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Never Cheat at Truth or Dare

A sleepover and a little pushing bring Penny's dark desires into the open
The whole thing was stupid, and I really wanted to be somewhere, anywhere else. But I had agreed to the sleepover at Mandy’s, and she hadn’t allowed me to go back on my word. Thus I was stuck with spending the evening with her, that stuck-up bitch Jen, a strange goth called Liz whom I didn’t know at all and had only gotten some glimpses of at school, and to round up things in the worst possible way, Naomi. Not that Naomi had an unpleasant personality, she was quite outgoing, bright and funny. Her big fault was that she tended to be all touchy-feely, and especially around me.

“Mandy,” I complained from my place at the top of the bed, my arms wrapped around my knees and feeling a bit silly in my pink nightie, “we’re all twenty, not fourteen. We don’t need to play silly truth-or-dare games anymore.” She really should have told me that it wasn’t going to be just the two of us, then I would at least have chosen something different to wear.

The bed dipped next to me, and before I could react, Naomi had settled down to my left and put her hand on my arm. I tried not to flinch. I knew I was a bit neurotic about being touched by others, but I felt she should be able to respect that. She didn’t, though.

“Oh come on,” she purred in a voice a little to deep for her fragile body, “everyone’s in but you. Don’t be a spoilsport. And you haven’t even heard the rules yet.”

Her ebony fingers ran up and down my arm, and everyone was staring expectantly at me. With a sigh I gave in, hoping that Naomi would cede her unwelcome means of persuasion. “Okay, okay, I’ll play.”

Mandy squealed and jumped onto the bed, occupying the free spot at the left side, with a stack of cards in each of her hands. Jen was lounging on her stomach at the foot of the bed, looking bored and wiggling her feet, showing off her bright red toenails. Liz was wrapped in a white and black kimono and sitting at the edge to my right, pale, her nails and lips painted black, reminding me of a cheap vampire movie.

“Okay girls,” Mandy commanded with a flourish, “pay attention. I’ve got two stacks of cards here, the blue ones are questions, the red ones are dares. We’re going in a circle, clockwise. If it’s your turn, you pick a card and read the question aloud to the girl to your right. She can either answer the question, or decline, then you get to pick a dare card and read that one for everyone to hear, and she has to fulfill it. Any questions?”

I was truly getting uncomfortable, but I had agreed to play. I could just hope that things would stay harmless, but somehow, knowing Mandy’s proclivity for the outrageous, I was fearing the worst.

“Why don’t you start, Penny, since you were so reluctant to play?”

I hesitantly picked a card from the blue stack and turned it over.

I looked at Naomi, whose shin was bumping against mine, but I was left with no room to pull away. So I cleared my throat and read the question. “With whom did you have your first real kiss, tongue and all?”

Naomi took a bit of time, and after a half minute of silence, I was almost sure she’d opt for a dare. But then she opened her lips and spoke in little more than a whisper. “It was with Brenda Wilson, at my eighteenth birthday party.”

So the rumors were true, Naomi was gay. Which made her touches feel even more intrusive in hindsight. Strangely, the others didn’t seem surprised. Maybe I was a bit naive.

But it was her turn now, and she picked the top card to ask Mandy.

“How often do you masturbate?”

Now everyone was staring at Mandy, and her cheeks started to glow. But she, like Naomi, opted for truth. “Once a day,” she said meekly, her eyes closed, “sometimes twice.”

Jen and Naomi giggled, and Liz whispered something under her voice that sounded suspiciously like “horny slut”, but I couldn’t be sure. The only thing I could be sure of was that this version of truth or dare was going to turn out far more intimate than what I had expected. I didn’t like that.

“So, Jen,” Mandy had caught herself was back to her energetic self, “how many people have you had sex with?”

Now that would be interesting. There were all kinds of rumors going around the school, from her being frigid to having been with the whole basketball team. I wanted to think that both were quite off track, but the speed with which Jen asked for a dare made me reconsider.

Mandy turned over the top dare card and appeared delighted. “Take off all your clothes and get into a kneeling position. Stay in that position until the game ends or another dare tells you differently.”

