Training Michelle – Day 3
I was sleeping soundly when something disturbed me. I couldn’t quite place the sounds, so I opened my eyes and looked next to me on the bed. Michelle and Susan were locked there in a passionate sixty-nine, attacking each others’ pussies. Susan was on top, with her head towards the foot of the bed, Michelle was on her back with her head near mine, but hidden by Susan’s leg. I raised up and looked into Michelle’s eyes. She grinned up at me. “Good morning Master.”
“Good morning yourself. Would you care to explain this, especially in light of last night’s discipline?”
Michelle paused in her assault on Susan’s pussy long enough to say, “We decided that we both wanted your cock, so first one to cum has to wait.” She went back to Susan’s pussy.
“And what makes either of you think you make the determination. Or for that matter that anyone is getting my cock this morning?”
Michelle looked at me and grabbed my erection. “I think someone will.” She grinned, “And we both want it inside us.” She lost the bet. I watched as her eyes rolled up and she screamed, “Oh god! Yes! Nooo!” And her hips bucked as she came into Susan’s mouth. She swore softly, “Damn.”
“It’s okay Slave, no one gets my cock this morning, I’ve got things to do.” I rolled out of bed. “You two get up and get showered.” I looked down at a very disappointed Michelle. “Show her what she needs to know of the rules while she’s staying here.”
“Yes Master.” Michelle said. Then, “Let’s get a shower together. There’s something I can help you with while we’re there.” She grabbed Susan’s hand and dragged her off the bed. They ran to the bathroom giggling.
I made coffee and poured some for myself and Michelle, then realized I didn’t know how or if Susan took hers. I just loaded a tray for the possibilities and took it to the bedroom. They were still in the shower so I shaved and got some other things done while they finished. They got out of the shower drying each other off and laughing. Michelle turned Susan around to face me and announced, “See Master? I fixed her up.”
I looked and saw that Susan’s strip of pubic hair was freshly shaved. Susan looked at Michelle and said, “I think she just wanted an excuse to stick her nose back in my pussy.” Then they both giggled again.
Michelle kissed her and said, “It’s the rule. But you’re right.” She stepped next to Susan. “See Master? Now we’re twins.”
I laughed and shook my head. “There’s coffee in the bedroom. You two are in charge of breakfast, I’ll be out shortly.” And I stepped into the shower and started it. I heard the hair dryer briefly, a lot of giggling, then silence when they left for the kitchen. While I got ready for the day they were apparently busy in the kitchen, I could smell something cooking.
I completed my morning toilette and slipped on a pair of shorts on my way to the kitchen. While I poured another cup of coffee, Susan said to Michelle, “Hey, what’s up with him dressed and we’re naked? That’s not fair.”
Michelle replied, “Sure it is. He’s the Master and we’re slaves. Besides, I happen to like naked. Don’t you?”
“I especially like you naked.” Susan answered.
I asked, “How soon until breakfast?”
They looked at each other, and Michelle answered, “About ten minutes.”
“Then I’m going to make a couple of private phone calls from my office. Knock when it’s ready.”
In unison they said, “Yes Master.” Then they both giggled. I went to my office shaking my head. I called my friend about a possible position for Susan. I explained a bit about my relationship with Michelle, also that I didn’t know Susan well, but that she seemed to be very nice and smart. I suggested that Susan might be open to a similar arrangement. He was very interested, he’d just gotten back on his feet after a messy, nasty divorce, but wasn’t seeing anyone regularly. I e-mailed him a copy of the contract between Michelle and I and made an appointment for the three of us to join him at his office that afternoon. I called Julie and arranged a private fitting for Susan and had just finished promising a full explanation of my situation with Michelle, when I heard a knock on the door.
It was Susan who called out, “Master? Breakfast is ready Sir.”
“Thank you, I’ll be right there.” Susan was waiting patiently by the door when I came out. I looked at her, and asked, “Was there something more you wanted?”
“Yes Sir. Master? I’m not sure what to call you or to say.” She stumbled for words. “Michelle has told me about your relationship and shown me her contract. And I, um, I.”
“Susan, just ask. I won’t be shocked and I won’t be upset.”
“Sir, do you think your friend would be my Master? I could be his slave and do everything just like in the contract.”
“Susan, I’ve just spoken with him on the phone and explained somewhat of what’s going on. I honestly don’t know you well, so you’re going to have to get something together to prove your academic record as well as sell him personally. Do you have a transcript?”
“Yes, at my apartment.”
“Then we’ll need to pick that up when we go out a little later. For now let’s enjoy that breakfast you two fixed.”
We ate and talked about my friend and his business and we learned quite a bit more about Susan. I had every reason to believe she was truthful and she had had a hard life, but come through it in good shape mentally and physically. She had moved out of her parents’ house after an abusive childhood and had been on her own since she was seventeen. She had funded her own education after completing high school with honors despite providing for herself. I was impressed by her knowledge and poise, and intelligence. I knew enough about her field of study to know that she had real knowledge of the subject. She could have faked it from self-study, but she’d have devoted quite a bit of time. Education and determination seemed to be the deciding factors. She wrapped up with, “So when Davey called yesterday I agreed to dinner with him. We both wanted to get laid, and I figured it could be worse, even if it could be better. When the two of you walked in I realized it could be a lot better, then Michelle responded to my flirting.” She paused for a sip of coffee. “The rest you know.”
Michelle leaned over and gave her a kiss. “I understand. My life hasn’t been quite as hard as yours, but then again, I got real lucky in the last year.” She smiled at me. “I found a gentle loving older man to teach me and take care of me. I was really lucky.”
Susan sighed, “I just wish I could be that lucky, even now.” Susan stopped and then exclaimed, “Shoot, I don’t have anything to wear except the dress I had on last night! And one of you has my panties.”
