Dinner Date with Mommy Pt. 04

Disclaimer - This story includes the following themes: Femdom, sissification, feminization, forced-bi, forced cum-eating, butt plugs, anal play, strap-ons, spanking, humiliation, CBT, chastity, and domestic servitude.

If these themes do not interest you, then this story isn't for you, sweetheart.

For everyone else...

This is it. What you've waited for. The payoff after the setup.

Part 4 returns us to the present as Sophie wakes from her dreamy nap. The action is hot and heavy throughout this fun little story about a sissy's first time with a real man under the watchful eye of her strict Mommy.

If you haven't read any of the previous stories, you can check them out in my profile.

Enjoy!

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Part 4

Sophie's body was still buzzing pleasantly from the wine her Mommy had given her at dinner. With her head pillowed against something warm and soft, and a strong arm wrapped around her, she felt safe. Sophie snuggled closer to her Mommy as she gave a contented sigh.

The sound of her Mommy's phone ringing almost drew Sophie fully awake, but she wasn't allowed to answer her Mommy's phone so it wasn't a sound that she had learned to associate with needing to be instantly alert.

As such, it took her somewhat by surprise when her Mommy answered that phone quite a distance further away than Sophie had thought she was.

"Hey, this isn't an opportune time for me. Is it important?" Amanda said by way of answering her phone.

Sophie's sleepy eyes refocused as she sat up and looked toward her Mommy, but there was something big in the way. Sophie's eyes started to trace up the object in her way as her Mommy stood up on the other side of it.

"Alright," Amanda said, suppressing a sigh. "You've got 15 minutes."

When Sophie's gaze finished tracking upwards, she almost wet herself when she saw a giant man's face staring back down at her.

"Victor!" she squeaked, her voice breaking. How had she forgotten he was there?

"Morning, kitten," he said with a grin. "You look a bit like an angel when you sleep, did you know that?"

Sophie ducked her head and felt her entire face flush bright red.

Amanda gave the two of them a knowing look out of the corner of her eye.

"Make that 20 minutes," she said, her voice taking on an amused quality. Amanda put her hand over her phone for a moment and leaned towards Sophie, fixing her in place with a stare.

"Remember what I told you earlier," she said with a deliberate nod towards Victor. Her gaze made it clear that the consequences for disobedience would be more awful than anything she could imagine. Maybe her Mommy would finally make good on her threat to connect her "shock box" to one of the metal sounding rods she regularly stretched Sophie's poor clitty out with. The thought made Sophie shudder.

Amanda turned and left the room, and a few seconds later Sophie could hear the door to her office close.

Suddenly she was alone with Victor, and his ogling was making her feel anxious.

"What was that all about?" Victor asked with an off-handed gesture towards Amanda.

Sophie licked her lips, the moisture deserting her mouth.

"Mommy wanted me to tell you that tonight, if it's okay with you, I'm..." Sophie trailed off, her throat choking on the words.

"You're supposed to what?" he asked, looking at Sophie curiously.

Sophie took a shuddering breath and just blurted it out as fast as she could.

"I'm supposed to call you Daddy, tonight!"

Scarlet suffused her face all the way down through her neck as her voice echoed off the hard walls. Sophie cringed. That had been much louder than she'd intended. It was a good thing her Mommy had closed the door to her office.

Victor's eyebrows shot up.

"Wow, really?" he asked, his voice uncertain. "I mean, I'll be honest, I've had a few women call me Daddy before, but never a... well, you know."

"A sissy," Sophie finished quietly, a wave of shame rolling through her at the words.

"You say it like it's a dirty word," Victor said.

"Isn't it?" Sophie asked, her tone unexpectedly bitter. Here she was, all dolled up and ready to be used for only her-Mommy-knew-what, and this was the man who was going to be helping her do it.

"I don't think so," Victor said, the words shocking Sophie a little. "I think you and Amanda are good together."

"Really?" Sophie asked, her eyes finding his again.

"Really," he said with a smile. "And it looks like you enjoy most of the games you two play together or you wouldn't stick around. You do enjoy them, right?"

"Well... yeah," Sophie admitted softly. A little throb radiated through her bruised coinpurse from where her Mommy had used the strap on her for being difficult. She'd beat Sophie's sensitive little sack until she was a crying wreck.

"Most of the time," she added quickly.

