Gambling Debt Nobody messed with Bobby. That's the first thing you have to understand. Nobody. Bobby didn't seem to do anything for a living, but he was always in the money pretty good, and his house was a grand place, out in the country a bit, and on a lot of land. People who messed with Bobby had accidents. It was widely considered to be unlucky to get on Bobby's bad side. That was Jim's problem. He owed Bobby 15 Gs, and Bobby wanted his money. Jim didn't have it. That particular Wednesday afternoon, Jim showed up at Bobby's house to try to settle up. Now, Jim is a nobody kind of guy. You know the type, always about to make the big score. He is a medium sized guy of maybe 25 years or so, with an ugly kisser and a whiney voice. His sister Annie was with him, just to get out of the house. He had called ahead. You just don't walk in on Bobby. After all, he might be busy. Bobby had told him to park around back, and he met them at the door. The back patio door led into his rec room. Bobby was all business. "OK, you got my money?" Jim started his usual whining song and dance, but Bobby cut him off. "Did you come all the way out here to tell me you're still broke? I knew that. I keep up with things. I was hoping you would at least have come up with an entertaining excuse. I'm losing my patience with you, Jim." Bobby was talking so low Jim could barely hear him. Jim had heard that when Bobby talked low like that, it was bad. Real bad. Then he had a thought. Maybe Bobby would gamble for it. "Look, Bobby, I don't have the money, but how about we shoot pool for it. You have a nice table right here. What do you say?" Bobby just shook his head. "That would be great for you, but what if I win? You can't even pay me the 15. How would you come up with more? You don't have anything to bet with." Jim knew he had to think of something. "OK, how about Annie? If I lose, you get Annie. For an hour." Annie sputtered, "No way! You can't gamble with me! You don't own me!" Bobby just laughed. "Even if your little sis agreed, what makes you think an hour with her is worth 15 Gs? I might go 50 bucks." Jim grabbed Annie and pulled her aside. She kept repeating, "No way!" He was practically crying. "Look, sis, I can beat him easy. You know how good I am. I'm going to get killed if you don't help. Please, Annie." Well, it took some time, but she finally agreed. When Annie told Jim she'd do it, Bobby took a better look at her. She was 5'5" tall, light brown hair, and maybe 115 pounds. She was cute from what he could see, which wasn't much with the bulky sweatshirt she was wearing. Bobby thought and said, "Here's what I'll do. I might as well play, since you don't have the 15 anyway. We'll shoot straight pool, one rack, and if you win you are square with me. If I win, I get Annie for an hour for every ball I win by, and you still owe the 15." Jim didn't think he had much choice, and convinced Annie to agree, so Bobby got out a video camera and recorded Jim and Annie agreeing. They lagged for the break, and Bobby won, so he broke the rack. He didn't play safe, he just blasted them. Nothing dropped. Jim made five and then missed an easy bank into the side. Bobby cleared the table. "Well, good game, Jim. Ten to five, so I guess I win by five. It's 3:30 now, so Annie is mine until 8:30." He turned to Annie. "Ok, doll, strip." Annie looked stunned. "W w what?" "It's not a tough thing to understand, honey. I own you for the next five hours, so strip off your clothes. I want to see what I won. Now!" Annie looked at her brother, but he just looked away, so she stood up and slowly removed her clothes. She was sobbing the whole time. When she was naked, Bobby told her to stand with her feet separated a bit and clasp her hands behind her back. Annie was still crying and looking at her brother for help. Now that she was stripped, Bobby could see she was very nicely formed. Jim was trying to think what to do. He finally said, "How about another game. Give me a chance to win her back." Jim knew he would have won if he hadn't missed an easy shot. "OK," Bobby answered, "but if we play again, here's the deal. If you win, you take off an hour for every ball you win by, and if you win by more than five, you're in the clear on the 15. If I win, we add what I win by onto the five hours I already have, and the hours turn into days. In other words, if I win by three, that's eight total, and I get her for eight days." Jim and Annie talked it over, and finally agreed. Bobby video taped it again. It was Jim's turn to break, and he tried to play safe, but blew it. Bobby made eight in a row and then missed. Jim cleared the rest. "OK," Bobby said, "I win by one. I own her for six days." Bobby turned to Annie. "So, darling, tell me about yourself. How much experience do you have with sex?" Annie practically whispered, "None." Now it was Bobby's turn to be surprised. "None? You mean you're a virgin?" "Yes." Bobby said, "Interesting, so tell me what else you have done. You give blow-jobs? Hand jobs? You ever take it up the butt? What have you done, and how old are you? "I'm 19, and I've never done any of that. I've kissed two different boys." Jim hadn't known Annie was a virgin. He said, "Look, Bobby, give me one more chance. Let me win her back, OK?" Bobby thought about it. "Fine, but here's what I offer. If you win, even by one ball, you take Annie and we're square on the 15, but if I win, I own her permanently. Take it or leave it." Jim and Annie didn't know what else to do, so Bobby taped their agreement. Bobby said, "I know this isn't exactly a legal contract, and if Annie takes a powder on me, I'm stuck, but it would be bad karma for her to do that. Who knows what kind of bad luck would follow something like that?" Jim didn't know how he got into this, and Annie was just sort of numb. No men had ever seen her naked before, and here she was, naked in front of two men, one of them her brother. It was Bobby's break. He got lucky and made one off the break. Then he ran the table. There was a long silence, and then Annie started crying. It was Jim's turn to look stunned. Bobby waited a minute and then said, "OK, when do I get my 15 large?" Bobby let it sink in a minute, and then said, "Alright, everybody knows what a nice guy I am. I'll give you one more chance. Annie has a sister, right?" Annie started yelling, "No, NO, NO," over and over again. Bobby grabbed her arm and pushed her onto a sofa. "Shut up, doll. I own you, permanently, so don't you try to tell me what to do." He turned to Jim. "You get her sister to agree, and we'll play one game of nine ball for her. If I win, I own her, too, and if you win you get both women back. Either way, I wipe the 15. If you agree, go convince her and bring her back here." Jim only thought a minute. He knew he really had no choice. He just walked out the patio door, and didn't say a word. After he left, Bobby walked over by Annie. His first words surprised her. "I'm sorry. I didn't know you were that inexperienced or I wouldn't have made you strip in front of Jim. Anyway, I need some more information. Do you know how to masturbate?" Annie was still in shock. "I think so. I tried it a couple of times, and it made me feel good." "OK, honey, put your hand between your legs and masturbate for me." Annie tentatively started rubbing her pussy with the fingers on her right hand. She didn't look trimmed, but her bush was short. Bobby just watched her for a few minutes, and then said, "OK, stop for a second. I want to see if you are wet." When she moved her hand, he ran two fingers up her slit and held them up for her to see. "Gosh, darling, you are soaked. You must like this." He took his fingers and smeared her juices across her upper lip. "There, now you can smell yourself. Put your hand back and get busy. Tell me if you think you are going to come." Annie closed her eyes and started again. Bobby said, "Open your eyes and look at me, darling. I want to watch your face." Annie opened her eyes. She was squirming a bit now as her excitement rose. She stared into his eyes as she rubbed her fingers up and down her pussy, and Bobby stroked her hair and lightly ran his fingers over her nipples. Pretty soon she was moaning a little, but trying to hide it, and shortly after that she whispered, "I think I'm going to have an orgasm." Bobby immediately said, "Stop! You can't come without my permission, understand?" She was still looking into his eyes, and just nodded. His hands just kept stroking her. After a couple of minutes, he said, "OK, start again." She nodded again, still staring into his eyes, and put her hand back between her legs. Before long she was panting and moaning openly. She said, "Please, can I have my orgasm now?" Bobby just said, "Stop!" He kept letting her masturbate until she was close and then stopping her. He never told her to beg, but by the fifth or sixth time she was shamelessly pleading to be allowed to come. Finally, he said, "OK, come for me on the count of five. One, two, three, four, ........ five." Annie nearly exploded, she came so hard. She though she might faint. It just went on and on. Bobby held her and stroked her until she quit shaking. She stared into his eyes the whole time. When she had settled down, he pulled her head against his chest and hugged her. "How was that, then?" he asked her. "It was amazing. How did you make me do that? I must be a slut or something." Bobby chuckled at her. "Don't worry. You are perfectly normal. Sex should be amazing. Just wait until we get you really warmed up." He handed her a throw off the back of the sofa. "Wrap up in this. Your brother will be her pretty soon. Until he gets here I want you to see how many times you can come, so play with your pussy under the throw. When your brother gets here, I want you to keep masturbating secretly under the throw, but you can't come while he's here, and when he leaves you need permission. As Bobby got up from the sofa, Annie touched his arm. "Please, could you do me a favor? Win my sister Amy. She would be better off away from my brother. He'll just lose her to someone else now that he has the idea she's worth something." Bobby stopped. "How old is she?" "Amy was 18 last Saturday." Bobby thought. "OK, I'll give it a try, but only if you come at least three times before Jim gets back, so you better get busy." Bobby passed the time throwing darts and watching Annie on the sofa. After a couple of minutes, she had opened the throw so she was fully exposed. When Bobby gave her a quizzical look, she said, "It turns me on to know you're watching me." Jim showed up about a half hour later, with Amy in tow. She looked scared out of her wits. Annie covered herself back up before they came in, but by then she had come four more times, and she was covered in sweat with her hair matted down. When Jim and Amy came in, Amy ran to the sofa and hugged Annie. Annie whispered in her ear, and Amy gave a strange glance at Bobby. Jimmy said, "Let's get this over with, you bastard. I want to get my sisters home before you rape Amy, too." Bobby laughed at him. "Well, at least you're confident. Of course, I didn't rape Annie, did I Annie?" She looked right at her brother and said, "No he didn't rape me, and I don't think he will. I think in a little