Dinner Date with Mommy Pt. 03

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Go back in time to see how Sophie became such a sissy.
18.8k words
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Part 3 of the 4 part series

Updated 06/09/2023
Created 11/18/2018
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Part 3 is going to go a little off track from the previous two parts. I've been asked numerous times for more backstory on Sophie and Amanda, so we're going to go back in time to the day after the events of Meeting Mommy to see how their relationship really began to evolve into the kafkaesque clusterfuck of sexual depravity you're all so fond of.

This story includes the following: Femdom, enemas, butt plugs and anal play, diapers, spanking, humiliation, CBT and chastity, face-sitting and domestic servitude.

Enjoy!

__________________

Part 3

Sophie's head swam in a combination of exhaustion and wine as she unconsciously snuggled closer to Victor. Stuck somewhere between grogginess and true sleep, she clung to his wide, warm frame as her thoughts wandered from place to place.

Her mommy, Victor, old girlfriends, feelings of confusion and nervousness; each flickered by briefly, shapeless but eliciting deep emotions she couldn't quite put a name to.

The one recurring thought was the taste of wine in her mouth. It really was a rare treat. Her mommy had trained her for almost a full month before she'd been allowed to have even a sip of alcohol during their relationship.

It had been a month of extreme changes and world-altering paradigm shifts. The seeds of those changes had been planted during their first date, but it was the morning after their first date, when Amanda had shown up to his place before he was even out of bed, that the shape of their future together really began to come into focus.

