The Dare by Octopussy

Want More from Octopussy?

Find her over on FCF!

I struggled to remember how it was that I found myself in this exact position. Laying on my back, Claire straddling my midsection, hands wrapped around my wrists pinning them above my head while I stared up at her sports-bra covered D-cup breasts while she mocked me.

“You can give up any time,” Claire said with a giggle as she bounced her ass on my stomach a couple times to punctuate every word. I thought back, it was just two months ago we were meeting the Roses and now I’ve got one right on top of me…

Two Months Prior

“Welcome into our new home! So glad you could join us!” Jason said as Dave and I walked through the front door of the neighborhood’s newest additions, Claire and Jason Rose. The couple was a transplant from Pittsburgh, Claire having gotten a Senior VP job here in New Orleans and Jason being hired on as a high school football coach with aspirations for a college job one day.

They’d lived in the neighborhood for less than two weeks when an ornate invitation arrived in our mailbox, “The Roses want to help us welcome them to the neighborhood. They’re throwing a house-warming/get to know everyone party on Saturday the 19th,” Dave said as he looked over the invitation and passed it along to me. We had seen the new couple in passing a few times, out on jogs, in the Whole Foods down the corner, and were always very friendly, waving and welcoming them, but never having a good opportunity to formally get to know them. I thought this sounded like a great idea, so I agreed with Dave that we’d go.

As we entered the house the first thing that caught me was Jason’s attractiveness. Always passing him out and about I never got the chance to stop and look at him, but the man was striking. Dressed in a fine tailored suit, chiseled chin, soft blue eyes, dark mussed hair, and a scruffy beard, he looked like he could be straight out of central casting. When he spoke his voice carried with it a power that made it clear, when he was coaching his was the only voice that the players ever need listen to.

We slipped farther into the house and spotted Claire, standing in the sitting room with a few of our neighbors gathered around listening as she told a story about a merger she’d squashed because it turned out the CFO from the other company had been cooking the books for the better part of 10 years and their accountants had never discovered it. It took Claire less than 2 weeks looking over their books during the mergers to discover the discrepancies and now the CFO is on trial for fraud, tax evasion, and for good measure child support as his wife had since divorced him.

As we joined the group of neighbors Claire caught my eye and I had to admit that she held it for as long as I dared hold the gaze before looking away. Claire’s emerald green eyes were a perfect match for her auburn tresses. She stood a statuesque 5’9” without the 4” heels she was wearing to go with the midnight blue cocktail dress that clung to her curves. The dress shimmered in just the right way when she turned into the light to make it look like stars on a lightless night. I would find out later that she clocked in at a perfectly petite 124lbs, a near mirror to my 120lbs, though I carried much less height at only 5’5”.

After finishing her tale she waved us over, “Rebecca, Dave, so happy to have you in our home! It is a pleasure to finally meet you and not just breeze past you on our runs,” Claire said with a smile though her words, for some weird reason, caught me off guard. “Breeze past you” what was that supposed to mean? I shook it off and took her hand, shaking it and giving her a light hug before Dave kissed her hand like we were in some sort of mid-century English play. I gave him a playful poke in the ribs afterward and we continued through the evening’s festivities.

As the evening went along I found myself constantly gravitating toward one of the home owners. Every time I’d break away from one conversation, I would somehow end up with the other one was holding court. It was like some sort of magnet was driving me toward them every chance I got. What came out of that was a budding friendship with the new neighbors that would extend for the next two months.  With the party winding down well after midnight, Dave and I agreed to invite Claire and Jason over next weekend for dinner and drinks.

This ended up becoming a tradition it seemed. Every weekend, either Friday, Saturday, or Sunday night was spent at their house or ours, dining, drinking, regaling stories of our misspent youth, our current jobs (I was a corporate accountant and Dave was head of cyber security for a Fortune 200 company), our future family aspirations. Anything you could think of, it was fair game. The later the evenings got, the more wine (or whiskey) we’d consumed the more raunchy and naughty our conversations became. We would talk about past partners (I was never jealous. I knew Dave loved me and Dave knew the same. It seemed Claire and Jason felt likewise), fantasies in the bedroom, and all manner of different devious acts. My favorite was shocking Claire and Jason by recounting the time Dave and I had a quickie in the Empire State Building’s elevator, hoping that it wouldn’t make a stop before we finished. We got lucky and finished three floors before it stopped again.

