3 comments/ 56786 views/ 1 favorites Housesittter Monday By: Croctden The week starts on Sunday Monday We both slept in until early afternoon. My cum had dried on Mary’s face leaving a shiny, sticky spot. We went and took a shower together. I had Mary stand naked in the center of the bathroom while I set the water temperature. It was just a standard sized bathtub, so we were never far apart as we let the water soak us. I found the soap and washed her. I was proficient, but not tender. I did take care to penetrate her intimate areas. She gave no reaction, pleasing me by accepting it was my right. I handed her the soap and she was tender, massaging my back and gently stroking my thickening cock. I leaned over to suckle my slave’s nipples. She winced; saying they were still sore. Silently I turned her around and pressed her against the wall. Using my foot to kick her legs out, I had her take a wide stance. I stepped up behind her, my cock tapped her against her legs and she reacted just enough to let me see her nervous shift. That was unfortunate for her because that only made me harder. I rammed myself into her unready snatch. She grunted loudly, but there was no scream thankfully. After all, I have sensitive ears. I just slammed her, forcing her against the cold tiles. She was making little mewing noises, which some part of me noticed. As I kept up my powerful strokes, Mary finally could not hold in her cries any longer. I gave a tight-lipped smile at the conquest. However as I picked up the pace it was getting easier. Remarkably I felt her cunt spasm around me before I came myself. She almost fell as she orgasmed. I grabbed her hips to get her back in position. She held herself there for me and I shot my cum inside her. Then, her duty done, she sunk to the floor, slumping over into a fetal position on the floor. The spray splashed her as she held herself and shook. I washed my hair and went back to my room to dress. Mary was very subdued when she came into the room. She smiled shyly when I raised an eyebrow at her. “You’re amazing Master, it’s just hard for me to keep up.” “How are you doing?” “I’m sore everywhere, but very content Master.” “That is good to hear.” I kissed her. She stuck her tongue into my mouth and sucked on mine as I pulled her in close and cupped her tight ass. “Let’s go get some breakfast.” It is pleasant to begin one’s day being waited on by a naked slave. I watched her nude form scurry around the kitchen making me brunch and making sure I was satisfied before providing for herself. I noted the welts on her ass had shrunk to faint red traces and asked her about it. She rubbed her ass. “Yes Master, they do not hurt as much now. The lotion helped.” “That is good to hear. You should be thankful I was careful not to break the skin.” “I am Master, although they were very painful at first. I never want to go through that again.” “You will and you will suffer worse if you are bad.” “Then I will always be good.” “That is indeed the aim my pet, but there will be times when you are whipped not for being bad, but to please me.” She looked terrified. “To please you Master?’ “Yes slave. Either because I am in a bad mood, or because I want to savor your cries of pain.” Her eyes started to tear. “Do not get upset, I will not do it often by any means. It is just the same as when you surrender you ass to me. You take hurt for my enjoyment. You will even learn to ask for it to make me happy.” “Yes Master,” she said in a small voice. “Do not worry. I know it seems unlikely now, but you will learn. All of this is far in the future anyway.” She was quiet for a while, so I read the paper whilst she sat and thought about my words. As we finished up Mary spoke up again. “What are we doing today Master?” “Training mainly. As I am only here for a week I am forced to break you in quickly. I will also do a little reading, but not much besides that. We can get another movie if you want.” She tried to keep her voice even; I purposely used language to intimidate. “What type of training Master?” “This and that. You said you were sore, so I may go light on some aspects. Is there anywhere you really hurt?” “Just my bum Master.” “Come here.” She came and I lay her across my lap. She tensed when I spread her cheeks. Her asshole was fairly bruised. I touched the edge and she yelped. I started to work my finger in. “No!! Master please!!” she cried in real pain. I worked my finger in and she trashed in agony. By the time I got my index finger all the way she was sobbing. I popped my finger out, but she did not stop crying. “Go get the lotion.” She came back quickly enough, still trying to stop crying. I patted my lap and she paused, but quickly flopped down when I shot her a look. “Spread yourself slave.” She compliantly reached back and opened her ass. I put some lotion on