Chapter 33: Christmas Eve
I was spending Christmas Eve with Jess and Rachel. We did not celebrate Christmas, so my parents did not mind, nor did they mind that Michelle came along with me. Rachel's family was not religious, but they celebrated with the traditional trappings: tree, lights, presents.
We had a nice dinner, but then again, what dinner would not be nice with 6 bare boobs staring at you throughout the meal. After dinner, we retired into the living room and gathered around the tree to exchange gifts. I actually had the girls get into pajamas, because that is how Rachel remembered it from when she was young.
Jess gave me some nice clothes, Rachel gave me a computer game, and Michelle gave me some CDs. I gave Michelle an MP3 player that I knew she wanted, and both Jess and Rachel got necklaces. When I saw them, I knew I had to get them for my ladies. They had platinum chains, and each came with a pendant of a naked slave girl, her hands tied behind her back. From far away, it just looked like a silhouette of a girl, but the craftsmanship was excellent, and if you looked closely, the etching clearly showed a bound slave. Mother and daughter both loved them.
The next round of gifts was more interesting. I got both Jess and Rachel soft leather cuffs to wear around the house, and I gave Michelle a gift certificate which entitled her to Rachel and Jess for a night of pampering and pleasure. She could pick a night to come over and Rachel and Jess would give her a sensual massage, followed by a night of any type of sexual activity that she wanted.
Jess gave me a brand new whip, and then took off her pajamas so that I could test it. Before we got too carried away, however, Rachel said that she had one more gift for me. I knew where the gift was, since there had been a huge box sitting in the corner all night, with a big red bow on it.
Rachel handed me a pair of scissors and said, "This is the last present of the evening. It's really two presents rolled into one, but I hope you like it."
I really had no clue what it was, so I went up and cut the ribbon off, then pulled the top of the box off. I was surprised when I looked inside and I saw a girl, duct tape over her mouth, her hands on her stomach, also bound together with duct tape, and her thighs and ankles bound the same way. There was an envelope attached to one large breast by a safety pin through the nipple. I undid the pin and removed the envelope. I took out the card and read it.
Dear Jeff,
My name is Anne, and I am your Christmas present. I am here of my own free will, and I have been provided to you by Rachel. I am yours to do with as you want for the next three days.
I am a virgin in every way, and I hope that by the end of the night, that is no longer the case. I am a pain slut; Rachel says that I enjoy pain even more than she does. I do not enjoy the humiliation that Rachel does, but I desperately want to serve a Master. I know that you will not be the Master that I ultimately serve, but I hope that you will serve as my Master for the duration of my stay.
Rachel has told me about your playroom, though she has not been able to show me, and I hope that you will use everything in the room on me. I promise that I will deny you nothing that you ask of me.
If you choose not to accept Rachel's gift, I will understand completely. You may simply send me home at any time.
Yours in Servitude
Anne
I smiled at the girl in the box and said, "Wait for me a little longer." Then I replaced the lid, went to Rachel and said, "Come with me!"
Rachel was nervous as I took her upstairs to her bedroom. "What did you think that you were doing?" I asked her.
"I was giving both of you a present," she said, showing signs of nervousness. "I was giving her the Master that she wanted, and I was giving you a new slave to play with for a while."
I counted slowly to ten, determined not to blow up. Then I said slowly, "Tell me everything about this girl."
Rachel told me everything that she knew about Anne. She explained about the girl's parents and Anne's love for pain. She described some of the sessions that she had with Anne, and recounted the feelings that Anne had told her she had.
When Rachel was done, I just shook my head and said, "Rachel, I am very disappointed with you."
"Why?" Rachel asked in surprise. "I thought it would be a good present for both of you!"
"Rachel, I already have two beautiful women that do whatever I want," I told her. "Dealing with Anne will be more work than fun for me. But I cannot tell her that I do not want this, because despite what she wrote, she would be devastated.
"I think that you were correct about what would happen to her in the future, but if you had talked about this with me, we could have come up with something that would solve the issue. As it stands now, you've painted me in a corner. Did your mother even know about this?"