while I am going to be begging him to do me." Bobby taped Jim and Amy agreeing to the new deal, and then said, "Ok, let's go." Bobby had the balls racked for nine ball. It was Jim's break, and he made the seven off the break. Unfortunately, the one ball ended up blocked behind some other balls, and Jim missed his attempt to bank into it. It was a table scratch, and ball in hand for Bobby. Bobby looked over at Annie, and said, "This one's for you, honey, just like I promised. You did good." Then he looked back at Jim and said, "Watch and learn." With that, he placed the cue ball on the table, lined up, and stroked it. The cue ball hit the one, made two rails, and dropped the nine in the side. Game over. Bobby turned to Jim. "OK, this is what you are going to do. Here's 200 bucks. You're going to go rent a truck, and you are going to load everything that belongs to these girls into it, including family photos, documents, whatever. You will have that truck here by noon tomorrow. If anything is missing or damaged, you will be too. After you unload the truck you are going to leave the state and never come back. Your rights in this state have been revoked. Understand?" Jim just nodded and left. The moment the door closed behind him, Annie said, "Please, may I have an orgasm now? Please?" Bobby let her beg for a couple of minutes. Amy was staring at her with an amazed expression on her face. Finally, Bobby told her to go ahead and come, and her whole body arched into the air, almost lifting her clear of the sofa as the most powerful orgasm yet overwhelmed her. Amy and Bobby both watched fascinated as wave after wave of pleasure washed over Annie. When it was over, Bobby told Annie to put her hands on top of the throw and wait quietly while he talked to her sister. Bobby sat in a club chair and motioned Amy to stand in front of him. When she was there, he said, "So, what did Annie whisper in your ear when you first got here. Be sure to tell the truth, because Annie will tell me if I ask her." Amy looked at Annie for a moment, and then said, "She told me not to worry. She said you would win, and I would be better off." Bobby said, "OK, now tell me about your sexual experience. I want to know if you're a virgin, and if you aren't, I want to know when and how you lost your cherry. I want to know if you have ever given or received oral sex, had anal sex, given a handjob, French kissed, and so on. Don't leave anything out. I own you now, and I want to find out about my new property." Amy turned bright red, but didn't say anything for almost a minute. Bobby just waited. Finally she took a couple of deep breaths and started. "I'm a virgin, and I have never done any of those things. I have never even seen a penis, except in pictures in health class, and I've never kissed a boy. Are you going to rape me?" "No, probably not. Do you want me to rape you? Are you going to be disappointed if I don't? Do you want to see a penis? Do you masturbate?" Amy took a couple more deep breaths. "No, I don't want you to. Please don't rape me. I have played with myself in the shower a few times." Now she was bright red, and she didn't think it was possible to be more embarrassed than she was right then. She was wrong. "OK, Amy, undress now. I want you standing right there naked in about one minute. Don't make me wait." Amy had known it was coming, but it was still a shock to hear the words. Like her sister, no man had seen Amy naked since she was a little girl. It took her a minute to work up the nerve to start, but her sister encouraged her, and once she started, she undressed in record time. She thought it would be easier if she just got it over with. Once Amy was naked, she stood there, shivering slightly, right in front of Bobby. He didn't say a word. He just watched her. Before long, she was shivering harder, and was still bright red. Finally, Bobby reached up and lightly ran his fingers up her slit. She made no effort to stop him. He grinned at her. "You're soaked, girl. You're really turned on, aren't you?" Amy just nodded. "Why are you so turned on?" Amy didn't know what to say. "I don't know. I never felt like this before. I'm a good girl. Please, let me get dressed." Bobby ran his fingers up and down between her pussy lips, and she shuddered violently as he did. "Is this how good girls act?" Amy shook her head no. "Well, then I guess you have to be punished, don't you? Lie down over my chair." Bobby guided her so she lay over the padded leather arms of the chair, with her hands barely reaching the floor on one side and her feet in the air. She wasn't really lying on him, because the arms of the chair held her up off his lap. When she was in position, Bobby said, "Tell me you've been a bad girl, and ask me to punish you." Amy was starting to sob, but managed to say, "I'm a bad girl. Please spank me." Bobby reached under her with his left hand and began circling her clit with his fingers. Then he started spanking her with his right hand, very gently at first. Amy started moaning almost at once. As Bobby spanked her harder and harder, she moaned louder and louder. Bobby warned her not to have an orgasm without permission. Amy's mind was whirling and she felt so dizzy she thought she might die. She had always had fantasies of being captured and then spanked by some powerful man, and she didn't know how he had known to do this to her. It was like he could see inside her mind. Finally, she started begging. "Please let me have an orgasm. Please give me permission. I can't stop it. Please. Please. Please." Bobby just said, "OK," and kept spanking her. She came almost instantly then, her mind whirling faster and faster as she spiraled out of control. She had brought herself off a few times in the shower, but those experiences did nothing to prepare her for this. Her body spasmed completely out of her control, and only Bobby's strong arms kept her from falling to the floor. Her mind spun down and down into a black whirlpool. When she came back to herself, Amy was lying in Bobby's arms on the sofa, with Annie kneeling on the floor next to her. For some reason she felt very safe lying on his chest. They had covered her with the throw, but she was still shivering a bit from the aftermath of her incredibly powerful orgasm. Bobby was kissing her forehead gently, while Annie was rubbing her feet. "Did I pass out?" "No, darling, you didn't quite pass out. It was close, though. Was that better than the shower?" Instead of answering his question, she said, "Now I know why Annie told Jim she would beg you to do her. What are you going to do with us?" Bobby smiled at her. "I'll do whatever I want with you. I own the two of you." Both girls knew it was true. Their brother may have lost their bodies, but Bobby had claimed their spirits. Bobby held Amy for almost an hour, and she slept most of that time. When she woke up, she was still lying on top of him, under the throw, and her sister was sitting on the floor with her head leaning against Bobby's side. Annie was sound asleep. Bobby and Amy tried to slide out without disturbing Annie, but she woke up. Once both girls were fully awake, Bobby asked them if they wanted to see the rest of the house. When both expressed enthusiasm, he took them on the "Cook's Tour" of the place. His house was the biggest the sisters had ever been inside. There were three floors, seven bedrooms, 10 baths (one for each bedroom and a public bath on each floor), sauna, hot tub, indoor pool, professional class workout room, a huge living room, library, ... well, you get the idea. Amy asked and was told the house was about 14,000 square feet. During the tour, Bobby showed them his huge master suite, and asked if they could keep a secret. They both said they could, but he made them both swear and promised them dire consequences if they ever told. They he showed them the concealed panel that slid back and gave access to an entire hidden complex. There were passages that connected to most of the other rooms, secret staircases, and whole hidden rooms. Bobby said he was only showing them because he owned them and they would be living in the house from now on. He also told them that the bedroom closest to his would be theirs to share. It had easy access to the master suite via either the regular hallway or the secret passages. Like all the rooms, it was ample in size, and would easily accommodate two full or queen beds. He explained that they would have to shop for furniture in the next day or two. After they had toured the house, he brought them back to his master suite and told them to both lie on the bed. They were both still naked, of course, and had been throughout the tour, so Bobby hit the remote for the gas fireplace. Then he told them both to masturbate for him. "Remember, you can't come without my permission, so don't forget to ask. You may begin." Annie and Amy were a little embarrassed to be lying side by side, but they seemed to be getting less nervous about the whole situation. Annie was first, begging Bobby for permission to come. He let her beg for a while, until she was quite frantic, and then made her stop and lie still. Meanwhile, Amy was getting close and started to beg for release. As with Annie, he let her get pretty frantic before stopping her. The three of them continued like this for nearly an hour, and both girls were so close to coming that he could only let them rub their pussies for a minute or two before he had to stop them. Finally, he made them both stop. Then he flipped a coin, and Annie won. Bobby got on the bed between her legs and started running his tongue up and down her slit, around and around her clit, and then back up and down again. He had told her it was OK to orgasm now, and she quickly did, but he continued to lick and suck her until she lost count of how many times she had come. Meanwhile, he was making Amy rub herself until close every few minutes. After about 1/2 hour of keeping Annie in ecstasy, he switched to Amy, giving her permission to come. For the next 1/2 hour, he brought her to one crashing orgasm after another. When he was done with them, both girls were as tired as they had ever been, and both were thinking that the life of a slave wasn't so bad. Annie finally asked, "When are you going to have sex with us. I thought you would have by now. I don't think either one of us would mind." Bobby laughed quietly. "You call that begging? You'll have to do a lot better than that before I agree to penetrate either of you. You will, too. I promise. Let me tell you how it's going to work. You girls had no experience giving or receiving sexual pleasure. I decided it would be best to teach you about receiving pleasure first, so that's what we've been doing." "When I think you are getting good enough at that, I will start you learning how to give pleasure as well. You'll start with some basics, like hand and mouth work to make a man happy. You don't get to have intercourse until you know how to give and receive pleasure. When I think you're ready, I'll get you really ready. I'll probably make you masturbate like I just did, but you won't be allowed to come until you convince me to break your cherry. After a couple or three hours of this kind of stimulation, I'm sure you will beg