UMD Stories

The Lottery WInner (Pt 3)
Story by LongTimeLurker
Posted 10/21/21     1299 views
"Dressed up? Are we going someplace fancy?" Jenny asked.
"There are no restaurants out here. I can't even order pizza to be delivered. I hired a chef to come out a make a special meal just for the two of us tonight. The chef will be around 6:30 and the first course should be served at 7. I thought we might have a good reason to celebrate." Anna replied, shaking her head at Jenny.
"Wait, what am I going to wear? I didn't bring anything!"
"You are so forgetful sometimes! Don't you remember where you got that outfit you just got slimed in from? Everything in that closet is yours. Everything in that dresser is yours. Everything in that room is yours."
"Oh yeah...I totally forgot. You're kind of distracting standing there in the nude."
"Let's go hang out by the pool for a bit before we have to get ready. You also have a variety of bathing suits to pick from."
A few minutes later the two ladies were laying out on the deck by the pool, both wearing bikinis that barely covered anything on their bodies. All of that day's activity had really worn-down Jenny, combined with getting up so early and it didn't take too long before she fell asleep.
Anna woke Jenny up by throwing a bucket of water onto her as she was sleeping in the lounge chair.
"What the hell!" Jenny shouted.
"Hey, it's 5:00. We've got an hour and a half before the chef gets here so I thought you might want to get yourself ready?"
"Sorry, thanks, I guess," Jenny replied, a little groggy, as she rubbed her eyes, trying to wake up.
They each went up to their rooms and started getting ready. Jenny spent a lot of time in her shower, still finding chunks of slime in her hair. Then she spent a significant amount of time trying to pick out what to wear. She finally decided upon the blue formal dress that had caught her eye earlier that day. She found a matching blue strapless bra and blue thong panties that she thought would be perfect for the evening. She thought about looking for some stockings to wear but decided against it since the dress was going to reveal so much of her leg. She slipped on the shiny blue high heels, looked in the mirror one last time to make sure her makeup and hair were perfect, before heading downstairs.
The chef and his assistant was apparently already there as Jenny heard Anna talking to them in the kitchen. Anna came around the corner and almost bumped into Jenny as she did. Anna looked amazing as she was wearing a tight red, strapless dress, that hardly even attempted to cover her generously sized breasts. And, of course, she had on matching red stiletto heels. Her blonde hair was curled meticulously and flowed down over her shoulders.
"The chef has set up a candlelight setting on the table just outside the backdoor on the patio. Would you care to join me there?" Anna asked.
"I'd go anywhere you tell me to. You look so good."
"You don't look so bad yourself."
The two, well-dressed ladies walked out onto the deck and sat down at the table which was now appointed with a tablecloth, a fancy setting for two, and a couple of candles. As they took a seat, a young woman in a chef's outfit came out from the kitchen.
"Would you like some champagne?"
Jenny looked back at Anna and laughed as she said, "Why, of course, I would."
The young woman popped open the bottle of champagne she was carrying and poured it into the two glasses on the table.
"Here's to your newfound wealth! Cheers!" Jenny said as she reached across the table to tap Anna's glass.
They sat and drank and eventually, the chef's assistant brought out an appetizer for them to share. Jenny was mesmerized by the young woman's hair which she could just barely see under her chef's hat. It looked like it was bright pink.
"Did you see that girl's hair?" Jenny asked Anna.
"I didn't notice it. I'll look next time she comes out."
Soon after a small salad was brought out for each of them. But this time it looked like the young woman's hair was bright purple. Jenny looked over at Anna and shrugged her shoulders.
After the salad came the main course, a delicious chicken breast in a light cream sauce with some asparagus before the young woman with the purple/pink? hair came out with a small creme brulee as the dessert. Jenny was a little surprised by the dessert as she had expected something much larger that they would get messy with but had to admit that it was delicious. Once they finished it off, they started on the second bottle of champagne when the chef walked out.
"Did everything meet your expectations?" the chef asked Anna.
