Measuring Up To His Expectations
2026·37 min·100% liked
Jill shows up at Trent’s place carrying his custom suit like a lunch tray. He’s rich, he’s twenty-something, and he’s already used to getting whatever he wants. She helps him into the jacket, smooths the shoulders, crouches to tug the hem straight. Nothing unusual. Except Trent’s already convinced she wants him.
While she slides the tape across his chest, he reaches down and grabs a handful of tit through the fabric. Jill freezes, tape dangling. She tells him to cool it—she’s just working. He doesn’t like the word “just.” His grip tightens.
She could slap him, storm out, lose the client, lose her paycheck. Instead she keeps the tape moving, acting like his hand belongs there. He grins, thinking he’s won, and she drops to her knees to pin the inseam. The new pants stretch tight across him; she can feel how worked up he is through the wool. Her fingers brush his balls while she checks the length, all business except it isn’t. Trent laughs, low, and slides two fingers past her collar, finding the tattoo that curls along her collarbone. He traces it like a signature he just put there.
She stands, skirt riding high, and lets him back her against the mirror. Her blouse opens one button at a time—his doing—until heavy tits spill out, nipples already tight. He palms both, squeezes, rolls them between finger and thumb. Jill bites her lip, stares at the ceiling. Career on the line. He pushes the jacket off his shoulders, drops his new slacks, cock thick and flushed. She wraps her hand around it without being asked, stroking once, twice, testing weight. He groans, steps in, hikes her skirt and shoves two fingers straight into her pussy. She’s wet. Of course she is. Her hips jerk forward; a soft, filthy sound leaves her throat. He curls those fingers, knuckles brushing her clit on every thrust, and her knees buckle against the glass.
She’s still holding the tape measure like a prop. He yanks it from her fingers, loops it around her wrist, cinches it. “Hold still,” he mutters, pumping harder. Jill’s eyes flutter. Blonde hair sticks to her cheek. She spreads her legs wider, lets him finger-fuck her until her thighs shake and the mirror fogs with her breath. When he finally pulls his fingers free they’re shiny; he wipes them across her tits, leaving streaks on pale skin and ink. She looks down, catches her reflection—suit jacket hanging open, skirt bunched at her waist, mouth open like she’s already moaning his name.
Trent steps back, hard cock bobbing, and tells her to finish the fitting. Jill wipes her mouth with the back of her hand, drops to her knees again, and takes his length between her lips like it’s just another alteration. The tape measure dangles from her wrist, numbers swinging with every bob of her head, proof that business is getting done.
Directors:Seth Gamble













