Losing at Strip Mario Kart to my Sister

[jllash]

My older sister and I have always been competitive growing up, but one thing I always seemed to win was mario kart. Race after race I would win, sometimes 10-20 times before she ever won a race, and even then it was usually by pure chance because I was hit with a blue shell and multiple red shells at the last second. Nevertheless we still smack talked each other the entire time.

Over time, the busyness of life had created a wedge, we had got jobs in separate cities and now lived an hour away from each other, but we still met up every few weeks to have fun and catchup. Today was one of those days. After catching up over dinner and a few drinks she started the smack talk.

Her: "Ready to have your butt kicked in mario kart? I've been practicing and I know I'll beat you this time."
Me: "Oh ho ho, if you're so confident then how about we bet on it then?"
Her: "Money? I don't know..."
Me: "Hmm yeah on second thought I'd feel bad taking money from family. Hmm what else could we bet, I feel like it's boring without something on the line."
Her: (sarcastically) "Oh great so now you have a gambling addiction"
Me: "Hahaha you got me - here's an idea, how about we bet our dignity?"
Her: "Dignity? Like loser has to do something embarrassing like the chicken dance or something?"
Me: "Kind of, I mean like strip mario kart, loser has to remove an article of clothing, putting our dignity on the line, that way I can literally beat the pants off you haha"
Her: "Wow you're such a perv, I can't believe you'd suggest that. Like, you always win, so it's not even fair"
Me: "What happened to all that confidence you just had? Afraid you can't beat me anymore?"
Her: "Well duh, you win every time."
Me: "I guess that's true.. but you said you've been practicing and I don't know how good you are now, maybe you'll smoke me."
Her: (sarcastic) "Yeah right" "How about you play strip mario kart and I play regular mario kart, that way you get your high stakes and I don't lose my dignity"
Me: "Then I'd be risking my dignity for nothing, that's not fair, there's no point if it's only downsides for me"
Her: "Well the same goes for me too, I probably won't win, so it's only downsides"
Me: "Hmm, how about a handicap? If you win I remove 2 articles of clothing, and if you lose you only remove 1. Plus you're wearing a bra so you already have a clothing advantage."
Her: "You'd probably win like 10 times in a row, so that's still not much of a chance for me"
Me: "What do you think would be a fair handicap?"
Her: "Hmm..*she taps her finger to her chin thinking* since you always win, how about if I win once you have to strip everything, and if I lose I only remove 1 article of clothing at a time?"
Me: "Well that doesn't really seem fair, there's so much randomness in mario kart that I could lose at any time"
Her: "So with this handicap you're not sure you will win? Good. I'm not sure if I'll win either, so then that makes it a fair bet."
Me: "But erm, uhhhh I guess, I mean you do have a point... alright fine, let's do it. But lets set some ground rules first, no photos, this never leaves this room, and we're doing butt ass naked, not just down to undies"
Her: *shoots me a look* "What? Underwear not undignified enough for you?"
Me: "It's basically like a swimsuit and we're betting our dignity, so we have to do more than that"
Her: *A smile spreads on her face* "Fair enough. Alright. Get ready to strip!"

In the 1st race, I was nervous from the bet, I made some bad mistakes in the first lap and was losing. Much smack was thrown between us before muscle memory returned and I won the first race handedly.
Me: *Jumping up and doing a victory dance* "Woo! Guess all your practicing doesn't pay off! Take it off!"
Her: *Gives me a playful glare and says in a sing-song voice as she pulls off her sock and throws it at me* "All it takes is one loss" *Her sock falls to the floor*

The 2nd race continued smoothly, I won again and she removed another sock, I continued to tease her, but she still seemed confident.
The 3rd race was on Baby Park, a simple small oval track that was a nightmare of randomness, players in any position could throw an item and hit anyone. This track was where I had most of my losses.
I gulped as the countdown started, and right when it went green she said "I've been practicing this one".
I immediately became nervous but despite that I quickly took the lead and held it for the entire race. That is until the last lap, I accidentally hit a banana, I was still in 1st though and I limped past the last turn. Down to the final stretch and I was about to win when suddenly I'm overwhelmed with a blue shell, red shell, red shell, each one preventing me from moving, and that's when she passed me, crossing the finish line a split second before me.