"It was delicious. Thank you so much for doing this."
"It was my pleasure, have a wonderful evening." And with that, the chef went back into the kitchen and soon left the house.
Jenny had assumed that his assistant had left as well, which was disappointing as she had really wanted to ask about the hair. And she was pleasantly surprised when the young woman (with pink hair) came back out to ask if they were ready for the next course. Jenny wasn't sure what that meant, but Anna quickly replied that they were ready. The young woman walked back into the kitchen and left Anna alone with Jenny again.
"What does she mean by the next course?" Jenny asked. "I thought we were done, the chef left?"
"I have no idea, but let's just sit back and see what happens," Anna said with a little grin.
Jenny knew something was up, but she was pretty buzzed from the champagne at that point, so she just went along and took another drink.
The young woman came back out, carrying something, but she stood directly behind Anna so she couldn't see what she was holding as Jenny was sitting directly across from Anna at the table. There was silence for a moment, which ended when the young woman lifted a large bowl and dumped its contents out over Anna's head. It looked to Jenny like it was chocolate cake batter. As this was happening, Jenny felt something being dumped over her head, which was very confusing. As it streamed through her hair and down her face, she tasted it and discovered she was on the receiving end of some vanilla cake batter. The batter flowed down onto her dress, with a significant amount ending up going down between her breasts and under her dress.
When the flow finally stopped, Jenny reached to wipe her eyes clear, but that attempt was interrupted when Jenny was on the receiving end of a large pie sandwich. The cream pushed into her ears and then was smeared to engulf her entire head. She could feel chunks of pie crust and cream dropping down the open back of her dress as well as down the front onto her breasts.
Someone grabbed her arms and pulled her to her feet. Then that same someone quickly tied her hands behind her back, removing her ability to clear her eyes to see who was doing this to her. It was a little scary but also very exciting and arousing at the same time. So many unknown things going on at the same time.
Jenny felt what she thought was a woman's hand on her shoulder which was then followed by feeling the fingers reach underneath the straps that held the dress up. She heard a snip, then another snip, and one final long cut, which resulted in her dress not only being ruined but also falling to the ground on the patio. Next, she felt the hands grab the back of her blue, lacy bra which was followed by another snap. And finally, the hands worked their way down to her skimpy little blue thong panties, which, with a little work, were also cut and removed. Now she was completely naked except for her blue heels, and of course, the pie and cake batter that coated her body.
Jenny heard Anna let out one of her squeals of excitement, so Jenny assumed she was getting the same treatment from the chef's assistant. Just as Jenny started to relax a little bit, she felt a pie being smashed onto her exposed ass, and then another was not only smashed but worked onto and into her exposed pussy. Jenny let out her own squeal of excitement at that maneuver.
The hands touched Jenny's shoulders again, but this time they were pushing her backward until her legs hit the wooden table that they had been eating at. The hands pushed a little harder and Jenny ended up setting her pied ass onto the wooden surface of the table. She felt another pair of hands grab her hips from behind and pull her to what she assumed was the center of the table.
There were some more sounds and movements until Jenny felt another pair of tied-up hands against hers on the table. "Is that you Anna?"
"It's me," Anna replied. "You ok?"
"It's dangerous, and it's scary, and I'm so turned on right now..."
Before Anna could answer, there was another dump of cake batter over both of them, vanilla again.
Then Jenny felt hands grab her ankles and pull her legs apart, leaving her pied pussy completely exposed. She wasn't sure what was going to happen next, but it didn't take long before it did...Another pie was slowly pushed onto her exposed pussy, and she felt fingers working the edges of her most private of areas. Jenny really wanted them to go all the way, but they pulled away just as she was getting ready to go.
Jenny's breasts were then on the receiving end of a pie each before another pie was smashed into her face, just for good measure. And then it got interesting...Jenny felt what must be a very large dildo entering her pussy and it was making things happen down there.
