Heads or Tails (Fun with my high school friend)

These characters are from a previous story of mine. You can find the context here:

https://www.reddit.com/r/BallbustingStories/comments/vz6y9t/girl\_power\_part\_5\_riley\_crushes\_a\_pervert/?utm\_source=share&utm\_medium=web2x&context=3

Thanks to u/smasher6446 for suggesting this story!

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‘No way. Riley? Riley Kirk?’


I looked up from my drink. The bar was as crowded as you’d expect for a Friday night, and with a dozen conversations going on around me I couldn’t immediately tell where the voice calling my name had come from. I spun around on my stool and my view was filled by an expanse of dark blue cotton, barely more than a foot from my face. Startled, I fell back onto the bar, involuntarily lashing out with my foot and catching the mystery man in the thigh, just below his belt. He took a step back.


‘Woah, sorry! I didn’t mean to, uh… Hey! Been a while, huh?’


I looked up at the guy’s face and was blindsided by a flood of high school memories. ‘Oh my God! Ethan! How are you doing?’


It was funny how friendly our relationship had become. I thought back to the day I first met Ethan. It had begun with him harassing me in the hallway and ended with his testicles being flattened under my heel. Of course, dominating him hadn’t quite panned out how I’d expected, since he turned out to be into it, but it did have the intended effect of making him far more respectful - I barely recognised the person he became.


As a naive teenager, I hoped this was because I had been brutal enough to beat the fetish out of him, but the longing stares I caught from him in the months following the incident suggested a different outcome: He was smitten. So of course I teased him. Always hinting about how he might earn another kick, but never quite delivering…


Until the night of our graduation. The party was over and I was cooling off outside the hall where the function had been held. I heard the door slide open and turned to see Ethan appear next to me. I gave him a slight smile, which he returned, both silently acknowledging that after this night, we’d be taking separate paths. He broke the silence first.


‘It’s been a good year.’


‘It has, hasn’t it?’ I thought back on my journey of nut-crushing self-discovery. I could firmly say it was life-changing.


‘Shame it’s over, really.’ Leaning against the wall next to me, he slid closer.


I raised an eyebrow. ‘Got something to say?’


Ethan blushed. ‘Well, I was thinking, I might not see you for a long time… Did you want to give me something to remember you by?’ He glanced downward at my legs, which, despite my height, extended far below the hem of my tight silver minidress.


He was being so sweet. I couldn’t resist. Looking into his eyes, I grasped his shoulders and turned him to face me. He gasped, and I saw his face light up in desperate anticipation as I took a step back and - gathering all my strength - kneed him squarely in the crotch. His eyes welled up with joyful tears as I dislodged my knee and he crumpled to the ground.


‘Thank you,’ he managed, hoarsely.


‘See you around.’ I smiled again as I turned and walked away from him for what I assumed would be the last time.


Of course, life rarely turns out that way. After Ethan left for college, we kept in touch for a little while, but in the end the connection fizzled out slowly - It wasn’t the same with the distance between us. After that, I hadn’t spoken to him until the night he appeared in the bar. Suddenly, it was like nothing had ever changed.


‘You haven’t grown,’ he taunted. I afforded him a smirk. It was true. Here I was at twenty-one, still able to pass for a kid in the dim, smoky bar light.


‘And you haven’t grown up,’ I shot back.


He grinned. ‘I know.’


I leaned back more, resting my elbow on the bar. ‘But seriously, what are you doing here? I thought you left this shitty town behind.’


‘Got sick of being successful and popular, I guess?’ Ethan shrugged. ‘Nah, I just had to come make sure nothing’s changed here.’


‘Well, hope you’re happy.’ I gestured at our surroundings. ‘You look like you need a drink.’


‘Yeah, this place does that to you.’ He took a seat beside me and called to the bartender.


We talked for hours about everything that we’d missed. Some time just before last call, the conversation turned to the inevitable. Emboldened by a few drinks, Ethan ventured, ‘So… Remember what you used to do to guys in school? Are you still into that stuff?’


‘And there we go.’ I snapped my fingers, grinning. ‘Ethan wants his balls kicked. I knew there was a reason you came back.’


He flushed red, just like the last time I saw him, and threw up his hands. ‘That’s not the only reason! I swear! But… yeah. I was kind of wondering.’


‘Okay. Yeah, I still do it. A lot. But you know I’m not the only girl to ever have a thing for busting balls, right? Like, half your female classmates would probably jump at the chance to take out their stress on you.’


Ethan suddenly grew serious. ‘Well... yeah. I know. I’ve asked them. And they’ve done it. Riley, I’ve been stomped by so many girls I’ve lost count. And yeah, it hurts. And it feels amazing for a moment. But that’s all. They stop when I want to stop, they never do anything without asking… And all I can think about is that first time. How you beat me until I could barely process the pain. How you made me *believe* my balls were going to pop. Riley… I need to feel that again.’