very prettily for my cock. Now let's go find some dinner." Bobby led the two girls to the kitchen. Along the way, Amy said, "Can I ask something?" When Bobby told her it was OK, she said, "When can we get dressed?" Bobby's answer surprised both of the sisters. "I've been thinking about that. You won't be allowed clothing of any kind as long as you are virgins, and even when you aren't, you will have to earn the privilege of wearing clothes. It may be weeks. If I were you two, I'd get used to being nude. Luckily I have the secret passages, so you will be able to move around unseen if necessary. I don't want anyone else seeing you two naked. I don't share." When they got to the kitchen, Bobby asked the girls if they could cook. Both said they could cook pretty well, since their brother had made them do all the cooking. Bobby told them to look around and rustle something up quick. They found some roast beef and stuff in the fridge, and asked if hot roast beef sandwiches would be OK. Bobby agreed, and a few minutes later, they had them done. They sat around the kitchen table eating the sandwiches and talking. Both sisters were surprised at how comfortable they had started feeling, considering the situation. Bobby said he was glad they could cook, because that would now be one of their jobs, along with some cleaning. He asked how they were enjoying themselves so far. Amy said, "It has not been as bad as I feared when you first made me undress. When Jim lost us to you, I thought you might be going to make us prostitutes or something. I am still a little scared, though. I really don't know what is going to happen to us." Annie added, "I guess I feel pretty much the same way. You haven't hurt us, but we don't really know you. It seems pretty OK so far. I had expected to be raped right away. Thank you for not raping us." Bobby smiled at them. "Well, there's no reason for you to worry as long as you do whatever I tell you to do. I plan on keeping you two right here. I will teach you what you need to do to make me happy, and then you just have to do it. Now, Amy, tell me why being spanked earlier got you so hot. Do you want me to do it again?" Amy turned red all over. She started to speak a couple of times, but the words just wouldn't come out. Finally, she said, "I don't know how you knew to do that. I have had fantasies about that for years, almost as long as I can remember. I don't know why it affects me like that. I used to think about being spanked when I played with myself in the shower." "I don't really know if I want you to do it again or not. It was really scary. I don't mean the spanking. I mean my reaction. I got so aroused when you made me undress, and then it just got worse. I've never felt like that before. I couldn't stop myself, and then I came so hard, I thought I was dying." Bobby looked her right in the eyes, locking his gaze with hers. She couldn't look away. He said, "Earlier today, you called me a rapist. You thought I was going to rape you. Was that nice?" Amy's voice was almost a whisper. "No, it wasn't nice. I'm sorry." "It was rude, wasn't it?" "Yes." "So, are you a rude girl?" "Yes, I guess I am. I'm sorry." "Is that what good girls do, being rude to their host?" Suddenly Amy couldn't breathe. Her chest felt like something was tightening around it. His eyes were still locked on hers, and she was shivering and sweating at the same time. He said, very quietly, "Answer me, Amy." It took everything she had left to say, "No, good girls aren't rude to their host." "No they aren't," Bobby replied. "So, if you aren't a good girl, what kind of girl are you?" Annie was watching her sister with her mouth open. Amy started to sob lightly. "I guess I must be a bad girl." "If you're a bad girl, what should I do with you?" "Please don't make me say it, please." Bobby just waited. Amy was sobbing louder now. She took a shuddering breath and said, "Bad girls should get spanked. Please spank me." Bobby stood up and took her hand. He led her to his bedroom and sat on the edge of his bed. Then he pulled her across his lap. This time he didn't rub her clit or pussy at all. He just started spanking her very gently, but gradually increasing both speed and firmness. Soon his hand was leaving red prints, and her bottom was glowing. Bobby kept a steady rhythm, never letting up, and Amy felt herself getting more and more sexually excited. Finally, she couldn't stand it, and started begging. "Please make me come. Please. Please. I need to come so bad. Please help me. Please make me come. Please. I'll do anything you want. I will. Please make me come." She was sobbing and begging and writhing on his lap. Bobby suddenly slid his other hand under her and started flicking his fingers over her clit. "OK, Amy, come for me right now." It was like she exploded off of his lap. Bobby wrapped his arm around her to keep her from falling and rolled her backward onto the bed, landing with his face between her legs. When his tongue hit her clitoris, she wailed, an inhuman, primal sound, and her whole body went rigid. Her muscles were twitching with spasms, and she wailed and sobbed as the mind-wrenching orgasm just went on and on and on. Bobby reached up and rolled her nipples between his thumbs and fingers. Her back arched as the orgasm reached a new level, and suddenly she couldn't breathe at all. Then everything spun down into black again, and when she came to her senses, she was lying on the bed cradled in Bobby's arms. He said, "That worked pretty well. In a day or two, I'm going to do that and you are going to beg for my cock. Imagine how it's going to feel when you are in the middle of an orgasm like that and I shove it up your pussy." Amy could imagine all too well. Suddenly, she couldn't wait. She knew she'd beg for it whenever he was willing to let her. Annie was still in shock. She had followed them to the bedroom, and the power of her sister's orgasm had frightened her. What scared her more was that she was tempted to tell Bobby her own fantasies, and she didn't know where that might lead. What scared her even more was that her current situation was very close to her fantasy. An hour later, Bobby left Amy sleeping on his bed and led Annie to the living room. He sat in a large leather armchair, and told Annie to kneel at his feet. Bobby knew she was a submissive, like her sister Amy, because of how easily she had come over and over in the rec room earlier. Now he just needed to find what really put her over the top. "Tell me, Annie, do you dream of being spanked, too? Or maybe it's something else? Tell me now." Annie had really known it was coming, but it still caught her by surprise. "I can't... maybe sometime, but not now. Please." Bobby caught her eyes in that gaze neither sister could look away from. "Never say 'no' to me. If you don't tell me now, I'll get a riding crop and whip you until you do." He saw Annie's eyes freeze with fear, and her breath suddenly got ragged. He said, "Wait right there," and got up and left. In a minute, he was back, and he was carrying a black riding crop. He went to the stereo and put in a CD. When the music started, he told her, "Get up and dance for me. Make it good." Annie's eyes were like saucers. She practically stumbled to her feet, and started to sway to the music, trying to get the rhythm so she could dance. She couldn't tear her eyes from the crop in Bobby's hand. After a moment, he came over to her, and pulled a blindfold from his back pocket. He led her into an open area and put the blindfold onto her, and then told her to start again. Annie finally started to really dance, but Bobby paced around her telling her she would have to do much better if she was going to please his men. When he said she would have to please his whole crew, she was so startled she gasped out loud. Bobby caught it instantly and switched to a pirate theme. "You landlubbers are all alike. None of you can dance a lick. If you don't improve, I'll have my bosun string you from the mast and whip you bloody. Unless your daddy ransoms you, you'll belong to my crew, and they're a cutthroat lot, so you better please 'em." Then, as he walked around her, he started flicking her with the crop. Across her butt, a nipple, her belly, even her pussy, she never knew where it would strike next. The music, her dancing, the crop, his words, all became a blur as she fell further into her pirate fantasy. She could feel the arousal running down her thighs. Then she heard herself speaking. "Please, Captain, don't give me to your crew. I'll learn to please you. Please give me a chance." Bobby was slapping her faster and harder with the crop, and she was getting dizzy with the need to come. She started begging him. "Please, Captain, make me come now. I need it. Please. Please. Do whatever you want, but please let me come." His voice snapped at her. "Down on the floor and spread your legs, wench. Now!" Annie quickly lay on her back and spread her legs wide, wondering what was next. The crop answered her, slapping against her pussy. Over and over it fell, as Bobby spanked her pussy with the flat leather of the crop end. She never thought of closing her legs. She just arched her back and moaned. Her orgasm took her with no warning, and she screamed. The crop continued to fall a few more times, pushing her higher and higher, and then was suddenly replaced by his tongue. Bobby had to grab her hips to control her as she bucked, and then, like Amy, her screams turned to wails as the power of the orgasm swept over her. It seemed to last forever, and then she was on the sofa. Amy was wiping her forehead with a cool rag, and Bobby was gently stroking her body with his hands, mumbling words of comfort to her. When she had come back to herself, she smiled at him to let him know she was OK. He smiled back and said, "In a couple of days, you are going to beg that Captain for his cock." "Yes, I will," was all she said. Amy was grinning at her. "I guess he figured out the pirate thing, huh?" Annie started to laugh, and it felt good. She couldn't remember ever feeling this good. Pretty soon Amy joined in the laughter. Both were thinking about sex, and neither could believe they were aroused again already. Bobby told them to follow and led them to their room. He told them to sleep well, because they would be busy tomorrow. They had to learn to please him. Both the sisters were asleep almost before their heads hit the pillows, and the dreams were very sweet indeed. So much for day one. Let me know if you want to read what happened the next day. Oh, and just a quick warning so you won't be disappointed. I'm not really into incest. It just doesn't happen to be one of my kinks, so don't look for the sisters to do each other.