Michelle laughed and Susan glared at her. Michelle said, “Silly, we don’t wear underwear as slaves, last night Master made me wear something special to go out, but I’m usually required to wear exactly what I’ve got on right now under my dress. All you need is your dress and shoes, once we get to his friend’s office I bet you won’t even wear that for most of your interview.” Michelle leaned over and kissed Susan. “Besides, you looked terrific in that dress last night, I’m sure it’ll be better over naked, and you look delectable naked.” I watched lust light up Michelle’s eyes.
Susan saw it too. “And you look absolutely yummy sitting there like that, but I think your Master has other plans.”
“Yes, I do. We need to get going. We’ve got to stop at your apartment so you can get your transcript for my friend Tom to review, and I think there are some other things you should take. I’ve also made an appointment with my friend Julie to get a private showing for you so you can select some new underclothes for your role as Tom’s slave.”
“You’re assuming he’ll have me.” Susan said, looking doubtful.
“Why wouldn’t he?” Michelle asked. “If he’s a friend of Master’s he’ll probably jump at the chance.” She winked at me.
Susan shock her head. “I guess I’ve just become accustomed to not expecting much.”
“Well, maybe it’s time you expected more, and took a bit more positive initiative. We’ll help, and I’m betting Tom will help. I do know him, and I think you’re just what he needs, both in his office and at home.” I paused and glanced at Michelle. “On the off chance I misjudged one or both of you and Tom, we might make room for you here.”
Susan smiled at me. “I sure hope you’re right.”
“Susan.” I said sharply. “Approach this as positively as possible. You are a very beautiful young woman and very talented, in the bedroom and out. You’ve done extremely well working hard on your own without falling into the traps that so many young women like you fall into. That says a lot about your ethics and drive. High ethical standards follow directly from strong self-discipline and intelligence. Those things will be critical in your chosen career path, as well as in your relationship with Tom when he accepts you.”
Susan smiled. “The two of you have such confidence in me and you hardly know me. Thank you. I’ll do my best.”
Michelle looked into her eyes. “That smile will work wonders, and what it can’t do I know your body can.” I watched a hand sneak down to stroke Susan somewhere below. The girls kissed again and their hands were busy below my line of sight.
“Okay ladies. We need to get a move on. Clear the table while I get dressed, then get your own shoes and dresses on.” I glanced at the clock. “Fifteen minutes, at the front door, ready to go, or there’ll be discipline later.”
Susan and Michelle smiled, then Susan cheerfully chimed, “Promises, Promises.” She wiggled her hips at me as she walked to the kitchen with Michelle. I shook my head. Tom was going to enjoy Susan.
As ordered, the girls were standing at the door as directed, when I walked out. We went directly to Julie’s shop, unfortunately we weren’t early enough for a repeat of the naked shopping that Michelle had done, but Julie did allow us to lock ourselves in the private back room. She looked at me harshly, “Another one? Isn’t one enough for an old guy like you?”
“Julie, I’d like you to meet Susan, Susan, my dear friend Julie. This is her store.” They shook hands, a bit coolly. “Susan is a friend of Michelle’s and we’re taking her over to meet Tom. She’s studying PP in school and needs a job and someone to help her out with some training.”
“Tom would be the one alright.” Julie smiled. “Okay, young lady, do you,” She emphasized the ‘you’ and looked at Michelle, “Know your correct bra size and hip measurement?”
Susan glanced at Michelle then replied, “Yes ma’am. 32B and 32.”
:Julie said, “That looks right. Do you have any favorite colors?”
“White and pink.”
“Let’s go pick out some things for you to try on.”
Susan started to follow, then held out her hand to Michelle, “Help me, please?”
They walked out hand in hand, and came back a little later with an arm load of garments, giggling between themselves. Julie looked at me, “She certainly has good taste.”
I smiled and Michelle chirped, “And she tastes good!”
Susan blushed and I snarled, “Slave!” Julie just laughed and shook her head.
Julie looked at Susan, and asked, “Have you ever worn this style of bra and or garter belts?”
“No ma’am.”
Julie glanced at me then at Susan, “Well then slip that dress and shoes off and I’ll show you how the first time.”
Susan nudged Michelle for an unzip, then Michelle nudged back for the same. I smiled and they slipped their dresses off together. Julie shook her head and smiled. “I refuse to be the only woman in the room dressed. Rich?” She stepped back up to me and I unzipped her dress. She stepped out of it.
“Okay, Susan, this is what these bars and things look like worn properly.” She selected a lovely pink lace garter belt from the stack and stepped up to Susan. “This is easy, you just wrap it around and clip it, then slide it around so the clip is in the back. The stockings are a bit trickier.” She opened a package and directed Susan to sit down. “They tend to be lighter weight than pantyhose, so you can’t just jerk them on. You have to roll them to start and unroll them up your legs. Like this.”
Susan watched closely as Julie pulled the first stocking into place. I saw a couple of finger brushes against Susan’s pussy and knew what was coming. Julie handed her the other stocking, “You try.” Julie watched carefully as Susan unrolled the stocking up her leg. “Very good, now stand.”
Julie didn’t move back, so Susan ended up straddling her, Julie’s nose almost in Susan’s cunt. Susan stepped back slightly and Julie smiled up at her. “Now, the stockings attach like this. One garter straight down the front of your thigh and the other straight down the outside, like this.”
When Julie finished one leg she had Susan do the other. Julie reached up and touched Susan’s pussy gently. “May I?” She glanced at me then looked into Susan’s eyes.
I said, “Of course, if Susan wants.”
Susan simply breathed, “Yes.”
Julie didn’t need any more invitation. She started licking Susan’s pussy, and her expertise showed quickly. Susan gripped Julie’s head and pulled her closer, Michelle stepped up behind Susan and cupped her tits. Susan took just minutes to squeal her delight and shudder through an orgasm that filled Julie’s mouth with sweet girl juice. Susan was trembling when she pushed back on Julie, she smiled down and said simply, “Thank you so much.”
Julie looked up into Susan’s eyes and replied, “My pleasure.” She looked at me, “We need to do this somewhere that I can enjoy it even more.”
“We can do that.” I replied, considering the possibilities.
