Vanessa's Grand Finale

Sophie and I snuck into the Signature Grand Ballroom early the day of Kitty Van Look’s charity auction. It was pretty easy. We entered as part of the wait staff and found ourselves having access to the whole place. It was quite a place.

There were five different ballrooms of varying size, each one full of round tables. Basically it was place for a big wedding reception. Kitty was booked into the Signature Signature Grand, the biggest one of course. There was stage installed in this one. It was at the back of the room and was the kind you’d see in a convention. There was no backstage. You were either on it or off it. The room had exits in each corner. Two led to the main hallway. The other two, in the corners, led to a hallway where you could find a holding room, storage closets, and cleaning supplies.

“After we get the watch back we should just stay here. I bet it’s a fertile hunting ground,” Sophie said.

She was amped up. She could not wait to get some alone time with Vanessa tonight. Even though the public did not know who Sophie was, her beatdown by Vanessa had played millions of times over and over on television and YouTube. I didn’t even know what Sophie planned to do. I don’t think she did either.

I should point out that if you’re going to pretend to be a part of a giant wait staff at a reception hall, you should expect to set up chairs. Because that’s what I ended up doing for an hour. Sophie too. It didn’t matter really, as long as we get that damn watch back.

An hour before things were supposed to start Kitty showed up. The usually outlandish socialite looked elegant in a long flowy light green dress. It had one strap that went over the right shoulder. Her blonde hair was done up in some fancy style that I’m sure a woman could describe much better than I. But I can tell you this. She looked amazing. She was thin, and her dress showed off her small B cups, but they were still very inviting. As she walked past inspecting the room the Sophie wacked my shoulder.

“What are you looking at?”

“What? Nothing!”

Even if I had thoughts of making the moves on a wealthy socialite those were dashed once I saw Hans, her date for the evening. Hans was 6’3” and shoulders as broad as my legs were long. Which was fine. I’m just here for the watch anyway.

Soon enough the place was filling up with rich people looking to feel good about themselves by bidding on expensive things no one needed, ‘experiences’ they could all afford anyway, and most interestingly a date with Vanessa English,

After Vanessa sent her tweet that should be attending her old school rival started chatting her up about it. Vanessa had never come to this event before and here out of the blue was announcing her attendance? Had she gone through some sort of change of heart, Kitty wondered. Was the biggest snob in a school of snobs finally loosening up? Kitty needed to know. She called up her old classmate and the two chatted a bit. The call ending with Vanessa agreeing to be auctioned off for charity. An act that really stunned Kitty. Maybe the haughty ice queen had melted.

Of course you know better, right?

Vanessa had her own plans for the night. They included being seen with her new boyfriend Danny, another tall, handsome stud that came off the same rack as Hans at the boyfriend store. They also included humiliating Kitty at her own charity auction. Vanessa was really pleased with how she handled Tiffany Griffith’s humiliation and was going to duplicate it. And add to it. Tiffany just found herself having sex a with a fat sweaty slob. Okay so yes that was totally disgusting, but no one actually saw it happening. So she’d have to film it. And livestream it to the large screen set up on the stage (the one meant to show off the ‘experiences’ people were bidding for). And being naked was no big deal for Kitty. Everyone had pretty much seen her that way. So the best thing to do was to dress her. And what better way to dress that bitch that to put her in a little frilly sissy dress. A little one that wouldn’t even cover her ass. She picked out pastel blue. Same color as Vanessa’s dress in the seventh grade. And she’d need matching panties to go with it naturally. Pastel blue filly ones, like Vanessa used to wear but that had Kitty’s school nickname on them, “Itty Bitty Kitty”. Vanessa loved the idea of Kitty being caught in this ridiculous costume while be fucked by some sweaty, gross, hairy, slob. It would be a nice bit of **** from the “Princess Vanny” name she had to deal with in school. The thought was just too rich! Everyone seeing Kitty getting in the ass from some random fat, sweaty guy while wearing this weird little girl fetish dress. She’d never live it down, Vanessa thought. She imagined Itty Bitty Kitty trending on twitter. Her reputation ruined. Her ass violated. It was going to be so, so good. She put the dress and the panties in a bag, donned her best formfitting cream colored dress (a Charleston dress with short sleeves and ended just below the knee), long pearls, matching leather gloves and a little clutch purse, and headed off with Danny for the night.

