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Miss Judy Suprises Again! - Part 4

"Does punishment become pleasure?"

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Author's Notes

"Part 4 of what is now a 6-part series, Keep Your Grades Up, thanks to KeithW66 for the suggestion that sparked several ideas!"

“I am sympathetic to your needs,” Miss Judy started with no intention of telling them of her own occasional painful desires. “I’ve had students who enjoyed their time across my knee before, but none resorted to the extraordinary measures you two have taken to have your bottoms spanked. I have a proposal for two different solutions to this problem, but as they will entail even more spanking today, you are free to decline. Let me add that you won’t be spanked awfully hard unless you choose to … and with you two it wouldn’t surprise me if you did despite how sore and bruised your bottoms are already.”

“Yes, we’d like to hear what you have in mind,” Sara said, while both smiled weakly and continued to rub each other’s sore bottoms.

“Good. That will entail a demonstration as well as some participation on your part,” she said as she got up, walked around the desk, and took a seat in one of the chairs. “Okay, I want you over my knee, Sara. I’m going to spank you again, but if at any point it hurts too much, just tell me and I’ll stop, okay?”

“Yes, Miss Judy,” she said getting an inkling of that familiar feeling in her pussy. She carefully lay across Judy’s lap, whose hands provided soothing caresses of her bruised and sore bottom. “Tim, pull that other chair up close so you can see what I’m doing.”

Tim sat in the chair, his knees practically touching Miss Judy’s, and watched as she softly rubbed Sara’s bottom, the redness and blue bruises making it, in his opinion, even more beautiful. Judy explained what she was doing as her hands wandered all over Sara’s back, bottom, and legs, even dipping deep between her thighs getting a loud moan of approval from her. She explained the hypersensitivity of freshly spanked cheeks and scraping her fingernails very lightly across the tender skin had Sara gasping and arching her back, effectively pushing her bottom further into Judy’s hands. Tim took all this in but wasn’t quite sure where this was leading.

“Often, even with an extremely tender bottom from spanking such as Sara got today, additional gentler spanking …” Judy paused and began lightly spanking Sara on alternate cheeks increasing the intensity only slightly causing Sara to exclaim ‘Oh my god!’, bucking and writhing on Judy’s lap. “… is surprisingly welcome, especially because her bottom is so tender.”

Gasping and writhing on Judy’s lap as the demonstration continued, Sara couldn’t believe it. Her bottom felt so sore and yet this gentle spanking was making her crazy with desire for more.

“Do you see, Tim?” He nodded with eyes wide, not believing either. “As sore as she is, some gentle spanking and …” pausing again, she slipped her hand between Sara’s legs with fingers sliding easily into her dampening slit while still spanking and kicking Sara’s gyrations into overdrive as she nearly squirmed right off Judy’s lap. “… some stimulation of her highly sensitive pussy will make her …”

Slipping her two middle fingers into her pussy elevated her arousal to the point of coming, spasmodically shaking and breathing erratically as the orgasm crashed over her body, Tim dumbstruck by the sight. “… make her come explosively. Do you think you could do that, Tim?” Getting a vague affirmative answer, she added, “Let’s try it shall we?”

Helping the still-shuddering Sara off her lap, she guided her back down across Tim’s lap, Sara smiling at the thought of being there. Encouraged to do what she had just done, he started spanking her but having no experience he was spanking a bit harder than Judy had, yet Sara still loved it. “Oh, Tim!” she cried as the feeling of being over his knee and getting spanked by him was reason enough to be writhing and gasping yet again, another orgasm clearly on its way.

Having loved the thought of pleasing Sara before with his tongue, this was many times more exciting with Sara crying, “Spank me, Tim!” repeatedly as he smacked her sensitive bottom even harder than Judy had. Switching to his left hand for spanking, his right slipped into her slippery slit with Sara crying out again, “Put your fingers in my pussy!” Fingering her tight, little cunt she came even more violently than before leaving Tim smiling proudly at what he’d done for his beautiful Sara.

Eventually, calm enough to get up, she turned to sit on Tim’s lap and wincing at the pain in her bottom, exclaimed, “Oh Tim! That was wonderful!”, threw her arms around his neck, and kissed him passionately.

