and … and, you know … touched myself till I came … several times!”

“You got the brush?” he asked as though it were something to be proud of.

“Yes, and oh-my-god it hurt! … down to the last swat! But it also felt so good after! I was so wet I was afraid Miss Judy might notice,” she confided. She saw him visibly relax and got a small smile as well.

“I just got spanked,” he said like it was nothing compared to her punishment. “I got a B on my essay, so I got …”

“Two hundred spanks,” Sara finished for him. “Over her knee, on your bare bottom!” she added as though the image of it was turning her on again. “I’m Sara, by the way,” she said realizing he didn’t know her name.

“Tim, but I guess you know that but how?”

“I walked in just as you were entering the room and heard Miss Judy welcome you.”

“So, you heard the whole …” he stopped, his eyes widening and embarrassment returning.

“… the whole spanking,” she finished for him again, “and it was so hot! I couldn’t stop listening and anticipating what I would get next! Tim, when you came out of the room and … you know … it made me realize that I could like it! … enjoy having my bottom spanked!” she admitted trying to set him at ease again, which seemed to work.

“Sara, I can’t believe you’re telling me this! Maybe we should go somewhere we can talk more freely?”

“I’d love to, Tim! A cup of coffee in the dining hall? It should be pretty empty at this time on a Friday.”

So, they left together and had several cups of coffee as they compared notes on their spanking experiences gradually getting more detailed in their stories. Though Sara had only recently discovered her interest while Tim seemed to have known his whole life, they decided their current interests were very much the same.

Over the following weeks, they met often and though they occasionally asked about classes and other school experiences, the topic of spanking monopolized their conversation. While they shared some very intimate details concerning spanking, it surprisingly never led to them doing anything more than kissing each other, and that was usually just when they’d meet or separate.

While they hadn’t discussed their sexual experiences yet, and truthfully there wasn’t much to discuss, they did conclude without saying as such that they were both very inexperienced and therefore rather naïve about sexual pleasures.

When it came to spanking, however, they were united in their lust and desire to get spanked again, both wanting that to happen as soon as possible. Whether it was just being such ‘good’ kids or the fact that they both wanted to be spanked, the thought of them spanking each other never entered the conversation, or even their minds. Instead, they started scheming for a way to get spanked again by Miss Judy.

Comparing notes, they shared their initial meetings with Miss Judy and how much emphasis was placed on them being adults and responsible enough to know when they needed to be punished and therefore should arrange for that to happen on their own based on the ‘honor system’. Realizing that they’d both had to tell her what assignment and grade had earned them their punishment, they concluded that Miss Judy didn’t actually know the specifics and relied on their honesty to determine first, that they needed to be punished and second, what kind of punishment it would be.

“So, what if we weren’t so honest about it,” Tim suggested.

“What do you mean,” she asked as though this was a totally foreign concept.

“Well, why couldn’t we make an appointment without having a bad grade?”

“So, we just make an appointment and tell Miss Judy about a fictitious assignment we’d gotten a bad grade on and … and get spanked!?” Such devious ideas never occurred to such well-behaved kids before and they both smiled at their newfound naughtiness. Going back to Sara’s dorm, they logged into Miss Judy’s system to make an appointment.

“Just spankings, okay? No hairbrush or paddle!” Sara suggested remembering the intense pain hairbrush spanking she’d gotten and the next would be fifty swats.

“Agreed and we’ll make the times together so we can listen in on each other and leave together!” Tim contributed.

“Good idea! I should go first though so you can listen to mine since I listened to yours last. Tim, I just thought of something. I’m gonna get two hundred and you’re gonna get three this time. If we do this again, it’ll be three for me and four for you!”

“Let’s worry about the next time later. By that time, we may want the hairbrush or paddle,” he reasoned.

Their appointments were made for the following day after classes, they then worked on what they would tell Miss Judy, what they would wear, and what they’d do afterward. Now they just had to wait, but it didn’t take long given how nervous they were about the whole scheme. Neither had done anything this deceptive and were having second thoughts, but as there was no way to cancel an appointment, they had to go through with it.