"No," Rachel said, tears starting to drip. "I told her it was a secret, and she left the room so that I could sneak Anne in."
I sighed. "Here is what we are going to do," I told her. "I am going to go back downstairs, and I will use Anne as a slave for the next three days. You, on occasion, will be involved. But as punishment for what you did, you will not be allowed to cum as long as Anne is here. Do you understand?"
"Yes, Jeff," she cried. "I'm sorry. I was just trying to help!"
"I understand," I told her. "But you did mess up, and you will be punished. Now clean yourself up, and we will go down and deal with Anne."
I went downstairs and reopened the lid to the box. Anne was looking at me fearfully. I held the letter up to her face and asked, "Did you write this?"
She nodded.
"Did you mean everything in this letter?" I asked.
She nodded.
"You want to be my slave for the next three days?" I asked.
She nodded.
"Do you understand what that means?" I asked.
She nodded.
"You will do everything I ask, no matter what it is?" I asked.
She nodded.
"I will fuck you in your cunt, your ass and your mouth, and I will not be a gentle lover," I told her. "Is that what you want?"
She nodded.
"Don't you want to give your virginity to someone you love, someone that will guide you through it gently?" I asked.
She shook her head violently.
I reached into the box and ripped the tape off of her mouth. She screamed briefly from the pain.
"Ask me for what you want," I demanded.
"I want to be your slave," she said. "I want you to take all my cherries. I want to serve you."
I reached into the box and pulled her up, slinging her over my shoulder. I carried her over to an ottoman and laid her face down on it. Her hands were still bound, and had to be uncomfortable stuck under her stomach. I knelt behind her, my knees straddling her bound legs and I opened my pants. Rachel walked back into the room just as, with no warning to Anne, I shoved my cock all the way into her defenseless pussy.
Anne screamed as I ripped through her hymen and then started pounding my cock into her. I'll give her this: she was well lubricated. Being tied up in a box for hours must have been a real turn-on for her, because she was very wet, but she was also very tight.
Her scream turned into groans as she kept repeating, "Yes, master. Yes, master." Her virgin tightness, combined with her bound thighs squeezing my cock led me to cum fairly quickly, but Anne was cumming with me.
When I was done, I pulled out and called Rachel over. I pointed to my blood-tinged cock and said, "This was your idea, clean me off."
Rachel made a face, but she took my cock into her mouth and cleaned me all off. When she was done, I told her, "Now clean Anne out." That was hard, because of the way that Anne was bound, but Rachel was able to worm her tongue in.
While Rachel was cleaning out Anne, I went over to Jess and Michelle, who were still looking at me with shocked expressions, Michelle more so than Jess. I explained to them what I had done, and why, including my conversation with Rachel. When I was done, they understood.
Rachel had finished cleaning out Anne, but I said, "I didn't tell you to stop! Keep licking her, and while you're at it, get her asshole wet and loose too!" I had never asked her to do that before, but she did as she was asked.
I let her continue for a few minutes, the only sound in the room made by her tongue's wet lapping and Anne's soft moaning, which was getting louder by the minute. Finally I announced, "I've talked to Rachel and explained to her what she has done wrong. As her punishment, she will not be allowed to cum until we send Anne home. Jess, on the other hand, has behaved so nicely that the next few days will be a reward for her."
Jess looked happy at that, and I turned to Michelle and said, "Sis, things are going to get quite a bit more intense over the next hours. You can stay, if you'd like, but if you do, please don't interfere."
"More intense that what you just did?" she asked.
I guess Anne's apparent rape was pretty intense. Nonetheless, I said, "Yes, it will get more intense than that."
Michelle thought about it, then said, "I guess I'll stay, and I can always leave if it gets too intense. Will I just be an observer, or a participant?"
Mmmmm, now that was an excellent question. I hadn't planned for any of this, but it could be very interesting with sexy Michelle as a participant. I gave it a little more thought, and then I said, "I'll tell you what. You decide if you want to be a participant or an observer. If you are an observer, you may stay until you become uncomfortable, and then you may leave. If you decide to participate, however, I will give you a safe word. I will treat you as I would the others, but if it becomes too intense, you may use the safe word. If you do use it, however, then you must leave. You cannot change from a participant to an observer."