Julie stood in front of Susan. “This is how you wear these bras. The bra simply holds your breasts forward, your nipples stay completely exposed. It’s why he likes them, and why I keep a supply on hand.” Julie handed her one that matched and Susan put it on. “These are spectacular too.” She smiled and tweaked Susan’s nipples.
“Okay, Susan. Take them off and you and Michelle can go up front and pay for all this. Michelle, you take care of it on your card.” I indicated the pile on the chair. Julie and I need to talk for a minute.” I watched Susan taking off the bra and garter belt. “And girls, don’t forget your dresses.”
Michelle giggled and they slipped their dresses and went to the register. I turned to Julie, “I know, I owe you an explanation.”
She glared at me. “Yes, you do.”
“Michelle is a friend of my youngest daughter and she had a pretty rough home life. She came to me several months ago and asked for some help and advice. I gave her that and got her through high school, but she needed a safe place to live where her ambitions would be accepted not rejected. Since she wants to follow in my career I decided she could become my assistant. A month or so ago things got worse at home, and honestly, she’s been trying to seduce me for quite a while. I told her absolutely not until she was at least eighteen, so for her birthday she seduced me.”
“I’ll bet that was difficult.”
“More than you might expect, I’ve known her since she was about ten. It was hard for me to think of her as a woman, even when I looked at that body.” I sighed and shook my head. “I don’t know if she planned it or not, or how she could have known, but once she had made love to me she offered to be my sex slave, in addition to my assistant.”
Julie stared at me, “So how could she have found out?”
“I don’t know. There’s nothing obvious around the house, you’ve been there.” I looked at the closed door. “Maybe it was a lucky guess, maybe she just figured something out in the time she’s been coming over to study and for advice.” I shook my head again. “I just don’t know. She sat there on my cock after I’d cum inside her and offered to be my sex slave for as long as I’d have her. So here we are.” I looked at Julie. “We need to meet Tom and do a couple of other errands. I was thinking that you could come over to the house this evening and spend some time with the girls. You might even get them to let you spend some time on me.” I laughed.
“Will there be anything left?” Julie asked.
“God, I hope so. Maybe if they don’t leave any for you I’ll let you beat them?”
Julie’s eyes lit up and she smiled. “Oh god. Don’t make me a promise like that. It’s been so long since I whacked a tight little ass like those two.”
“Here’s a thought. Tom and I are probably going to need to talk privately, if he agrees to take on Susan as his assistant and slave. Maybe you three girls could spend some time together at the house while we get away and discuss some things?” I explained. “What are your dinner plans?”
“Nothing my microwave will care if I miss.” Julie explained.
“Then let’s do that. Assuming Tom agrees we’ll meet for dinner with the five of us, then the three of you can go back to the house and Tom and I can find someplace to talk. That should give you two or three hours.” I grinned. “Do you think you can occupy two or three hours with those two?”
“Is the key to your toy box still in the usual place?”
“Yes.”
“Then I know I can occupy at least that long.” Her hand went between her legs. “God. You’ve got me dripping just thinking about it.” She put her fingers to my lips and I sucked them in.
“You still have a delicious pussy.”
“Then why don’t you spend more time tasting it?”
“I seem to be a bit pre-occupied now.” I grinned. “The only condition, the downstairs playroom is off-limits tonight. Susan hasn’t seen it and Michelle hasn’t seen it in use.”
Julie nodded and the girls returned. “Ready?” I asked.
“Ready!” In unison. “Thank you so much, Sir.” Susan added.
Michelle grinned at Julie. “Don’t forget your dress.”
“Impudent. I am going to like this.” Julie grinned.
We headed out for Susan’s apartment, and arrived a few minutes later. She took the bags of new clothes upstairs and we went in to wait while she found her transcript. Her apartment was small but nicely, if sparsely furnished, and clean. The money she had obviously went towards the bed and desk. She knew right where to find the transcript, and it was an official stamped version. “I got a new one last week. Somehow I knew I’d need one.”
While she searched for some examples of her writing I scanned the transcript. She’d been taking nearly a full class load when she could and still maintained a 3.5 average. The girl appeared to be smart. She found several papers she’d written for recent classes, while she searched for a folio to put them in I scanned a couple. Her writing was clear and precise, and although I didn’t follow all the jargon, her arguments followed logically. The folio she found was a bit battered, but it would do.
“Excellent work, Susan. You seem to be everything I’d hoped for. I think Tom is going to be impressed.”
“Thank you Sir.”
We headed for Tom’s office. On the way the girls sat together in the back and whispered together. I let them. When we arrived I opened the door for them. Susan slid out gracefully and with dignity. Michelle looked at me, grinned and flashed me as she exited. I like that.
We were a bit early so we waited in the lobby while Tom’s appointment wrapped up. As he walked out we rose and went in. We walked up to his desk and he rose. “Tom, my assistant Michelle and her friend Susan. Ladies, an old friend, Tom K.”
Tom stepped around the desk and took Michelle’s hand and shook it gently. His large hand completely covered hers. “My pleasure, Michelle.” Then he stepped to Susan, he looked into her eyes and said, “I am pleased to meet you.” He took her hand in both of his. “You are everything Rich promised and more.” He stepped back around to his chair and pointed to the ring of seats in front of the desk. “Please sit, everyone. Can I get you anything?”
We sat, Susan and Michelle taking care to do so demurely, even with their lack of dress. Susan asked for water, Tom spun to the small refrigerator behind his desk and got one. “You Michelle?”
“Yes please Sir.”
He got another and handed it over. “Tom, I thought that we’d step out front and allow you to interview Susan as your assistant first, then, if you think she’ll work out, we can come back and we can all discuss the other arrangement. Would that be alright with you?”
“Rich, that’s a great idea. Then, if you’ll excuse us, this may take a little while.”
“We can find something to talk about.” Michelle and I rose and went back to the lobby. We sat and talked about expectations and what I thought about Susan’s chances.