Judy couldn’t believe how well this was going and her sodden panties reminded her of her own arousal. She wasn’t done with these two yet, but she was already yearning for it all to happen again. One more step to get them on the right track she reminded herself, hoping her own hungry pussy could wait.

“Okay, it’s Tim’s turn!” she said with a smile, getting more disbelieving looks from them. “Yes! Come on, Tim. Over my knee,” she said patting her thigh with Tim at first hesitant, but then rather eager as he realized or hoped he was in for similar treatment as Sara had just gotten.

Explaining to Sara as she had done for Tim, she started by showing her how to position Tim’s now rock-hard cock between her thighs and grip him there. As sore as his butt was, he was very surprised at how good it felt to be spanked again, gently though it was. ‘What an amazing day’ he thought as he savored the resumed spanking, but when Judy scraped her fingernails across his sore cheeks, he squealed in delight with the feeling of his dick between Judy’s thighs adding to the intense stimulation. While spanking him still harder again, she spread her legs and reached down to stroke his dick and he nearly went through the roof. She stopped quickly wanting Sara to enjoy his ejaculation.

“Okay Tim, time for Sara to spank your naughty bottom!” she said wording it that way for Sara’s benefit. Smiling broadly at each other despite the burning bottoms they still felt, Tim happily laid across Sara’s knee.

“Spank me, Sara! Spank my naughty bottom,” he begged using Judy’s phrase. Sara’s smacks were quite tentative at first but with urging from both Judy and Tim she worked her way up to an appropriate force given his red, blue, and purple cheeks. Sara was in her glory, grinning from ear to ear and wondering why it had never occurred to them to spank each other. Seeing Tim wincing in pain, she congratulated herself with ‘You can do this!’ yet realized that today she needed to back off.

Not needing any instructions, she knew what was next, spread her legs enough, and reached down to get a hold of Tim, his pleasured reaction was immediate, and it wasn’t too many strokes and spanks later that he shot his load on the floor, in the grips of his own orgasm on Sara’s lap.

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Having calmed himself, he stood up and pulled Sara up to him, hugged her tightly, their bodies pressed together for as much flesh contact as possible. For several minutes they embraced, with kisses, tears, and hands all over their bodies, even their battered bottoms not off limits. Eventually, they separated, remembering Judy’s presence, and turned to face her, seeing a proud smile on her face.

“Thank you so much, Miss Judy!” Tim offered first.

“Yes, thank you! This was the most amazing afternoon and I’m sure we’ll remember it forever! … the fun and the punishment” Sara added, wanting Miss Judy to know she hadn’t forgotten their deserved punishment.

“It was truly my pleasure!” she said sincerely. “I love seeing you two get together like this, though why you’d never considered spanking each other is still a mystery to me!”

“It is funny, isn’t it,” Sara began. “You know we’re a little behind … no, a lot behind our classmates as far as anything sexual is concerned so discovering our mutual interest in getting spanked was a huge revelation for us and we both loved being across your knee and the way you spanked us, I guess we didn’t think there was any other way. Are you still going to spank us when we really get a bad grade? Seeing how much we like it, there won’t be much motivation in it.”

“Well, maybe I have the answer for that as well. You remember I said I had two possible solutions to your need for spankings?”

“Yes, I do. What was the other solution?” Tim asked.

“You’re right that spanking you for bad grades is silly at this point, new stricter schedule or not. Judging from today, despite the higher level of pain, you seemed to enjoy getting spanked together, am I right?”

“Yes, at the beginning it was exciting,” Tim offered as he started collecting his clothes to get dressed.  

“Yeah, seeing … not just hearing Tim getting spanked was getting my panties wet, even though I knew we were in for something very painful,” Sara added taking Tim’s cue to start getting dressed.

“So, instead of getting spanked for bad grades, perhaps you’d like to get spanked for good grades,” she said laughing at the simplicity of such an idea.

“Wow!” Tim said first.

“Oh my god, Miss Judy! How would that work?”