Be sure to read Day 01 of this saga to learn what happened so far. Gambling Debt Day 02 & 03 Bobby was up early, as usual, but he let the sisters sleep in. He knew they had been through a stressful day, and he wanted them well rested. At 10am he went into their bedroom and woke them. Bobby left a tray with some rolls and hot chocolate, and told them to be cleaned up and in the living room in 1/2 hour. After Bobby left, Annie said, "Well, Amy, what do you think? It hasn't been too bad so far? I hope Bobby isn't just lulling us into this before he shows his true nature." Amy said, "I'm not that worried about Bobby. I don't think he will really hurt us. I'm just so mad at Jim. Our own brother sold us into slavery, and he thought we would be raped, too. He did it anyway. I've known for a long time that Jim wasn't really a nice guy, but I never, never thought he'd do something like this. I wish he was dead." Annie thought about it for a minute. "You're right, but don't worry about Jim, either. He's a loser, and he always will be. He'll be more miserable alive than dead. Besides, you know he'll get into trouble again, and he's out of sisters to sell. The next time, somebody will kill him." Amy said, "One of us better jump in the shower. We have to get going. I don't want to keep Bobby waiting." "OK," Annie replied. "You eat, and I'll shower." Taking turns, both sisters were showered and had their hair blown dry by 10:20. Since they didn't have any clothing or makeup to put on, they were ready to go downstairs. Although neither mentioned it, they had both been thinking about sex since waking. When they arrived in the living room five minutes early, both were flushed, and not just from the walk down. Bobby wasn't there, and Amy said, "Well, what do you think we should do?" Annie shook her head. "I don't know. Do you think we should go looking for him? He told us to meet him here at 10:30." Amy answered, "I know. I think we should just wait here." She walked to the middle of the room and just stood waiting. Annie joined her. At exactly 10:30, Bobby walked into the room. "Good, right on time I see. Why are you standing in the middle of the room? You can sit down if you want." Annie said, "Amy was standing here, so I just joined her. We didn't know if we should sit or not." "Is that right, Amy?" Bobby replied. "Why did you decide to stand there?" Amy mumbled something he didn't catch. "Amy, look at me and speak up." Amy had trouble meeting his eyes. "I didn't want to make a mess on the furniture. I thought you might be mad at me." Bobby walked over to her, and stood in front of here. He had a questioning look on his face. He stood in front of her for maybe a minute, watching her eyes dart back and forth like a trapped animal looking for a place to hide. Then he gently reached down and ran his fingers up her slit. He held his fingers up and sniffed them, and then smiled at her. "I see the problem, Amy. What should we do about this?" Then he held his fingers up to her lips, and, using his own tongue, indicated she should lick them. Amy was quaking and breathing fast, shallow breaths. As she pushed her tongue out and licked his fingers, she moaned, almost to low to hear. "Well," Bobby repeated, "What should we do about this, Amy?" Amy looked into his eyes and said, "Please let me have an orgasm. It's all I can think about. Please." Bobby smiled at her again and lowered his hand back to her slit. He wrapped his other arm around her and pulled her in tight against him. Bobby slowly massaged her pussy lips, never touching her clit, until she was moaning louder. Then he slid his soaked fingers between her labia and began rubbing her clitoris gently, but insistently. Her moans got louder and faster, and her breathing became ragged. The pitch of her moaning rose until it was more like whimpering, and Annie could smell her arousal from five feet away. Bobby said, "Come for me when I get to one. Ten, nine, eight, seven, six, five, four, three, two, one." Amy arched her back and came the instant he said "one." Her whimpering became a scream, and she pressed herself as hard as she could against his fingers. After a few moments, he was holding her up with his arm around her as she almost collapsed against him. Bobby continued to massage her clit as she calmed down and managed to stand on her own. When she was OK, he led her to a sofa and sat down, pulling her down to sit on his lap. Then he looked at Annie and patted the sofa beside him. Annie practically ran to the sofa and sat down beside him. He wrapped one arm around her and pulled her in to cuddle against him, while Amy pulled herself into a ball on his lap and pressed herself against his chest. Bobby just held the two of them for a few minutes, and then moved Amy so she was sitting beside him. Then he felt Annie's sex. She was as wet as Amy had been. Bobby pulled her until she was lying face down across his lap and then reached between her legs from behind and started his sensual movements. There was no way her body could resist his finger dance. Annie's heart started to pound so hard she was sure he must be able to hear it. Then Bobby said the magic words she longed to hear. "Go ahead, Annie. Come for me." When her orgasm finally subsided, Bobby pulled Amy and Annie against him, one on each side, and just held them. After a time, Annie said, "Thank you so much. I was afraid yesterday was just a dream." Amy just said, "Me, too." Bobby laughed. "It's not so bad, then, being owned by me?" Both girls said, "No," at the same time, and then both of them laughed along with Bobby. After a minute, Amy asked, "Should we call you 'master' or anything? I've never been a slave before, so I don't know how to behave properly. Will you tell us if we make a mistake?" Then she ever so tentatively put her hand on his lap and rubbed a bit. "When do we learn how to make you happy?" Bobby looked down at Amy and saw she was blushing furiously all over. "I want you to call me Bobby. Now, I only count mistakes if I have told you something and you don't do it. If you are trying your best, I will help you until you get it right. I am not going to try to trap you into making mistakes. If you do your best to be obedient to my will, everything will go very smoothly. I want happy slaves, not fearful slaves." Annie said, "Well, so far so good, then. I'm not afraid, and I am very happy right now." She snuggled a little closer. Bobby hugged her tighter. "OK, my little wenches, how do you want to handle the visit from your brother? He will be here in about 1/2 hour. I am going to have him back the truck up and unload it into the garage. You can watch on the security cameras, and we will want to make sure everything is there that should be there. After that, you can say goodbye to him if you want. If you want to say goodbye to him, I will make an exception to my nudity policy and let you wear robes. If I were you, I would be pretty mad at him, but he's your brother, and you probably won't see him again for a while." The sisters discussed it for a few minutes and decided they would say goodbye to Jim once the truck was unloaded. Bobby encouraged them to do this, because he knew they would regret it later if they didn't. He also suggested they keep the goodbyes on a positive note. "There is nothing to be gained by an emotional display or yelling because he gambled you into slavery playing pool. Just say your goodbyes, and then we will have lunch. After lunch you get to start learning to please me. Amy will finally get to see a penis. How about you, Annie? How many have you seen?" It was Annie's turn to blush. "I've seen about the same number as Amy, although I did get a glimpse once when Jim forgot to lock the bathroom and I walked in on him getting out of the shower." "If you only got a glimpse, I don't know if we can count that. What do you think, Amy? Does a quick peep count?" "No, I don't think so. Annie and I talked about that a few times, and we agreed our brother doesn't count anyway." Bobby chuckled at that. Then he said, "Time for a little contest. When I say go, I want both of you to masturbate for me. Whichever one of you comes first will win. You win two things. The first thing you win is the orgasm, because the slower sister will have to stop and be frustrated until after lunch. The other thing you win is first chance to handle my cock later. Ready, set, GO." Neither sister even hesitated. Bobby held them against him as their fingers flew between their legs. Bobby noticed that Annie was using her other hand to pinch her nipples pretty hard, and he filed that information for later. In about three minutes, Annie announced, "I am coming. I win." Bobby immediately snatched Amy's hand from between her legs. She exclaimed, "Nooo. I am so close. Please let me come anyway. Please." "Too bad, you were just a little slow. Better luck next time. At least you'll have something to think about until after lunch. Let's get ready for your brother." He led the sisters into the secret areas of the house and set them up in front of the video monitors. After showing them how to vary the view, select the microphones, etc. Bobby put a little earpiece into his ear, routed the wire under his shirt, and clipped the transceiver box onto his belt. He then showed Annie and Amy how to talk to him and hear him when he answered. They watched Jim drive in on the monitors. Bobby went down to meet Jim and show him where to unload the girl's stuff. Jim had brought a friend to help unload, and Bobby had them back the truck up to the garage. It took the two of them almost an hour to unload the truck into the garage. Jim told Bobby that he didn't want any trouble, so he had brought everything from the house except his clothing and the furniture in his own room. He asked if he could keep the TV, and Bobby had him leave it on the truck. When they were done, he asked his friend to wait in the truck, and then asked Bobby if he could speak to him. Bobby led him into the living room, and the sisters followed them on the monitors. Since Bobby was wearing the microphone, they could hear what was being said. Jim said, "Look, I am not trying to tell you what you can do. I know it was my fault that I lost my sisters. It was stupid. They probably hate me now. I just want to ask you, as a favor, to please be nice to them. They deserve better than they got from me. I'm going to miss them. I don't suppose I can say goodbye to them." Bobby was surprised. He raised his opinion of Jim a bit. "Actually, they do want to say goodbye to you. I will get them in a minute. I would like you to keep in touch. I will give you an address where you can write to them via email. If you keep your nose clean for six months and keep a real job, I'll help you move back here closer. If you screw up, you'll never see them again." He pulled out his wallet and gave Jim $2000. "Here, this will help you get set up. It's a gift, so don't worry about owing me." Bobby left Jim in the living room and went to get the girls. When he got to the security room, they were holding the robes, but had not put them on. Bobby told them to put on the robes and follow him. The goodbyes were tearful. Jim apologized over and over, and the sisters kept assuring him they were fine and happy. Finally, Jim left, clutching the email address like a life preserver. When the door closed behind him, Bobby turned around to find both sisters had shed the robes. They were both smiling so wide he thought their faces might crack. Amy said, "Thanks for fixing things with our brother. That was really nice." Annie added her agreement. Bobby just said, "Family is important. What's for lunch?" The girls quickly scurried off to the kitchen, leaving the robes on the sofa. In a short time, they had a chef's salad prepared, complete