Dinner Date with Mommy Pt. 03

It took a few more tries, but eventually she had opened him up enough that his bottom just couldn't keep the invader out any longer. Steve gasped as the widest part of the plug popped past the resistant ring of his anus and the toy pulled itself the rest of the way in.

Amanda watched his little rosebud clench on it repeatedly, the base shifting inwards slightly with each contraction. Then, grabbing the base in a firm hand, she began to pull it back out.

"Oh, oh, oh," Steve cried as he felt the plug start to stretch his hole again. With a final tug, the plug popped free, making his body convulse in response.

Inspecting the plug, Amanda found it to be adequately clean. It was obvious he'd done an acceptable job administering his first enemas to himself. She'd have to remember to praise him for it later. Good habits were worth encouraging, after all, and little ones like him needed all the positive reinforcement they could get.

She placed the plug at his entrance and pushed it back in. This time she simply pushed the whole length in with a single, smooth movement. Steve jumped as the plug unexpectedly stretched him so wide again, a little yelp slipping out as it did.

"That's right, pumpkin," Amanda said sweetly as she dragged the plug out again. "Be good and take it for mommy."

Over and over the thickest part of the plug stretched his bottom open, and Amanda even started to push it in to that point and hold it there to keep him stretched as wide as possible. His hole was starting to get a little sore, but the plug was also doing an admirable job of rubbing against his tickle spot.

Every time the plug popped past his entrance, the tip would jolt over it, making him jump. As Amanda increased speed until she was actually fucking him with it, the sensations started to get more intense. Not quite as amazing as her fingers had felt, but still good enough to make him pant as the plug continued to abuse his little hole.

Amanda's pussy was practically dripping as she worked the eager little slut over. She pulled her free hand back up under her dress and pressed the palm of her hand down over the top of her pussy in a slow circle that made her clit ache for attention. Idly she wondered if Steve had ever learned how to really eat a woman out, or if she'd have to teach him from scratch.

Shelving the thought for later, she decided she'd probably end up just sitting on his face tonight anyways. She wanted to be the one in control, and grinding down onto him until she climaxed would be a great way to get off while still maintaining the power balance they'd started to strike.

With one final push, Amanda seated the plug back into his bottom and used her palm to press it in as deeply as it would go. Steve's back arched and he inhaled sharply as the sudden stretching reached deeper than it had before. Releasing the plug, Amanda's hand moved to his bottom cheek, alternating between rubbing and patting him lightly.

"What a good boy," she said, her voice encouraging. "Now, are you ready for your punishment?"

Amanda watched the plug jump in his bottom as his cheeks clenched at the thought. To his credit, though, Steve responded immediately.

"Yes, mommy." His voice was barely a whisper, but he sounded determined.

"Good answer," Amanda said with a tinkling laugh. "First, though, let's get you dried off."

Grabbing his shoulder, Amanda helped him upright. Steve's posture looked a little unusual as he bent almost imperceptibly at the hips to accommodate the plug inside of him. Taking his hands, Amanda helped steady him as he stepped over the edge of the tub back onto the ground.

Steve stood uncertainly as she grabbed a towel off the nearby rack and flipped it open. He reached out to take it, but Amanda grabbed his arm with the towel instead and started to run it over him. Her movements were practiced and efficient as she made sure to scrub the towel over every inch of wet skin. She ignored his bottom until the end, though, when she used the towel to wipe up the excess lube that stubbornly clung to him. The lube took a little longer to clean up, but it still went pretty quickly, and before long she stepped back to admire her handiwork.

"Perfect," she said with a sigh of satisfaction, though it seemed to Steve that she wasn't really talking to him when she said it.

"Alright, after you," she said, suddenly ending her inspection and gesturing back towards the bedroom.

"Yes, mommy." Steve turned and started to shuffle uncertainly back into his room, but he jumped as Amanda's hand smacked up into his bottom hard enough to sting.

"Ah," he gasped as his bottom clenched in response, grinding the plug deeper up into him at the same time.

"Quickly, sweetheart," Amanda said, her voice taking on a warning quality.

Steve double timed it out of the bathroom, almost jogging on his way out.

Amanda chuckled and turned around to retrieve the paddle. She'd need it for the "conversation" they were about to have.

