Stupid Little Whore

"How many men have you slept with?" I asked

"Four," she said.

"Call me Sir when you speak to me. Okay?"

"Yes, Sir."

"Have you ever been with a woman?" I asked.

She was close to cumming. I could hear her breathing quicken. "I have thought about it, Sir."

"If you want me to train you, I will ask you to do things that you may not have done before or that might be painful." I said softly.

"Like whip me?" She asked.

"Yes. Like whip you." As the words left my lips she came hard. Her body shook violently. I watched her breathtaking display in front of me. This woman was sexually repressed. She needed someone to tell her it was okay to be sexual and naughty. When she began to come down I asked, "Does that excite you?" I wondered if thought of the crop pushed her over the edge.

"Oh yes. It excites me a lot." She said breathing heavily.

"Get on your hands and knees." I commanded.

She slid from the couch to the floor in a naturally submissive pose. She continued to touch her pussy. Two fingers plunged in and out of her wet hole. She came again and then again. I finally walked around to her and rubbed her round, firm, full ass. I slid my hand between her thighs and rubbed the slit of her pussy. It was extremely wet. I wanted nothing more than to take out my cock and bury it inside her. I unzipped my pants, letting them fall around my ankles. I grabbed my erection and started stroking it slowly. She turned her head to look back at me catching a glimpse of my cock.

"Eyes forward." I said sharply. I stroked furiously until I was ready to explode. I aimed at her beautiful ass and shot an unusually large load of cum all over it. I could hear her gasp when the first warm jets sprayed her skin. When I was fully drained I pulled my pants back up. I grabbed her panties from the floor, and started to slide them up her legs. She lifted her knees when I got to them allowing me to pull them up her thighs and finally covering her cum covered ass. She reluctantly pulled her fingers from her pussy as I pulled them up. Her panties began to discolor immediately as the cum soaked into them. I pulled her to her feet and handed her the jeans she had worn. She put them on. I was mesmerized by her breasts as they swung back and forth while she pulled the tight jeans around her ass.

"You will not shower until tomorrow morning. You may not change your clothes. You will sleep in those panties tonight." I said.

Again I heard a gasp from her. Everything seemed to excite her. I grabbed a pen and paper. I wrote down the name and address of a store.

"I would like nothing more than to fuck you. I just can't do it until my fiancé arrives and begins her training. If I fuck you, she will be there to watch. If you like that thought... if you want to be trained, you will go to this store." I handed her the piece of paper. "You will buy a padded black bondage collar like the one you're wearing, a black garter belt and black stockings, and a pair of strappy black high heel shoes. You will bring them with you in a small bag the next time you come here, and you will wait to hear instructions from me on what you should do."

Her hand shook nervously as she took the paper from my hand. "Y-yes, Sir. Thank you." She said softly.

"Now get the rest of your clothes on, and get out of here for the day. You did a wonderful job cleaning as always." I walked out abruptly without waiting for a response. My cock was hard again already. Twenty minutes later I heard her walk through the house toward the front door. She poked her head into the living room and said she was leaving and she'd see me next Saturday. She smiled wide. She was happy. As she turned, I could see the dark stains soaking through the ass of her jeans. I knew she must have felt very naughty. I couldn't believe my luck with this woman.

That situation had unfolded exactly one week ago. So this is how I found myself on this particular Saturday afternoon. My housekeeper sat at the kitchen table sipping coffee with me and clutching a small bag that held some intimate belongings. My fiancé was locked in the bathroom in the guest house turned sex room with a butt plug in her ass. And a relative stranger, who happened to be my new roommate, sat in my office monitoring a live video of my fiancé making sure she didn't remove the medium sized, aforementioned butt plug I had lodged in her earlier today. Maria looked nervous. Her nipples pressed at the fabric of t-shirt. It wasn't cold inside, so I could only assume she was turned on.

"Hey, mate? Can you come in here for a minute?" I heard Mr. White calling me

from my office.

"Come with me, Maria." I said walking toward the office. Maria followed behind me still clutching the bag. Mr. White was rewinding the video when I arrived in the doorway.

"What's going on? Has she been a bad girl in there? I'm going to be pissed if she took that thing out." I said.

