Sadistic Billionaire (The Collection) Read online

  "What is it, Annie? What's wrong? Most women practically beg me to fuck them at this point."

  "You're cocky," Annie said.

  "Wouldn’t you be if you were me?" He said and grinned.

  He certainly had a point there, Annie thought.

  "I'm...I'm..." Annie started to say but the words would just not come out.

  "You're what? Tell me!" His booming voice finally gave her the courage to speak up.

  "I'm a virgin!" She blurted out quickly. "Alright? I'm a twenty-two year old virgin!"

  Troy's jaw looked like it had dropped to the floor.

  Suddenly Troy couldn't get away from Annie fast enough.

  "What's wrong?" Annie asked, confused by this turn of events.

  "You're a freaking virgin, that's what!" Troy said, looking mighty uncomfortable.

  "But you just came on to me!" Annie said. "You said you were ready to go. What's changed?"

  "I don't do virgins, Annie. Sorry. But it's just too much trouble."

  Now that Troy was saying no to her, Annie's feelings for Troy solidified themselves: she wanted him now more than ever.

  "Troy," she said after some careful thought. He had his back to her and she reluctantly put her arms around him. "I want you to be my first," she whispered in his ear.

  This time, Troy was the one escaping from her grasp.

  "Sorry, Annie, but I don't want that kind of responsibility. I think you should go and forget this ever happened. Maybe come talk to me when you've lost your v-card."

  Annie was furious as she walked back to her little run down car. Hot tears streamed down her face. Troy Ripley was a monster. First he wanted nothing but to get in her pants, and now he was the one rejecting her because she was a virgin? Maybe the world was right, maybe she was a freak after all. But what was so wrong for a girl to wait for the right guy?

  Obviously Troy was not that guy and she needed to put him out of her mind. If only she didn't work as his personal assistant and saw him five (sometimes more) days a week.

  She slammed her car door with more force than necessary and the whole thing almost came off its hinges.

  "Shit," Annie said, shocking even herself at her language. She looked back at the huge mansion behind her and scoffed. "You might be rich and good-looking and sexy and perfect, Troy Ripley, but you've never known love have you?" She asked out loud in the car.

  Just to make her night better it rain started to pour.

  "Just great," she said as she tried to turn her wipers on but to no avail. Of course they didn’t work.

  She jumped as she heard a loud knock on the passenger side window. Was she going to be mugged now, too?

  She tried to make out the person who did the knocking and was shocked when it was Troy Ripley out there in the pouring rain. She quickly unlocked her passenger door and he quickly entered the small vehicle.

  Even wet as a dog he looked absolutely gorgeous, which made it somehow worse.

  "What do you want?" Annie said coldly as she focused her gaze in front of herself. She dared not look at the gorgeous Troy Ripley for too long. Now that he had rejected her, she needed to reinforce the boundaries between them.

  "Look, I'm sorry I said those things. I'm a little messed up," he said calmly.

  "You can say that again," Annie shot right back. "I saw your little torture chamber."

  "It's not a tor..."

  "Call it what you will, it's still sick, Troy, Mr. Ripley, or whatever the hell you want to be called. I've had enough of you. I'll finish out the week and then I'm gone."

  Troy put his hand on her shoulder. "Don't do this, Annie. I like you. You've like not like any woman I've met before."

  "Why? Because I'm a virgin, and in your eyes that makes me some kind of freak?" Tears started streaming down Annie's face and she hated herself for it.

  "It's not that at all. It's just that I had a bad experience with a virgin once. It was when I was a teen. In fact it was both of ours first time."

  "What happened? She got pregnant and had to get an abortion?"

  "I wish, Annie. Don't you know how many times I've wished that that was what happened? I stay awake at night praying that she's still out there somewhere hating me. But no, that's not what happened. She's....I've never told anybody this..."

  Annie looked at Troy and he was looking down in his lap. She'd never seen him look so defeated. He was always confident and self-assured, but not right now.

  "What happened, Troy? What happened to her?" Annie asked at the edge of her seat.

  "We were just stupid kids, barely sixteen, and I didn't know. She died, Annie. She died in my arms right after we had sex."

  "What happened? How is that even possible?"

  "She was a hemophiliac. She bled to death. That's why I've never been with a virgin since. The memories are just too much. I know it's not rational."

  "It's not, but I do understand," Annie said and smiled gently. "But you don't have to worry about me. I've had plenty of cuts and scrapes throughout my life and I've never bled too much."

  "That’s good to hear," Troy said and wiped the tears from his beautiful blue eyes. I felt like his equal right then and there, but he changed just as suddenly. Once the tears were dry he was himself again.

  "You know where to find me if you want this to happen," he said and exited the car.

  Annie held on to the steering wheel a bit too tightly. She let it go and made up her mind.

  She exited the vehicle and ran after Troy Ripley. Either to make the worst mistake of her life, or the best.

  In silence she followed Troy down the basement steps and into that familiar room again.

  Troy stood in the center, fully clothed, and with a whip in hand.

  "Get on the bed," he said gruffly, a mischievous look in his piercing blue eyes.

  Annie did as she was told, all the while thinking about what the hell she had gotten herself into.

  "You've been a bad girl, Annie," Troy said with his booming deep voice that sent shivers of fear down Annie's back, and reverberations of desire everywhere else. "You saw me at my most vulnerable, and now you have to be punished."

  "What the hell is this, Troy?" Annie didn't sign up to be his S&M slave or whatever the hell this was. She just wanted her first time to be special.

  "No talking. Turn around and put your ass in the air."

  "But..."

  "No buts, Annie. This is my house, my rules. If you don't like it, you can get the hell out right now and you'll never see me again."

  Annie looked at the gorgeous and dangerous man, holding a whip in his hand and that crazed look in his eyes. She made him mad, that much was clear. He had revealed a side to her that few people, if any, ever saw, and that made him feel powerless. This was his way of trying to get that power back.

  At least that's what Annie could glean from having taken a Psych 101 once at a community college.

  She knew he was in pain, and she knew this was the only way he knew how to relieve it: by hurting another. Annie turned around on the soft cushioned bed shaped like a circle, and put her ass up in the air. She closed her eyes tightly and waited for the impact.

  She heard Troy swing the whip and the terrible whistling sound it made in the air made her cringe.

  Once it made contact with her ass, she knew she was in trouble.

  The pain was a lot worse than she thought.

  "Ow!" Annie cried out in pain as she clutched at the soft fabric beneath her. It seemed fitting that it was the color of dried blood.

  Troy came up behind her and breathed on her neck while patting her tender ass cheeks through her dress.

  "I can stop if you want me to, but you already know what will happen if you do. I should warn you, though; it's only going to get worse from here."

  Annie bit her lip so hard it drew blood. She hissed but she kept the tears at bay. "I’m a big girl, Troy, I can take it," she said defiantly.

  "You're a lot tougher than you seem, Annie. It's a nice surprise.
"

  He struck her again. And again. And again.

  Just when Annie thought he would never stop, he dropped the whip on the floor.

  "Go get yourself cleaned up. I'll show you to your room and we can continue this tomorrow."

  "But what about work? Don't I have to be at work tomorrow and you too?"

  "I'm the fucking boss, Annie. If I want to take a couple of days off to spend some private time with you, that’s what I'll do. Are you saying you'd rather work than play?"

  "No, no, sir, that's not it at all..."

  "I thought so."

  "But what about...you know?"

  Troy closed the distance between them like an expert predator getting closer to his prey. He held her chin in his big hand and Annie quivered, afraid of what he might do next.

  Then he lowered his hand until it reached the center of her dress. He pushed his fingers through the fabric of her dress until he reached her center.

  Annie moaned, surprising herself. She saw that the bulge in Troy's pants was getting bigger.

  "I see you're already ready to go," he said and smiled. Then he took his fingers away. "But you know what they say: good things come to those who wait."

  Annie's nipples were hard and her pussy was wetter than ever. She put her arms around herself and shivered. Her ass hurt like hell.

  "After you clean up, meet me in the dining room for some dinner. We'll discuss the fine details of our arrangement then."

  Annie followed Troy up the stairs. It seemed that most of the party had already left, which made her feel much better.

  Troy showed her to her room on the second floor.

  "There's a bathroom in there. Dinner in fifteen. Don't be late."

  "Or what?" Annie had the courage to ask.

  "Or we'll have to continue your punishment."

  Annie flinched at his words and went to "her" room to freshen up for this all-important dinner.

  He was sitting at the head of the table when she entered the huge dining room. The table could easily seat fifty people. But there were only two placemats there now. Troy's at the head of the table, and hers to his right. There was also a document on the table. Quite a thick document.

  Annie was in pain throughout the entire evening. She could barely sit still because of how much her ass hurt from the whipping. Thankfully, it only left deep red welts and no skin was broken, but it still hurt like hell. She didn't say anything about it to Troy, though, because she knew he would find a way to use it against her, or even delight in her pain. She didn't want to give him the satisfaction.

  After they ate in silence and the butler took everything away, Troy took the stack of papers in his hands and flipped them through.

  "Everything should be in order," he said, looking quite pleased with himself. He took a sip of his wine and handed her the thick document.

  She flipped through it and then looked at the top of the first page again: Written Agreement of Conduct Between one Troy Ripley and one Annie Devaroux.

  "What the hell is this?"

  "Exactly what it looks like, my sweet Annie," Troy said as he got up from the table.

  "If you don't sign it by tomorrow, you won't be getting any taste of this," he said as he grabbed his crotch, and the substantial rod residing there.

  Troy left her there, sitting alone at the huge dining table, looking at that impossible document, and trying to process what had just happened.

  What the hell have I gotten myself into? Annie asked herself, and not for the first time that evening.

  Hard At Play

  Annie took an ink pen that one of the servants had provided her with and tried to sign the dotted line, but just before she did, she stopped herself.

  What kind of man asks a woman to sign a contract before he becomes intimate with her? Was Troy Ripley, billionaire extraordinaire and one of the best looking men she'd ever seen, really someone she wanted to get that close to?

  She flipped through the contract again and tried to make sense of all the rules and regulations. She would not speak of their carnal activities to anyone. This she could agree with. It's not like she had any friends to talk to about it anyway. But the more she read, the more troubling the contract became. It appeared that Troy and she had to agree on a "safe word" in case things went "too far." How far did Troy want to take things? That was the question that Annie asked herself.

  She heard a knock on the door and almost jumped out of her skin. She left the document unsigned and went to answer the door.

  The butler who had served them dinner last night was there.

  "Mr. Ripley is expecting you in the library. He also said that you should bring the contract with you."

  And with that, the butler was gone.

  Annie had a strong urge to run, to get as far away from Troy as possible, but she knew she was too curious to let go just yet. Plus, there was something about him that attracted her. She couldn't explain it to herself, but when she was alone with him, it was as if the whole world disappeared.

  She held the unsigned contract in her hand when she entered the library. It actually was big enough to be considered a library and there were first editions on all the shelves. She was awed by the big space, but then she saw Troy standing in the corner with his back to her and a drink in hand and the vast space became much smaller.

  "I'm guessing you didn't sign it?" He said when she stopped in her tracks a few feet from where he was. He took a long sip of his drink and turned around. He was as gorgeous as ever, in a tight fitting suit that looked like it cost more than all her possessions combined.

  "You've guessed right. It just...doesn't feel right." Annie said and looked at the contract in her hand.

  Troy finished his drink and put the glass down by the fireplace.

  "What are some of your concerns? Perhaps we could amend the contract."

  "The whole S&M thing is just not something I'm into. Especially not for my first time. And I really don't want to find out how far you're willing to go. My ass is still sore from last night, and believe me the only one enjoying that was you."

  Troy came in closer to her and smelled her hair. Electricity sparked between them and Annie could barely breathe with him so close. Her heart was beating out of her chest.

  "It's not about how far I'm going, it's about how far you're willing to go," he whispered in her ear as he gently caressed her face with his hand. "That's why we have safe words. For your sake. And if you're so worried about it, I can make your first time as gentle as you want. But after that, all bets will be off."

  Annie stepped back from the man in front of her. The man that made her feel things she never thought possible and she took that ink pen and signed the contract.

  She handed Troy the contract and he took it and smiled. "You've made a wise choice, Annie," he said softly. Then he looked at her with those icy blue eyes. For a moment Annie thought she could see all his twisted desires in those eyes, but she shook the thought away.

  "What now?" Annie asked, not sure what to do with herself in a house this big.

  Troy smiled. "Now the fun starts."

  "Oh, God, oh my fucking God!" Annie screamed at the top of her lungs.

  Troy wore a twisted smile and drove his cock in her ass once more.

  "Good thing this room's sound proof, isn't it?" He whispered in her ear as he drove his big hard cock deep inside her ass.

  He pulled her hair with one hand as he fingered her pussy with the other.

  Annie was lost in a sea of ecstasy and pain: she had never felt anything like this before.

  Troy fucked her harder, and she screamed louder, which only made the sexy billionaire want to fuck her that much more.

  "You like my big dick in your tight hole, don't you, you dirty little whore?" he hissed as he drove himself deeper again. Now he was in balls deep, and she could hear the slapping of his ball sack as he thrust in and out. She moaned out wordlessly as this god of a man fucked her. She dared not utter the safe word, no matter how
painful it got: she didn't want him to stop, not ever.

  "Oh god," she screamed as he drove his fingers deep inside her wet pussy. "I want your cock inside my pussy," she moaned.

  "I bet you do, you dirty little slut," he said as he drove himself in harder. She came again and again on his fingers, while he too seemed close to climax. After a few more brutal thrusts, she finally felt his sweet hot cum bursting free deep inside her. He exited her abruptly and left her terribly empty. She remained with her ass in the air as he left her there. She was sore and wet: his perfect body not being as close to her as possible was his worst punishment yet.

  "Oh my god, Troy, that was amazing," she managed to get out between breaths. She looked behind her and saw him standing there, with his semi hard dick in his hands. It was so goddamn big, she wondered how her tight hole could have taken it. But now her other hole ached to have that beautiful dick inside it, and she wasn't going to be satisfied until it was.

  Once she realized that Troy wasn't going to make the next move, she did: she laid back on the soft cushions and spread her legs for him, giving him a perfect view of her wet pussy. She fingered herself as he watched.

  She saw his dick getting harder and that put a smile on her face.

  The smile on Troy's was gone, however. He walked, stark naked and gorgeous, to one of the walls and picked out a set of chains.

  Annie quivered in anticipation. He had promised her that her first time would be gentle, and this was anything but. If this was what Troy considered gentle, what would he consider rough?

  He took her hand and led her to another section of the basement she hadn’t seen before. There was a spot on the wall he led her to that was covered in soft material. There were several loops for the chains he was carrying in his other hands.

  He leaned down and gave her a passionate kiss which sent butterflies flying all inside her. She smiled because she thought he was being romantic, but with men like Troy Ripley, you could never be certain what they were thinking.