She jumped up cheering and doing her own victory dance "I won! I won! I won!". All I could do was sit back, stunned at my loss while she had her moment of triumph. When she finally had enough she turned to me with a grin, "Strip!".

Me: "Urg, come on you barely won"
Her: *Smirking* "Huh? What was that last part again?"
Me: "You barely won?"
Her: "That's what I wanted to hear, I won! Now for my prize, your dignity" *She gestures toward me*
Me: "Fine.. a bet is a bet" *I pull off my shirt and pants, standing before her in my boxers* "There? Happy?"
Her: "Woo! Take it off!" she jeered, imitating my previous teasing. "Socks too!"
Me: *I kick off my socks with my feet*
Her: "annnnd your last article of clothing" *as she bounced on the balls of her feet and pointed to my boxers*
Me: "Are you serious?" *I feel my face getting warm from embarrassment and flustered*
Her: *grinning* "You said butt ass naked, you can't back out now"
Me: *With a sigh of defeat, I hook my thumbs into my boxer's waistband, bending over so my torso would provide some modesty and yanking them down and kicking them off my feet, quickly moving my hands to cover my privates. My nervousness has kept it flaccid and it was perched barely an inch long*
Her: "oop! I think I caught a glimpse of the little guy"
Me: "It's not little, it's average" *I keep both my hands fully clasped over myself*
Her: "Let me see then, move your hands"
Me: "No way, there was nothing in the rules about that"
Her: *She quickly encircles me to get a look at my backside before I have a chance to turn toward her* "Nice butt!" *she gives it a slap!*
Me: "Ouch!" *The slap makes me jump and instinctively move a few feet away from her but I maintain my hands on my privates*
Her: *Laughing hysterically*
Me: "Let's keep playing, come on give me a chance to make things even"
Her: "Why should I? What do I get if I win? I already have your dignity." *She smirks*
Me: "How about... if you win again I'll stand with your arms at my sides"
Her: "For 5 minutes"
Me: "No way.. uhh 10 seconds"
Her: "1 minute"
Me: "Fine"

And with that we continued to a 4th race. Still naked, I kept my controller over my crotch and leaned forward for modesty as we raced. It was much closer than the first 2 races but I managed to win. I celebrated with a hushed "yes!".
Her: "Too shy to do your victory dance now?"
Me: "Yeah I'm not dressed for it, now strip!"
She removed her pants, revealing a glimpse of cotton panties for a moment before she tugged the hem of her shirt down, it was just long enough to keep her panties completely covered.

