Housesitter Sunday

Mary started crying at this. She pulled up her pants.

As she was about to button them the old guy spoke to her. “You have a beautiful pussy there, honey, but you need to shave it completely.

Mary broke down, sobbing; she threw her bra and vest on. I moved up to the cashier, with her in tow. The guys, guessing that the show was over, left.

Julie arched her eyebrow at my choice. “I would not have thought that fit your designs.”

“I love the classics.”

We both laughed, Mary was beginning to calm down now.

“Could you put this up while we keep looking?”

“Of course, may I help you with anything?”

“Yes, I was wondering if you had some lotion.”

Julie smiled warmly, “Of course.” She reached down under the counter and came up with a green squeeze bottle.

“Thank you. Someone was bad today.” I turned to Mary. “Come here slut.”

Mary reacted to being called that in public, but scurried forward.

“Get up on the counter.” When she hesitated I smacked her ass hard. She yelped from the blow on her already punished ass. She hoped up on the counter quick. “Lie down on you stomach.” Her eyes got wide, but she slowly complied. I reached around and unbuttoned her pants, smiling as she tensed. I pulled the pants down to Mary’s knees, leaving her ass completely exposed and vulnerable. She immediately started to cry. I stroked her ass, causing her to cry more, and whimper and start whenever I touched a welt.

Julie nodded. “Pretty little thing. Only seven? You are slipping.”

“It was her first time.”

“Oh! You are too cruel. No one should get it this hard as their first time.” She leaned over to talk to Mary. “You poor dear, no wonder you are crying so much.”

I opened the lotion. “This will ease the pain a bit, okay?”

She nodded and choked out, “Thank you.”

She arched when I poured it on her, it is always cold to the skin. I started to rub it in, and Mary began to moan slightly.

“Does that feel better?” Julie asked.

“Yes.”

She straightened and poured some lotion into her hands. “May I?” She asked me.

“Please.”

Mary bolted when she felt a second pair of hands on her body. She remained tense the whole time, sobbing softly.

“Spread her cheeks for me would you?”

Julie smiled and spread them. Mary’s whole body shook as she cried.

“Did you bugger her on her first day? You are so hard on your slaves. You know you should not give them that weapon of yours so soon.”

“Nonsense. She had to learn, there is no use coddling her. If I baby her at first she will just have to relearn later. She took it well enough for her first time.”

Julie’s eyes widen. “You mean she was a virgin back there? You are too cold-blooded. She is lucky to have survived.”

“She is fine. Mary, tell her about your first time ever being assfucked.” I slid a finger into her ass. She gasped, but I continued to work it around rubbing her bruised ring. She whimpered non-stop, but slowly relaxed as the lotion eased her pain.

“How did you like him fucking you up the ass dear?” Julie asked.

“I wanted him too at first, but it hurt so much I could barely stand it. My poor bum will never be the same.” She cried.

Julie patted her on the shoulder. “There, there, sweetie, it is never as bad as the first time.”

I slid a second finger into her ass and Mary dissolved into tears. I worked the two fingers deep into her. She tried to move away when it started to hurt. Julie shot me a dirty look when she realized what I was doing. I grinned and eased my hand out. I tested her pussy and found it dry.

I got a towel and proceeded to wipe off my hands.

“Master?”

“Yes?”

“May I please get down now?”

“No. The lotion needs to soak in and I find your position amusing.”

She choked at that, but did not say more.

Then a young man came up to the counter. Mary tried to slide away, but a sharp slap on the ass from me, brought a stop to the movement and a cry.

The man stopped in confusion.

“Oh it is okay, it is just that Mary here was reamed for the first time and her hole is still sore.” I rested my hand on her ass.

Mary jerked when she felt my hand, but just lay there quietly, shaking from crying.

The man smiled. “Crazy.”

I noticed Mary hiding her face. “Tell him that you are okay slut.” I placed my thumb right on her asshole.

The effect was electric. Mary’s head shot up and she looked right at him. “I am okay, just a little sore.”

She remained up as long as my thumb was there. I was impressed with her conduct and slid my hand down to her pussy. She put her head down and began to moan. The man left with his purchases and I continued to finger her.

“Exposing her that way on her first day?”

“Will you get off of my back? She was a slut already; I know how to do this.”

