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.