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Walking Encounters - Part 5 - Amanda

"Alex gets much more than he expected!"

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Author's Notes

"Amanda is convinced of Alex's suitability sooner than she'd planned."

3 - Summoned

Amanda knew exactly what she wanted to try next with naughty boy Alex and started planning the day after their first encounter. He’d done well with a vague role-play that had no defined scenario, so she wanted to see how he’d do when it was pre-defined, and she’d use one of her favorites: a summons to the Headmistress’s study.

There wasn’t really much planning actually apart from setting a day and time, creating, and delivering the communique, and setting the room up. Setting up the room was easy, only having to remove furniture not fitting the image of an academic’s study, which meant removing all, but the two chairs needed, pulling the punishment horse out of the corner to a conspicuous location, and selecting several implements some of which were displayed only to instill some fear in the naughty student.

She was anxious to do it as soon as possible but not before he had fully recovered from the first time. Their first meeting had been on Tuesday past and while the following Saturday would be safest, she feared he’d have weekend plans and took a chance on Friday.

Next, she created the invitation, a ‘summons’ to the Headmistress’s office which she had done many times for Dan. She recalled, happily, that it had been one of their favorite scenarios. Sitting at her computer, she knew exactly what it needed to look like and say …

Office of the Headmistress

Student, Alex Bradley, is hereby summoned to report to the Headmistresses study for the reason and time prescribed below:

Reason: Cheating on Math Exam

When: Friday, 5:00 PM (immediately after classes)

Note from Headmistress: Master Alex, as a senior and one who is no stranger to my study or the punishments administered therein, I thought it best, given the time and short notice to tell you that your casual classroom attire will be acceptable. Don’t be late!

Printed on card stock to look suitably official and placed in an envelope, she personally delivered it to his mailbox on Friday afternoon, to leave some, but not much time for anticipation to build. In order that he’d find it in time, she sent him a text at four o’clock suggesting he check his mailbox. The wheels having been set in motion, she now had to wait for both his acknowledgment and arrival, her anticipation already building and felt most acutely between her thighs. She only needed to dress appropriately for her role, which meant both sternly and provocatively.

 

Hoping he’d hear from her again soon, the events of Tuesday evening never seemed far from Alex’s mind that week, providing inspiration for several ‘self-improvement’ sessions in the bathroom, the sting and color of his butt ample stimulation for the first day at least.

By the time Friday afternoon arrived, he was disappointed as he’d all but given up hope for the weekend as he thought plans for days off needed a bit more advance notice. He worried that she may have regretted what she’d done, especially considering her reluctance to go beyond the wonderful spanking she’d given him. On the other hand, she may just have her own weekend plans already.

Mid-afternoon, he was on a call with a consultant that had severely disappointed the Company with the work done, so he wasn’t in the best of moods either, but that changed with the arrival of a text …

Check your mailbox!

… which had him hastily hanging up with the idiot consultant and running to the street to get his mail, which hadn’t usually arrived by this time he worried, but opening the box he found the envelope addressed to ‘Master Alex’ and immediately smiled. He couldn’t resist the temptation to open it right there in the street and with his dark mood instantly changed, he ran back inside to his phone to text a reply …

I’ll be there, Miss.

Good boy.

… was the short, but welcome reply.

Though she hadn’t been specific about how he should dress, he thought he knew what she meant insofar as casual was concerned and put on a pair of black slacks with a proper crease and a white polo shirt, buttoned to the neck and tucked into his pants, under which of course were the tighty-whiteys she’d liked before. Oxford shoes, black socks, and neatly combed hair completed the look. He’d had a little less than an hour to close out the workday, get dressed and get to her home which was ample time it turned out as he was done with twenty minutes to spare; twenty minutes that was as bad as having to wait while in position for an impending spanking.

As he walked to her home, he mentally prepared for his role. Apparently, he’d been accused of cheating on a math test which would probably be cause for severe punishment, which didn’t worry him as he was showing no signs of their prior engagement. He decided he’d deny the allegation in the hope that, proven guilty, the punishment would be more severe. Beyond that, there wasn’t much else he could prepare for apart from knowing he’d be leaving without relieving the erection that he was already sporting.