"Then it seems to me," Victor said, he voice drawling a touch, "Worrying what other people think about your relationship is kind of silly, don't you think? Most men would kill to be with a woman that beautiful and kinky."

Sophie still felt a little awkward, but Victor's words touched on something that she'd often thought about. She never knew how people would react to the lifestyle they'd chosen if they found out about it. Would they shun her and Mommy? Call them freaks? Out them both to the public?

However, his words also skimmed over the reason Sophie had stayed, despite that fear. She did have a relationship with her Mommy, and it was good. Every step Sophie had taken down her path to sissyhood had been with her Mommy at her side, encouraging her at every turn. Sophie shifted on her still-red bottom from where she'd been given a hard spanking earlier in the day. Sometimes that encouragement had been quite vigorous.

"So you don't think it's weird?" Sophie asked, her voice hopeful.

"Of course I do," Victor said with a laugh, making Sophie blush and look away.

Reaching a big hand down, Victor raised her face to him again. It was something her Mommy did all the time, though she wasn't prepared to feel the same kinds of butterflies fluttering in her tummy now that it was Victor doing it.

"But I also know that 'weird' just means 'new to me.' So why don't you tell me a little bit about it and then it won't be so weird anymore?" Sophie suddenly noticed what a deep shade of green Victor's eyes were.

Sophie swallowed at the sudden lump in her throat and gave a shallow nod. "Okay."

"Ah ah," Victor said with a little finger waggle. "That's 'okay, Daddy,' to you, kitten."

Sophie felt herself blush all over, but managed to hold his gaze as she answered again.

"Okay, Daddy." It was barely a whisper.

"Good girl," he said, leaning back into the couch with a sloppy grin on his face. His praise made Sophie feel unexpectedly self-conscious, her hands starting to play nervously with the hem of her dress.

"Now what's this 'domestic discipline' thing Amanda keeps telling me about?" he asked.

For the next few minutes Sophie answered a slew of questions from Victor, each time remembering to politely call him Daddy. She expected the oddness of the word to fade after the first couple of times she used it, especially since her Mommy had tried to prepare her for it.

Sophie had watched hours upon hours of sissy hypno videos while tied up tight, a fucking machine she'd had to call "Daddy" working relentlessly on her pussy and forcing her through countless sissygasms. But each time she used the title for Victor she had to resist the urge to look away from his gaze as the sound of it made him smile.

Sophie explained how her Mommy really did paddle her bottom if she misbehaved and, yes, it really hurt. Victor insisted on her standing up and showing him her bruised bottom again.

"And she did all of his in less than five minutes with a wooden hairbrush?" Victor asked as his touch wandered across some of the darker bruises with his soft but rugged hands. It felt like someone had used a hundred bottles of lotion on an elephant's hide.

Sophie shuddered at the sensation as she nodded, "Yes, Daddy."

"And what about this?" Victor asked, his voice playful as he grabbed hold of the plug's base and gave it a little wiggle.

Sophie squeaked at the feeling, but managed to stay quiet otherwise.

"While you were getting some beauty sleep your Mommy and I snuck off into your playroom," Victor continued, his hand twisting and pulling on the plug as he spoke. "I have to say, I'm skeptical that some of the toys she showed me actually fit, if you know what I mean?"

Sophie blushed. There was no telling the kinds of stories her Mommy had told, and they would likely all have been mortifying for the poor sissy. "It's not always easy, but I doubt she showed you anything that she hasn't had buried all the way inside of me."

"So you really can take the... what did she call it? 'Ego-breaker?'"

Sophie flushed an even darker shade of red.

"Yes, Daddy, I can," Sophie said quietly, biting her lip to fight off a moan as the plug in her bottom rubbed against her tickle spot while Victor continued to play with it.

Her Mommy had a flair for the dramatic, but the dildo Victor was talking about had been appropriately named. At a hefty 14" long and thicker around than a tin can, it had taken her Mommy months to work her up to it. When Amanda had begun Sophie's anal training the going had been slow.

They'd started with fingers and small plugs, but the stretching process still required a lot of time for healing. During their downtime Sophie had worn a special dilator lubricated with soothing cream for several hours a day. It had helped speed up Amanda's efforts considerably. Instead of having to wait for up to a week for her to recover, they only needed a day or two before Sophie's sore little hole was usable for another round of grueling strap-on play. It did little to keep Sophie from bawling like a baby the next time her Mommy increased the size of her toy and proceeded to bury it up her sissy pussy, though.

