by Tia Siren
“Wife send you in?” Dana asked.
“Something like that.” Gregory laughed, and then he held up his hand, showing that he wore no ring. “No wife, though. Not really a girlfriend either. Just a woman, I’m afraid. I hope you don’t think I’m some sort of lecherous worm.”
“Hey, your business is your own business, and if it means you’re buying from me, then it’s good business.”
“I’ve never had this request, I must admit,” the man said. “I’m certainly adventurous enough, but this young lady would like me to watch her…with one of her friends.”
Dana blushed again and nodded.
“Does sex embarrass you?” the man asked.
“No,” Dana whispered.
“I’m Greg,” the man said, holding his hand out. “Nice to meet you.”
Dana shook his hand, and then, after hearing his name, she realized she knew him. Well, knew who he was at least.
“You’re Gregory Jones,” she said, and the man nodded. She went on. “You founded CastMe.com.”
CastMe.com was a website that had grown popular over the two years since its launch. Wannabe actors, singers, and other entertainers could pay a monthly fee to post demos on the site. Then places like management companies and production companies that had partnered with the site could go and look for whatever they needed. More than a few new faces had been found for some big products, and everyone looking to make it big in entertainment was signing up. Greg had become a billionaire when he sold the site less than six months ago. Dana had known that Gregory Jones had grown up in her small town, but she didn’t know he ever came back.
“You visiting?” she asked.
“I moved home,” Greg said. “I’m just not a big city guy, though we’re close enough that I can scratch certain itches when need be.”
“Itches like seeing your new friend with another girl?”
“Exactly,” Greg said. “I must say, though, you intrigue me more than she ever could, no matter what lewd acts she does with her friend.”
“I intrigue you?”
“Yes. You’re beautiful, you own a store that sells cock rings and vibrators, and yet you blush when talking about those products.”
“I don’t normally,” Dana said, somewhat defensively.
“I’d like to take you to dinner. This weekend?” the man asked her.
“I don’t know,” Dana said, but she did know. She didn’t want to be some second fiddle to whatever floozy he was buying the strap-on dildo for.
She thought he would argue, but the rich man simply reached into his jacket pocket and pulled out a card. He handed it to her, and she looked at it. It simply had his name and a phone number. The paper stock was thick, as luxurious as such a thing could be.
“If you change your mind, call me,” Greg said. “Now, which of these strap-ons would you recommend?”
Greg didn’t linger in Dana’s store, though he lingered in her mind. For the rest of the day, after he was long gone, she thought of him. That night she lay in bed, the TV on, casting her in a soft blue glow, but she didn’t pay attention to the Gilmore Girls rerun. She had the card in her hand, and she turned it over and over in her fingers. She glanced at her clock. It was almost midnight. She wasn’t sure she should call so late, but she reached for her cell phone and dialed the number anyway.
When Greg answered, he was panting. She thought he might be sleeping, but it dawned on her that he was probably screwing. She almost hung up, but something kept her from doing so.
“Hello?” the man said.
“I’m in,” she said.
“Fantastic, Dana,” Greg said. He had asked her name as he was checking out. “Text me your address. I’ll pick you up Saturday at eight.”
“Okay,” Dana said, and hung up. She used her phone to Google Greg. He was thirty-two, almost ten years older than she was. His father had died young, but his mother was still living. He had been an aspiring actor, but after striking out in Hollywood, he had decided to start the website.
Dana set her phone back on her end table and turned her TV off. She was going out with a billionaire. She couldn’t believe it as she drifted off to sleep.
2
Friday passed slowly. Dana worked, sold her sex toys, and went home. She ate dinner and went to bed early. Saturday she worked as well, though she always closed the store early on the weekends. Most of her customers shopped during the week when the people they knew were at work. They should have been working too, but they stole in on lunch breaks or after dentist appointments, their mouths filled with sticky gauze, their speech slurred.
After work on Saturday, Dana rushed home and got ready. She showered and then dressed, though it took her almost an hour to settle on the perfect outfit: a small black dress with black high heels. She put on makeup, which she rarely did, and when she looked at herself in the mirror, she felt simultaneously bold and embarrassed. Bold because she looked like an absolute knockout and she knew it, and embarrassed because she knew she was doing it because she wanted Greg to want to fuck her.
