As soon as he was able to gather his thoughts once again, he met the gaze of his girlfriend, once again clenching him at his sides, her legs still as strong as they were before he was inside of her.
“Who said you could cum?” Jillian commented, raising an eyebrow, trying to figure out where her directions had gone awry.
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“I… I didn’t mean to-”
“Sure you did. You came before I did.”
“But-”
“No buts. You were supposed to cum when I told you to cum.”
“Hey, listen, I don’t have absolute control over that-”
“Sure you do. All you had to do was let me take care of it.”
Seemingly getting nowhere with the conversation, Jillian began to squeeze a bit harder with her legs, knowing full well that his nutsack was nowhere else but between his legs, something that her squeezing would not take well to. Immediately he tried his best to hide the present sense of pain slowly coming up with his testicles having nowhere to go but quickly met his match at the fact that his member was still inside of her, missing the pleasure that it needed in order to stay hard, getting covered in a mixture of her own juices and his jizz as it slowly returned to a more flaccid form. Even with this, he was absolutely trapped underneath her, her gym work and developed strength of her toned body proving to be something to go up against.
“Alright! I’m sorry! Is that what you wanted to hear?” William nearly shouted, the pain starting to spike as far up as his underside, the few but strong sparks being enough to prove that it was either being pinched or squoze in such a way that was far less than beneficial for any of his future children.
“Not good enough.” Jillian commented, leaning forward once more as she laid on top of him, her grip not wavering one bit from the ironclad grip she had around his bunched legs, the direction of his dick changed as she leaned forward, wasting no time to make an effort to get her point across. “You think I can’t get other people to cum when I call on them to do so? What do you think this is?”
“Jillian, I didn’t mean to.” Will admitted once more, trying his best to make her understand his little bit of self greed for his own satisfaction. “Look, I was just… really turned on by you, and I couldn’t hold it in like you wanted me to. I’m sorry.”
“Sorry isn’t good enough.” She repeated, making her point clear as she squoze with as much force as she could muster, remembering the few attempts she had made in the kitchen during the summer prior, crushing watermelons between her thighs was of no issue. Now, it had become nothing more than the balls between his legs, an immediate few yelps coming from him as his hands shot out, only to realize that he was, in nearly every way, shape and form, unable to stop his girlfriend from the crushing that was occurring. “I think it’s time for your punishment for being a naughty boy.”
“Punishment?!” William belted out, only for one final squeeze to come up from her legs, forcing his member’s family jewels to be crushed within the force of his own legs, unable to be pried open with whatever force he could muster to push out as her thighs completely overpowered everything he could do to stop her from squeezing him so tightly, an immense amount of pain already amounting from the force she was exerting. It was unlike any other he had felt before, not having a particular point at which it felt it was being damaged, but rather across his entire sack and especially the testes within being incredibly susceptible to such squeezing. A yelp escaped his lips as she began to relax, only to go back and squeeze in one final time before allowing him a small rest, his now semi-hard member keeping up the slack at the fact that this pain was something different.
“Is this… turning you on…?” Jillian muttered, baffled as she stood up, some of his juice trailing down her leg. She planted a foot on his chest to keep him attached to that portion of the bed, still laying flat on his back and naked, only to reach over to the nightstand and grab a tissue to clean up the fluid that was ‘accidentally’ left inside of her. She came to the terms quickly that her Bill was ultimately, knowing how her demeanor was, probably into the whole thing, knowing full well that his girlfriend was getting off on the fact that such a weak and feeble dick was both at her beck and call and his pain meant her pleasure.
William dared not reply, knowing full well that his half chub was not something that he could hide, especially not now, and it especially was not from the single moment that had occurred where he fell out from inside of her. He looked up, Jillian now standing above him on the bed, simply looking down on him with a look he could only describe as disdain. He was completely under her control, even for whatever punishment she wanted to inflict onto him for his accident.
“Tsk. I knew it.” She muttered to herself, pushing his legs open with her other heel, the full weight of her body down against the center of his ribcage for just a moment, nearly knocking a full exhale out of him at the sudden shift of weight. Her other foot allowed her to regain her balance as it pressed directly against his member, her toes fully pressing down on the base of her shaft and the ball of her foot pressing his testicles to the very edge of his sack, the true pain only beginning just as she rocked her foot back and forth ever so slightly. William became immediately aware of the immense, writhing pain coming up from beneath him, shooting well beyond his member and into his surrounding thighs, the burning sensation all but becoming clear as all of his body screamed out for her to stop what she was doing.