Then it was time to race rainbow road. Everything went horribly wrong. I drove off the track early on and became flustered, continued to fall off multiple times, items were hitting me, and while she had her fair share of blunders, luck was on her side and she won.
She just looked at me with a grin and gestured at me to standup.
Her: "Time for the show"
Me: *I slowly stood up in the middle of the room facing her, hands firmly covering myself, I can feel my face going warm in embarrassment again*
Her: *She grabs her phone, tapping the screen a few times before standing up with it in her hand and looking me in the eyes* "Get ready to drop your hands, I'll start the timer in 3... 2... 1.. GO!"
Me: *I drop my hands, revealing my still flaccid state to her*
Her: *Her eyes drop and she bursts out laughing and grinning at the sight before her* "Is that all it is?"
Me: "Shut up" *My face burns in embarrassment*
Her: "Shut up shut up" she repeats mocking me in a high pitched voice before she kneels down and pokes it lightly with her pointer finger. "So smallll" *she bursts into a fit of giggles again, falling back on her elbows*
Me: "Hey don't poke it!"
Her: *She composes herself and stands up again and gets very close, resting her head against my shoulder, leaning her body up against me and draping her arms around my neck, her clothed boobs squish against my chest and bare legs rub against me*
Me: *I feel her thigh against my member and I can feel blood start to flow to it.* "Woah what are you-"
Her: *She leans in and whispers into my ear* "Can I tell you a secret?"
Me: *I become semi-erect against her thigh* "S-sure"
Her: *She whispers* "If I was down to just my underwear, then I would have stopped playing, you never had a chance of taking my dignity"
Me: *My eyes widen and my jaw drops as the realization swept over me, I had walked right into an unwinnable bet.*
Her: *She steps back with a triumphant smirk on her face*
Me: "You played me!"
Her: "Hey making the bet 'butt ass naked' was your idea, it's not my fault you lost. You. Played. Yourself" *She says with a sing-song tune, pausing after each word for emphasis while staring him in the eye. She is thrilled at the poetic justice of the whole thing*
Me: *I open my mouth to shoot back but then close my mouth. She was right, and there was nothing I could say to change that*
Her: *she looks down at my now erect member and says to herself* "huh, bigger now" *her smirk turns into a grin*
Me: *I blush* "It's purely a physiological reaction"
Her: "Uh huh, sure... Oh and one more thing, I got this all on video" *She turns around and holds up her phone as if she was taking a selfie with me, the screen shows it's been recording for the past minute. She hadn't started a timer, that was when she started the video!*
Me: *I reach out and try to snatch it from her hands* "OMG are you kidding me delete that"
Her: *She moves out of reach* "nooo way, this is my insurance, I want you to always remember that I'm the mario kart champion, and this here is proof of that. Now I want to hear you say it, or else this is getting blasted all over the internet" *she holds the phone up, pointing the camera at me*
Me: "OK yes whatever, you're the mario kart champion just don't post that"
Her: "And don't you forget it!" *She gives me a wink, ends the video, and unexpectedly gives my member a single quick playful tug*
Me: *I blush and quickly put my hands over it and stand there awkwardly as she pulls her pants and socks back on.* "So you won't show anyone that video, right?"
Her: *She gives me a devilish smile* "Don't worry, maybe I'll show some of my girl friends, but I won't send it as long as I stay the mario kart champion.. for now."

[Freesub]

Maybe you could mention the ages of the characters? Other than that, good story

[Supermario17]

Great story. Hopefully another one coming in the same verse.

[Fayni]

Maybe you could mention the ages of the characters? Other than that, good story

Not sure the age is really necessary. That kind of story could happen as well as 15 or 25 old, and it doesn't change anything, except you can imagine the age you want ^^

[dublinjohn]

Maybe you could mention the ages of the characters? Other than that, good story

Over time, the busyness of life had created a wedge, we had got jobs in separate cities and now lived an hour away from each other, but we still met up every few weeks to have fun and catchup. Today was one of those days. After catching up over dinner and a few drinks she started the smack talk.

I would guess 20's or 30's


I don't usually go for ENM, but this was a good story idea

[jllash]

Yeah I didn't have specific ages in mind, general thought was anywhere 20-30s, but as Fayni mentioned, it could work just as well at 15 (without the preamble)

[lovaboitoy]

Hot story I like she embarrassed him good with she was never getting naked and win win for her

[jllash]

(continued)

"Okay, Jessica," I began, trying to keep the tremor out of my voice. "I really don't want that video around, what do I have to do to get you to delete it?"

Jessica leaned back on the couch, a smug smirk playing on her lips. She tapped her chin thoughtfully, as if she hadn't already thought this through. "Well, you know I'm not the type to just give things up for free."

I clenched my fists, feeling the blood rush to my face. "What do you want?"

Jessica's eyes sparkled with mischief. "How about another bet? The stakes will have to be very high though, I can't just give up this treasured video, it will have to be of something equally valuable."

I took a deep breath, trying to compose myself. "What do you have in mind?"

Her smile grew wider as she leaned in closer. "Let's make this interesting," she said. "If you can beat me five times in a row, I'll delete the video and we'll call it even. But, for every time you lose, you'll have to do something... special."

My heart sank, knowing full well that 'special' didn't bode well for me. "And what's that?" I asked, bracing myself for the worst.