He arrived at her home exactly on time, and finding the door ajar, decided she wanted him to enter on his own, as her home was substituting for a school office building, and he’d be expected to find his way to the Head’s study. He closed the door behind him making as much noise as possible to warn her of his arrival should she need to assume her role in any special way.

“Come in, Master Alex,” she said when he knocked on the study door and he entered to find her seated behind her desk writing in some sort of file. “Have a seat. I’ll be with you shortly,” she instructed and continued writing.

As expected, she had also dressed appropriately in a dark suit and a formal white blouse, with a rounded collar trimmed with a narrow row of lace, which matched the cuffs. He couldn’t see the knee-length skirt until she stood later, and how tight her blouse was until she took off her jacket. Black stockings and pumps completed the ensemble.

He noticed the punishment horse immediately as it was out of the corner and positioned for use. He also took note of several implements laying on the desk including a hairbrush, two paddles, and a strap, and assuming he’d be feeling them all before the night was through wondered just how much further Amanda was accelerating his punishments. Finally putting down the pen and closing the file she addressed him directly.

“Good afternoon, Alex,” she said dispensing with the formal ‘master’. “You know why you’re here, of course.”

“The note said that I cheated on the math exam, but I …” he started but was interrupted.

“Yes, well your math teacher, Miss Collins is insistent that there was definitely cheating going on, but we’ve since learned that you weren’t the one copying answers from another student.”

“Then what am I …”

“The guilty party, it turns out, was Cindy Wilkins who has already been rather severely punished,” she said looking over at the implements on the desk corner. “However, Cindy was sitting next to you during that exam, and Miss Collins saw her looking at your exam paper repeatedly, while you looked back at her and made sure your answers were quite visible. Having compared your test answers and found Cindy’s to be identical to yours we knew someone was cheating. Confronted with the evidence and well into her punishment, Miss Wilkins confessed to avoid additional strapping, saying you hadn’t taken any answers from her.”

“So, then I’m in the clear?”

“Not exactly. She’s a very pretty girl, isn’t she, Alex?” she asked with a devious smile and went on without an answer to her question. “Even in her school uniform, that’s rather tight, I might add, I imagine she can be quite beguiling … able to convince the many adoring boys around her to do her bidding?”

“No Miss, not me,” Alex lied.

“Lying is not a good strategy at this point, Master Alex,” she said getting quite stern. “By the time she was feeling the strap across that cute, little bottom of hers, she was quite willing to describe how she put your hand between her legs and easily convinced you to allow her to see your test answers.”

“I’m sorry, Miss! I …”

“Yes, I’m sorry too. I can see how that temptation would be exceedingly difficult to resist,” she said empathetically, “but whatever your reasons, you are still complicit in cheating regardless of who got answers from whom. Given your role in this affair, I can say your punishment won’t be as severe as Miss Wilkin’s was, but I don’t think that will be of much comfort to you by the time we’re done here.”

Both Alex and Amanda were impressed with each other’s ability in role-playing, but Alex in particular loved how she wove her web so thoroughly around him and awaited what was to come with excitement and a little fear. Straps were not his favorite, but he would admit the feeling afterward was unmatched by any other implement so long as one got through the strapping.

“Stand up, Alex,” she said as she too stood, took off her jacket, and came around the desk to take the seat he’d just vacated. “In front!” she commanded and immediately set about opening the belt, button, and zipper securing his pants, and yanked them down well below his cheeks. Pushing him away a bit and turning him sideways she told him to bend over, as she reached for the long, wooden school paddle from the desk.

Holding him only by a hand on his back, she proceeded to give him twelve hard swats of the paddle on his tight underwear. Gasping at each impact and pleading for her to stop, he was relieved he still had his underwear on for this most painful of paddles. This was one of her favorite surprise tactics and she used it sparingly to keep that element of surprise alive.

