Kevin was drunk, not that it was anything new. He had started drinking just after his mom was killed in a hold-up gone bad. That had been five years ago but today was different, he just didn't know how different yet.
His dad and new step-mom had planned this trip as a belated family get-away instead of taking a honeymoon. That meant everyone was here. His dad, his step-mom, his sister, and her husband and everyone seemed to be enjoying it ... except him.
As usual, he'd rolled out of bed just after noon and immediately had a 'bracer' from the mini-bar in their suite before heading down to the pool. The sun was bright and the breeze was warm. The women, dressed in their barely-there bikini's, were gorgeous and the bartender there always seemed to add a little extra alcohol to the drinks.
Within a couple of hours, he was drunk enough that he couldn't keep his mouth shut and that was what got him into trouble when he started bragging that there wasn't a woman around that he couldn't pick-up and fuck if he wanted to.
When one of the locals overheard him bragging, he approached him and said, "You're full of shit!! All your big talk and the only thing you can 'pick-up' is your fucking glass. I bet you couldn't even get one of the local whores to go to bed with you right now."
"Fuck you," replied Kevin with a slight slur.
"No thanks. I don't go that way," the local laughed.
"I can get any bitch around here in bed and fuck her before the day is over," Kevin boasted.
"Wanna bet?"
"Sure."
"How much?"
The local looked over at a group of friends and they gave him a nod. "Five hundred bucks but there are two conditions."
"Name them."
"Number one, we pick the woman and number two, SHE has to confirm that the two of you fucked."
"Deal."
For the next hour, Kevin and the locals sat at the bar checking out the various women as they walked by. Kevin even pointed out several that interested him but the locals always said 'No'. Then, suddenly, a woman appeared from inside the hotel.
Her hair was coal-black and it hung almost to the top of her well-shaped buttocks. Her skin was the color of light honey with a sheen from the sun-block she was wearing. Her lips were full and glistened in the sunlight from her lip-gloss. She wore sunglasses which kept the locals from seeing the deep brown eyes that Kevin knew were hidden beneath. She stood 5-foot, 5-inches tall but always wore 3 or 4-inch high heels just like she was now to make herself look taller and tighten the muscles of her sculpted legs. And to top it all off, she was wearing a metallic-blue bikini that barely covered her 34C-25-34 figure. She was every man's fantasy but at the moment she was Kevin's worst nightmare.
"That one," the local said as he pointed at the woman.
"I can't," Kevin mumbled.
"Listen, motherfucker, you said you could 'get any bitch around here in bed and fuck her before the day was over'. Well, that's the one if you want to win the bet. Now you either do it or pay up," he snarled.
"I ... ahhhhhhh ... I don't have ... well, it's this way ... I'm here with my family and so I didn't bring ..."
The local stepped closer, "... so you didn't bring any money," he finished as he clenched his fists. "Well, there are other ways to pay off your bet," a menacing looked appearing in his eyes.
Just then the woman appeared at Kevin's side. "Is everything OK, Kevin?"
"Yeah, just ... mmmmm ...," he didn't finish as he glanced at the local and then turned back to the woman. "Can I talk to you?"
"Sure, why don't you come and sit with me by the pool while I get some sun?" she called over her shoulder as she walked away.
Kevin followed quickly.
When they were seated, she asked quietly, "So what's going on and don't say 'Nothing'. I saw the way that guy was looking at you. Are you in some kind of trouble?"
"Well, actually, yeah. I had a little too much to drink ..."
"So what else is new?" she said, sarcastically.
"... and I opened my mouth ..."
"More surprising news."
"... and now I'm in big trouble."
"What kind of trouble?"
The events of the morning tumbled from his mouth as she sat there staring at him.
"You've got to be kidding!" she replied, her voice filled with disbelief.
"I wish I was."
"So let me get this straight. You either have to pay these guys $500, which you don't have, or have sex with me. Is that right?"
"Yeah."
"And I have to be the one to confirm that it happened?"
"Yeah."
"I see ..." she hesitated as she thought about what he had just told her.
The frown on her face slowly disappeared, replaced by a small smile as she got an idea. "OK, but IF we do this I have two conditions."
"What?" he replied in disbelief that she'd even consider helping and out of curiosity of what her conditions might be.
"Number one: No more drinking, and I mean none at all, unless I say it's okay. Do you understand? I mean not a single drop."
"Yeah, and what's the second condition?"
She paused as she looked at him and then replied, "We'll talk about that later but for now do you agree?"