Housesitter Sunday

She fell down before me. I put a foot out. She hesitated momentarily, but kissed it. “Thank you Master.”

“Stand up.”

She stood, fear in her eyes, not knowing what was next.

I kissed her, her lips parting instantly. “You did well slut. What did you think of your first punishment?”

“It was horrible.”

“Turn around and let me see.”

She turned to show me her abused little ass. I rubbed it gently and she cried out. “Please Master!! It hurts so much!”

“Sorry.” I sat down on her bed and scooted back until my back was against the wall. “Come here.” I had her lay across my lap. She seemed to blush slightly at the position. I licked a finger and gently traced the outline of her welts. She whimpered slightly. I slid the finger into her. She whimpered more as she was dry. I continued to probe her depths and her whimpers soon became ones of pleasure. She moved underneath me, as I handled her easily. She let out a soft cry as she came. Her body could take no more and she melted onto the bed. I kept fingering her, giving her the most pleasure I could.

She relaxed in a sleepy state. I covered my hand with her juices and spread her cheeks, slowly inserting a finger into her asshole. Her head came up when she felt my finger against her sphincter. She shifted repeatedly as I kept bringing more of her cum up to her ass, making it very slick.

“Master?”

“Hmm?”

“What are you doing?”

“I am lubing you up.”

Her body became instantly tense against me. “Are you going to assfuck me?”

“I am thinking about it.”

“Even after my punishment?”

“Mary,” I began, “you are going to have to give me your anal cherry sooner or later so it may as well be now.”

“But, my bottom is already so sore!” She pleaded.

“Don’t you want to pleasure me?”

“Yes, it’s-” I popped a second finger in her and she squealed. “I, umm…” she trailed off. Tears started to form in her eyes.

“Don’t cry Mary. You have to learn to be a good slave. You have to live for my pleasure, regardless of your pain. Do you understand?”

She sniffled and nodded. I stroked her hair and she smiled lightly despite her pain. She turned to watch my face as I forced her ass to expand for two fingers.

Once I had done this I turned to look back at her. “Now you need to lube me up.”

She nodded and got up on all fours. She took me in her mouth and started to suck on the end. “You better go all the way down; I am going to put my full hilt into you.” She looked up and stared into my eyes looking for mercy. She kept looking at me as she forced my cock all the way down her throat, her lips resting on my balls. Once she had me fully erect I pulled her face up for a kiss.

We both stood up. She bent over the bed before I even asked her. I rubbed the back of her neck, “good girl.”

I stepped up behind her and placed my tip and at the edge of her hole. She whimpered piteously. I start to press my head into her. She groaned, but stayed still. With a soft pop, I got my tip in her. She panted and I paused to let her collect herself. “Do you want this?”

“Yes Master, please fuck me up the ass.”

I pushed into her slowly, but she still burst into tears. She stayed still for me though. I stopped halfway in. “Do you want me to stop?”

“Please no Master, fuck my little ass. I want you to be the first man to fuck me up the ass.”

I rammed home in one fell swoop. Mary shrieked and fell onto the bed. I kept myself all the way in her. She sobbed for a while and then I started to slowly pump her. She got back up. She could only manage moans of pain, which became grunts as I sped up. She was crying and struggling to stay up with each thrust as I kept pounding her virgin ass. Finally I felt my balls tighten and I slammed her with all my strength, she screamed and fell on the bed. She stayed there, sobbing softly as I finished cumming in her ass.

I pulled out of her slowly, causing her to squirm. “Clean me off slave.”

She turned quickly and knelt before me. “Please Master, don’t make me do that, not after you have been in my ass.”

“Now slave.”

Weeping she sucked my cock dry, gagging at the taste of her ass, but still licking all of it. She dried it off with her tits. “Good little slut.” I had her stand up and kissed her again. She came happily into my arms. I held her. “Are you okay?”

“Yes Master,” she looked so fragile, “but my poor bum is on fire.”

“Turn around.” She did so. “Spread yourself.” I looked at her bright red hole, my cum dribbling out of her. I touched the rim a few times; she gave a sharp gasp of pain for each touch.

“Go take a shower. We still have to go out yet.”