Fast forward to last night and this is how we arrive at our problem. Dave and Jason are joking and getting ready to get into their hot tub, a nightly tradition by now, as Claire and I were changing into our bikinis. I hear Jason call out “Claire, what was the name of that girl you beat up in college?”

“Oh god.” Claire said, blushing instantly as she looked at me and I just smiled. “Denise, why?” Claire called down as we finished changing and moved to join the gentlemen in the hot tub.

“I was just wondering. Dave and I were talking about fantasies and he mentioned that one of his greatest unfulfilled fantasies was seeing two women fight. So I got to one-up their Empire State Building story with the tale of you kicking Denise’s ass!” Jason said with a laugh and a flourish of his hands.

“Oh stop it Jason, it was hardly me kicking her ass. We’d gotten drunk at the bar, she bumped into me and spilled my drink, so I slapped her. One thing led to another and next thing I know I’m being carried out by the bouncer, my right fist alight with pain, and my left fist full of a chunk of her hair. Turns out I knocked her out. I felt pretty bad about it once I’d sobered up.” Claire told us the story and I could see Dave hang on every word. I’d always known female fights were a passion of his, but just never found the right avenue to pursue it. That seemed to be the end of it and the night continued uninterrupted with more laughter and talk of college mistakes. I got up to grab another bottle of wine and stopped dead in my tracks when Dave blurted out an alcohol-induced statement that brought the conversation grinding to a halt.

“I bet Rebecca could beat Claire!” Dave announced proudly. I quickly pivoted on my heel to give him a death stare and I could see the redness in his cheeks that told me he was no longer Sober Dave and had progressed to Tipsy-Say-What-I-Want-Don’t-Give-A-Fuck Dave. This was going to be an interesting conversation.

“I’m sorry for Dave, he gets STUPID when he gets drunk,” I said with a giggle while Dave flipped me off from the hot tub. I threw the cork at him and laughed as Claire and Jason laughed right along with me.

I’d returned to the tub with the new bottle and thought we were just going to let things go when Claire decided to feed Dave. “You think so, Dave? Your wife looks strong, no doubt those mornings at the gym are paying off, but I don’t think she’s got what it takes to pin me down.” She said with a cheshire cat grin on her face and intentionally avoiding eye contact with me while staring Dave down. I watched Jason shift uncomfortably in his seat looking back and forth between the three of us as my eyes shifted from Dave to Claire repeatedly.

“This is stupid, I’m pouring myself another glass of wine and YOU are picking a new topic,” I said to Dave as I thrust the bottle into his hand and slapped the back of his head playfully. At that moment Claire burst into laughter.

“You should have seen your faces! I wasn’t sure who was going to pop first, you from anger, Bec, or you from the mental picture you were getting in your head, Dave!” Claire said through giggle fits as she sat back down in the hot tub and we all relaxed and had a good laugh.

Another glass of wine and I was feeling I don’t give a fuck tipsy, and decided to have a little fun of my own. “Truth or dare, Jason.” I asked without batting an eyelash. Jason locked eyes with me, a playful look on my face as Claire watched him out of the corner of hers. “Nahhh not gonna do it. Truth,” he said with a wry almost embarrassed look on his face.

“What’s the dumbest thing you’ve done that you’ve never told anyone?” I asked. And Jason answered which left us all in tears at how he was still alive. “OH. MY. GOD! How did I never know that about you, you IDIOT!” Claire said in delight as Jason told his story. Thus began the game of Truth or Dare that would lead to my current fate.

Six or eight questions in it was Claire’s turn and she looked at Dave who’d just dared Claire to perform a lap dance on Jason to classical music. (Dave was fun when he got drunk, usually.) It was hilarious to watch a lap dance to Bach’s Overture No. 3 but Claire was looking like she wanted payback. The rules, of course, were that you couldn’t hit up the person who had just been the asker, so I knew it was coming my direction. I steeled myself for it and sure enough, “truth or dare, Rebecca?” Came Claire’s sing-song voice.

“I did truth last time I think, so fuck it Claire, do your worst. DARE!” I said with a little exaggeration for fun. She mulled things over and then her eyes lit up and I got legitimately scared. “I’m not running around the house naked!” I blurted out as her smile widened.

“Oh no no no, nothing like that. Dave would have my head for that,” she said before her face turned ever so slightly more serious. “I dare you, Rebecca Miller, to wrestle me in front of our husbands.”

