Dinner Date with Mommy Pt. 03

The work went slowly, but it became apparent that his idea was entirely possible. However, as the cage creeped down the pressure became even tighter around his already-cramped balls. Seeing that he only needed a little more space to reach freedom, he grit his teeth and pressed on.

As the pressure started to become unbearable, Steve finally got enough space between himself and the cage to worm a finger down into it and fish his cock up through the gap. He was actually kind of thankful the cage had kept him only semi-erect, because if he'd been fully hard there would have been no way to get it out.

As his cock finally sprang free, Steve groaned, his eyelids drooping with relief. His hands started to massage the kinks out of the tender flesh while he brought his eyes back down to survey the damage.

Turning it from side to side and craning his neck down close, he saw dark red spots in a couple of places that felt a little sensitive to the touch. Other than that most of the discomfort had subsided just by being out of that damn tube. Of course, he started to have another problem almost immediately.

No longer subject to the cruel confines of his cage, his cock could finally stretch itself out. Thanks to the unrelenting mental and physical stimulation he'd endured since having the cage fitted, his erection was prodigious. He didn't think he'd ever actually seen veins stick out on his shaft like that before. The pressure was intense and it felt like it was constantly flexing of its own accord.

He could feel a little soreness coming on from it, too. He'd experienced something similar once when he'd masturbated too many times in a day. If he took it easy for the next day or so it wouldn't get to the point of actually being painful.

"Still," he sighed to himself as he continued to inspect his cock, "It's good to be out of that damn cage."

"Is that so?"

Steve felt a chill sweep through his body the likes of which he'd never experienced before. Time seemed to dilate as he looked over his shoulder at the doorway into his apartment.

Standing in center of the frame, Amanda's chilly expression could have given a thundercloud pause. She had her arms crossed tightly under her chest, one hand holding the awful little paddle that Steve feared he was about to become intimately acquainted with in a short period of time.

Steve felt like a deer, and her eyes were the headlights as she stalked forward. She took slow, measured steps as she contemplated just how severely she'd need to discipline him for this transgression. First, though, she needed all the facts. She'd only just arrived a moment before, and hadn't had much time to observe him in the act.

After she'd let herself into the unlocked apartment, she'd gone to peek into the bathroom. When she saw him hunched over himself in the tub, she'd known exactly what was going on and had given a small smirk of satisfaction. Little tingles spread through her pussy as she'd turned to retrieve the paddle from its place on his wall. Maybe securing the cage a bit too tightly had been a dirty play on her part, but it certainly was an effective trap.

When she'd returned to the doorway, she had taken another moment just to watch. He hadn't appeared to be masturbating. The way his arms moved made her think his ministrations were much too gentle for that. It looked as though he'd only just managed to get free of the device and was still in the process of rubbing the ouchies out of his little man when she'd spoke up to reveal her presence.

"Lucky him," she thought as she approached the petrified boy, "If I'd caught him in the act, he'd really be in for it."

"Stand up," she commanded, her voice cracking hard enough to make him flinch.

Steve scrambled to his feet and turned to face her. His cock was fully hard and was pushed up towards his belly slightly as it strained to fit over the top of his cage. His hands seemed undecided on whether they thought trying to hide the evidence was a good idea at this point.

"Put your hands behind your back," Amanda said, freeing him from having to make the decision himself.

They disappeared in an instant and Steve started to fidget instead, his feet unable to stand still as his eyes flitted about the room.

Reaching out a neatly manicured hand, Amanda took hold of his chin and forced him to look at her.

"Well?" She asked, her stare pinning him in place. "What do you have to say for yourself, little one?"

Steve's jaw worked soundlessly for a handful of moments before he finally closed it and swallowed to work some moisture back into his mouth.

"Sorry, mommy," he finally managed to squeak out. "It hurt so bad. I just couldn't take it squeezing me like that anymore."

Letting go of his chin, Amanda reached down and grabbed his cock from underneath. Steve winced and gave a little kick as she roughly handled the sensitive skin, pulling him closer by his manhood. Steve tiptoed forward gingerly, then sighed as she finally stopped yanking on him.