The night her Mommy had first used the Ego-breaker on her had been just a little over a month ago. Sophie had been being difficult all day long. First she'd committed a cardinal sin by balking at what her Mommy had picked out for her to wear while "company" was over, regardless that "company" meant another Mistress with her own sissy in tow.

Her refusal had, of course, earned her a harsh, immediate punishment spanking from her Mommy. A hand, paddle and strap had all made intimate acquaintance with her hindquarters in short order. Sophie was left a sobbing mess as her Mommy had pinned her babydoll dress up to expose her punished bottom. Then Amanda stuck her nose into the corner to think about her behavior, with strict instructions not to rub her burning backside, until their company had arrived. When they finally arrived, their visitors had then been invited to inspect Sophie's crimson backside at their leisure, something they'd gladly taken advantage of.

Sophie's mind skipped over the rest of that encounter, still not ready to really contemplate the things she'd been made to do that day.

However, despite being unable to sit comfortably for the rest of the day she was apparently too stubborn to learn her lesson. Later that night she'd also complained about how swollen her little sissy grapes were, and begged her Mommy to be allowed to cum.

Normally that kind of pleading would have been met with little but teasing denial, but it had been a big no-no at the time as Sophie had been in the process of learning to cum from nothing but prostate stimulation.

After her Mommy had finished giving Sophie her second good spanking of the day, this time with a hairbrush and over a dozen licks from a junior cane that had Sophie's feet drumming wildly against the floor, Amanda had grabbed the crying sissy by her ear and dragged her towards her bed.

Sophie had been made to kneel up on her bed, her striped, crimson bottom sticking over the side as her Mommy had left the room for a few minutes. When she'd returned, Sophie had nearly had an anxiety attack when she saw the massive toy strapped to her Mommy. Of course, the elbow-length PVC gloves Amanda had been wearing hadn't done much to sooth the sissy's fears, either.

"I'm not sure what's gotten into you today, baby girl," her Mommy had said, voice stern as she took up position behind the exposed sissy. "But I'm going to put a stop to it right this second."

A long, tearful stretching session had commenced as her Mommy had quickly progressed from fingering her sore bottom hole to working most of her hand into it. Sophie could remember clawing at the covers on her bed as her Mommy's hand had finally popped past her reluctant entrance and been drawn in even deeper. She'd felt so full she thought she might burst!

Pulling her hand back out with a popping sound, Amanda had lined the toy up with Sophie's winking pussy and started to drive it in. Grabbing Sophie by the hip with one hand, Amanda had used the other to keep the toy pressed against Sophie's straining hole as she methodically worked the head of the massive cock into the crying sissy.

"I warned you, sweetheart," her Mommy had scolded her as the giant toy began to slide into her tight passage. "It's been less than a week since Mommy milked you, and you're already complaining about needing another release."

Amanda had swatted Sophie's hand away as it fluttered around behind her, desperate to stop the progress of the cruel invader, but not daring to actually touch her Mommy.

"Well, if sissy needs a cummy, then sissy can learn to cum like a good girl," Amanda had said, starting to pump what little of the toy she'd crammed into Sophie's throbbing hole back and forth.

Somewhere in the back of her mind Sophie felt the plug in her bottom being played with, making her moan like a slut as her clitty gave a jump in her cage at the memory.

The session had taken almost an hour of constant, tearful work as her Mommy switched between the big dildo and her gloved hands. The two tools together did an admirable job of stretching the poor sissy out until Amanda had finally been able to press her hips into Sophie's red, miserable bottom.

"There," her Mommy had cooed as she ran a soothing hand over the crying sissy's back. "All the way in. Mommy's so proud of you for taking the whole thing, baby girl."

Sniffing back tears, Sophie had remembered her manners. "Thank you for teaching me to be a good sissy, Mommy."

"Oh, no, pumpkin," Amanda had said with a chuckle as she pulled the toy out a hair and slowly pushed it back in. "We're not done yet. This lesson is only just beginning."

Ten minutes later, Sophie wailed her way through her very first prostate orgasm. Not the kind that makes a sissy leak a little bit in her cage, but the kind that makes her shoot her cummies almost as hard as a real climax. Amanda didn't stop as she held a little glass under the sissy's cage and caught Sophie's mess in it, though. She had worked up a good pace, leaving about half the dildo in on each thrust as her hips slammed into Sophie's aching backside time and again.