my hands and worked it into her. She soon stopped crying, even as I forced her ass to expand for two fingers. Eventually I gave her a slap to get her to stand up. “Your hole is a little bruised, however you will be fine later.” Her eyes were still red. “Thank you Master.” She seemed to want to add more. “Is there something else?” She looked down. “I was just going to ask you to be gentler with me. I have never had anything up my ass before.” “I will use you as I like slut. You have still to learn to live for my pleasure.” “Yes Master.” I stretched. Truth to be told I had not decided how to begin my training. “I think I want a massage.” She seemed to brighten at this reprieve and happily led the way upstairs to my room. I stripped and lay down. Mary produced some oils. “Not yet slut. From now on when we are alone you are to wear you maid’s outfit. Go put it on.” She did not seem thrilled at the idea, but put it on, after all she had been naked. I think she knew how slutty she looked. She gave a very good massage, rubbing away all my stiffness. She worked my back over completely. “Do you want me to do your front Master?” “Yes, but you are not done on this side yet slut.” “Master?” “I want my asshole massaged, but orally. Put your hands behind you back and tongue my asshole.” I could feel her pause, but soon felt her tongue worm its way into me. I am not much of a fan of having my ass eaten, but it is a tough pill for a new slave to swallow. I kept her down there for a while before turning over. I had her continue on my front as my cock stood up in the air. Once she was done I had her clean up the oils. “Now I want you to use your pussy to massage my cock.” She quietly got on top of me, slowly as my cock stretched her pussy and filled it completely. She started to move but I stopped her. “Stay still, use your muscles to make me cum.” She was not used to this, but worked earnestly, slowly figuring out how to manipulate me with her pussy. Once she worked it out, she got a nice rhythm going. Her body was shiny with sweat from working so hard, but her juices rushed out of her taunt pussy. Once I was as hard as I was going to get this way, I had her rock back and forth without withdrawing any and soon filled her pussy with my seed. “Clean me off.” Clearly upset at being denied she climbed off me and started sucking. Once I was soft I had her stand at attention. “Would you like to cum?” “Yes please Master!” “Stay at attention.” Calmly I reached between her legs and started to thumb her clit. She quickly fell into meaningless noises. I repeated to scrape just the edge of her insides with my finger, and lightly pinched her folds. She could barely stand and staggered around when she came violently. Once she came down I held my hand out and she quietly licked her taste off it. “Thank you Master.” “You are going to have to work on getting better control of your muscles. That is for later however. You did not think the training would involve pleasure for you did you?” “No Master. I was afraid of what you were going to do to me.” “You have no reason to worry. You will be in pain, but pleasure too is a part of your world, and you will experience both. As I told you last night, you will be punished for being bad and rewarded for being good.” She nodded. She looked to be considering her situation, fear and lust mixed in her eyes. Slavery was taking on a new meaning for her. I rubbed her hard nipples, visible through her tight outfit. They were still a little sore and she whimpered, but pushed her chest forward. “Does that arrangement appeal to you slut?” “Yes Master, I want to please you.” I smiled and cupped her cheek. “Good girl, you are learning well.” I stepped in to kiss her. As we embraced I pulled up her skirt and massaged her bare ass. She wiggled underneath my hands. I smacked her ass and she yelped, but kissed me harder. Intrigued, I spanked her again. She cried out but shoved her tongue as far into my mouth as she could. She rubbed her body against my, writhing against me. I traced a finger along her crack, pausing at her hole. She tensed, but kept kissing passionately. Eventually she had to come up for air and I slowly rimmed her hole. She grabbed my shoulders tightly, making little cooing noises. “Does your ass still hurt?” “A little Master,” she said breathlessly. I gently pushed my finger into her asshole and she squealed. “I will let the lotion soak in a little more.” I gave her ass one last smack. She gave a yell, but kissed me again. “Thank you Master!!” I laughed. “We are going to take a break. I have some reading to do. While I am busy, I want you to work out.” She seemed to pout. “There is nothing wrong with your tight little body.” She preened. “And I want you to stay that way. When you are not pleasing me, you should work to make yourself better for when