by Tia Siren
“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.
Homer didn’t ask before he touched her. He seemed to be taking his role as another dominant man seriously His hands went to her hips, and then his body was pressing against her, and Dana was proud of herself for a shining moment when she felt his hard on pressing against the bottom of her flat stomach.
Before she could register anything else, he was kissing her, young and forceful, his tongue pressing against her lips until she parted them to him. She felt her arms go around his body, without being conscious of doing it herself. Her hands pressed against his back, taut with tight young muscle. The kiss broke, and he lowered his lips to her neck, his white teeth nibbling there as Dana tilt her head back. She opened her smoky eyes just enough to see Greg there, still standing near the entrance of the room. He was watching as the younger man bit and sucked on his girlfriend's neck.
“You like to watch?” Dana teased, taking to what was happening quicker than she had imagined she would.
“I’ll do more than watch,” her boyfriend promised her, and then Homer was taking her face in his hands and tilting her head down so he could kiss her again.
“Stop,” Greg said, after a minute of kissing between Dana and Homer. The younger man stepped away immediately. Dana was breathless, her nipples hard and pressing noticeably against her dress, her pussy slick and moist under her panties. Both men stared at her large breasts, and Greg smiled.
“Take off your dress,” he said, and slowly, teasingly. Dana did so, pulling it up and over her head. She tossed it to the floor, and then bent to take her heels off.
“Leave them on,” Homer commanded, and Dana did so. She stood there in front of both men, naked save for the shoes and her panties, tight red boy shorts.
“Turn around,” Greg said, and once again Dana did as she was told.
“Wow,” she heard Homer breathe, and she smiled. She knew she looked good. Men always stared at her breasts if she was facing them, and if she turned, she caught them staring at her round ass. The boy shorts only served to make her ass sexier.
“Bend over,” Homer said, coming forward as she did so, pressing his pelvis against her ass. She found herself wanting him to disrobe, so he could slide inside her pussy, but he didn't. He just rubbed against her, while his hands explored her backside, sliding up over her back, and then coming back down to take off her panties.
“Lay down,” Greg commanded, and Dana turned and sat on the end of the bed, and then she lay back while sliding upward so her head rested on the pillows. She stared down at the two men. They were looking at her, now nude except for the heels.
“Spread your legs,” Homer said, and Dana did so without shame, revealing her wet pink snatch. “Finger yourself,” the young man added, and Dana reached down, trailing the tip of her index finger down her stomach and across her trimmed pubic hair, until she was sliding along her slit and then pushing her finger into her own snatch.
The men watched her for some time, and she gave them quite the show, sliding two fingers into herself and then three. As she was coming, fingering herself with those three fingers while using the pad of her index finger on her other hand to rub her clit, Homer took his pants off, stepping out of them and his boxers, and began pulling on his own cock. He was large, not as girthy as Greg but somehow even longer. He was uncut, something Dana had never experienced. Dana moaned and came, making eye contact with Greg as she did so.
“Taste her,” Greg said, and Homer took his shirt off as well before climbing onto the bed and lowering his head between Dana’s legs. She had just come but the young man’s tongue was like heaven between her legs, and he eagerly lapped up her expelled juices. She reached down and ran her fingers through the man's long blonde hair.
“Fuck her,” Greg said, and Dana opened her eyes and looked down, seeing that Greg was now nude, having moved to the chair beside the bed. His cock was hard, and he was stroking it slowly while he watched Homer move up, positioning his pelvis between Dana’s spread legs. The man was gentle, somehow suppressing his young man urge as he slid into her wet pussy. He fucked her slowly, gently, their lips meeting in between moans and groans.
The bed shook, and Dana looked over. Greg was kneeling beside her, his massive cock bobbing in the air above her lips. She opened her mouth, and he came forward so that his dick slid into her mouth. His hand went to her breasts as she rocked her head back and forth, sucking his cock as Homer continued to slide in and out of her pussy.
This went on for some time, and then Homer pulled out of her. “I want to feel her tongue,” he said. Greg pulled back, his cock springing free from her lips, wet and slick and shining in the soft candlelight. They moved her then, roughly, where the sex had been gentle to that point. Greg was not going to show the same constraint, and Homer fed off it. They positioned her on her hands and knees across the bed, and Homer knelt before her face. She opened her lips, and he reached down, placing one hand on her chin, gripping her there painfully as he shoved his cock down her throat.
Greg took up position behind her, his hands on her hips, and he thrust his monster dick inside her tight snatch. The men took no more concern with her pleasure, but still, within minutes, she felt herself being rocked by an orgasm for the second time that night. Greg couldn’t resist as her pussy contracted against his cock, and he thrust in once more and held there, his fingers tight on her hips as he came, his cock jumping inside of her as he sprayed his semen deep within her.
Homer moved her when her boyfriend was done. Greg left the room, going to shower as he always did after sex. Homer lay down, and Dana went to suck him again, but he took her and pulled her atop him. She straddled him, rocking back and forth as he groped and pawed at her large breasts, her hard nipples pressing against his strong palms.
“Fuck,” he groaned as he came, and the second man that night let loose inside her. Afterwards, she climbed off of Homer’s wet cock and lay beside him. He kissed her, and then got up and dressed. He left, and Dana was fairly confident she wouldn’t see him again.
5
A month passed after the threesome, and then another, a
nd Greg remained, and their sex life was healthy. But he never invited anyone else into their bed. The relationship grew stronger, and got more serious, and Greg had begun dropping hints that Dana should leave her small apartment and move in with him. For some reason, she refused.
A part of it was her job. She still had never spoken with the mysterious buyer, the rich man instead communicating through a lawyer. She still wondered if it was Greg, and one night she decided to take matters into her own hands. She lay in bed that night, and he fucked her tits while she reached past him and used a vibrator herself. She came and then he did, spraying thick globs of semen across her neck and chin. He got up to shower, and asked her to join him, but she told him she wanted to take a bath afterward. He nodded and went to shower.
She got up as soon as she heard the water turn on down the hall, and found his cell phone still in the pocket of his pants, haphazardly strewn on the floor near the bottom of the bed. She strolled through texts but found nothing. And then she went through Greg’s contacts. It was there. The lawyer. There was the lawyer she had become so familiar with.
Dana wanted to confront Greg, but she had his splooge drying on her body, so she went and had a bath first. She stewed there, in the steamy water, and when she was done, she washed and dressed in a robe and stormed into Greg’s room.
“You have a lawyer’s number in your phone That’s the man who contacts me when Mr. White has something to say,” she said. Greg was lying on the bed, reading a book. He set it aside.
“I wanted to help you.”
Dana ground her teeth together. She had expected him to lie, and was glad he hadn’t, but she was still mad.
“I didn’t want that help from you,” she said.
“So what? Why does it matter? I have the money, I could help you.”
“You control me here. In bed. Not out there.”
“It’s not about control!” Greg said. “I just wanted to help.”
“If the business can’t make money, then it dies!”
“And then what would you do?” Greg asked.