Yes

“Good, let me get you in position” she says with a chilling smile. She tugs on your balls, stretching them out so they’re pushing against the lips of her pussy, she then positions your cock with her other hand so that it tip is grinding into the top of your balls. “Wow this might actually work, always thought I’d need a man with a massive sack to do this, but turns out he just needs a small dick” laughing down at your contorted manhood.

Without warning she thrusts herself down onto your balls, the pain wracks your body as her cunt grinds cruelly against the trapped orbs, unable to escape as your dick bends precariously against them. With a soft “schlupt” your entire package is forced into her dripping folds, far more moist than during your attempts to get her off before.

She bounces up and down a couple of times, her breasts bouncing heavily above your head, you have no time to enjoy the sight though as it feel like you manhood could give at any moment. Your dick is forced into uncomfortable angles as it stabs into you balls, crushing them against her tightening walls, but not allowing either to slip free.

She continues to bounces on you manhood, causing alternating feeling of pain as her weight compresses you package onto itself, before stretching it out as she raises up. You think at least there’s room enough to let them slide around but as time passes you feel more and more resistance as your genitals are crushed within her pussy. It’s as if your whole package is being crushed in a vice and you wonder how come she never felt this right before.

After further bouncing and grinding from the woman pain rockets from your cock, and you hear the a sound like celery breaking. “Ah shit, I’m so close!” She says breathlessly, apparently unaware to the trauma she inflicting down below. Your cock feels like it’s swelling at a strange angle, causing it to add further pressure to your already compressed testicles.

All at once you feel her pussy tremble the contract tighter than ever before, your balls are left with nowhere to go, and you hear two muffled “pop-pop” from within her. Pain causes you to cry in pain as she moans in ecstasy, her fuck tunnel spasming hard as it seem to grip tightly around package and wring out everything from it, the small relief of cumming is lost to you amongst the pain as it feel like your nuts are ground flat and your dick is contorted beyond repair.

After a minute to regain her composure she finally looks down at you and lifts herself off. Your cock slips out like a soft tube of meat, heavily bruised and swollen with a clear kink near the top that wasn’t there before. She lifts further, your sack still stretching from her pussy, before it falls to the floor with a grisly “splat”, no longer containing its usual orbs, it lies on the floor like a deflated ballon, it’s contents sloshing about slightly as you twitch in pain.

Admiring her handy work she gives your genitals some inquisitive pokes, before winking and saying “well I hope it was good for you too”, you pass out to her smiling face.