Amanda leaned down to take a closer look. There were a few chafed spots that looked painful to the touch and even a couple of indents still visible from where the plastic of the cage had really been cutting into his skin. He'd only had it on for a few hours, too.

She mused to herself that the cage had perhaps been a hair too tight, especially for someone new to that kind of confinement.

"You didn't use this opportunity to pleasure yourself, did you sweetheart?" she asked, her voice still cool.

Steve shook his head emphatically. "No, mommy. I promise."

Amanda leaned back, folding her arms again and tapping the edge of the paddle against her side as she examined him.

"Alright," she said after a long pause. "I've decided."

Steve swallowed hard at her fatalistic declaration, not daring to move a muscle under her penetrating gaze.

"The cage wasn't appropriately sized," she said. "That's my fault. I should have done a shorter test run before locking you in that one for such a long period of time."

Steve felt a wave of relief flood through his body at her words. He felt like a death row inmate who'd been pardoned in the 25th hour.

"However," she continued, making him tense up again. "You still disobeyed me when you removed your cage without my permission. And for that, you'll still be punished."

"But..." Steve started, only to be cut off by a warning finger.

"No 'buts,' little one," she scolded, making him shrink in on himself. "You have my phone number. Instead of blatantly disobeying me, your first thought should have been to call me and ask for permission."

Dropping the ice queen act for a moment, she let some warmth into her features and relaxed her stance as she reached out and ran a hand gently over his cheek.

"I'm not a monster, baby. I'm your mommy." Her voice was soft and reassuring. He found himself leaning into her touch as she continued. "I might enjoy testing your pain threshold from time to time, but I would never really hurt you on purpose. If you'd called and told me what was happening, I would have given you permission. But now, because of your own actions, you're going to be disciplined."

Amanda held her breath on the inside. It was the moment of truth. This was when he would either submit to the punishment, and to her, or he'd walk away. But her experiences in similar situations hadn't prepared her for what came next.

His stare was a thousand miles away as he looked at the ground without seeing it. Slowly his eyes filled with tears and his shoulders started to shake.

"I'm sorry, mommy," he choked out between sobs. "I'm really sorry."

Amanda felt a thrill of joy wash through her. It was the perfect response.

"Hush, baby," she said as she set down the paddle and reached out, taking his trembling body into her arms. She cradled his head on her shoulder and bent down to plant a kiss on his forehead. "I know you're sorry."

Steve felt utterly humiliated. He didn't even know why he was crying. It was like all the negative emotions he'd ever tried to hide were suddenly erupting to the surface. He couldn't help it. As he buried his face into the soft fabric of her dress the tears started to burst out in a torrent that threatened to overwhelm him.

"It's okay, sweetheart," Amanda cooed as she started to sway back and forth gently. "Let it all out. Mommy's here."

It took several minutes for Steve to start to regain his composure. Wrapped in his mommy's warm arms, her soothing voice in his ear, his heart-wrenching sobs eventually subsided into choked sniffles. As she continued to rock him, even the sniffles slowed down almost to the point of stopping.

Leaning back, she beamed down at him. His eyes were still unfocused, but when he noticed her staring at him he glanced up from under his brows, an embarrassed look crossing his face.

He sniffed and cleared his throat. "Sorry, mommy."

"You have nothing to be sorry about, sweetheart," she reassured him, her smile the most genuine expression he'd ever seen on her. She really was the most beautiful woman in the world.

"Except disobeying me," she added with a coy smile.

Steve laughed despite himself and nodded his head. "Yes, mommy."

"Now why don't we take care of that little issue real quick?" she said with a meaningful glance towards his still trapped and swollen member.

Reaching into her pocket, she produced the key to his cage. With a quick twist and pull, he was free. Steve's body slumped as the tube slipped off and the pressure was suddenly relieved from his balls. The ring followed a moment later.

"Oh, thank you, mommy," he moaned as his hands started to massage the lines where the plastic had bitten into the soft skin of his sack. "Thank you, thank you, thank you."

Amanda reached down and gently pulled his hands away, replacing them with her own. Steve moaned, little whimpers escaping him as her hands expertly soothed the awful pain away.

"Are you going to be a good boy for mommy during your punishment?" she asked quietly.