What followed was straight out of a cartoon. Jason’s jaw hit the floor, Dave’s eyes popped out of his skull, and steam erupted from my ears. I had no choice. I’d been dared. What could I say? How could I back out? How much alcohol had I consumed that I wanted to say yes!?

“I accept your dare, but not tonight. It’s late, we have ALL had too much to drink, and we need to be sober to properly ensure nobody gets hurt or goes to far.” I said trying to be the voice of reason. Claire agreed and we decided to call it a night, agreeing to meet the very next day to go over everything.

After sleeping until noon to stave off a hangover from the wine, I awoke to a text from Claire “hitting the gym at 12:30 then I’ll head over with Jason and we can discuss things.” I replied back “Want a gym partner? I need to work off that wine!”  We spent the next 45 minutes working out, mostly cardio, and chit chatting with each other between sets or during cool downs, but never discussing the dare that had been made the previous night. We both felt that the men should be there for everything. We showered at the gym and climbed into Claire’s Audi to head back to my place where Jason and Dave had prepared lunch.

As we ate Claire began the proceedings. “Here’s what I was thinking and you can wave me off whenever you want. Friendly wrestling, no punching, no kicking, no biting, no being overly MEAN to each other, just two women testing the other’s strength and ability. I don’t want to claw your eyes out and I don’t want you to punch my lights out!” Claire started and I nodded my head in agreement while both men hung on every word. “Sports bras and shorts, the same thing we just worked out in, no wardrobe malfunctions needed, these D’s don’t need to be bouncing around in front of Dave and making you all jealous.”

I instinctively looked down at my smaller C cup tits and frowned/blushed at Claire’s words as she laughed “We’ve seen each other naked Rebecca, yours are incredible and you have nothing to be ashamed of!”

The discussion continued and we came up with the rules. 60 minutes of wrestling with a 5-minute break (the clock wouldn’t run during breaks) after each 5-second pin or submission. At any point one of the women could call the match off completely by saying the other woman was the better woman. Each woman would be granted a single time-out to use at their discretion and both women would instantly stop, part ways, there would be a 2.5 minute break and then action would resume from a neutral kneeling position. If the match goes the full 60 minutes most submissions and pinfalls wins.

We agreed to the rules and also agreed that we’d do it right now. Both of us were feeling amped up after our workout and the boys wouldn’t have let us leave I don’t think, if we didn’t engage right now. Fast forward 15 minutes and we find ourselves where we currently are. Claire mounting my stomach, her D’s in my face, already having a 2-0 advantage after wrestling me into a body scissors and then holding me down in a grapevine pin. She’s looking to take a 3-0 lead and cement herself as the more dominant and skilled woman. Given my size disadvantage in both height and weight I felt I’d given her a good fight, she was just managing to get the better of me in small quick exchanges that left me in bad positions overall and led to her taking a 2-0 lead.

I growled up at her “Shuddup!” I hissed and then bucked hard, flinging my hips up into the air to try and send her sprawling off me, but she just rode me like a cowgirl and then slammed her ass down into my stomach again, dropping me back to the floor with a huff. “I like it when I’m on top and Jason tries to unseat me. It’s one of our favorite games. I haven’t lost his cock yet!” She says with another smile and I groan out, already sweating heavily and struggling against the taller woman. Jason counts out and soon enough “FIVE” and that’s it. I’m down 3-0 and Claire is loving every second of it.

We both go to the corners where our men are standing with water and advice. I sit on the barstool we’ve got set up and take a huge drink of water while Dave tries to give me advice. “You’re not doing terribly, just try to react quicker to her moves. It’s nothing special that she’s doing, she’s just out-thinking you a bit.”

“Yea thanks, I hadn’t noticed,” I said with an eye roll before taking another drink of water and catching my breath. I grabbed a towel and dabbed the sweat off  the tops of my tits scrunched into my sports bra, and my abdomen which was a mix of my sweat and Claire’s which had rubbed off during her ass-bouncing exhibition.

The timer rang and we both took to our feet and moved back toward the center of the living room. I looked the statuesque woman over and brushed my blonde hair over my shoulder “this is my round” I say with a bit of false bravado as we close in and Jason re-starts the timer. God still 40 minutes left and already I feel like this is the hardest workout I’ve ever had.

