UMD Stories

Silly Lilly the Sillybitch: Can't Win for Losing Part Three
Story by vols4everus
Posted 7/8/22     653 views
Silly Lilly the Sillybitch: Can't Win for Losing Part Three


My so-called friends had one last trick up their sleeves. Richard wheeled out a pastry cart loaded with pies of all sorts, but mostly chocolate pudding ones. There were 26 pies on that cart. I know. I had a chance to count them. And I knew what was going to happen to them. I would be wearing them.

As I sat there on that seesaw wearing my now ruined favorite pair of panties on my head, completely covered with chocolate slime, I saw Marci count out ten of those delectable deserts and set them down beside me.

"There are ten pies here, Lilly," my former friend said, "Each one has a marble in it. Your challenge will be to retrieve the marbles. For each one that you successfully retrieve, you get a pie. For each time that you fail to retrieve the marble, you get hit in the face with the pie."

"You will have thirty seconds per pie. After that, failure will result in the pie being pushed into your face."

"And" she added, cutting me off before I could respond, "you'll have to use your mouth to do it."

Well, I guess you can imagine what happened. I managed to scoop up three of those overly large marbles with my mouth in the time allotted, but not the other seven. And of course, I had to bury my face in that chocolate filth each time. As I raised my head for the last time, chocolate pudding just ran down my chin and onto my bare boobs. I was so, so mad at Marci. But then she piled on to my dejected state of mind.

"Oh, I am so sorry, Lilly," my former best friend said with a snide look on her twisted face, "but you failed to accomplish the task in the allotted time. That means you get the mucky splat."

Seven times I got the mucky splat. When she picked up that eighth pie, though, I came unglued.

"What the fuck is that for. I GOT THREE OF THEM!"

"Oh, that's right. You did."

"Oh, what the hell," that witch said as she slammed that pie into my face, followed in short order with the other two.

"I was never really going to give any of them to you, dearie."

Now, I was really, really ticked off.

Oh, I'm gonna get you. You just wait. Someday, it WILL be my turn.

I can't even describe how I looked, how utterly trashed I was. But it wasn't over yet. It was going to get worse, a lot worse.

Marci, dear sweet psychotic Marci, my former best friend, brought out another ten pies. As she sat them down on a picnic table by that seesaw that I was chained to, I got my first good look at the filling. And my jaw dropped. If it hadn't been attached to my head, that jaw would have hit the ground.

"YOU HAVE GOT TO BE KIDDING ME," I shouted. "Those aren't even pies. THEY'RE MUD!"

"Well, yes . . ." Marci replied. "They're . . . mud pies." And the way she smiled, ever so sweetly might have fooled all of the onlookers, but not me.

"Honey," my newest arch enemy now said, "there is a marble in each pie. Your goal it so retrieve as many as you can using nothing but you r mouth. You have thirty seconds. Ready."

"You can just go straight to hell, bitch, if you think I'm going to stick my head in that shit."

"Oh . . . oh well," Marci said, "okay!"

And then she proceeded to hit me, in the face, with all ten of those "mud" pies.

Once again, mud was dripping from my head, down my face, onto my boobs, before falling to the ground.

Oh, you just wait, bitch. You just wait. One day, it will be MY turn.

Richard, that sorry ass Douch bag pushed that cart, with the remaining pies, directly in front of me. Each one was extra-large, and each one carried about three inches of pudding along with a nice slather of whipped cream. Though most of them were chocolate, in addition there were strawberry cream, banana cream, coconut cream, custard and even one really gooey caramel pie.

"Lilly, for your final forfeiture, we thought you would like to share the experience with some of your friends."

"NO!" I cried out with as much tone as my ruined vocal cords could carry,

Walking up behind Marci and Richard were four of my best friends. There was Mary and her husband, Ryan. Plus, Debbie and Cassandra, twin sisters I had known since first grade, were also there.

Why me, God? Why me?

And with that, those four got to hit me in the face with a pie. There were sixteen pies, so each of them got to slam four gooey pies into my face. When they were done, my face was completely obliterated.

Ryan actually had the decency to almost look embarrassed as he went first. That didn't stop him, however, from planting four of the messiest chocolate cream pies in my face. Each added an extra layer of muck and mire to my already trashed face. Mary gave me a pie sandwich using two of the biggest strawberry cream pies I've ever seen. This helped mitigate a large portion of the dark brown goo that her husband had inflicted upon my head. Now, instead of having a head full of brown gunk, I had a head that was full of brown gunk AND pink slime. Mary had been a long-time friend, but now that I thought about it, she had always been tight with Marci. To finish off her messing, Mary added a pair of chocolate pies in a front to back pie sandwich.

After Mary finished trashing my face, it was time for the twins to do their messy mayhem upon my dilapidated body.

Debbie went first, as she was always the more liberal of the two practical jokers. My boobs were all but hanging out of the ruined bathing suit, and Debbie took good advantage of that by planting a pair of custard pies onto them. And she took great delight in smearing that yellow muck into the cleavage and over my rock-hard nipples.

Great. Just one more round of humiliation! I can't win for losing

To round off her messy attack upon me, Debbie, a friend since first grade, slammed a banana cream pie into my face while plopping a chocolate monster down on top of my head. All that extra chocolate pudding and whipped cream splattered all down the front of my muck-covered face, almost, but not quite, covering up the damage done by her previous strike, the banana
cream one.

Last but not least, was Debbie's sister, Cassandra. And she finished the "dance of desolation" a term that Marci had coined a long time ago for total messy domination, with four different pies upon the four facets of my head. Cassandra started with a coconut cream pie to the right side of my face while pushing a strawberry cream one against my left side. She then added a custard pie to the back of my muck-smeared hair, before finishing her mucky attack with a full four inches of chocolate pie against what little was left of my face. Yep. It's true what they said. I was now under a total state of obliteration.

And then, last but not least, Marci walked up with a big mound of whipped cream covering but not totally obscuring a really gooey blob of almost liquidly caramel in a huge flan.

"Nooooooo!" I cried out as I saw that mass of ruination descend upon the top of my head.

I heard the loudest SPLAT I have ever heard as that mound of mess driven by a mass of hatred, slammed into my hair. To finish the job, Marci ground all of that flan into my scalp, destroying the pastry in the process, before slathering the remains down the front of my face and then onto the front of my boobs. And all the time, that lousy bitch was laughing her head off.

Ahhhh shit! How am I going to get all that caramel out of my hair.

But that wasn't all. Douchbag Dick walked up with a large bucket.

"What would chocolate covered caramels be, without the chocolate," he said with the most insidious sneer on his face.

And silly ole me looked up just in time, to catch all that splashing chocolate right in my face.

NOW, it was over! Now my humiliation was truly over. But not completely. No! My friends couldn't leave it there. They left me tied up and trussed like a hog, half naked, on top of that seesaw for the whole world to see as they walked away.
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