Frank is ecstatic as Stella agrees to go on a Valentine's date with him. He has been crushing on her for months and finally works up the courage to ask her out. Little does he know, Stella has ulterior motives for agreeing to the date. Stella can't help but notice Frank's baggy pants and whitey tighties. She can't imagine dating someone who can't even dress properly. She decides to take matters into her own hands and teach Frank a lesson. She grabs him by his waistband and pulls his baggy pants down, revealing his embarrassing underwear. Without a second thought, she yanks them up as high as they can go, giving Frank the ultimate wedgie. He lets out a scream of pain as the fabric digs into his skin. Relentless, Stella uses all her arm strength to pull the underwear higher and higher until Frank's ass is practically being ripped apart as the fabric stretches to its limit. Giving him the wedgy of his life, she can't help but enjoy the sight of him squirming and screaming in agony. She even hangs his underwear over his shoulders like a purse, making him look like a complete fool. But she isn't satisfied yet. She pulls the fabric from the middle of his underwear, picking him up off the ground and stretching his underwear even further. Frank's balls are already sore and blue from the intense squishing. But she doesn't stop until she hears the fabric slowly rip apart from his asshole being torn from being pulled so high up. She gives him a wedgie until his underwear is stretched and ripped to its absolute limit, hanging over his tiny head. Satisfied with her work, Stella lets go of Frank, who collapses to the ground in pain. She can't help but laugh at the sight of him, his underwear stretched to its breaking point and his face red with humiliation. And as Frank tries to gather himself, Stella can't resist giving him one final wedgy, just to make sure he never forgets the lesson she taught him. Frank better make sure to always wear proper fitting underwear, never wanting to experience the intense wedgy of his life again.