by Tia Siren
They went inside, and Dana thought they would have to wait. There was a line almost to the door, but as soon as the hostess saw Greg, she came forward and showed them to a small private room off of the main dining area. It only had four tables, each small and intimate with two chairs.
The food was better than Dana had ever had, and the conversation was just as good. They did the normal first date stuff, working through the conversation they were supposed to. Where did you go to school, what movies do you like? Surprisingly, Greg had dropped out of highschool, moving when he was seventeen to Los Angeles, and his favorite film was Goodfellas. He learned that Dana had gone to a local highschool and then a college thirty minutes to the East, and her favorite film was Eternal Sunshine of the Spotless Mind.
“I would love it if you came home with me,” Greg said, and Dana was shocked by how upfront he was. She opened her mouth after she smiled, and she was prepared to tell him now.
“God yes,” she said instead, shocking herself.
“Great,” Greg said, and he stood and left enough money to cover the bill and a hefty tip, and they hurried out to his car.
It turned out that Greg had done exactly what Dana had thought he must have. Twenty minutes out of Apple Tree there was a massive home that had been freshly built. The immense gates they drove through before heading down a winding drive to get to the house answered how exactly the house had gotten past the attention of everyone in town. She doubted anyone knew the house was here, sitting on some unused farmland, far from the main road.
They made it in through the front door and into the foyer before Greg turned to her and was kissing her. She let him, placing her hands on his chest, and his strong hands found her hips. He tasted of the wine they had drunk at dinner, and of the gum which he had been chewing since. She parted her lips to him, and their tongues met and danced briefly together, and then he was breaking the kiss, and Dana found herself disappointed. The disappointment didn’t last long. Greg moved one hand up, fingers trailing over her dress along her stomach, up over a breast until he reached her skin. Then those fingers curled into the front of her dress and pulled, forcing the material down, and freeing both of her breasts. She wore no bra, the dress wouldn’t allow it, and Greg bent, and his lips were on one of her rosebud nipples, and she felt it harden against his tongue.
“Oh,” she said, a long moan as he sucked on her nipple. His hand found her other breast, fingers pinching and rolling the nipple there. She reached for the back of his head, fingers sliding through the short curling hair there. “Bed,” she groaned.
“No,” he said, straightening and looking at her. The front door stood open behind him, and he was framed in silver moonlight. Behind her was a grand staircase, leading up to the second floor. The ground here was hard; it looked as though it might be polished marble, and Dana almost balked when he commanded her. “On your knees,” he said.
But she didn’t resist him. She knelt down, her bare knees going to the hard floor. She reached for his fly, knowing what he wanted, but he slapped her hands softly away. “With your mouth,” he said after he used one practiced hand to unbutton his fly.
Dana leaned forward, her large breasts heaving in the dim light, the breeze coming in through the door causing her arms and chest to erupt in goosebumps. Her lips brushed against the fly of his jeans, and then she curled them back and used her teeth to take his zipper and tug it down. She reached up again, but he grabbed her by the back of the hair and pulled her away.
“Don’t touch my cock with anything but your mouth or your pussy, do you understand?”
Dana nodded. She looked up at the man as he reached down and pulled his cock out through his open fly. His member was massive, throbbing in the air, red and angry with veins running along it.
Greg still had a hold of her brown hair, and he tugged her close. The bulbous head of his cock pressed against her cheek. He pulled her into a better position, and it pushed against her lips. He was pulling her hair so hard it hurt, and she felt her eyes water. She didn’t want him to stop. She opened her mouth, intending to tease him, intending to take him slowly into her wet oral orifice, but the rich man had other ideas. She knew he wasn’t a man used to waiting; she knew he was the kind of man who would always get his way. He was rich, a self-made billionaire, and he was going to fuck her mouth.