you next see me. Today this means working out. Other times it will mean tanning to get yourself the color you are all over. It will also mean shaving. Do you understand?” “Yes Master, when you do not need me, I should work to keep my body up.” “Very good.” I kissed her lightly. “Now strip.” When she complied I picked up her dress. “Do not wear you slave clothes to work out, you can wear whatever you want. Now put this away.” She took the dress and turned to go to her closest. I gave her a good slap on her ass. She jumped and cried out. She looked back at me in confusion and rubbed the pink spot on her ass. “Go work-out slave. I will find you when I want you.” “Yes Master.” ***************************** I spent the next few hours adding some more to my latest article. When I had finished a chapter I closed down my computer for the evening. I checked my watch and found it was getting to be late in the afternoon. I found my slave working out diligently in the basement. She was wearing a pair shorts and T-shirt. Her body was covered in a layer of sweat, making her skin shine. She stopped when she saw me. “Hello Master.” “You are done exercising now.” She nodded and came to stand before me. I waited, but she just stood there, then a light finally dawned and she stripped. “Get down on your knees.” Once she had I pushed her over and put her face to the ground. I walked around behind her. “Spread you ass.” She trembled slightly, but did so. Her asshole looked better and I wormed my finger inside. She shook and moaned, but I recognized them as the noises of fear, not pain. “Does it hurt?” “Just a little Master.” Her fear was clear in her voice. I was tempted to enjoy my slave, but there were others matters at hand. I gave her a good smack on her ass. She yelled, but stayed bent before me, her ass wide open. “Very good slut.” “Thank you Master,” she preened. “Come, we are going out.” I started upstairs, Mary following me to her room. I tossed her the lingerie we had bought yesterday. She put them on quietly. The stockings came a little past mid-thigh and looked great with black crotch less panties framing her pussy. The nipple less bra hid the smallness of her tits a little and called attention to how hard her nipples were. She cringed when I gave her the black half tee and mini skirt. The T-shirt called attention to her pouting nipples and a quick examination made it clear what type of bra she was wearing. The stockings ended short of her skirt, showing a small expanse of flesh. The choker necklace completed a perfect image. Mary looked to be a total slut and she knew it. A few tears started to trickle down her cheeks when she looked at herself in a mirror. “Please do not make me go out like this Master,” she pleaded softly. I stepped in behind her, sliding my arms around her waist. “Why?” I rubbed my cock into her ass. “Don’t you want to please me?” I moved one hand up and started to play idly with one of her tits. “Of course Master. It’s just that this is so embarrassing.” I started to kiss her neck. “Which is more important to you? My pleasure or your pain?” She hesitated, but spoke with conviction, “Your pleasure Master.” “Then what is the problem?” “It’s just hard to get used to, that is all.” I turned her around and kissed her, she returned with passion. “You are doing fine.” We kissed again. “Now make yourself up as you did yesterday, but this time use perfume, but let me smell it before you put it on.” She nodded and sat down. I was impressed with her perfume selection and easily found one I liked. When she was done, I had her twirl for me. Moving rode her skirt up, revealing her nether lips. She quickly pulled the skirt back down. I laughed when I realized how much she would have to be doing that. I offered her my arm and we exited her room. “Where are we going?” “We are going to drop Platoon off and get a new movie for tonight. Then we will go to dinner.” Her step faltered slightly when she realized she would be dressed this way around town and might see people she knew. I smiled inwardly and patted her on the ass. ***************************** Mary was uncomfortable in the video store. She repeatedly pulled her skirt down (not that it did any good) and stayed quietly close by me. I took my time, wandering around the store, not so much to show my slave off as to find a good movie. I am a stickler for quality. In the end I selected “Butch Cassidy and the Sundance Kid.” I chatted with the guy behind the counter for a while when I noticed him giving Mary the once over. She just looked down and blushed. Once we were in the car I asked Mary to recommend a restaurant. I had my favorites, but I wanted to go to a place she would run into some friends. She mentioned some steak house chain by the mall. I did not think running into friends even crossed her mind. The