Bad night gets better

Ruby was unhappy. Actually, as she slammed her cell phone down, she was pissed. Nothing today had gone right. Work sucked, and the only thing that had gotten her through it was the thought of meeting her friend Sandy for some drinks and a ladies’ night out. Even out in the parking lot, she had dinged some stranger’s door getting out of her car. Just NOTHING had gone right, and now Sandy just called and said the baby sitter had the measles or something and she couldn’t come out. So here Ruby sat, all dolled up in her favorite purple dress, but alone, pissed off, and not feeling very much of anything except unhappiness.
To take her mind off of her misery, she scanned around the bar. Geez, did EVERYONE have to be with someone? It had been a while since Ruby had received any “attention,” and she probably would have been a little more randy if she hadn’t been so bloody angry at the world. As she scanned around, her eyes did come to rest on one man, enjoying a drink while talking to the bar tender. He was fairly attractive, and well dressed in slacks and a silk shirt, and she noticed he had the deepest green eyes. But he was pretty well engrossed in his discussion, and other than that, the well was pretty dry.
“Fuck it,” she muttered under her breath. “I’m outta here.” She put her phone in her purse, gathered herself, and she got up to head back to her car in a huff. As she turned around, SMACK, she ran right into the handsome stranger from the bar. Only he wasn’t as handsome as he was a few moments ago, as the impact had spilled his red wine all over the front of his not-nearly-as-valuable-anymore silk shirt.
He wasn’t happy it at ALL, but handled it like a gentleman. “Don’t worry about it,” he said through almost clenched teeth.
“Oh, I’m SO sorry,” Ruby stammered. “Can I at least get you another drink.”
“No, that’s alright,” he replied. “Can’t really stay here looking like this anyway. I’m going to head home.”
“I was just leaving myself, after a miserable evening. I can at least walk out with you.”
“Fine,” he said, obviously just wanting his evening to end as well.
There was an uncomfortable silence as they walked out the door and through the parking lot. Ruby noticed they walked in generally the same direction, and she suddenly was horrified at the thought that of all the cars in the parking lot, she might have actually dinged HIS.
Her fears were realized when he walked right up to the hunter green jag with the beige interior that was parked right next to Ruby’s car. Even in the light of the parking lot, the ding from Ruby’s door was more than visible. The man quickly put two and two together, and was even less than happy.
“I’m SO sorry, again,” Ruby tried to spit out.
The man was visibly annoyed, but tried to keep an even tone. “Let me get this straight. First, you ruin my drink and my shirt, and second, you ding up my car. Lady, you have had one BAD evening.”
“Tell me about it. Again, I’m sorry.”
“Hmm. Well, the way I see it, I could let you off for the shirt OR the door, but not both. Get in.”
“I, I…,” she stuttered.
“Get IN.” Ruby complied. She was a little frightened. On the one hand, she didn’t know this guy from Adam. On the other, he was well dressed, obviously well to do, and attractive. Besides, she had this FEELING about him, that he knew where the line was and wouldn’t cross it (though he might get close).
They drove in silence for a while, toward the rich part of the city. The man didn’t say much, just put on a country station and drove, quickly but smoothly, to one of the mansions on the outskirts of town. A small mansion, but a mansion nonetheless.
She didn’t say much, but followed him into the house. It was dimly lit, but she could see the opulence even in the low light. He showed her to the sitting room and fixed her a drink while he lit some candles and started a fire. She looked around at the collection of books on the wall, and at the fine furnishings, and at the big bearskin rug on the floor. She was less apprehensive, but no less excited, that she had trusted her instincts.
As the fire began to roar, they sat down on the couch. In the fire, with the wine in her hand, and considering her lack of recent attention, she was more than a little drawn to this man. But making the first move was not her strong suit.
Thankfully, it didn’t matter. “Well, my name is Tom, for starters.”
Ruby thinks she heard herself say her name, but she wasn’t focused on that at the moment.
“The way I see it, we were both having a miserable night alone. And, since you ‘owe’ me a little something for the car and the shirt, I figured we could have a less miserable night together. Do you agree?”
She felt herself nod, lost in those green eyes. And with that, he leaned in, and kissed her passionately. Their tongues mingled in a long hot kiss, and she felt his hands begin to roam over her body.
After a seemingly endless kiss, he abruptly stood up in front of her. “Suck my cock,” he commanded. Ruby almost came right there. She LOVED a man who was in control. She tentatively unbuckled his expensive slacks, and they hadn’t even hit the floor when she reached into his underwear and felt his cock, already beginning to swell. It was large, but not overly so, and she eagerly put it into her mouth as he tilted his head back and moaned.
Ruby LOVED sucking cock, and for all her shyness, she knew she was good at it. She felt him begin to harden, and she gently reached her hand up to work his balls. They were heavy, and she was worried that this would be over too soon.
Tom quickly allayed that fear, as he pulled away from her. Still in command, he firmly spoke to her. “Stand up and turn around.” She obeyed, and as she did so felt him unzip her dress. As it fell to the floor, he gently pushed her forward, so that she was leaning over the couch. She didn’t know what to expect, but her lover didn’t keep her waiting long. Her panties were quickly removed, and she soon felt his hot breath on her dampening pussy. Before long, he was eating her from behind for all he was worth.
It felt so damn GOOD. It had been a long time for Ruby, and she ground back on his face and began to moan. He was an expert cunt licker, and showing off for his new friend for sure. His tongue worked in and out of her hole, and he pulled on one labia and then the other with his lips. Just as she thought she was going to lose it, he stopped.