“You are being too hard on her.”

“No I’m not. That is impossible, she is mine to do with as I please. She knows that.” Mary was pushing back against my hand now. I pulled out. She whimpered.

“Yes slave?”

“Please Master, let me cum.” I ran my fingers around the edges of her hole. “Please.” I slipped some fingers in and soon had her writhing and groaning. She came yelling some indiscernible phrase. I let her come down at bit and stuck my hand in her face. She understood and licked my hand clean. “Thank you Master.” She kissed my hand and rubbed it against her face.

“Pull up your pants, slut, we have more purchases to make.”

Mary slipped off the counter. She slipped her pants back up, wincing less when they touched her ass. “Thank you Master.”

“Grab a basket.”

She scurried to do my bidding.

I began to walk down the aisle, Mary kept up behind me. The first section was cuffs. Besides just a set of normal handcuffs, I also purchased a pair with greater range of movement, a pair of ankle cuffs, a chain to connect them, and a body chain. I completed the package by getting four single leather cuffs, with ties at the end (for bedposts). Mary took this all in without comment. Then I pulled a collar off the shelf. It was a black leather affair, with a metal inside and a small lock in the front. There was an attachment for a leash, so I picked one up. I motioned of Mary, she came quietly forward. I handed her the collar, with leash attached.

“Put it on.”

She hesitated, but closed it over her neck, locking it. I held out my hand, she removed the key and gave it to me. I pocketed it, and held out my hand again. She was confused for a second before realizing and handing me the leash. I turned and continued on my way, leading my slave.

We turned the corner and found toys. “Pick one you like.”

She looked at me in surprise. “Go on.” She blushed, but made her way, down the aisle. She finally selected a medium sized, ridged, blue dildo and put it in the basket. “Now get yourself a vibrator.” Her pause was much shorter this time, she quickly selected a small, thin, black one. I made my way along and paused when I saw a white plastic egg. I correctly guessed what it was. Mary looked over my shoulder, but made no comment when I added the remote vibrator to the basket. I saw her lower lip tremble when I pulled the butt plug off the hanger. Then I saw the coup de grace. There were several of them, so I made sure to get a size five. Mary choked when she saw the two rods sticking up out of the seat of the chastity belt. I smiled at her as I put it in the basket.

She was white as a sheet when she spoke, “Master?”

I turned to her, “Yes slut?”

“I’m not sure I can handle that.”

I rubbed her crotch lightly, “you’ll learn.”

She looked down at the floor, but was silent.

I continued on my way, coming to the torture section, Mary’s eyes went wide at this. My first selection was a classic full headed mask, with closeable holes. Next was a red ball gag. Mary eyed these warily, but kept quiet probably thankful this was all I was getting. That changed when I pulled a short leather whip out of a bin. She did not say a word, but just started crying.

“Unless you want me to test this right here, you will be quiet.”

She managed to control her tears, even as I added a velvet riding crop and a long wooden paddle to the bundle. I patted her on the ass and moved along, having to tug on the leash to get Mary’s attention. When she saw me take three sets of nipple clamps, she visibly trembled.

“I think we have enough for today, don’t you agree?” Mary violently shook her head and I laughed.

Julie tisked when she saw all that I bought. “You need to break her in gently.”

“Will you stop insisting that? If I need instruction on something I’ve done many ties before, I’ll seek it out. Besides where do you draw claim to be able to tell me how to train a slave? Have you my expertise?”

“Not at you end of the bargain, but I know how she feels.”

I laughed. “Then do not presume.” I pulled Mary’s leash to get her attention and bring her to me, and began to stroke her body, rubbing her flat hard stomach and just glancing onto her pussy. “I know how to mold her to what I want. I may be a bit harsh in your eyes, but I demand complete submission.” Mary moaned as I fondled her cunt. She hissed lightly when I brushed over her sensitive nipples. I pulled my slave back to my body and rubbed my now hard member against her ass and she shuddered. “Mmm, I think you may need another lesson right now.”

“Not here.” Julie interrupted.

I looked at Julie in surprise. “What is this? Did the powers that be put in new policies when they reorganized?” I gave her a look to let her know not to play with me.

“No, but I will not help you brutalize that poor girl.” She did not look like she wanted to test wills with me.