He held her head still with one hand and thrust his hips forward. His cock was buried in her mouth, pushing against the back of her throat. She gagged, mascara ran down her cheeks. His balls slapped against her chin, and then he was pulling out of her mouth. Before he fell fully away from her lips, he thrust forward again. He was using her, fucking her mouth roughly, the way a man who couldn’t contain himself would fuck a pussy. She slobbered and cried and wanted it. He was using her, Dana, the vanilla sex girl who owned a sex shop, who was always on the bottom, who always spit and never swallowed. He fucked her mouth, and she loved it.
She thought he would finish that way, thrusting in and out of her mouth, feeling her pillowy lips on the sides of his massive penis. But then he pulled away from her, a long string of saliva connecting them for a minute, the spit stretching from her bottom lip to the head of his cock, which bobbed once more in the air. He was still gripping her by the hair, and he lifted her up, so she was standing. He kissed her, her wet mouth, slick with her spit and his own precum, their tongues playing in the mess together.
And then he was pushing her backwards, towards the staircase, and she thought he would take her up it, to his bedroom, but he didn’t do that. He turned her around just as her heels came into contact with the bottom stair, and then he pushed her over. She went to her knees on the third step, and he knelt on the second.
Her pussy was wet, slick, yearning for his cock. He pushed her dress up roughly and pulled her panties away with such force that the small thong ripped. He tossed it to the side and grabbed her ass. She felt his hard cock against her slit, and she reached down between her legs, so she could guide him into her. As soon as her fingers brushed the skin of his cock, however, he reached forward and grabbed her hair, tugging her head back so violently and painfully that she screamed out.
“I said don’t touch my cock with your hands, you slut,” he whispered, and she nodded as best as she could since he was still holding her hair. She moaned and whimpered, and he let go of her hair. He reached down, taking his dick, wet with her spit, and he pushed himself into her.
He filled her up, his massive cock pushing into her tight wet snatch. She groaned, moaned, buried her face into the carpeted stair. He pounded her, no desire to be nice or sweet or take it slow. His hands were everywhere, strong fingers gripping her ass as it slapped against his pelvis, and then he had her hair again, and then he was pushing forward to grope at her tits.
She came quickly, the young girl screaming out as an orgasm rocked her, wet warmth spreading from her loins to the rest of her body as her pussy walls tightened and contracted against his cock. And still he fucked her.
When he was about to come, he pulled out of her and took her by the hair once more, pulling her roughly down and around, his other hand pumping at himself. And as soon as she was on her ass a stair below him, he was coming, thick white hot globs of semen spraying from the redhead of his cock and splashing across her face. One strand fell over her painted lips, another across her left eye. He came on her, his cum thick and warm. And then he walked past her, up the stairs without a word. She leaned back, panting, trying to catch her breath. When he came back down, he was dressed and showered, and she wondered how long she had been like that.
“You still intrigue me,” he said, sitting next to her. His cum was drying on her face, and the cold air from the open door kept her nipples hard. He reached over and pinched one. “Go take a shower, and then let’s get drunk and do that again.
She smiled and nodded. Upstairs she found the bathroom and took a shower. After she was surprised that he had left a robe for her, folded over the edge of the sink, and she put it on a
nd went back downstairs. She found him in a small room with a bar built into the wall, and he poured them both a drink. They sat together on a small couch, and after they had drank and laughed, he fucked her again, him on top, holding her roughly down. He finished first that time, but he instructed her to pleasure herself while he got something, and she did, sliding her fingers in and out of her wet snatch. When he returned, he had a purple dildo.
“I’m going to fuck you with this,” he said. It was large, bigger than his own enormous dick, and Dana was frightened, but she just nodded. He knelt down between her legs and licked her clit while he pushed the toy in and out of her. It was the second most intense orgasm she had ever felt, the first being the one he had given her on the stairs. If the rich man was intrigued by her, she was doubly intrigued by him.