place was jam packed, but a small amount of green got us a table. Our table was on the edge of the main area, and Mary’s attire was hard to miss. We were just beginning to eat (I had again kept conversation light) when I noticed Mary frown. I looked over my shoulder to see a group of girls who appeared to be the right age group. “Friends of yours?” She nodded. I kept my thoughts to myself, but I could track their movement in her eyes. First they went to their table. They stayed a while, to order I guessed, but then some of them made their way over to us. I was impressed with how well Mary hid her displeasure. I was introduced and acted gentlemanly. They asked what we were up to, clearly looking to invite us along, but not flinching when told we were going to spend the evening in. I just caught one of them winking at Mary. They told her to get in touch, it had been to long. Even a social misanthrope such as myself could tell they wanted details about me. I filled it away in my memory. They shortly left when their meal came. “How close are you to them?” She shrugged, “We have gone dancing a few times. I talk to them fairly regularly.” “Who are your close friends?” “Those three girls from the movies last night, why?” “Just curious about you life is all.” She seemed pleasantly surprised, which was why I had lied. “I am a human being after all.” She laughed. I subtly questioned her some more about her life on the way home. She was more then happy to talk about herself. I got a rough idea of how her life had been going. She had some friends up here, but most of her exs were down in Boston. She told her friends all about her life, including her current quest for a boyfriend. She told me she was very happy to be involved with me. I stroked her leg and started to play with her pussy a bit as we talked. She shifted repeatedly and placed her hand on mine to try to get me to stop, but did not attempt to pull me away. I just toyed lightly with her, distracting her, but not letting her get too far. I asked her a fair bit about what she had told her friends about her life, specifically her sex life. She admitted they told each other nearly everything, and told me all of their stories along with her own past. I moved my finger down and began to rim her asshole. She whimpered pleadingly, but kept her legs spread. “So tell me what do you want to do tonight?” “Umm, it’s really your call.” “What would you do if I was not here? What had you planned to do when you first heard I was coming?” “Well I would normally either go dancing or have some friends over to hangout, watch a movie, you know.” “And what were you thinking about doing once you knew I would be here?” I gently penetrated her ass with the tip of my finger. She raised her hips off the seat. “Uhh! I don’t know, I was thinking you might join us.” “Are you telling me the truth?” I ran my thumb over her clit and popped it into her pussy, at the same time pushing my finger up to the first knuckle in her ass. I started to slowly piston my fingers in and out. “Ah! Ah! Ah!” She grabbed my hand and held onto it, but did not try to pull it away. “I was thinking maybe we could get together.” “How were you planning to do that?” “I was going to -nnaghu! Come on to you.” “Were you planning for me to catch you yesterday?” “No! Unh! I got turned on when I caught you looking at me legs, I couldn’t Ohnu! help myself.” “Did you want to be my slave?” I started to pump my fingers in unison and Mary doubled over. “AHH!! No, but I want to now.” I pushed my fingers in and stopped, leaving her twitching. “Why?” “Because I want to please you Master. I love you. I’ll do anything for you.” We pulled into the driveway and I stopped. I slid my hand behind Mary’s head and pulled her in for a kiss. I pulled my hand out and gave it to her to suck clean as I drove up to the house. Once inside I ordered Mary to go change into her maid’s outfit. I slipped out of all my clothes except my boxers. I got a glass of water as I waited. Mary came back down shortly. She was glowing and her nipples stood out prominently through her dress. “Get down on your knees.” She knelt before me. “Take my shorts off.” She reached up and grabbing my boxers around the waistband dragged down, scrapping her fingers along my legs. I kicked them away once they were down. My cock stood straight out, pointing at Mary’s face. I rubbed my tip over her face, circling her mouth. She looked up at me in expectation and stuck her tongue out in an attempt to lick my head. “Do you want something?” “Please let me suck you off Master!” She was getting hot. “Will you do a good job?” “Yes Master, I will give you a great blow job!” “Very well.” I rested my cock on her lips. She took me softly in her hands. She started to kiss and lick my cock, slowly covering it with her saliva as she worked her