**************************

She was subdued when she came back. I had already dressed. I inspected her quickly again. She blushed a little at having to stand there naked while I looked her over. Once I was sure that she would be fine I had her get dressed. I saw her frown at the clothes I had picked for her before; she blushed when she realized that I intended to watch her dress. She tried to turn away, but just me saying her name made her turn back. I smiled when she winced as she pulled on the tight leather pants.

I gestured to her makeup. “Now make yourself look your sexiest, but no perfume.” I watched her to make sure she looked the way I wanted. I told her no nail polish, but I made her go her reddest lipstick and lots of it. I made her use heavy eyeliner too. “Look in the mirror and tell me what you think.”

“I look like a slut.” She sounded upset.

“You are a slut. Now stand up.”

When she stood I unbuttoned her pants and pushed them down to her knees. While she had to just stand there, I fingered her to get her wet. Once her juices were flowing I pulled my hand out. “Use your cunt for perfume. Put it where you normally do and as much as you normally would.”

She remained still, so I took her hand and placed it on her pussy. She started to cry, but did as she was told. She put in on heavy, there was no way you could miss the scent. I stroked her face a little when she had finished. “Good girl, now get on your knees.” She knelt down, her pants still down. I pulled out my throbbing cock. Mary certain was a sweet piece of ass. She really got me going, breaking her will was fantastic for me. “We need to give you some breath spray.”

She had learned how to give head well already and quickly deep throated me. I enjoyed her ministrations as she licked, sucked, and kissed my cock form its tip to my balls. She fondled me and jacked me off, bringing me to the edge in a hurry. I stopped her. “Put your arms down and stand still. Now when I cum in your mouth I want you to hold in there, swish it around, and gargle my cum to make sure your breath smells the way it should. Do you understand slave?”

“Yes Ma-mmmph.” She cried a little as I abused her. I held her head steady while she stayed still as a pumped my seed into her mouth. She gagged a little, still not comfortable with the taste. She did as she was told, but cried some more. Once she had swallowed I had her pull her pants back up and we left.

****************************

Mary’s ass was too sore to sit so she leaned on her side as we drove to our first stop. When we got to the place I turned to Mary for a kiss.

“Hmm, you breath seems a little faint, I think you need another spray.”

Her eyes got wide. “Here?”

“Of course.” I reached and slide my hand behind her neck, pulling her head to my hardening member.

“But what if someone sees us?”

“That is not your concern. Now stop delaying or I will have to punish you.”

She reached for my fly immediately. She pulled my cock out and slurped it as fast as she could. The fear of punishment, and of being found, made her frantic to get me off.

“Slow down slave, I want a good blow.”

She slowed down, and I began to stroke the back of her head. She sucked and licked as though her life depended on it. Knowing this made it that much better, I held back as she continued to blow me and fondle my balls. Eventually her ministrations began to have their effect. “I am going to cum slut. I want you to keep blowing until you have sucked me dry, then put my cock away.” I burst in her mouth as I finished speaking, and she worked diligently until I was completely spent. She tucked my cock back in my pants and quickly popped back up. “Give it a kiss.” She leaned back down and gave it a quick peck. “No, it is your second master. You can not please me if you do not please it. Kiss my cock and let it know you love it.” She knelt down and kissed the tip sucking just the head into her mouth to tongue. She kissed down to the base. She sucked one of my balls into her mouth and rolled it a round with her tongue, following with the other. She then kissed her way back up and frenched the head again. She kissed the tip lightly again and came back up. “Good girl, you learn quickly.”

“Thank you Master.”

I zipped up, had her reapply her lipstick, and we got out of my car.

“One more thing Mary, in public call me dear, or honey, or any other romantic pet name that suits you.”

We were at a small designer store. As we went inside Mary started when she saw evening dresses everywhere.

“Why are we looking at evening dresses?”

“Because sometimes I prefer to travel in more affluent circles and you do not have a dress appropriate for those times.”

“I have my prom dress.”

“It is not refined enough. It also does not display you the way you should be.” I glanced at her in honest surprise. “Why are you arguing against getting a dress? I would have assumed you would be happy to have one.”

“Oh I am…I am just not sure that I deserve one.”

“Two points: One; you are not getting the dress as a reward. I am buying you this dress so I may adequately display you. Two; when you are done with you training you will be sure you deserve more then just one dress.”