“It’s okay,” both of us were surprised when Mary spoke, “I want to please him. If that means I have to be a slave, then I want to be the best slave he has ever had.”

I smiled winningly at Julie. “May I please see the key to the back room?”

She grudgingly handed it over. I stowed my purchases underneath the counter and lead my slave by her leash to a door in the back of the store. She blushed when another customer saw me leading her. The back room was just a little lounge room, a couch, table, etc., but no bed.

I pulled Mary in for a passionate kiss and cupped her hard ass. She slid her arms behind me and ground her crotch into my hardon. I broke off the kiss. “I am proud of you Mary; you are learning what it is to be slave.” She smiled. “Now I believe I mentioned a lesson…take off you bottom.” She gracefully slid her pants down to her ankles and stepped out of them. She put her hand over her pussy very demurely. I pulled her in for another kiss. This time I ran finger over the edge of her slit, pulling my hand away when she pressed down wanting more. She murmured her frustration. I rubbed her ass lightly and lead her over to the couch. I took my pants off and sat down, my purple leader pointing straight in the air. I guided Mary’s hand to it.

She squeezed it and giggled when it twitched in response. “I can’t get over what a huge dick you have. I do not know anyone who has one this big.” She stroked it bit. She bent to kiss it once and looked up into my eyes with total submission. “What do you want me to do Master?”

I paused to consider for a moment, then I came up with the perfect idea. “Use it as a dildo and fuck yourself in the ass.”

She tremble in fear, but began to move over me. I was impressed how quickly she was learning to be a proper slave.

“You may find it easier to face away from me,” I suggested.

She looked down and considered before turning around in agreement. She slowly brought herself down on me, stopping when she felt my tip on her asshole. Ever so gently she guided me into her, whimpering. She paused in order to quickly bounce up and down just on my tip to stretch herself before feeding a little more of my cock up her near virgin ass. It took her nearly twenty minutes to get me inside her, even though she was slick from the lotion. She was wincing from hurt, but dutifully doing her job. She leaned forward and slowly rose up and down on my cock, never letting the head pop out, despite her grunts of pain. When she got a rhythm going, I started to finger her. She was soon cooing contentedly between grunts after getting over the surprise. I worked her pussy over, her juices soon pouring down her crack onto my balls. I attacked her clit, twisting it slightly to blur the line between pleasure and pain. She went wild, moaning and groaning loud enough everyone in store probably heard. She was flying over my cock now, oblivious to the pain in her ass. When I felt myself about to shot my load into her bowels I pushed to her snatch and rubbed my cock through her thin membrane. Full she nearly fell off the couch when I did, but she howled as came, falling back on me, burying my cock into her ass up my balls as I shot deep inside her. She lay on me panting as she came down and I softened. “Oh, god Master, it hurt so much, but it was incredible at the same time.”

“How are you now?”

She shifted on me. “It is a little sore.”

“Get up and let me see.”

She promptly stood and spread her cheeks. I poked her bruised hole a bit and she hissed, but did not move. “You will be fine, now clean me off and let us go get some dinner.”

She sank unhappily to her knees yet tenderly sucked out every last drop of cum. I could tell she still did not like the taste of my cum, or her ass, but was beginning to accept she had to do it.

We grabbed our purchases and left.

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

Dinner was pleasant enough. We went to a small, out of the way Italian place I frequent. I already knew Mary was flakey, so I did not try to have a serious conversation with her. Instead we just made small talk as I subtlety questioned her about her life. She has always been a nice person at least. She flirted with me off and on too, much to my surprise, but I did not mind.

Afterwards, as we walked to my car, she hung on my arm as she asked what we were doing next. “I am not sure. This morning I considered going to a poker game with some acquaintances, but that is really a gentlemen only affair. If not, then I was simply going to stay in and do some reading.”

“Well, what are we going to do?”

“As I said, I have not yet decided. Have you any suggestions?”

“I was planning to hit the clubs.”

“That has little appeal to me.”

“Umm…I don’t know…do you want to go to a movie?”

“I was considering that, but I have to confess I have little idea of what is playing now.”

“I am sure we can find something.”

“Fair enough.”

It was only a short hop to the theater, but once there I did not recognize any of the films (I should note that I rarely participate in mainstream culture). I decided to defer to Mary, as I did not see any of my favorite actors. I could pay $16 and waste two hours on a bad film without heartbreak.

Mary recognized a group of chicks, and said hello quickly, but they had to go.

She picked “The Truman Show” and we settled into a lightly patronized auditorium.

“That group presented an issue that I have not addressed with you. Namely: how to explain our relationship to your friends.”

“I thought of that, I assume that you would want me to call you my boyfriend.”

“I expected that, but I would rather you just say I am you friend. Later, when I am not present, explain that you are trying to get me. We have gotten mildly physical a few times, but I am not interested in a true relationship as yet.”

“Okay.” She sounded a little hurt, possibly with some confused mixed in. “What does “mildly physical” count as?”

“You get into that level of detail with your friends?”

“Some of them.”

I paused to think. “You have happily let me handled you everywhere thoroughly, and repeatedly, but fully dressed. You have only hugged me tightly.”

“That is looser then I normally go. I do really know if I like that.”

“You have let me take liberties because you really like me,” I said firmly.

She knew not to push the issue, but she seemed to pout.

“If I find you have not been following my instructions to the letter, I will give you fifty lashes, and I know how to make them count.”

“Yes Master,” she said softly. I could hear real fear in voice.

“You have an uphill battle in getting me as once we watched a tape and you got a little drunk. You got down on your knees before me on the couch and told me you wanted to blow me. I was not interested you while so drunk, but you kept begging and telling me what great head you gave. I refused and left. You felt awful about it later, but we have not spoken about it.” I was pleased when she just nodded.

I decided to give Mary a break during the movie, largely because it turned out to be rather amusing. I am not normally a fan of Jim Carey, but the concept of the movie was original and interesting, if unbelievable. There were some predictable parts, but it was good on the whole. Some of the dialogue was high quality. Mary curled up against me during the film.

After the show was over and we started out, Mary asked me if I had enjoyed the movie. After we discussed the movie, which she loved, I was presented with the same problem as before. It was not yet even 10:00. I mulled the situation over. If I was alone there were numerous places I could visit, but none I would take Mary to, at least not until she was better trained. So once again I picked my slaves brain. “Where would you go if I was not here?”

“I would go to a club.”

“Are any of them interesting?”

“What do you mean?”

“Are any of them more then just a place to get inebriated and dance to loud music?

“Not really, some of them have bands, but that is about it.” She hesitated, “Do you mean a strip club?”

“No, that was not what I was driving at. Why? Do you go to them often?”

“No,” she laughed, “I have been a few times to different clubs, sometimes my boyfriend brought me, or I went with a group of couples.”

“Did you enjoy it?”

“Umm, kinda, yeah,” she embarrassedly pushed her shoulder length hair behind her ears, and looked away. “I mean it was thrilling to see all these naked women around you, and feel my boyfriend mauling me under the table, sometimes he would unbutton my pants and finger me. We always screwed like crazy when we got home. One time when I was with a group I gave my boyfriend a blowjob right at our table. It was a risqué place and it was dark, but everyone at the table watched me. I was embarrassed, but my boyfriend really wanted me to. There isn’t a place like that here, that was in Boston. I don’t know if you remember reading this but I was an exotic dancer down in Boston too.”

“When was that?”

“Two years ago, I had just turned eighteen. I was not nude; I just wore a bathing suit and danced. It was great money, but I felt kinda dirty.”

“Well all of that is interesting news, but not really what I am looking for tonight. Any other ideas?”

She thought for a few minutes, “there is a comedy club downtown.”

I perked, “how good is it?”

“It’s okay.”

“We’ll try that.”

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

The comedy club did turn out to be okay, if not great. The line up gave some good jokes, but some bland ones as well. There was a fairly large crowd. Mary surprised me by asking me if she could have a drink. I had not noticed when she did not get one with dinner, even though I knew she was twenty-one. I let her have few and she held up well, but I did notice her laughing more at the jokes as she drank. I could tell comedy was not really her scene and after a run of bad comics I decided we should leave.

Now it was midnight and I was ready to go home, which surprised Mary even after I told her we were picking up a video. She did not realize she had quite a night ahead of her.

I quickly selected “Platoon,” one of the better Vietnam movies in my mind, on the way home. Mary wanted a romance, but I ignored her.