She wouldn’t let him. That wasn’t the kind of girl she was, but she wanted him to want to.
He picked her up five minutes past eight. She had sent him her address the day before. She lived in a small apartment, and as she made her way to the parking lot, she felt ashamed. Surely he was used to penthouses when he was in the city, and now that he had returned to his hometown, an hour and a half outside of New York, she was confident he would build a mansion somewhere.
Apple Tree was the name of the town, and it was quaint, almost like a town people would live in on a TV show. Rolling green hills gave way to farm land—a far cry from the loud, smog-filled city to the south. There was a main street, and it was here where Dana lived, in a small row of apartments. Her shop was just outside town, on a lonely, dusty road that otherwise led out to a dairy farm.
Greg was driving a bright red convertible, which matched Dana’s lipstick. He had gotten out of the car and moved around to open the passenger door.
“You look amazing,” the rich man said.
“Thank you,” Dana said. “You too,” she added, and it was the truth. He was dressed in a black blazer with a crisp white button-up underneath it, the top two buttons undone, his bronze chest showing a small amount of curly chest hair. His pants were jeans, but not the sort you would buy at the local Walmart. They had cost more than her whole wardrobe; she had no doubt about that.
After she lowered herself into the driver’s seat, he came around and climbed in behind the wheel.
“You hungry?” he asked, and she nodded.
He took her over a few towns, to a sleepy little place called River’s Crossing. It had a reputation for being a bit more upscale than Apple Tree, and as such, Dana had never had much reason to go there, except for a couple of times with her girlfriends as they looked in the shops.
There was a small Italian restaurant there called Emilio’s, and the parking lot was full when Greg pulled in. The sky was black, and he had stopped to raise the roof on the convertible, as the air was growing quite chilly, despite the fact that it was summer. Though in a dress as short as the one Dana was wearing, any night would be chilly.
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 the main dining area. It only had four tables, each small and intimate with two chairs.
The food was better than any 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, that sort of thing. Surprisingly, Greg had dropped out of high school, moving when he was seventeen to Los Angeles, and his favorite film was Goodfellas. He learned that Dana had gone to a local high school and then a college thirty minutes to the East, and her favorite film was Eternal Sunshine of the Spotless Mind.
“I wo
uld 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 no.
“God yes,” she said instead, shocking herself.
“Great,” Greg said. He stood and left enough money to cover the bill and a hefty tip, and then 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 newly 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 kissed her. She let him, placing her hands on his chest as his strong hands found her hips. He tasted of the wine they had drunk at dinner, and of the gum 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, his fingers trailing over her dress along her stomach and 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 so his lips were on one of her rosebud nipples. She felt it harden against his tongue.
“Oh,” she said, letting out a long moan as he sucked on her nipple. His hand found her other breast, his fingers pinching and rolling the nipple. She reached for the back of his head, her fingers sliding through his short, curly hair. “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 that came in through the door causing her arms and chest to erupt in goose bumps. 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. It 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 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, though. She opened her mouth, intending to tease him, intending to take him slowly, 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 running 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 around 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 pre-cum, their tongues playing in the mess together.
And then he was pushing her backward, toward 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 pushed it into her.
He filled her up, his massive cock pushing into her tight, wet pussy. She groaned, moaned, buried her face into the carpeted stair. He pounded her, having no desire to be nice or sweet or to take it slow. His hands were everywhere, his strong fingers gripping her ass as it slapped against his pelvis. Then he had her hair again and was pushing forward to grope her tits.
She came quickly, 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 came, hot, thick globs of semen spraying from the head 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 sat 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 to find he had left a robe for her, folded over the edge of the sink, and she put it on and 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 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. 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’d ever had, 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 u
nspoken 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 answered.
“Hi,” she said. Simply talking to the man made her heart beat fast, and she felt her palms grow sweaty.
“Are you busy this weekend?” he asked her.
“I work on Saturday, but 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 when she answered.
“Great. I’ll pick you up tomorrow around six.”
Dana hung up and couldn’t stop 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 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 cut low 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.