At the ballroom I noticed the little tracker the old man had given us going off. Vanessa had entered the building. She sat the table in the front with Danny. There was to be the auction, then a dinner, and a cocktail hour. Vanessa noticed that the room was filled with people she couldn’t stand. Even Tiffany Griffith was sitting at a back table.

“So brave of her to be here after her shameful behavior,” Vanessa said to Danny who pretended to care.

I’ll spare you the details about the auction. I can tell you a lot of money was spent on some weird crap and extravagant trips and it was really boring for the most part. What mattered was us getting the watch. All night long Vanessa didn’t leave her seat. The bag with the dress for Kitty was in the holding room down the back hallway. It was a small room with a couch, some chairs, a coffee table in the middle, and a desk in the corner. But the watch wasn’t there. According to the tracker it was with Vanessa still.

“It’s in her purse,” Sophie said.

“Are you sure?”

“No, but there’s no other place it could be. And we know it’s at her table.”

“Okay, then I’m going in.”

I walked over to Vanessa’s table with a small serving tray and began gathering used dishes. Everyone ignored me as I went about my work. But when I got to Vanessa and made sure to accidentally knock her purse off the table. When it landed the clutch popped open and everything inside spilled out. Vanessa’s ID, credit cards, phone, and the watch.

“You clumsy idiot,” Vanessa said as I bent over, my ass in her face, as I picked up the purse.

“Sorry.”

I had the look-a-like watch I took from the old man’s store in my hand and quickly swapped it for the watch. I then quickly put everything back inside the purse and put it on the table before Vanessa could get a good look at my face.

“Wait a minute,” Vanessa said as I was walking away but I wasn’t waiting a second more. Then a hand was on my shoulder. It was Danny, Vanessa’s date.

“The lady said wait,” he said.

Vanessa picked up her purse and looked inside for a minute while I stood with my back to her. A few seconds later she said, “It’s fine, everything’s here.”

Danny took his hand off me and I gleefully went off to find Sophie.

“I got it! I got the watch back!”

Sophie threw her arms around my neck and pulled me in for a kiss.

“That’s amazing. You are so getting lucky tonight,” she said. “But first it’s time for some payback.”

“Not yet,” I said. “Let’s wait for the perfect moment. Let’s wait for when Vanessa gets auctioned.”

Sophie frowned. “Okay, fine,” she said folding her arms.

The night droned on. What it was getting through it. A total bore. But then it was Vanessa’s turn finally.

Vanessa had been totally bored too. She couldn’t care less about charity and she couldn’t stand most of the people in the room. Just before her time up on stage she decided maybe a little mischief would make the night go faster. She opened her purse and took out the dummy watch. Looking around she spotted a female server she thought it would be fun to make trip. She then pushed the button on the watch. And nothing happened.

“What the hell,” Vanessa said.

She pushed the button over and over. Nothing. Everyone kept moving. Time did not stop. Was the watch broken? Did that idiot break it when he knocked it on the floor? The more wondered about this the more frustrated she got.

It can’t be broken. Not now. She was so close. That bitch Kitty was going to get away and…

“And up next Miss Vanessa English,” Kitty said from the stage breaking Vanessa thoughts. The crowd applauded as Vanessa got up and headed up on stage.

“Vanessa English is an old friend of mine. She’s known for her taste and signature style AND for one night she’s all yours!”

Kitty stood at a podium while Vanessa was across the stage standing a bit awkwardly.

“Let’s get the bidding going at one thousand dollars,” Kitty said. A hand quickly went up.

As the bids went higher and higher Vanessa’s vain ego filled up and she began to pose and parade about on stage. Kitty loved it. The audience ate it up. She had one hand on her hip and one on her head. She’d lean back and stick out her chest, one that always worked.

In the back Sophie was about to throw up. “Now?” she said.

“Now.”