I was stunned. I knew he was a masochist, but this was another level. ‘Holy shit, dude. Are you sure you remember that night right? You were fucking *begging* me to stop.’


‘But you didn’t. That’s what makes you so perfect. You didn’t give a shit what I wanted. So I’m just saying, I’m okay with you doing whatever you want to me. If you’re interested.’


‘...You’re serious. *Whatever* I want.’ Usually I only dealt out gonad punishment to guys who deserved it. But if he wanted it that badly, who was I to deny him? Plus, it would be nice to not have any resistance for once.


‘Alright, I’m down. But you have to promise not to get mad if I do permanent damage. You should know I’ve taken a *lot* of martial arts lessons.’ That was the truth. I’d always known how to break a man, but over the last few years I’d gone to great lengths to ensure I could do it with barely a thought.


He nodded emphatically. ‘I promise.’


‘And I don’t have to stop? For any reason?’


‘Yeah. No matter what I say.’


‘Alright then. You got somewhere to do it?’


Ethan was caught off guard. ‘Now? Oh, fuck… yeah, my hotel room. We can walk from here, it’s not far.’


I buttoned up my coat and followed him out the door into the cold night. The street was almost deserted as we walked the two blocks to Ethan’s accommodation. Neither of us spoke. I was lost in thought. Ethan was drawn to the idea of not knowing how far I was going to go. That meant I had to decide.


On the one hand, he was a decent guy. He really didn’t deserve to have either of his nuts ruptured. But at the same time, he’d *asked* for this. Surely he wouldn’t want me to go easy on him? It seemed like an impossible choice to make. But then I had an idea. Maybe I didn’t have to.


As soon as we were inside the hotel room, Ethan started stripping away the layers of his clothing, while I leaned against the wall, watching the spectacle. I could tell he’d been working on himself - His once unremarkable abdominal muscles had become rock hard. For a moment I even felt a twinge of attraction - Until he undid his belt. His jeans and underwear fell away to reveal that his package was another thing that hadn’t grown since high school. I had to stifle a giggle.


I pulled off my jacket and threw it on the bed, but kept the rest on. In a powder-blue crop top and matching pleated miniskirt, I didn’t need to undress to look stunning. And of course, I had my favourite round-toed boots. They’d served me well over the years. Seeing Ethan naked in front of me, the feeling of crushing him under these same chunky heels came rushing back. My body tingled with anticipation. I motioned for Ethan to lay down on the bed. When he did so, I climbed on top of him, straddling his body on my knees with his junk behind me.


‘Okay. Here’s how this is going to go.’ I reached for my purse and pulled out two coins, holding them up for him to see. ‘See these? I’m gonna flip them. One for each nut. Heads means that one stays intact. Tails… I get to *really* have fun.’ I smiled maliciously at his terrified expression.


‘But that can wait. I wanna get to know your nuts first.’ I reached around behind myself and felt the soft warmth of his scrotum in my right hand. I squeezed hard.


Ethan cried out and writhed in agony, but I kept him pinned to the bed. I rolled his gonads between my fingers, judging the most painful angles by his reactions. I settled with just my thumb and middle finger on his left nut, a grip that made the boy shudder as I dug my nails in. He desperately grabbed at my arm, but I brushed him off. I made a fist and rapped my knuckles against his manhood a few times, then relented to let him catch his breath.


‘Fuck, Riley, that was intense,’ he breathed.


I ran my fingers gently through his hair. ‘Aw, baby, that was just the beginning.’ I climbed off Ethan’s chest and walked around to the foot of the bed. Grabbing his ankles, I pulled him towards me, brought a knee up to my chest and stomped on his groin. I ground my boot in, crushing his testicles between the hard wooden heel and his pelvis. Still holding his legs apart, I lifted my foot and stomped again, and again, and again, relishing his helpless little whimpers. I watched his sack bruise more with every cruel blow. But his cock stood proud, a paradoxical confirmation that my torture was working as intended.


I pulled on his ankles again, dragging Ethan off the bed and onto the floor in the centre of the room. I dropped his legs and kicked them apart, making a perfect V, drawing my eyes to his bare genitals. It invited me to annihilate them. I took a practice swing to ensure my aim was perfect, then swung my leg back and booted him in the nuts as hard as I could. The force of the impact jolted his whole body.


I stood over Ethan with my hands on my hips, panting. Brutalising his balls was exhilarating, but exhausting. I looked down at the man I was torturing. His eyes were closed and his chest was heaving. He had one hand on his dick, and was semi-consciously pleasuring himself.


‘You know I can’t let you cum yet. We’re not even close to done.’


Ethan stopped masturbating and opened his eyes. ‘Oh… I’m sorry. You’re just so amazing at this, and I…’


‘Shut up.’ I punted his battered scrotum playfully. ‘I’ll let you know when you can start jerking it. Right now, I’m gonna need you standing up.’