As she entered his room, she found him fidgeting nervously beside his bed. He looked so adorable as he visibly struggled to decide whether to cover himself with his hands or not.

"Hands behind your head, baby boy," she said as she crossed the room to stand in front of him. Her hands went to her hips, and with the paddle in hand she cut an imposing figure as she scrutinized him.

Steve's hands linked up behind his head, and he could feel how clammy they had suddenly become.

"Before and after most punishments I'm going to give you time to think about why you're being punished," Amanda said. "I find that it really helps to reinforce the lessons."

Taking a step forward, she reached out a hand and grabbed him firmly by the earlobe. With a quick tug, she had him up on his tiptoes. A few short steps later and she had his nose planted firmly in the corner across from his bed. Then she had him step back so that his bottom stuck out a touch and spread his legs until she could see the base of the plug sticking out behind him.

"Very good, pumpkin," Amanda said. "Now stay just like that and don't you dare move a muscle."

Giving his bare bottom a quick pop with the palm of her hand, she moved to finish getting ready for his punishment.

First she retrieved the chair from his desk. It was a simple piece of furniture that lacked adornment, but it had sturdy legs and no arms on the sides, so it was perfect for her needs. She moved the chair so her back would be to his bed when she sat down and set the paddle on top of the bed close enough that she could reach it without needing to get up.

With that out of the way, she reached into the nearby gym bag and pulled out the smaller of the two dildos along with the harness that had been hidden beneath them. She wouldn't use it on him tonight, but it would be a good scare tactic if she needed it. Besides, she wanted Steve to be crystal clear on where she expected their interactions were headed. She set the items down on the bed next to the paddle.

Going back to the bag, she fished out the leather cuff set and a length of rope before moving back to Steve.

"Time to get you properly dressed for your punishment, sweetheart," she said.

With his hands still behind his head, it was simple enough to attach the wrist cuffs. They snapped on quickly, leaving Amanda's hands free to fit him with the last piece. Larger than the other two, but of similar design, Steve realized it was a collar as it clicked shut around his neck.

"Put your hands behind your bottom," Amanda ordered.

Steve's hands moved down with indecent haste as he tried to show her what a good boy he was being.

Amanda smiled, her hands quickly tying the rope in her hand to one of his wrist cuffs before running the length up to a ring on his collar. She looped it through the ring and brought it back down to the other cuff and ran the rope through it. As she pulled to tighten the rope, Steve felt his arms being forced up behind his back. When they were almost parallel to the ground, Amanda tied the rope off.

"There," she said happily. "Now we don't have to worry about those pesky little hands getting in the way."

Reaching down, she dragged her nails across the exposed skin of his bum and gave his plug a little push. Steve shuddered at the sensation.

Satisfied, Amanda moved back to the chair and finally took a seat. Her eyes glinted as she leaned back to drink in the sight of him. So vulnerable. So uncertain. So eager to please. The dampness between her legs had grown to the point where it wouldn't surprise her to see a wet spot on her dress when she stood up.

She enjoyed the view for another minute or so before sitting up and affecting an air of cold professionalism.

"Alright," she said. "Come kneel in front of mommy."

Steve straightened up uncertainly, the position of his arms throwing off his sense of balance. Once he was upright, though, he quickly turned and moved to stand in front of Amanda. He struggled with his balance once again as he awkwardly kneeled down onto the rough carpet of his apartment floor.

Once he was seated, Amanda reached out and grabbed him by the chin so that his eyes were forced up to meet hers.

"Do you know why you're about to be punished, little one?" she asked, her tone measured.

Steve took a deep breath.

"Yes, mommy." His voice sounded higher than normal to him again.

"And?" she pressed. "Why are you being punished?"

It took him a couple of tries to get started as his voice seemed to fail him completely.

"Because I disobeyed you, mommy."

"That's right," Amanda said, nodding her head sagely. "And do you agree with my decision to punish you for your disobedience?"

The question caught him a little off guard, but he didn't hesitate.

"Yes, mommy," he said quietly. "You laid out the rules of the game and the consequences for breaking them. And I broke them."

His voice trailed off at the end, and Amanda could hear the regret in his words. Not just because he was going to be punished, but because he was genuinely sorry for disobeying her.