Arriving at Miss Judy’s, Sara went in first while Tim waited to hear her announced on the intercom after which he’d go in. They agreed to speak a little louder and clearer so the other could hear the dialog leading up to their punishment. A few minutes later he heard his cue and went in just in time to hear the beginning.

“Why are you here today, Sara?” Miss Judy asked, secretly delighted to have her favorite ‘little girl’ over her knee for another spanking. She preferred using her hand over the hairbrush Sara had gotten last time since she loved the feeling of having her firm, round bottom in her hands.

“I got a B on a pop quiz in American History. I guess I should know this stuff and I’m gonna get spanked, but that class is really boring, Miss Judy,” she confessed.

“Boring or not, Sara, you need good grades in all your classes to have the kind of overall average I know you want when your schooling is done. Now tell me how you should be punished.”

“Yes, Miss Judy. I got a B so it’s a spanking this time and it’s my third, so I get two hundred, right?” She was already wet when she entered the room, but she could feel her panties getting wetter, especially knowing that Tim was listening to every word.

“Correct. Get up and take your pants and panties down.” Having worn skirts previously Sara wore pants this time, wanting to feel what it was like to have her legs covered and her bottom the only exposed flesh. Judy took the seat Sara had been sitting in and patting her thigh said, “Come, over my knee.”

Sara expected the spanking to begin as soon as she was in position, but Judy was enjoying the feeling of her perfect bottom. The hesitation was noticeable, but not long, and, soon enough, she was squirming on Miss Judy’s lap, getting a painful but also pleasurable spanking. She also liked the feeling of a hand on her tender bottom but recognized the pain was different from the hairbrush; not better, just different.

Again, the thought of Tim just outside hearing the sound of her bottom being smacked along with her gasps and groans, was exciting and she played it up a bit for his benefit. She recognized the pattern of spanks as the same as her first spanking but doubled so twenty followed by forty and when she got to sixty, it was ten at a time on one cheek. The pain was getting intense but also giving her a similar numbing sensation as with the hairbrush, which allowed her to enjoy it a bit.

The next round of eighty meant twenty on each side which elicited genuine cries of pain, with thrilling internal feelings that went right to her crotch. She both wanted it to end and to go on much longer, but as the much harder final twenty on each side were crashing down on her sore buns the end nearing was a welcomed conclusion.

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“Oh, Miss Judy! That really hurt!” she said in genuine pain, but also to mask her feelings of having endured it while now getting the sexual satisfaction she craved. She couldn’t wait to get back to Tim.

“Good! Maybe it’ll have a longer-lasting effect this time! You can get up now,” Judy replied still enjoying Sara’s tight little body even as she pulled her panties and pants back up. As she reflected on the punishment just given, her memory was of the short, sudden glimpses of Sara’s pussy, a little wet with arousal she thought, and how she’d love to touch her there and make her come in her hand. She wished she could go to her bathroom and satisfy the lust that had made her panties quite moist, but she had another punishment immediately following this one so that would have to wait.

“Thank you for spanking me,” Sara said at the open door.

“Remember, keep those grades up!” she said as she always did, but secretly wished Sara would be back for more.

The door closed and Tim came out of nowhere to grab her and hug her as they both exclaimed how exciting that had been. Sara clearly knew now that despite the pain, she liked getting spanked and Tim experienced the excitement of hearing his friend getting spanked. Their embrace was short-lived.

“Come in, Mister Tim!” the intercom blared. They kissed quickly before Tim turned to go in, looking back briefly at Sara both with expectant smiles.

“Hello, Miss Judy,” Tim said trying to sound worried hopefully masking the excitement that had started building with the sound of Sara’s first spank.

“And what brings you here deserving punishment today?” Judy asked another of her favorite students. She’d seen the mile-wide streak of submission in him the first time she’d spanked him and suspected he enjoyed having his bottom spanked. It didn’t really matter to her as she had justification for the punishments she administered so why shouldn’t she enjoy them too? Sara had already made her panties wet and Tim would make them wetter still, but having two of her favorite students back-to-back was a mixed blessing because now she had to wait even longer to sate her hungry pussy.

