UMD Stories

Silly Lilly the Sillybitch: Can't Win for Losing
Story by vols4everus
Posted 7/8/22     907 views
Silly Lilly the Sillybitch: Can't Win for Losing

"Well, that's just great," I said after taking my first pie of the day. And naturally, that A-hole just had to pick chocolate. "What a dip wad," I sighed as I looked at my reflection in that puddle of water by the concession stand. My name is Lilly and I thought how silly I looked with dark chocolate dripping down from my pie-smeared face. I could feel everyone laughing at me, as they walked by, even if they were trying to ignore this silly girl in her ridiculous outfit. I mean, come on, who really wears a tutu anymore. Only little girls in fifth grade plays wear tutus. I'm a grown woman, in my twenties, with the whole wide world ahead of me.

Me and my big mouth! I had to do it. I just had to do it, AGAIN!

I thought back to my rash bet that put me in this silly little position.

"Okay, Lilly, here's the question. Who is the Sheriff of Nottingham?" Marci, my supposed best friend asked. But I know it was Richard who put her up to it. That little dip wad. All I can say is he'd better watch his back from now on.

Oh, I just knew the answer, so I had to go and double the bet. How dumb of me. But then, who would have thought that . . . ooooohhh . . . shit!

Who ever heard of Professor Harminder Singh Dua anyway? I mean everybody knows Alan Rickman played the Sheriff of Nottingham. EVERYBODY! How was I to know there is a real sheriff, right now, and his name is Harminder Singh Dua . . . it's just not fair.

And now, because of that birdbrain question, and my dumb answer I have to wear this, ridiculous outfit. Staring at that pool of water, I saw a five-and-a-half-foot tall woman with long brown hair dressed in a bright pink one-piece bathing suit with pink leggings and a tutu. On top of that, I had to wear a pink wig. But that's not all. Because of my big mouth, I had to do certain dares, each of which carried its own unique forfeiture if I got it wrong. And they were all designed for me to "get them wrong."

It all started with a trip to the park. Marci and Richard, of course, were with me every step of the way, to keep me from getting off track. It seemed like every 15 minutes there would be a new dare. And naturally I always got it wrong. My first punishment was the rather large chocolate cream pie in my face.

Oh dear . . . what's next!

"Next question, Lilly," this time it was dip-wad Richard who asked it. And with a really sadistic grin, Richard held up a triple-layer chocolate gateau cake. "Truth or Dare!" He said with a snide comment.

Oh shit. I'm so screwed!

"Did the New York Jets of the American Football League win their Super Bowl 6?"

"Shit, how the hell am I supposed to know that?" I just about screamed at that smug little bastard.

"Truth or Dare, Lilly," that grinning jackass said, while looking down at that really messy-looking cake.

Now the way Truth or Dare goes is two-fold. If you don't know the answer, you take the Dare, which in this case was going to be that cake in the face. But if you think you know the answer you say, Truth and then give the answer. The problem is if you get it wrong, then you get a double whammy, both the Dare, i.e., the cake in the face, but also an additional penalty which I wouldn't know until that bastard, Richard unleashed it on me.

Hmm . . . I know the Jets won one of those stupid games. I remember something about a guarantee. But which one. Hmm . . .

"True," I said, with anything but complete confidence in my answer. And I knew by the triumphant expression on Richard's face that I had got it wrong.

"False. It was Super Bowl 3 in 1969, when the Jets defeated the Baltimore Colts by a score of 16-7."

And then that smug little bastard set that cake down on the picnic table in front of me, while about a dozen pedestrians walked by, looking at my pie-covered face.

Then every one of them looked down at that cake and started grinning.

Imagine, the nerve of them.

"You know what to do, Lilly!"

Oh, I so wanted to wipe that smug expression off his face. I wanted to rip out his tongue and shove it down his throat. I wanted to . . .

"Lilly?"

"YEAH, I KNOW!"

Shit!

Then I took a deep breath, closed my eyes, and dunked my head into that really, really, messy chocolate cake. Not only did the cake have about an inch of buttercream frosting on it, but being a gateau rather than a traditional cake, there was also a ton of chocolate goo in between layers. As I drove my face and head down, deeper into that messy mound of mayhem, I felt the grime slop up around my head and shoulders, covering my face, then my hair, and all but exploding out and around the back of my head. When I looked up, I knew by the expressions on everyone's face that I was a complete wreck.