way down to my balls. She really worked me over well, jerking me off as she sucked my balls. She pulled back and started to massage my balls. She opened her mouth and rested my head on her tongue, looking up at me waiting with devotion. “Would you like to have my cock in your mouth?” She smiled and nodded without letting my cock fall from her lips. “Show me that you are a good slave.” She pulled my head into her mouth and sucked on it, running her tongue all over my tip. Then she started to take me into her mouth. Running her tongue along my cock as she sucked it. She took me to her throat. She looked up at me and swallowed my head. I stroked her head and she let my cock slid down her throat. She was mewing as she went deeper, but kept going until her face was buried against my body. She looked up at me for approval with her brown puppy eyes. I smiled down at her. Housesittter Monday “You are doing a good job.” Her eyes lit and she slowly pulled back, slathering my cock as it exited. She held me in her hands and jerked me off. “I love you Master.” She went back down on me, deep-throating me several times before I felt my sack start to boil. I pulled out. “I am going to cum soon slave, do you want it?” “Yes please Master.” She rubbed her face against my balls, kissing and licking them. “Give your cum to your little slut. I need it so much.” “Are you sure you deserve it?” “Yes Master, I’m trying so hard to be such a good slave for you. I’ll do whatever you want.” “Okay then, but do not waste any of it, or I will be upset.” She nodded. She took my head into her mouth and began to suck on it. At the same time she took my cock in both of her hands and started to jerk me off. I started to cum furiously and Mary struggled to get it all down. I forced my cock deeper into her mouth unexpectedly and she gagged, spilling some of my cum out onto the floor. She recovered quickly, and expertly sucked me dry. “You like the taste now don’t you?” She blushed, “No, Master, I just like to please you.” I gestured to the floor, “Then finish up.” Mary frowned, but went scoop it up. “No hands.” She shivered, but bent over on her hands and knees and lapped it up. She knelt before me. I kissed her on the forehead and she smiled. “You gave a good blowjob slave, but you let me down by spilling my seed.” “But-” “Silence!!” Mary looked alarmed. “Go get the crop.” She burst into tears and fell to my feet. “Please no Master! I’m sorry! It will never happen again. I swear! Please Master, have mercy!” “I have been gentle with you up to now, but you must learn to be a proper slave. Now go, the longer you delay the angrier I will be.” Sobbing, she hurried upstairs. I put my boxers on and sat down on the couch. Mary had calmed a bit when she got back down. She handed me the crop. “Lie down across my lap.” She paled but did so. “Pull your skirt up.” She started to cry, but pulled her skirt up to her waist, exposing her ass. I put the crop down on the end table and started massaging her ass. She shook as she cried quietly. I spread her ass and pushed a finger against her asshole. She moaned, but I pushed it all the way in. I started to fuck her ass with my finger, and she lay there taking it, moaning and squirming. I start to fuck her with two fingers and she started moving as she grunted in pain. “How does this feel?” “It hurts some Master.” I pulled my fingers out and smacked her on her ass. I did not hit her hard, but she yelped loudly. I smiled at the obvious proof of her fear. I started to rub her ass some more, and it reddened delightfully. Mary was too tense to enjoy it, but was a little wet when I rubbed her pussy. My cock started to stir at this image of submission before me. I picked up the crop and rolled it over her ass. She made soft noises in fear. “So tell me slut, how many spankings do you think you deserve?” “Master?” “You spilled some of my seed, what do you think is a fair punishment for that?” “Five?” I laughed. “No, this is much worse than that.” “Ten?” “I think it was a little bit worse then that, don’t you?” I traced the end of the crop down her crack, coming to rest right on her asshole. Mary struggled to control her voice. “Twenty?” “I was only thinking fifteen, but perhaps you are right, twenty it is.” I smiled to myself when she slumped. “Do you understand why you have to be punished?” “Yes Master,” she squeaked. “I could just give up on you.” Her head came up in fear. “Please no Master! Punish me to make me a better slave for you!” she begged. “Very well, but you must try to do better in the future. Now after each stroke I want you to count it, thank me, and ask for another, is that clear?” It took her a moment to get a “Yes Master” out. CRACK!! Mary jumped and howled at the unexpected blow. She struggled to get air. “One, thank you Master. May I please have another?” CRACK!! She