Claire lunges toward me, reaching for my left wrist and I yank it back as I push forward, twisting my hips and throwing my right arm around Claire’s head, tucking her into a headlock as I press her face in against my side. I can hear Claire grunting as she pushes against my hips with both hands but I manage to lock the headlock on nice and tight, squeezing her head against my body. I need to take her to the ground, I think to myself, as I decide the best way to do that is with momentum. I stick my hip out into her midsection, plant both feet, twist my body, and end up flipping her over my hip and bringing us crashing down onto the carpeted floor with me landing firmly on top of Claire’s bountiful D’s and knocking the breath out of her.

The move winds Claire and I’m able to hold the headlock in tight, torqueing her neck and going for a submission. Unfortunately for me, Claire’s crafty and she kicks her long legs up and wraps them around my head, snapping those tight legs shut in a head scissors and yanking them, and me, back down to the ground, forcing me to give up the headlock I’d applied. I grunt as I roll away from Claire’s head, trapped between her scissors. I manage to think quickly, and continue rolling, and as luck would have it, slipped my head right out from between her scissors as I hit the ground and rolled down to her ankles, which I straddle and keep her legs pinned under me.

I look up as Claire sits up with me holding her legs straight out in front of her. I am slightly confused on where to go from here but Claire gives me an idea as she reaches out for me. I grasp both of her hands and yank them forward while sliding up her legs, pulling her upper body to me. As she approaches, my arms fly out and surround her upper body, pulling her taut to me and squeezing down hard on her, wrapping her up in a seated bear hug, our breasts mashed together in surprising discomfort and yet providing some sort of spark in me I’d never felt before. I squeeze with everything I’ve got, grabbing my forearms with both hands and trying to crush the wind right out of her, my face next to her ear. “Give up Claire, I’ve got you trapped and you can’t get a full breath!” I whisper into her ear so only she can hear.

A couple more pumps of my biceps, jolting her upper body I feel her head slump against my shoulder and she says “I give up.” I instantly let go of her and ease the woman down to her back, before dismounting and walking back over to my stool and taking a drink. I look at the clock 32 minutes left. That took 8 minutes and I’m still down 3-1. I need to keep working her in order to wear her down and get more submissions, I think to myself as Dave continues to try to give me advice.

The five minute timer is done in a flash and Claire and I are back up facing each other once again. I think of what my next move should be as we face each other. Before I can come up with something Claire raises both hands above her head and wiggles her fingers. She’s taller, heavier, and I know stronger, but she’s offering a test of strength and I can’t say no. I growl at myself for agreeing and raise my hands to interlock my fingers with hers, Dave shouting encouragement and Jason doing the same as we lock up and our upper bodies flair with definition as we both struggle against one another. She’s stronger no doubt, but I manage to hold my own, keeping her from gaining any sort of advantage, which surprises both of us. Claire lifts herself up to her tip toes and tries to gain extra leverage but before she bear down on me I take a step back and yank her hands forward, pulling her off balance and watching as she ends up on her knees in front of me, both of her hands still tied up in mine. I take a step forward, my crotch ending up close to her face as I keep a grip on her wrists and start to bend her hands backwards and watch as she folds back under the pressure, grunting and groaning in pain.

I continue to push forward, bending her back until I can place a leg on either side of her midsection, and then I yank her up, forcing her torso between my thighs. “Let’s go for a little squeeze” I say, full of confidence as I enclose my thick thighs, easily my best asset, around her torso and begin to squeeze down. Claire throws her head back in pain and instantly starts crying out her submission, “I GIVE I GIVE!” she cries, and once again I quickly release her.

Taking another glance at the clock and that submission only took four minutes, we’re down to 28 but it’s 3-2 and I feel like I’m gaining some momentum. I watch as Jason and Claire are having a spirited discussion about me and my technique while Dave rubs me down and feeds me water, reminding me to watch for Claire’s length and that she’s probably planning something for me in this next round.

The round break ends and I get to my feet, muscles protesting, maybe cardio wasn’t the best idea before a 60-minute wrestling match! Not much I can do about it now though as we both step toward each other and Jason starts the clock again. Claire gives me a look and raises her hands up again “you got lucky last time, we both know I’m stronger, and I’m going to prove it,” she says as she wiggles her fingers in my face.

