“Would you like me to warm them up for you?” she asked with her hands caressing his slightly stinging bottom.
“Yes, Miss!” he answered quickly leaving no doubt.
They stood, and she took his hand again, about to lead him to the bedroom when he tugged on her arm to reach back and grab the hairbrush.
“Good idea!” she said, remembering they were learning this together, and regardless of their roles, they each had something to contribute.
Feeling like this time with Miss held the promise of being far better than the last, he followed dutifully behind, anticipating his first hairbrush spanking, hopefully over her knee. Her less demeaning approach had him wondering if something had changed causing her to see she didn’t have to diminish him to dominate him. He’d do anything she asked now without question and wouldn’t need the safeword she’d told him to have ready.
Happy to see the same vanity bench in the middle of the room, he couldn’t help smiling when she sternly ordered him across her knee after sitting near the end.
“You hold on to that,” she said when he tried to hand her the brush. It was a minor gesture, but he’d always liked scenes where the one being spanked was made to hand over an implement for use on their bottom.
With her seating position his chest rested on the other end of the bench, and his ass bent over her thigh. She had him lift to guide his cock between her thighs that clamped it tightly. Patting his bright pink buns, she put her other arm around his waist.
“Why are we here, Simon?”
“So you can spank me, Miss!” he replied demurely. She didn’t respond, so he added what he thought she expected. “So you can give me a long, hard spanking on my bare bottom, Miss!”
The first swat immediately followed his request, and a pattern of alternate spanks followed. While it wouldn’t bring her to climax, having him over her knee and spanking him like a naughty boy enhanced it like no other foreplay she ever had. It didn’t matter whether he was squirming in her lap, trying to evade her punishing hand, or lifting his hips and begging for more; she was always wetter when she’d finished even a short spanking, and she knew it would always be a centerpiece of their time together.
“Ow! Ooo! Ow-ow-ow! Please, Miss! Please don’t … Owww!”
“Please don’t what, Simon?” she asked as she smacked one cheek at a time, the number increasing with each cycle.
“Please don’t stop!”
“Good boy!” she praised as she delivered a finale of sorts with ten hard smacks on each cheek.
Caressing his brightly painted cheeks, one hand or the other tapped on the plug’s end, reminding him of its presence. Seeing him lift his hips for encouragement, the taps turned into harder pushes as though she’d force the end in as well.
“Hand me the brush, Simon,” she instructed, holding her left hand out, and he obediently gave it to her. She rubbed and tapped the large oval back of the wooden brush over both cheeks, letting him feel and prepare for it.
Without warning, she lifted the brush and delivered a hard swat to the top of each cheek.
“Yeow!” he cried at the new intensity.
After a short pause, she began in earnest, swatting each cheek from the fleshy top to the soft lower part before treating the other to the same. Each strike seemed to target a small spot, unlike her hand that encompassed a larger area, but all those spots grew together to create a bright sting and deep-seated burn.
“Ow! Oww! Oh my God, Miss!” he yelped.
“Hurts a bit more, does it, Simon?” she laughed.
“Yes, Miss!” he squeaked in a high-pitched voice.
Knowing it was his first such spanking, she eased up a bit, not only to give him a break but to avoid hurting him so much he couldn’t take what else she had planned. Increasing the speed only, she watched his body tense, tucking his bottom in before giving him a well-deserved rest.
He’d only relaxed a few seconds when she turned the brush over and lightly dragged the stiff bristles across his deep red cheeks.
“OH! Oh shit!” he cried as the stiff bristles electrified the hypersensitive flesh.
Switching to the other cheek, he had the same reaction. It was almost a needles and pins feeling: brighter and sharper in its touch. Intensely pleasurable, it left him wondering whether he could take any more, but wanted it even so.
“Oh, fuck, Miss! That was amazing!” he said after two repeats, the effect diminishing with each. “Ow-ow-ow-owww!” he screamed as she peppered one side with a half dozen hard smacks, and then, “Ohhhh my God!” when she used the bristles again on the freshly punished cheek.