“Consider yourself lucky you weren’t bare for that!” she said putting the paddle back on the desk and turning him to face her again. “But you won’t be needing these now!” she said stripping his underwear down to sit atop his pants. “Get over my knee!” she ordered with that familiar stirring in her panties.

Constrained by his pants, he shuffled to her side, bent across her lap, and settled quickly into position hoping it would be quite a long spanking with her hand. He couldn’t help his contented moaning as she peppered his bare bottom with brisk, but firm spanks. He always loved the beginning of a hand spanking as it had often been quite a long time since he’d been spanked, so he was having a very hard time hiding his pleasure, little knowing he was playing right along with her plan.

Amanda knew well how to give a firm, painful, but also pleasurable spanking without it feeling like just playful foreplay. Scolding him while mixing in hard spanks to emphasize certain words and using her free hand to gently squeeze and caress whichever cheek wasn’t getting smacked at the moment. They both loved repeated spanks in one spot followed by squeezing or scratching that newly tender spot, so she mixed plenty of those into what she considered just a warmup.

There was something he’d tried unsuccessfully to understand about the fantastic feeling of being over a woman’s knee with a bare bottom. It was more than just the submission, more than handing over control and more than the delectable feeling of her hands on his ass. Perhaps it was the sum total of all those aspects, but even though he often didn’t get sexually aroused while being spanked, he always loved it, savored it, and cherished it partly because he was never sure when he'd get spanked again.

Today, over Amanda’s knee he was getting increasingly hopeful that that was about to change. Besides the heavenly feeling of her skilled spanking hand, the awesome soreness, sting, and color that was building slowly, and that she was paying more attention to his pleasure as well, this would be really the first time in his life that the focus would be only on his bottom. He’d had women who wanted to spank him more than be spanked, and he did enjoy that, but there were also many times when he had been hoping to be the punished one only to find she wanted it that night, and even in that situation he felt he was the submissive one complying with her desires.

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That was going to be different with Amanda. She made it clear that she did not get spanked and had outright said that her husband got spanked at least weekly! On top of that, she didn’t want any sort of formal commitment and her primary interest was spanking, which meant that any time they were together he was going get a spanking and here he was getting his second in less than a week.

A small voice in the back of his head asked if he was sure he wanted this. He really did enjoy having a naughty girl over his knee especially when they’d asked, even begged to be spanked, but even then, his needs were always second to hers. Maybe he wouldn’t like it in time, but he was positive that he wanted to try and as these thoughts settled in his mind and the sting in his bottom grew, he knew he had to make sure Amanda liked it as much as he did.

“Oh, Miss! It hurts! It really hurts! Do you have to hit me so hard,” he said in the most convincing role-playing voice he could muster.

“Young man, I shouldn’t have to remind you that this is a spanking! Punishment for unacceptable behavior and if it doesn’t hurt it doesn’t do any good whatsoever!” she said thrilled that after several hundred spanks he was finally feeling the pain, however much she knew he wanted it. It helped her to renew her efforts and reduce the length of the already short rests he was getting.

Please, Miss!? I don’t know how much more I can take!” he said in an ironically true statement as he didn’t know how many hundreds more he could take; and want!

The involuntary squirming and jerking of his body and the gasps, moans, and cries of pain, in addition to driving her on, were also filling her panties with slippery, wet secretions and telling her the scenario was playing out perfectly. Time to ramp things up a bit!

“Alright, get up, you naughty boy!” she said as soon as a flurry of a dozen hard smacks delivered to each cheek, in turn, was complete.

“Oh, thank you, Miss!” he said in just more than a whisper, certain that she wasn’t finished.

“Don’t be thanking me yet, young man. I’m not even close to being done with you!” she said taking notice of the look of relief on his face. ‘Oh my god, he’s going take more than Dan ever did!’ she thought, feeling the squishy crotch of her panties. “I’m getting rather hot trying to make you feel the pain!” she said as a compliment to his endurance and started opening her blouse as Alex stood and watched with his hands behind him and an erection growing with each opened button.

