Sailing Instructor's Casino Suite Strap-On Jackpot
Cocky sailing instructor gets strap-on fucked senseless by a rich divorcee in her casino suite.
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The sun hung low over the turquoise lagoon like a ripe mango, casting golden light across the wooden dock where Riley leaned against a coiled rope, her salt-stiffened tank top clinging to the lean muscles of her back. At twenty-eight, the sailing instructor had the kind of sun-kissed confidence that made guests forget they were paying for lessons and start paying attention to the way her mischievous grin flashed white against tanned skin. Her dark hair was pulled into a messy ponytail that somehow looked deliberately windswept, and her board shorts rode low enough on her narrow hips to draw the eye.
Vanessa stepped off the small catamaran with the grace of someone who had never needed to worry about balance in her life. Thirty-two, freshly divorced, and radiating the kind of money that came from a settlement large enough to buy a small country, she wore a white linen cover-up that fluttered open to reveal a black bikini underneath. Her auburn hair spilled over one shoulder, and her hazel eyes held the amused detachment of a woman who had already won most games she’d ever played.
“You weren’t half bad out there, rich girl,” Riley called, pushing off the post with a lazy roll of her shoulders. “For someone who kept calling the jib the ‘flappy thing.’”
Vanessa’s laugh was low and expensive, like velvet dragged across marble. “And you weren’t half bad at staring at my ass every time I bent over to tie a knot, sailor.”
Riley’s grin widened, sharp as a reef cut. “Guilty. Though in my defense, you bend over with conviction. It’s inspiring.”
The flirting had been building all afternoon, each teasing remark growing bolder as the wind filled the sails and the two women found themselves alone on the water. By the time they docked, the air between them crackled with possibility. Vanessa tipped her generously, sliding a folded bill into the pocket of Riley’s shorts with deliberate slowness, fingers brushing warm skin.
“Keep that energy tonight,” Vanessa murmured, close enough that Riley caught the scent of coconut sunscreen and something richer, more dangerous. “I’m feeling lucky at the tables. If the cards love me the way the wind loved you today, I might need someone to help me celebrate.”
Riley’s pulse kicked hard. “You know where to find me. I give excellent… congratulations.”
Vanessa’s smile promised trouble. “I’m counting on it.”
Three hours later, the casino floor pulsed with sound and light. Vanessa sat at the high-stakes blackjack table in a backless emerald dress that made her look like money personified. Chips stacked in neat towers in front of her. When the dealer pushed another winning hand across the felt, the suite’s private hostess discreetly informed her the total had crossed six figures. Vanessa’s laugh rang out, bright and victorious.
She found Riley exactly where she’d left her—propped at the bar in a fresh white button-down with the sleeves rolled up, nursing a club soda and looking like sin wrapped in sailor chic.
“Jackpot,” Vanessa announced, sliding onto the stool beside her. She set a heavy casino chip on the bar between them like a gauntlet. “Literally. I just ruined the house.”
Riley’s eyebrows climbed. “Holy shit. You really are lucky.”
“I am.” Vanessa’s gaze traveled slowly down Riley’s body and back up, openly appreciative. “And I’m in the mood to share my luck. My suite. Top floor. Private elevator. You coming?”