"And now for the second part of your punishment, Lilly . . ."

Oh no! I knew what the dipshit was going to do when he pulled out that two-liter carton of chocolate custard and started staring at my boobs.

"Come here, Lilly," Richard said in his sternest voice.

I complied with his order.

As I stood in front of Richard, that smug bastard, reached out, pulled open the top of my bathing suit with one hand, and started pouring that chocolate mess down the inside of that perverted pink outfit. Oh, and did I mention just how cold custard could be when poured over your private parts.

It was so horrible when that chocolate mess hit my boobs, but it became increasingly worse as it trickled down and into my inner workings if you know what I mean. Oh, I can't even begin to describe the agony. And that bastard just kept grinning like a jackass as he poured every last friggin' drop of that custard down my bathing suit.

I was freezing my ass off when the next of his sick dares came up and bit me in the ass. The forfeiture for that loss was having to hop around on a space hopper (you know, those big rubber balls that you barely hang on to with a really small ring on top). And while hopping around I had to drop 23 pink-tinted shaving foam-filled balloons across the playground. And I couldn't break any of the balloons. If I did, I had to scoop up that shaving foam and smear it across my chest. Eight times, I had to do that shit.

"Lilly, how many seconds are there in a Leap Year?"

"How the fuck am I supposed to know that?"

"Lilly," Richard said, "you have sixty seconds to come up with an answer."

Desperately, I tried to get a pencil and a piece of, . . . anything . . . to figure it out. But one minute just wasn't enough time.

"Fuck! I don't know."

"The answer, Lilly, is 31,622,400."

So, it was twenty-three balloons filled with pink shaving cream and that stupid space hopper.

But then came the really sick shit that bastard came up with. To top it all, I had to walk into a McDonald's restaurant and buy, with my own money, five fucking ice cream cones. Then I had to go into their restroom and using all the ice cream and one of those cones, form a messy horn which I stuck to my forehead while loudly proclaiming that I was now a unicorn. With melting vanilla ice cream running down my chocolate-covered face, I had to walk past all their employees and customers, and it was the noon rush, so the place was packed, loudly announcing that I was a unicorn as I walked back to the playground.

Then my challenge was to push those remaining fifteen shaving cream-filled balloons into a basket over by the seesaw. Do you know how difficult it is to push a balloon filled with pink-tinted shaving foam around a playground. Now imagine doing it while on your knees and your hands behind your back. To further the difficulty, I had to push those balloons with my "unicorn" horn.

Needless to say, I only got four of those stupid balloons into that basket. The other eleven burst when I put a little too much pressure on them with my horn. And of course, all that pink shaving cream wound up on my face.

By the time I had finished this silly task, my face, in addition to all that chocolate goo, now carried a hefty amount of pink foam. Needless to say, I was not very happy with my friends at this time. But it would get worse.

Next, I had to balance a rather large balloon, again filled with pink shaving cream, between my thighs while I walked across the parking lot at McDonald's. or rather, waddled across the pavement. And at the same time, I had to balance a two-foot pole, over my head, with my mouth. Oh, and at the end of the pole . . . a chocolate pudding pie with extra whipped cream on top.

Well, you know what happened. I got a little too much pressure on that fucking balloon, which caused it to burst, showering my crotch and inner legs with even more shaving cream And this, of course, distracted me so that I lost the balancing act with that pole, and you know what that meant. I got another face full of chocolate and whipped cream when that pie fell on me.

My next challenge was to dance like a stupid chicken for five minutes, while holding a dozen eggs. Every time I did not dance properly, I had to smash one of those eggs on my forehead. And it seemed that I did something wrong about every thirty seconds, so it was splat. Needless to say, none of those eggs survived a meeting with my face. Now I was really getting pissed. The more slime I felt rolling down my face, the madder I got.

Oh, and did I mention that there were about fifty people watching and laughing their fool heads off.

And then there were the two dozen, other balloons that were filled with pink-tinted shaving foam. Do you know what I had to do with them? I had to put them in my bathing suit. Do you know how hard that is? I mean maybe if I was flatter than a pancake, but hey, I have boobs. Good boobs. Good-sized boobs. But I had to do it. That was one of the stupid forfeitures, that I had to pay.