was ready for it, but still yelled and squirmed. “Two, thank you Master. May I please have another?” She was crying already. She took all twenty, her body shaking as she cried by the end. Her ass was a mass of bright red welts. I started to rub her and the welts receded, but her taunt ass kept its color. She did not stop crying and winced when I squeezed her cheeks. “You did well slut. You are on the road to be a good slave, I am proud of you.” Her head came up. “Really?” She asked through her tears. I smiled down at her. “Yes, you submitted very quietly despite the pain.” She beamed, “Oh thank you Master!” She brushed a tear from her eye. “It hurt so much I was not sure I could do it, but now I would not trade it for anything. But my poor bum will never be the same.” I kissed my fingertips and brushed them to her lips. She smiled and sucked on them. I gently began to probe her dry pussy and she spread herself. “What do you want to do now Master?” “What do you think we should do?” “Whatever pleases you Master.” “What if whipping you pleasures me?” She swallowed but rolled and presented her abused little butt to me. “You own my ass Master, my pain is nothing, please use me.” She was resigned, but totally honest. I stroked her ass. “Please whip me Master.” I pulled my juice-covered fingers from her pussy and rimmed her asshole. “Please ass-Nnngh” she groaned as I pushed my finger all the in. “Please fuck my ass Master.” “Mary do you remember this morning when I had you practice using your muscles?” I pushed a finger from my other had into her twat. “Yes Master?” “It is time for you to train some more.” She nodded and earnestly went to work. It took her a while to figure out how to do her ass, and longer for to get used to doing both at once. My finger in her pussy gave her real trouble, it was not big enough for her to manipulate. She struggled for a while, before finding the right way to tug. She got herself going, but my finger was too small for her to get herself off on. She worked up quit a sweat and balled up her fists in frustration. Eventually I pulled out. “You are getting better, but it will take lots of practice.” “Anything for you Master.” My cock stirred at her total submission. She felt it and rubbed her crotch against it. “May I service you Master?” I smiled and patted her head. “Stand up.” She did, her skirt bunch up at the waist, showing her soaking pussy. I stood and slipped my boxers down. Mary visibly reacted, still not used to seeing my meat. “Get on all fours on the couch.” She quickly did my bidding. I teased the edge of her pussy with my cock. She kept leaning back to try to get me inside her and whimpered when I denied her. “Please,” she whispered. “Hmm? Tell me what you want.” “I want you to fuck me with that marvelous cock. I need it so bad. Give your little slut your cock Master.” She wiggled her beat red ass at me. I pushed my head into with a pop. She groaned. “Thank you Master!” she cried, “use me like the fuck-toy that I am!!” I slammed all of it into her and she howled. She kept yelling as I slowly pumped her. Eventually she stretched enough to take me without pain. She loved it and went wild, chanting my name and bucking back against me. I paused. Mary looked back in confusion. “Master?” “You may not cum until I tell you to slave.” “But Master-” “If you cum before you are allowed you will be punished much worse then you were just now, is that clear?” Her eyes got wide in terror. “Yes Master.” I started to pump again. Mary held still, desperately trying not to cum. I smacked her ass and she yelped, still very sore. “Do not stop. Never put your punishment ahead of my pleasure.” She immediately started to writhe against me, using her newly trained internal muscles to pleasure me more. I stroked her ass as I pumped and pulled her cheeks apart. She tensed up as soon as I did. I rimmed her gently and slowly worked my finger in. She did not protest as I buried my finger. I started to rub my cock through her membrane. She cooed contentedly. “Do you like that slut?” “Oh God Master, it’s incredible!!” “If you know what is good for you, you won’t cum.” She shuddered in fear. “No Master.” I continued to use Mary, intending to make it a long, rewarding ride. Training a slave is a pain and I deserved some rewards too. “Would you like a second finger slave?” “Please no!! It will make me cum Master.” I slide a second finger next to the first and rimmed her gently. “Are you sure?” She groaned as I pounded her. “Oh god! Oh god!! Please- Fuck!!” I wormed a second finger into her tight ass and started to fuck her hard with my two fingers, pushing them in on the pull out of my cock. She yelled some indiscriminate sounds. “How does that feel?” “Oh Master it hurts, but it feels so good too!! Don’t stop, it hurts so good!!” I spanked her with