‘Oh, God… I’ll try,’ he managed, propping himself up. I took his hand and pulled him to his feet. He almost toppled over as I led him to the edge of the room and pushed him up against the wall, holding him in place with a hand on each shoulder. To play with his mind a little more, I stood on tiptoe and softly kissed him on the cheek. Then I slammed my knee into his tender gonads with a solid *thwack*. Ethan doubled over, burying his face in my bust.


I gasped in mock indignation. ‘I didn’t say you could touch! Naughty boy.’ I pushed him back upright and nailed him with another vicious knee between the legs. His cock, amazingly still solid, slapped against his stomach, and then my thigh, splattering both with pre-ejaculate. He was already close to the edge. It was time to get serious. I lowered my knee and cupped a hand around each testicle, then proceeded to squeeze the life out of them. Ethan’s knees buckled, but I held him up by his nutsack, which stretched to its limit from supporting the weight of his entire body. His wails told me he desperately needed to fall backward to the ground, but I couldn’t let that happen. I increased my grip.


‘Riley, stop, please… It’s too much,’ Ethan spluttered.


I grinned. ‘Nuh-uh. You said to not stop, no matter what. No backsies.’ I closed my fists tighter around his nuts until the flesh started to squish between my fingers. When I was sure applying any more pressure would neuter him, I finally let go and he crashed to the floor. I lifted my boot and held it in the air over his crotch.


‘Riley… Please don’t…’


‘I remember you saying I could do whatever I want.’


‘I didn’t mean that. *Please*.’


‘Then maybe next time don’t give a girl *carte blanche* to fuck up your genitals, huh? If there is a next time, that is. Don’t forget about the coin toss, cutie.’ I stomped. He screamed. I twisted my heel and used it to pin his fragile orbs to the floor. Pressing down harder, I watched the clear fluid flow from his penis as freely as it did from his tear ducts.


‘Wow, somebody’s having fun! You can start jacking off now. It’s time.’ Ethan obediently began to pump as I released him from underfoot and picked up the two coins off the bed. I flicked the first coin into the air and caught it cleanly in my fist. ‘This is for the right one. Heads you keep it, tails I pop it, remember?’ I opened my hand, made note of the result and slipped it back into my purse.


‘Uh, do I get to see it?’ Ethan asked timidly.


‘Nope. Where’s the fun in knowing whether you’ll still have balls tomorrow?’ I giggled. I picked up the other coin. ‘This one’s for the left.’ Ethan’s eyes tracked the coin as it fell, but I clamped my hand around it. I took a quick peek and put it away. With that, Ethan’s fate was sealed. I unlaced my boots and pulled them off - I wanted to feel every bit of this. Then I stepped between his legs, straightened my skirt and brushed my locks of light brown hair out of my view.


The beaten, shivering boy on the floor tried to plead one last time. ‘Riley, please. This has been incredible. Thank you so much. But… please stop. I can’t take any more.’


I smiled apologetically. ‘Sorry. But trust me, you’re gonna thank me for this one day.’ I took a step back, then sprang forward and slammed the instep of my bare foot into his swollen sack. All blotchy and twice its original size, it looked ready to burst. I delivered another kick that made Ethan convulse. Disappointingly, he’d abandoned his self-stimulation, instead trying pointlessly to defend his crotch. I sighed, bent down and pried his hands away.


If he wasn’t even going to *try* to cum, I’d have to take matters into my own hands. I knelt between his thighs, wrapping my left hand around his shaft and cradling his left ball in my right. I began to massage his glans, gently at first, but with increasing vigor. As Ethan began to moan with pleasure, I suddenly clamped my other hand around his gonad and squeezed it with all my might.


Ethan bucked uncontrollably as I edged him towards violent euphoria. He wailed as I emasculated him, gasping for air with every stroke. As I rubbed him, I squeezed his nut tighter and tighter, barely able to contain my own excitement as the tissue began to break down.


Finally, just as he started to lose consciousness from the extreme conflict of ecstasy and agony, Ethan reached the most intense climax he would ever experience. In a superhuman effort that lasted fifteen seconds, he covered his chest in ropes of jism - Just as his left testicle popped in my hand. He blacked out. I kept kneading his nut-meat until there was nothing left of it.


I couldn’t tell you how long it took for him to come to - I was in Heaven. No matter how many times I did it, rupturing a testicle was the ultimate high.


Eventually, Ethan’s eyes opened to find me sitting on the edge of the bed, swinging my legs absently. The look he gave me was distraught. He tenderly felt his scrotum, realising the gravity of what had just happened. ‘Riley… it… It’s gone. You fucking destroyed it.’


I shrugged. ‘You knew the risk. Was it worth it?’


He hesitated. ‘I… I don’t… Riley, you’re a fucking amazing ballbuster. But you just *half-castrated* me… because the coin toss said so? *What the fuck?*’


I grabbed my coat off the bed and pulled my boots back on, then stood and made my way to the door. I glanced back at the broken boy, admiring my handiwork one last time. I smirked. ‘Oh, yeah. I should tell you… Both the coins came up heads.’


That was the last time I ever saw Ethan.