C. Charles Fenwick was 42 years old, wealthy beyond his needs, alone in the world. His given name is Chadwick. He cursed his parents for naming him, Chadwick Fenwick. What a stupid name. He went by Charles in the business world. His close associates called him Chad. They were associates; he really had no one he called a friend. Charles had been successful in business, he had a knack for it and a drive to succeed. He had a beautiful wife and a young son. Then ten years ago he lost them both in an auto accident. In his grief he shut himself off from the world, turning his mind completely to making money. He didn't care who may be shunted aside, stepped over, inconvenienced. He would succeed, spectacularly. Oh sure he had his physical needs. Those reappeared after two or three years. But he could never give himself over to anyone again. He couldn't expose his heart to the risk. So he had companions. No one he would call a girlfriend. His current companion was a 26 year old beauty. Large firm breasts, wide hips, dark hair, dark eyes. She could suck his cock like no other and ride him to exhaustion. She was hot and kinky and there for his needs. But he knew she enjoyed his money, while he enjoyed her body. She wasn't a whore or call girl, just a young woman enjoying some of the finer things in life. And C. Charles Fenwick did enjoy the finer things in life. Starting with his penthouse apartment. A suite of rooms overlooking the park. He employed a chef to prepare meals as needed and a housekeeper to make sure everything was in order.
Tonight he waited for his companion Bailey to arrive. While enjoying a glass of good wine he thought about something that had happened on his way home. He often walked home to enjoy good weather and had no trouble ignoring most people on the street, walking past them in his own world. Tonight though, just a couple blocks from his building he passed a young panhandler. A disheveled woman, wan, tired looking. As usual, he would have walked by, but she caught his eye. He looked again. Deep blue eyes, somewhere between hopeful and hopeless. He stopped, took out his wallet hoping he might have a dollar or two. He rarely carried cash, who did these days, but he found a twenty. It seemed a bit much. What was he thinking, he could light cigars with a twenty and never notice. He dropped it in her basket.
"Thank you sir." Her voice, tired, but pleasant. He looked at her again, then passed on.
Why was he thinking of her now? Maybe the novelty of the situation. Just another unfortunate. Maybe a druggie? Someone who lost in this game of life? The door buzzer. That would be Bailey. He forgot about the beggar as he let her in. She'd brought a friend. This was promising to be an interesting night.
"Hey Chad, this is my friend Kenzie. I brought her over to party with us tonight. Hope you don't mind?" Mind? Here was another hot young babe half his age. She had straight blond hair, brown eyes, a tight little ass and perky tits. She also had a perky personality and practically bounced into the apartment after her friend.
"Sure no problem. Welcome."
"See, I told ya Kenz. And look at this place, and the view!"
Kenzie looked around. "Wow." Then she looked at Charles. "Wow." Now this was a girl who knew how to ingratiate herself with her host.
"Wine ladies?"
"Yes!" "OK, thanks."
They settled on the sofa, one girl on either side of Charles. Bailey was already running her hand over his chest. Kenzie was still looking around, wondering how things would go.
"Chad, I missed you, it's been a few days."
"Sorry Bailey, work has been busy. But I do have time coming up. I thought we could go up to my lake house, spend some time on my boat?"
"Cool. Yes, just tell me when."
Materially driven people were so easy for Charles. Dangle a dinner, or a boat, or new earrings and their whole outlook changed. It was the same in business. Now Bailey was properly motivated. She slipped off her shirt, letting him see her bountiful breasts in the new red lace bra.
"Come on Kenz, show Chad what you've got." Kenzie needed no more encouragement. She too removed her shirt and quickly lost her bra. Two upturned B cup tits now awaited Charles' attention. He lifted Kenzie onto his lap and began sucking at one pointed nipple, and then the other.
"Why don't we take this inside?" He was definitely getting a piece of this hot new ass tonight. Oh sure he'd have plenty for Bailey too. He was in good shape for his age, but kept a stock of pills to ensure he performed like a guy their age. They moved to the king size bed down the hall. This was an extra room he used for these types of encounters. None of his visitors were allowed into his private bedroom.
Charles stripped and positioned himself against a pile of pillows. In addition to business acumen and wealth, he was also blessed with a fairly impressive cock. It was a good 7 inches, a good thickness too. If asked he told women it was over 8 inches. Who's measuring, and it usually excited them. His cock was hard and standing proudly. Kenzie again said, "Wow."
He almost said the same thing when Kenzie dropped her pants and thong. She was obviously a natural blond. Wispy light hairs collected on her mound above her cleanly shaved lips. Bailey was completely bald, but this was a nice change. He knew then what he wanted. He slid down a little on the bed.
"Bailey, I've got something here that needs your attention." Yes, it did, and she was just the cocksucker to take care of it.
"Kenzie, up here, I feel like I need to get better acquainted with that cute pussy of yours." Bailey got to work on his cock, sucking it into her mouth and expertly using her tongue to tease his full length. Kenzie scooted up on the bed and squatted over his face presenting her pussy to him. He pulled her down and prodded at her with his tongue. Then licking her slit and sucking at her clit to get her going. He savored her wetness, slipped two fingers into her tight cunt and fucked her that way as he licked up and down tasting her, inhaling her sweet tanginess. This was good. He liked a sweet young pussy in his face. He wasn't so worried about her getting a lot of pleasure, Chad just wanted that fresh newness. Bailey was busy servicing his cock and in a few minutes he'd fill her with his cum, but a nice new pussy to taste before filling it with his cock was Charles' idea of a good evening. Bailey would be back for boats and jewelry and nice dinners, but this might be a single shot at her friend. He knew how young women were. If he spent too much time on Kenzie, then no way Bailey brings her around again. Kenzie was now grinding on him. His fingers had found a good spot, she was rocking her hips rubbing her pussy on his face, his thin beard would be coated in her juice. Bailey was doing her best on his cock, but Chad was getting into this blond cunt more that he usually did. For him women were a release to be had as needed. He was never abusive or cruel, he just didn't have the time for romance. Nor the desire. It was a physical act, pleasurable certainly, but a satisfying of a need. Kenzie, began tensing and cumming, he pinched her pointy nipple and she went off, dripping her female cum. That was it. He needed this blond pussy, now.