my other hand, timing it with the pumps of my cock. She moaned as pain mixed with pleasure, but chanted, “Yes! Yes! Yes! Yes!” I started to get close. “I need to cum Master!” “No!” “Please Master I can’t hold it!!!” “Don’t you dare cum slave!” She trembled as she tried to hold herself back. Her shaking sent me over the edge and with a growl I came in a fury, my cock leaping everywhere and shooting its hot load. This triggered Mary who suddenly froze, trying to keep herself from cumming. I drove my fingers into her ass and gave her a good spank at the same time. Mary gave a banshee cry as she came. It was too much for her taunt little body and her limbs gave out as she sank to the couch. With pulling out I picked up the crop and waited until she stopped twitching, before bring the crop down in a vicious snap. “AAAAAAHHHH!!!!!” Mary screamed. “Get back on all fours bitch!!” I managed to get two more blows in before she got back up, sobbing and shaking. I admired the three throbbing red marks as I pulled out. I still had my touch. I put the crop between Mary’s cheeks, smiling at her hissing when I pushed it against her abused backdoor. “Hold it there unless you want to be in even more trouble slave.” “Please Master, I could not hold it anymore! Have Mercy!!” She wailed. I moved in front of her. “No excuses! You disobeyed an order and now you will be punished.” I stuck my cock in her mouth. “Clean me.” She sucked me in earnest, desperately trying to please me. Once I was clean I ordered her to stand up. “Go upstairs, lie face down on your bed and wait for me. Don’t move and don’t let the crop fall out if you know what is good for you.” *************************** I decided to let her worry a bit. I flipped on the TV and caught the end of some bad comedy movie. After about forty minutes I made my way upstairs. To my surprise she had not closed the door to her room, so I was able to quietly slip in and observe her. She was lying as ordered, but with her face in hands. It was fairly clear she had been crying. I took hold of the crop and gently pulled it from between her cheeks. She started and looked up surprised to see me. “Are you ready to be punished?” “Yes Master.” “Do not just say that, we will be a while. If you need to powder your nose or get a drink of water you may go now.” She nodded and hurried away. I prepared the room for Mary’s punishment. I did not have any specific plan, nor was I really upset with her. Mainly I wanted to break her in to the different types of punishment. This was a part of her slavery she may not have thought about. Also she needed to learn to follow my orders precisely. I had laid out all of the purchases from the previous day on Mary’s bookcase and she stopped dead in her tracks when she saw them. The air of foreboding was heavy. “You are going to be punished slave. It will be more painful than anything you have ever experienced before. Remember that you are suffering to learn to better please me. You must put everything else aside for my pleasure.” She took a breath and spoke with conviction, “Yes Master.” She had resigned herself to being what she wanted. A sex-slave. From now on while I would have to train her, her submission would be complete. “Strip.” Without second thought she peeled her maid’s uniform off. “Get on the bed on all fours.” She did and looked back at me. “Stare straight ahead.” She promptly obeyed. I considered what to do. Her will was broken; this meant I now needed to teach her the pleasure of the whip. This secession was now about my pleasure. I stroked my slave’s body. Working up her legs I tested her pussy with my finger, she barked with fright, but was wet. Moving around behind I teased her asshole and she shivered. I moved up her body, squeezing her nipples and rubbing her back and neck. She was shaking and making soft cooing noises when I popped my finger into her mouth. She sucked it greedily. “You are beginning to like being a slave aren’t you Mary?” “Yes Master.” She blushed faintly. “What do you like about it?” “I-I like to please you.” “You are a little slut aren’t you?” She winced at the word. “Yes Master.” “Say it.” “I’m a total slut, I’ll do whatever you want.” “Good girl.” I patted her ass. It was pleasantly tight under my hand, so I began to squeeze and rub my slave. She shifted slightly, still sore from her spanking. I went over to the assortment that I picked up yesterday. She had already felt the crop, so I picked up the paddle. I rubbed the smooth wood over her ass and just caught the sound of her whimper. “Do you know why you are going to be punished?” “Yes Master. I came.” “No.” I just tapped her ass with the paddle, but her tension made her yell. “It is fine if you cum, when you have permission. You are being punished for disobeying orders. You are my slave, you do what I say no matter