"Can I change from an observer to a participant?" she asked.
That was an interesting question, and I gave it some serious thought. In the end, however, I told her, "No, I don't think so. I will be building things up, and if you start as an observer and then just jump in, I don't think it will work out. You have to decide now."
Michelle was very nervous, and she sat there for a long time, looking around at the others. Again, the only sound in the room was Anne's ragged breath and Rachel's moving tongue. Finally Michelle said, "I want to be a participant."
I smiled evilly and gave all the women their safe words. Then I said to Rachel, "Knowing you, you've prepared everything. Does she have a collar?"
Rachel nodded, and I told her to go get it. I also had Jess go get her collar and Rachel's, as well as a spare. Rachel came back and showed Anne her collar, which caused Anne to gasp. Rachel brought it over and showed me the tag. On one side it said, 'My name is Slave Annie' and on the other it said, 'I belong to Master Jeff'.
"Does anyone ever call you Annie?" I asked Anne.
"No, Master," she said.
"Then that will be your slave name," I said. "Jess, please go remove the tape from Annie. Rachel, help Michelle on with her collar."
Jess cut off the tape from Annie, and then tried to help her put her collar on.
"Please, sir, will you put the collar on me?" Annie begged. I smiled and beckoned to her, and she crawled over to me. I placed it around her neck, and she came! Spontaneously, with absolutely no physical contact.
"You really want this, don't you?" I asked.
She nodded and whispered, "Please don't be a gentle Master."
I sat back, looked around the room and thought, 'How did I ever get myself into this?'
The first woman that I approached was Jess. I removed my shirt, then I reached for her and pulled her into my arms. I ran my hands up and down her back, stroking her neck and cupping her ass as I kissed her passionately. When I'd had enough, I helped her down onto her hands and knees in the middle of the room.
Next I took Annie in my arms, and repeated the process. It suddenly struck me that I had fucked this girl, taken her virginity, and this was the first time I held her, the first time I kissed her. I loved the way her big boobs and hard nipples squashed into my chest. As I was holding her I ran my finger over her asshole, dipping just the tip of my finger in, teasing her with what was to come. By the time I was done, she was panting and could barely stand, something that was no longer required as I knelt her next to Jess.
Rachel was next, and I felt the tension in her as I kissed her. As I fondled her ass and ran my fingertips up her spine I whispered, "You messed up, Rachel, but take your punishment like the good slut that you are and all will be forgiven." After I said that, she attacked my mouth with her tongue and tried squeezing my whole body into her. When I felt that I had reassured her enough, I placed her on her hands and knees next to Annie.
When Rachel was on the ground, I turned to a scared looking Michelle. "Well, well, well, big sister," I said. "It looks like you are the only one left."
I crooked my finger at her, and she walked over to me hesitantly. I pulled her body into mine, feeling her beautiful tits on my chest. I looked into her eyes and asked, "Are you ready for this?"
"I'm not sure how far I want to go," she told me.
"That's why you have your safe word," I told her.
"But then I have to leave," she said.
"It's incentive not to use it," I said. "Your mama didn't raise no dummies!"
Michelle brought her face forward and kissed me, and it was not a sisterly kiss. I filled my hands with her sexy ass, lifting and separating her ass cheeks, brushing up against her perineum, teasing, but not committing to anything.
When I had my fill of this new experience, I had her kneel down next to Rachel. Then I stepped back and looked over the visual feast in front of me. I don't believe in God, or Karma, but something had smiled down on me, because I certainly hadn't done anything to deserve this.
There they were: four sexy, beautiful asses, staring me in the face, wiggling enticingly in front of me. I had set them up with their legs slightly spread, so I could see their pussies peeking out at me. I sighed as I walked around the side, taking in their backs arched sexily, their tits half visible hanging down. I continued around to the front and pulled a chair up to examine them.
