Starting Over

[wickedpen]

"Goodness son, I need a clipboard to keep track of all your desires" she said with a laugh. "I will see what i Can do but there won't be much for me once those young things get a hold of this"s he said emphasizing this with a grab of his semi hard cock.

 

[BeachBum25]

"Emma, you know that you have captured a special place, and when you arrange things for me I am going to repay you. I will give you everything and anything you want... whenever and wherever you want it." Michael leaned down and kissed her again as she gripped his semi-hard cock.

He sat down on the deck his legs in the hot tub. His hands caressed Emma's big tits as their kiss lingered. He was thoroughly enjoying her company and he hoped that she was enjoying his. He broke the kiss. "Emma, what can I do for you? What can I do to truly satisfy you?"

 

[wickedpen]

"Oh Darling, you are doing it. Having a young man like yourself even flirt with me is a thrill these days. To know you will fuck and cum for me, woow! that is hot!" she said with a big smile. "Now I think I need to make some calls to arrange those ladies you would like to enjoy." she said with a sparkle in her eyes.

"Susan's granddaughter" she said looking off trying to remember something, "Kate! Yes that is her name and I believe she just graduated high school. Looks just liek Susan, petite, blonde through and through. You dirty dog" she said winking and smiling at Michael. "Susan said something about her coming down soon for a visit and relax before college." Emma said as her hand felt Michael's cock throb with life. "We may need to work on Heather is this endless hard on persists." she said with a smile.

She got up from the tub and walked to a phone on the wall and picked up the receiver.

"Hello, Heather? Oh Good it's Emma at 178, yes fine and you darling?" Emma's aid making small talk which reverberated off the tiles walls. "I was thinking about buying another unit for my sister and wanted to talk to you about that. No, no, I want you to have the commission, not Nick." she said turning and smiling at Michael. "Yes, so come by tomorrow, around 10? Great. See you then. bye" she said and hung up the phone.

"So I hope you are not busy tomorrow?" she said with a smile.

 

[BeachBum25]

Michael watched as Emma got up from the hot tub and moved to the phone. It was very obvious that she was a woman that was accustomed to getting what she wanted, and she would settle for nothing less.

He listened as Emma spoke to Heather and made arrangements for her to visit tomorrow. Michael smiled at Emma. He also wondered how she was going to manipulate the situation once Heather was there, but he trusted Emma.... she got what she wanted.

When she returned from her phone call, Michael stood up and kissed Emma. "I am certain that I can make time in my schedule tomorrow morning." He caressed Emma's breasts and looked into her eyes. I think we will have a great day again tomorrow."

After saying goodbye to Emma, Michael went home. He walked into the house and said hello to his mother. Then, he went to his room and undressed. He wrapped a towel around himself and went into the bathroom and got into the shower.... the hot water beating on his body.

 

[wickedpen]

It was killing Amy to see Michael not even the slight bit interested in her. Not a slap on the ass, a look down her low cut blouse.

"Emma must have really done a job on him" she thought as she finished the white wine she had been drinking. She decided to check on him. She walked upstairs and stood outside the door, so incredibly turned on she began pinching her nipples. She tried the door and it was unlocked.

She smoothed her blouse and ran her hands down over her skirt, briefly pressing on her mound.

"What have I become?" she thought to herself then the image of Michael naked and the feeling of his dominance washed over her like a tidal wave over a sand castle.

She lightly knocked and opened the door into the steamy bathroom.

"Michael do you need anything?" she said with a flash back to when he was younger. She looked into the mirror hoping to get a glimpse of him naked in the glassed in shower but the mirror was too foggy.

Her hand came to her throat as she nervously stepped in further.

 

[BeachBum25]

Michael heard his mother at the door and then saw the door open as he stood in the shower. He smiled to himself. She needed him and there was no way for her to deny it. She couldn’t stay away.

“Why do you have clothes on, slut? I thought I made it perfectly clear that when we are home that you are to be naked. I walk into the house and I see you with clothes on.... that says to me that you are not interested in the deal we had. So, that is fine with me.”

He continued to allow the hot water to beat down on him for another moment as he waited to see if there was a response. Then, he turned off the water, toweled off and stepped out of the shower.

 

[wickedpen]

Amy was horrified. The maintenance man had come half an hour ago to fix the light in the garage.