Steve swallowed hard, but nodded his head after the briefest of moments. "Yes, mommy."

"Good boy," she said with a smile. "Now let's get you cleaned up the rest of the way."

Reaching to the faucet, she turned the water back on and let it run until it was steaming again before hitting a switch that turned on the showerhead. Adjusting the spray so that it would be mostly against the far wall, Amanda moved Steve to stand beneath its arc.

Using her hand to interrupt the flow of water over his head, it would trickle down across his body and her hand would follow shortly after. She gave him a quick rub down from the tops of his shoulders, all the way down to his toes. Then she took a long moment making sure she got all the soap off of his groin. Steve moaned as her delicate hands rubbed and massaged at his most sensitive skin, occasionally wincing as she passed over an exceptionally tender area. It was over all too quickly, though, as her hands left his still-hard cock unsatisfied and continued onward.

Grabbing him by the wrist, she turned him around so his back was to her. She repeated the routine on his backside from top to bottom before she began to pay special attention to his cute little bum. Water cascaded down his back as her fingers traced up and down the length of his bottom crack.

Steve licked his lips nervously as her other hand gripped his shoulder and bent him forward slightly to give her easier access. Her fingers slowly slid deeper into the groove, scrubbing thoroughly as they went. Steve jumped as they finally brushed against the delicate tightness of his little hole.

"It's okay, baby," Amanda cooed, her other hand moving up to rub his back in soothing little circles. "Just relax and let mommy get you nice and clean."

Steve nodded his head, his breath coming in short gasps as her nimble fingers poked and rubbed against his entrance. A little moan escaped him and he bit his lip in a vain attempt to silence himself.

Amanda pull back for a moment so she could grab the nearby bottle of lube. She drizzled a decent amount at the peak of his bottom cleft so it would drip down the length of his crack before pouring a generous application onto her hand and setting the bottle aside. Bracing a foot on the edge of the tub, Amanda resumed her exploration of his bottom as she leaned in over the bath so she could reach her free hand around in front of him. Her fingers found a nipple and started to run little circles around it while she bent forward until he could feel the heat of her breath on his ear.

"You don't have to be quiet, baby," she purred. "Mommy likes to know she's making you feel good."

Her tongue snaked towards his earlobe, hooking around it and drawing it into her warm mouth. Steve felt a wave of goosebumps roll through his entire body as her soft tongue played with the sensitive area before starting to nibble on him. Amanda's middle finger started to circle around his clenched bottom hole, gently pushing against his resistant opening. He was helpless before the onslaught of sensations.

"Oh, god," Steve gasped, his hands clenching and unclenching as he struggled to keep his bottom pushed out so his mommy could keep playing with him.

"Good boy," she murmured into his, her voice alight with passion. "You're behaving so well for mommy, but I need you to try to relax your bottom. Can you do that for me, pumpkin?"

Steve nodded between shudders and did his best to relax his hole, but it was hard to concentrate with her hands still working over his most private places.

Still, it was enough, and Amanda smiled as the tip of her finger finally slid in to his tight orifice. Steve stiffened at the feeling, his hole squeezing tight around the invader.

"Relax, baby," she breathed in his ear. "Focus on your breathing. Nice and steady."

It took Steve a few measured breaths before she felt him start to loosen up again. Amanda couldn't have been more delighted with how quickly her little toy was coming along. Her finger began a short pumping motion with emphasis on moving side to side to help stretch the small opening a little wider. She could feel him rhythmically clenching on her finger every few seconds before managing to relax again. As the clenching became less intense and he started to relax faster, she wriggled her finger a little deeper. A whine escaped Steve's lips.

"Does it hurt, sweetheart?" she asked gently. "If it hurts, mommy will stop."

Steve shook his head in a jerky motion.

"No, mommy," he said in a half-groan. "It doesn't hurt, it just feels... weird."

"I know, baby," she cooed. "Just try your hardest to be a good boy and mommy can make you feel so wonderful."

Just as she said those words, her finger found that tickle spot inside of him, making his whole body jump. The sensation felt much stronger than it had before.

Amanda giggled at the reaction. "I see all that hot water made your little pleasure bump especially sensitive."