with ham, roast beef, and hard boiled eggs, all on a spinach salad. Bobby told them he was impressed. He also said that in the future they would need to plan meals ahead so the proper shopping could be done. After lunch the three of them returned to the living room. Annie immediately asked if it was time for lessons in how to please him. Bobby replied, "Eager, aren't you? Now you need to be much more specific about what you want. Why don't you both tell me what you want to do? I'm not sure you really want to yet." Amy answered first. "We really want to learn to please you. Please let us. We'll try hard, I promise." Bobby just waited. Annie continued with, "Yes, we'll learn fast. We'll do our best. Please just let us try. We want to learn to please you with our hands and mouth. Please." Bobby let them continue for several minutes, and then stood up. "OK, ladies, I guess we can start. Begin by undressing me. Leave my underwear for last." Amy unbuttoned his shirt, while Annie unfastened his belt and undid his pants. While Amy removed his shirt, Annie pulled his pants down and then lifted each foot in turn, removing the shoe and sock from each foot before sliding his pants off completely. In a very short time, Bobby was standing in his briefs. He made them wait a short time, and then told Annie to continue. She carefully slid his Jockeys over his hips and down his legs, again lifting his feet to remove them. Both girls were now kneeling in front of him, with their faces just inches from his genitals, staring in fascination. Then Annie leaned forward and gently kissed his penis. It was about 3/4 erect, and twitched a bit at the contact. Then, blushing brightly, she pushed her tongue out and licked across the tip. It made her feel so naughty to do that, but the response was worth it. Bobby's cock hardened immediately. Annie looked up at Bobby with a questioning expression. Bobby sat back down and slid forward until his butt was at the edge of the sofa. He spread his legs apart and motioned for Annie to get between them, then had Amy sit beside him. He told Amy she couldn't touch him until Annie said it was OK, since she had won the contest. That made Annie smile. To make it worse, Bobby lightly stroked Amy's breasts and ran his fingers up and down her pussy a few times, increasing her already high level of frustration. Bobby then told Annie to just play a little. "Just do what you feel like doing. Rub with your hands, lick, tickle, or whatever else you think might be fun. Experiment for a while and see what works. While you do that, I'll see if I can drive your sister crazy." Amy was moaning by this time. Annie was having fun. It was like she had discovered a new, very responsive toy. She wrapped her hand around his cock and gently stroked it up and down, planting a kiss on the end every time it came into view. Then she used her hands to fondle and tickle Bobby's balls, while she licked the head of his penis like an ice cream cone. She was staring into his eyes the whole time. Finally, after maybe ten minutes of this, she quietly asked, "Is it OK if I try to suck it?" Bobby said, "Of course, give it a try." Annie opened wide and took the head into her mouth, running her tongue around it. Then she tried to slide deeper, but gagged a bit. After hitting her gag reflex three or four times, she lifted her head and said, "I'm sorry. I'll get it." Bobby said, "Don't worry; I'll help you out a little." Then he reached out and took one nipple in each hand, holding them lightly between his thumb and first finger. Annie gasped a bit. Her nipples had always been very sensitive. Then she tried again. As she tried to slide down his cock, she started to gag again, but Bobby pinched down on her nipples. He didn't pinch really hard, but hard enough to cause just a little pain, and Annie forgot all about gagging as the sensation from her nipples washed over her. Then he pulled down slightly, and Annie slid down a bit further on his penis. They quickly established a rhythm. As she slid down, he would pinch and pull down. Then, when she lifted up, he would quit pinching and push up with her. Annie had always enjoyed pinching her own nipples, and she was really enjoying this. She kept trying to stay down longer to keep the pressure on her sensitive nubs, and she was going down further and further each time, without even noticing it. Before long, she was taking his entire cock and not gagging a bit. Bobby let her do this for a few minutes, and then told her to stop and use her hands again. He showed her how to wrap her hands around his cock and stroke it up and down. Bobby was more than ready. In a short time, he yelled, "I'm coming. Keep rubbing." As Bobby moaned, Annie kept up the stroking, but somehow knew to spend more time on the glans. Bobby flooded her hand and his stomach. When he was done, he looked at both girls. They had watched in awe as they both saw the first ejaculation they had ever witnessed. Bobby reached down and ran his finger through the milky fluid on his belly. Then he licked it off his finger. "See, it's not bad. It doesn't taste terrible or anything. You try it." Annie already had semen all over her hand, and she licked a tiny bit off. Amy imitated Bobby, ran her finger across Bobby's stomach, and then she also licked it off. Annie took a larger taste, and then so did Amy. Both agreed that it was not unpleasant. Then Amy got a mischievous look on her face and licked the rest off Bobby's stomach. Not to be outdone, Annie cleaned the remainder from her hand, and then licked his penis clean. Amy looked at his penis, now much smaller, and asked, "How long before I can play with it? It's my turn. I want to try it." "Patience, darling," Bobby replied. It will be ready again soon enough. In the meantime, I have to slaves to make crazy. I think I'll start with Amy. Remember, you are not allowed to come without permission, and you'll be sorry if you do." Amy was already turned on and frustrated. Bobby slid off the sofa to his knees and started gently running his tongue up and down her pussy. In no time, her breathing was ragged and she was humping up to meet his mouth. As he kept licking, Amy started to beg for permission to come, but Bobby ignored her. Just when she thought she would be unable to hold out another second, he stopped. Annie was still on the floor, but he put her on the sofa and went right to work on her. His excellent tongue work soon had Annie panting and begging for release. When her pleas had become frantic, he stopped. Smiling at the two sisters, he said, "That should hold you for a while. I think I'll have a Coke." He left both girls lying on the huge sofa, flushed with arousal and fully in lust mode. About 10 minutes later, Bobby returned to the living room to find both sisters sitting up on the sofa. They looked hopefully at him as he came into the room. He smiled and said, "So, what have you two been thinking about while I was gone?" Annie gave him a pouty look and answered, "Sex, what do you think?" Amy tried a different approach. She smiled as seductively as she knew how (which wasn't very), and said, "Can I have a lesson in how to please you now? I've been thinking about some things I want to try." Bobby found the girls' innocence charming. They seemed to be genuinely having a good time, and hadn't seemed frightened since the day before. He wanted to bring them along slowly so they would learn to truly love sex, and it seemed to be working so far. He especially wanted their first experience with intercourse to be special, and something they could remember fondly. He was well aware that he would have only one chance with each sister to get it right. Since he was still nude, he just sat on the sofa between them and told Amy to give it a try. Amy straddled him, facing his chest, and with one knee on each side of his legs. Then she sort of squirmed her butt down into his lap and leaned forward, pressing her breasts into his chest. She giggled as she felt his erection rise, looked into his eyes, and then leaned up to kiss him. Bobby said, "Don't do that until you mean it." Amy stopped and looked puzzled. "What? I don't understand?" Bobby smiled at her and said, "Kisses mean 'I love you.' That's why hookers seldom kiss their clients. You aren't a hooker, but the same rule applies. Don't do it unless you mean it." Amy's mind was racing a thousand miles an hour. She knew she was feeling something, and the feeling had been growing. Was it just lust, or something more? Her brain was undecided, but the rest of her knew the answer. She was kissing him before she knew she had decided. Bobby had expected her to stop, and her kiss totally surprised him. She was still looking right into his eyes, and what he saw there made his erection rock hard. Amy maintained eye contact as she slid slowly down his body, kissing all the way. She ended up kneeling in front of him, and ran her tongue around the head of his cock. Then she slid the head into her mouth and started bobbing slowly up and down. She was still staring into his eyes. Amy was frantically trying to remember the instructions Bobby had given her sister earlier in the day. She was swirling her tongue around the head and sucking while she moved up and down, and she was going further down on every stroke. Her nipples were rubbing against his legs as she moved, and her world was starting to spin again. In a couple of minutes, she was managing to take almost all of him, and the whirlpool she was in was getting stronger and deeper. Bobby had never been so turned on that he could remember, and his cock was already starting to throb. In all his experience, no woman had ever looked at him the way Amy was right then. He searched for his voice and found it long enough to say, "I'm coming." Amy never hesitated. This had been her plan from the beginning. She just sped up a bit and kept going. When he erupted, she swallowed everything he gave her and wanted more. Then, the deep eye contact, the feeling of him in her mouth, the rubbing of her nipples, all became too much. The whirlpool pulled her down, she spun out of control, and the orgasm slammed through her. The next thing she knew, she was on Bobby's lap, and he was holding her. Her head was on his chest, and he was stroking her hair. She looked up at him and said, "I'm sorry. I didn't get permission to come." Bobby kept stroking her hair, soothing her. "Don't worry about it right now. I'll punish you for it later on." Then she drifted into sleep. Bobby laid her carefully on the sofa and covered her with a throw. Then he took Annie's hand and led her down to the rec room. Once out of the living room, he said, "Well, your sister had a good time. I think she may be almost ready for the next step. How about you?" Annie smiled shyly, and her voice was very soft. "Just let me know when I can beg that captain. I want him to take me. I've never been so ready for anything." "Well," Bobby replied, "Let's see if you are ready for this." He let her into his workout room. One of the pieces of equipment was an inversion table. It is used so that a person can rotate themselves to an upside down position to relieve stress on the back. Bobby locked it into the horizontal position and helped Annie up onto the