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Measuring Up To His Expectations

2026·37 min·100% liked
Jill shows up at Trent’s place with the finished suit tucked under her arm. He’s young, loaded, and used to getting his way. She plays it cool like any good tailor would while he strips down and steps into the jacket. The fit’s sharp, but she still needs those last measurements. Tape in hand, she starts at his shoulders, then drops to his chest. He leans in, grinning, thinking she’s looking for more than inches. Jill steps back, voice steady. "I’m just doing my job, sweetheart." That line lands wrong. His smile drops. Suddenly the room feels smaller. She can walk out and kiss her reputation goodbye, or she can keep him happy and keep her bookings. She chooses her paycheck. The tape slides lower. Her blouse comes undone. Those big tits spill into his hands while his fingers push past her waistband and sink knuckle-deep inside her. She’s blonde, inked, and twice his age, yet right now she’s the one getting measured.

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