Vanessa was still posing on stage when everyone fell silent. Kitty looked over at Vanessa and saw her dress was missing. Her eyes widened as she looked at her former classmate, who completely unaware of her situation. Any why was she unaware? Should she have felt a draft or something? Well it’s because Vanessa English was wearing more shapewear than anyone had ever seen.

Still in her shoes and white stocking, Vanessa was also wearing a beige long line panty girdle that went from the top of the ribcage to just above the knee. One top of that was a waist cincher, and to top it off a thick sturdy bra that covered everything.

Vanessa looked like she was wearing a suit of fat busting armor.

Kitty couldn’t resist. “Vanessa, do a turn for us please.”

Vanessa happily complied. And when she turned around everyone could see the padding sewn into the seat of the panty girdle, giving Vanessa the illusion of an ass to die for. The crowd started to hoot and holler. Vanessa didn’t quite get it but could see people loved what she was doing so she kept doing it.

That is until the waist cincher disappeared. Her belly expanded and her curves flattened out a bit. Vanessa could feel it and look down and realized what was going on.

“Oh my god, no!” she squealed.

Next was the girdle. And let me tell you this was NOT EASY. It took 15 minutes for us to get it off her, but for the crowd it was instant. And just like that the real Vanessa was out there. Under her girdle she was wearing a sweaty pair of white granny panties. So the crowd next saw her like that. Her belly flopped out and over the waist band. Her thighs expanded. Her huge ass, which was wide yet flat, had grown four sizes. Vanessa screamed and placed her hand over her stomach to hide it, like she’d been hiding it for years now.

And finally came the bra. It popped right off and with it the two some silk pillows she’d been hiding in there since the seventh grade. Vanessa actual tits were A cups with pointy nipples that were now erect.

“You stuff your bra?” Kitty said thinking about all the taunts Vanessa made to her in school about Kitty’s B cups. Well now Kitty was for the first time unquestionably bigger than her rival. She instinctively stuck out her own chest in victory.

“I do not!” Vanessa yelled and then ran from the stage in shame. Still in her granny panties, stockings, and gloves she headed out one of the exits and to the holding room.

The last bid was by Danny and for $10,000. After Vanessa bolted he stood up and said “Can I withdraw my bid?”

Vanessa burst into the holding room and shut the door. She turned around and found Sophie there.

“You! You did this!”

“That’s right,” Sophie said.

“Well just so know you’ve accomplished nothing! I’ll tell everyone… that it was a planned skit with me and Kitty! Yes, and that I was wearing a fat suit. And no one will ever know. Kitty’s known me her whole life. She go along with it,” Vanessa said, trying to believe it herself.

Sophie just laughed. “You’re really pathetic, you know that?”

Vanessa’s face turned beet red with anger and she threw the hardest punch she could. Too bad it Sophie saw it coming a mile away and caught it with her hand. Vanessa couldn’t believe it. She looked at Sophie, eyes widened.

“Oh I’m so going to enjoy this,” Sophie said.

POW!

Sophie punched Vanessa knocking her onto the couch. Sophie rushed over for another blow when Vanessa’s gloved hands went up in defeat. She was crying.

“Please don’t hit me again!” she cried. That’s when Sophie spotted the bag in the corner.

“Is that your bag?”

“What? No.”

“The bag with monogrammed VE on it, isn’ t yours? Okay sure.” Sophie looked inside. “Oh my God, is this yours?”

“No!!”

“It is isn’t it? This is what you’re into!” Sophie said.

“No, it’s NOT!”

Suddenly Vanessa was standing with the sissy dress and panties on. The dress made for some slimmer so it didn’t fully cover her stomach and the blue frilly panties were tight on her ample bottom.

“Awww look at you,” Sophie smiled. “You know, I was going to kick your ass in here, but now I have a better idea.”

She grabbed Vanessa’s hand and took off one her leather gloves and put it on. “Nice.”

Then she grabbed Vanessa’s wrist and sat on the couch, dragging Vanessa over her lap.

“No! Don’t you dare spank me!” Vanessa said.