Despite that, however, something a bit deeper lurked under the surface. Something… far more nuanced than what he was able to explain. Somewhere, deeply inside him, slowly but surely progressing to become a more and more corrupted psyche at the behest of his girlfriend was something that he had only fallen into as a result of having to deal with such practices, but this was far more than what he was regularly expecting as per the regular course of action. Only a few mere moments passed under this level of pain, and yet… Here he was, fully erect, once again having his member raring to go beneath him, nearly at the intensity that it had been across the entire past week without a single release, neither from him nor his girlfriend. Jillian looked down to discover this, releasing her foot from his balls, slightly taken aback that he was getting far more gratification and enjoyment out of this than she expected he would. Rather than have it be some kind of very light and guilty pleasure, it had proven itself to be nothing short of difficult to deal with, his member fully erect, his body ready to accept anything that came its way once more.
“What kind of… masochist are you?” She questioned, trying her best to understand exactly what it was that turned him on. Had it been her foot on his nutsack? There was no way, there was absolutely no way he was into feet… it simply had to be the pain he felt on and across his dick.
“Not a masochist, I have, quite literally, no idea why this is happening.” He quickly replied, gesturing vaguely to his member, slightly embarrassed at the fact that a sensation that he detested had also gone as far as to turn him on.
“I think I know why.” Jillian responded, taking her time to enjoy what she was seeing as she stepped to the side, being careful to watch her footing as she took her foot off of his balls, once again forcing a puff of air out from his lungs as she fully stepped off of him, allowing him a moment of freedom from her dominant, oppressive action, only to be met with her once again sitting near the edges of his legs, her sizable behind resting firmly on his shins as she adjusted her sitting position, still partially locking him in place.
Looking to investigate her claim a bit further, she waited, simply almost holding him down to make sure that it was not something that happened as some kind of a fluke. Slowly she watched as his member slowly deflated from the lack of any kind of action, rather slowly as William’s eyes traced her form, met with only a disapproving look from her part from his actions taken before, knowing full well that this ballbusting was a mechanism of his own making, a punishment for his wrongdoing.
Just as it managed to fully deflate, she waited just a moment before issuing it an incredibly hard slap, her fingers fully slapping against the side of his member hard enough for it to flop over to the other side, the sensation of which immediately sent William into a spiral of panic, pain, and uneven breathing. He could barely breathe at the fact that he was hit in such a way, only to be further confused at the fact that his member, once nearly completely softened, had stiffened up once more, an erection slowly growing at the sensation of a single slap. He bit his lip, trying his best to hunker down as she drew her arm back once more, issuing yet another incredibly forceful slap to his shaft, barely able to keep it together as the sensation of tears started to well up in his eyes. The worst part was that he was into it, and no matter how much it hurt… it was as if he did not want her to stop from slapping his member around. To both his dismay and his euphoria, Jillian drew her arm back once more, this time at a different angle, one that was sure to slap downwards onto his stones, the impact providing nothing more than a-
“GAAAH!” He coughed, the second any contact was made proving to be more than enough to send nearly his entire body spiraling into a panic, a visceral reaction occurring at the mere slapping of something so sensitive repeatedly, only for the other half to get slapped incredibly harshly with nowhere to move to, nowhere to redistribute the force that had been issued by moving. Jillian giggled in reply as he shot up, his hands immediately moving to cover his crotch, biting at the inside of his lip and trying his best to fight off the tears that he felt coming on, the sheer amount of pain more than enough to send him over the edge for what a grown man would be able to handle, his muscle mommy slapping down on him proved to be too much for anyone to handle, much less his untrained pleasure stick.
“Oh, but you like it though.” She commented, something that he did not want to admit in reply, but it was far too easy to tell that it was the truth simply by looking at his crotch. He took a moment to simply breathe, assuming his hands would be more than enough to protect himself from her wrath, or her sadistic tendencies, whichever it happened to be. Regardless of whatever it was, however, his protection of himself proved to be easily thwarted by his companion, just as she dug a knee forward, more than enough force slapping his hands down into the base of his fully erect member and the top of his scrotum, once again letting out another yell of half pain, half pleasure, fully enjoying and equally hating what she was doing to him. Had this become one of his guilty pleasures all along…?
“I think I’ve got one more for you, then we’ll be able to call it even.” She cooed, the very last thing William wanted to here for the moment, just as he tried to free his legs from being under her control, only for her to clamp down with her thighs again, seemingly never getting tired, locking him in place just as she had before. “Lift your hands.”