“Honestly Michelle, if I know Tom, Susan is just what he needs, both here and at home. I expect she’ll make an excellent impression and she’ll get both positions.”
“I hope so.” Michelle continued. “I really like her and I think she just needs a break to really make something good out of her life.”
After about twenty minutes Susan opened the door. “Would you please come back in and join us?”
We went in and Susan closed the door. Tom began, “I’m very impressed by Susan, and although it was a chance meeting between you, it seems that it was very fortunate for all of us. I have asked Susan to start as soon as possible helping me with my office work and doing some preliminary interviews for me with clients and potential clients. Her education and background lead me to believe we can do very well together. I can’t pay her as much as she would deserve, but I am willing to work with her and teach her in exchange for her services.” Tom paused and looked at each of us, and sighed. He held up some papers that had been laying on his desk. “Now, Rich, you sent me a copy of this contract that you wrote for you and Michelle and suggested that it might be something that Susan and I should consider.” He looked at Susan. “Have you seen a copy of this?”
“Yes Sir.”
“What do you think of it?”
“I read it and I think that for a young woman who found a decent, fair-minded older gentleman to take care of her, lovingly and respectfully, but firmly, it would be a very good deal.’ She looked at Michelle. “I think if I found someone like Michelle did Rich, someone established, intelligent, respected in their profession, who would be willing to teach me and bring me up properly where their profession matched my goals and they would keep me and take care of me and train me in self-discipline, ..” She paused and looked thoughtfully at Tom. “I think if I found someone like that I’d hand him a signed copy of the contract so we could get started as soon as possible.”
As Susan said this last she had opened her folio and when she finished she laid a copy of the contract on Tom’s desk in front of him. I could see her signature already on the last page. Tom looked at it and smiled. “I think it would be in my best interest to sample what’s being offered before I sign. What would you say to that, Susan?”
Susan stood and looked at him calmly. “I think that’s an excellent idea. Michelle?” She looked down. “Would you unzip me?”
Michelle jumped up and pulled down the zipper on Susan’s dress. Before Susan could remove it Michelle stopped her. “Me too?” Then she looked at me. “Is that okay Master?”
“Absolutely!”
Susan whipped Michelle’s zipper down and they stood facing each other. Michelle leaned up and kissed Susan. “Do your best.” And they stepped back, each sliding the dress from the others’ arms. They stood there for a moment, naked, admiring each other, then they turned to Tom. Michelle said, “I present your potential slave, Susan. Isn’t she yummy?”
Tom laughed. “You both look yummy to me. But I think I need to taste for myself. Susan, would you come around here, please?” Tom looked at me while she circled the desk. “Rich, I don’t know how you do it.”
“Dumb luck.” I replied.
Susan reached Tom and stood in front of him. The impressive bulge in Tom’s slacks told me he was impressed. He stroked Susan’s hair gently, “I’ve dreamed about a woman like you , but never in my wildest dreams have I thought that she would make me an offer like you have. Hop up here on the desk, I want to taste that sweet pussy.”
Susan did, and Tom sat down and stuck his face between her legs. Susan moaned as did Tom, and she lay back on the desk, looking back at Michelle. Michelle stepped closer to the desk and they held hands as Tom paid tribute to Susan’s pussy. Shortly Susan moaned out, “Oh god! Yes!” Tom’s slurping increased and I realized she’d squirted her cum into his mouth.
As she lay there panting and recovering Tom sat up. “A delicious little squirter. That was a pleasant surprise.” He held out his hands and Susan took them. “Now it’s your turn. Kneel down here and show me what you can do.”
Susan slid off the desk and onto the floor. She reached up and unzipped and unbuttoned Tom’s slacks. She slowly worked them down past his hips, so that his erection held them up. She pulled the front of his pants away and they dropped past his cock, which swung up and smacked her cheek. As the only one who had seen Tom’s erection, I knew what to expect. The girls were very surprised. Tom’s erect cock is fully ten inches long, but even more impressive is the girth. It tapers slightly out from the root to nearly three inches in diameter at the head. Susan reached up and grabbed it and held it longingly in her hands. She looked up at Tom and said, “Whatever you decide, thank you.” Then she stretched her mouth wide and slid that monster inside.
As soon as she had swallowed the head Tom moaned. “Oh god. It’s been so long since I’ve been in someone’s mouth.” Susan slurped around his cock and he moaned almost continuously. After a few minutes she sat back and looked up at him.
“Sir, I think you really need to test my pussy too.”
Tom looked down and stroked her face. “I think you’re right, but how will we clean up afterwards?”
Michelle immediately said, “I’ll clean her pussy and she can clean your cock.”
“Then get back up here on the desk.” Susan hopped up on the desk, grinning. Tom stepped up and rubbed the head of his cock against her pussy lips. “Are you sure? You look so tiny.”
“Make it fit, please?” Susan really wanted this. Tom pushed and she moaned as he opened her cunt with his cock.
“Am I hurting you?”
“No. Please? More. Please! Put it all in me.” Michelle was back holding Susan’s hands. Tom slid his cock in slowly, fearful of hurting Susan, but Susan seemed happier the more of that monster that stretched her insides.
Tom paused and said, “It’s almost in, can you take any more?”
“Yes. Please Master, give it all to me.” I saw her close her eyes and grip Michelle’s hands. Tom pulled back partway and tensed himself, then drove forward and buried that entire cock inside Susan’s tight little pussy. She moaned and pulled on Michelle’s hands then whispered, “Thank you Master. Is it all in now?”
“Yes, you’ve got it all. Thank you. How does it feel?”
“It feels wonderful. Would you hold it like that for a moment, then fuck me and give me your cum? Please Master?”
“Yes Susan. You can have it.” Tom smiled. “Tell me when you’re ready.”
I could tell by the look on Tom’s face that her cunt was spasming on him while she adjusted to being so totally filled. After a minute she opened her eyes. “Fuck me, please, Master.”