They were all looking at me, watching eagerly, waiting for me to do something. I could see their beautiful faces, their stretched necks, each encased in a collar, their full breasts hanging, waiting to be nibbled. I had to capture this. I went quickly to Rachel's bedroom and got her digital camera. I walked back into the room, standing first behind them, and began documenting what I was seeing. I snapped pictures from the sides, and then from the front. Michelle looked the most unhappy about my photography, but I just pointed the camera at her and said, "Smile, beautiful." She did, and I got a lovely picture of her.
Then I walked behind them and picked up the other item that I had retrieved from Rachel's room. I knelt behind and to the side of Jess and said, "This is for you, because I know that you love it." I then gave her ten hard swats on the ass with the paddle.
When I was done, Jess said, "Oh, thank you for that!"
I moved behind Annie and said, "This is because your beautiful ass begs to be spanked." I delivered fifteen hard swats on her cushiony ass, and then five more when she begged for more.
I next moved behind Rachel and said, "This is just a taste, because you are being punished." I gave her four sharp swats with the paddle, not as hard as she liked, just enough for her to want what she was missing.
Finally, I moved behind Michelle. She looked back at me nervously, but I just smiled and said, "This is so that you don't feel left out." I gave her 5 swats, but they were just love pats; the anticipation hurt her more than the paddling.
I walked around in front of them and took my pants off. I instructed them all to stand up, and they all displayed their bodies proudly for me. "Jess, go get the K-Y Jelly," I demanded. "Rachel, this slave you gave me has too much pubic hair. You know how I like my women; go get a razor, towel and water. I want you to shave her bald."
Annie looked nervous and excited as Rachel went off to get the supplies. Jess was back, meanwhile, and I had her apply the Jelly to my cock. Rachel came back just as I pulled Jess onto my lap. I turned her to face the others and lifted her so that I could position my cock at her asshole. She slowly pushed her self down until my cock was buried completely in her ass. I held her there, savoring the feel, as we watched Rachel spread Annie out and spread shaving cream over her crotch.
"Michelle," I called. "Come over here and lick Jess' pussy."
Michelle dropped to her knees and crawled over. She looked up at Jess and me a final time before running her tongue over Jess' clit. I let Jess start moving slowly up and down as we watched Rachel carefully shaving Annie bald. Jess came for the first time on Michelle's tongue just as Rachel washed off the last of the hair and cream, exposing Annie's naked pussy.
I looked down as I felt Michelle take one of my balls into her mouth. She winked up at me, her mouth full of testicle. I said, "Annie, come take Michelle's place and serve me and Jess. Michelle, it's your turn for a haircut."
"But I like my hair!" she said.
"You have two choices," I said. "You can use your safe word and leave, or you can go to Rachel and have your hair removed. If you do go to Rachel, however, she will give you five spanks on your ass as punishment for your obstreperous behavior." Michelle crawled over to Rachel and sprawled over her lap. Rachel smiled wickedly at me and gave Michelle five hard ones; these were no love taps.
When Rachel was done with the spanking, she spread Michelle out and began shaving her. Annie, meanwhile, had come over to serve us. Her tongue started in Jess' pussy, but it was quickly roaming everywhere, moistening my balls and even dipping down to my ass. As my cock pulled out of Jess' ass on a stroke, I felt Annie's head and tongue trying to get a taste. I wasn't sure that I wanted her to do that, especially as I planned to kiss her later, so I redirected her head back to Jess. I also had her slow down, so that she was keeping Jess very heated without taking her to an orgasm.
When Rachel was done with Michelle, I had her replace Annie, and I told Annie and Michelle, "Now I want you to masturbate for me. I want to see you playing with your bare twats, I want to see you bring yourself to orgasm. Why don't you think about how sexy it is watching this slut at my knees licking and sucking her own mother! I know that always gets me off, thinking about people fucking others in their own family." The last I said looking right into Michelle's eyes.
It was an amazing feeling, Jess' ass moving up and down on my cock, Rachel's tongue occasionally lapping at my balls, and two sexy women masturbating in front of me. It was like a giant feedback loop, and as soon as one of us started cumming, Annie in this case, it set us all off, and soon we were all slumped in contentment, except, of course, Rachel, who was denied the chance to cum.