Her eyes lit with fear and she swallowed at that.

We made our way around the store, Mary hanging on my arm. She touched the fine material and checked the price tag. Her eyes bugged out when she saw the four figure amount. “How can you afford this?”

“I can, do not worry about how.”

“What are we looking for?”

“I am not entirely sure. I will know it when I see it. Right now I am thinking about going royal blue.”

“Okay, that is not my normal color though.”

“If it does not look good on you, I will not buy it.”

I was not really interested in what she thought I looked through the stores selection. I noticed one dark blue dress that seemed odd to me. It was a full length gown, but the top was a skimpy pair of spaghetti straps. It looked as though the designer could not decided between a normal or risqué dress, and so had done both. When I examined it closely I realized it was the perfect dress. While the skirt was floor length, it had two slits up to the waist on the sides. The skirt was also stretched thin around so there would be no way to walk without revealing a lot of leg. It also had a plunging back line and a low cut front. “Go try this on.”

I knew I had been right the instant Mary stepped out. She embarrassedly tried to hide her legs from the staff to no avail. The dress clung to her, leaving nothing of the little it covered to the imagination. I called over a seamstress to get it fitted. I altered it slightly, having it push up Mary’s smallish tits into a bit of cleavage. I made arrangements to pick it up Tuesday afternoon.

“I thought you wanted a dress for affluent society- that dress does not really fit.” She said as we left.

“It does for its purposes. When we enter a room I want people to look at you and know that you are with me in order to please my cock, and not for any other reason.”

“I see.” Mary sounded small.

I paused before starting the car. “You are a sex slave Mary, never forget that. All you are is a slutty toy for my cock, and that is all.”

“Yes Master.” Mary sounded as thought she was about to cry.

I smiled to myself, knowing her will was breaking even more.

Our next stop was a small boutique. Mary followed me meekly in.

I looked through the summer dresses. I quickly found what I wanted. It was a light green mini-dress. What made it my choice though was that it was made of a light, gauzy material. I handed it to Mary.

She leaned in a whispered, “I can’t wear this without panties: my hair will show.”

This of course was precisely why I had chosen it. “Go put it on slave.”

Her face was beat red when she came back out. The thin material left no doubt were her nipples were. She was trying to coyly place her hand over her bush, but I bushed it aside with my hand. You could see the outline clearly. I had her twirl, smiling when the hem flared out to waist height. I had her put her arms straight up into the air. The hem just covered her sex. I circled her and rubbed her pussy absentmindedly. She groaned. “Please Master, someone might see!”

“Put you arms down.” She did so gratefully. “Make you nipples pout.” She blushed but pinched them, making them stand out through the fabric of the dress.

I let her go back and change, as we where under a time crunch.

I suppose the next store we went to was trendy; I just know that it had the type of clothes I was seeking. Mary was not exactly pleased with the black half tee, super tight black miniskirt with a zipper down the back, and the black choker necklace that I selected for her, but after the previous purchases she seemed relieved.

Our next stop was a GAP knock off. I bought a tiny pair of khaki shorts, they just barely covered her bush and revealed the bottom of her ass cheeks. I also got her a white sleeveless turtle neck that was several sizes to small. It almost made it to her waist, but clung to her tits so tightly I could see them quiver with every move. Again Mary was quiet out of fear of making it worse.

Our next stop was a bathing suit specialist. Here I was presented with a problem: what color? I knew the style, the tiniest sting bikini I could find, but I could not decide what would look best on my slave. Mary followed obediently cringing slightly when she saw the thongs. Then I saw a leopard print set and knew what color I wanted. I got one a size to small and handed it to Mary.

“I can’t try this on,” she whispered, “my welts will show.”

I did not particularly care, but you never know if some ignorant soul will make a scene. “Go and put it on. Then call out that you won’t come out in it and I will come and look.”

Relief spread over her. She gave me a quick peck, “thank you.” She called me a few minutes later. “I could never wear this in public,” she said as I came in. I drank in her image. The top looked fine, and looked even better after I pinched her nipples to make them stand out, smiling at her gasp. The bottom was painted on. I could see the outline of her pussy lips quite clearly. I had her turn around, and was pleased to see the string disappeared entirely into her crack. I pulled the waist band up and she cried out softly. I turned her turn back and by pulling the front had the bottom slip right inside her. She moaned. “Please, not here.”