table. "Don't worry, I'm not going to hurt you, but I need to tie you to this table. Just relax." "Sure," Annie thought, "Just relax while he ties me down. That's easy for him to say." Bobby quickly used some Velcro straps to fasten her feet to the one end of the table. There were already padded places where her feet could slip so she could hang comfortably. He just made sure she couldn't remove them. Next, he slipped soft cuffs over her wrists. They were padded and fur lined. Once her wrists were in the cuffs, he released the table and swung it to about a 70 degree angle. Annie was almost upside down, but still resting slightly against the canvas sling of the table. Then Bobby tied off the straps on the wrist cuffs to the frame of the machine, so Annie could not lift her hands far enough to touch her own head. Once she was hanging helpless upside down, Bobby started using his mouth on her sensitive flesh. He went from her breasts to her thighs to her nipples to her pussy. Soon she was moaning and thrashing. Bobby avoided her clit and stopped whenever necessary to keep her from coming. Her moans turned into begging, and that soon became frantic begging. All she could think of was coming. The blood was rushing to her head from being upside down, and Bobby just kept teasing and teasing, never quite letting her reach orgasm. Finally, he took pity on her and told her to come. He shifted his attention to her clit and attacked it with his tongue and lips. Annie couldn't even catch enough breath to scream. She thrashed wildly, totally losing control of her body. It went on and on and on, and finally she slipped into oblivion. When she woke, she was lying on the table, which was back in the horizontal position, and her hands and feet were free. Bobby was smiling down at her. "That time you did pass out. I guess that was a pretty good orgasm, huh?" Annie tried to speak, but couldn't. Finally she just nodded. Bobby rubbed her gently for about 10 minutes, and then helped her off the table. He led her into the nearby pool area. "Do you know how to swim?" Annie nodded. "Good, let's get cooled off." Bobby dove into the water. Annie was a little more timid. She went to the shallow end and walked into the water on the steps. Bobby swam over to her, and she was afraid he would splash her or duck her like her brother had always done, but he just massaged her legs. In a few minutes, she was in the water and swimming. After about a 10 minute dip, Bobby led her to the nearby hot tub, and they soaked for a while in the 102 degree water before returning to the pool. After another dip, they returned to the hot tub. Then, after a final dip, Bobby opened a cabinet and brought out the biggest, most fluffy towels Annie had ever seen, and they dried each other off. Annie felt like she was in heaven. She was contented and yet aroused, naked but not shy about it, and really looking forward to giving her virginity to Bobby. She hoped Amy was feeling the same way. She had sure looked like it when they left her. When they got back to the living room, Amy was just waking up. Her face lit up when Bobby came into the room. "Hi. I guess I fell asleep. What have you guys been up to?" Annie said, "We went for a swim and used the hot tub. Too bad you missed it. You look like you could use a dip." Amy could tell by the look on her sister's face that there was more to the story than that, but all she said was, "You're right. I would love to take a swim. Is it OK if I do, Bobby?" Bobby said, "Sure, but Annie has to go with you. It isn't safe to swim or hot tub alone. You ladies run along. I have a little work to do anyway." Amy and Annie went down to the pool and Amy jumped right in. Annie didn't want to swim again, so she just sat in a lounge chair and watched Amy swim, hot tub, and swim again. When she was done, Annie showed her where the towels were found. Then they went up to the kitchen to see what they could plan for dinner. After looking around the kitchen for a while, the sisters decided that tacos were the best bet. Once they made sure all of the ingredients were on hand, they went looking for Bobby to see when he wanted to eat. The found him in his office. He was just finishing a phone conversation. "No problem. I'll take care of him for you. Yes sir, no later than next Friday. Thank you, sir. Goodbye." Amy and Annie gave each other a quick look over the unusual conversation they had overheard. Then Amy said, "If it's OK with you, we are going to make tacos for dinner. When do you want to eat?" "Tacos are fine. We can eat whenever you're ready. What do you want to do after dinner?" Annie blurted out, "Have sex." Bobby laughed. "What do you think we've been doing? I thought you'd be tired of sex by now." Annie looked at the floor. "I mean I want to have intercourse." She blushed all over. "I want you to take my virginity. Please." Bobby walked over and wrapped his arms around her. "Don't worry. It will happen soon enough. I'm glad you're looking forward to it. It will probably happen tomorrow, depending upon how things go. Now, you and Amy run along and get dinner started. I will join you shortly." A short time later, they were all in the kitchen eating the tacos. Bobby was impressed. The tacos were excellent. The sisters really could cook. He had been thinking since the day before about where he wanted this to go. He had always lived alone. While a lot of women had visited his home, none had stayed long. He had liked it that way. Now, suddenly, he found himself thinking of changing all of that. Something about Amy and Annie fascinated him more than any other female had ever done before. He couldn't decide if it was their innocence, helplessness, or something else. For the first time in his life, someone was dependent upon him. The sisters had no home and no money. Their few possessions were boxed and in his garage. While both were high school graduates, neither had any salable skills. Bobby knew that without him they would both be working minimum wage jobs and living in some rented room. When he won them from their brother, it had been a lark. He had never intended to keep them permanently as slaves. He thought he would have some fun until he lost interest in them and then send them packing. In thinking about this he realized his unconscious mind had been way ahead of him, since he would never have shown them the secret passages if they had been temporary. As they finished dinner, he decided to bring things out in the open a bit. "Tell me, ladies, how do you like your time here so far? I want the truth on this. Where do you see yourself in the coming weeks and months?" Annie answered first. "I'm not sure what you are asking. I was scared out of my wits when Jim lost me in the pool game, but it has been fine. You own us now, so I assumed we would stay here. Are you going to send us away somewhere?" Suddenly she looked like she would cry. Amy looked devastated. Bobby took Annie's hand. "I am not sending you away. Don't worry about that. What I meant is not where you would be physically, but where the relationship would be. I grant you that a master/slave relationship is not typical, but it is a relationship. What do you see yourself doing in six months?" Annie answered again. "I thought I would be here, serving you however you want. I think I don't mind having you own me. I'll do whatever you tell me to do. How about you, Amy?" Amy was still recovering from the shock of thinking Bobby didn't plan to keep them. Tears were flowing down both cheeks. "I just want to be a good girl for you. Please don't send me away. I want to stay here. I'll try harder. I can make you like me, I know it. Please give me another chance." Bobby pulled both sisters in close and hugged them to his chest. "I told you don't worry, I am not sending you away. I like having two slaves, and I really like both of you. Amy, you don't need another chance. You are doing fine, and you have been a very good girl for me, except for that orgasm earlier without permission. I am not trying to get rid of you or Annie. I'm trying to decide exactly what to do with you. I never owned any slaves before, you know." Bobby just held them for a time, and then suddenly got up and led them to the living room. He put Norah Jones on the stereo and told them to dance. For the next 40 minutes, he just relaxed on the sofa and watched his two nymphs perform for him. As he watched, he thought about it and decided that this was way too good to ever give up. As they danced, Amy and Annie were also thinking. Amy was remembering how she had felt at dinner when she thought he was planning to send them away. Her chest had hurt so bad she couldn't think, and all her emotions had lunged to the surface. She knew she was in love with her owner. Annie was thinking pretty much the same thing. She felt truly owned, and the thought comforted her. Both were hoping that the next day would bring their first chance to experience intercourse. When the album was finish, Bobby decided to have another contest. "Tomorrow you ladies are going to lose your virginity. The only question is who gets to be first?" Annie blurted out, "It should be me. I'm the oldest." "Well, maybe so," Bobby replied, "But that isn't how it is going to work. I will flip a coin, and the winner gets to start. Each of you will have three minutes to stimulate me however you choose. Whichever one of you makes me come will get to go first tomorrow." Annie won the toss and immediately started using her mouth and hands. Bobby was really getting into it when the timer went off and Amy took over. She cupped his balls and went deep on his cock, working her throat muscles. It was almost enough, but the timer went off while Bobby was just shy of his orgasm. Annie immediately lay across him with her pussy near his face and took over where Amy had left off. The combination of her mouth and hands, with the scent of her very wet pussy just inches from his face, put Bobby over the top. He was watching Amy, and the look on her face when Annie won was priceless. Bobby decided to have some fun putting them to bed. He told the girls to go up to their room and get ready for bed. "I'll be along to tuck you in." They hurried up to their room, talking excitedly about what the next day would bring. In minutes, they were ready and sitting on the bed. Bobby arrived a few minutes later. He had Annie move to a chair, and started with Amy. "Lie back and masturbate for me, Amy." She was already turned on, and soon was moaning. After just a few minutes, she looked up at Bobby and pleaded, "Please let me come." Bobby said, "No, stop right now." She did. He held her gaze. "You were a bad girl earlier. You came without permission. Bad girls like you have to wait. I want you to start again, and when you get close I want you to stop for a little while. Keep doing that." Bobby sat and watched her as she brought herself close to orgasm over and over, stopping each time. Her moans were getting frantic, and she was finding it very hard to quit each time. Finally, she couldn't bring herself to stop, and was racing toward orgasm when Bobby grabbed her hands. Amy practically screamed in frustration. "Please, please let me come. I'll be a good slave. I won't do it again, I promise. Please." Bobby