Steve felt himself blush bright red. Still, he bit his lip and bent over a little further. The feelings her finger was eliciting from him were too good to deny.

With a grin, Amanda obliged. Her finger ran little circles around the spot before pulling almost all the way out and then pushing back in again. He could feel his tight passage slowly opening up to accommodate the digit, even as it pushed deeper with each successive thrust.

Amanda's face was fixed with a sly smile. This one was going to be quite the anal slut. His hips had already started bucking back at her. The motion looked involuntary. She doubted he even realized he was doing it.

She guessed it would be a week, maybe two if she went slowly, before she was using the smaller of the two dildos in the gym bag on him. She couldn't wait to hear him whine and groan as she buried it in him up to the hilt while it was attached to her harness. The thought drove her desire to even greater heights and her panties felt soaked through as her legs squished together.

She picked up the pace and started to work her finger into him a little harder. Steve didn't complain, though. If anything, he moaned harder.

"Ready for the next step?" she asked as her finger hooked inside of him and started pulling his hole open in one direction before switching to a new spot and doing the same there. Steve grunted as he felt himself being stretched almost to the point of discomfort each time, but she had a knack for stopping right before he could voice a complaint.

"Alright," she said in her sing-song voice. "Here it comes."

Steve felt her finger tracing around his still-tight pucker, then felt another one join it. Swallowing hard, he braced himself for what he knew was coming next.

The pair of fingers started to press at his entrance, but it was still too tight of a squeeze to fit.

Undeterred, Amanda dipped a single finger into his hole again and gave him a series of long, powerful strokes. Then she pulled back out and tried two fingers again. They got a little further this time, and Steve could feel his hole really starting to stretch. Amanda repeated the process several times, and each time her fingers would get a little closer to slipping in.

Steve gasped as he felt them finally slide home.

"There you go, baby" Amanda said, her voice soothing. "Take it for mommy."

Her fingers began a controlled pistoning motion, twisting and working to open him up further. Now that she was past his stubborn rosebud, the strokes quickly became deeper. In just a few moments she had her fingers buried in him up to where they met her hand.

Steve's reactions had only become more powerful and a low, continuous moan had started to escape him. As her movements became more aggressive, the sound started to take on a rhythmic quality that matched her thrusts. It wasn't long before she was really giving it to him with some force. She made sure to pay special attention to his tickle spot as her fingers plunged deep into his tight hole. Peeking around his front side, she could see a long string of precum had begun to leak out of his cock.

"Enjoying yourself, sweetheart?" she whispered in his ear, taking a moment to nibble the sensitive flesh of his lobe.

"Oh, yes, mommy," Steve groaned with his eyes closed, his words coming in breathy hiccups that matched the rhythm of her thrusts.

Steve opened his eyes and looked down at his straining cock. Every fiber of his being wanted to reach down and take hold of it. A few short strokes is all it would take to push him over the edge of what felt like it would be a life-changing orgasm. That wasn't an exaggeration, either. Now that he'd experienced the kind of pleasure her fingers were giving him, he was positive it was something he wanted more of.

After a few more minutes of working to open him up, Amanda finally pulled her fingers back out. Steve whined as she did so, his bottom arching up in search of further stimulation.

Amanda chuckled. "Don't worry, baby. Mommy's just getting ready for the next step."

She reached down and grabbed the lube and small jelly plug from where they sat on the side of the bathtub. Coating the plug with a generous helping of the slippery substance, Amanda cocked her head as she considered the object. About 4" long and ¾" at its widest point with a large, flared base, it was the quintessential beginner's anal toy.

"Reach back and spread your cheeks for me, little one." Amanda said.

Steve didn't hesitate. His hands had started to pull his bottom apart almost before she finished the sentence. Smiling, she placed the tip of the plug against his exposed hole and began to push. It took a few pokes before the end finally slipped up into him, making him gasp. Then, with methodical purpose, Amanda eased the plug up his tight canal.

As the widest part of the plug neared his entrance she started to feel some resistance. Slowing down, she pushed until she heard him grunt in discomfort before letting the plug slide back out a little. His hole clenched sporadically on the plug where it was still inserted, and Amanda let him settle down before pushing it back in again to the same point.