“I got a B- on a term paper,” Tim confessed.

“Why?” she asked, simply wanting to shorten everything as much as possible.

“I left out one of the required elements for the paper. It was just an oversight … and now I’m going to get spanked again! Three hundred this time!” he exclaimed trying to sound like he was dreading it.

“I’m sure you’ll do better next time. Get up and take your pants down,” she said simply wanting to get quickly to the spanking which would surely saturate her panties and amplify the desire to get her fingers in her cunt.

Tim did as he was instructed and was soon over her knee with her hand slapping his bare cheeks much faster than he recalled. Before long he decided he liked it fast as there was less time between spanks for the pain to really set in, yet the speed had its own way of enhancing the sting though, rather like Novocain; it didn’t eliminate the pain, just postponed it until she gave him a rest. It grabbed his attention in such a way that he hadn’t thought about Sara listening until the break as well, and then, with the flames raging he remembered he had an audience.

“Oh my god, Miss Judy!” he exclaimed at the first break mostly for Sara’s benefit, but also acknowledging the different sort of pain he was feeling. She’d begun with fifteen in a row on one side, followed by the same on the other side, and then repeated for a total of sixty. He’d had sixty at a time before, but not at the beginning and not as fast as this.

“Hm, maybe I’m getting through to you this time, Tim?” she said sternly, though she enjoyed this new pattern she’d created as well. His body language which included growth between his legs as well as other tells, betrayed him letting her know he was in fact enjoying it to some degree and had the added benefit of stimulating her pussy even more to the point where she could imagine coming while still spanking him!

Her hands massaging his stinging bottom heightened the arousal brought on by the attack he’d just endured and felt so good that for the first time he imagined, wished that she could touch him in other exciting ways, possibly even making him come. So enthralled with these feelings was he that a pleasured moan escaped his lips, and realizing this she stepped up her massage, squeezed both cheeks hard, and then suddenly resumed spanking!

For the first time being spanked by Miss Judy, he had no idea of what was coming next. The pattern now was twenty on each side and repeated three times for a total of a hundred and twenty made Tim wonder whether he’d imagined the sensuous massage of his sore bottom, but this longer pattern brought the pain to the fore once more. By the time she’d reached twenty on one side, he was tucking his bottom in trying uselessly to avoid her spanking hand. Moving to the other side had the strange effect of giving the just-spanked cheek a rest, while his other cheek endured the next onslaught.

During what would be the last break her fingers wandered a little further than before, reaching and stroking the cleft between his bright red buns, moving these stray strokes gradually lower until they just missed touching his anus. He began to question Miss Judy’s motivation and wondered if he could enjoy her spankings, perhaps she did too?

She soothed his stinging cheeks to the point of him being fully hard and he was sure she could feel it pressing against her thigh. He’d almost completely forgotten about Sara listening without realizing that his genuine reactions to his punishment were far more exciting to Sara than him trying to make it more interesting.

When she resumed spanking, he had a feeling similar to Sara’s in that as the last round, it was harder and much more painful than before swearing silently, ‘Jesus Christ that hurts!’. But surprisingly, as he knew the end was near he was already thinking about how and when he’d get spanked again. Those thoughts were quickly forgotten as thirty intensely painful spanks built to an extraordinary crescendo before moving on to the other side, and, also like Sara, he was eventually glad it was over, especially after she’d unleashed some untapped energy to spank harder than ever for the last round of thirty on each cheek.

When she finally finished, he was draped over her lap like a wet towel, flaccid again and breathing erratically, Sara was trying unsuccessfully to avoid touching her pussy and Miss Judy was enjoying the feel of Tim’s warm, red bottom while holding back a climax until she could stuff several fingers in her dripping cunt in the privacy of her bedroom. All three got an amazing amount of stimulation from this spanking, though it wasn’t shared.

As they both had someplace, they wanted to be quick, they dispensed with most of the after-punishment comments and Tim pulled his pants up, his cock growing again and was out the door, with a distracted ‘Keep those grades up!’ from Miss Judy as she escaped to her bedroom before the door was even closed.