Tom obliged. He slid himself in and out, slowly at first, but it had been a while since he’d been laid, so he wasn’t going to take long. Very soon he moaned, “Oh god! Here it comes baby! Here’s my cum for you. Oh! God!” he pushed in so hard that he slid Susan on the desk. She screamed in pleasure as he filled her. I watched his face as he just kept shooting his cum into Susan’s waiting pussy. She smiled widely as he filled her even fuller. Finally Tom twitched a few times and leaned forward over Susan and looked into her eyes. “Thank you so much.” He whispered. “Whatever happens from now on. Thank you.” He kissed her tenderly and they smiled at each other. He leaned to the side, picked up the contract form that Susan had signed and lay it on her belly and signed next to her name.
Susan looked up at him and smiled widely. “I guess this means that I’m your slave now. Master.”
Yes, it does, slave. Are you ready to fulfill the rest of the deal for now?” He looked at Susan and then Michelle.
They said in unison, “Of course.” And Michelle went to Susan’s pussy while Tom pulled out and walked around to Susan’s head.
Michelle sat on the chair and slid up then looked at Susan. “My god girl, there’s cum everywhere!”
“That’s how it feels baby.” Then she saw Tom’s semi-erect cock hanging over her face, still dripping strings of cum. “Looks like he brought me some too.” She grabbed Tom’s hips and brought his cock to her mouth, opened wide and sucked it in as Michelle licked her clean below. It took Michelle a while, there really was a lot of cum. Susan had Tom nearly hard again before he finally pulled his cock away. She whined low as he stepped back.
“God baby. I wish I had time to let you finish. I’m not sure which is better, your mouth or your pussy, but I intend to find out.”
Finally Michelle raised up. “Baby, you’re clean where I can reach, but I think we’re going to have to wash the desk. You two made a mess!”
“As long as you cleaned inside so I smell good for my new Master later.” Susan giggled.
Michelle wiped cum from her face and into her mouth. “I did that.” She looked at Tom. “Sir, where can we finish cleaning up?”
Tom looked at the girls as they stood up. He smiled, “Down the hall left, third door.”
He started to object as they darted out the door with their dresses in their hands, but they were already gone. Somewhere he’d kicked his pants and shoes off, he sat down in his chair and seemed to contemplate putting them back on. He looked at the top of his desk and smiled, wiped his fingers through the liquid and sucked his fingers. “She is tasty, if a little messy.” He smiled. “My god man! Did you see that? That little tiny girl took my entire cock in her pussy. I’ve had grown women cry and whine when I pushed the whole thing inside them and she begged for all of it. I thought I was going to tear her in half, and all she did was have a screaming orgasm.” He smiled and shook his head. Then reached down for his pants and started pulling them back on. “And now she’s my sex slave? After what I’ve been through the past couple of years I don’t know what to say or do.”
A frown crossed his face. “How am I going to provide everything that’s in that contract Rich? You know the bitch bled me dry. I can pay myself now, but I’m just back on my feet. I took that bigger townhouse, but I haven’t even finished furnishing all the rooms. What did I just do?” He stood to finish his pants.
“Tom, you just did the smartest thing you’ve done since you kicked the bitch and her cheating slut ass out. Even with what it cost it was a bargain.” I looked at him and he nodded while he put his shoes on. “Now you’ve just done two smart things, you’ve hired a beautiful young woman whom you can mold as your right arm here, so you’ll more than make up whatever it costs, and as your slave you can pay her in room and board and other things.”
Tom thought that over and agreed. “You’re right, part of the problem is getting all the paperwork straight and clients in the door. Susan will help with all that, and she’ll still learn a lot.”
“Tom, look at me. As for the rest, let’s you and me have a long talk over scotch tonight. Julie is going to join the four of us for dinner, then I’ve promised her that she can entertain the girls while you and I go out for a couple of hours.”
“Do the girls know? I mean about Julie?”
I laughed. “Only a little, I’ve bought each of them some lingerie from her shop and she went down on them while she was “showing” them how to wear it. But they’ve never been alone with her.”
“Should we tell them?”
“I don’t intend to tell Michelle, part of the contract says I have the right to share her with friends, and I certainly don’t want her to think that we’re exclusive. You can do what you think is right with Susan, she belongs to you.”
“No, you’re right. She needs to get some experience with some of our friends. Where for dinner?”
I told him and he whistled. “It’s okay, this is on me. We’ll meet you there, you can pick Julie up on your way, and she can take the girls home in my car while we talk.”
“Thanks Rich. For everything.”
The girls bounded in the door, dresses on this time. “Okay Master, we’re ready.”
“Okay. Ladies. Tom has a number of appointments this afternoon, so we’re going to let him work, since he doesn’t have time to train Susan before the next one. So we’re going to do some shopping, then we’ll meet him for dinner about six.”
At six we pulled up in front of the restaurant. Tom met us at the door with Julie. The five of us went in and we were seated at the table I’d requested. Dinner was uneventful, at least after I told the girls that they were going home with Julie so that Tom and I could talk. Michelle and Susan were better once I’d ordered wine for the table and everyone had some. I called for a pause in conversation and offered a toast to Susan and Tom, “To new beginnings and happy endings.”
We had a marvelous time, and spent nearly two hours over our meal and wine. Finally we finished and I called for the check. Tom still started to object but I cut him off. “Tom, this is a celebration for you and Susan and it is on me. Julie, here’s the keys to my car. Enjoy yourselves. Ladies, remember who you belong to, and that Julie is your Master for this evening. You are to treat her as a Master, and do as she says. She may discipline you if she finds it necessary. Questions?”
I looked at the girls. “Michelle?”
“No Master.”
Tom asked, “Susan?”
“No Master.”
“Julie, enjoy yourself. They’re yours until we get home.”
Julie just said, “Thank you.” And grinned as she herded the girls out. Tom and I retired to the lounge for a discussion. We took a quiet booth and ordered good Scotch, neat.