I laughed and left, adding the suit to the costs of the day’s shopping spree in my head.

Our next stop was a mildly kinky lingerie store. Mary was not happy when I selected a black bra with the nipples cut out. She became even more upset I pick up a black set of crotch less panties with a little red bow on the front. I also picked up a pair of black fishnet garters with elastic at the top. She stared at her feet at the register.

Then we drove to the edge of town, by the industrial park. We stopped in front of a small windowless brick building. She misstepped when she saw the inside. The place was a sex shop. Leather, videos, magazines, whips, chains, dildos, were everywhere. There were a few people scattered around the small store. I nodded to the woman, behind the register. She was an old acquaintance.

“Hello Julie, how has life been?”

“Fairly well sir, and yourself?”

“Oh splendidly.” I gestured towards Mary. “Tell me, what outfit do you have for this little slut to match my tastes?”

Mary let out a little cry which we both ignored. “Mmm, that is a tough one. You have such subtle tastes.”

“Particular may be a better word.”

“Perhaps a bit of both.” Julie looked around. “Now let me think. We have some rubber dresses, but those are not really you style. There is a nurse’s outfit?”

“Probably not, but I will take a look. Where is it?”

“On the back wall. We reorganized the store; all the complete outfits are on the back wall now.”

“Well I will go have a look, thank you.”

I led Mary to the back of the store. I smiled inwardly at her looks of horror at some of the items for sale.

I discard the nurse’s outfit quickly as it was too kinky for me. I went down the whole line. I saw an option about two thirds of the way through, but continued on to make sure there was not something better. There was not, but such is life. I pulled a French Maid’s outfit off of the wall. I handed it to Mary, who looked at it dubiously.

“Try it on.”

“Where is the dressing room?”

“You don’t need one. Change right here.”

“What?” Mary looked at me in horror. “People might see!” She hissed.

“So? Look around you slave, this is a porn shop.”

“But I don’t want them to see me.”

“That is of no consequence. Now strip or I will take you over my knee right here.”

She was on the verge of tears. “Please, the marks.”

“Will let them know that you have been punished. Now strip and you better not try to hide yourself.”

She started crying. She put the maids outfit on the rack again and began to unbutton her vest. She slipped out of it, letting it fall to the floor.

“Fold it up.”

She gave a little sob, bent over and picked it up, folding it nicely and putting it off to the side. She put her hands up to her bra and looked at me, hoping for a stay of execution. I stared back into her eyes.

A heavy man in his late forties came around the corner. He stopped, not knowing what to do.

“Go on,” I told Mary.

She braced herself and undid the bra. Tears streamed down her face as she folded it up and put it on top of her vest. She stood back up and unzipped her pants, pushing them down, and shimming out of them. The guy chuckled causing her to blush. The guy whistled when she bent over to fold up the pants, causing her to shot back up.

More amusingly we then heard, “What Ricky?” and another middle aged guy came around the corner. He stopped dead when he saw Mary, “whoa.”

Mary looked mortified. I handed her the maid’s outfit and she hurriedly hopped into it. She looked good in the dress, the frilly skirt barely covering her slit. The top was less revealing, and the bra strap wrapped around her neck. I gave her the little hat which she obediently put on.

I gestured to her to spin, which she did. “Dust off the top of the rack.”

She swallowed, but stood up on her tip toes to reach. This pulled the dress up just enough to see her ass. She kept her legs clamped shut, but the guys still laughed, causing her to spin around.

“Pick up you clothes and give them to me, we would not want them to get dirty.” I smirked.

Mary cried a little silently. She knew what I want and pleasantly did so without trying hide herself. She turned around and bent from the waste, fully opening herself up to the two guys. They made rude noises. She came back and handed them to me. She looked on the verge of tears.

“Yes, this will do nicely. You can change back now.”

Her head drooped when I said this. She started when a third guy appeared. He was an old guy, wizened with white hair.

“Check this out dude, she’s gonna strip.” The first guy said.

Mary quickly slid the dress down.

The old guy whistled. “Quite a little number!”

“I’ll say.” The first guy agreed.

The second spoke to me. “You have a nice piece of ass there.”