It didn't take long before Jenny reached her climax and let out a few good moans. The dildo was removed and just as she started to let her guard down, another pie was pushed into her face. She heard Anna make some similar noises and a few moments later, she heard a snip, and her hands were free. Jenny wiped her eyes clear, which took a couple of tries due to the many layers of mess that had been placed on her.
Once she could open her eyes, she saw two "chef's assistants" standing in front of her, their white pants and jacket splattered with pie and cake batter.
Anna grabbed Jenny's hand as she swung around on the table next to her. "Jenny, I'd like to introduce you to Kaley and Haley, yes they are twins."
The twins took off their chef's hats to reveal that one of them, Haley, did, in fact, have pink hair. Kaley's hat removal revealed that she had purple hair. It all finally made sense to Jenny.
"I met them a year or so ago and we ended up doing a messy video together. I flew them out here to do this and they were kind enough to take part."
"This was so much fun. You two are the best! I don't know if Kaley will agree, but I would do this anytime you ask!" Haley responded.
"Did you enjoy this, Jenny?" Anna asked.
"100%. That was one of the most exhilarating experiences of my life. I just need to know which one of you was the one pleasuring me?" Jenny asked, still wiping stuff off of her head.
"That would be me," Kaley answered. "Sorry if I got a little carried away. Just got caught up in the moment."
"You can get caught up with me anytime."
Anna and Jenny got off the table and Haley took a few pictures of everyone together. "Jenny, let's get rinsed off, so I can walk without feeling like things are still going up inside me."
"Good idea," Jenny responded.
Haley looked over at Kaley, who shook her head in approval, "Is that all you need from us tonight? We can get out of your hair if you want us to?"
Anna, turned as she walked towards the outdoor shower, "Not so fast you two. I have more surprises left and this time you're not getting out so clean. Why don't you guys take a rest in the hot tub while we get cleaned up?"
They nodded their heads in agreement and proceeded to get out of the outfits they were wearing, revealing some very sexy, toned bodies. Jenny couldn't help but stare as they walked over and sat down in the hot tub, completely naked.
Jenny's trance was broken when Anna smeared some pie from her head onto Jenny's face. "Hey now! You're supposed to be with me. Although I can't take my eyes off them either."
After they got cleaned up, well, mostly cleaned up, Anna and Jenny joined Kaley and Haley in the hot tub. The four of them shared stories of getting messy and other activities as Anna opened another bottle of champagne for them all to share. Jenny laid back and realized that she could actually see stars in the night sky. She couldn't see them in the city. It was a perfect evening.
As the last drop was poured out of the bottle, Haley asked, "What's this last surprise you talked about earlier?"
"Are you all ready for it?"
Everyone nodded their heads as they took another drink from their glasses.
"Do you want to get messy in the nude or do you prefer we get dressed?" Anna asked.
"I mean, we've been naked all night, why change that now?" Jenny said laughing.
Haley and Kaley agreed.
"Ok, let's finish off your drinks, or don't, and let's go."
The four ladies chugged what was left of the champagne in their glasses and climbed out of the hot tub. Anna led the way around the side of the large house to a staircase.
"Glad I'm not still wearing heels, given all that I've been drinking tonight," Jenny said. "I doubt I could it make it up these stairs."
"I'll have to keep that in mind," Anna said as she walked up the stairs.
Jenny followed Anna up the stairs and, in that moment, took a second to realize that she was following the woman she loved, naked, up a set of stairs that was outdoors. It was a great view of her ass, and to top it off, there were two naked women behind her, looking at her ass. And, maybe the champagne helped, but it didn't feel strange at all. It felt...right.
Anna reached the door at the top of the stairs, which, had anyone not been pretty well buzzed at that point, would have realized that it was above the garages at the north end of the house, and it was also the tallest portion of the house, meaning that they had made their way up to the third story of the house. "Dammit!" Anna yelled.
"What is it?" Jenny said, concerned for Anna.
"I forgot my keys since I'm naked."