"I am so sorry Michael:" she said as fear shot through her. She started to explain as she unbuttoned her top and slid the pants off with her panties and threw them towards her bedroom. She stood at the door hoping he was not too mad as her nipples grew hard on her breasts.

 

[BeachBum25]

Michael watched as his slutty mother furiously undressed in the doorway to the bathroom. It was at that moment that Michael realized that his mother was truly HIS. Previous to this, he thought she was just playing the game because she enjoyed a submissive role; now he knew she belonged to him.

“I am pretty hungry. I haven’t eaten all day and Emma really wore me out today. Do you have something for me? Then, maybe we can take about your wearing clothes when you were not supposed to .”

Michael walked naked past his mother. As he passed by her he smacked her ass.... HARD. He looked back and could already see his handprint on her ass. He smiled and kept going to his room. “You can bring my food up here to me.”

 

[wickedpen]

Amy hurried downstairs and put together a sandwich and some grapes and a glass of his favorite beer. She brought it up on a tray. If she had thought about it, she might have hesistated or not done it at all but honestly it was the most fun she had had in years.

Bringing the tray up she walked into his room and asked "where would you like it?" Her nipples were rock hard and she was as excited as she could be standing wth the tray awaiting her instruction.

 

[BeachBum25]

Michael laid down on his bed and picked up his phone. He went through his texts, which he had not done for several days. Most were from co-workers. However, there was one from Carol. She was asking what he was up to and would he be able to see her soon. He smiled to himself and decided not to respond yet.

He saw his mother come into his room with the tray with food on it. He rock hard nipples were evidence that she was extremely aroused. She obviously wanted something from her son. “Bring the tray over and sit it on the night stand, slut.”

Watching his mother obey him like she did brought a wicked smile to his face. “It is very obvious that you want something. Tell me what you want slug and tell me why I should give you what you want. Convince me and maybe ..... just maybe.... I will give it to you.”

 

[wickedpen]

Amy's eyes dropped submissively as she did want something. She did as he asked and sat on the bed next to her grown son. She could not look at him and did not know if she could form the words to ask for what she wanted. Finally she managed to look at him. He was handsome and she loved him.

"I want to watch you" she said her eyes watering with need. What if he refused, rejected her?

"I want to watch the other women please you baby" she said impassioned. "I want to know all the things you like and how they please you so I can." Her tone was desperate and pathetic but all said with her deepest love for him. "They don't have to know. I could watch through a window or a camera?" she said desperate to keep him from saying no.

 

[BeachBum25]

Watching his mother as she lowered her eyes and asked for her to be able to watch him with other women showed to Michael just how much she was surrendering herself to him....... TOTALLY.

“How would you like to watch me with one of your friends while I fucked her in your bed? Would you like that, slut? Would you like to see me fill and cover her with my seed and shoot some of it on your sheets? Would that make you happy?”

Michael saw his mother sit up and he could tell by her reaction that she liked what he said. “If you like that idea, invite Susan over and I will pretend that you were called away. I will invite her in and get her into your room and fuck her brains out. You can watch from your closet. That is unless you can convince her to let you sit in the chair and watch.”

 

[wickedpen]

Amy was very happy Michael was agreeable to her desire. She had thought of this since she had seen him when he was young play with himself. She remembers the perverse thrill it sent through her as she watched him orgasm. Now as a man, who was so dominant and powerful and had showed her his dominance she wanted to be his witness. She had thought of this for some time and it was not as simple as sitting in a closet.

"Susan will be perfect" she said quickly unable to quell her excitement. "But, if it is OK with you" her eyes again dropped to the bed. She realized her nipples were stiff as bullets with excitement. She raised her eyes to him and put her hand on his leg.

"I want you to force me to watch," she said quietly, nervously. "I want you to tie me to a chair in the room." she said as forming the words alone were nearly enough to send her into orgasm. Her eyes were eager and hopeful he would agree but it was asking a lot.

"You don;t have to," she quickly tried to dismiss her request. "It's silly" she said taking her hand back and almost turning away from him completely.

 

[BeachBum25]

“YOU want? Since when do you make demands? You don’t get to determine what will happen. You need to know when it is time to keep your mouth shut. I might have given it to you if you asked instead of demanded.”

Michael watched his mother’s reaction. Her nipples were still hard, but her eyes were down. She was definitely aroused but obviously realized the mistake she had made. She had to understand that although she was his mother, she was truly his slut.