"Um, it's a little more complicated than that I think. Uh, you might want Maria to leave us alone for a moment while I show you this." He said motioning toward the petite Colombian woman hovering behind me.

"I'll handle my employees, thank you, Mr. White." I snapped at him. I'm not even sure why, but it surprised him as much as it did me. Maria just smiled at me happy at my decision to include her.

"Suit yourself, mate. Here, take a look at this." He said shrugging off my tone and pressing play.

"Maria, come watch this with me." I said motioning her forward toward the screen. Mr. White stared at me confused as to why I would include the housekeeper.

On the screen was a picture of Ana running a bath for herself. She stood by the counter trying to look back at her ass touching the purple marks from her punishment. She sat down on the corner of the tub letting her feet soak while the tub filled. After a moment she reached for the shaving cream and razor, presumably to shave her legs. It was just out of reach. She went to stand and had a noticeable issue. Her face contorted slightly and she looked down towards her ass.

It appeared as if the butt plug had suctioned to the porcelain ledge on the tub. She probably hadn't realized that the bottom of the plug had suction capability. I was amused. She had tried to stand again and then unsure of why she was stuck there jumped up in a panic. The plug popped out with an audible sound and she made an "oomph" noise as her asshole stretched wide freeing itself from the intruder. She looked around guiltily as if someone had seen, but she was alone. The cameras were well hidden. She'd never find any.

Convinced that she was alone she stared at the plug. She unstuck it and picked it up. She tried to measure the girth by wrapping her fingers around the widest part. She looked around the room again frustrated, probably from the lack of mirrors. She pulled one ass cheek to the side trying to look back at her asshole. She looked a little like a dog trying to catch its tail. She wanted to see the opening. She reached back and touched her asshole. She put a finger in her ass, then two. She was shocked by how wide open she felt. She pulled her fingers out finding my cum on them. She raised them to her mouth licking tentatively at first and then cleaning them thoroughly. She sniffed the plug holding it to her nose and then stuck it back to the ledge.

She slowly sat trying to aim the tip of it back into her asshole. She got it nearly all the way in before pulling off completely and then sitting again. She was hesitant to get over the hump. She started bouncing on it as if trying to open up her hole. Then strangely enough she started touching her pussy. She was riding this plug two thirds of the way and making herself cum. Finally she pressed down a little too far and her hole crested the girth of the plug, planting it inside her. She froze still. Then she stood up quickly letting pop out and then down again all the way. She smirked. She tried that a few more times until she exploded in a powerful clitoral orgasm. Finally she left it planted in her hole where it should have never left.

"Son of a bitch!" I said. "Did she or did she not squeal in pain when you fucked her in the ass this morning?" I asked confounded.

"She cried like a little girl, mate. That hole was fucking airtight when I cracked it open. I know it hurt. I fucked it for a good long while though before I came in it."

"So what you're telling me is after years of dating this slut, and hearing her complain about taking it in the ass, she now likes getting her hole stretched? That is unbelievable."

"Doesn't look like that's much of a punishment at this point, mate." Mr. White stated.

"Shit! Shit! Shit!" I was furious with this girl. "Maria, did it look like she enjoyed that butt plug?"

She looked jolted at being asked to give an opinion on this obscene video she just watched. She paused for a moment clutching her bag even harder. Then she said, "it look like she like putting it in and out of her ass to help her cum... Sir."

Again Mr. White eyed me as if he wasn't sure why the housekeeper was even here much less giving an opinion. And now she was responding to me as Sir.

"Exactly. That is exactly what I saw. I mean I told her explicitly not remove that from her ass. And why is she cumming on her own? Did we not tell her she wasn't allowed to cum without our permission?" I asked aloud, but to no one in particular.

"I didn't give her that instruction." Mr. White remarked.

"Hmm. I guess I didn't either." I said. "Well she needs to be punished for this. I mean this girl loves me. I know that. But she can not follow instructions for shit. I need to knock her down a few notches. Get her off of her high horse."

"Whip her again?" Mr. White suggested.

"No. That's not good enough. We need something emotionally and physically exhaustive." My mind was turning. I glanced to the side and saw Maria still standing there nervously clutching her bag. "Well, Maria, do you like what you've seen so far? Do you like watching my fiancé?"

