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.