She repeated it once more for the other side and then resumed paddling alternate cheeks just above the thigh even harder at a one-per-second pace. He thought fleetingly about needing the safe-word he didn’t have but decided he wanted the intense pain, hoping that each more brutal spanking prepared him for another, even more intense.
Many swats later, she stopped. She could see bruises starting to surface, a bluish spot that would grow and probably turn purple or black before the night was over.
With her permission, Simon slid backward off her lap and remained kneeling as his hands both soothed and squeezed his tortured cheeks. He was proud of having withstood the painful spanking but worried about taking any more tonight.
Monica turned on the bench to sit with its length behind her and lay back, supported by her elbows. Spreading her legs, she wordlessly demanded a show of gratitude.
“Thank you for spanking me, Miss!” he said as his hands glided up her thighs and surrounded her pussy as though forming a target for his approaching tongue.
“Oh yeah! That’s it, Simon! Eat me! Eat my dripping wet cunt!” she encouraged and watched for a short time as his tongue invaded her pussy.
With nothing gentle about it, he licked, slurped, and probed her pussy as though heading for an imminent end. He had no idea how close she was when she put her feet on his shoulders and laid back on the bench.
She could feel it coming on fast and marveled at the level of arousal the more intense spanking had created. Pushing off his shoulders, she lifted her hips, pushing her pussy into his face with even more force.
“Christ, Simon!” she screamed as the sensations continued to build past the point she’d expect to climax. Finally, with a loud wail, it erupted, squirting into his face with the first stream and another over his shoulder to land on the ceramic tile floor.
As soon as she could stand, she got up, went to the bed, and bent over with her hands on its surface.
“Come fuck me, Simon! Fuck me hard!” she demanded, waggling her bottom at him.
He practically jumped into position and teased her by running the tip of his dick through her slippery wet slit, gathering the slick juice on its tip. With it poised at her gaping hole, he pushed it in slowly but, feeling no resistance, rammed the rest in hard, his hips slapping against her ass.
“Oh yeah!” she cried in appreciation of his punishing deep thrust. “Jam that cock into my tight, wet pussy! Harder!”
Doing as he was told, he grabbed her hips and pulled her onto his thrusting shaft, the collision an exciting element itself. Propelled forward by each impact, she was pulled back to be impaled again and again. She said she wanted it hard, so he was going to pound her pussy and give it all he had.
“I’m … I’m gonna … gonna cum, Simon!” she gasped as she pushed back even harder. “Ungh! Ungh! Ohh, fuck!” she screamed as she came, but Simon wasn’t quite there yet and continued his assault on her cunt. “Oh God! Oh God!” she exclaimed as another climax built before the first had subsided. “Huh! Huh! Oh, Jesus!” she cried as she felt him flood her pussy.
She fell forward onto the bed, gulping air in deep shuddering breaths. Simon sat on the bed next to her, stroking her back as he recovered as well and thinking this was the most incredible experience he’d ever had.
“Simon! Where’d you learn to do that? … and don’t tell me college!” she laughed as she rolled over and sat up.
“No, Miss. I didn’t learn it anywhere. You brought it out of me!” he replied with tears in his eyes.
She was genuinely touched by this show of emotion, possibly feeling something similar as nobody had made her feel like this young man. She reached to put a hand on his cheek and turn his face toward her so she could kiss him gently, with tender, soft lips.
“Simon, I’m not done with you yet!” she stated, trying to get him back to the present.
“Yes, Miss!” he said with a smile.
Moments later, he was lying on the bed with her pussy grinding into his face. She was going to take him in her mouth, but she wasn’t sure he could take the act of kindness and thought he needed a bit of a shock to get him back in line.
She’d cum once already when she turned her back to him, his face embedded between her cheeks, and bending forward to suck him off, but before he came, she guided him into her pussy for a reverse cowgirl ride.
They repeated much of what they’d already done as variations on a theme, but without any more spanking. Monica correctly judged that he would only take, at best, one more spanking. Climaxes came fast and furious, leaving her bed a wet, sticky mess. They’d both lasted much longer than last time, but eventually, it was time for a conclusion, and she had a unique finale planned.