The memory came unbidden. It was one of many such memories that had started off uncertain, and even scary at times, but had eventually become a linchpin of their beautifully twisted relationship.

~~~~~~~C~u~e~D~r~e~a~m~S~e~q~u~e~n~c~e~M~u~s~i~c~~~~~~~ ;)

Amanda wasn't one to be hindered by standard social conventions, especially with such a delectable morsel in her sights. When she knocked on Sophie's, then Steve's, door with the sun barely up, she did so loudly enough to be certain he'd hear.

Steve had peeled himself out of his warm bed, the cold air making him acutely aware of his nakedness. Well, aside from the soggy diaper was wearing. He rubbed his bleary eyes before peeking through the shades of his window to see who was outside. Expecting the landlord, or maybe a solicitor, his heart skipped a beat when he saw who it was. Amanda winked at him and waggled a large gym bag that she had with her.

Panicking, he moved away from the window and checked his reflection in the mirror. His tummy tightened in response. He looked like a wreck. Disheveled hair, soiled nappy, he even had red lines on one cheek from where he'd been laying on his pillow.

He tried to at least battle his hair into some semblance of order, but it was a lost cause.

Amanda knocked again, and maybe it was his imagination, but the rap-rapping on his door seemed less patient this time.

Swallowing hard, Steve reached for the handle, his other hand flicking the locks off so he could open the door just enough to peek out.

Before he could say anything, Amanda swept the door wide open, exposing his diapered lower half to anyone walking by.

With a squawk of sudden panic, Steve jumped far enough inside to hide himself before running back to the window to see if anyone was outside, but Amanda was the only other person in sight.

"Good morning, sleepyhead," Amanda said as she stepped in and closed the door behind her.

She wore an expensive looking pink pastel business dress and cream colored heels, which made the black gym bag in her hands look a little out of place. She set the bag aside and approached Steve as he peeked out the window again.

"Don't worry, sweetheart," she said, giving an amused little laugh as she ran a hand delicately over the pillow-wrinkles on his cheek. "Mommy's the only one who saw your little nappy."

Steve's face went scarlet and his eyes dropped to the ground in embarrassment. He'd forgotten how she made him call her that the night before. After making him beg to be allowed to cum, her firm hands had expertly milked his needy cock to orgasm and forced him to fill the diaper he'd worn with warm, sticky goo.

But as mortified as he was by the memory, the thought still brought a tingly feeling to his lower half. Part nervousness and humiliation, part arousal. His deeply blushing countenance showed the former while his quickly hardening cock showed the later, forcing his soggy diaper to tent outwards.

Amanda noticed immediately, a sly smirk coming to the corner of her mouth as she stepped even closer. The heels she was wearing gave her just enough of a height advantage that she was the one looking down at him.

"Such an excitable little one, aren't you?" she murmured quietly as she reached out and pressed his wet nappy to his now-stiff member with the flat of her palm. Her fingers curled under and then up to cup his little coin purse as well as she intimately massaged him to deepen his excitement.

Steve moaned and tried to back away, but Amanda's free hand snaked around behind him. Holding him firmly in place, her fingers continued their teasing caress through the damp material.

"Does baby need a change?" she asked, her tone somewhere between baby talk and seduction as her hand continued to trace over his pulsing member.

Steve shuddered under the attention, his head still fuzzy from sleep. His compliance was assured as he humped back up at her hand, seeking more of those delicious tingles she was stirring up in his tummy. There was no resisting her skillful manipulations. He knew he'd do whatever she wanted, even if he wasn't ready to admit it aloud.

Steve nodded his head and thrust back into her hand again, hoping she might not make him say what he feared she wanted him to.

"Nice try, sweety." The amusement in her voice was obvious.

She moved her free hand to his chest and pushed against it, her clothed breasts touching his bare chest and their eyes coming within inches of each other as she leaned in to back him against the wall.

"Use your words to tell mommy what you want, baby." Her voice was a husky whisper that made his head spin as his back hit the wall. Or maybe it was the closeness of her as her lips brushed against his.

Steve's face flushed red again as he tried to formulate his thoughts into some semblance of sense.

"Will you change me?" he mumbled, a slight quaver cracking his voice.

"Will I change you, what?" Amanda cooed, urging him to say the word he was trying to avoid.

Steve's eyes sank to the ground as he started to ask again, but he was shocked into silence as the hand on his chest flicked up under his chin. With a firm grip, she lifted his gaze to her face again.

Her eyes caught his and held them transfixed as she spoke again, her voice taking on an edge.

"When you ask mommy for something, you look me in the eyes. Understand?"

The words carried an unspoken threat that made Steve swallow past a sudden lump in his throat.

"Yes, mommy," he squeaked, unable to look away.

Just that fast Amanda is all smiles and cooing again.

"Good boy," she said, the praise making the butterflies in his tummy flutter even harder. "Now try again, sweetheart."

Steve took a deep breath, his eyes trying to hold hers but flitting about nervously despite his obvious efforts.

"Will you change me, mommy?" The words were barely a whisper.

"What's the magic word?" Amanda teased, her hand giving an especially firm rub to his aching shaft.

"Please?" he groaned, his hands fluttering uncertainly by his sides.

"Of course, pumpkin, but only because you asked so sweetly."

