Double or Nothing with Ellie

First (maybe last) story. Had to write it when inspired. I know it’s super long, but I always like stories better when the plot and characters matter. The fun starts where the section break is if you’d like to skip.

Tw: mild dubious consent at one point, nothing too bad.


DOUBLE OR NOTHING

It was the end of my second year of med school. Having worked for a few years between undergrad and med school, I was a hair older than the plurality of my classmates, but not by much and not by enough that it hurt my ability to make friends. But it did mean (at least I think so) I was also a hair more mature than most of those who went straight from kindergarten through to med school without stopping to work for a year or two. I think that real world experience gives you a sense of what matters and what doesn’t. 

Nowhere was that more clear than with my friend Ellie. Ellie is, to this day, the smartest person I’ve ever known and still a great friend. But she is an absolutely psycho. 

Physically, Ellie was pretty tall. I’d say around 5’9”. She was thin from her constant time on the treadmill, but genetics blessed her with solid C-cups which sat high and firm on her frame. Her ass was incredible from all that time in the gym. And her long long legs were strong, especially after she decided out of nowhere that she was going to run her first ever marathon next month and needed to start training for distance. She had no problem completing that marathon, by the way. 

Mentally, she was gifted. She was a total disorganized mess who didn’t keep up with the reading, but somehow almost never got less than an A. We’d be be hours before the exam, and I’d be explaining to her concepts I had internalized months ago in the course of my consistent studying and outlining. I’d always be sure she was headed right for disaster, having procrastinated til the very end. And then every time- or almost every time- she’d get an A on the exam without having even put the effort in.  

Ellie was a competitionaholic. School was a competition. Driving to a restaurant with our friend group was a race. Eating the spiciest food at dinner was a contest. And if you didn’t want to compete? Well, you’re a pussy! 

It really got messy when you beat her. Some people love to win. But Ellie hated to lose. And you’d think because she hated to lose, she’d only pick competitions she could win. But no. She was so obsessed with competing she’d routinely make challenges she could never possibly win. She challenged the D1 sprinter to a footrace. Despite being all cardio and no lifting, she challenge to gym bro to a pull up challenge. But if you beat her, even if it was obvious from the beginning to were going to win, it was a technicality, or you got lucky, or you had to go double or nothing on something else. And if you didn’t want to go double or nothing? Well, you’re a pussy! So frustrating. 

Despite that quirk, she was a great friend and a great hang. Loved sports and beers, always happy to wingwoman you at the bar and do anything she could to help you. My relationship with Ellie was entirely platonic, and I never even bothered to have a crush on her. Not that I wouldn’t want to give it a shot, if I had the chance. But she was way out of my league.  Sure I was around 6’ tall with a very likable personality, but I wasn’t in the best shape of my life and Ellie only dated guys who were absolutely ripped and her age. She said she wanted her kids someday to be pro athletes. 

On that fateful day, Ellie and I had just finished our last final of the semester. That wasn’t enough competition for her, though. She wanted to play some 1 on 1 hoops. There was a court at her apartment complex. I really just wanted to relax with a tall glass of wine, but, as usual, Ellie badgered me til I agreed to play to shut her up. She always seemed to get her way. 

Basketball between us was usually a fair fight. She played in D3, but I was a pretty accomplished high school player who had a few inches and a ton of weight and strength on her. I arrived at the court in loose basketball shorts and a t-shirt. Ellie had short biker shorts with a very loose tank top over a highlighter green sports bra. As typical, I appreciated the eye candy for a moment, reminded myself she'd never go for me, and focused on the game.  

Before we started, Ellie said she wanted to make it interesting. As broke students, the most we could agree on was 50 bucks. I give her first ball and we were off. 

It was just one of those days for Ellie. Nothing seemed to fall for her. I don’t remember the final score, but it was a frustrating game for her. But Ellie never stopped the shit talk til I hit 21. I smiled and said I’d look for the $50 on Venmo. But Ellie did what she always did. She demanded double or nothing. 

It was too late for more basketball, and I was tired. I tried to refuse. Ellie, perhaps sensing my hesitancy and desperate to exploit anything she could to stop me from leaving and make the loss official, took off her tank top and wiped her sweaty face with it. I felt myself stiffen a little in my shorts. Ellie smiled and said “not basketball this time. Let’s wrestle.” I gasped a little, but tried not to let it show. I couldn’t say no. This was going to be my shot to touch her in ways I’d never get to, otherwise. 