"Very good, pumpkin," she cooed, her hand moving to stroke his cheek gently. "That was an excellent confession."

"Now," she said, leaning back and patting her knee, "Come lie across mommy's lap so we can get this over with."

Steve's whole body tingled with anticipation as he shuffled forward on his knees. She directed him so that his head would be on her left side and his bum on her right, then helped ease him up and over her knees. He was light enough that even tied as he was, she had no problem juggling him into place.

The only complicated bit was making sure that his still-hard cock made it down between her thighs so he didn't hurt it while moving about. She had hike up her dress quite a ways and reach between them to guide it downwards before bringing her legs together to trap it in place.

Finally ready to get started, Amanda smiled at the prize perched on her lap. She ran her fingernails over the vulnerable skin of his backside, making him shiver and causing his cock to jump between her legs.

Reaching forward with her free hand, she took a firm grip on his waist and pulled so that he was tightly wedged in place with nowhere to run.

Amanda lifted her tightly cupped hand to about shoulder height and brought it down with a sharp snap of her wrist. Her palm cracked loudly against his defenseless bottom and his leg kicked in surprise.

"Ah," Steve squeaked. It hadn't hurt as bad as he feared it would, but it still stung. He managed to keep quiet as the second swat landed a few seconds later on his other cheek, however he did kick a little again.

The next swat came a little faster, and the next faster still until Amanda's hand became a constant blur of steady, methodical whacking. Each movement was punctuated by the clap of flesh on flesh and soon Steve was making cute little noises as the burning in his bottom really started to set in.

"Ouch," he cried after a particularly hard swat. "I'm sorry, mommy. Ow! I'm really sorry."

"Not yet, you aren't, sweetheart. Not by a long shot." Amanda paused a moment and rubbed her hand in large vigorous circles around his blushing bottom. "But we'll get there."

She started up again, harder now that the warm up was out of the way. The difference in Steve's reaction was immediate. His kicking became more emphatic and his hands pulled against their restraints as he tried to reach down and cover himself.

"Ah! Mommy, please!" he strained to keep his voice down, unsure if the sound would carry through his walls.

"We're just getting started, little one," Amanda said, her tone making it clear she'd tolerate no argument on the matter. "I recommend you get used to the idea of staying right where you are for a good long while."

Steve's backside had really started to sting. The swats were coming so fast now that he barely had time to feel one before the next was landing. The result was a quickly building fire that had him kicking his feet as the burning sensation started to overtake every other concern in his mind.

"Oh, please, mommy," he begged, his voice a quiet whine between his little exclamations of pain. "Please, stop. I'm sorry!"

"Sorry for what, pumpkin?" Amanda asked, her pace unchanged as she continued to roast his bottom.

"Ouch! For disobeying you, mommy. Ow!"

"And?" she asked expectantly.

"Oh, what, ouch! What do you mean?" Steve's voice had become high pitched mewl as he struggle to keep the noise down.

"Well," Amanda said slowly, her hand still moving at a quick tempo, "You went behind my back and let yourself out of your cage because you didn't think you could trust me to recognize when you were in real pain."

"Ah!" Steve yelped, his arms sawing back and forth as he strained to reach down far enough to protect himself. "Please, I, ouch! I don't understand."

Amanda sighed, her voice taking on the long-suffering quality of a person trying to explain something exceptionally simple to a child for the dozenth time.

"You chose not to call me and explain what was wrong because you didn't trust me to know when you'd reached your limit." Her grip around his waist tightened and the intensity of her spanks suddenly escalated until the sound of their impact echoed around the small room.

"This lesson is about trust, sweetheart," Amanda said. "You're going to learn that even if something is a little bit painful, mommy isn't trying to hurt you. If you'd called and told me your cage was hurting you, I would have told you about the key hidden in the gym bag."

Even with his bottom on fire, Steve still felt a little wave of shock roll through him. There'd been a key in his room the whole time? When he'd seen her put the key in her pocket he'd just assumed it was the only one. The thought made him feel... guilty. Not that he didn't already feel bad about disobeying her, but for some reason this felt worse. Like he'd failed at some level he couldn't quite put his finger on.