"Y... yes, Sir." She spoke sheepishly again.

"Well you don't sound so sure. Either you like this or you don't. Do you want to be a part or not?" I said it dismissively like I didn't care about the answer. Deep down I was praying for her to say yes.

She paused. I think she thought about how I had been referencing my own fiancé, and knew not to take my tone offensively. "Yes, Sir. I want to be part of this things." She said.

"Well then I think you should stop strangling that bag in your hand, and make use of its contents. Okay?"

"Yes, Sir." She said turning toward the bathroom.

"Where are you going? Get back here." I said.

"I'm sorry, Sir. I was going to put on..."

"Going where?" I cut her off. "Right here is fine."

I looked at her. She glanced at Mr. White embarrassed. I suddenly realized the issue she was having.

"Oh. Shit. I'm so sorry. I can't even think straight today. Um...I introduced you both earlier. Mr. White, Maria. Maria, Mr.White." I did the quick reintroduction. "Mr. White here is helping me train Ana. He helps me with discipline and fucking her." I said to Maria. Then turning toward Mr. White I said, "Maria here wanted to clean the guest house last week and stumbled upon my play room. Turns out she liked what she saw." They both acknowledged each other with a newfound understanding. "Great." I said. "Now either put that on or go clean. We need to get to work."

Maria glanced at Mr. White and then began to undress. She took off her t-shirt first and her breasts spilled out in a massive jiggling mess. Oh they looked so good. No bra. I liked that. Next were her jeans. She pushed them down toward her ankles bending over at the waist. Her ass jutted out into the air, a thin piece of g-string fabric disappeared into the crack of her ass, but that was soon gone as well.

"Fantastic." I said looking at her. It made her smile to see my approval. Mr. White instinctively reached out to touch her breasts. I picked up a spare crop that I kept in the office, and swatted his hand.

"Not for you." I said playfully. "This is my new little project. I'll be the first to fuck her, and she's hands off unless I say otherwise." I raised the crop again and cracked it on her ass. She smiled a devilish smile, and Mr. White could see that she enjoyed the rather hard smack. "Fantastic!" I stated again.

Maria soon had on her new uniform. The black stockings and heels looked sublime. The garter belt hugged her ass and hips perfectly almost like a second skin made just for her. My cock begged for release. She reached back into her bag and grabbed the black padded bondage collar. She fiddled with it in her hands.

"I'll take that, Maria." I reached out and took the collar from her hand. "When I put this on, Maria, it's called collaring. It means you want to be trained. When you come here you will wear it. When you wear it, you'll follow my instructions and do as you're told."

"Yes, Sir." She smiled. She liked the idea of being collared.

"Kneel." I said. She slinked to the ground in front of me. I took the collar and wrapped it around her thin, fragile neck and clasped it tight. "How would you like to try licking some pussy?"

"I like to try, Sir."

"Excellent. I want you to go wait at the door to the guest house. When you come in with me, I don't want you to say a single word. Just do what you're told." I liked how closely she listened to her instructions. "When's the last time you got fucked?"

"November, Sir."

"Would you like some cock today?" I asked.

"Oh yes! Please I like that very much, Sir!" She exclaimed.

"Ok. We'll see how you do. Get going."

Maria left us in the office. I looked back through the footage. I just wasn't sure what to do. Ana wasn't listening very well. As usual, she said what I wanted to hear, but she didn't act accordingly. I didn't want to traumatize her on day one. I thought maybe a little heart to heart to start would be a good plan. I wanted to see what she said. I wanted to see if she was willing to acknowledge her mistake.

Mr. White sat in the chair next to me. He hadn't said anything since Maria had stripped naked. I noticed him staring at me with a quizzical look on his face.

"What?" I asked referring to his expression.

"What the fuck was that mate?" He asked wagging his finger at the pile of clothes Maria left behind.

"You mean Maria?" I asked.

"Yeah. How the hell did that happen? The housekeeper last week, and this week a collared slut?" He looked perplexed and amazed at the same time.

"I dunno. I just fell into it." I said shrugging my shoulders. "She has a fantastic body though, right? I mean how excited are we? Don't worry. I'll let you have a go at her eventually."

"I... I just don't know what to say, mate. You might be my hero."

