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The Rebirth of a Playboy

"Once a Playboy always a Playboy"

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Author's Notes

"2 more entries after # 6"

Tyrell lies on the milking table, his body glistening with sweat as Lena gently wipes him down with a soft cloth. The room is filled with the scent of lavender and jasmine, a calming yet intoxicating aroma that lingers in the air. Debra and Frances stand nearby, their eyes locked on Tyrell, waiting for his next move.

"Alright, big boy," Lena purrs, leaning in close to his ear. "What do you want to do now? We can keep going, or we can take a little break."

Tyrell's mind races with thoughts of pleasure and anticipation. He knows they have more in store for him, but he’s curious about what else they might have planned. His cock, still semi-hard from the intense orgasm moments ago, twitches at the thought of more action.

"I think I need a little more," Tyrell murmurs, his voice hoarse from the intensity of the previous activities. "But let’s change things up a bit."

Lena’s eyes sparkle with mischief as she nods. "Of course, Tyrell. Whatever you want." She turns to Debra and Frances, exchanging knowing glances before nodding in agreement.

Debra steps forward, her hands gliding over Tyrell’s chest, tweaking his nipples playfully. "How about we give you a little taste of what it feels like to be on the receiving end for a change?"

Frances smirks, retrieving a small bottle of oil from a nearby table. "Let’s get you ready, then."

Tyrell watches as Frances uncaps the bottle and pours a generous amount of oil into her hands. The warm liquid glistens under the dim light, its viscosity almost hypnotic. She rubs her hands together, heating the oil, before slowly massaging it onto Tyrell’s ass cheeks.

The sensation is immediate and intense. The oil penetrates his skin, warming his muscles and making them pliant. Tyrell groans, his hips instinctively lifting off the table as Frances’ fingers press deeper into his flesh.

"Relax," Frances whispers, her voice a sultry murmur. "Just enjoy the feeling."

Tyrell does his best to comply, but the sensations are overwhelming. His breath comes in shallow gasps as Frances continues her ministrations, her fingers dancing across his ass, teasing and probing.

Lena steps in, her hands replacing Frances’ as she takes over the massage. Her touch is gentler, more soothing, but no less effective. She kneads the oil into Tyrell’s skin, paying special attention to the sensitive area around his hole.

"Almost there," Lena coos, her lips brushing against his ear. "Just a little more."

Tyrell feels a finger press against his entrance, slick and insistent. He tenses for a moment, but Lena’s reassuring words calm him. Slowly, agonizingly slowly, the finger slips inside, probing deeply.

"Good boy," Debra says, her voice dripping with approval. "Now just relax and take it."

Tyrell does as he’s told, his body trembling with the effort of staying relaxed. Lena’s finger explores him thoroughly, finding all the right spots and pressing gently. The sensation is excruciatingly pleasurable, driving him to the edge of sanity.

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Frances reappears, holding a small, vibrating toy in her hand. "Time to add a little extra stimulation," she says, her tone playful.

Tyrell watches in fascination as Frances positions the toy against his prostate, the vibration humming through his body. The dual sensations of Lena’s finger and the vibrator create a symphony of pleasure that threatens to overwhelm him.

"Fuck," Tyrell mutters, his voice strained. "This is... too much."

"Shh," Lena soothes, her finger still working tirelessly. "Just let it happen."

Tyrell’s world narrows to the sensations coursing through his body. The vibrator pulses rhythmically against his prostate, sending waves of ecstasy rippling through him. Lena’s finger explores every inch of his inner walls, seeking out new areas to stimulate.

Debra watches intently, her eyes gleaming with excitement. "You look so good like this, Tyrell. So open, so willing."

Frances chuckles, her hand moving to cup Tyrell’s balls, rolling them gently in her palm. "He’s practically begging for more."

Tyrell’s mind is a fog of pleasure, his senses overloaded. The scent of the oils, the sound of the vibrator, the feel of Lena’s fingers—it’s all too much to process. He’s teetering on the edge of control, his body primed for another orgasm.

"Please," Tyrell gasps, his voice barely audible. "I need..."

"What do you need, baby?" Lena asks, her voice a velvet caress.

"More," Tyrell manages to say, his eyes fluttering closed. "I need more."

"Then take it," Frances commands, her voice firm. "Take everything we give you."

With that encouragement, Tyrell surrenders completely. He opens himself up to the sensations, allowing the pleasure to wash over him. Lena’s finger moves faster, more determined, while the vibrator continues its relentless pulsing.

Debra leans in closer, her mouth hovering just inches from Tyrell’s cock. "Ready for round two, stud?"

Tyrell nods weakly, his body trembling with anticipation. Debra grins, her lips parting to reveal a set of perfectly white teeth. She wraps her lips around the head of Tyrell’s cock, sucking gently as she begins to stroke him with her hand.

The combination of sensations is too much for Tyrell to handle. He’s drowning in pleasure, every nerve ending alight with the intensity of it all. Lena’s finger, the vibrator, Debra’s mouth—it’s all coming together in a perfect storm of ecstasy.

"Cum for us, Tyrell," Lena whispers, her voice barely audible above the hum of the vibrator. "Show us how much you love it."

Tyrell can’t hold back any longer. With a guttural groan, he spills over, his cum erupting from his cock in thick, hot spurts. Debra swallows it all, her mouth working tirelessly to catch every drop.

As the orgasm fades, Tyrell collapses back onto the table, his body limp and exhausted. Lena removes her finger, giving him a tender kiss on the cheek.

"Well done, baby," she murmurs. "You took it like a champ."

Published 
Written by CAPPDADDY
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