"Now do you understand?" she asked, her hand continuing to burn up his quickly-reddening bum.

"Owie! Yes, mommy. Ouch! I think so."

"Good boy," she cooed, her voice full of praise. "Now that you understand, when do you think mommy is going to stop spanking your little bottom?"

Steve whimpered and whined as a sinking feeling formed in the pit of his tummy.

"When you decide, Ah, that I've reached my limit? Oh!"

He leaned forward on her lap, his upper body dipping towards the ground as he kicked forward. His bottom danced about wildly as it struggled to find an escape from her tireless hand. The movement didn't even phase Amanda, though, and her free hand quickly steadied him back into place as her palm cracked down hard all across his sore flank without pause.

"That's exactly right, pumpkin." The strained quality of her voice made it apparent just how hard she was bringing her hand down now. "And do you know why?"

The almost unbearable fire in his bum ruled out any chance that he would figure it out right now and his voice started to crack as little sobs began to escape him.

"No, mommy. Ouchie! I'm sorry! Please, Ow, tell me."

Amanda laid on a handful of exceptionally hard swats that had Steve kicking like a swimmer before breaking off to shake the stinging out of her palm for a moment. Steve exhaled in relief at the sudden halt to the onslaught.

"To show you that even if something feels unbearable, mommy knows exactly how far she can push you without doing any real damage."

Steve felt her shift around, but was too occupied by the miserable state of his bottom to pay it much mind. Until he felt something cool and smooth touch his bottom, at least. With a flash of panic, Steve realized she'd grabbed the paddle off of the bed.

"No, no, no, mommy, please, no," Steve pleaded with her, his voice an urgent whisper. "Please! I'm so sorry. I'll never disobey you again! I promise!"

Ignoring his cries for mercy, Amanda lifted the paddle high off of his rump and brought it down with a tremendous crack across the fullest part of his bottom.

The impact took Steve's breath away for a moment. It was a thousand times worse than her hand had been! How could anything hurt so much?

He sucked in a deep breath and let it escape in an explosive hiss as his feet twitched sporadically and he fought to keep from crying out.

Amanda was impressed. He'd managed to stay quiet despite the walloping blow with the wicked paddle. Most of the little boys she'd spanked before had tried to climb right up off of her lap after the first swat with that implement.

Lifting the paddle back up, she brought it down just as hard again on a single cheek. Then the other and back again. Slowly she worked herself back into a rhythm and the paddle cracked over Steve's bottom with excruciating regularity.

Steve lost count quickly, but he guessed he'd taken about 20 hard swats before he broke down again and started to beg.

"Owie! Please, mommy! I can't take it anymore. It hurts! Ow, my bottom! Please!"

Amanda enjoyed his miserable pleading for a few more moments, her arm bringing the paddle down a touch harder on her last couple of swats before taking a quick breather.

Steve's whole body slumped in relief as the paddle stopped scorching his hind quarters for a moment, a little sob escaping him.

Amanda switched the paddle to her other hand so she could brush her fingers over his red hot bum. Steve flinched as he felt her hand running over the burning skin, then relaxed slightly as he realized that her gentle touch was helping to sooth the agony in his bottom. The tops of his cheeks to the crease of his seat was a uniform bright red with slightly darker splotches mixed about from the holes in the paddle.

Amanda smiled at the results. He'd done remarkably well so far for his first spanking. Kicking, crying, and begging were to be expected. As much as he'd jumped around on her lap, though, he hadn't tried to pull himself away from her or stand back up.

"Still," she thought to herself, "We're not quite done yet."

Judging by his reactions so far, he'd probably need just a little bit of help to get through the next part.

Leaning down from her seat, she reached into the side pocket of the gym bag and pulled out a tiny brown vial with a screw on top. Giving the bottle a little shake, she pondered the amount of liquid inside of it. If they used it sparingly, just the tiny amount in her hand would last them for weeks.

Amanda smirked to herself. It's not like it really mattered. She had a dozen such bottles at home, all full and ready to assist naughty little boys through the toughest parts of their punishments. When she decided that Steve had settled down enough, she unscrewed the cap and held it in front of him.

"Put one of your nostrils close to the top of this bottle and inhale," she said. "It'll make you feel better, I promise."