“Mmm, do you like watching me take my clothes off?” she asked as she let the blouse fall to the floor behind her, thrusting her small and firm tits in his direction. “Hm?” she questioned as she gave his cock a long, firm stroke ensuring full erection seconds later.

Reaching behind her, she pulled the short zipper of her skirt down and slowly eased the waist down over her hips. Alex’s eyes widened to her delight as some black lace was revealed, but his mouth opened in shock when the skirt fell to the floor exposing a sexy garter belt holding up her black stockings, but even more arousing, sheer, black panties displaying the tight slit beneath and a large wet stain that only she knew was growing due to his response!

“Oh Miss!” he loudly groaned at this unexpected sensuality, immediately wondering how he’d get through tonight complying with her request from the night before that this be a spanking only.

Amanda was soaking up his exquisite reaction and even teased him a bit, bending over to retrieve her blouse and skirt, showing off her full round ass purely for his pleasure. She couldn’t wait for the finale she’d planned and had to remind herself to be patient as the reward would be even greater.

“That’s enough of a break! Go bend over the spanking horse,” she ordered. “Not at the side, at the end!” she corrected him and watched as he lay his torso down on the padded surface, pleased that she’d estimated the height almost perfectly. “Back up a bit … a bit more … there!” she said as his dick dropped off the end of the cushion. “Good! Now spread your legs, don’t bend them. That’s it. Now don’t move an inch or else!”

She walked up to him and gave each cheek a really hard smack before walking around to stand in front of him, his eyes planted on her crotch and following her around.

“Now … you’re going to get spanked again, another looonnng spanking, but even then, I won’t be done because then I’m going to use my favorite leather paddle on that cute … and very sore? … bottom of yours until you’re begging me to stop! Judging by your endurance so far, that’s liable to take a very … long … time! Ready?” she asked, bending over with her face inches from his.

“Yes, Miss. Please spank me,” he said wanting it to sound like compliance with a rule, but instead sounded like a desperate plea.

“Oh, I will!” she chuckled, and the spanking resumed.

A new position always brought a new and usually appreciated element to his spankings and this was no different. One advantage of this one was that he could look back and see Amanda in action, watching her sexy body wind up and twist into the hardest spanks, bringing extra pleasure with the savory pain and when she noticed him watching her, she moved to stand in a better line of sight for him. He smiled and got one from her in return.

“Miss? You claim you’re just punishing me, but I think you enjoy it! Do you like spanking me, Miss?” he asked after a long series of about ten spanks to one spot on each cheek in turn, repeated over and over, finishing the round with twenty really hard ones followed by her fingers providing almost unbearable stimulation to the tortured flesh, only to be repeated on the other side.

“Such an impertinent question to be asking your Headmistress!” she replied as his body writhed in response to her fingernails on his ass, “but I know you enjoy it!” She spanked again, ten? … or maybe twenty? “Don’t you?” Another round, harder and harder. “Come on! Admit it! You like to get spanked!” Fast and hard now had him squirming again.

“No, Miss! It hurts! It really hurts,” he protested and got twenty in like five seconds.

“Yes! It hurts! … but you like the hurt, don’t you?” she said not stopping now and keeping the same fast pace. “Don’t you!!” Ow-ow-ow!!! “Tell me!” Owww! “Tell me you like it!” Ow-ow-ow!! “Tell me you want it!”

“Oh god! Owww! Yes! Yes, I like it! Spank me! Spank me harder!” he cried as her hand was a blur building the sting to ferocious levels.

“Good boy!” she said as she slowed down with long spaces between excruciatingly hard spanks, Alex just moaning in response. ‘First real surprise coming,’ she thought as she took his soft, but still long cock in hand and stroked it, gently bringing it back to near full erection before she stopped the spanking and stroking, Alex’s mouth wide open in surprise.

“Now … you’re going to get paddled,” she said as she stepped over to the desk and picked up a large round leather paddle, the business end flexing freely despite its thickness. “You want to get paddled, don’t you!” she said as a statement, not a question. Getting only incoherent mumblings, she smacked his ass with the paddle. “Tell me!” she demanded and then taking his cock in hand again, smacked the other cheek hard. “Ask me to paddle you!”