“You’re going to make me cry.” He commented, no matter how turned on he was by the acts, there was still a degree of pain that he had to deal with, and… just for this next few moments, he wanted a simple break from what was occurring, despite now being completely open to the idea of having to get anything he wanted from her end, whether it be slapping, groping, stomping…
“I won’t, I promise.” She cooed, trying to get him to open his defenses for just a moment so she could inflict the final portion of whatever punishment she had thought up within the last few moments. “All I want to do is… make sure you know what the deal is between us. I’ll discuss that as soon as you finish up with your punishment, okay?”
“...Fuck. Alright. Just, like, just don’t kill me.” William emphasized, trying his best to not freak out the moment he removed his hands from being the protective barrier to his balls, waiting for just a moment as her hands slowly rubbed up his thighs, gently resting and gripping around the shaft of his dick, seemingly investigating what damage she had already done. She used one hand to lift up his penis closer to his body, and before William could even act to try to stop her, despite how much he wanted her to do something, anything to him, her thumb and pointer finger created a small ring around the base of his member, wrapping around the top of his ballsack without issue, only to become quickly tight, stopping William in his tracks as he sat up, immediately feeling the tension she was providing in such a small quantity with such a strong force.
“If you move too much, you’re going to make it way more hurtful for yourself.” Jillian warned, slowly starting to draw her fingers back, pulling the loose skin to be more taut, further and further as the skin became thin and smooth, fully aware that she had intended on pulling on his balls. At the pulling of his member, his dick moved forward once again, pointing directly at Jillian’s face.
“Shit! Aaahg… S-F… Fuck!” William could barely choke the words out as he tried to withstand the pain that came, every millimeter of space taken was not one he had to give, each and every nerve ending within his balls screaming out for the moment to stop, for his brain to do something to stop this deranged woman, anything at all to protect the future family and his livelihood that just so happened to remain produced between the two organs and the pouch of flesh that she was oh-so-ungratefully tugging on. And yet, his brain reacted in turn in a far different method, forcing his heartbeat to quicken, his breathing becoming lighter and lighter, the feeling of an intensely strong sensation and shiver cross his entire body just as he shot a load directly into Jillian’s face, an incredibly strong and voluminous spray of white and clear jizz finding itself adorned across the sides and top of her hair, completely slathering her nose and nearly going up one nostril, her eyes clamping shut as the projectile made contact. Her hands released as she immediately shot back, incredibly surprised and laughing at the fact that even though she had only touched his dick for a moment to move it out of her way to pull on his balls, it was hot enough for him to cum unprompted whatsoever, the pain not even covering the extent of the pleasure he had to feel in the moments that it all occurred.
“You actually just did that…” She commented, using a spare hand to wipe away what fluid she could from his expulsion from her face, her hand nearly fully covered while still feeling the slightly sticky, oozing texture across her face, William in return carefully closing his legs together, his hands covering his member to prevent any further punishment.
“That was all your fault that time.” He accused immediately, laughing as well at the sheer absurdity of the situation in question. He had not even considered cumming on her in that moment, and yet, that orgasm was likely the strongest he ever felt, sheerly at the behest of the remainder of the pain he felt across his lower half as he was subjected to such a pain. Such a welcome pain that happened to only bring him closer to a climax, but a pain nonetheless.
Jillian spent a bit of time cleaning herself and her boyfriend up, her attitude changing entirely now that his punishment had finished back to the normal girl the pair had grown accustomed to. She relaxed once more, not needing to put up her dominant side all the time, despite the knowledge that they both shared, knowing full well that she was not giving up her dominant tendencies at all in the process.
“...Hey.” Jillian replied, just as she was about to get into bed, William already underneath the covers, scrolling blankly on his phone for a moment, his mind not fully quite wrapping around what had happened in the few hours prior. He was completely uncertain at how to feel of this discovery, but… such exploration gave him a sensation he had never felt with anyone before, ever- there had to be more to be found, right?
“Yeah, Jill?” He replied after a moment, banishing the thought.
“I’ve got this other plan that might turn you on, if you’re interested to hear.” She cooed, walking a pair of fingers up his now clothed chest, jokingly enough as she pulled all the blankets ot her side, something William immediately detested. She stuck her tongue out in reply, rolling for just a few moments so that she was the only one with any of the blankets, being sure to take his attention if he wanted any hope of staying warm on the cold winter night.
“...Fine, I’ll bite. What is it?” He questioned after a moment, being let back into the blanket bundle once Jillian released it from her grasp.
“So, there’s this investor meeting at work tomorrow, and Cyrus is going to be there…”