I could see the hesitancy in Jen’s face, and I have to admit it pleased me to see her this uncomfortable. She seemed unwilling to follow the order, and I didn’t think she would really do it, but then Liz growled her name, and what I thought was a flicker of fear danced across Jen’s face. She jumped up like stung by a bee and almost ripped her pajama top and bottoms away from her body.

This was really strange, something was obviously going on between those two. Jen had knelt down by now, and her eyes were boring holes into the bedspread in front of her. Her left arm covered her breasts and her right hand shielded her pubes.

I couldn’t believe my eyes. Then Liz reminded her that it was Jen’s turn to pick a card, and she took it with trembling fingers. Now I could see that she did have pretty breasts, not big, but perfectly shaped and with dime-sized nipples in a rosy color. I couldn’t keep from staring at them, and my heart started to beat a mile a minute.

“What,” she asked with a meek voice, her face pointing toward Liz, “is your favorite erotic fantasy?”

Everyone was staring at Liz now, and it was obvious that she enjoyed being the center of attention. With a coy smile she licked her lips, then looked intently at Jen. “Let’s see…” Her voice was almost a purr. “I love the picture of having a beautiful, nude blonde girl across my lap and spanking her wiggling ass until it is a deep shade of red.”

Jen’s eyes went wide, Mandy gasped, and someone moaned. That someone having been me, a fact I realised when all eyes came to rest on me. I closed my eyes and wanted to vanish into the ground when everyone stopped talking.

A minute must have gone by, a minute filled with the rushing of blood in my ears and the crazy beating of my heart. Then Liz’ voice pierced the silence. “Tell me, Penny, who do you think of when you masturbate?”

My eyes must have grown wide as saucers. That was one question I really didn’t want to answer, especially not now and in present company. But I didn’t want to pick a dare either, I’d probably end up naked like Jen. Or worse. I felt the others’ eyes rest on me, and I started to tremble. I needed to think quick. A satisfying answer. “Mark Bowler,” I gasped hurriedly.

“Really?” Mandy lifted an eyebrow.

I quickly nodded. Mark was one of the sports cracks of the school, and his body was all muscles, in a lean, athletic sort of way.

“Are you really, really sure about your answer?” Mandy didn’t let go.

“Of course I’m sure. Why are you asking?”

She smiled sweetly at me, and then her hand dug under the blanket and pulled out a brown, rectangular item. I should have realised at this point that the evening had been a big setup for me, but in my fear and embarrassment, my thoughts were all over the place.

And then I recognized the brown item. “Mandy!” I cried in desperation and tried to jump up and grab my diary, but two pairs of hands latched onto my arms and held me down.

“Sit on her legs,” Liz ordered Jen, who immediately complied.

I squirmed and pulled, but I didn’t stand a chance against the three girls. Then Mandy started to read from my diary, and I gave up struggling. Instead, tears started to trickle down my cheeks.

“Dear Diary,” she read, “I don’t know what is wrong with me. Why I’m having this thoughts when I play with myself. Ever since the fight with Jen I can’t think of anything else but of her and Naomi, holding me, tying me up, pinching and slapping me. It’s gotten so bad that I don’t dare to give myself the big O. What’s happening to me?”

My whole body was shaking like a leaf by now, and I pressed my eyes shut. I couldn’t look the objects of my perverted fantasies into the face, now that they knew of it. Something warm and moist slid against my thigh, and with horror I realised that it was Jen’s pussy.

The four of them giggled, and then my nightie was pulled up, exposing my breasts. My breathing stopped. Fingernails started to trail over my exposed stomach, slowly scratching their way upwards.

“Please,” I begged, “please stop.”

My pleading was answered with more giggles.

“Tell me Mandy,” Liz inquired, “what is the punishment for cheating? You didn’t say that when you explained the rules.”

“Let me go! Please! Let me go! You’re all crazy!” I demanded, but they ignored me.

“The punishment depends on the severity of the cheating. In this case…” Mandy thought for a minute, then giggled. “In this case, I’d say fifty swats on her bare bum.”