***

After extensive negotiations, the terms were set. We’d wrestle in her extra bedroom, which was equipped with thick mats for her yoga. Pin for a count of three, first to two pins wins. Besides that, we didn’t discuss any real rules. Ellie didn’t put her tank top back on, so she was wrestling in her sports bra and shorts. I still had my basketball shorts and tshirt. We agreed on no shoes to preserve Ellie’s mats.  

Ellie liked her chances, she explained, as she had taken some low-level MMA classes and felt she knew how to grapple. I, on the other hand, knew they have weight classes for a reason and that was going to be heavily in my favor. I may not have studied grappling, but I’m a few inches taller and quite a bit heavier. Some of that weight is some belly fat, but a lot is muscle, too. And all of it is going to help in a game like this. 

On the first round, it played out just like I knew it would. She tried to use her cardio advantage, but the space was too small. I easily got her to the floor and used my size and strength to get the first pin. I sensed how easy it was, and made my plan. I may never get a chance again, I was going to try and enjoy this chance to grapple with my hottest friend. Nothing uncalled for or beyond what was consented to by asking to wrestle, but to the extent the grappling might lead to my hand on her tight ass or her firm tits, I was going to let it happen and make sure I enjoyed it. 

On the other hand, I could see the look in Ellie’s eyes and I had seen it before. She was that uniquely Ellie combination of furious at herself, annoyed with me for daring to outperform her, embarrassed to lose, and determined not to lose again. 

We broke for the second round and this time I played it cagier. She went hard. I kept her at an arm’s length, but she played a lot of offense. I saw my chance to cop a feel after repelling another attack. I spun her around and pushed her away. The goal was to grab her in a bear hug from behind which would let my hand stray up to her tit. Then I’d pull her leg out from her to get her off balance and twist to bring her down for a final pin. 

Part one was a success. I spun her around and bear hugged from behind. My hands started around her waist but one of my hands “slipped” just a little and lingered on her right breast. It was awesome, and exactly what I had hoped for when I agreed to wrestle her after she stripped to just her sports bra. Wasn’t the first or last tit I squeezed that month, but it probably was the best. Part one rocked.  But part two was where everything went wrong. 

In my mind, converting to the leg pull and twist was one smooth move. In actuality, she wasn’t going to go down so easily. Ellie struggled as hard as she could to get her leg free from me. In her ferocious and random thrashing to gain control of her leg, BAM. It happened. 

Ellie inadvertently drove her heel backwards into my balls with all the power her constant treadmill time provided. Immediately, the breath left my body. Before my brain knew about the pain, she had connected a second time, this time with the side of her foot. My stomach cramped and I buckled. Sensing her leg was free, Ellie turned on her heels and saw me vulnerable, with no idea why. She took her chance and tackled me to the ground. I offered very little resistance as she made her 3 count. 

Ellie roared in victory in Round 2 and offered me a hand to get up for Round 3. I swatted her hand away in annoyance and rolled onto my stomach to try curl up and get over the pain. Ellie’s intensity broke into kindness and her eyes reflected real concern as she asked “are you okay? What happened?”

I responded “you fucking kicked me in the balls!”  

Ellie chuckled and said “sorry, man. It was an accident. But I’m pretty sure it still counts as a pin. Take as long as you want.”

After taking a break, we got ready for Round 3. I briefly considered a change in strategy. There was something in Ellie’s eyes. I couldn’t say what, but it gave me pause. Like she suddenly had confidence. Like she figured out the answers in the middle of the exam, just like she always did. Do I need to protect my balls? No, I thought. Ellie wants to win but she wants to win clean. It was clearly an accident, not a strategy. She was genuinely shocked it happened. She wants to win and wants to be able to take pride in it.

That assessment was my other mistake. As I said earlier: some people love to win. But Ellie hates to lose. 

Ellie yelled “go,” and we began Round 3. I went back to my Round 1 strategy. I’m not focused on getting to second base, I’m focused on winning. I rushed in and grabbed Ellie’s right leg, pulling it up and taking her off balance. She offered suspiciously little resistance. I lifted her up slightly and drove her down to the mat, on her back. I grinned, as I saw my final pin coming and my $100 coming into my Venmo. 

But before I can make my move, I saw the most terrifying thing I’ve ever seen. Ellie’s hand thrusted upward, with the speed and precision of a cobra, and made its way up the leg of my shorts. My eyes widen as Ellie’s face twisted into a vicious smile. Her hand immediately grabbed hold of my balls through my boxer briefs and squeezed. 