I did get lucky last time, it was a good move but she should have seen it coming. I know I won’t be so lucky this time, but I agree to it anyways. I raise my hands right as my fingers start to touch her skin she drops her hands, slips forward under my right arm, and as I try to bring my arms down she is pulling hers up my sides. My arms  end up hooked on hers, her biceps fitting into my armpits and her hands wrapping around behind my head. She’s got me locked in a full nelson and instantly I know this is bad. I twist my torso, stomp my feet, protest with my words, but she’s got me locked, her height allowing her to lord over me and push my head down until I’m staring straight down at my cotton-covered c-cup tits.

I get paraded around, Claire forcing me whichever direction she wants, and any time I protest she squeezes her biceps together and shakes my upper body, literally shaking the fight right out of me each time. She taunts me a little, all friendly of course, but it stings right now, the words echoing in my brain as I cannot break free.

We move toward the center of the room and she drives her knee into the back of my left thigh, dead-legging me and dropping me, and her, down to our knees, which was exactly what she wanted. “Should I make you submit, or just hold you like this for the remainder of the time?” She asks playfully in my ear before falling backwards from her knees onto her ass, bringing me with her. My ass pressed tightly to her crotch and each time I wiggle it I’m wiggling right up against her womanhood unintentionally. She coos in my ear “I think I liked what you did last time,” and I feel her long legs snaking around my midsection, just above my hips, her hands still pressing down on the back of my head, putting pressure on my neck, my arms starting to go dead, held up above my head for so long.

I feel her legs start to coil tightly around my waist, her thighs beginning to dig in, but she does it slowly, methodically, and I know she’s milking the clock because she’s got me in a bad position. I struggle and wiggle my body, trying to break free but it’s no use, each time I do she pumps her thighs or pushes my head or flexes her biceps and I am forced right back into a docile position. Her legs get tighter and tighter until finally she pumps them hard around me, locks her ankles, and I’m forced to cry out my submission “I GIVEEEEE” I squeal as the pain in my torso becomes overwhelming.

Claire quickly eases up on both holds and lets me down to the carpet gently. I lay there for a good 3 of the 5 minutes, my arms getting blood back to them and taking forever to recover as I struggle to finally push myself up and get to my stool. My arms feel like noodles and down 4-2 I don’t even want to look at the clock. When I do I gasp. EIGHT MINUTES! She had me in that hold for almost 20 minutes, no wonder my arms feel like jell-o and I can’t get them to do what I want!

The 5-minute break ends way too quickly and before I know it I’m back on my feet, trying to get my arms to work properly. They lift but feel like they’re attached to sand bags. “I’m sorry Rebecca, don’t worry this will all be over soon,” Claire says, almost like she regrets beating me, but beating me she is. I throw caution to the wind and launch myself at her, trying to drive my body into hers and knock her back to the couch but my body just isn’t responding like I want. I push forward and actually surprise Claire, but there’s no power left in it and as my body pushes into hers she quickly and easily twists us and we end up with me being thrown onto the couch and Claire standing over me.

She quickly grabs both ankles and pulls me off the couch and onto the carpeted floor before twisting me over. I protest and try to fight it but she’s stronger and fresher than I could ever hope to be by now and quickly she gets me onto my back. Claire holds my ankles and steps over my body, folding me up as she bends me into a sort of a C and works me into a boston crab. At this point she’s not trying to hurt me, or even get me to submit, she’s just trying to control me until the timer runs out. “You fought well, Rebecca, but this just wasn’t your night,” Claire tells me as she holds me down and Jason calls out “Five minutes left!”

I have two options, be trapped in this hold for another 5 minutes, or admit that she’s the better woman. I struggle valiantly, shaking my body reaching back and pushing on her back, trying to twist my torso to free myself, but none of it works. She holds me still, trapped in this hold as I slap the ground, not in submission but frustration, struggling to come to grips with the fact that Claire has not only beaten me, but beaten me soundly. The timer finally goes off with a loud BUZZZZZZ and Claire eases up on the hold, letting me flop back down to the carpet where I remain, a couple tears pushing free as I lay, embarrassed, in my own home.

Claire quickly comes to console me and we share a hug before agreeing to talk again next weekend.

My first wrestling match, and it was a failure. I tell Dave later that night that I let him down and he tells me I’m being silly, that there’s nothing I could do to let him down, but I don’t believe him. I have to make it up to him, and there’s only one solution. I have to beat Claire Rose.

The End.

Thank you for reading! For more stories: Click Here!

Leave a Reply

Your email address will not be published. Required fields are marked *

Some of the images seen on this site have been provided by BattleBelles.com and CatfightFactory.com
Skip to toolbar