Rachel got up and soon was back with cool water and warm cloths all around. She handed each of us a glass and then proceeded to clean everyone off. When we were all cleaned and relaxed, I had everyone come upstairs to the master bedroom. I had the women relax on the bed as I set a chair up near the bed. An old chair, a glue gun and a butt plug and I soon had an excellent spectator seat for Rachel.
I slathered K-Y on the plug and beckoned Rachel over. I positioned her on the chair, and she dropped down on the plug, her ass sucking it right in. I then took some rope and tied her tightly to the chair so she could barely move. When I was done, I asked, "Comfortable?"
She shook her head, indicating that she wasn't. "Good," I told her. "It wouldn't be punishment if you enjoyed it, would it?"
She shook her head and I climbed onto the bed with the remaining ladies. "Ready for round two?" I asked.
They all nodded eagerly.
I positioned Jess with her head on the pillows and spread her legs open. Then I positioned Michelle with her head toward the foot of the bed, her legs also spread, her thighs crossing Jess' thighs, their pussies a few inches apart.
"Now comes the fun part," I told them. I had Annie move into a 69 with Michelle. This gave Michelle access to Annie's cunt while Annie had her face above both Jess' and Michelle's pussies.
"Almost done," I said. I retrieved a toy that I'd had Jess purchase recently. It was a large, double-headed dildo, and I inserted it so that it connected the two women. I then took Annie's hand and wrapped it around the dildo.
"Your job," I told Annie, "is to make these two lovely ladies cum."
"Your job," I instructed Michelle, "is to give Annie some extra pleasure as she has her first ass fuck.
"And your job," I told Jess, "is to lie back and enjoy a lovely orgasm. Are you all clear on what you are to do?
"I certainly am!" Jess said in a satisfied tone of voice. The others nodded.
"Then begin," I told them.
Jess grabbed another pillow and popped it under her head so that she could see what the others were doing. Annie started moving her fist back and forth, fucking Jess and Rachel alternately with the dildo. Her knuckles kept hitting their clits, and when it wasn't she was licking at them with her tongue. I moved behind her and saw that Michelle was holding Annie's ass cheeks open as she licked at her cunt.
I took the K-Y jelly and lubed up my cock again. I knee-walked my way up the bed until my knees were straddling my sister's head and my balls were hanging in her face. I put the head of my cock up against Annie's tightly closed asshole. Michelle attacked Annie's clit, probably trying to distract her, and I shoved my cock into her. I tried using a single stroke, but her ass was too tight. My cock got stuck halfway in as Annie shrieked in pain. I pulled partially out, then shoved back in. It took a half dozen strokes and as many screams from Annie before I was buried completely in her no longer virgin ass. I rested there for a minute, and I felt Michelle licking at my balls.
After I felt she was stretched sufficiently, I grabbed her hips and slowly started fucking her. I quickly sped up and was shafting her repeatedly. I had cum twice in the last few hours, so I knew I wasn't in any danger of cumming. I grabbed Annie's hair and pulled her back. Her hand was still clasping the dildo, which pulled up and partially out of Jess and Michelle, and then she released it and it snapped back. The two impaled women gasped, as did Annie as I pulled her hair all the way back. I reached for her shoulder with my teeth and bit hard as my hand reached around and squeezed her large tit, pinching into her nipple. She screamed as she came, then she collapsed onto Michelle as I released her.
I looked down at my blood streaked cock and decided that Annie'd had enough. I pulled out and saw that Jess was moving up and down on the dildo, fucking Michelle with it. I watched as she brought them both to an orgasm. I rolled Annie off onto the side, then I went to clean myself up and bring everyone water and washcloths.
I climbed into the middle of the pile of women and we all rested. I glanced over at Rachel and saw her sitting with a glazed look in her eyes, futilely trying to move up and down on the butt plug.
After a few minutes Jess proclaimed, "You didn't cum!"
"Nope, I was saving myself," I said.
"For what?" she asked.
"For when you teach Annie how to give a good blow job," I told her. I couldn't think of anyone that I would rather have teach Annie than Jess.