"Shut up, dick. Don't get all gay on me. C'mon, let's go figure out what to do with Ana."

I walked out to the back and found Maria kneeling in front of the door to the guest house. I admired how easily this submissiveness came to her. I tapped her shoulder and motioned her to follow me inside. They both knew to stay quiet until they were called upon. I walked in and knocked on the bathroom door before opening it. Ana knelt on the bath mat by the sink.

"How's my slut?" I asked. "Feeling better after a bath?"

"Yes, Sir. This girl feels much better now."

She had dressed back in her pink bra and panties. I calmly reached over removing both articles. She understood that she would not need them. I bent her over the counter and wriggled the end of the butt plug.

"Still intact." I noted.

"Yes, Sir. This girl wouldn't take it out without permission."

I noted the blatant lie and walked her out to the sofa with her blindfold back on. I sat her down and massaged her shoulders.

"Thank you, Sir. This girl really needed a massage."

"It's my pleasure. You had a really hard night last night and hard morning as well. Do you know how much I love you?"

"Yes, Sir." She said nuzzling her head into my chest.

"About this morning, Steph, I'm sorry you got whipped so hard. Those marks will go away in a week or so. I'm just really not okay with you saying things that you don't mean. Telling me you'll do something that you never intend on doing. And lying. You lie all the time. You even lie about stupid stuff that isn't worth lying about. You know?"

"I'm sorry, Sir. This girl promises to be better."

"Well, I just don't think you know how deeply I love you. Part of the reason I want to train you is so you can be a better partner. I don't want you to look for a job because I don't want you to feel overwhelmed. I want you to have time to work out, which you've complained about. I want you to have time to learn to cook so when we have a family we won't always be eating out. I want you to have time to keep our home cleaned. I'm not trying to force you to be a housewife. You can get a job again if you want. But, well, you've made me carry the weight in our relationship doing most of the work. I just want you to help. I don't mind sharing responsibilities, but I do want help... without complaining. I don't consider it helping out when you complain profusely about it. Okay?"

"Yes, Sir. This girl didn't know these things bothered you so much."

"I've told you before, but I just don't think you listen anymore. You're selfish. If you don't want to do something then you just ignore me. I don't want to live like that. I don't want that to be my reality for the rest of my life."

"I'm sorry, Sir. This girl promises she'll change. This girl promises she'll learn to be a better wife. This girl is really sorry."

"And the lying?" I asked. "You'll stop lying to me to?"

"Yes, Sir. This girl promises."

"Thank you. That's all I ask." I leaned forward and kissed her lips. She kissed back in need of affection.

Mr. White and Maria sat quietly watching this conversation unfold. They saw that I loved her. They saw our moment of understanding in the midst of the craziness. I wrapped my arms around her and held her tight.

"How would you like me to take that plug out for you?" I asked.

"Oh please, Sir. This girl would love to have that taken out."

"You didn't like having it in there? Was it uncomfortable?"

"Yes, Sir. This girl hates having it in there." It hadn't looked like she hated it so much on the video I thought to myself.

"You were a good girl, right? You didn't take it out in the bathroom?" I asked.

"Oh no, Sir! This girl would never dare take it out without permission. This girl hasn't touched it." She said.

I looked over at Mr. White and Maria. They were shocked at her blatant lie just a minute after she said that she wouldn't lie anymore. It was just as I assumed. She was entirely disingenuous. I reached down and touched her pussy and clit. She cooed in my ear at the soft attention.

"Have you cum today?" I asked.

"No, Sir. Mr. White said I wasn't allowed to cum while being punished even if he fucked me well."

I nodded to Mr. White for a job well done. I also noted the second lie since I knew full well that she had made herself cum.

"Well, my love, do you want to try something that will make you cum really well before I take the plug out."

"Yes, Sir."

I left her on the couch and went to the bookshelf. I removed a vibrating egg with a remote control and an eleven inch extremely thick dildo. I set up what looked like an mic stand in the middle of the room. It had a large flat, heavy metal base and an adjustable metal rod the came up vertically from the center. I could see my two friends watching me carefully. I walked back over to Ana and inserted the egg inside her. She was being very good.

"Trust me; you've never felt anything like this before I promise."

"Full of new tricks, aren't you, Sir." She said playfully.