Five minutes later, Sophie cried her way through her second prostate orgasm. Another ten minutes after that and her entire body trembled uncontrollably as her Mommy pushed her over the edge one last time. Sophie gave a keening wail as her Mommy buried the toy up into her abused hole one last time, forcing what little cum was left in her deflated sack to dribble out weakly.

Satisfied that Sophie had learned her lesson, Amanda had pulled the toy out with an unceremonious "plop" sound. Sophie remembered the way her pussy had spasmed erratically in the absence of the huge invader as her Mommy laughed at how "hungry" her little hole still looked.

"I bet you could still take quite the pounding if I felt like giving it to you," her Mommy had said, making Sophie whine in fear.

Amanda had then produced a half-full shot glass from behind Sophie. It looked like even with as hard as she'd been pounding Sophie's poor bottom hole with the huge toy, she'd still managed to catch most of the sissy's cummies in it. Not willing to chance further punishment, the abused sissy had obediently opened her mouth as her Mommy fed her every drop of the sticky, white liquid.

"But..." Amanda trailed off, a sly look on her face as Sophie finished swallowing her cum and opened her mouth for her Mommy to inspect. She ran a neatly manicured finger in a light circle around the sissy's lips. "I think it's time Mommy had some fun, don't you?"

Sophie had agreed, her voice timid as her Mommy planted a little kiss on her lips and stripped down until she was fully nude. Laying on the bed, Amanda had spread her legs wide to afford the poor sissy access to eat her pussy until she was given permission to stop.

Using the giant toy on Sophie must have been particularly exciting for her Mommy, because Amanda had the red-eyed sissy eat her out for over an hour before calling it quits on her fourth orgasm. It hadn't been the longest pussy worshiping session Amanda had ever put the sissy through, but it was the first time after such a severe punishment, and Sophie had been sure to show her Mommy what a good sissy she was going to be for her.

Sophie could still remember how miserable she'd felt, her bottom throbbing, inside and out, with her face buried in her Mommy's soaking pussy. The sorry sissy hadn't objected to anything her Mommy had picked out for her to wear since that incident, and had gone another three days without complaint before her Mommy had let her out of chastity.

Of course now she was rarely allowed to cum without some sort of toy or her Mommy's fingers working busily over her prostate, and she often had to settle for half-ruined orgasms as her Mommy stopped stroking her clitty just before she came, instead forcing the sissy to cum through anal stimulation after bringing her to the edge.

Regardless, Sophie still found herself face down, locked in chastity at least a half dozen times a week as her Mommy continued to instruct her on the proper way to cum like a girl, and the Ego-breaker had made a few appearances in that endeavor as well.

"Earth to kitten," Victor said playfully as he reached around and waved a hand in front of her eyes.

"Sorry, Daddy," Sophie squeaked as she blinked herself back to reality and looked over her shoulder at him. "I got a little distracted."

Victor chuckled, nodding downwards. "Must have been a hell of a distraction to make you leak like that."

Sophie looked down between her legs and blushed furiously when she saw a long, clear string of pre-cum hanging from her cage. Without thinking about it she reached down and caught the slippery substance on her finger, then brought it to her mouth and sucked it clean.

"So," Victor said, his eyes watching her movements closely and his voice taking on a mischievous quality that made Sophie's tummy flutter nervously. "Your Mommy is right, isn't she? You really are a cum-drinking, anal-loving, sissy slut, aren't you?"

Sophie covered her face with her hands. She felt like she might die of embarrassment as his big hands closed on either side of her waist, pulling her back towards him. She obeyed his wordless command, shimmying back until her legs hit the edge of the couch. However she wasn't prepared for Victor to actually lift her up in that position. It was like she weighed nothing in his strong arms as he pulled her back and sat her down across his lap like a princess, making her squeak when her bottom came into contact with his broad leg and the plug was pushed just a little bit deeper, causing her to wriggle.

"Well?" Victor pressed, his eyes searching hers as she licked her lips. Her clitty gave a hard throb in its cage.

"Yes, Daddy," she whispered, unable to look away.

Victor's hand moved up to her mouth and traced a thumb along her lower lip. "And these are the plump little cock-sucking lips your Mommy bragged about so much."