Dinner Date with Mommy Pt. 01

Pulling it down, she realized with some dismay that it barely covered her backside while she was standing upright. If she needed to bend over, it would ride up far enough that you'd be able to see just about everything, and the panties her Mommy had picked out would do little to obscure the fact that she'd been given a good spanking recently. Her cage would also be on display, a fact she was sure hadn't escaped her Mommy.

There was no sense in arguing, though. She would just get herself into trouble again, and the last thing she wanted was to get spanked in front of the man she was supposed to cook dinner for tonight. That would be a humiliation Sophie wasn't sure she was ready to deal with.

It didn't take her long to finish pulling on the little clothing remaining, garters and socks slipping on easily, though the panties did feel a little snug over her sensitive coinpurse, and they kept riding up to give her a wedgie that she had to continuously work to keep from exposing her bruised backside.

Looking down beside the dresser, she saw her Mommy had also picked out a cute little pair of cream colored flats for her to wear. Stepping into them, she looked at herself in the mirror above the dresser, taking in the full view for the first time. Aside from her slightly wet and wild hair, you'd have been hard pressed to find a better picture to put in the dictionary next to the word "sissy".

Taking one last look to make sure she hadn't forgotten anything, Sophie walked to the door, sticking her head out into the hallway.

"I'm ready, Mommy," she called out, listening hard for a response.

"I'll be right up, baby girl," she faintly heard her Mommy say from downstairs.

Ducking back into the room, Sophie looked around, making sure there was nothing out of place before taking up position to wait by the dresser. It was only a few seconds until she heard her Mommy's footsteps coming up the stairs. She took a deep breath, hoping her Mommy would like what she saw.

Sophie laced her fingers, fidgeting nervously as her Mommy came around the corner, now wearing a very flattering floral sundress. She stopped dead in her tracks when she saw the sissy in her pretty pink dress for the first time, a smile blooming on her face.

"Oh, sweetheart," she said, voice airy, "It's perfect."

Sophie blushed at the compliment, dropping into a cute little curtsy so she wouldn't have to meet her eyes. "Thank you, Mommy," she mumbled shyly.

Her Mommy took her time strolling across the room to her, admiring the way the dress hugged her tightly in all the right places. It was ever so slightly shorter than she'd intended it to be, but as she looked her baby girl up and down, she decided that was more of a happy accident than anything else.

"I could just eat you up," she said with a wicked smile as she slowly circled the scantily clad sissy, lifting the dress in the back to see the way her panties fit, the silky material snugly gripping her bottom and accentuating the fullness of her backside. "Victor is going to love you in this."

Sophie's mouth went dry. She'd really been trying not to think about the fact her Mommy wasn't the only one who'd be enjoying the view tonight.

"Now," her Mommy said, "Let's finish getting you ready so you can go start dinner."

Grabbing Sophie by the arm, Mommy moved her so she was facing the mirror above the dresser. Moving off to the side, she grabbed a slightly too-short chair and set it down behind Sophie, who carefully lowered her still sore bottom onto the hard wood of the seat. Opening up one of the dresser drawers, her Mommy pulled out a heavy old hairbrush that doubled as one of her favorite spanking implements and a medium length of light pink ribbon.

Using firm hands, Mommy ran the brush through Sophie's hair for a minute or so until it lay perfectly flat, then grabbed the ribbon and used it to tie through Sophie's hair, creating an adorable little bun on the back of her head with highlights of the ribbon poking through in a tight pattern that ended in a bow reminiscent of the ones on her socks.

Sophie watched in quiet amazement as her Mommy worked her magic. She always enjoyed doing Sophie's hair, and Sophie was happy to have her do it. It was one of the few rituals they had fallen into that they both seemed to like.

With a few more tweeks, she finally seemed satisfied with how it looked. Nodding in approval, the corner of Mommy's mouth quirked up in a little smile as she looked over her handiwork.

"Alright, sweetie," she said, gently squeezing Sophie's velvety smooth shoulders as she drew the sissy to her feet, "Let's get your other end ready too."

Sophie nodded meekly as her Mommy opened another dresser drawer. Inside was an assortment of anal toys that would make a professional dominatrix jealous. Every size, shape, and material you could think of was represented in some way. Taking a moment to think it over, Mommy grabbed a rather large cock-shaped buttplug. The material was similar to many of the sexflesh style toys she was so fond of, and the way it was tapered would ensure it stayed firmly seated in Sophie's bottom while keeping her ready for something larger should the need arise. Grabbing a small bottle of lube with a pump nozzle, she seated herself in the chair Sophie had just vacated.