"If you lose," she said, "you have to perform a little task for me. Nothing too hard, just something that lets me keep a piece of your dignity. But you won't get to know what it is until you lose." She held up her phone, the video of me standing stark naked with my hands at my sides playing on the screen.

I blushed furiously, the heat in my cheeks almost matching the fluster in my chest. The sight of the video was mortifying, a stark reminder of my defeat. But I had to make sure it was deleted, no matter the cost. "Okay," I swallowed hard, hoping I wouldn't regret it.

Jessica watched as I reached for my boxers, the soft fabric feeling like a lifeline back to modesty. "Nope," she said, her voice light, almost musical in its cruelty. "No getting dressed. You're playing like this."

"What?" I sputtered, the color draining from my face. "But I thought the strip part of the game was over."

Jessica giggled, a sound that made my stomach drop. "Oh no," she said, "If you want your dignity back, you're going to have to earn it."

Feeling utterly embarrassed and with no other choice, I backed down, sitting on the couch next to her. I grabbed the controller, trying to ignore the cool air brushing against my exposed skin. I had to play it cool, I told myself, focusing on the game and not on the fact that I was sitting butt naked next to my sister. I leaned forward slightly, using my torso and my arms creating a makeshift barrier around my crotch, hoping to shield my penis from her view.

The next four races were a blur of pure adrenaline. The blue shells flew, banana peels scattered, and we both fought tooth and nail. Jessica giggled throughout even as I managed to pull off victory after victory. Each time I won a race she'd smile and look me over, just enjoying the situation she found herself in. I became increasingly anxious as we approached the fifth and final race. This was it, the moment I had to win to reclaim my dignity.

My eyes remained glued to the screen, my thumbs moving almost on their own. Jessica had become increasingly cheeky over the last race. Her hand brushed against my bare thigh as she leaned in to whisper taunts, sending shivers down my spine. She knew exactly what she was doing, and I was playing right into her hands.

As we approached the final stretch of the fifth race, the tension in the air was thick. I was in the lead, and victory was within grasp. But then, she did the unthinkable. With a swift motion, she lifted my arm, creating a vulnerable opening in my makeshift barrier to shield my nakedness from her. Her hand darted out, and before I could react, she touched my penis, her fingertips danced playfully and feather-light on my sensitive skin for a brief moment, before withdrawing immediately. I jolted upright in surprise, my concentration shattering like a cheap plastic bowl.

My character on screen swerved wildly, and my eyes shot from the TV to her, trying to process what was happening. She giggled again. "What are you doing?" I hissed, my voice strangled with a mix of fear and embarrassment.

"Creating the perfect distraction," she said, her eyes gleaming with amusement as her character soars over the finish line, defeating me.

My heart sank as the game announced her victory. "What's the forfeit?" I whispered, my voice tight with apprehension.

Jessica's smile grew wider, if that was even possible. "Remember Brittany?" she asked, her voice taking on a teasing lilt. I felt a cold knot form in my stomach. Of course, I remembered Brittany, my sister's best friend. She had always been around, a constant presence in our lives, and a thorn in my side. I nodded warily, not liking where this was going.

"Well, I'm celebrating her birthday next week," Jessica announced, her eyes sparkling with an idea that I knew I wasn't going to like. "And since you're feeling so generous, I think you should wish her a happy birthday in a very... special way."

My mind raced, trying to piece together the horror show she had planned. "What are you talking about?" I managed to croak out, my throat dry with dread.

Jessica's grin grew more wicked by the second. "Oh, it's simple," she began, her eyes gleaming with excitement. "You're going to make a birthday video for Brittany. But not just any video. You're going to wish her a happy birthday in your birthday suit on video call."

I stared at her in horror, my cheeks burning with a mix of humiliation and anger. "You're kidding, right?" I whispered, hoping against hope that this was just a joke.

Jessica's smile grew wider. "Do I look like I'm kidding?" she asked, holding up her phone, ready to call Brittany for the next phase of my humiliation.