just smiled at her as he pulled the handcuffs from his pocket. He cuffed her hands in front of her and then locked a piece of light chain around her neck and to the cuffs. Once she was unable to touch herself, he rolled her onto his lap and began to slowly spank her, gradually working up in intensity. From time to time he reached under her and fondled her clit for a few moments. Like before, Amy could hardly breathe, and she could think of nothing but her need to orgasm. Bobby continued the exquisite torment for at least 15 minutes, and then suddenly stopped. He rolled her back onto the bed, and tied her ankles together with a piece of cotton rope. He put a blindfold on and carefully taped it into place. Then he covered her up, pulling the blanket up to her neck. "Have a nice night. I'll see you in the morning. Leave the blindfold on. I mean it." Amy's cry when she realized what was happening was primal. "Nooooo. Please don't leave me like this. I'll be good. I'll make you happy with my mouth. I'll do whatever you want." Bobby smiled at her. "I know. You will do all of that, but not tonight. Sweet dreams little slave. Think about how bad you were." Bobby took Annie's hand and led her from the room, turning out the light. Amy's moans followed them down the hallway. Bobby led Annie back to the living room and told her to stand in the center of the room. He turned out all of the lights except a dim nightlight and told her to wait. Then he went to the kitchen, put a pot of coffee on to drip, and hurried to his security room, where he checked on Amy. The cameras all had infrared capability, so he could see her tossing in the dark. He turned up the volume until he could hear her breathing. Bobby knew it would be a long night for him. With Amy tied up and Annie soon to be in the same condition, he knew he would have to keep an eye on them all night. Safety first. He didn't want anything bad happening to his slaves. After checking on Amy he grabbed a few things and slipped back to the living room. He was barefoot, and years of training allowed him to move in complete silence. He stalked Annie like the prey she had become. She never knew he was back in the room until the heavy blanket fell over her. She screamed. He held the blanket against her, pinning her arms to her sides. "That's right mate! Grab the wench. She looks like a juicy one. Bring her back to the ship. We'll show her a sailor's hospitality." He wrapped rope around her, holding the blanket tightly to her body, and tied her ankles. Annie was shivering violently. Then he threw her over his shoulder and carried her off. When he got to the room next door to his security room, he tossed her onto a mattress he had put on the floor, and then slipped over to check on Amy. He also put on a bit of a costume left over from a Halloween party a few years before. The only light in the room where Annie was lying on the mattress was a bare, lurid red bulb. When Bobby pulled off the blanket, Annie screamed again. The lighting, the tattered uniform, and the full face, very realistic pirate mask worked together, and she dropped completely into her fantasy. Bobby reached down and pinched her nipple, and she screamed again. "Shut up, wench. The only use we have for that pretty mouth doesn't require screaming. Now, hands behind you while I slap you in irons. You have a large crew to please, and we've been at sea a long time." Bobby locked her hands behind her. Annie was begging for mercy. "Please, sir, don't hurt me. I'll do what you want. I will. You don't have to hurt me." "Have to? We want to. You're going to scream like a scalded cat. I hope you like pain, dearie." Bobby put a blindfold on her and taped it in place. Then he laughed an evil laugh and slipped to the next room to check on Amy. After a few minutes, he returned to find Annie on her side, still shaking. He silently moved up to her and slapped her on the butt. She screamed again. "Ready for your rape, dearie?" "No, please sir, don't rape me." Bobby rolled her onto her back and pushed her bound legs up against her chest. The chain connecting her hands was long enough that her hands were by her sides. With her legs held up, he leaned down and stuck his tongue up her pussy. She screamed again. He used his tongue to lick and tease her until she was very close to coming, and then stopped, dropping her legs. As he left the room, he could hear her pleading, "Don't stop. Go ahead and rape me. Please." Bobby spent the night alternately checking on Amy and tormenting Annie. By dawn, Annie was almost incoherent. Whenever she thought he was in the room, she begged constantly for the "Captain's cock." Meanwhile, Amy was not sleeping well. She tossed and squirmed on the bed. Bobby suspected it would be time to change the sheets today. Around 3am, Amy started begging for release even though she had no reason to believe anyone was watching her. At dawn, Bobby went into the room with Annie and untied her legs. She spread them immediately, still begging for his cock. He unlocked her hands as well, but she kept them tight to her sides. Once again, he went down on her. As he brought her closer and closer to orgasm, her pleading became more and more desperate. She just kept repeating, "Please, Captain, take me," over and over again. This time Bobby didn't stop. He lifted his head just long enough to say, "Come for me, wench!" Then he kept his tongue busy between her legs. In seconds, Annie was crashing into orgasm. Bobby slid up and kissed her hard. Annie was just lucid enough to remember what he had said about never kissing unless you meant it, and the thought pushed her even higher. She was so wet that his cock slid right in. He only paused a moment when he felt the hymen, and then he plunged right through it. She screamed into his kiss, not from pain, but from the incredible pleasure the brief pain brought with it. She was fulfilled. Her orgasm was more or less constant as Bobby rode her. Finally they both collapsed fully spent. After a few minutes in Bobby's arms, Annie slid down to clean things up, like the good slave she was. She was still wearing the blindfold, and when her mouth found his penis it took her a second to understand what was different. "You're wearing a condom." "Of course," Bobby replied. "You aren't on the pill. If I decide to make you pregnant, it won't be an accident." Bobby reached down and gently removed the blindfold. Annie looked at him with adoration in her eyes. After a few minutes, Bobby got up and went to check on Amy again. Annie followed him. She saw what was on the screen and asked, "You're checking on Amy? Did you stay up all night to watch her?" Bobby smiled. "It isn't safe to leave someone unattended when they are tied up. We don't want anything bad to happen to her." More than anything else that had happened, knowing the lengths to which Bobby had gone to make sure Amy was safe made Annie feel good. Nobody had ever watched out for the two of them like that before. Annie understood that she didn't truly know Bobby, but she trusted him not to really hurt either of them. Annie smiled back and said, "Thank you for a wonderful time since we have been here. I thought it would be horrible, and it could have been. Instead, it has been the best time of my life so far." Bobby just chuckled. "Really? You need to set some higher goals. How long do you think I should let Amy suffer?" Now it was Annie's turn to laugh. "I think at least a couple of hours. How about if I watch over her from here and you take a nap?" Bobby thought that was an excellent idea and accepted immediately. "Wake me around nine, and I'll pay her a visit. If you get sleepy, wake me sooner." A few hours later, Bobby was wide awake and stalking into the sister's bedroom. Annie was watching on the monitor, and Amy had no idea he was there. She was alternately moaning and begging to be released. He stood and watched her from beside the bed for a few minutes. She was trying vainly to rub her legs together. Finally, Bobby reached out carefully and lightly stroked his fingers across her left nipple. Amy's whole body went rigid and she arched up into the empty air. "Is that you Bobby? Please untie me. I'll be a good girl. I won't do it again, I promise." Bobby just waited. Several minutes later he repeated the light stroke, again across her left nipple. Her pleading took on a more desperate note. Bobby patiently toyed with her like this for over an hour. He never said anything, and he moved the touches around. Before long the helpless girl was crying in frustration and begging for him to take her. When Bobby spoke at last, his words froze Amy's breath. "You were a bad girl, weren't you? Tell me why you are being punished." Amy never hesitated. "I was really bad. I came without your permission. I promise I will try to never do it again. I am so sorry. Please forgive me." "Shouldn't you be punished?" This time Amy's words caught in her throat, and it was the hardest thing she had ever done to force them out. "Yes, I was a bad girl. I should be punished. Please spank me. Spank me hard. I deserve it." Amy was sobbing now. Bobby untied her feet and helped her up. He carefully removed the blindfold and led her into the bathroom, where he sat her on the toilet and commanded her to pee. When she was done, he held a wad of TP. Amy had to stand up, straddle it, and rub herself dry. She was completely humiliated. Bobby led her back to the bed. He sat down and had Amy stand in front of him. Then he made her beg again to be spanked. Her arousal was obvious and extreme. Finally he pulled her across his lap and started to spank her very slowly and softly. Over the next 15 minutes, he gradually increased the speed and intensity, bringing her to a height of arousal she had never reached before. She was bouncing and squirming so hard he had trouble keeping her on his lap. Amy couldn't have told anyone who or where she was. She was lost in the sensations of her body, and gasping for every breath. When Bobby slipped his left hand under her and fingered her clit. She screamed. He told her to come, and the sheer power of it overwhelmed her. He picked her up, still thrashing in orgasm, and set her gently on the bed. His face found her slit and his tongue took her even higher. As he licked her, his right hand unrolled the condom onto his cock. As she started to come down a bit, he slid up and kissed her hard, just as he had with Annie. When his cock started sliding into her, her orgasm peaked again, and every muscle in her body spasmed. Bobby slid smoothly right past her hymen, and she barely noticed the moment of pain. Then he was in, and she instinctively began to move with him. Several minutes later, when they were both spent, she was molded to him like they were one. He held her close until she was ready to move again. Amy rolled back just enough to look into Bobby's eyes. "That was even better than I dreamed it would be. It was perfect. Was it that good for Annie?" Bobby's smile warmed her to her core. "She seemed to like it. You'll have to ask her later. Let me know when you're ready to get up." Bobby held her on the bed, and a couple of minutes later, Annie joined them. The sisters were cuddled up to Bobby, one on each side. It was late afternoon