And then do you know what those two did. What my friend, my supposed best friend, Marci, and that shithead Richard did? Each of them took great delight in using a pin to pop each of those 24 balloons. Pop, pop pop. And each time they would say, "pop goes the weasel." You know that stupid song. If you think it was bad enough getting all that shaving foam on my outside. Think again, about how it was inside my bathing suit, on my boobs, over my . . . well you know what. Plus, I now had twenty-four little holes in my bathing suit.

The next time I screwed up, and on this day, it happened quite often, I got a very large bowl of custard over the top of my head. It must have been at least four liters, and that just added one more, new, layer of mess to my sorry state of muckiness. And all because I didn't know the answer to dipshit dick's stupid question.

"Lilly, what World War I battle did Winston Churchill lose?"

"What? Are you out of your fucking mind? Churchill didn't lose. He won the damn war, you idiot!"

"You weren't paying attention, Lilly. That was World War II that he won. The question was . . . what battle did he lose during the first World War?

Oh Fuck! How the hell am I going to know that. Shit. Now I wish I had paid more attention in history class.

"Lilly, it was the Gallipolli campaign where the British suffered over 187,000 casualties. Churchill was the First Lord of the Admiralty at the time and was soundly criticized.

And since I couldn't answer that question, I got the custard over my head.

But now, the punishments seemed to come in droves as my friends, or should I say, former friends kept piling on the messes.

There was the double whammy just because I didn't know all the words to Scotland the Brave. It started with having to sit on a cake. And it wasn't any old cake, it was another of those monstrous chocolate gateau cakes like the one that I had planted my face in earlier.

And that little dip wad wouldn't let me sit down easily. Noooooo, he had to make sure I was going to get my butt messy. He all but shoved me down into that mess.

Brown muck squirted everywhere, some even ran up my front and struck the bottom of my chin. But when I stood up and bent over to get a look at the damage done to my derriere, that sadistic bastard slapped a big custard pie onto my rear, and wouldn't you know some of that splatter hit me in my already unrecognizable face.

Then that low-life, scum-soaking, pond-scum had me low-crawl through a mudhole out behind McDonald's. Me . . . crawling in the fucking mud like I was some grunt in the army. And he must have been preparing it for days. That pit was at least five meters long by two meters wide. And the mud was probably half a meter deep. Oh, and you know what else that piece of shit had me do? I had to use my nose to push another large balloon filled with shaving cream. And you guessed it. I wasn't halfway through that mud before the damn balloon burst, covering my muddy face with more pink shaving cream. I couldn't win for losing.

Oh, and he just kept laughing his ass off, while saying I STILL had to continue crawling through the mud. When dipshit dick finally let me get up, I was a wreck. I was completely saturated with that filth. Mud didn't drip off me, it rolled off me. And everyone from McDonald's were laughing there asses off.

Those fucking jackasses must have been in on this. Ooohh!

Then that redneck hick brought out the pies. Or rather Marci, my one-time best friend did. After duck walking me to the first picnic table, I had to sit on top of the table, with my arms behind my back. And I couldn't move, while that little witch smashed pie after pie onto my mucky body.

And this was all because I didn't have the right answer for who was the commanding general at the first Battle of El Alamein.

"Lilly," that smug bastard said, "who was the commanding general at the first Battle of El Alamein?"

"Monty," I blurted out. "It was Field Marshall Montgomery." But I knew by the jubilant look on his face, that Dipwadicus Dick was going to tell me I was wrong . . . AGAIN.

"I'm so sorry, Lilly . . ."

Yeah, in a pig's ass. You're not sorry about anything Douch bag.

"but the answer is General Claude Auchlinleck."

"What? Who the fuck is . . ."

"Lilly, you're confusing facts. Lieutenant-General, not Field Marshall Montgomery was the commander of British forces during the Second Battle of El Alamein, not the first one.

"And now, our good friend Marci, has some punishments for you. Hehe.

And she took great delight in delivering this new round of punishments.

Marci started the "treatment" as she called it, by slapping a chocolate cream pie into my face, just like Douchbag Dick did with the first pie of the day. And she knows how much I hate chocolate. Then she plopped a banana cream pie on top of my head, before finishing off my head with a pie sandwich made up of two chocolate custard pies. You can pretty much guess what my face and head looked like at this point.

But she still had two pies. One was a coconut cream pie, and the other was a strawberry cream one. And I knew where they were going when she started looking at my boobs and sneering like a hyena.