"Come on, baby girl," she said, patting her lap, "Time's wasting."

Taking care to keep her dress smooth, Sophie knelt beside her Mommy and gently lowered herself over her lap.

"Good girl," Mommy said, gently rubbing and patting her sensitive bottom before lifting her dress and sliding her panties down to the middle of her thighs.

Sophie could feel her Mommy shifting around, the sound of lube being pumped and spread across the large toy loud in the quiet room. A few moments later she felt her Mommy's hands prying her abused cheeks apart, lube-slickened fingers working over her tight hole for a second before she felt one start to push inside. Sophie whined softly at the sudden insertion, her Mommy ignoring her as she added another finger. Twisting and thrusting ever deeper, she worked the reluctant rosebud open to take the large toy.

Sophie licked her lips as her Mommy's strong fingers continued their uncompromising exploration, her vigorous digits occasionally sliding over the tickle spot deep in her bottom, making her groan and push her bottom up for more. The movement didn't go unnoticed.

"Is my baby girl feeling like a needy little slut today?" Mommy teased her, fingers purposely fluttering over the sensitive area for a moment, eliciting more moans from the sissy. "Don't worry, I'm sure we'll find some way to scratch that itch for you tonight."

Removing her fingers, Mommy pushed the toy up to her entrance, the head prying her tight hole open ever so slightly.

"Relax, sweetheart," she said, one hand working the toy in little by little as the other alternated prying her cheeks apart to make the insertion a little easier.

It wasn't the biggest toy her Mommy had used on her, not by a long shot, but it still felt huge as her bottom reluctantly opened up to accept the rude invader. Taking shallow breaths and whining occasionally, Sophie did her best to keep her bottom relaxed as her Mommy finally pushed the toy in past the widest portion and her bottom started draw the large plug in on its own. With a whimper, Sophie felt the toy slide home, the base pressing firmly against her bottom cheeks.

Grabbing the base in a firm grip, her Mommy slowly pulled the toy back out, making her gasp as the widest part popped back out. Giving the clean plug an appraising look, she decided the slut had done a good enough job getting herself cleaned out. Pressing the toy back against her tight hole, she gave it a hard push and twist, forcing it in hard enough to make Sophie cry out.

"There," she said, pulling Sophie's panties back up so they would help hold the toy in place and patting her bottom reassuringly, "That wasn't so bad, was it?"

"No, Mommy," Sophie replied, voice timid as she pushed herself back into a kneeling position, shifting uncomfortably as she became accustomed to the lewd intrusion, her bottom pulsing seemingly at random around the thick toy.

Suddenly her Mommy tsked, drawing Sophie's attention to a shiny little trail of cum just below the hem of her sundress that must have leaked out of her cage while her Mommy was getting her ready.

"Clean that up," she said, voice brusque.

"Yes, Mommy," Sophie squeaked, quickly leaning in to lick the mess off of her thigh, the salty taste extremely familiar to her. She was always required to clean her messes with her tongue after being milked, and after so long in chastity, it seemed like she leaked more now than she had ever squirt as a boy.

Leaning back, Sophie allowed her Mommy to inspect her cleanup job. Nodding in approval, her Mommy stood from the chair, straightening her dress as she did so.

"Alright, sweetie, I'd say you're just about ready for our little dinner date." Her Mommy looked at herself in the mirror, smiling confidently at what she saw. "Now get to the kitchen and get to work. Our guest will be here in about an hour."

"Yes, Mommy," Sophie said, standing up and giving her Mommy a meek curtsy before shuffling out of the room, her discomfort evident as her tight little hole slowly adjusted to the toy.

Watching her dolled up sissy leave out of the corner of her eye, Amanda let a sly smile touch her lips. She had high hopes for their date tonight. The smile turned into a wicked giggle as she remembered the picture of Victor she'd showed Sophie and the poor girl's frightened reaction.

Oh, yes, tonight was certainly going to be special.

End of Part 1

Thanks for reading, and remember to check out my other dirty stories! Check back soon for more, and don't forget to share the love, you filthy pervs. <3

If you find any typos or big mistakes, I always appreciate the feedback so I can make the story just a little bit better.

Meeting Mommy (Femdom/sissy fun) - Prequel to Dinner Date with Mommy: https://www.literotica.com/s/meeting-mommy

Dinner Date with Mommy Part 2:

Dinner Date with Mommy Part 3: