Housesitter Wednesday

Mary had cuddled up next to me by the time I awoke, late the next morning. It had been a tiring night. Not that it was not worth it; she had been progressing well. It had been too long since I had enjoyed the comforts of a slave. I kissed her forehead and her eyes opened. "Good morning, Master."

"Hello, Mary. How are you?"

"I've never been happier. I know this sounds silly, but I think I've been waiting my whole life for you."

"So you are growing to enjoy being a slave?"

"Don't be angry Master, but no. I love you and want to be with you. But I would rather just be a normal boyfriend and girlfriend. But if I have to be a slave, I will be." She looked scared.

I kissed her to calm her. "There is no need to worry, I will not punish you for being honest."

She smiled and hugged me.

"But you do want to be a good slave?"

"I'll do anything to make you happy."

"That is good to hear, because you have more training ahead of you. And this lesson will not be pleasant."

Her demeanor changed as her eyes got a little wide.

"You have yet to see what those toys we bought yesterday are for."

She shivered in terror, but I was happy to see her crawl into a kneeling position on the bed before me. "I am yours to use Master."

I pulled her chin up and kissed her. "I love you, slave."

"I love you too, Master." Her knees parted slightly.

"But that lesson is for later, now it is time for breakfast."

God, I'm a bastard.

I sent her to workout after breakfast, while I tended to some affairs and took a nap. I checked in on my pet after waking up. She jumped when she saw me, and dove to her knees at my feet. I paused, so she suddenly and frantically began to strip, becoming entangled in her shirt.

"Stop,"

She froze.

I took her cheek in my hand and made her look into my eyes, "What is it?"

She trembled. "I'm scared I will upset you, Master."

"This is because of tonight?"

She nodded.

I chuckled and kissed her. "My love, tonight will happen no matter what you do. You are a slave, and sometimes that means you suffer for your Master. Do not worry about it."

"But it's all I can think about."

"If it helps at all, think of it this way: as your Master I can whip you at anytime without warning. At least now you can prepare yourself."

"What can I do to prepare?" She was on the verge of tears, "I wish you would do it now to get it over."

"Do not put yourself ahead of my plans," I was stern, "unless you wish to end our relationship."

"No Master! I- I will always submit to stay yours."

"Very good. You will have your lesson after my dinner party."

"Dinner party?"

"Yes, that is what I came to tell you about. I am having an acquaintance over this evening. You will serve us. You may be open about your post, as my tastes will be known."

"Y- yes Master."

"Do not disappoint me."

"I will never fail you, Master. Should I do anything to prepare?"

"Oh, we shall be dining at my yacht. I will have caterers bring food. You will merely need to serve and clean up. We shall bring your new toys as well, for afterwards."

"Yes Master."

"I thought perhaps that you had worked out enough for now and might want to unwind."

Relief washed over her. "That would be great, thank you."

"So what do you want to do?"

"Can we just watch some TV?" I nodded. She threw her arms around me to give me a kiss and then started to follow me out.

"Strip before you come down." I heard her suck in a breath, but nothing more. I went ahead, and waited for her on the couch.

She was blushing when she came down and sat on the couch next to me. She avoided my eyes. I ran my finger tips down her leg and she stiffened.

"What is this?" I asked.

"I'm not used to being naked when I'm just hanging out."

"You will need to get used to it. But I am able to realize I might be rushing you a little... do you know those khaki shorts we bought?"

She nodded.

"You can go put those on with the while sleeveless turtle neck we got at the same place."

She gave a great smile and hopped up.

She looked delicious when she came back down, as the clothes covered little and outlined what they did, but she seemed much more comfortable in them. She curled up against me and we watched a few hours of TV.

I found her viewing selections awful, but let it be, preferring instead to continue to gather more information about her life. I was happy when I could honestly say it was time to get ready. She turned off the TV and got up.

I took her arm and swung her down to her knees before me.

She said nothing as she slipped my shorts off and started licking the head of my cock. Pretty kisses worked their way down my hardening shaft. She suckled at my balls while running her hand over me, tracing a vein with her thumb. She worked her way back up, mouthing my cock and slobbering all over me. I struggled not to laugh as it tickled.

When she got to the top she reared up and hovered over me, staring down at my weapon. Her head came down slowly, her lips kissing the tip of my cock before parting to let me into her moist cavern of her mouth. She used her tongue to good advantage, swirling around the mushroom edge of my head before pressing down. My meat was full at this point and she did not get close to taking even half of me.

She started hurrying, bobbing her head down and making soft gags. Her obvious panic only surged more blood into my crotch. She was taking close to three-quarters of me now, and I was pretty sure it would take her a long while to get the rest. I was tempted, but we were on a schedule, besides she had other holes for me.

Yanking on her hair, I ignored her yell and jerked her off of me. Then I motioned for her to stand. I unbuttoned her shorts and she wiggled around so they slipped down her thighs and pooled at her feet. Two trim tan legs rose up to her pretty pussy. A trace of dew on her lips gave her away. I could see her fingers flinch; she was a little embarrassed to be exposed this way. I ran my hands down her hips and leaned up to kiss the bottom of her tummy, then motioned for her to come down for a proper kiss.

Pressing on her hips, I laid her down on the coach and slipped into her pussy in one move. I was as surprised to find her cunny was soaking, as she was to find my cock inside her, but she still made a soft noise of distress and shock at being speared. I pumped slowly, her cunt tightly wrapped around me, until she could recover. It did not take long before her juices flowed over me, allowing me to pound her for all I was worth. My manhood now sufficiently coated with her nectar, I kissed her as I pulled out. She whimpered at being denied, spreading her legs even further to offer her beet red folds to me. Instead I brushed my head down the crack of her ass and she understood.

Demonstrating how wonderfully submissive she had quickly become she pulled her legs back as far as she could to offer her anus to me. She looked a little scared, but wholly subservient. My cock twitched at the erotic vision my eyes beheld.

"I love you Mary." I just pushed my tip against her little pink, puckered hole, but it did not budge.

"I love you Master." She forced herself to open. Her backdoor relaxed as I wormed the start of my cock by. She hissed.

I was in a tender mood, so I just stroked her with the head. Then I pressed in a little bit further, letting her ring slowly expand to take me. I kept moving constantly, back and forth, so she could feel and enjoy the friction on the nerve endings of her ass. I have no idea if she was aware of it, but her chest was flush, and her mouth opened and closed with silent words. Her ass kept clenching on me, trying to draw more of me in. By this point there was not much more.

I rammed home that final length.

She shouted at being forced to give more than she was ready for.

But, after all I am a sadist.

I started slamming away at her, pulling myself almost entirely out before striking back in, as she bucked underneath me. She groaned as she struggled to ease the pain of being split by my monster buried full hilt in her ass. She looked up at me for acceptance and I kissed her deeply. She responded by rolling even further back to give me access.

I came; the mental realization of her lovingly wonderful submission was too much. My beast twisted as it spewed into her bum. I stayed in and collapsed on top of her. God, that was good.

She squirmed to try to ease the pain in her ass.

I pumped a few more times just to hear her soft cries and pulled out. Not letting her up I worked my way forward until my coated cock rested on her face. Wordlessly she began to lick it clean, frowning at the taste of herself. She was very gentle, babying her second master with great care.

Once she was done bathing my cock with her warm pink tongue, I had her pack the car and we were off. I noticed she did not strike up conversation as was her normal want.

"Nervous?"

"A little, Master. I've never been a slave in front of someone else before, let alone a stranger."

"Would you rather do it in front of your friends?"

"God, no," she blushed, "You're right about that."

"Don't fret so my love, just be a good slave for me and all shall work out."

She sighed and leaned against me, smiling.

I had her put on her maid's outfit once we arrived, and enjoyed seeing the long expanse of leg spilling out from under the white lace. She had to be careful not to totally expose her charms when she bent, as I had not allowed her panties.

I set her to work preparing the yacht for the night ahead. I went the bedroom and started laying out my tools. Mary came in, but stopped cold at seeing the instruments of torture laid out on the dresser. I'd never seen the color drain from someone's face so quickly. She looked ill.

I chuckled, "Relax, Pet, that is still several hours away."

Her eyes started to tear, so I kissed her and led her out of the room. She followed obediently, her cool little hand in mine.

"Do you want to leave?" I asked.

She shook her head, "Not if it means the end. I will always do whatever you want, I swear."