"Move over Bailey." She sat back. She might be a little concerned. Was he disappointed in her, not satisfied? Charles flipped Kenzie over on to her knees. He positioned his cock at her pussy and drove it deep. She wasn't expecting his length AND girth and cried out.
"Sorry." He backed off and found the right depth, then held her slim hips and fucked her relentlessly, shaking her, her blond hair whipping back and forth as he drove his pulsing cock into her. Then reaching his peak he felt his whole body clench, a moment, and release. His hot cum coating her insides. When he'd emptied himself he sat back. He looked at Bailey.
"It would be a shame to let that go to waste. You were working for it anyway." Maybe that was a little mean. But he did get off on watching two women together and watching Bailey lick his cum from his latest conquest, her friend, that was too good to pass up. He'd have to have his office assistant pick up something nice for her. Bailey, looking a little dejected rolled her friend over onto her back and set to licking his cum as it dripped from Kenzie. He wasn't sure if Kenzie was into girl on girl but she seemed too spent to argue. Instead she said,
"Chad, you're so big. I've never felt one like that." He smiled at her. He knew she was partly trying to gain favor, but hey maybe she hadn't been with such a well endowed guy before. He wasn't worried that he'd just dumped his cum into her. A couple years ago he'd had himself fixed. He wasn't bringing any more kids into this shitty world. And he didn't want anyone trying to bribe or blackmail him. They could have his semen. But no one was getting any sperm. He was free to fuck who he wanted. He paid a very good doctor a lot of money for regular testing. Such is life.
It didn't seem that Kenzie really got off from Bailey's efforts but at least her pussy was clean. And watching them had kept his cock at half-mast. He liked it that way. Still longer than most guys and ready for action with little more effort. Bailey had finished with Kenzie and was now laying by him, rubbing her nails on his cock. He was going to have to fuck her tonight or she'd pout. He might soon need to move on from her. At some point you couldn't have them leading you around by your cock, making you want their pussy. There would be tears, there always was, then she'd be gone. He'd do without for a while, but eventually, when the need arose, he'd see a likely girl and it would start over. But for now, she was still amusing him, and she had hot friends. He'd give her a good fucking, assure her, then have some peace and quiet when they left.
He was soon stiff. Bailey got on top and rode his hard cock. She could take most of him, so that was nice. She told him how hot he was and how his huge cock filled her and excited her. She came twice, then worked him with her pussy until he filled her. She settled on him. Letting Kenzie know that he was hers. They left after a late dinner. He'd probably send something to Kenzie. He usually didn't the first time or so with a new girl. He wanted it plain that he wasn't buying them. But she was good. He liked that blond pussy of hers. Who knows, maybe she'd become his regular. Wouldn't that fuck with Bailey's head?
When they were gone he looked around the apartment. Mrs. Williams would grumble about cleaning up after one of his fuck sessions. But what did she expect? The apartment was spacious. A kitchen and dining room, large living room, his private bedroom, the fuck room and a smaller guest room. He didn't often have guests, but sometimes weather conditions or events in the city booked up the better hotels. He relaxed with a good Scotch, sated. It had been a good evening. But something nagged at him.
Days went by, his evenings a mix of work and events. As with most wealthy men he gave, generously he thought, to charities. It helped to assuage any guilt that could creep in from the wealth he enjoyed. Still, he passed by most people on the street without a thought. Then one evening walking home, on a different street, across from where he was, he saw her again. He stopped and looked to be sure. Yes, he was certain. He made his way across and stood by her. Had he been thinking about seeing her again when he had his assistant get change for him? She seemed to be wearing the same soiled clothes. Her hair needed a good washing but otherwise there was no distinct odor. She didn't smell like alcohol. He dropped a 50 in her basket.
"Bless you." She said reflexively, then seeing the 5-0 on the bill, looked up in shock. "Oh, you again. Thank you so much."
"Let me see your teeth." He'd asked before thinking.
"Oh, no sir. I don't suck cock, even for 50 dollars. If that's what you want you can have it back. I, I haven't sank to that yet. No sir."
C. Charles Fenwick looked down in surprise. She thought HE was going to buy a blow job?
"No, no, no young lady. I'm not soliciting. But, please, show me your teeth." She made a grimace, exposing healthy, if slightly grimy teeth. "No alcohol? No drugs?"
"No sir. Just down on my luck." He added another 20.
"Do you stay at a shelter?"
"With your kindness, I can. And get a good meal too. Bless you." Charles nodded, then moved on.
At his apartment, Mrs. Williams was grouching about cleaning up his extra room, as she called it. "I'm a proper Christian woman and to clean up after your debauchery, Mr. Fenwick. Well I'd rather not.
"Mrs. Williams, I'm a single man and I will entertain how and whom I choose. If you don't care to work for me, there are other apartments to clean in this city." She humphed and grumbled and gathered her supplies. Then she slapped a paper on his table.
"That is the bill for this week. And this will be my FINAL week. Thank you." She left.
Good riddance he thought. He'd find someone else. Maybe someone better to look at as they moved around the place. He was feeling needy again. Maybe time to call Bailey. Or, what was her friend's name? But he called Bailey. He was in a mood. Mrs. Williams had annoyed him. The vagrant girl nagged at him. Then there was the usual business concerns. He needed an outlet. Fortunately, Bailey was ready and willing to be that outlet. He supposed he'd have to take her to the lake. Then maybe move on.
Bailey showed up two hours later. She was dressed, as requested, like a slutty tramp. Ready to be used. Charles grabbed a handful of her hair, pulled her to him and kissed her hard on the mouth, using his other hand to roughly squeeze her tit. She moaned and looked at him.
"Does my strong man need his slut tonight? Are you going to use me? Fuck me good with your big cock."
"Shut up bitch. Just do what you're told." He drew her in again, cupped her mound and pushed into her with his finger. Her short skirt prevented him from entering her. She was not wearing underwear. "In the bedroom." He slapped her hard on the ass as she turned. She shook her ass at him all the way down the hall. MMM, he was thinking how he was going to use her tonight. When they got in the bedroom he had her strip, then pushed her back on the bed. "On your knees."
Charles wasn't often this wired up. They'd played rough before, and they'd had sex in a variety of ways, but he had a feeling she might be sore at the end of tonight. Oh well, she liked a bit of rough stuff and the thought of a weekend at the lake on his boat, first-class food and wine, and his big cock, would help make up for this evening. He wondered if she had doubts if this was all worth it. She took her position, at least he wasn't tying her up. He got up behind her. WHACK! 'Oh shit' WHACK! 'oh fuck' Her ass would be red. Charles looked at the handprints on her right ass cheek. Maybe she needed one on the left. WHACK! Damn, her ass was red. He grabbed her ass cheeks with both hands.
"OW FUCK, Chad."
"Shut up" WHACK! Now both cheeks were even. He held her and fed his cock into her. She took his length but winced each time he slammed into her ass. He fucked her hard, and deep, and fast. Then he spit on her asshole. She'd know what was coming.
"Oh god." Yes, his club was going up her ass. His cock was lubed from her pussy, then his finger invaded her ass.
"OOOOOOOOHHHH!" Whack!
He withdrew from her pussy and pushed his cock against her ass, pushing the head right in. Then he stopped.
"Oh, oh, oh." He caressed her cheeks, teasing her, letting her anticipate another smack. He lightly tapped her cheek, distracting Bailey, then, pushed.
"Oooooh fuck." He was in, but he had a ways to go. She bent her head and waited for Chad to fill her ass. And here it came, in, in, deeper, his hands on her sore ass cheeks. More pain from his hands than from his invasion. Her ass stretching. Then he was all the way in. A moment, then out, out until only an inch or two remained, then slam. All the way. And now it was on. He fucked her ass, and fucked her ass. Grunting with his exertions. A few light slaps on her ass as he took her deep. Finally he came into her. He pulled out.
"Get a wash cloth. Clean me good because it's going back in your mouth." She cleaned him, then sucked his cock. Then he fucked her, driving her sore ass into the bed with each thrust. When he at last came again he was satisfied. He looked over at Bailey. Young, attractive. Too experienced to be sweet.
"Should I suck you clean?" Now he felt a little bad. She'd had her uses for him tonight, but now he was relaxed.
"I'm sorry Bailey."
"No, no that's ok. You had a need.."
"Maybe a bit too far. Really, clear the weekend of the 15th. We'll relax, have fun. Sunbathe on the boat. I know some secluded spots."
"Thanks Chad. Do I need to get anything?" Chad leaned over and kissed her on the nose.
"Yes. Get a new swim suit. And something cute for dinner. Tell them to charge my account."
"OOh, yay. Ow." She moved on the bed.
"Maybe some lotion too." She smiled. Ah she was going to be a tough one to leave. Bailey stayed for awhile. He listened to her go on about her friends and work. It mostly bored him, but Charles figured he owed her some of his free time for putting up with his aggressiveness earlier. Finally she left and he relaxed. It was quiet. He had been able to release some of his annoyance with the world, taking it out on Bailey's ass. At least he hadn't taken out the whips and chains.
The next morning it was cooler. As he waited for his car he saw the young lady begging for change. He walked down and asked why she was out here in shorts and a light shirt. He'd given her cash just the other day.
"Yes, you were generous, but money doesn't last forever and I try to save some for harder days. I did have a full meal. I'm grateful to you for that." As his car pulled up Charles thought a moment.
"Will you come with me?"
"I told you sir, I don't have sex for money."
"Nothing like that. I'd like to..to help you. I want to ask a few questions."
"Can I bring my few things?"
"Yes. yes, we'll put them in the trunk of my car. I'm on my way to work downtown. Ben will drive and we can talk." She caught her breath. "Is something wrong? No one will harm you."
"No, it's ok. I'll go with you. I'm about at my wits end, I suppose I can take a chance."
"I promise, no one will harm you or treat you inappropriately."
"Men aren't always so kind."
"Yes I know." Charles had his driver open the trunk then gave him instructions to call his personal assistant at the office with a list of tasks. Ben looked uncertainly at the woman. He was thinking his boss could probably find someone a little cleaner if he needed some action. Charles waited until the woman was in the car, then went around and got in the other side. The woman looked at the interior of the luxury sedan, then at Charles.
"My name is Charles. What is your name?"
"Amy."
"Amy. Good. Now I want to ask you a few questions." She stared at him with her deep blue eyes. She nodded.
"Do you do drugs?"
"No."
"Do you drink excessively?"
"No. Some. Not a lot."
"Why are you on the street?" She began crying. He wanted to touch her to assure her, but decided he should stay on his side for now. Through sobs she tried to explain. Thrown out of her house. Abusive father. Teen pregnancy. Child's father left. Couldn't finish college. Couldn't find a job. No home, no credit, no job, no hope.
"You couldn't find anything? Surely...."
"Easy for you sir. When you have nice things, you keep nice things. When you have nothing. And I've tried saving every dollar I can get. So I can...so.."
"So you can do what?"
"Find my baby. They made me give him up. If it wasn't for my dream, I probably would have been selling myself. But I want to be a proper mother someday."
"Oh jeez. Your family abandoned you? You have no one to turn to?" She just shook her head then bowed it, sobbing.
The driver lowered the separation panel. "Ms. Penelope says everything will be ready."
"Thank you Ben."
"Amy, when we get to my office, I'd like you to go with my assistant Penelope. You may call her Penny. She will see that you have a hot shower, new clothes and a good meal."
"Why are you doing this?"
"If I said you reminded me of someone, can we leave it at that?" She sniffed away tears and nodded her head. They met Penny who looked over Charles' new, well she didn't know what. Penny was nothing if not super efficient. Charles never thought about bedding her, though his business associates often assumed he must be sampling such a tasty looking woman. But she was much more valuable to him as his assistant and they remained entirely professional. To the point where she was one of the few people who could call him out on some of his actions. She took him aside.
"Really Charles, what's going on here? Street urchins? Isn't that big boobed bimbo of yours enough?"
"Bailey isn't a bimbo. But no this is nothing like that at all. Please get her cleaned, clothed and fed. Talk to her, as a woman. She's still cautious with me. Oh and do you have a doctor she could see? Who knows how long she's been on the street or in shelters. And find out how old she is."
"Yes Charles." She looked uncertain.
Later that afternoon Penny buzzed Charles in his office and asked if he had a few minutes. He told her to come right in. She entered with a striking young woman behind her.
"Amy Henderson, C. Charles Fenwick." Amy looked around at the modern office. No old wood paneling and dark heavy chairs. Charles' office had large windows; it was light, airy, glass and metal. Charles showed the women to chairs across from his desk.
"Amy, you look very nice. How do you feel?"
"1000% better. Thank you both, but why am I here?"
"Because of fate I suppose. You were in the right place and caught my eye and well, I've never done this before. Oh sure I donate to various causes, but no not individually."
Penny spoke up. "Amy is 24. She has a high school diploma and has actually attended some college courses. She has no current regular source of income. Doctor Dowling says she has no apparent medical issues, pending bloodwork, no sign of drug use, nor sexual abuse. Somewhat malnourished, but now clean and healthy. What next boss?"
"I have an idea. Amy, can I trust you?"
"Yes. I don't steal or cheat. Well, maybe some days when I'm hungry I may take a piece of fruit from that stand on 57th."
"Understandable. But if you were well fed and had a safe place to sleep?"
"I'm an honest person, sir. I have my standards, despite how I've fallen." Charles looked over at Penny. Penny rocked her head, unsure of where this was going.
"Ok, a proposal." Amy stiffened. "No, your virtue is safe, though your ears may hear things." Penny rolled her eyes. "My housekeeper quit on me this week. I haven't found a replacement. Could you take care of my apartment? Maybe run some local errands for me? I have a spare room where you can live. I pay well." Penny looked on surprised.
"Charles, what about?"
"Yes, that's the other part."
Amy, "Other part?"
"Some evenings, I may entertain friends. Women. We will do as men and women do. You may hear us from your room. You are free to go out those nights if you choose, but hopefully you won't be offended cleaning up after us the next day. That's what bothered Mrs. Williams."
"I've cleaned up at the shelter. Would you really pay me? I don't really cook very well."
"Just cleaning and errands. I have someone who cooks. You'll be looking to go on a diet in no time."
"I, I don't know what to say? And I have no obligations, you know..."
Penny cut in, "Ms. Henderson, I know from personal experience that Charles keeps his business, all business. If he touches you I'll rip off his balls." Amy put her hand over her mouth.
"I suppose my answer is yes."
"Perfect. Penny, you have the rest of the afternoon off to take Amy shopping for clothes and anything else you feel she needs. I'd appreciate it if you'd accompany us back to my apartment after work so we can get Amy settled."
"Of course. Let's go Amy this can be fun."
"OH, I almost forgot. My things in the car. I, guess I don't need the clothes, but there's a small bag with personal items. Can I get them?"
"Yes, we'll be taking the car home later." And with that the women left Charles to his thoughts.
C. Charles Fenwick sat back in his chair, his hands behind his head. Just what was he doing? A tear caught the side of his nose, ran down to his lip. Was he getting soft? No. It was something more than that. But what?
Charles, Penny and Amy rode back to his apartment after Amy checked that her bag was there. She clutched it to herself as they rode. This time she was clean, comfortably dressed and had hopes. And fears. She was taking a chance. She'd be living in an apartment with a single man. A very powerful, rich man. If this was all some ruse to use and abuse her, who would believe the tramp when she was found back on the street. The money spent on her so far was a pittance to Charles. But it was time to take a chance. If worst came to worst she'd let him have his way and move on. Lesson learned. She looked over at him. Serious, restrained, seldom smiling.
They arrived at his apartment building. Amy took note that he used a key and pressed the P floor at the top. They were quickly whisked to the top of the building. The elevator opened into a small lobby with only one door available to them. Charles opened the door and allowed Amy and Penny to enter. Amy looked around at luxury she could only imagine. To call it an apartment was the understatement of the year. High ceilings, wide open windows looking out over Central Park, all light colors, shiny, new, modern.
"Welcome to my home Amy. I hope you will be comfortable here. Let me show you around." They walked into the living area, comfortable furniture, a huge TV on the wall, a bar, and room to entertain. The shiny modern kitchen, with all the appliances Charles' chef needed to prepare meals when requested. "The kitchen is yours to use. I'll coordinate with you if Henri has put aside anything for a special occasion. Otherwise feel free to make yourself anything. You will not be required to cook for me. Keeping all of this spotless will be work enough." They walked past the dining room, hall bathroom, then stopped at a large bedroom. A king size bed and single dresser were the only furniture. "This is, well to be frank, where I entertain women friends. They rarely stay over, so you can check this room in the morning to see if the sheets need cleaning and anything needs to be put away. They would go in that dresser."
"The whips and chains", Penny added. Amy's eyes opened wide. A hand came to her face.
Charles, "Yes, or dildos, paddles, strap-ons, all manner of sex toys. Some girls like to be spanked, so you may hear cries. No one is actually injured. But you may find some items that need to go back in the dresser. Will that be a problem?"
"No, your personal life is to be no concern of mine."
"Good. Speaking of which, the closed room at the end is my personal bedroom. It's to stay that way."
"Yes sir."
"Oh and please, not sir. It makes you sound like an old English butler. Charles will do."
"Yes, of course."
"Good, now let's go back through the living room." On the far side of the living room was one more room. It wasn't as large as the other rooms, but it was spacious enough and had the same spectacular view as the living room. "This is your room. You may decorate or arrange things to please yourself. I will never enter without your permission. You have a private bathroom through that door. Is that agreeable?"
"Yes. It's so nice. And the view."
"Tonight you relax, make yourself at home. Tomorrow you can start by giving the place a light going over. Familiarize yourself with everything. You may work whatever hours you choose while I'm away during the day. As long as the place is spotless, it's no matter to me how long it takes. Is there anything else you need?"
Amy put her head down. "You've been so kind, but I was wondering. And you could take it from my salary to repay, but..."
"Say it, don't be shy. As you see my best people are straightforward." He nodded towards Penny.
"Well, I would like to get a laptop or computer of some kind. I would spend my free time taking college courses. I still have some dreams and things I must do."
"Of course! Penny, note that. We'll get you set up in no time. Perhaps a desk in here to work at?" Charles almost seemed to smile. His own perceptions and any verification that they were correct pleased him. "I knew there was something to you, yes I always support a person bettering themselves. The wifi here is excellent. But don't spend all day every day inside. Now you can walk the city with confidence. Shop, visit museums, take in the sites. I'll give you a key. Come and go as you please."
Amy looked embarrassed. In a day her life had changed. But would Charles understand her biggest dream? That could wait.
Charles proposed a toast to his newest employee. Amy sipped at a vintage she could have never tasted before. "Drink up Amy. A little wine in moderation is no problem. As long as you're not emptying my bottles during the day."
Amy smiled. "No I don't drink much. It was a waste of money. And my father drank a lot." Her smile vanished.
Amy went into her room to put away her few clothes. Charles talked to Penny on her way out.
"Do you see anything here that concerns you?"
"Other than that a cute young lady will be living in your apartment? It will be a temptation. Sure today she's still that bedraggled woman you found in the street. But I was with her clothes shopping. She's....got potential. Don't get ideas. Aside from that, no, I think she'll work hard. I think she wants to please you and if one of her first thoughts is education that's a good sign. Let her breathe Charles. This is a lot, suddenly. With your permission, I would like to mentor her. Meet with her every two weeks or so, help her make good decisions."
"Good idea Penny. Very good. I'm happy that you're on board. Now I have a list of items here. Please contact James tomorrow and have him do some research." James Fischer was Charles' attorney. He also did any digging Charles needed. Whether dirt on competitors or information required for the business.
"Certainly." Penny left and Charles was alone with Amy. Not exactly with her, but in the same home. He went down to his suite to shower and then sleep. Amy sat on her new bed, in new pajamas, staring out at the park. She lay back and had her best night's sleep in ages.
The work was not difficult at all. Sure there was a lot of furniture and kitchen appliances that showed every fingerprint, but Amy found that she could get through the whole place in a couple of hours. Two days after she moved in a tech person from Charles' office showed up and set up her new laptop. They'd also sent over a desk and a printer. She spent the afternoon getting reacquainted with the world. There was a lot more out there than what she'd gleaned from discarded newspapers. Penny called to set-up a meeting and to propose what she had discussed with Charles. Amy was more than happy to have a successful woman to guide her. She'd seek her advice on where best to take online courses.
Charles was in his office when James arrived with some information. He scanned the documents. Amy Henderson, honors student, cheerleader, college dropout, never married, one child, removed by DSS, then nothing. He looked up at James,
"Anything else?"
"Not yet Charles. I'm working on it. These records are not as public. But I'll find them."
"Good."
James left and Charles was satisfied for the moment. Now he needed other satisfaction. He called Bailey. Amy was cleaning up after dinner when the buzzer alerted them to a visitor. Charles looked at Amy.
"Please finish up here, then stay in your room or go out. I have, company."
"Yes, Charles."
Charles opened the door to Bailey. She was dressed in a more reserved shirt and jeans. It seemed Charles was looking for a more relaxed evening. She looked over his shoulder and saw the young woman, dressed not all that differently to her.
"Who's that? You didn't mention having anyone else. I could have brought Kenzie."
"That's Amy. She's my new housekeeper. She will not be joining us." Amy made her way back to her room.
"Nice ass. You doing her too? Am I not enough for you? Are you getting tired of me Chad?" Already she was getting that pouty look.
"No Bailey, Amy works for me, but nothing like that. Stop being so needy."
Amy had her door closed, but she couldn't help but hear them. Apparently Bailey couldn't wait to get down the hall to show her dedication to Charles. Certain things came through the door.
"Then let me suck your big cock Chad. That's it, mmm your big fat cock, all mine."
Charles knew what this was about. Bailey needed Amy to hear. To know that she was Charles' girl. To set limits.
"Give me your cum Chad, down my throat. Ooh, so big,"
Amy tried blocking it out. She went into her bathroom to change. When she'd removed her clothes she looked at herself in the mirror. The girl had said she had a nice ass. She turned, maybe. She certainly didn't have the big tits Charles' girl was showing off with her tight shirt. Amy's had plumped up a bit during pregnancy, but a couple years of limited diet had her back to her original size. She looked at them, smallish, upturned, dark nipples. She was still mostly skin and bones, but she'd be able to fill out a little with a good diet. There was so much food for her to choose from. And full healthy dinners cooked by an expert. From the other room came new sounds, Amy knew what was going on. She returned to her bedroom, laid across her bed, naked. She could hear the sounds of sex through the door.
"Oh fuck Chad, oh fuck, yes. Give me that cock, so big, fuck me hard."
And groans, and grunts and more cursing. Amy felt a wetness between her legs. She hadn't had time, or desire to think about sex while on the streets. She'd spent more time avoiding advances. Now she could hear Charles and his girl Bailey fucking in the living room. Bailey making sure she let Amy know she was receiving what she wanted and was entitled to. Charles was hers and Amy better get no ideas. Amy placed her hand on her mound, found her clit, rub her fingers along her pussy spreading her wetness, her hips raising to meet her hand. She circled her clit, reminding herself of long lost feelings, letting go moans of her own.
Chad did give Bailey what was hers, his 7 inches, and nothing more. He grunted as he plowed her pussy. Let her moan and carry on. He'd fill her soon enough. Let her finish her show.
Amy circled, slid her finger down, found her wet opening. She teased herself, cried out as she was reminded of past pleasures.
Bailey heard Amy as Chad slammed into her. The bitch was getting off listening to them. "FUCK me Chad. HARD. FUCK me."
Amy felt it building inside. Now she pressed her hand onto her clit rubbing directly on it. Faster, feeling a wave coming, she arched her back, her toes curled, then it hit her. For the first time in years, oh so good. "OOOOOOOOOOOhhhhhhhhhh" Then she relaxed, breathing deeply. She fell asleep. Satisfied.
Charles was finally there. He released his cum into Bailey. When he'd done he pulled out. "Let's go into the bedroom." Bailey stood up. Before she covered herself she let some of their combined fluids drip on the floor. Let the little bitch have something to clean. In the bedroom, Bailey fucked and sucked Chad until he was done. She made sure the bedsheets would need a good cleaning.
The next morning Amy waited until Charles left for work. She thought it might be awkward to see him, or to start cleaning up after his sex while he was there. First she got down and cleaned the floor of what she supposed was his semen. The girl had mentioned his 'big cock' multiple times. Why was she thinking about this? Amy HAD still had a bit of a tingle between her legs this morning. She resisted pleasuring herself as Charles would likely hear her. Maybe this afternoon after cleaning she'd treat herself. That changed when she got to the fun room. As expected the sheets needed to be changed. Out of curiosity she looked in the drawers. There were all manner of sex toys, some of which she could only imagine their uses. However, one object she knew how to use. A large black dildo, flexible, thick and long. Amy thought for only a moment before lying back on the bed, spreading her legs wide and beginning to rub the tip of the rubbery cock over her pussy. She was soon wet and able to insert the tip. Oh shit, it had been so long. Back in high school she had fucked a few guys, some were good, some not so good. She'd never had one this size and she wondered how close it was to Charles' 'huge cock'. The thoughts of a real cock so big, throbbing between her legs caused Amy to become more wet, to allow the dildo to stretch her and go further than her fingers reached. She found a good depth and began fucking herself with the dildo while circling her clit with her fingers. She was soon moaning in pleasure and happy she had the house to herself. When she was almost there she pushed the dildo in further and vigorously rub her clit setting off a powerful orgasm that sent a jolt to her pussy. Amy came down and relaxed a bit before cleaning up after herself. By the time Charles came home the apartment looked good as new.
Charles looked around. Satisfied, he paused a moment, then, "Apologies for last night. Bailey seemed to feel the need to announce herself. We'll try to keep our activities down the hall."
"That's ok. It's your home, you may entertain however you want. No offense taken."
He gave a tight-lipped smile. "You're no Mrs. Williams." Amy bowed her head at his little joke.
Amy soon took time in the afternoon to meet with Penny at a coffee shop down near the office. Penny turned over an envelope and another larger folder.
"Your first pay stub. In the folder, you will find information on your new bank account, a debit card and some forms to sign. We took the liberty of depositing your pay to open the account. Your future payments will be direct deposited every other week."
Amy opened the envelope. She looked at the pay stub. Then at Penny. "Surely there has been a mistake. I'm a housekeeper who already gets room and board. This is far too much."
"Honestly. Yes it is. But Charles is absurdly wealthy, has no family and pays well for work well done. I make far more than a personal assistant normally would. It's his way. Reward him by bettering yourself. Someday maybe I'll tell you more about him. More than what you can find on the internet?"
Amy blushed. Yes, of course, she had looked up C. Charles Fenwick.
"You're no fool. Of course, you researched. I'd expect nothing less. Come back to the office with me. We'll go over the papers, let you sign some bank documents and make sure you can use the bank app. Oh, you don't have a phone do you?"
"No."
"OK, we'll take care of that. Charles may need to contact you when he's not home to pick up something for him at a store. Or some other errand. I'm forever getting calls."
"Oh, you may need to show me how the newer phones work."
"Sure, we'll add that to our things to do. Also, have you given more thought to school? You can afford to signup now."
They went back to the office and worked on several things. Amy was happy to be getting her life in order. She'd be able to save money too.
The next weekend was the 15th. Bailey showed up with her bags, far more than she'd need for three nights, given that she'd be naked half the time. On his boat at the lake house, Charles allowed sunbathing, even nude in secluded spots, during the days, but expected everyone to dress appropriately for dinner and evening events. They would go out onto the lake in the morning and not return to the house until late evening. There was room for people to take a nap, or other activities, then change for semi-formal dinner. Being there as Chad's girl made Bailey glow. Watching the thin young woman prancing around his apartment in a t-shirt and shorts "cleaning" did not make her happy. She knew Chad must be fucking her.
When they'd left, Amy was relieved. The tension in the room with Bailey was obvious. The girl hated her. Was jealous of her. Though Amy was a few years younger, Bailey seemed much more immature. Having things handed to you can do that. But what about her? She was being handed things every day. Amy tried putting it out of her mind. She basically had a free weekend. A spectacular NY penthouse apartment to herself and money in the bank. Instead she was soon back on the internet. Searching.
Charles did like getting away for a few days. He worked a lot, but unlike some he did enjoy a little leisure time. Bailey was a fine companion. She liked dressing up, but she also didn't mind being nude in front of people. So daytime she could be found at the bow of the boat sunning herself, unconcerned about the prying eyes of other guests. Charles usually invited a couple of business associates most of them a bit older who managed to show up with someone decidedly younger who was NOT their wife. His only rule was, no one illegal. He wasn't getting himself caught in that kind of scandal. If someone got caught by his wife with a 20 something gold digger, well that wasn't his problem. At the moment the three young ladies were splashing in the water, their tight young bodies on display. The men enjoyed the view, good scotch, and a better cigar.
Bailey dressed for dinner in a slinky little black dress that would be so easy to slip off later. There was plenty of her bountiful boobs on display. She had competition as everyone seemed to enjoy a well-endowed companion. Bailey looked them over. At least hers were real. Henri had prepared a delicious meal, his assistant serving to the guests with the appropriate wine from Charles' personal cellar. After dinner and lounging under the stars the boat returned to dock. To call this a lake house was absurd. While it kept the wood and rustic illusion, it was all luxury. Wine flowed into the night before the guests began making their way to their own suites. When Charles and Bailey got to their room she made to slide her dress off.
"Leave it on. You look hot," He pulled her to him. Kissed her on the neck, then on the exposed swell of her breasts, his hands clutching at her ass through the dress. Sliding his hands down, then up underneath he pulled down her tiny thong and waited for her to step out of it. Lifting her he carried Bailey to the bed and set her down on the edge. Charles unfastened his pants and freed his throbbing cock. With his pants pooled around his feet he leaned into Bailey and impaled her with his firm prick. While feeding it into her over and over his hands roamed the silky material of her dress, feeling her young body rocking and undulating under him. He squeezed her large tits and pinched her nipples, rocking the bed as he pushed his cock deep. Bailey reacted, humping her hips up to encourage him, to allow him to reach her deepest parts.
"Oh fuck Chad. Fuck me, fill my cunt. I'm your fucking whore. Fuck me. Use my cunt. OH, OH. YES. You're the best. I'm your bitch whore. I live for your cock. I need your cum. Fill my cunt."
Fill her he did. He'd built up a good bit watching the girls all day, then teasing him in this dress all night. She locked her legs around him as he deposited a large load in the far reaches of her vagina. Her cunt as she was calling it. Dirty talk was good. She WAS a good fuck. And tonight a treat for her. She could sleep with him. He expected she'd suck his hard cock in the morning. It was worth it. Now he let her remove the dress, then clean up. Then she could get that sexy body up against him for the night.
Knowing they would be home Tuesday Amy spent all day Monday going over everything twice. When she'd finished, she happened to notice the closed door at the end of the hall. Surely that room needed cleaning too. But he said it was private. Amy walked to the door. If it's locked then she'd go back inside. She turned the door knob. It opened. OK, she'd take a look. If there was anything valuable sitting around she'd close the door and leave. There was nothing obvious. A king size bed. Standard furniture. Maybe even a little old-fashioned compared to the rest of the apartment. Curious about the sparseness of the room Amy carefully walked around the furniture. She dared not open anything and even now felt she was betraying a trust. Then she noticed the only item in the room. A photo on the nightstand. Curiosity got the better of her and she picked it up. When she looked at it, she staggered back, hit her legs on the bed and dropped the frame. The glass shattered sending shards across the wood floor.
"oh fuck oh fuck oh fuck." Trembling she picked up the frame. It was a photo of a young woman and she supposed, her son. But it was when she had looked at the woman that Amy became woozy. The young woman had the deepest blue eyes. The face was different, but it was like staring into her own eyes in a mirror. She managed to place the frame back on the nightstand. Then spent the next hour ensuring that she'd found and cleaned up every single speck of glass. But what had she done? Would he fire her? Kick her back out onto the street? She didn't know what to do. So she called Penny to explain what had happened. Penny suggested they meet immediately. That evening.
"Amy, I can't stress how serious this is. Charles expects and demands that people follow instructions. Right or wrong he feels that he knows what's best for him and his business. Someone going off course threatens him. I can't honestly say that this won't be grounds for dismissal. It's that serious. You've betrayed his trust. There's no greater sin when it comes to Charles."
Amy sobbed. Her eyes were already red from doing the same at the apartment.
"Don't think tears and pity will move him. He's got no time for people playing games. What I suggest is that you immediately confess. Admit your wrongdoing, and place yourself at his mercy. But first, let me tell you a few things."
Penny explained about Charles' earlier life. His wife Beth and son Charlie from the photo. Charles was a different man then. Sure he was successful, but he was a devoted father and husband. He always made time for his family. He had everything. Until the accident. Beth was driving up near their home in Westchester. They were hit by a truck on a blind curve. He was beyond devastated and only survived by diving 24/7 into his business. He had no time for anyone else. It's been ten years. "I started with the company seven years ago. What you see now is ten years of chipping at the hard shell that had formed on him. You notice that there are no photos around the other rooms. None in his office. Just that one by his bed."
Around noon on Tuesday the door to the apartment opened. Charles and Bailey came in. Amy was sitting on the sofa her eyes red again, crushing a napkin in her hand.
"What's the matter Amy?" All in a rush Amy explained about cleaning and checking his room and seeing the photo and dropping it and she was so sorry and never again.
"Stop." Charles was visibly angry. He paced. He clenched his fists.
"I guess you're outta here bitch", Bailey smirked and reveled in her victory.
"Bailey shut the fuck up. Why don't you just get the fuck out."
"What did I do? I never went in there. The stupid HOUSEKEEPER can't follow rules."
"GET THE FUCK OUT. And don't call me." Now Bailey started crying. She picked up her bags and left. Slamming the door behind her.
"Fucking cunt." Amy hadn't heard Charles like this. She wasn't sure which of them was the 'fucking cunt'. He was angry. Would he hit her? He paced, flexing his fingers. Pounding a fist into his leg. He grabbed a chair and placed it right in front of Amy.
"Look at me." She looked. Then shifted her eyes away. Her lips trembled.
"Don't hit me please. I'll leave if you want. I meant no harm but I betrayed you."
"Look me in the eyes." She did. With every effort, she held his gaze.
"I'm sorry." He looked and looked. Then she saw a tear in his eye.
"I imagine now you know why I helped you?" She shook her head up and down. "You have her eyes. I've never seen those eyes before or since. When you look at me it's like she's here again for a moment. I'll get a new frame. You may add cleaning my bedroom to your chores. He held her head between his hands. And.."
"And?"
"This is a foolish man talking. No obligation. Never ever is the appropriate answer. You owe me nothing because you've already given me so much. But IF, you ever want to join me in there, I will forego every other woman. Absolutely No obligation. And I say that before I show you this."
Charles got up and went to his briefcase. He'd received information he'd printed out at the lake house. He returned to his seat.
"James has been doing research. I suppose it was the same you've been attempting. But he has, uh, more assets to use. We've found your son. He's in a foster home on Long Island. I've had my people contact social services. It could take time. They need to check your situation, but I can bring certain pressure to the case."
Amy sat back. Fresh tears welled in her eyes. Her son? Her Benji? "Really?"
"Benjamin Henderson aka Benjamin Rotello, commonly goes by Benji. Age 6?"
"Yes. Yes. His father is Rotello. A useless bastard. Drink, drugs. Liar. But yes, Benji's father."
My people have done some research. He seems to be with a competent family. Well treated. But you are now gainfully employed by one of the more successful men in this city. Penny and I can vouch for your change in position. We have doctors reports to show you're not an addict. Almost certain your son will be returned to you.