I started the conversation, “Tom, I know you’re not quite where you need to be financially to take Susan on right now. But you know you don’t have to worry. I’ve already bought a bunch of clothes, and will buy the rest, just because it’s the right thing to do. You know that or you wouldn’t have signed the contract this afternoon.”
Tom laughed, “Yeah, but it would have been harder to resist if I hadn’t had my entire cock and a load of my cum inside her pussy when I did.”
“But even at that, you knew this was a once in a lifetime opportunity. It may work out long term, it may not, but Susan will give you two things you need desperately. A beautiful young assistant who will do whatever grunt work you need done in the office. And maybe more importantly, a beautiful young naked woman around your house to fuck you stupid every night and make you forget the bitch that fucked your entire life for two years.”
“Yeah. Fact is, I need both of those. You’re right. Dammit. I suppose that’s what friends are for. How did you know we’d be such a perfect fit?”
“Just a lucky hunch. We were sitting talking this morning and when she described her life and her college plans I thought of you immediately. Of course, having fucked her, I never guessed you’d get all that thing inside her. Hell, she was tight on me. I’m not sure where it all went.”
Tom laughed. “I’m not sure either. It was like she was hollow. Except that she was squeezing me the entire time, but she took it all and acted like she could have taken more.” Tom shook his head slowly. “Regardless, it was still the best fuck of my entire life, and that’s saying something.”
I laughed. “Yeah, I’ve seen you get pretty well fucked, and I’ve never seen the look on your face that you had when you came inside Susan this afternoon. I know I was impressed last night, and I couldn’t come anywhere near filling her like you did.”
“Poor you!” Tom laughed. “I guess if you have lots of money you don’t need a big dick.”
“Even with lots of money you know I’ve gone quite a while where I didn’t see much pussy.”
“Looks like that’s going to change.”
“Looks like for both of us.” We laughed and made a toast of that. I continued, “I know the girls are hoping to still get together regularly, it seems they like pussy almost as much as they like cock. You won’t mind, will you?”
“Let’s see, bring my slave over to watch her eat your slave’s pussy, then I assume we exchange slaves for some old-fashioned fucking?”
“I’m guessing something along those lines, yeah. You won’t mind fucking Michelle for me once in a while will you?”
“Oh god no.” Tom laughed. “She’s not very big, but she seems to have a big appetite.”
“That she does. Although I’m not sure you’ll get that thing completely stuffed inside of her. I’m not sure she can even get the head of you in her mouth. But it won’t hurt to try. I’m looking forward to watching.”
“I’ll bet you are.” Tom grinned at me. By now we were on the third Scotch. “Anyway, you say Susan has an apartment?”
“Yes, nice furnishings, although not a lot of stuff. I didn’t check her clothes, but I’m guessing that it’s mostly jeans and t-shirts, so she’ll need a new wardrobe. I took Michelle to Karen, I’m assuming I’ll do the same with Susan for you. You can sort out what you want her to wear from what she has and we can go from there. No underwear doesn’t really save a lot on the clothes budget I’ve noticed.”
Tom chuckled. “Yeah, but naked around the house will be pretty easy to get used to.”
“I discovered that after a few hours I hardly noticed, and it didn’t seem to bother either of the girls earlier. Anyway, the two of you can go through Susan’s things and decide what moves and what doesn’t. Then we can all get together with my truck this weekend and move her in. For now all she needs is what clothes she needs for the week at your office.”
“Too bad I don’t have a home office like someone I know. She wouldn’t even need much for clothes when she worked.”
“A fringe benefit, my friend.”
We thought better of trying to drive and caught a cab to the house. We walked in quietly, fortunately a little more sober than when we left the bar. The lights were on and the girls dresses hung in the front closet. Julie’s dress was over a chair in the living room, so we opened the bedroom door quietly and stepped in. Julie was in the middle of the bed with a girl on each side cuddled up against her. As we circled to the foot of the bed I realized that each of them had a butt plug in, and a hand on Julie’s favorite strap-on dildo that she kept in my toy chest. Since they were all asleep Tom and I crept on through to the bathroom and stripped off our clothes quietly. We went back in and looked at them lying there. The girls’ asses were red, as though they’d been pretty soundly paddled, and the paddle was still on the foot of the bed. It looked a lot like what I’d expected from Julie, I guessed the girls had gotten an education tonight.
We looked at them for a minute while our cocks stirred to life. I touched Tom’s arm and pointed towards the side of the bed where Michelle lay with her head on Julie’s chest and a nipple next to her mouth. Tom smiled and nodded and mouthed “Thanks” and went to that side. I went to Susan’s back. We started to climb into bed and Julie awoke.
Julie looked at us and shook her head. “No you don’t. I think I wore them out. I hope so. I need some real cock, and here it is. Help me slide out of here so you can fuck me.”
We knew Julie well enough to do what she said. We helped her rearrange the girls so she could climb out of bed. She unstrapped the harness and set the dildo in the toy chest. She turned and said simply, “Come here you two.”
We walked over and she took a cock in each hand and kissed us in turn. “Let’s go somewhere else and get these inside of me.” Julie pulled the bedroom door shut gently as we walked out, then, as we walked past the couch she pushed Tom down. “Oh hell, this is good, I need cock.”
She knelt on the couch over Tom and guided his cock to her pussy. She simply got him lined up and sat down on him, taking his entire cock in one move. Tom gasped, but Julie just said, “Oh god. I needed that.” She looked back at me, stroking myself and said, “What are you waiting for? You’ve got a hole to fill, get to it.”
I stepped up and rubbed my cock around her asshole and discovered that she was already lubed. I decided not to ask, I just put the head of my cock against her sphincter and pushed. I slid in slowly while Julie relaxed against Tom. When our hips touched Julie sighed. She looked back at me and asked, “Ready?”
“I am.” And I started fucking her ass. Tom moved a bit to help. It didn’t take long for Julie to decide she was having a great time. We all built up speed as our orgasms approached, Julie tipped over first.