“Get on the bed, Simon! I’m going to sit on your face one more time!” she said with a devious smile.
Simon was more than happy to obey and even happier when she turned her back to him as it left his arms free to pull her down onto his face and finger her pussy. He’d love a sixty-nine, but Miss had a different plan.
“Lift your legs up!” she ordered and wrapped her arm around them, pulling them back over her shoulder. “What are you waiting for? Eat me!” she demanded as her free hand reached for something under her pillow.
Simon’s eyes opened wide when he saw the large oval paddle of black leather. Enough time had elapsed with all their other activities that he looked forward to another spanking, but even better, he was going to get his first paddling and in the diaper position, also new to him.
“Now, Simon,” she started delivering the first swat. “I’m going to – swat! – keep paddling – swat! – your bare bottom – swat! – until you – swat! – make me cum – swat! – understand?”
“Yeff Miff!” he mumbled with a faceful of pussy.
Disbelieving the fantastic combination of sensations, he was in no hurry to make her cum, but with her grinding her crotch and ass into his face, it wasn’t long before his face was yet again painted with her milky white nectar.
“That was too quick!” she gasped between panting breaths. “Again!” she demanded as she lifted off his face to allow him to answer.
“Oh God, Miss! Yes! Pleaff!” he said, the last word cut off by her suffocating, wet pussy. The swats had been coming with several seconds between, and she stopped after only a few more.
Pulling his legs and body back further, she put them under her arms so she could free her other hand. The paddling resumed as before, though at a slightly faster pace. Less than a dozen swats later, a climax was building nicely, and, wanting them to cum together, she used her free hand to grab hold of his cock and jerked it like they were running out of time.
Both were crying out as the summit approached, their bodies squirming and twitching every which way as the peak was reached with a simultaneous scream. With the deepest breaths yet, they struggled together to get enough air, Simon’s hampered by her pussy still in his face until finally she realized and lifted off.
She fell onto her back beside him, and, after a few moments, he rolled to his side to face her. He looked at and then gently touched her heaving chest assuming permission to do so from last time still applied. With eyes still closed, her hand landed on top of his, and expecting her to remove it, he was surprised when she pressed it harder into her chest, guiding it from one tit to the other.
“You outdid yourself, Simon! You were incredible!” she said with smiling eyes.
“No, it was you, Miss! You made it all happen!” he replied genuinely, not because she expected him to.
“It takes two of us to make that happen!”
“I guess so,” he said with a sad face and glassy eyes.
“What’s the matter?” she asked, noticing his mournful look.
“It’s nothing.”
Her comment about needing the two of them to make their magic had revived a plaguing thought that this was a limited time opportunity. ‘How long would it last?’ he asked himself. He didn’t know her precise age, but he knew she would normally be going out with men much older than he was and figured it was only a matter of time before he was replaced. It had also occurred to him that he would normally be with someone closer to his age, and while, at the moment, he couldn’t imagine replacing Monica with another, he’d have to live with the hope that, eventually, he’d find someone like her. His spirits lifted with the thought that he’d enjoy what they had for however long it lasted and he’d do his best to ensure it lasted a long time. Her voice woke him from his contemplations.
“Did you notice anything different about this time compared to last?” she asked sitting up.
“Yes,” he replied, unsure whether he should say what it was.
“I wasn’t as stern or angry with you?” she phrased as a question and when he nodded, she continued. “I’m sorry I was so mean to you, Simon! I was acting like I thought I should to be a proper Domme. Did you like this better?”
“Well, um, Miss. I …” he stuttered not sure if he should be honest or say it didn’t really matter what he liked better as an authentic sub would.
“You can call me Monica when we’re talking like this.”
“I’d prefer to keep calling you Miss, if that’s okay?” A small smile accompanied her nod. “I would accept any way you’d prefer, but today was fantastic for me. You still told me what to do and punished me when I didn’t do it right, but I just want to do whatever pleases you most.”
“Thank you,” she replied with a gentle kiss, and the thought that he could be someone’s perfect sub as he always seemed to have the right answer to her questions, but for her sake, she hoped that would never happen..