Jess pulled Annie down and started to show her my cock. She quickly realized that this was the first time that Annie had seen a cock up close and personal. Jess showed her all the parts and demonstrated what it was used for and how it made me feel. She explained the most sensitive parts of my cock, and how careful she had to be of my balls. Finally, she had Annie start licking my cock, and then she worked her up to taking it into her mouth. She showed Annie how far she could go without choking, and explained how she could work on that. Then she showed Annie how two people working on a cock simultaneously could be very pleasing to me.
Finally, she was done with the instructions and she had Annie start seriously sucking me. While Annie was sucking, Jess started pumping my cock below her mouth. She told Michelle, "Feed him your tits!"
"What?" Michelle asked in surprise.
"I want Annie to get her first mouthful of cum, and Jeff sucking his sister's tits will make him cum sooner! So get your tits up there!" she demanded.
Michelle didn't look too certain about it, but I was happy to grab one of her tits in my right hand while sucking the other in my mouth. Jess was right, and it was that added stimulation, along with Michelle's moans of pleasure, that caused me to spew my load into Annie's mouth.
Jess was right there, telling Annie how to pull back a little so she could get all my cum into her mouth, explaining when to swallow and how to avoid choking. I would have been very interested in her explanation if my brains weren't oozing out through my dick. I fell back, exhausted, as Jess showed Annie how to clean any remaining cum off of my cock.
We all rested, and I almost nodded off when Jess asked, "What should we do with Rachel?"
"I have plans for her," I said sleepily. "You and Michelle stay here. Annie, help me with Rachel."
Annie helped me untie Rachel and pull her off the butt plug. We walked downstairs and then continued to the basement. I walked to the playroom door and told Rachel to instruct Annie on the rules.
"We may not open the door to this room, and when we enter, it must be with our collars and leashes, and only on our hands and knees," she explained. She pulled two leashes down and attached them to their collars. She then went down on her knees and helped Annie down as well. I walked in front of them, because I wanted to see Annie's face when she saw the room. I turned after I entered the room and the look on her face was priceless. She looked like a woman let loose in Tiffany's and told she could have anything she wanted.
"Tomorrow you'll learn what many of these things are," I told Annie. "But for tonight, you'll sleep. You want to be my slave, and a slave sleeps on the floor when they are not in their Master's bed. But you've been so good that I don't want you on the cold floor. This one, on the other hand, did not please me. Come here."
I had Rachel lie on the floor and tied her arms and legs spread eagle. "This should be a nice bed for you," I told Annie. I had Annie climb on top of Rachel, crotch to face, and tied her spread eagle as well. "You may have Rachel pleasure you, and you can pleasure her, but you must not make her cum, do you understand?"
Annie nodded.
I kissed each of them good night, turned off all the lights except a night-light and said, "Good night, ladies." Then I went upstairs to sleep between my sister and my girlfriend's mother.
Before we went to sleep, Annie asked quietly, "Please make me cum!" The angle wasn't great, but I was able to taste her dripping pussy and to give her a small cum. She licked me a little as well, but she was careful not to get me too close to an orgasm.
We fell asleep, but I awoke later, feeling Annie squirming on top of me. I didn't understand what was happening until I heard her groan quietly, "I'm so sorry!" Then I felt a strong stream of piss pouring out of her onto my face.
It wasn't her fault; Jeff had not let us go to the bathroom before tying us down. And to be fair, I had done this to my mother. So I just lay there and allowed the hot stream to spill over me. As the stream continued, I realized that the hot fluid jetting at me was turning me on to no end. It was so humiliating to be used for a toilet, and Jeff had to know what would happen when he tied us here. I was tied down here as Annie's toilet.
Annie finally finished, and I could hear the shame in her voice as she kept whispering, "I'm so sorry, I couldn't help it!" I felt bad because she was upset, but rather than just tell her it was OK, which she would not believe, I decided to show her. I picked my head up to her urine soaked snatch and licked off all the pee, as well as the warm cunt juice that was leaking out of her, and I did not stop until she had a nice strong orgasm. After she came, she quickly fell asleep, her hot breath slowly blowing on my sensitive pussy in the even pattern of someone deep asleep. It was a very long time before I fell asleep.