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The Lucky Winner


As the clock struck midnight, the dimly lit room at a downtown Minneapolis night club was filled with a swarm of people in their best attire. Among them stood Diane, her golden blonde locks cascading down her bare shoulders in loose waves. Hey black dress was perfectly fitted to her impressively fit figure. Her captivating smile radiated warmth and kindness, while her fair skin glowed under the soft lighting. Despite exuding what most would call a welcoming aura, not a single soul had approached her with romantic intentions, while she observed her group of friends being showered all night with attention from men. 


Diane felt an overwhelming need to prove herself, to show that she was still desirable. She returned home with a determination, but also a sense of desperation. With shaking hands, she opened her laptop and clicked on the button to post a casual encounters ad. A mixture of excitement and guilt rushed through her as she waited for someone to respond to her request for physical validation.

Was this really what she wanted? Was it worth the risk?

As the night wore on and she lay in bed, wading through a vast mountain of replies that were making her regret ever having this idea, one message stood out from the rest. It was from a mysterious but intriguing man who went by the username ‘LuckyWinner’.

His attached picture caught her eye immediately – he had a kind and open expression, and he didn’t feel the need to show off his body or boast about his assets. Instead, he left things to the imagination and it was refreshing. And not only that, his messages were well-written and in complete sentences. 

She decided to just get straight to the point, don’t ruin it with a million messages back and forth, don’t find an excuse not to do it, just give him the address and hope he comes. Diane felt a mix of nerves and excitement as she waited to see if he would arrive. She didn’t actually know what kind of person he was, but the thought of finally getting some attention from a man filled her with anticipation. And holy fuck was she horny, especially every time she brought up his photo on her phone.

As the doorbell rang, Diane tried to steady her shaking hands. She opened the door to reveal a handsome bearded man with piercing blue eyes.  The picture was not a catfish at all.

“You must be Diane,” he said with a confident smile. “I’m Devin.”

Diane nodded, her cheeks flushing with excitement. She led him inside, her heart beating rapidly as she closed the door behind him.  She whispered to him that they had to be kind of quiet, because her roommate was there and she didn’t want to wake her up. So in the dimly lit living room, the two wasted no time as Diane began to slowly unbutton her blouse, revealing the lacy black bra that lay beneath. LuckyWinner watched her every move with keen interest, his eyes locked onto her every curve.

Finally, they reached Diane’s bedroom, LuckyWinner instantly noticed that her roommate was already fast asleep in a bed on the other side of the room.  He whispered, “you really want to do it in here right next to her?” Diane looked at LuckyWinner with a mix of excitement and apprehension. The thrill of doing something so daring and illicit was almost too much for her to bear.

“Yes, we just have to be quiet,” she whispered, biting her lip nervously. LuckyWinner nodded, a mischievous grin spreading across his face. He gently pushed Diane onto the bed, the two of them now completely naked.

As they began to explore each other’s bodies, Diane let out a soft moan, her pussy already wet with anticipation. LuckyWinner began to caress her breasts, his fingers tracing circles around her erect nipples, causing Diane to arch her back in pleasure. He then moved his hand down her toned stomach, finally reaching her eager pussy. He began to massage her clit gently, causing Diane’s eyes to roll back in pleasure.

“Oh god, yes,” she whispered, her voice barely above a whisper. LuckyWinner couldn’t help but smile, feeling a surge of power knowing that he was the one who could make this beautiful woman feel this way. He then began to slide his fingers in and out of her pussy, causing Diane to gasp in pleasure. As he continued to finger her, he leaned in and began to kiss her neck passionately, eliciting a soft moan from Diane’s lips. Finally, LuckyWinner couldn’t resist any longer. He positioned himself between Diane’s legs, his hard cock now pressing against her wet pussy.

Diane’s eyes were filled with a deep, primal desire as she gazed up at LuckyWinner. Her breath was hot and heavy against his skin as she whispered, “Yes, fuck me.” Without hesitation, LuckyWinner began a slow and deliberate pace, sliding his throbbing cock into Diane’s tight and eager pussy. A sharp gasp escaped her lips as she felt him fill her completely.

With each thrust, Diane’s body trembled with ecstasy, her moans echoing through the room. The thrill of possibly getting caught by her roommate only heightened the intense pleasure coursing through her veins. LuckyWinner’s movements became more urgent and forceful, igniting a fiery passion within Diane.

As they moved in perfect harmony, their bodies intertwined as one, their skin slick with sweat and desire. Diane could feel her climax building, her body tensing with anticipation until it burst forth in a powerful release that left her breathless and spent.

But LuckyWinner was not finished yet. His thrusts continued, driving Diane to the brink once again until she reached a second climax, her body writhing beneath his touch.  Finally, LuckyWinner pulled his cock out of Diane and it sprayed her entire body, some of it even spraying so far it hit her chin. 

Finally spent, they collapsed onto the bed, breathless and content. As they lay there, basking in the afterglow of their passionate encounter, Diane opened up to him about her struggles as a paralegal trapped in an unfulfilling job and he shared his own story as a creative professional working odd jobs to make ends meet. But in that moment, none of that mattered as they were lost in each other’s arms.

With every caress and kiss, their connection deepened, their bodies becoming one once again. And as they made love two more times throughout the night, Diane couldn’t help but feel like this was just the beginning of their secret rendezvous. With each thrust and touch, she knew that LuckyWinner saw past her fears and insecurities, awakening a newfound confidence and passion within her.

And even though their roommate was actually now awake, aware, and in shock of what was happening just steps away from her, Diane didn’t care. The whole reason she insisted on being in the shared bedroom was so it was known she wasn’t the only one who didn’t get any attention that night.  But that wasn’t on her mind anymore. In this wild and uninhibited night, nothing else existed except for the intoxicating rush of being together with this fascinating, passionate man while they were in each other’s embrace.

END.

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