when they woke up. Bobby took them into his shower, which was large enough for a party and had several shower heads. They showered for a long time, and Bobby kissed and played with both women while they toyed with him. Annie finally asked how long they had until the hot water ran out. Bobby said, "In my house you can shower as long as you want. You will never run out of hot water." After the shower, they all walked dripping downstairs for a swim and a soak in the hot tub. Amy and Annie were talking about what to make for dinner when Bobby announced, "I am taking you out to the mall for dinner. Let's go get dressed." The sisters practically bubbled over with excitement when they heard this. "Where are we going? What should we wear?" After they dried off, they all went out to the garage, where Bobby helped them find their clothes in the boxes Jim had delivered. They carried all the boxes with the clothes up to the sister's room, and Bobby helped put them away. They finally found a couple of outfits Bobby said were OK. Bobby had them wear slacks and their nicest blouses. He wasn't impressed with their undergarment selection, but had them put on what they had. Some tennis shoes finished their outfits, and they went back to the garage. They got into the Suburban, and headed out to the mall. Bobby had never seen two women so excited. It was crowded, so they had to park some distance away and walk inside. Bobby's first stop was a fancy lingerie shop, and he told the saleswoman that the sisters needed an entire ensemble. Every time they found something they liked and Bobby approved, he had the saleswoman put a dozen or so into their growing pile. Soon they were fully equipped with panties, bras, teddies, and even a couple of very interesting maid's uniforms. They noticed that Bobby didn't have them pick out any nightgowns, but didn't mention it. After the lingerie shop, they headed over to the food court and got some Chinese food. After a quick meal, it was back to the shopping. Bobby's taste in clothing for women ran more to L.L. Bean than Cartier, and those were the kind of stores he led them through. In another hour, they had both more than doubled the amount of clothing they owned. Bobby had arranged for everything but the lingerie to be delivered the next day, and he had the sisters carry that when they walked back to the car. He said it was their stuff, after all. They were nearly back to the car when the three men were suddenly in front of them. They had knives, and the leader said, "Nice chicks. I wish we had a little more time. Give me you wallets. Now." Amy and Annie froze in fear, but Bobby just laughed. "Go home, kid, before something bad happens. We don't want any trouble tonight." The young man gestured at the sisters with his knife and said, "I'm going to count to three, and then my friends are going to cut those pretty faces. One, ..." He never got to say two. The sisters didn't really see what happened. It was too fast. There was an explosion of movement and all three men were on the ground. They did hear a couple of sickening cracks, and two of the men had arms bent at impossible angles. The whole thing took no more than three or four seconds. Bobby hugged both of them to him and said, "Don't worry, it's all over. Are you both OK?" Amy nodded weakly, still too shocked to speak, but Annie surprised herself. She was smiling. Bobby flipped out his cell phone and hit a speed dial number. When someone answered, he said, "K12K5. Sit red. Northwest mall parking lot, row 22W, three muggers down. Request advice." There was a pause of about 30 seconds. Then he said, "Roger, step it up." Annie was looking at Bobby a little strangely. "That didn't sound like a call to the police." Bobby reached over and gently stroked her face. "It wasn't. Look, ladies, there are going to be a bunch of people here in a minute. I'm sorry the evening got a little exciting. Just stay calm. I promise everything is fine. Just act like furniture for a few minutes, and we'll be gone from here. I'll explain as much as I can back at the house." Even after that strange conversation, Amy and Annie never expected anything like what happened. It wasn't five minutes when the three helos appeared overhead. One hovered right over the place they were standing and a dozen men came down zip lines. Nobody in the parking lot had noticed anything happening until now, and the men quickly established a perimeter to keep everyone away. Another helo landed in an open area while the third circled. A woman on the second helo ran over to where Bobby and the women were standing. She was closely followed by another four men. To the surprise of the sisters, she saluted when she arrived, and said, "Good evening, Colonel. How do you want to do this?" Bobby returned the salute. "These men tried to mug us, Captain. Get them some medical attention and then see how General Anderson wants to handle them. Clear the area as quickly as possible. With luck we will be gone before the press arrives. I will drive my friends home." She saluted again. "We'll handle it sir." She turned to the men with her. "Get these slimeballs onto the helo. Make it quick." She turned back to Bobby. "Do you have a plate for your vehicle, sir?" "No problem, Captain. If you are set here, we're going to get going. Thanks for the quick response." Bobby led the sisters over to the Suburban. He opened the back and they tossed their packages inside. Bobby pulled out a license plate and put it over the one on the vehicle. It stuck there with magnets. Amy and Annie got into the car and belted up, and Bobby quickly pulled away. The men stepped aside to let them through. Bobby made several quick turns, including one pass through a parking structure, leaving by a different street than the one he had used to reach the place. In a few minutes he was satisfied that they had no followers, and went home. The sisters were quiet on the trip back. Once they were in the house, he led them into the living room. "Well, I suppose you have some questions. Go ahead, and I'll answer what I can." Annie said, "Those were soldiers and that woman called you a Colonel. You work for the government. Are you a soldier?" Amy chimed in, "Yes, and they acted like we weren't even there. It was spooky." Bobby smiled at them. "I'm sure it was a little odd. They were not noticing you on purpose. That's why I told you to act like furniture. Later, if they are asked, they can say they didn't notice anyone with me tonight. I am not a soldier anymore, but I do work for the government. I handle certain special assignments. Most of them are sort of confidential. I can't really tell you any more than that." Annie answered, "Well, I'm glad you were there. I guess that's why you made us carry the packages. I'm just glad they had knives instead of guns." Bobby smoothed her hair. "It would have made no difference. None at all. Now, I need to ask you ladies something. We are home and inside the house. Aren't the two of you a bit overdressed?" Bobby was glad to see that the response was instantaneous. Thirty seconds later both sisters were naked again. Bobby took out a coin. "Annie, call it in the air." He flipped the coin and she called "heads." It was tails. "Amy wins. Come on up to my room." They all went up to his bedroom and Bobby striped off his clothes. When he was naked, they could see he was already hard. "We are going to do it a little differently this time. I'm going to lie on the bed, and Amy is going to put on my condom and go for a ride. While she does that, Annie will kneel over my head and I'll use my tongue. Once Amy comes, you two switch places. Both women were grinning while Bobby lay back on the bed. Annie quickly got on the bed and straddled him, and he got busy with his tongue in her slit. Amy licked her way up from his feet, and slid her mouth up and down his cock for a few strokes before rolling on the condom. Then she knelt up and slowly lowered herself onto him. In a few seconds, she had him inside and started slowly moving up and down. Bobby had never had two women engaged in sex with him at the same time before, and he was really getting into it. He used his hands on Annie's butt and licked her frantically. Meanwhile, Amy was riding up and down faster and faster as she found her rhythm. She was also using one hand on her clit and the other on her breasts. In a remarkably short time, both she and Annie were screaming in release. As soon as they settled down, they switched, and Annie was riding even faster than Amy had. Meanwhile, Amy hardly paused in her orgasm when she switched places, and was soon coming on Bobby's tongue. A couple of minutes later, Annie and Bobby came together. They finally sort of collapsed into a heap on the bed. Several minutes later, Bobby said, "Well, that was fun." That started both women giggling, and soon they were all laughing out loud. When they were all fairly quiet again, Bobby suggested another shower. When they finished the shower, he brought both women down to the kitchen and sat them at the table. "Now I'm going to ask the two of you a question. I want you to think about it. First, though, I want to say that I love having two slaves, and I hope you don't mind too much. Now the question. Your brother lost you because of a debt he had. It wasn't your fault, and you shouldn't lose your whole lives because of your brother's bad decisions. So, if you want to walk away from it, I'll let you. I'll even help you get set up and educated so you can make a real living." "If you decide to stay, and I hope you do, I won't ask you again for five years. Until the five years are up, you will be my slaves, with no choice in the matter at all. From what happened earlier this evening, you may understand that going to the authorities would be no help to you. They will side with me, I promise." "At the end of the five years, I will ask again, and you can choose to leave or stay another five years. That's how it will work. You slavery runs in five year terms. Make your choice now." The two sisters looked at each other for a moment and then back to Bobby. "I'm staying." "Me, too." "Good, that's it then. You can make a nice snack and then come into the living room and dance for me. Tomorrow, we will get this household back on track. I work out a lot, and from now on, so will you. Tomorrow we'll get you familiar with the equipment and set up a program for you to get started. You will also both start doing laps in the pool and some work on a treadmill." "I also want you to start organizing your work around the house. You will need to inventory the pantries and freezers and make a shopping list, just for a start. Oh, and we will start looking for some online universities for the two of you. Any questions?" Amy and Annie both raised their hands. Bobby looked at them and said, "Very funny. What's your question?" They both smiled at him and then Annie said, "I was just wondering if you would let me make you happy with my mouth later." Amy chimed in, "No fair, that was my question, too." It was a long but satisfying evening. Thank you for the wonderful feedback I received about Day 01 of this story. I hope you enjoy this installment just as much.
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