“Oh my god, Tim!” Sara cried as she jumped on him as soon as the door closed. She was speed-talking as she recounted each spicy element of his spanking while he was still in a kind of a daze, glad it was over but also savoring the fire in his pants at the same time.

“Tim?” she queried, realizing she’d monopolized the conversation and had not gotten any response from him yet. He looked up at her with a smile that said he was okay but still stunned by the experience. Sara smiled back and then biting her lip provocatively, slipped her hand into his pants much as he had done when they’d first ‘met’.

“Let’s go to my room,” she said almost as a question, his wide-eyed smile reaction to her hand on his cock the only answer she needed. “Quickly, okay?” and after an enthusiastic nod from him she pulled her hand out, took his hand, and lead them out the door.

Speed walking across campus hand in hand, they had short snippets of conversation only when they had to stop for a traffic light or for a crowd of people. ‘That was an amazing spanking, wasn’t it?’ ‘Yeah, I still can’t believe it happened’ ‘Does it still hurt a lot?’ ‘Yeah, but it feels so good too’ and other quick comments.

Arriving finally at her room, they hugged and kissed as each rubbed the other’s spanked bottom. Sara escalated with her hand on the bulge of his pants, and he responded with one hand squeezing her sore bottom and the other slipped between her legs feeling the humidity as he rubbed her pussy through her pants. Neither had ever done anything like this before, but neither had ever gotten such an arousing spanking with an audience before either.

Sara decided to take the initiative and knelt in front of Tim while opening his pants and pulling them down below his bottom, guiding him backward to sit on the bed. To Tim’s amazement she proceeded to pull his pants completely off, and after some strokes of his hard dick through his underwear, removed them as well, a delightful smile on her face as she saw, and took hold of her first erect penis.

For Tim, it was one shocking surprise after another today and the one to top all others was when Sara stroked his thick shaft bringing him to a gasping, shuddering climax his semen shooting high in the air, some of it landing on Sara’s arm. She didn’t have to ask whether he liked it as the smile on his face combined with the explosion made confirmation unnecessary.

Tim stood up and pulled Sara up with him for a passionate kiss that acknowledged the completely new experiences they were sharing. Before their lips separated, his hand was again between her legs, her labored breathing telling him to go on. Kneeling for her now, he also opened her pants, pulled them down, and helped her step out of them.

Her soaking wet panties just inches from his face, he slipped a finger into the slit defined by the sticky wet panties, sliding it in and out as Sara’s knees got weak. Turning her around to guide her to the edge of bed just like she had, he slipped her panties down as she sat, and pulled them off over her bare feet. Leaning back on her elbows she knew what she wanted, and Tim didn’t disappoint, with fingers of both hands exploring every fold and crease of her beautiful pussy. She came almost instantly when one finger found its way inside, her turn to shudder and gasp at the welcome climax.

Though he had no idea how to do this, Tim spread her legs further apart and sliding his hands slowly down her thighs, put his face in between and planted a firm, but gentle kiss on the warm, wet labia of her peach of a pussy. “Oh Tim!” she cried as she felt something building again. She gasped as his tongue slid into the warm wetness of her slit and though it wandered aimlessly all over those precious lips she built quickly to another even more explosive orgasm.

Pulling his face out of her crotch and to her face she kissed him hungrily unfazed by the musky taste of her own pussy on his lips. Tim had raised the bar and she didn’t hesitate to try and beat it as they again swapped places and she took his stiff dick, erect again thanks to her delicious pussy, into her mouth sucking and licking him while stroking what she couldn’t fit in her mouth. Tim pulled her off him just in time to avoid shooting into her mouth.

Both naked from the waist down, they removed the rest of their clothes and pressed their naked bodies together as they rolled around on the bed, just enjoying each other’s warm flesh. For more than an hour, they continued, repeating all they’d done with such abandon, they couldn’t believe that all this was totally new to them both, and sharing all these first-ever events was magical. So engrossed in their own limited lovemaking, they didn’t even notice her roommate come in and suitably shocked exit quickly.

Still, few words were spoken as they shared each other and knew the same thought was at the back of both of their minds; how and when were they going to do all this again!?

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Written by 2bespanked
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