She was almost disappointed, until she saw him wiggle out of his slacks and lay down on the thick bearskin rug. Accepting his silent invitation, she mounted his face for a 69, and his tongue immediately went back to work on her aching pussy. For her part, she dove back on his cock, licking the shaft up and down before putting as much of it as possible into her mouth. Her evening was getting a LOT better.
They continued pleasuring each other for some time, both so focused on the other’s pleasure that their orgasms were held off. As Ruby was lost in the delicious pleasure of oral sex, she suddenly felt something she hadn’t felt before. Her new friend was teasing her anus!
As he continued to lick her flowing juices, he slowly began circling her rosebud with his finger. Ruby couldn’t believe this. She had NEVER had an anal experience before. But she was lost in the moment, and too worked up to protest. Besides, she still had a mouth full of Tom’s wonderful cock!
Tom grew bolder, hearing no objections, and inserted the tip of his finger into Ruby’s tight ass. She couldn’t BELIEVE how good it felt, and all of a sudden her orgasm swelled up inside her and she ground down on Tom’s face and came so hard she almost blacked out. Her juices flowed over his tongue, and her asshole spasmed around his finger. She cried loudly as she came, and that was enough for Tom.
He began moaning faster, and Ruby, still coming off her orgasm, placed the tip of his cock in her mouth and began pumping his shaft with her hand. Almost immediately, he moaned loudly and began erupting. She continued to tease his cockhead with her tongue while she had her mouth on him, and he just continued spurting. She grabbed his balls and massaged them, and she had so much cum in her mouth that it overflowed and ran down his shaft, making it even wetter as she continued to pump it.
Exhausted, they just collapsed and lay there for a long time. Ruby lost track of the time, but soon they were picking themselves off the floor. “Follow me,” he said, and led her upstairs to an elegant bathroom, complete with towels and a robe. Tom lit some candles, and left her to freshen up.
She took a wonderfully hot shower, delighting in the feeling of this magical evening, though she was still a little apprehensive about her mystery man. Where was this going? As the shower hit her body, and she reveled in the feeling emanating from within, she decided to just go with the feeling.
After the shower, she dried off and slipped into the luxurious bathrobe that was left for her. Wondering how she would find Tom, she poked her heat out the door, and saw a trail of rose petals leading down the hallway. Damn, this guy was good.
The trail led to a large master bedroom, which was dark except for the candles surrounding the bed. She moved to the bed and stretched out. From the shadows, her lover joined her. “I was wondering where you were,” he whispered.
And then she was in her arms, feeling his nakedness against hers as the robe fell to the floor. They kissed passionately, and soon she was on her back on the bed with her lover tonguing her freshly washed pussy. It didn’t take long for her juices to begin flowing again, as he expertly worked her clit with his tongue while inserting first one, then two fingers into her hot tunnel. She grabbed his head with her hands, and massaged him as he drove her closer to ecstasy.
She didn’t know how long the glorious licking went on, but soon she felt another orgasm well up inside her. She began bucking her hips against his face, and he massaged her hole faster and faster while his tongue blazed away on her button. Her breathing grew shorter and shorter, and just at the right time he removed his fingers from her pussy and replaced them with his tongue, at the same time inserting that wonderful finger just into her anus. Game OVER.
“I’M CUUUUUUUUUUUUUMMMMMMMMMMMMMMMMIIIIINNG!” she screamed, as her eyes rolled back and her whole body convulsed. He must have been some kind of contortionist, because he kept his tongue firmly inside her through the whole wild ride. As she was coming down from her climax, she felt his strong hands turn her over onto her stomach, and Tom entered her from behind.
She was completely filled up on the first stroke, and it felt wonderful. He really knew how to work a pussy, as he slid in and out with full, deep strokes, changing the rhythm and the direction every few seconds to keep it interesting. Ruby would have come right away if it wasn’t for the mind blowing orgasm she had just had. But that previous release enabled her to just hold on and enjoy the ride.
Tom fucked her for almost ten minutes, an amazing display of control, considering how tight she was. Ruby loved the feeling, but a little bird in her mind was worried about the whole birth control thing. Tom was moving faster and faster, and she sensed it would be over soon.
Apparently, he was reading her thoughts. “I want you on your back, baby,” he commanded. “I want to fuck your beautiful tits, and come all over you.” Normally, Ruby was not a big fan of the porn-movie facial, but after this evening, she couldn’t wait to please this man. She just moaned, and rolled over as she felt Tom pull out of her.
Flat on her back, she waited. Tom climbed over her, placing his very hard cock, slick with her juice, between her tits. She pushed them together, to increase the friction, and soon his eyes were closed as he thrust between them.
Faster and faster he pushed, and his breathing grew shorter and shorter. Finally, with a load moan, his head rocked back and his cock began to twitch. She grabbed it and began to jerk him off as he erupted. Hot cum flew onto Ruby’s face, and she opened her mouth to catch as much as possible. Despite the hard orgasm he had only hours before, there was still an incredible amount. Three, four, five thick jets of spunk landed on her face, tongue, and tits, and she was surprised at how much she enjoyed it and how erotic it all was. Just as he finished, she felt a small orgasm come and go just from the sheer excitement of it all.
Her lover collapsed on top of her, and they lay there for a long time. Sadly, Ruby had to work, the next morning, and had to get home. As they hugged, Tom summoned his butler to drive Ruby back to the bar for her car.
“Will I see you again?” she asked as she got in the car. He just smiled, and as the car drove off she could see him standing there, watching.