She started moaning, then got louder and more vocal as we hit the right spots. Then Tom got close and started moaning too. They started cumming together, Julie screaming out, “Oh god! Yes! Yes! Fill me up! Fill me with cum!” And Tom grunted his own pleasure deep inside. I followed quickly, shooting all I had deep in Julie’s fine ass.
With all the noise we were making, and the pleasure we were getting form each other, we didn’t hear the bedroom door open. We were hugging and kissing each other in shared bliss when I heard two soft voices say, “Master!”
Tom and I turned our heads and looked at our new slaves. “Yes?” I added, “Do either of you have the mistaken impression that we belong exclusively to you? Your bodies belong to us, to use or share, but our bodies do not belong to you and we will share as we choose. We shared you with Julie this evening and now we’re sharing Julie for a while, as we have in the past. You can watch quietly or you can go back to bed, but one word until you are spoken to and there will be serious discipline administered. Is that clear?”
“Yes Master.” They both said. They looked around and selected the loveseat near the fireplace and sat close together, watching.
I looked at Julie and Tom and asked, “Is anyone else ready to change places for a while?”
Julie looked at me and gave me a kiss. “If you want to pull out you can, I’m going to sit here and enjoy this monster for a few minutes, then I think I’m going to clean it up.” She smiled at Tom. “You won’t mind, will you?”
“Not at all.” He replied as I slipped my cock from Julie’s ass. A little of my cum trickled out and ran down across Tom’s balls as Julie clenched shut. As usual, she was clean and I wondered if she’d shown the girls what she knew. I sat on the couch next to Tom as Julie wiggled around on his cock.
She looked into his eyes and whispered, just loud enough for me to hear, “Think you two can get up for some young ass soon?”
I looked at my cock, it was resting peacefully, but twitched at the realization of what Julie was suggesting. I replied, “It’s going to take a few minutes, and maybe some help, but I can get another round.”
Tom didn’t say anything, Julie just looked into his eyes and said, “It must have been longer than I thought for you, you’re not going down at all.” She looked over at the girls, “Your Master needs some help getting his cock ready for another round of ass, get your mouths to work. Now!”
Susan and Michelle jumped up as one and came to me and knelt by my feet. Michelle leaned in first and took my cock in her mouth. I responded almost immediately to her sweet mouth. She really is very talented. Susan leaned in and they mouth wrestled around my cock. In minutes I was hard again. Julie looked down and said, “Alright, kneel up here on the couch, one on each side of me.”
They did, and Tom and I looked on appreciatively. Julie told us, “Okay, if I understood correctly,” she looked at me, “you’ve had both pussies, but only Michelle’s ass. Right?”
“Correct.”
“Then Tom, you get to choose which ass you want, since you’ve only had Susan’s pussy.”
The thought of Tom’s monster cock up Michelle’s tiny ass made my cock throb. I hoped and waited until he said, “Well, since I haven’t had any of Michelle, I’ll take her ass, and Rich can try Susan’s.” I wondered if he heard me thinking.
I stood up and went to Susan while Julie slipped off of Tom’s cock. He really was still hard. He stood and stepped up to rest the head of it on Michelle’s ass. Julie looked and said, “Okay boys, plugs out and cocks in.”
I pulled the plug out of Susan’s ass and slowly slipped my cock inside. She was snug but relaxed. I asked, “Have you done this before?”
“A few times, but I never liked it.”
“You will.”
We turned our heads to watch Tom with Michelle. We could see the fear in her eyes as Tom pulled the butt plug from her ass and laid the head of his cock against her anal ring. He said, gently, “Baby, I’m going to go real slow, but you’ll have to relax or it’s going to hurt. I am going to fuck your ass, and I’d rather not hurt you, so, easy and relaxed.”
Michelle nodded and whispered, “Okay, go ahead.”
Tom pushed gently and Julie squeezed a bit of lube around his cockhead. Michelle winced as Tom pushed and I could see her anal ring begin to stretch. He kept the pressure up and she opened slowly to accept his enormous width. I could see a tear run down her cheek, but she remained silent. It took several minutes, and if it seemed a long time to me I could only imagine what it seemed like to Michelle as that enormous cock forced her open, but finally she was open wide enough and the head of his cock popped inside. She couldn’t remain silent and she cried out then “Oh god, it hurts!”
Julie held her head and kissed her. “Hold still baby, the worst is over now. He’s got the head inside you, the rest will be easier. I promise.” Julie kissed away the tears streaming down Michelle’s face. Michelle nodded. Julie said, “Let us know when you’re ready for him to push in again. Just relax and hang on.”
Michelle smiled at that, then nodded and whispered, “Okay.” She ducked her head and Tom pushed gently. It really did seem to go easier then. A few moments later Tom’s hips met hers and he stopped.
“Okay Baby. You’ve got it all. Are you okay?”
“Yes. Just give me a minute before you fuck my ass. Please Master?”
“Absolutely. Tell me when you’re ready.”
I couldn’t wait. Watching Michelle take Tom’s cock up her ass had me throbbing, and I started fucking Susan’s ass while we watched and waited. I reached around and fingered her clit while I pumped her ass, and she was getting very wet. Michelle held Tom inside her for a couple of minutes while she adjusted. I saw Tom enjoying the sensations of her ass clutching at him while she got used to having something that big plunging up her butt. She finally was ready and she looked at me, then Tom, “You may fuck my ass now Sir.”
Tom gripped her hips and started slipping in and out of her ass. He also reached around and rubbed her clit. It took only a couple of minutes before Michelle responded positively to the ass-fucking and rubbing he was giving her. Susan was pounding against me, encouraging me to fuck her ass hard, Michelle was a bit more restrained, but still clearly starting to enjoy having Tom in her. Tom was obviously enjoying himself too. The four of us were racing forward to more orgasms, the girls slightly in the lead. Tom’s big hands were on Michelle’s clit and pulling at her nipples and it was working for her with his cock in her ass. I was pulling Susan’s nipples and rubbing her clit and that was working with my cock in her ass to get her going strong. I was taking a long time to build, having recently cum in Julie’s ass. But truth is, pounding into Susan’s ass while watching Tom’s huge cock pounding Michelle’s sweet little ass next to me was turning me on.
