When Winning Isn't Enough by PickFiction,PickFiction

“Whoa,” he said. “You’re super wet, lady, so we better do something with that.” He was staring between her legs, and she could see him licking his lips. Maybe it was the excitement or the adrenaline, but she seemed to be recovering from the wine, and her senses were about to explode…and he hadn’t really touched her yet. Just thinking of what she knew was about to happen had her hips lifting to meet him.

What she had been thinking was beginning to happen quickly as she felt his hands spreading her, his eyes boring into her, and then his head dropping between her legs. His teeth gently nibbled on one labium and then the other, moving from top to bottom and then up again. More nibbles, a little harder now, and she squealed. His tongue began touching her, tormenting her as it was so close to her clit, but not touching. It flicked above and below, on both sides, occasionally slightly brushing the bright red nub, each brush causing her to moan and jerk.

He raised his head and smiled at her. “Would you like a little more,” he teased, “maybe like this?” and his finger began rubbing.

Her groaned “Yessss” was long and hard, which brought another smile.

His head disappeared, and she felt a sudden flick of his tongue, then his lips closed on that nub, and he sucked hard, his tongue caressing it as he did.

She wasn’t sure she could stand it as her hips involuntarily raised and pressed against his face. He only paused occasionally so his lips could grasp her more firmly, but his tongue was relentless, driving her toward the edge. She knew her moans were getting louder and louder, but she had no control. Then there was a loud and guttural groan as every nerve in her body fired at once, and the heat shot out from between her legs, inflaming her entire body. Her brain left her, and there were only the sensations, the pulsations, the spasming of her body to the final flicks of his tongue.

When she opened her eyes, he was smiling at her again.

“I think that was an okay one, wasn’t it. Haven’t seen an orgasm like that in some time. You’re okay, kiddo.”

Linda hadn’t seen or felt an orgasm like that in some time either, and she was okay for sure. But Bryan was moving and, even in her euphoric stupor, she knew what was coming next.

She was able to see him rolling the condom on that thing that she decided was way too big to go inside her, even though she knew that was what was about to happen.

“Maybe I can feel the same way,” he said, “and you’re just the one to make it happen.” He helped her move, so she was entirely on the bed. “I think I’m going to enjoy this.” He spread her legs once again and moved between them. She felt his fingers probing, first one and then two inside her. Finally, there were three and then all four as she felt herself stretching. “You’re a snug little thing,” he said, “but we’ll take care of that,” he added as she felt his erection parting her labia, then pressing inside her.

If his fingers had started stretching her, his cock was finishing the job. She could feel him pushing, and he was filling her completely, stretching her to meet his bulk until he bumped against her mons, where he stopped momentarily.

“Tight, but oh so nice,” he said as he began to move again. He settled his elbows beside her, his hairy chest pressed against her breasts, and began to move his hips. Out and in, sending feelings through her that were different than she was used to. His face was right above hers, but her eyes were closed as his thrusts became more intense. The hairy chest rubbing on her was causing her nippies to burn uncomfortably, but there was nothing she could do to stop it. He was grunting with every thrust now as his hips banged against her over and over. Her groans joined his as her arms went around him, holding on tight so his chest wouldn’t be sliding across her tender nipples.

“Oh yeah,” he murmured in her ear, misreading what was happening, but evidently it encouraged him to move faster and faster until, with a final groan, he stilled, and she could feel the pulses inside her, and, instinctively, she squeezed him as hard as she could.

His entire weight was on her for several seconds when the pulsing stopped, and she could barely breathe, but he seemed to realize that and was on his elbows, his eyes inches from hers that were now open.

“I don’t know,” he said. “With a body like yours, an orgasm like you had, and that tight little pussy of yours, you may be the best ever.”

She chuckled, not sure quite how to react, then bit her lower lip before she said, “With that cock of yours, I may have to look for a while to find something better.” She wasn’t sure how many times she’d ever said “cock” out loud, but it just rolled out this time.

“Glad you enjoyed it too,” he said as he rolled off her.

She sat up. “Mind if I use the bathroom?”

“Help yourself.”

She slid off the bed, suddenly conscious of her nakedness and the fact that she’d just had sex in her thigh highs and heels. She walked across the room, retrieved her dress and thong, and went into the bathroom, shutting the door behind her. There she was, looking back at herself from the mirror.

“You wanted daring, excitement, adventure, and whatever went along with it. Did you get what you wanted?” She could see her very red nipples in the mirror, and when she touched one, it was very tender. “That and a few other things, huh.”

She used a washcloth and some warm water to wash her breasts and her crotch. She dried carefully, put on the thong, and then the dress. Her hair was hopeless, but she tried to straighten it a little, not that she was likely to see anyone but Bryan now. Satisfied, she left the bathroom and found him fully dressed and wondered if he’d head for the bar for a possible round two. Hopefully, he had plenty of condoms.

“Listen,” he said. “I hadn’t imagined a night quite like this, but you…well, you were totally unexpected.” He handed her something. “I don’t usually do this, but that’s my business card. I’ll just leave it at that,” he added, smiling.

She slid the card into her clutch bag as he moved toward her. “You seem stable now, so I won’t offer to take you to your room. He leaned in and kissed her on the cheek. “Thanks for a wonderful and exciting evening.”

“No problem,” she said, smiling. “It was an exciting evening for sure.”

“Have a safe trip home, Lucy.”

She’d nearly forgotten. “You too.”

Lucy closed the door behind her, checking that the hallway was empty. Linda didn’t need to be seen here.

In her room, she stripped off the dress and thong and put on her pajamas. When she had left the room in that outfit, she was only vaguely aware of what to expect. What she got was a little more than she had anticipated, probably because her anticipation had been purposely vague. Still, it was what she wanted and needed, and now she could crawl into bed and sleep, waiting for the wake-up call from the handsome assistant coach who’d be driving her to the airport.

She was still curious about Bryan and went to the clutch purse to check the card he’d given her. When she pulled it out, something came with it, and her breath caught in her throat. She picked it up and unfolded it…four one hundred dollar bills. Obvious thoughts raced through her head. One side of her wanted to go to his room and slide it under the door, while the other side was saying she didn’t ask for the money and hadn’t expected it. He was just tipping her, kind of like a server at a restaurant who’d given good service. She sighed at her weak efforts to resolve the issue. She finally decided it was simply a part of the daring excitement she was seeking and was a fringe benefit.

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