"That is good to hear."

"I love you Master, you can do whatever you want to me."

I kissed her.

"I'm just scared, and knowing its coming is horrible." Which was of course the point.

"Try no to think about it."

"I can't"

"Mary, think of it this way. At the end of the evening you are going to suffer as you never have before. There is no way you can avoid it, so it is best not dwell on it."

She swallowed.

I slipped my hands under her skirt and cupped her ass, rubbing it gently. It is so pleasurable having a slave you can touch whenever you want. She turned to give me better access. I took her arms and forcefully put them against the wall, so she would know to keep them there. She stuck her rear out for her lover when she heard me tantalizingly lower my zipper. Spreading her soft labs revealed to me that she was not very wet yet, so I rubbed my monster over her lips. I felt her whole body tremble at the contact.

That was awful early, I reflected. She was on pins and needles; adjusting to the life of a slave at breakneck speed was wearing her out. Poor thing. Her cunt juices were trickling out of her now, moistening my little friend. Slowly I started to feed her pussy, gentle thrusts with only part of my length. She started squirming, and squeaked each time I pushed a little more in.

The doorbell sounded and I slipped out with a juicy pop.

"I assume all is set?"

She was flushed, her body clearly unprepared to be denied. "Yes Master." She straightened her skirt.

"Then get the door."

I went to the living room. Mary led my guest in and I instructed her to get some drinks.

My guest smiled as my slave offered a drink. "Pretty; where did you find her?"

"She fell into my lap."

"Really. What do you call her?"

"Mary."

"That is right. You don't do nicknames, I forgot."

I chuckled- more a Mary's face at being talked about so openly than the conversation.

"How long have you owned this one?"

"Only four days."

My guest looked over Mary again. "So she's a virgin? Or did she have a previous master."

"No, she was simply your run-of-the-mill slut. She is going to learn what happens to bad girls later tonight."

"Ooo, I may have to stay for the show."

"That might be arranged."

"I bet it could be if I asked really nicely."

"Perhaps. We shall see later tonight. For now we have dinner." I rose and led my guest into the kitchen/dinning room. The sun was setting behind us, lighting the ocean a shade of orange. The view was exquisite. I sat at the head of the table and my guest to my right. "What would you like to drink?"

"I am assuming you have pre-selected a wine."

I smiled, "Good choice." I clapped my hands.

Mary entered and I directed her to the wine cabinet. Once she had served us I instructed her to get the first course.

Over dinner my guest caught me up on the latest gossip. I did not particularly care, even though these were people I dealt with on a rather consistent basis. However I pretended I did, as to not have my aims hindered in the future. I wondered how much of this Mary was picking up.

The meal was purposely light and we finished quickly enough.

"So what is for desert?" my guest asked me.

I clapped and Mary brought a serving chalice of liquid chocolate and a platter of strawberries. My guest and I began. I don't think Mary knew where this was going. My guest poured the sauce on the plate and used strawberries to scoop it up. "Come here Mary,"

My slave stood at attention by my guest.

"Let us see your breasts."

She glanced at me, but silently complied, untying the dress behind her neck at my nod.

"Mmm, not very big are they?"

My slave flushed. Mary was totally unprepared when my guest cupped her. She hurriedly stepped back.

"If you behave poorly towards my guest, our upcoming session will be that much worse." I warned.

She flinched, and dutifully offered up her tits again.

My guest stroked them and flicked the nipples. "You can act all you want slave, but your hard nipples betray you."

Mary kept her head down, but I could see the blush spread to her neck.

Caught unawares, she was easily pulled her over my guest's lap. Mary, surprised, fought back, but my guest skillfully pinned her arms. My slave whimpered as her skirt was raised, she clenched her legs tightly shut. My guest paid that no mind and rubbed her outer lips, Mary shivered. I knew with her earlier denial she would not be able to hide her arousal. "Perhaps I could warm her up a little for later?"

"I suppose, but only a little. I like a fresh canvas."

Mary had remained strangely silent thus far. This changed with the first spank. She looked at me in with a plea in her eyes, but that only aroused me. When I smiled, her body relaxed a little, even as my guest continued her onslaught.

It was over as quickly as it started, my guest expertly stopping just as Mary's cheeks began to grow pink. My guest shot me a look and then poured some of the chocolate on my slave's ass. Mary squirmed as it rolled over her sacred areas, then she froze: my guest ran a strawberry through the mess and ate it. It continued this way until a good part of the chocolate had been eaten. Then my guest slipped a strawberry into Mary's pussy unexpectedly.

And tasted it. "Mmm you are almost ready for your big night, slut, but perhaps we could use a little more of you sweet nectar; we would not want your Master unhappy would we?"

"No!" My slave was alarmed.

This surprised my guest.

"She is a very devoted slave." I explained sanguinely.

My guest nodded and without comment started with a new strawberry, working it in and out.

Mary made soft noises of protest, but no more.

"My poor girl," my guest chuckled, "Being fucked by a strawberry." My guest relented eventually and tasted. "Yes, you seem ready now." My guest offered the rest of it to my slave, "don't you agree?"

"Yes, perhaps it is time." I stood. "You may observe if you wish."

"Of course I will watch. It is not every day I see a true great practicing his craft."

"You flatter me."

"Don't be humble. Your talents are unquestioned."

"I have never worried what the others thought."

"Yes, I know, but they still think much of you anyway. As do I."

We had made our way to the bedroom. I took my slave into my arms and kissed her deeply, letting my tongue tease her and soothe her nerves. "Are you ready?"

"I'll do anything for you, Master," she said bravely, even trying to smile.

I kissed her again, let her lean into me, using the strength of my body to support her. I turned her so we were both looking at our toys spread out before us. Black, sinister weapons; their appearance made it clear what their purpose was. "Are you sure? Let us not hide what is coming." I felt her whole body stiffened. I ran a finger over the cleft of her pussy. There was a clear trace of dew on her lips, so I pressed a finger in. She was just a little wet; too afraid to be especially aroused.

"I love you. I swear I will make you proud to own me."

"Very good Mary," I said, and we kissed a third time. She felt a little desperate. I had kept her on edge for long enough. For the sake of her sanity it was time to start. "I love you too."

I sat her in the center of the bed. I turned to my guest and motioned to a chair. "Please take a seat. I would prefer if you kept silent, although you may ask questions."

I received a solemn nod.

I turned back to my slave. "Strip, please."

A bit surprised, she did so quickly, tossing her outfit to a corner of the room.

I ran my hands over her body as she knelt on the bed.

She trembled, and then quietly spread her legs when I pressed a finger in.

"Hmm, you are wet, aren't you?"

She giggled and blushed even more.

I knocked her onto her back on the bed.

She stopped smiling; she knew what was about to happen.

I did not speak as I cuffed her in a spread eagle position. She offered her limbs to me in perfect obedience. She was a slut and would submit willing, inventively, and do all the right things. But she was not a masochist and was therefore afraid.

I turned to the dresser and took two clamps. I watched my slave's eyes as I dropped them on her belly. She tried to seem cool, but my experienced ears could tell she was breathing faster. I sucked her nipples to make them rise off her tits. To shiny little red points standing proudly at attention for me. I pinched them a bit, and I caught Mary's barely audible cry.

I tisked, "don't let me down."

I reached for the ball gag and she willingly opened her mouth to accept it. Once that was done, I took one of the clamps and traced her tit with it. She whimpered into the gag. I kissed her nipple once. "Look at me."

Her eyes opened wide and I kept eye contact as I attached the clamps. She groaned and twisted, unconsciously trying to shake them off, but kept staring at me.

I smiled down at her, "There. That is not so bad is it?" Of course I had not tightened them very much. I thought that she tried smile back at me around the gag. It faded when I held the crop over her. I began kissing down from her tits. She writhed a little when my kissing tickled her belly. Then I made my way down to her pussy. I kissed around her thighs and she struggled against her restraints to close them.

When my tongue grazed her lower lips they parted of their own accord. Her scent was strong. She moaned, lifting her hips to get more. But I pulled away.

She opened her eyes just in time to see me bring the crop down on her inner thigh. I was thankful I had put the gag in, because it sounded as though she was emptying her lungs in earsplitting agony. I worked quickly peppering her thighs, stomach, and tits with sharp blows. Very soon she was sobbing. I reflected it was probably better for her that she did not know what else I had in store for her.