By this point, a rather large crowd of onlookers were ogling me and snickering behind clinched hands. Marci giggled like an old maid and said, "should I?"

Then she planted them, both pies, right on top of my boobs.

Thanks, that's just what I needed.

Marci and the dickless wonder brought out another dozen pies. And they started giving them out to the onlookers. Now I was getting hit with pies from four or five different directions at the same time. The last was from this older guy wearing a t-shirt that said Montana State University, Billing, Montana.

"Well, hell . . . pile it on," I said as the last of those pies hit my face. At least that Montana guy looked a little bit ashamed.

But they weren't done with the pies. No, not by a long shot. I'll tell you about that later.

Now the goo and glop started coming with regularity, and it was so messy, and so humiliating. I'll tell you, if I had a gun then, I would be facing the gallows now.

Those two airheads upped the ante with Richard's next question.

"Lilly, what famous World War II battle did Field Marshall Montgomery design with the plan to 'end the war by Christmas?'"

"Duh, do I look like a fucking historian? Why do you keep asking all these history questions?"

"Lilly, your answer, please."

"I DON'T FUCKING KNOW . . . OKAY!"

"That would be an incorrect answer, Lilly. Monty's Operation Market Garden, which was a disaster for the British 1st Airborne Division was his plan to end the war by Christmas. Since you failed to give the correct answer, you know what that means?"

"You want me to do WHAT?" I cried out in anguish. After Marci's pie assault, I thought I might catch a break for at least a few minutes.

Uh uh. Those two twits were just bound and determined to heap on the misery.

Just after Marci finished pelting me with those pies, and Richard asked me that bullshit Market Garden question, he came strutting up with a big bucket, one of those five-gallon ones. He plopped it down right in front of me. I was trying to clear my face of as much of that pie slop as I could, especially from my eyes so I didn't notice what was in it at first.

After grinding my knuckles into my eyes, though, I was finally able to see. And when I saw all that oatmeal, I just about fainted.

"Lilly, for being such a mess, you are sentenced to one head dunking in this bucket of oatmeal."

"You want me to do what? What was that? You have got to be kidding if you think I . . ."

"You heard me," that slimy ignoramus said in a sanctimonious manner, "get down on your knees and dunk your head into that bucket. And . . . I want to see your entire head all the way in the bucket."

"You go fu . . .," I stopped just short of losing it completely. That's what the bastard wanted.

"I . . . uh . . . oh shit," this last I said in a bare whisper, turning to Marci hoping for some show of pity. But there was no sign of any in her mocking gaze. A taunting look told me there would be no sympathy from her.

"Fuck." I wasn't getting out of this so there was no reason to prolong the agony. I dropped to my knees, took a deep breath, closed my eyes, and plunged my head down into that shit.

I can't describe the feeling of that glop, but it wasn't pleasant. At least it was still warm, so that wasn't so bad, but sticking my head in a bucket of oatmeal was not something I ever thought I would have to do. I do know this, though. As long as I live, I will never eat oatmeal again. As my head went deeper into that bucket, I could feel that slimy cereal flood up and over the sides of the bucket. I actually felt some of the flooding muck flow down the open neckline of my bathing suit.

I don't even want to think about what I looked like when I pulled my head out of that gunge. But I couldn't see, I couldn't hear, I couldn't even breathe as my nose was completely full of slimy muck.

Shit, I didn't think about that. Should have plugged up my nostrils with something.

With both hands I started pawing away as much of that goo as I could from my face. Then I started trying to blow my nose to eject the gunk that filled my nostrils. With my index fingers I tried clearing my ears so that I would be able to hear. Never have I felt so miserable in my entire life. I could barely see, could hardly hear, and still had to breathe through my mouth. I was a complete mess. And then, it got worse.

In no condition to fight back or even resist, I was kneeling on the ground among all that mess, when my two companions dumped the rest of that bucket over the top of my head.

For a full ten seconds I knelt there in total shock. How could they. How could SHE?

My entire body was now soaked in oatmeal. You could no longer see where they had pelted me with so many pies and cakes. That was covered with oatmeal.

At least they did give me some time to recompose myself. I had about five minutes, probably because they were laughing so hard that they couldn't unleash anything else at the time.

Fuck. This is the worst day of my life.

Little did I know how much worse it was going to get.
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