what.” “Yes Master.” She sounded sullen. “We could just always end this if you do not feel up to living for my pleasure.” That got quite a reaction. “No, please no Master! I love you so much!” She stuck her ass up towards me. “Whip me Master! Make me yours!” There was considerable terror in her voice. I stroked her a little. “It is okay slave, I will keep you.” I leaned in and kissed her on the mouth. “I love you, now be strong for me okay?” “Yes Master.” She braced herself; she would take anything to please me now. “Now Mary, I am going to give you the paddling of you life.” Later she would learn to take more. “I do not want you to scream.” This was mainly to spare my ears, although I doubted that someone so new to the lifestyle could do so. “I’ll try Master.” “That’s a good girl.” I pulled my arm back and let her have it. She grunted in pain and wobbled, but stayed up. I started in on her, whacking again and again until my arm started to tire. 53 times in total. My slave was groaning and crying, her body shaking, but she kept her ass, now bright red, up. I was impressed with her will, she never really screamed once, even thought I could tell she was in agony. I put the paddle down and kissed her butt, pleased at the heat that was rising from it. “You did well.” She turned and looked at me through tears filled eyes. “Really?” I nodded. She smiled and hugged me tightly. “Thank you Master! It hurt a lot, but I would not let myself cry out, I wanted to make you proud.” I lightly kissed all over her face. “I am proud, you are becoming a very good slave.” She squealed in happiness and wrapped her little body around mine. I slid a hand down and pushed a finger inside her. She was a little wet. I looked up at her. She blushed slightly. “That’s not from the spanking. It’s when you told me you were proud of me.” Perfect. I kissed her and she responded with everything she had. I cupped her ass and she groaned but kissed me harder. I squeezed and she yelped but kept kissing me. I smacked her ass and she cried out, but quickly returned her lips to mine. I slid a pair of fingers into her pussy and found her very wet. “It’s you kissing me that’s doing it.” She got out between kisses. I started to pump my fingers and she went wild, running her body up and down mine. I stopped and she regained some control. “Massage my fingers.” She went to work diligently, holding onto me, but working her muscles to tug and push at my fingers. “You are going to have to become adapt at this if you want to be a good slave for me.” She responded with increased vigor, rolling my fingers around inside of her. She was getting good. I pulled my fingers out and slid one in her ass. She groaned but went to work right away again, pulling on my finger with her ass. I slipped my fingers out after a few minutes and kissed her passionately. She looked at me with surprise when we came up for air. “You are becoming a very good slave.” I explained. It was true too. She started to cry and kissed me back. “Thank you Master! I want to please you so badly!” Her tears began to make my shoulder wet. “I need you, I love you so much!” “It’s okay baby, I love you too, and you are pleasing me by working so hard at being a slave.” She smiled and cried and kissed me hard again. I owned her mind and soul along with her body now; I would not have it any other way. “I will always love you and keep you with me. I will always own you and protect you.” She broke our kiss and laid down back on her back, pulling her legs up and open, exposing both her holes. “I am yours Master, enjoy me.” She lifted her pussy off the bed towards me. I leaned down and kissed one of her thighs, her whole body trembled. “You may cum when you want slut, but remain quiet and don’t move.” I kissed her pussy and she made a small noise, I looked up to see her biting her lip. I waved a finger at her, cautioning her, and she nodded. I placed my mouth right over her hot hole and French kissed her. I started to fuck her with my tongue and her juices started to pour out. I eased back and just kissed around the outside of her lips. Her labs were incredibly puffy and her pussy opened, searching for more. I ran my tongue around her clit making it jump to attention. She was close. I slipped a finger into her and once it was wet pushed it into her ass, slowly pumping. I devoured her box, using my tongue to massage her G-spot. Her walls contracted and she started to cum. I grabbed her clit between my lips and pulled. She screamed as load as I have ever heard anyone scream, her body rocked and she snapped her legs shut over my head. As she writhed in the pleasure of repeated orgasms I rammed my finger far up her ass, she froze in mind numbing pleasure and fainted. I had expected that. It was late and I took a quick shower before lying down next to her in bed.