She gave his cock one more good squeeze before taking him by the hand and leading him to his unmade bed with a coy smile.

Steve's heart was in his throat as she threw back the covers and straightened his sheets to make a nice, flat changing area. Her eyes picked up a few white-ish stains almost immediately, a well groomed eyebrow arching up at him. Steve blushed furiously, his eyes trying to find anywhere else to look.

Amanda chuckled again before walking over to her gym bag and dragging it to the foot of the bed. With a quick zip she opened the contents for him to peek at.

At first there wasn't much to see, but when Amanda pulled a pink blanket off the top to flip open as a changing surface and he saw what was beneath his cock jumped inside his nappy.

Aside from all the regular items you might see in a change kit, like powder and wipes, there were also quite a few more adult-oriented toys. Steve recognized a small set of transparent jelly anal beads and a smallish plug of the same material, a set of pink leather bondage cuffs, several remote controlled egg vibrators, and a pair of extremely large dildos that looked, and probably felt, real.

Deeper in the bag he spotted what appeared to be a hot water bottle with a hose wrapped around it, a pair of plastic underpants, and a medium-sized school paddle that looked made out of clear plastic. The paddle had small holes drilled in the four corners and one big hole right through the middle.

Reaching into the bag, Amanda grabbed the paddle first and placed it next to the changing blanket, her eyes watching him surreptitiously as she did so. She must have noticed his nervous fidgeting as he looked at the wicked looking implement.

"What's the matter, baby?" she said, pausing to run a finger along his jawline. "Never been spanked before?"

Steve shook his head a little, his eyes still glued to the paddle.

"That's okay, sweety," she cooed. "The first time is always the hardest, but as long as you're good today you won't need to worry about that little guy. Just think of him as a reminder to be on your best behavior, alright?"

Steve nodded uncertainly. He wasn't thrilled about the idea of having that thing roast his backside, but he also wasn't sure he would say no if she decided to use it on him. For someone who tended to avoid pain and conflict like the plague, Steve found himself strangely drawn to the object. It looked like it would hurt tremendously, but what would that pain be like?

He knew that some people enjoyed the act, but weren't those more like "pleasure spankings?" Mommy, er... 'Amanda,' he mentally corrected himself, had made it seem like having that paddle used on him would be for punishment. He wondered how long she would use it on him. How hard would the swats would be? Would she listen if he begged her to stop?

His thoughts were interrupted when he heard Amanda clear her throat, an obvious attempt to get his attention back where she wanted it.

"Go grab mommy a nice new nappy to change you in to, okay baby?" Reaching a hand out, she grasped his wrist in a light grip and used it to help propel him towards the closet in little shuffling steps. Her other hand suddenly smacked into his wet diaper with a muted "thud," making him yelp in surprise and hurrying him on his way.

"Quickly, little one," she said in a sing-song voice. "Mommy doesn't have all day to play."

Steve's self-consciousness reached new heights as he took the few steps across the small room, his diaper crinkling wetly with each footfall. It didn't help that Amanda's stare was almost a physical sensation on the bare skin of his back.

He opened his closet and grabbed a fresh change out of the pack that Amanda had bought him yesterday. The only other diapers missing were the one he was wearing and the one he'd worn to dinner. The thought of having so many to wear in the future sent a little thrill through his tummy.

When he turned around, that feeling intensified as he saw the look in her eyes. It was the same kind of hunger they'd held in the parking lot. The kind of gaze that made him feel hunted, but in an exhilarating kind of way that sent electricity tingling down his spine.

Steve licked his lips nervously as she beckoned him back with a single finger, a mischievous smile playing at the corners of her mouth.

"Good baby," she cooed as he handed her the fresh nappy. His painfully hard erection strained as it tried to pry free of its damp prison.

Setting the diaper to the side, she grabbed him by the hands and moved him to sit on the changing surface so his body was perpendicular to the bed, then leaned him back until his head nearly touched the wall on the other side.

Next she grabbed each leg under the knee and lifted them onto the bed so that he looked like he could have been in one of those hospital beds with stirrups. Steve's legs naturally folded open in the new position, and he knew that as soon as she opened his diaper, he'd be on full display to her eager gaze. A wave of goosebumps ran over his skin.

"It's okay, baby," Amanda said warmly, rubbing a warm hand over the skin of his thigh. "Just let mommy take care of you. You'll feel so much better in a fresh nappy."

Her hand ran over the pulsating bulge hidden beneath. "I'm not entirely sure what to do about this little problem, though." She chuckled as he humped up into her hand again, desperate for stimulation. "I guess we'll just play it by ear?" Her tone made it clear she already knew exactly what she wanted to do.

With Steve centered over the changing mat, Amanda took a moment to drink in the sight of her new toy. What little body hair he had was sparse and fair enough to almost go unnoticed. She smiled down at him warmly as she placed her hands on his knees and gently ran them up to his hips, where the velcro that held his nappy on was.

"While I have your undivided attention," she said casually as she pulled one side open, "I thought it would be a good idea to go over a few of the rules and expectations you'll be expected to follow as long as you decide to keep playing our little games."