“You’d come to me each week; we’d look at your week’s work and as long as all grades were above an A … you’d go over my knee and get your spanking!”

“Really!?” Sara practically screamed.

“Uh-huh. Taking turns over my knee while the other watches, side by side over my desk, and maybe even some paddling?” she tested.

“I’m not sure about the paddling,” Tim joked, “but sign me up right now!”

“Me too!” echoed Sara.

“Good! So … every Saturday afternoon?” she questioned and getting eager nods continued, “When all the week’s grades have been posted, we’ll see together if you’ve gotten all A’s and earned your spanking. Mind you, if one of you doesn’t make it, you’ll have to just watch the other get spanked,” she warned.

“That’s okay. I love watching Tim get spanked,” Sara said laughing.

“What about this,” Judy posed, “the higher you’re average for the week, the ‘better’ the spanking? Hm? Maybe get into the hairbrush or paddle if you’re in the mood!? That way we all benefit!”

“Oh my god, Miss Judy! Can we start next week?” Sara asked enthusiastically.

“Yeah, I don’t think you’ll want to start tomorrow given the state of your bottoms today. I’ll create some kind of schedule based on your grades and we’ll use it next Saturday.”

“You said we all benefit, Miss Judy. How Sara and I benefit is obvious, but how do you benefit?” Tim asked. Sara nodded as though this question occurred to her as well.

“You’re both so innocent and naïve!” Judy said, shaking her head. “That’s one of the things I like about you but … after today I would think that answer is obvious as well. Couldn’t you see how much I was enjoying spanking as well as touching you two?” she said still surprised they didn’t get it. “I love spanking my naughty students, especially you two!”

“You enjoy inflicting pain?” Tim asked disbelieving.

“Not always, sometimes it’s just for the good of the student and/or fulfilling my contractual obligation, but you’d be surprised how often it isn’t really painful, where I know I’m giving pleasure as well. And you two have just fulfilled almost every fantasy related to spanking I’ve ever had.”

“I guess we should be flattered. Thank you again, Miss Judy! I already can’t wait till Saturday!”

“Thank you! Now, unless you have any other questions, I need to go change my panties after I’ve … you know!” she said not really caring if they knew how she was going to spend the rest of the evening reliving their afternoon together with her fingers and some toys in her pussy.

“Oh … um, yes … well we should go too. Thank you again, Miss Judy,” Tim stammered, and, taking Sara’s hand, they turned to leave, but with the same idea in mind, they both went over to Miss Judy and gave her a genuinely grateful hug. Overcome with his display of affection Judy pulled them both into a powerful maternal hug.  

They walked across campus just brimming with things they wanted to say to each other but knew it would launch a very long conversation, none of which could be shared with all the other students out this early evening. Shared smiles and meaningful eye contact was all they had until they got to Sara’s dorm.

Finally, inside her room with the door securely locked, they fell into each other’s arms and hugged, kissed, and touched all over, giggling as they smacked each other’s sore bottoms a bit more than playful. Finally, Sara stopped and just looked into Tim’s eyes questioning.

“Tim, do you remember when Miss Judy called us lovers? Do you think that’s what we are? I mean, to be lovers wouldn’t you have to be …”

“In love,” Tim finished as a statement, not a question. “Yes, I do think of us as lovers, because I really love you, Sara!”

“You do!?” Sara asked, Tim’s kiss was her answer. “Oh, Tim! I love you too! We’re so good together and I can’t imagine being with anyone else!”

“I think I’ve known for a little while … love,” he said deciding on that term of endearment for Sara, “but like so much else, I was afraid to think it, let alone say it, but after today, I don’t think I’ll ever be afraid of anything as long as I’m with you, Sara. I love you!”

“Mmm, I love hearing you say that! … and I love you too, more than you can imagine. There is something I think we’ve been afraid of together,” she said, and, seeing Tim’s reaction, she knew he knew what she was talking about. “Will you make love to me?” she asked, still a little afraid of his answer.

He answered by removing her blouse, and a minute later they fell on the bed, naked and wordlessly declaring their mutual love for each other, gently losing their virginity … and their naivete together.

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Written by 2bespanked
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