The squeeze was tight enough to gain total control of me, but not debilitating. Ellie wasn’t going to let this happen fast. As she tightened her grip, Ellie stood up and she pushed me backwards to the wall, refusing to let me fall. With my back against the wall, in one smooth move, Ellie released her grip and (THWACK) landed a brutal and precise knee to the nuts. 

The dull throbbing of her medium squeeze exploded into torture and I saw stars. I wanted to fall to the ground and curl up and die, but Ellie wasn’t letting me. (THWACK, THWACK) Two more swift knees. I started to buckle at the waist and my face fell down towards her stunning cleavage. The cleavage which made me agree to this stupid fight in the first place. Damn that cleavage! Even in all my pain, I still get a little hard being buried in her tits. I heard her chuckle to herself before landing her fourth knee to my balls. 

Her fourth full force knee sent a rush of pain that felt like it grew exponentially and deprived me of any ability I had to support myself. The nausea started to creep in. As impressively fit as Ellie is, she can’t handle me as dead weight. She steered me to the ground on my back. I sighed in relief. She’s set up for her final pin. 

But she didn’t follow me to the ground. She reached down and grabbed my legs. She spread them apart and (THUMP) landed a stomp that manages to find my right nut specifically. Then (THUMP) a second stomp, this one on my left nut. The accuracy and precision was unfathomable. 

The look in her eyes had changed. This isn’t my friend anymore. This is an animal out for blood, avenging every loss I’ve ever dealt her from any competition. This is payback for basketball two hours ago, for Scrabble last week, and for the one class ever I beat her in. She was trying to run up the score against me on some cosmic lifelong scoreboard. Deal me a loss I can’t ever truly recover from, no matter how many times I beat her in beer pong. 

I tried begging her to stop, surrendering and appealing to our close friendship. But just as I was about to beg, Ellie landed another stomp to the balls which took the breath out of my lungs. Then two more stomps in quick succession. (CRACK CRACK). I felt like I was in a nightmare, as the sharp pain just grew deeper and wider. 

With a contemptible smirk on her face, Ellie finally eases up. She let my legs fall to the ground and gave one last snap kick to my balls (WHACK). After the brutality of the stomps kicks, this felt almost playful and merciful to me, lying on my back, powerless. She put her right foot on my chest and softly counted out “1-2-3, pinned” as I laid there, motionless, not wanting to provoke or justify another attack. Those were the first words either of us had said since Round 3 began. 

And then the truly most unexpected part of the evening took place. She stepped forward again, this time with her feet to either side of my head. She reached her thumbs into her waistband pulled down her biker shorts and the black thong that was underneath it. Without saying a word or waiting for any sign of nonverbal consent, she lowered herself onto my face. The look on her face is just as animalistic as during her attack.

In a mix of excitement and fear, I went to work. I presented my flattened tongue and Ellie began riding it. As a fairly skilled and extremely experienced purveyor of pussy eating, I tried to use my considerable talent to make her cum. It was going to be hard, given the unbearable pain I still felt. But just like the rest of this fight, I wasn’t going to be the one who was in control.

As I tried to get my fingers involved Ellie pinned both of my weakened arms above my head with one hand and went to town on herself with her own. She set the pace and basically used my face like a dildo. She rode it hard and fast. 

As she got closer to climax, she started to shit talk. “You thought you could just win without even trying ohhhhhh” she moaned. “But it was so fucking easy to beat you mmmmmmmm” was next. Practically screaming now, “I OWNED YOUR WEAK ASS GAHHHHHH.” After that last one Ellie came hard and long on my face. 

She shifted her knees backwards so she was now straddling my chest, bent forward so her ample cleavage, barely contained by her sports bra, was heaving in my face from her deep breathing. I sat there in suspense, unclear what was next. Her breathing slows, and slowly the animal I had just encountered fades away and her classic wry smile returns to her face. 

She stood up, slips her thong on, and left her shorts on the ground next to me. She walked towards the door, and I couldn’t help but admire that tight ass, even as I laid there in agony. As she reached the door, she turned around, smiling broadly now. She said “you can crash on my couch if you want, but I need you out in the morning, I have to go on a run.” 

She opened the door, stepped through it, turned around, and gave me one more sweet smile. She removed her green sports bra and threw it at me, giving me an amazing view of her perfect tits. She grabbed her tits and said “I know these are why you agreed to wrestle. Since I wiped the floor with your sorry ass, I figured a look is the least I can do for ya.” She walked off to her bedroom.  I waited for an hour before standing up, let myself out, and drove home embarrassed, knowing I’d never be able to explain to anyone what happened to me. I guess I’ll just have to hope nobody asks me why I have a highlighter green sports bra buried in my underwear drawer.