“Oh, Miss! Please? Please paddle me. Give me a good, hard paddling!” he said weakly and unevenly as she stroked him ever more fervently.

She expected it wouldn’t take long to make his cock spurt on the floor, so she tried to build slowly, while still paddling with mixed hard and playful swats of the paddle. Every time she felt he was even a little close, she’d paddle hard and fast, making him forget his needy cock and concentrate on the painful but heavenly paddling, thrusting his bottom up inviting harder attacks.

“Yes … I do love spanking you, Alex! … and you’ll find out just how much with rather frequent turns across my knee!”

“Oh Amanda,” he said out of character as she increased the pace of her strokes and the intensity of the swats to a shuddering spasmodic crescendo, the result of which was his spent body lying on the horse and strings of semen on the floor between his legs.

With one hand rubbing his flaming red cheeks, she moved to his side so she could see his extraordinarily satisfied face, with a tired, but happy smile on it.

“Amanda, that was the most amazing …” he started but stopped when another shudder passed through him in response to her inserting a fingertip into his ass. “Amanda, please … please let me …” and he stopped, and thinking she was just teasing him again, he watched with hopeful expectations as she pulled her panties down, and turned around to bend over with her luscious bottom inches from his face as she stepped out of the wet underwear. When she took his hand, put it between her legs, and pressed it hard against her dripping, wet cunt he knew she wasn’t teasing any longer.

“Yes, Master Alex … you may thank me for spanking you!” The surprise of her action woke him from his stupor and his fingers sprang into action, making her gasp for a change. “Come … over here,” she said helping him unsteadily get off the horse.

Sitting in the chair she’d spanked him in, her ass near the edge and her legs spread wide, she had him kneel between them, but he needed no further help or direction from that point as his hands caressed her smooth thighs, while his face headed for her pungent pussy. Gasping and arching her back in response to something she hadn’t felt in years, Alex showed her how gratefully and expertly he could lick her hungry pussy.

With his arms wrapped around her thighs, his tongue licked and probed every delectable fold and crease of her fragrant flower. Feeling her urgent need, he revved it up, sucking her wholly into his mouth while his tongue slathered her slit and they were both rewarded with her trembling climax, but he wasn’t going to stop there. He wanted to see her cum at least once more.

His fingers joining the party in her pussy, they’d spread her open for his tongue, penetrate her with hard thrusts and even return the favor of a fingertip in her anus while she bucked, writhed, and moaned uncontrollably surprising him with another quick orgasm, crying out, “Oh god! My pussy! Fuck!” in uncharacteristically slutty language.

“Holy shit!” she screamed as Alex went for number three not being the least bit subtle or gentle about it. His two middle fingers thrusting hard into her gaping cunt were effectively spanking her pussy as they smacked into her hole. His tongue darting around his fingers settled on her clit, where flicking and sucking it drove her to the precipice once more to jump off with sexual abandon. He pulled his mouth away but continued to gently stroke her saturated slit.

“No! No more!” she cried with heavy uneven breaths. Alex stood up and standing behind her, massaged her neck, shoulders, and arms gently as she slowly calmed. Her tits still firmly held in her bra he realized he’d neglected them tonight but knew she didn’t want to escalate things again, so he left them for another time. When she looked up at him above her, he bent down and kissed her lovingly.

“Did I hear you say something about frequent trips across your knee?” he asked hopefully.

“Yes, I did,” she said standing up and hugging him tightly, only as they were separating, did she gently squeeze his very sore bottom, adding, “I’d love to spank this cute, little bottom many, many times if you’ll let me?”

“Yes please, Miss,” he replied in his naughty student role and a bitten lip. Amanda smiled and smacked his bottom playfully.

“Would my naughty boy like a glass of wine?”

They went to her living room and sat wrapped in each other’s arms while they drank their wine and talked about the amazing evening they’d just had. They couldn’t find a single thing they’d change or didn’t like and while it had gone according to Amanda’s plan, she had to admit that it went so much better and further than her plan.

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Written by 2bespanked
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