Dean was having a party. He had invited practically everyone he knew and told them to bring whoever they wanted to. He just wanted one hell of a party like back in the old days. Beer and women. That's all he wanted this night.
His house was already filled up pretty good when his old friend Sami Callihan showed up. As expected he had a handful of women tagging along. Sami always did this and Dean didn't have a problem with it, especially not when he saw the tall one of them. She was something else. A bit taller than her friends and unlike her friends in their slutty outfits, she wore light blue jeans and a dark brown cami. He could see her bra straps and he imagined her in a matching black thong. Her feet were bare and she wore sandals which she immetiately took off the moment she was inside his house.
Sami introduced all the women to Dean but their names went in one ear and straight out the other. He couldn't take his eyes of this black haired beauty and only her name stuck with him. Isabelle.
He told them all to feel right at home and waved his hand out in the air to tell them to just go ahead. He was fast by Isabelle's side, taking her hand and kissing it, making her giggle a little.
"Welcome to by home, pretty lady," he said.
"Well, thank you, kind sir," she said.
He didn't let go off her hand. Instead he led her into the livingroom where he sat down on the couch next to her and immetiately started chatting with her.
The hours went by while they talked and drinked. He felt more and more aroused by her and he knew he wasn't gonna let her get away before he had gotten a taste of her. She had the most perfect ass and for the first time in his life, he welcomed it when a women got up to go to the toilet, just so he could watch that ass as she walked away.
"So, I found a deck of card in your hallway," she said as she dumped down in the couch next to him again. "Up for a game of poker?"
"You sure you wanna do that? I'm gonna wipe the floor with you," he chuckled.
"Guess we'll see about that," she said as she started shuffling the cards.
"Alright, since you're begging to lose, let's make it a little more fun. We don't play for cash. We play for... other things," he said with a twisted smile.
"Like what?" She asked.
"Whatever we feel like from game to game. But for starters, a kiss on the cheek in the first round," he answered.
"You're on," she laughed.
They started the game and he won the first round. He turned his cheek and pointed at it. She leaned in to kiss it and at the last second, he turned his head so her lips landed on his. They were so soft and it took a lot of self control not to just rip the cami to pieces while throwing her back on the couch.
"Cheater!" She laughed.
"I never said I play fair," he said and winked.
"Fine, round 2. What are we playing for?" She asked.
"Let's cut the childish games and move up in the grown up league. If I win, I get your bra," he said.
She looked at him. He knew it was a bold suggestion but he might as well throw himself out there like he usual did.
"Alright. And if I win, I get your boxers," she said.
He just laughed and nodded, happy to see that she was willing to play by his rules.
He lost but he didn't mind. He stood up and started opening his pants.
"Dean, for fuck's sake! Not here!" Sami yelled across the room.
"What? I'm not shy," Dean said.
"But we don't care to see it," Sami said.
"Fine," Dean said and sighed before turning his head to look at Isabelle. "Be right back with your prize."
He walked out in the bathroom. She turned her head and looked at Sami.
"What if he cheats and bring me another pair?" She asked laughing.
"Clearly you don't know him. He won't. He takes a pride in handing over his dirty underwear to a woman like you," Sami answered.
Dean came back shortly after and handed her his underwear. She laughed but accepted them. She folded them and put them in her bag.
"You ain't getting them back," she said.
She dealt the cards again and looked at them.
"Now, let's get some real prizes going," he said.
She looked at him. She didn't need to ask what he had in mind. It was clear in his eyes what he wanted. He wanted her, one way or another. She took a deep breath as she quickly thought it through. He was cute and he had been fun to be around all evening and she had to admit he made her feel something between her legs. Might as well have some fun. She leaned in so that no one could hear what she said in his ear.
"If I win, you're gonna go down on me until I cum," she said.
He looked at her and licked his lips, his way of saying he was on board. He leaned in to speak low in her ear as well.
"And if I win, I get to fuck you in the ass," he said.
She moved back quickly. That was not what she had expected him to say. Sure, she had expected some kind of sex, a blowjob or whatever position he liked to fuck in, but anal sex? Not an area she normally ventured to. She looked down at her cards. Two kings. No way she could lose this. He would have to have two aces then and the odds were just too small for that to happen. She looked back up at his face. He had his tongue sticking out of his mouth and a sassy grin planted on his face. God, she wanted to shove it to him and just let him work that tongue on her.
"You're in," she said and put down her cards with a smirk.
He looked at them and the grin didn't disappear from his face as she had expected. He put down his cards too. Two aces. What were the odds? All colour drained from her face but he didn't seem to notice. He just took her hand and yanked her up from the couch.
"Let's go," he said.
She followed him without any protests as he led her into his bedroom but her mind was working overtime. Could she go through with this? Could she get out of it? Would he accept a no? She had agreed to this. Why did she agree to this? When would she ever learn not to be so cocky when it came to playing poker? Just because she won 95% of the times, there was still that 5% where she lost and of course it had to happen now of all times.