Suddenly Susan stiffened and screamed, “Oh yes, baby! Yes! I’m cumming, cum with me!”
I pounded her hard and felt her ass squeeze my cock as she came, and it sent me over. “Oh yes. Here it is baby. Here I cum!” I grabbed her throat and pulled her body back against mine while my cock filled her ass. She grabbed my head and we moaned into each others’ ears.
Our sounds tipped Tom and Michelle over the edge and they started screaming together. Michelle screamed at Tom, “Hold me Master! Hold me while we cum! Oh god. Hold me.” Tom looked at how I was holding Susan and grabbed Michelle and pulled her tight little body against him. He moaned as his cock shot her ass full. Julie sat on the couch and watched the girls hanging on our cocks as we shot their bowels full. She was obviously delighted.
I watched as Tom’s legs started to quiver and he spun around and sat down on the couch, driving his cock hard into Michelle’s ass. She moaned but sat happily impaled there. She leaned her head on Tom’s shoulder and kissed him. “Thank you Master. After the pain that was wonderful.”
Susan kissed me and said, “Thank you too Master. I enjoyed that a lot. You can fuck my ass anytime.”
I laughed. “Any time your Master allows, anyway.”
Tom looked up and smiled. “What’s mine is yours my friend. And of course we can always share with each other. I never expected to find one more woman who can take my cock, you’ve found two. I think I’m in heaven.”
“No, you’re in my ass.” Michelle giggled and kissed him again. “Maybe it’s close, but I think heaven is probably Susan’s pussy.”
Tom laughed. “I’ll be honest, heaven is any woman who can take my entire cock in any opening. You’re both heaven.”
Michelle looked at him, and smiled. “I want to try it in my pussy too.” She winced when Tom’s cock twitched. “But not tonight. Please Master. I don’t think I can take any more cock tonight.”
Tom laughed. “You can climb off whenever you want.”
“I’m almost afraid to.” Michelle replied, honestly. “How about if I slide off slowly and you just help me stay steady?”
“I can do that.” Michelle slipped forward, and drew Tom’s length out of her. I was slowly shrinking inside Susan, but I held her close so I didn’t fall out of her ass. It was easy to tell when the head of Tom’s cock re-stretched Michelle’s ass, as she stopped and winced. Tom held her hips and assured her. “Steady baby, you’re out at the end.”
Michelle smiled. “I know. Here we go.” And she stood up as Tom popped free. She staggered a bit as her sphincter contracted, but not before her ass gushed cum onto Tom’s legs. She reached out for Susan. “Come with me baby, I need the bathroom?”
Susan looked back at me, “Is that okay?”
“Sure.” I slipped her forward and popped my cock out of her ass, without quite the mess that Tom and Michelle made. The girls made a bee-line for the Master bath. Tom and I chuckled as they left, but Julie glared at me. I tried an innocent “What?”
Julie’s reply was simple, “Cum enema?”
“Oh, you heard about that.” I replied, a bit sheepishly. “It was my last wife’s term, and well, the whole thing sort of came out of nowhere, and just happened.”
“It shouldn’t “just happen” and you know better, and now those two young women do too.”
I looked at Tom, “We should go get cleaned up ourselves.” We followed the girls and headed for the bath, we heard them talking as we approached.
Michelle said, “I thought he was going to rip me in half at first, and when the head of that big thing went in my ass I thought he had. For a minute I thought I was going to have to scream it hurt so bad, but once I managed to relax it actually started to feel good, and then it felt great. If you know what I mean?”
“I know exactly what you mean.” Susan replied. “I felt sort of the same way when he put it in my pussy this afternoon. At first I thought he was going to rip me open, but once he got in it felt so good and full inside. I’m not sure where he put that whole thing in my pussy though. God, it’s huge!”
“I felt the same way tonight with it up my ass.” Michelle said quietly, “But once it was in me it felt so good. Can you imagine what Julie must have felt like with both of them in her like that?”
“I’ll bet we get a chance to find out one day soon.” Susan said.
“Oh, I never even thought about that.” Michelle said. “Of course that means that we get each other too. That’ll be good.”
Susan said, thoughtfully, “I’m guessing we’re going to get all the sex we want from now on. Rich and Tom seem to have a lot of friends, I’m guessing we’ll get to know quite a few of them, and either of them could keep a girl busy.”
We heard Michelle swear. “God, I’m not sure my ass will ever go closed again.”
Susan said, “Oh don’t be silly.” Then Tom laughed and gave us away.
“What?” They shrieked together. Then Michelle said, “Our Masters have been listening to us.”
“Yes, we have.” I said as we stepped into the bathroom. “And yes, it will close, but after Tom it may take a little while, wherever he puts that thing. And yes, it’s nearly certain that if you both behave yourselves you’ll get both of us at the same time one day soon. And finally, yes, we both have a lot of friends, and we’re going to be very happy to share the two of you with them, just as we did with Julie tonight. But first, the two of you need to learn a little discipline, which we will happily administer as needed.”
Tom added, “Precisely correct. I sincerely hope it doesn’t turn out that we actually have to punish them, although I can see it could easily happen.” Tom glowered for effect. “ Especially with my head-strong slave. Now it’s time for a shower and bed. Everybody in.” He opened the shower door and called for Julie to join us.
With three shower heads we got clean and played for quite a while, but finally started filing out to dry and head to bed. There was a lot of good natured play, but we had all reached a point where there just wasn’t going to be more sex, at least until morning. I brought a couple of bottles of wine to the bedroom, with glasses, and we sat in bed and talked and cuddled. Julie had selected the middle and asked for the girls at her sides, Tom and I took the outside positions, next to our respective slaves. Michelle dozed off first, cuddled against me and snuggled back against my body, Susan was slightly behind her in falling asleep. I was glad for the oversized bed, so the five of us could sleep comfortably even stacked closely against each other.