I couldn’t believe my ears. My best friend was collaborating to spank me with these girls!

“Don’t you think it should be fifty each,” Liz asked in return, “after all, she has cheated every one of us who has played her round?”

All the girls agreed while I wiggled and squirmed in their grasp. Suddenly, Mandy’s face was right in front of mine, and I stared at her with pleading eyes.

“Stop worrying, Penny,” she whispered, “just trust me. I’m your best friend. I’ll help you make your fantasies come true.” Then the hands released me, but time seemed to stand still. Suddenly her lips were on mine, her hot breath filling my mouth, her tongue forcing its way between my lips. I tried to shout my protest, but before I could do so, fingers gripped both of my nipples and squeezed them hard, making my energy rush out of me in a single gasp. They started to twist and pinch, sending painful needle pricks through my breasts.

Somehow, the pain was accompanied by a hot throbbing sensation that made my skin prickle all over, and a deep wave of need between my legs. I realised that I was kissing Mandy back, and the mortification almost made me faint. I was quickly losing control.

Someone started to tug on my pussy lips, rubbing them between their fingers, pulling them apart so I could feel cool air on my most private parts. It felt incredible, so demeaning and exhilarating at the same time.

A finger entered my pussy, fast and relentless, and I became aware that the pair of lips kissing me had changed, that it was now Liz’ tongue wrestling with mine, black lips pressing against mine. A fingernail scraped over my clit. At the same time, soft lips wrapped around my left nipple as started to suckle. I went over the edge.

Earthquakes raced through my body, and I lost all sense of time and space. I’d never had a climax of such intensity before, and I started to fear I’d die of pleasure, which sent me into a vicious cycle that had me convulsing under the shockwaves. The neighbours two streets down would probably have heard my uncoordinated cries of lust, if Liz wasn’t sealing my mouth with hers, shutting off most of my air supply. The finger in my pussy was pumping in and out like mad, and the pleasure seemed to go on and on.

I felt like floating, and small spots started to dance before my eyes. I could feel sweat erupting from all my pores. Finally, the waves ebbed and became short stabs, then twitches. The hands let go of my arms, or perhaps they had earlier, I couldn’t say. Jen’s weight left my legs, and Liz gave my lips a last, soft kiss. I curled up, my hands between my legs, an aftershock every now and then making me moan.

There was some talk going on around me, but I couldn’t care to listen. My world had just been turned upside down. And round and round, still spinning like mad. I couldn’t believe they had done that to me. And I could even less grasp my own reaction, the lust I had experienced at their ruthless treatment.

I turned to my back. All four of them were watching me intently, and I only now realised that my nightie was still bunched around my neck. Then Mandy reached out, holding my diary in front of me. Suddenly, she appeared shy.

“I - I think you had fun, Penny. But I think we should give you the option to quit. If you take your diary and go home now, we’ll never talk about it again. It’ll be like this has never happened.”

I was tempted to do so, but some wicked part of me held me back. “And - and if don’t?”

“Then we will continue with the game.”

“For tonight?”

It was Naomi who answered, her face right next to me, her breath stroking my cheek. “For as long as we like. Mandy will keep the diary, and it will be our means to keep you playing.”

“But what - what if I want to stop later?” I knew the answer, but I had to hear it.

“Then some of it is going to leak. Perhaps at school, or to someone who knows you well.”

“But that’s blackmail!”

“Is it really?” Mandy was curling a lock around her finger and looked innocently at me, still holding out the diary with her other hand. “I’d say its part of the game, and we’ll only continue if you want to.”

I fought with myself. Somewhere in my mind a little voice told me to take the opportunity and flee, that this game of theirs was insane. It was right. I slowly extended my trembling hand.

“Think if all the naughty things we could do with you, and make you do. Have you ever come like this before?” Naomi’s voice caressed my skin, and my arm went limp.

“Okay,” I rasped, “I’ll continue.”

I could see the eager smiles on their faces, and when Naomi whispered into my ear, “It’s spanking time, pretty Penny,” goosebumps raced up my spine.
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