"Rules?" he asked with a squeak as the ripping sound of velcro coming undone filled the room and the other side popped open. He felt the damp material start to pull down, exposing him to her eyes.

"Yes, sweetheart. Rules," she said firmly. "Even in the short time we've known each other, I feel like I've gotten a pretty good read on you, and I think a little structure is exactly what you need in your life."

Steve tried hard to listen to what she was saying, but the sensation of suddenly being naked was distracting as his diaper fell the rest of the way open. He chanced a glance down at Amanda, but she was all business as she reached for the box of wipes from the gym bag.

Popping the top off with a practiced flick, Amanda pulled a small handful of wipes out of the box before closing it and tossing it back in the bag.

Grabbing a wipe off the stack, she gripped his throbbing cock with her free hand, moving it this way and that to look him over.

"Is this what I think it is?" she asked, pointing with the wipe at where his pubic hair was matted down.

Steve blushed. He hadn't been able to help himself. After she'd left the night before, he'd woken up twice in the middle of the night with inconsolable erections. The only cure had been to, ahem, "handle" them. The whole time he'd been thinking of the way her hands had felt on his skin. The way her voice made him feel when she praised him for being a good boy. He even imagined that scary feeling he got in his tummy when she frowned or took a hard tone with him.

"Yes, mommy," he said shly.

Amanda sighed. "I suppose I should have been more clear last night. When I said that you needed to ask permission to cum, I didn't just mean when I'm here."

Steve started to protest, but her hand gave his shaft a long, firm stroke, and suddenly he couldn't remember what he was about to say.

"I find that little boys always tend to behave better if their mommy is the only one allowed to tend to their 'needs.' Is that a problem?" she asked. Her tone made it clear what answer she expected.

"No, mommy," Steve whimpered as her hand gave his aching member another long rub.

"Good boy," she cooed, her hand starting to work more vigorously on his throbbing member.

Steve's breath started to get more ragged as the pleasure quickly built up in him. His head swam with the sensations. Mommy's skilled hands were too much for him to resist as they kneaded and caressed his sensitive skin. He could feel himself nearing climax at a frightening pace. His body tensed up, only moments away from a brain shattering orgasm, when suddenly the feelings stopped.

Steve's eyes shot open and he gulped in a breath like he'd just been doused in ice water. The feelings of pleasure plateaued just below the point of no return as he humped fruitlessly at the air in a failed attempt to push himself over the edge. Desperate and bewildered, he looked down at Amanda.

She stared back up at him, an eyebrow cocked and a small frown on her lips. "You were about to cum without asking permission, weren't you?"

Steve realized that's exactly what had been about to happen. The tingles had been so delicious and overwhelming that he'd already forgotten about needing to ask for it.

"Yes, mommy," he said with a blush, looking away as he did.

Amanda gave an annoyed sigh. "It looks like you need a lesson in what happens if you forget to ask permission."

Steve's eyes flicked nervously to the paddle, but Amanda ignored it, and his cock, as her hands began to clean him up in earnest. One soiled baby wipe turned into two, then three, and finally four as she finished cleaning his front and backside, lifting his legs slightly to run the last cloth between his bottom cheeks and making him blush profusely.

Steve's cock stayed rock hard throughout, but Amanda studiously ignored it. Reaching back into the gym bag, she pulled out a tiny pink pouch and poured the contents out on the bed next to him.

It looked like a tiny suitcase lock, a series of pink plastic pegs and rings, and one large piece that sort of resembled... a penis?

"Do you know what this is?" Amanda asked as she started to fit the pieces together like a jigsaw puzzle.

"No, mommy," he shook his head, suddenly feeling uneasy.

"Have you ever heard of a chastity belt?" she asked.

"Yes, mommy," he nodded, a sinking feeling entering his stomach.

"Well this is called a 'chastity cage,' and it's designed for little boys instead of little girls." Amanda started to grab the rings and place them beneath his scrotum. It took him a moment to realize she was trying to get the size right. There were over half a dozen rings to choose from, but she finally settled on the second to smallest one.

"This might be a little tight, but it should keep you from getting yourself into any trouble until mommy gets back."

Steve chewed his bottom lip as he watched the device getting assembled. First the ring went back under his scrotum and closed over the top of his shaft, making a circle with a single hole at the top for a peg. She chose a smaller peg and pushed it through the hole, holding the circle closed. She started to grab the last penis-shaped part, but with his erection still at full mast, there was no way it was going to fit in that little piece of plastic. Amanda took a firm grip on the shaft with one hand and an overhand grip on the head of his cock with her other.

"This is going to be a little... unpleasant," she said, looking up at him briefly.

It didn't take him long to figure out what she meant as she dug the tip of her thumbnail into the head of his penis, just above the foreskin. Steve's whole body jolted like he'd been shocked with electricity and he gave a little cry of pain. His hands shot down to protect himself, but she caught his eyes with a cold stare that promised worse if he interfered and his hands froze where they were. Still, as she applied ever more pressure, Steve's hands fluttered around, desperate to stop the stabbing pain in his cock.

The treatment had the desired effect, though, and in less than a minute Steve's raging erection had shrunk down to almost nothing. Steve gave a sob of relief as she released his poor manhood from her vicious grip.