The summer heat clung like molasses to the sleazy dive bar’s walls when Dinah-Moe strutted in, hips swaying with predatory grace. Her dress – blood red and tight as sin – barely contained curves that could make a priest question his faith. Dark hair tumbled past bare shoulders slick with a sheen of sweat, and those hungry emerald eyes sized me up like a lioness eyeing her prey.
“Well, well… what do we have here?” she purred, ruby lips curling into a dangerous smile as she slid onto the barstool beside me. The scent of her expensive perfume mixed with natural arousal made my head swim. She produced a crisp forty-dollar bill, running it teasingly across her cleavage before waving it under my nose.
“Got a proposition for you, stud. See, I’ve got this theory about men – you’re all worthless when it comes to pleasing a woman. My sweet little sister Flora disagrees…” She gestured to a blonde bombshell in the corner booth, watching us intently, unconsciously licking her lips. “So we made a bet. Forty bucks say you can’t make me cum. Not one single orgasm. Whatcha say, big boy? Up for proving me wrong?”
I took my time answering, savoring the way her nipples hardened beneath the thin fabric as I let my gaze roam over her body. “Challenge accepted, darlin’. But let’s make it interesting – if I win, I get more than just the money.”
Three hours later, my bedroom was a symphony of gasps, moans, and the wet sounds of flesh on flesh. Dinah-Moe writhed on my silk sheets, her wrists bound with her own torn pantyhose as I tortured her with pleasure. My thumb worked circles on her throbbing clit while three fingers pumped steadily into her dripping pussy, curling to hit that special spot that made her whole body shake.
“Unnnngh… fuck… not gonna… happen…” she panted, even as her hips betrayed her by grinding desperately against my hand. Her juices coated my fingers and palm, trickling down to soak the sheets beneath us.
Flora had long since stripped naked, unable to resist joining us. She knelt beside her sister’s head, playing with her breasts as she watched me work. “God, sis… just let go… cum for him…” she moaned.
I increased the pressure and speed of my fingers, feeling Dinah-Moe’s inner walls flutter. “That’s it, baby… fight it all you want, but your body knows what it needs…”
“No… no… oh fuck… OH FUCK!” Dinah-Moe’s back arched off the bed as the dam finally broke. Her pussy clamped down on my fingers like a vice as she came, gushing all over my hand and the mattress. Her whole body convulsed with the force of her orgasm, unintelligible sounds of ecstasy ripping from her throat.
Flora’s hands flew to her soaked pussy, frantically rubbing as she watched her sister come undone. “My turn… please… need it so bad…”
I kept Dinah-Moe’s orgasm going with my fingers while positioning myself behind Flora. “Beg for it, baby…”
“Please fuck me! Need your cock… need to cum like she did…”
I slammed into Flora’s tight heat in one thrust, making her scream. The sight of my cock disappearing into her pussy while her sister continued to writhe and moan pushed Dinah-Moe into another intense orgasm.
Hours passed in a blur of sweat, cum, and pleasure. By dawn, both sisters lay completely spent, their bodies covered in love bites and sticky with various fluids. Dinah-Moe’s mascara had run down her cheeks from happy tears, her voice hoarse from screaming.
“Keep the money,” she rasped, trailing her fingers through the mess on her thighs. “Just promise we can do this again…”
Flora nodded eagerly in agreement, still trembling from her last orgasm. “Next time…” she purred, “I want to watch you fuck her ass while I sit on her face…”
That forty dollars stayed tucked in Dinah-Moe’s purse, forgotten. But it sparked a regular arrangement – every Friday night, the sisters would show up at my door, ready for hours of intense pleasure. And Dinah-Moe never made another bet about not being able to cum – she was too busy having multiple orgasms to even think about it.