She heard him lock the door and her shoulders dropped. The second she turned around to look at her, he grabbed her ass and squeezed tight. He pushed her up against the door and kissed her. He was a good kisser, she had to admit that. He took her hand and placed it on his crotch. She could feel his erection through his jeans.
"See what you do to me," he said in a voice that sent shivers down her spine.
She wanted him. She didn't wanna leave his room. He started undressing her and she allowed it. He took a step back to take in her naked body and he whistled.
"Damn girl!" He said and bit his lip.
She stood there naked, still leaning up against the door, as he started to undress himself. He was fast out of his shirt and pants and she knew for sure now that the boxers in her bag was the ones he had been wearing. He took her hand and led her towards the bed.
"On the bed on your hands and knees," he said and spanked her ass once.
She let out a yelp and quickly turned around to object but he had already his back against her as he was going through a drawer. She crawled up on the bed but sat on her ass instead. She really wasn't sure about this. He turned around with a bottle of lube in his hand and frowned as he saw how she was sitting.
"I said, on your hands and knees," he said as he walked towards her.
He crawled up in bed to her and sat on his knees. He towered over her and she suddenly felt small and powerless.
"Dean, I... I've never done that stuff before. Can't we just have normal sex?" She asked.
"You've never been fucked in your ass before?" He asked.
Damn, straight to the point with his words. She blushed and felt kind of stupid.
"No," she answered.
He leaned down close to her face, still towering over her though, and he scared and aroused her at the same time.
"We had a bet and you agreed to the terms. I'm collecting no matter if you like it or not. I can make this very pleasurable for you or I can make this very painful for you," he said in a threatening voice.
She looked up into his eyes. They had turned so dark and scary. She swallowed and nodded.
"Now, for the last time, on your hands and knees," he said.
She did as she was told, slowly turning around to the position he wanted. He ran his fingers over her ass as he made a grunt of satisfaction.
"Just relax," he said.
Easy for him to say but she tried. He started out easy with one finger, slowly making his way inside her as he spread the lube and stretched her.
"Not too bad, eh?" He asked.
"No," she whispered, confused about this new sensation that she actually liked.
She hissed as he added a second finger. Now that hurt more but he kept working them in and out of her at a slow pace, allowing her to slowly get used to it. As she started pushing backwards to meet his movements, he knew she was ready enough for him. He pulled out his fingers and moved behind her. The second the tip of his dick touched her entrance, she started second guessing the whole thing again.
"Relax. It'll only hurt at first and I'll go gentle. You just focus on relaxing," he said.
She gritted her teeth and nodded, afraid to say anything at all. She made a sound of pain as he pushed the head inside and instintly moved her body forward to get away. He was fast to grab her hips to hold her in place.
"Dean, please, that hurts," she said.
"Shh, almost there," he said as he continued to push himself all the way inside her.
He heard the sounds she was making and he knew he should stop but he didn't want to. He wanted to collect the prize he had won fair in a card game.
"There, hard part's over," he said and held still as he was all the way inside her.
He leaned down and kissed her back as he waited for a few seconds, allowing her to get used to this new feeling inside of her.
"You good?" He asked.
"Not really," she answered truthfully.
"You will be," he said.
He leaned back up, grabbed her hips again and slowly started thrusting in and out of her. She cried in pain as she tried her best to relax but this really wasn't something she liked. It was clear that he did though because he was lost in his own moans, not paying attention to her discomfort anymore. He got wilder and started thrusting in harder, only making the pain getting worse.
"Dean, stop!" She cried but he didn't hear her.
She pushed forward again with all her force in an attempt to get away from him but he just followed her body's movement until she was all the way down on her stomach with him still on top of her, thrusting in and out of her ass, making her cries of pain continue till he was finally done.
"Damn, Isabelle, I wouldn't mind tapping that ass again some other time," he said.
She didn't answer. What could she answer? He pulled out of her and gently let his fingers run over her ass again.
"Turn around," he said in a soft tone.
She raised her head and looked at him puzzled.
"You didn't win but I'm still gonna eat you out," he said and smirked.
She didn't know what made her do it but she rolled over on her back and spread her legs. He settled in between them and let his tongue run up her folds a couple of times before attacking her clit like a tornado. The pain she had felt before was nothing compared with the pleasure she was feeling now. She pushed her hips upwards, wanting more, demanding more, and he gladly gave it to her.
"God, Dean, keep going!" She yelled as she was close.
He kept moving his tongue around on her clit as he grabbed her thighs to keep her as steady as possible. She arched her back and cried out in pleasure as he made her cum. She laid there on his bed, her chest heaving after her orgasm. He had a smirk on his face as he crawled up to kiss her.
"Any complaints?" He asked.
Yes, she had plenty but she wasn't gonna let him in on that. He had gotten what he wanted and she had gotten what she wanted. No reason to talk about it anymore. They would never see each other again. That she would make sure of.
"No," she answered and got out of bed to get dressed.
He stayed in bed naked, just watching her get back in her clothes.
"You seriously got the perfect ass," he said as she reached for the key in the door to unlock it.
She stopped for a brief second.
"Thanks," she said and opened the door, disappearing out of it and out of his house.