Sophie didn’t say a word at first. She just started spanking Vanessa’s filly covered bottom. Over and over. The leather glove leaving an imprint in Vanessa's soft cellulite covered ass.

WHACK!

“Owww!!”

Vanessa whined with each blow.

WHACK!!

“Owwwww!”

The leather glove stung more and more. Plus the added humiliation of the dress and panties. It was too much. Vanessa start bawling.

But Sophie didn’t care.

WHACK!

“Owwwwww!!”

Vanessa kicked her legs like a spoiled child.

WHACK!

“Owwwwwwww!”

And eventually Vanessa just became a mess.

WHACK!

“Owwwwwwww!!”

Sophie spanked her so hard and so long that eventually Vanessa was sucking her thumb. The rich sophisticate who looked down at everyone was now crying and sucking her thumb like a baby as she got the spanking she so badly needed.

But Sophie wasn’t done with her yet. Look at her panties Sophie grabbed a sharpie from the coffee table and made a correction. She turned the K to a T so now they read “Itty Bitty Titty”. She then tossed the sharpie began spanking her again.

WHACK!

“Ahhhh!!! Please stop!!!”

“You want me to stop?”

“Y-y-y-yesss.”

“Then I want you to confess what you’ve done. I want everything right now!” Sophie demanded.

“C-confess?”

“Yes! You stuff your bra, don’t you!”

WHACK!!

“Owwww yessss!!! Since the seventh grade!”

Sophie thought for a sec.

“And you hide all this disgusting fat, don’t you?”

WHACK!!!

“Y-y-yesss! I wear girdles every day!”

“And what else!”

WHACK!!

“And I’m frigid! I’ve never had an orgasm! I keep trying and it never happens! It’s not fair!!”

Okay Sophie wasn’t expecting that one.

WHACK!!!

“And what else!”

“And…and… and… I set up all these other girls to get humiliated! Tiffany Griffith, Tricia Sampson. All of them. I hate them and their perfect bodies!! It should be me that looks like that! It’s not fair!!”

Sophie was now satisfied. She gave Vanessa’s big fat ass one more spank and then pushed her off.

“Okay that’s it,” Sophie said. She stood up and walked to the door. Vanessa stood, still in the sissy dress and panties, and said, we’re done?”

“Yeah, we’re done.”

Vanessa sighed and began to rub her now bright red ass.

“Oh one more thing. Well two things really.”

“What?”

“This whole session we just had here? Was livestreamed out there,” Sophie said.

“What?!”

“And behind this door? Is the media.”

Sophie opened the door and a flood of paparazzi came in, taking pictures and showing microphones in Vanessa’s face. She stood there in her sissy dress and frilly panties and began to sob. Her entire confession had been livestreamed. She was ruined. As the camera and lights came closer she started to suck her thumb and her final shame: Vanessa wet herself on camera.

“I want my DADDY!!!” Vanessa whined.

Vanessa was done with Sophie but her problems were only just beginning. Her livestreamed spanking and her frilly panties led to “Miss Itty Bitty Titty” trending. Kitty recounted the “Princess Vanny” story when asked about this incident. The many resorts and exclusive places she went no longer wanted anything to do with her. And certain socialite women were next in line to get their **** on Vanessa. Worst of all was in the auction Vanessa DID get sold. A very rich older man named Herman bought Vanessa for $5 after all the other bids were rescinded. Several weeks later, a **** Vanessa went out on a date with him and was easily seduced. Herman was 5’10” and 300lbs, but loaded so Vanessa’ fractured ego fell to his charms. Herman was one of those rich guys no one paid any attention to so when Vanessa was back at his place it was easy for one member of the paparazzi to film it and leak it online. There was the newly crowned Miss Itty Bitty Titty in the exact situation she had planned for Kitty. Taking it up the ass from a sweaty fat slob while moaning and sucking her thumb, a new habit she had recently formed. The real highlight was the tantrum Vanessa threw when couldn't cum.

Sophie walked down the hall having utterly destroyed Vanessa and walked over to me, waiting at the end of the hall.

“Have fun?” I said.

“Yeah.”

She thought for a second.

“What’s next?” she said.