Later that night they lay in his bed, she accepting his unspoken invitation to stay. She asked him if he ever made love, and he smiled, kissed her, and they did that too. When she woke the next morning, they showered together, going down on one another, and then finally it was time for her to leave. He drove her home, kissing her before she got out of the car, and she watched him drive away.
3
Days passed after the first date, and Dana didn’t hear from Greg. She accepted the fact that it had been a one-night stand, and her life got back to normal. On the next Thursday, however, while Dana was ringing up a customer at her shop, her cell rang. She finished with her customer and then fished it out of her pocket.
“Hey, Dana,” Greg said when she had answered.
“Hi,” the young girl said. Simply talking to the man made her heart beat fast, and she felt her palms grow sweaty.
“Are you busy this weekend?” the rich man asked her.
“I work on Saturdays, the shop is closed on Sunday.”
“Can you close it Saturday too?”
“Why?” she asked.
“I want you to come to the city with me. I’ll be there all weekend, but I only have a meeting Saturday morning. I thought we could have some fun,” Greg said.
“What kind of fun?”
Greg laughed. “All kinds of fun.”
“Let me think about it,” Dana said, and they hung up. He called her again later that night after she had closed up her sex shop and returned to her small apartment. By the time he had called, she had already packed a bag.
“I’m in,” she said as she answered.
“Great, I’ll pick you up tomorrow around six.”
Dana hung up and couldn’t hide a smile from spreading across her lips.
She closed The Treasure Chest early the next day and hurried home so she could shower and dress. She once again wasn’t sure of how to dress, but she figured for a drive to New York City she should be comfortable, so she settled on shorts and a loose shirt that was low cut enough to show off some cleavage.
Greg picked Dana up in the same cherry red sports car, but once he was on the highway, he headed away from New York.
“Where are we going?” Dana asked.
“I hate driving into the city,” Greg answered cryptically though it didn’t take long for Dana to discover his meaning. He pulled off of the highway, and ten minutes later, he was parking in the small lot of a tiny airport. On a nearby black top tarmac, there was a helicopter, the pilot inside already, and the rotor blades beginning to turn.
Dana had never been on a helicopter before, but her nerves were overpowered by a sense of excitement and adventure, and soon she was hundreds of feet in the air, the ground a blur as it slipped song below them.
As interesting as the ride was, nothing could have prepared the young woman for landing on the roof of a massive skyscraper. She was led inside, and to a penthouse apartment, where they dined and then made love.
The weekend was a blast, Greg only disappearing for his meeting on Saturday morning. They saw the sights for the rest of the day and then retired to the penthouse for more food, wine, and sex. Sunday they planned to go to a local museum, but they never managed to leave the bed. They returned to Apple Tree early Monday morning, and after being dropped off once more at her apartment, Dana hurried to open the shop.
Bad news was waiting for her. She was behind on her bills for the shop, and the bliss she had felt that weekend was quickly washed away. She called up a realtor. She would have to sell the place.
Greg remained in her life, calling her that evening. As the weeks wore on, she met him more and more, and they fell into what could only be called a relationship. She never bothered the rich man with her problem; she didn’t want to borrow money from him. She would never want such a powerful man to have that much power over her. She was enjoying their relationship, but she wasn’t sure she was ready for anything more than the dates and the screwing.
He was rich, and it opened Dana to a world that she could have never imagined she would ever be a part of. The extravagance, the seemingly wasted money. Dana often teased the older man on what she would do with so much money. “I would give most of it to charity,” she said from bed one evening.”
“Which charity?” Greg asked, a smirk upon his face.
“A lot of charities,” she said, and he had laughed and nodded.
The problem with the sex shop seemed to be resolved in a better way than Dana could have hoped for, a month after she put it up for sale. Someone had purchased it, apparently a businessman from across the country. He wanted to keep the business open, and wanted her to run it. The only real difference, other than the fact that she didn’t own The Treasure Chest anymore, was that she was now drawing an actual salary.