"Oh my god." Without thinking Amy hugged Charles. Harder than she'd ever hugged a person. He was caught off guard, hesitated, then wrapped his arms around her. She felt wonderful. But he needed to stop.
"OK, ok. We still have work to do in this regard. As I said, it could take awhile."
"Yes. Ok. Um. Why this, after I messed up? I thought you would be furious."
"I was. For a moment. But you meant no harm. But really, you do need to learn the difference between suggestions and orders. I'll have Penny discuss this with you."
"Understood. Now may I go to my room? I have so much to think about."
"Yes, the place looks immaculate. You are very good at your job."
Amy had her regular Wednesday afternoon meeting with Penny. She enjoyed dressing in a business appropriate outfit and meeting at the office. They worked on cleaning up any holes in Amy's history, looking for anything that could come up when the went before a judge. But she had no record. Had been successful in school when she had a chance. Had now enrolled in online courses towards a degree. She was the perfect example of a good person who had had everything turn against her for awhile.
"Next week we meet with DSS and sometime after that we go before a judge."
"Will Charles be there with me?"
"No, we've agreed that it would be better to have a woman, me, accompany you. We want to avoid even the appearance that you're a kept woman, to use an old expression."
"Oh, but I don't..."
"Yes I know. But they don't." Amy shook her head. Penny continued, "So you got through your ordeal with Charles?"
"He was very understanding. Kind even. So strange that a chance happenstance should make such a difference."
"He's fond of you. And woman to woman, maybe a little more. And I've seen photos of his wife. He keeps some in his desk and insists that his closest associates see them to understand him. You don't really look like her, but he sees something."
"It's the eyes. When I looked at the photo I was shocked. Like looking into a mirror." Penny looked at Amy.
"I suppose so. Maybe it was the photo."
"No, when he looked at me. First on the street, then yesterday. Yesterday, when he should have been angry. He melted just a bit."
"Be careful. Know what you want. If he falls for you completely, who knows what that means?"
The DSS meeting was strenuous. Although she was well dressed and clean, to sit there and listen to your life being laid out. All your dirty laundry. Your failure as a mother to provide. Your failure to mate with a useful man. Your failure to follow basic sexual precautions. Her representative, an attorney assigned by Charles pointed out that her sins were simply the mistakes of a seventeen-year-old girl, who then didn't have the support system to help her. Rather than abandoning her child, she had tried and admittedly failed, to provide. Now a fortunate chain of events has put her in a position to be the loving mother she's always wanted to be. The officer asked what assurance there was that after having her child returned Amy wouldn't find herself without employment and again on the street.
Penny spoke up. "If I may. We are prepared to offer Amy Henderson a five year contract to guarantee continued employment. Furthermore, on completion of her college degree there is a standing offer for employment at our corporate office. Even if she were to leave for some reason she would be able to support her son."
"Very generous. If I may get personal. Is there some other arrangement in this deal?"
Amy began to answer and was prepared to show how offended she was when Penny put a hand on her arm and again took over.
"I understand your question. Let me state, on my good name, that even when living on the street, being offered $50 for a meal, she stated in no uncertain terms that she would not sell herself. There is no quid pro quo. C. Charles Fenwick makes these offers with no expectation of any favors, sexual or otherwise. Amy Henderson is free to allow her heart to decide what she does with her future."
Amy opened her mouth and looked at Penny. Then covered her blushing face.
The DSS officers retired to another room to discuss the case. When they returned they informed Amy that they were satisfied and would recommend the return of Benjamin Henderson to his mother. Amy broke down in tears and expressed her gratitude. There were still more steps, but Penny had told Amy that this was actually very much a short cut. No doubt from Charles' influence.
Over the next few weeks, Amy fretted, concerned that something could go wrong. But other things had changed. She noticed, without anything being said, that Charles hadn't had any women over. Apparently, Bailey was in his past. She lay in her bed. Wondering. Wondering if she was making a fool of herself. Wondering if she had the necessary experience. Wondering what it would be like. She assured herself that she wasn't selling herself. She wasn't giving her body to get her son back. She wasn't reneging on self promises to regain her self respect. But she'd been lucky. A twist of fate and in a virtual instant her fortunes had changed. She got up from her bed wearing just a light gown. Hesitantly she walked down the hall, paused and with a deep breath knocked lightly.
"Yes?"
"May I come in?"
"Yes, come in." Amy opened the door. Charles was reclining in his bed reading. He put the book aside. "What is it?"
"Charles..", she looked down. The moment of truth, "will you have me?" Charles smiled. Not a smile of triumph, but of happiness.
He pulled the sheet aside still hiding his body. "Yes, Amy. If you'll have me."
"And no other women?"
"We'll convert the other room into a play room. Games, a pool table, whatever Benji likes."
"And Benji?"
"He'll have your current room. And the finest education. All the opportunities that were taken from you."
"And all I have to do is.."
"Love me. I haven't been loved in ten years. You've cracked the shell. Release me." Amy slid the straps off of her shoulders. She let the gown slip from her. She stood nude in front of a man for the first time in years. In many ways the first real man. Charles looked at Amy. Still mostly skin and bones. She'd added a few pounds but needed more to suit her frame. He'd had enough of the voluptuous girls in it for the fun and money. He could have nearly any type girl her wanted. But he wanted to be with the skinny young woman who had endured so much. The one with the deep blue eyes that melted his hard exterior.
Amy walked to the bed. She slid in alongside Charles. He held her, she moved against him. She tentatively touched his chest, put her head against his shoulder. She wasn't quite sure what to do next. What did he expect?
"You're the first woman to share this bed with me. We can just sleep tonight if that works for you."
"I'd like that Charles."
"You can call me Chad now." Amy propped herself on her elbow and looked at him. Graying at the temples, worry lines, that two days needing a shave look.
"I like Charles better, if that's ok."
"It's perfect. Only my very best friends know enough to call me Charles."
"Am I one of your best friends?"
"The best." Amy kissed him on the mouth. More than a peck, but not exactly pass