Panic set in as I searched for a way out. "Jessica, come on, this is going too far!" I protested, my voice rising slightly.

But she was enjoying this way too much. "Don't worry," she said, her eyes gleaming with excitement. "You're just going to be like, 'Surprise! It's a naked birthday greeting!' It'll be hilarious."

I couldn't believe what I was hearing. "Jessica, please, you can't be serious."

Her eyes held mine, and I saw the determination in them. "Oh, I'm dead serious," she said, her voice dripping with amusement. "Besides, Brittany's always thought you were cute. She'd absolutely love it."

The thought of Brittany seeing me like this was more than I could bear. "Can I at least cover my... you know," I stuttered, gesturing awkwardly at my crotch.

"Fine," she said with a smug smile. "But when you cheer 'Happy Birthday,' you have to put your arms up in the air. That's the best deal you'll get."

I groaned in defeat, the weight of my predicament pressing down on my shoulders like a heavy burden. With no other option, I reluctantly agreed.

Jessica's fingers flew over the screen of her phone, her eyes gleaming with excitement as she video called Brittany. The phone rang, and I could feel my heart hammering in my chest. She kept the call focused on her own face at first, giving me a brief moment to mentally prepare for the humiliation that was about to unfold.

"Hey, Brittany, it's Jessica," she chirped into the phone, her tone as bright as the day. "I've got a little surprise for you. I know it's a little bit early but you're not going to believe who's here to wish you a happy birthday." She turned the camera to me, and I felt my cheeks burn brighter than the sun.

With a dramatic flair, Jessica raised up the phone and pointed it at me, standing there with my hands covering my junk.

"Surprise!" Jessica sang into the phone, her eyes glinting with amusement.

On the screen, Brittany's eyes went wide with shock and confusion, her mouth forming an 'o' as she took in the sight of me standing in the background, my nakedness barely covered by my trembling hands. My eyes darted to the preview, where a small image of my entire exposed body was entirely in frame, then back to her face. She had the biggest grin now, the realization that she was about to witness a live, and very unwilling, nude performance from her best friend's little brother was clearly written all over her face.

"H-hey, Brittany," I mumbled awkwardly, feeling a wave of heat wash over me. My voice cracked, and I shifted my weight from one foot to the other, trying to find some semblance of comfort or dignity.

Brittany's shock quickly morphed into uncontrollable laughter, her eyes watering as she took in the scene. "Oh my god, he's naked!" she choked out between giggles.

Jessica couldn't resist the urge to join in. "Yep, he's all yours for a birthday greeting!" she exclaimed, panning the phone up and down my body.

I gritted my teeth and took a deep breath, knowing I had to go through with it. I forced a smile and raised my arms in the air, revealing my bare genitals. "Happy Birthday, Brittany!" I shouted, desperate to get this over with.

Brittany's laughter grew even louder, her eyes flickering between shock and amusement. "Oh my god, this is the best present ever!" she exclaimed, her cheeks turning a delightful shade of pink.

Jessica couldn't contain her glee. "Isn't it?" she said, turning the phone back to her own face. "Just remember, you owe me big time for this."

My face burned with a humiliation that I had never felt before. It was bad enough to be naked, on display for my sister's entertainment, but now I had exposed myself to her best friend, a girl I grew up with, who I knew my whole life.

"Alright, that's enough naked birthday wishes, I'll talk to you laterrrrrr," Jessica said after a few moments of Brittany's hysterical laughter. She ended the call and turned to me, her eyes gleaming with victory. "Now, that's a memory she won't forget anytime soon."

My cheeks burned with embarrassment, and my body felt like it was on fire. I couldn't believe Jessica had just done that. "Can you just delete the video now?" I asked, desperation lacing my voice.

Jessica's smile didn't waver. "Now why would I do that?" she asked, her voice dripping with fake innocence. "You didn't win the bet. But I'll give you another chance, how about another bet?"

[Jeepman89]

Love the naked birthday wishes!

[Lola]

Awesome how she distracts him! It feels so good that he is playing naked. Can't wait to read more