Category: BDSM Stories

Housesittter Monday

by Croctden©

The week starts on Sunday


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.”


“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.

Category: BDSM Stories