“Did you buy my shop?” Dana asked Greg over dinner one night. They were back in New York city, having flown in on Saturday, and planning on staying until Sunday night.
“What?” Greg asked, looking at her. He had found out about her problems a week before the shop was bought. She had been stressed out on one of their dates, and after a couple of glasses of wine, he had gotten the whole story out of her. He had promised her not to get involved, however.
“A man named Mr. White bought the shop. Some mysterious business man from California. Wants me to run the place. Was it you?”
“My name isn’t Mr. White,” Greg said, smiling and cracking a joke.
“I know it isn’t, but I haven’t met him or anything, he’s just some mysterious rich man who wants my business?”
“Sex sells.”
“Not that sex. The internet is killing me. He won’t make money.”
“He must think he will, eventually.”
“Did you buy it? I don’t want your help.”
“I know,” Greg said. “It wasn’t me.”
“You promise?””
“Yes.”
“Alright,” Dana said, and she smiled across the table at her lover. “What are we doing tonight.”
Greg smiled. “I have a surprise for you actually.”
After dinner, they returned to his penthouse, the massive open space in the skyscraper they had landed on once more after flying into the city. Greg led the way out of the elevator, heading down a long hall to the only door there. He unlocked it with a keycard, as he did each time they visited the room. Flickering light met Dana as she stepped inside; there were, at least, a hundred lit candles in the open living room, and more leading back towards the far corner of the massive apartment, where a king sized bed sat under a long window with an impressive view of the city.
“Romantic,” Dana smiled, looking over at Greg as he shut the door and locked it behind them.
“Wait,” he said, and then he motioned towards the bedroom, and she went that way. She was wearing a red dress and matching heels, and she stopped for a moment to bend and take them off, but Greg stopped her. “Do what I tell you. Don’t undress yourself. Go sit on the bed.”
Dana nodded, her heart rate already elevating. It was going to be one of those nights. He was in charge. He would dominate her, and she would do what he said and wanted. Dana had no idea just what that would entail.
She perched on the end of the bed and looked up to him. He stood before her, reaching into his pocket and pulling his cell phone out. He dialed a number and held the phone to his ear.
“Come up,” he said.
A single thought flashed through Dana’s head. It was the woman with the strap on, coming to fuck her while Greg watched from the highback easy chair in the corner.
“I don’t think I’m ready for a woman,” Dana said, but Greg just glared at her, and raised a finger to quiet her as he hung up and slid his phone back into his pocket.
“I’m in charge,” he said, and then, as he turned and left, he added, “Stay here.”
Dana did so, her pulse pounding, the idea of being with another woman freezing her in place. It was frightening. She didn‘t even swing that way remotely; she had never been curious about women. She was so reserved, something that she had been working through with the help of Greg, but this, it was just too much.
And then Greg returned, and the young woman in the red dress found that her fears were unwarranted. They were entirely misplaced. Greg did return with someone, but it wasn’t some busty bimbo with a big black strap-on jutting from delicate hips.
It was a young man.
4
He looked to be about twenty, and he had blonde hair which fell to his shoulders, and skin so tanned it could be called olive. Dana thought he might be foreign, and he confirmed it when he spoke to her, his accent something from the Mediterranean.
“Lovely woman,” he said, and Dana couldn't be sure if he were talking to her, or about her.
“This is Homer,” Greg said, motioning to his friend. Dana thought the name didn’t suit the man, but she smiled in the soft candlelight and nodded.
“Hello,” she said.
“Stand up,” Homer said in return, and Dana looked to Greg.
“You’ll do as I say, and I say you do as Homer says,” the older man said, and Dana stood, suddenly self-conscious in her thin dress. Homer stepped forward, and she could smell his aftershave and expensive cologne, and she could feel the heat from his body. He was wearing a pale blue button up shirt, the first three buttons undone so she could admire his toned and hairless chest. His pants were tight, his shoes expensive Italian leather. All things Dana had come to admire and appreciate since dating a billionaire.