She moved to get off the bed and he followed suit. Holding her arms out to him, he fell into her embrace and a soft, loving kiss followed a hug that made him feel loved in a way no other had.
Once separated, they turned toward the door to return to where they’d started, Monica following, she saw the jeweled plug winking at her from between his cheeks.
“Bend over the sofa again, Simon,” she said, and he practically ran to comply.
She knew he was expecting another spanking, but it was the plug she was after. Getting a grip on the large flange, she tugged on it a few times, which he seemed to like, but then pulled it out. Simon tried to relax, but it hurt about the same coming out as going in. He’d liked having the plug in his ass but was now glad it was gone.
He heard the plug land on the floor and moved to get up, but when she spanked him, he lifted his hips wanting more.
“Did you like the plug, Simon?”
“Oh yes, Miss!” he replied grateful for the feel of her hands spanking him.
“Perhaps something larger next time?
“Oh! Um. I think so, Miss?”
“Is there anything else you’d like to try next time?” she asked as the spanking continued to renew the sting he found so delicious.
“I’ve always wondered what a strap would feel like.”
“Wait right there!” she said leaving the room, but returned seconds later. “You mean like this?” she asked holding up a flexible leather strap a couple of inches wide and maybe a foot and a half long; happy that another of her adult store purchases was met with approval.
“Oh, Miss! Could I …”
“You want some now?” she offered hoping he’d say yes and give her the chance to practice with it.
“Yes! Please?”
“How many?”
“Six?” he asked.
“You can have more!”
“Ooo! Ten, then!”
“Ten it is! I want you to count them!” she said as she laid the leather across his cheeks and rubbed back and forth.
Simon closed his eyes to concentrate on the new sensation. “One!” he cried with the first tentative lash. Monica knew a proper follow-through was best when using a strap, but the first didn’t land flat, the edge of the strap painting a thin line across his lower cheek.
“Ohh! Two!” he said, counting the next that was softer but landed just right. “OW! Three!” he counted obediently with the first proper lash. It was so much more painful, but a different sort of pain; more immediate, duller and with a penetrating depth. His body jerked upright with each searing lash, and he worried if he’d be able to take the full ten.
Monica was enjoying it as much as he was, wondering again if she’d defined her dominant desires correctly. She delivered the remaining seven much like the third and smiled while watching him furiously rub his now-striped bottom when they were done.
She sat in the same chair where she watched him undress earlier. He stood up, still rubbing his flaming red bottom, whose bruises were now in full bloom. He didn’t feel he needed permission at this stage to begin dressing, but he looked over at her frequently just to be sure and could feel his cock growing again at the sight of her incredible nude body. He discreetly turned his back to her so she wouldn’t see.
She loved the way he looked at her with his simple adoration as opposed to the glaring lust most men showed her. There was a time for that, too, but Simon seemed to know when that was, and showed his respect for her at other times, realizing there was a person inside the gorgeous body others just wanted to use as a plaything.
“All buttoned up?” she asked when he turned to face her again.
“Yes, Miss. Thank you! I enjoyed it more than you know!”
“I could say the same! Do it again next Saturday?”
“Oh, yes! Please?”
“I’d love to do it sooner, but I think your bottom is going to need more than a couple of days to recover,” she said as they headed for the door.
“I’m hoping it feels like this for a couple of days, but if you want me to come over sooner, just tell me. I’ll do anything to make you happy, Miss!” he replied as they arrived at the door.
“Well, I don’t think you’d want me to hold back because you’re still sore, would you?” she asked with a raised eyebrow. He shook his head in agreement. “But if you’re really ready sooner, just let me know and maybe Wednesday or Thursday would work, okay?”
“Yes, Miss! Good night!” he said, turning to accept another loving hug and goodbye kiss.
“Good night, Simon,” she replied and watched him leave.
—===<<<O>>>===—
Their continued escalations have them wondering how far into the D/s world they want to go. Will they rethink their individual desires? Please remember to ‘Like’ and/or ‘Favorite’ my story if you enjoyed it and … Thanks For Reading!!