"Guess we're going back down," Haley said turning around.
"Just kidding, come on in!" Anna laughed as she opened the door.
The four ladies walked into the house and entered a large loft area with a balcony railing on the side of the room looking down into the "garage" where the former owner had parked all of his fancy cars. The loft had a small kitchenette setup, almost as if it was like a mother-in-law suite. There was a bathroom with a small shower in the corner, against the wall away from the railing. There was a couch, a desk setup, and a very noticeable spot on the floor that was marked with a big, red "X."
"Who's going to be first?" Anna asked, with a big grin on her face.
Haley didn't waste any time and jumped over to the mark on the floor. Anna walked over to the desk and, sure enough, there was a big red button waiting for her there. She looked back at Haley, thought about saying something, and then pressed the button.
Nothing happened at first. Haley had tensed herself up in anticipation, but when nothing happened, she relaxed. "So... what is the sur-"
At that moment, the trap door she was standing on dropped from underneath her feet, and down she went. Before anyone else could get over to see what happened, the floor closed again. They did hear her screaming for a few seconds before hearing the sound of a muffled splash.
A few moments later, "OH MY GOD!!!"
"Don't say anything down there!" Anna yelled out. "Your turn Kaley."
Kaley hesitated but slowly made her way onto the red "X." "I guess, I'm ready?"
Anna pushed the button, and like last time, there was a delay, but Kaley was not going to be surprised by the delay, until she was, when the floor dropped out from under her. She screamed like Haley until the muffled splash. "HOLY SHIT!!!"
"Keep it quiet!" Anna yelled again.
"Let me guess," Jenny walked to the mark on the floor, "the delay is so you can do this to yourself?"
"You know me so well. Have a nice drop." And with that, Anna pushed the button.
Jenny took a deep breath and waited for it to happen. Just when it seemed like it wasn't going to happen, it did. The floorboard dropped and Jenny fell onto a slick slide. She quickly thought to herself that the previous owner must have had a thing for slides. Much like the one in the bedroom, the slide curved around, but this one was faster because there was some clear slick substance on it. The slide entered a tunnel, and everything went black for a moment before Jenny reached the end of the slide, where she was shot out into a giant tank of thick treacle.
It swallowed her up and as she stood back up the thick, sticky treacle slowly dripped off of her head. The tank was deeper than one tank Jenny had been in before. Standing in the tank, the treacle came up to about even with her breasts. Haley and Kaley were shorter than Jenny, so the treacle basically was up to their necks. As Jenny wiped her eyes clear, Anna came sliding down and shot out into the tank, sending the sticky mess towards Haley and Kaley.
Anna popped out of the mess, "What do you think?"
"It's deep.: Haley said as she flicked some of the treacle at Anna.
"Yeah, I may have added a bit too much."
"I am really curious about the previous owner of this house," Jenny said. "He must have had a slide fetish."
"Are you complaining?" Anna asked as she flicked the treacle back at Haley.
"No, it's just weird. But I guess you're a weird rich person now too..."
As Jenny finished speaking her legs were pulled out from under her, as Kaley had dived under the surface of the treacle and grabbed Jenny's ankles. They wrestled around before finally coming back up for air, with Kaley being very handsy with Jenny. Jenny didn't mind as it wasn't nearly what Kaley had been doing to her earlier, but Anna noticed. She quickly made her way over to Jenny and jumped up, wrapping her legs around Jenny's midsection, and began kissing her on the lips.
Kaley backed off and Jenny was a little disappointed but still enjoyed the attention from Anna. She wasn't used to having this much attention placed on her.
"Is there a shower for us to use down here?" Kaley asked.
Anna climbed off of Jenny and replied, "I've got something better. It's my final surprise of the evening... Are you ready for it?"
Haley and Kaley both nodded their heads in approval.
"Ok, everybody out of the tank!"


(To be continued...)
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Comments:
Chuck M:
10/26/21
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these stories keep getting better and better...can't wait for the next one!
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