Michael got up from the bed and walked toward the door. I will be in your bed, which is now my bed. When you have realized the error of your ways, you can come to my room and apologize and if you apologize correctly, I may have a place for you in my interaction with Susan.

 

[wickedpen]

Amy was shocked by her mistake. "How could I have been so stupid? I know he is in charge. I know i need to beg for anything I get." she hissed to herself alone in the room. She wondered how she could make it up to him. She stood and went to the drawer, his drawer and withdrew a leather belt. She pulled on it feeling it to be hard, strong and dangerous. She put the belt in her teeth and got on her hands and knees and crawled across the hall to her room. She crawled with her head down then sat on her folded legs under her holding her hands up like a dog begging.

 

[BeachBum25]

Michael saw his mother entering HIS room with his belt in her mouth. He watched as she crawled to him with her head down; submitting to him totally. He got out of the bed and walked around her... looking down at her sitting on her feet.

He took the belt out of her mouth. “Kneel up straight slut.” He held the belt in his right hand; folded in half. Once she obeyed and was kneeling up straight, he allowed the belt to touch her shoulder. Michael the dragged the leather belt over her skin.... moving around her slowly. It dragged across her tits. Then he circled her breasts with it.

Smiling down at her, he moved around her with the belt. Arriving back in front of her, Michael let the belt drop between her legs. Then, he moved slowly around her again before smacking her ass with it. It wasn’t a hard smack, but it was certainly hard enough to get her attention. Then, he smacked the other cheek with it.

Standing behind his mother, Michael put the belt through the buckle, and then around his mother’s neck. Using the belt like a leash, he led her to the bed and guided her up onto it. Standing behind her, he caresses her ass before teasing her tight asshole with hers fingertips. “Anyone ever been in there?”

 

[wickedpen]

Amy's heart raced, not our of fear one my expect but this was excitement, erotic excitement of a forbidden game with a forbidden player. The leather on her skin was like electric and his calm reserve only intensified the tension. Teasing her breast with the belt was merciless but the slap on her ass was practically orgasmic.

Strangely being collared and leashed was reminiscent of the time she convinced her husband tying her to the bed, when they were young. He only did it once and had not enjoyed it. She had fantasized of it ever since. And now Michael was well beyond her fantasy.

She jumped up onto the bed as he had directed her with a pull of the leash. The strange primal nature of being leashed and treated like the bitch she was almost more than she could handle. Then he glided his hand over the welt on her soft ass before tracing down her crack to her forbidden entrance.

She shook her head bowing her head submissively, knowing this was his price and her desire.

 

[BeachBum25]

Michael teases his mother’s asshole with the tip of his finger. She did not directly respond to his inquiry, but he sensed that her answer was no. After pulling her into a sense of security, he took his hand and smacked her ass hard. The first smack was followed immediately by another smack on the other cheek.

He went back to teasing her tight rosebud; slowly circling it and brushing across it. Then he moved his fingers to her pussy. She was dripping wet. He ran his fingers through her folds.... slowly...... teasingly. His fingers were soaked when he moved them back to her ass and slowly inserted one into her tight ass... slowly pushing deeper.

“Your ass is tight, slut. Do you need it stretched? Do you think you could take my big cock in your slutty ass?” He then withdrew his finger from her ass. “Not tonight though. Crawl back to your new room. Perhaps tomorrow you will be worthy.”

 

[wickedpen]

OH the perversity of this man, my son, touching my most taboo spot. Asking me if I had ever had a man there. Oh gosh the thought makes me shudder with fear then swoon with interest. His slap on my ass stings tempering my soft desire. Then his finger slides along my aching lips. I know what he is doing and I want to feel him in there. I am on fire for anything he asks. "I am his bitch" I think sending an obscene wave of pleasure I have never known through me.

"... back to your room" he commands as I feel broken. So much did I want him to take me and make me do things I could never speak of. I looked at him for a moment but knew better than to object. I crawled off the bed and across the floor. I looked back dragging the leash and said "no, no one has ever done anything to me there." then crawled into his bed, I mean mine, and laid like a dog on my side still wearing the leash.

 

[BeachBum25]

Michael smiles to himself as his mother crawled away from him. Yes, he certainly had her. She would do whatever he wanted and she would do it willingly. He was certainly going to enjoy coming home to her.

He slept soundly that night. Emma had certainly worn him out. He was up early the next morning and decided to go for a run. He wanted to make sure that he was able to keep his stamina up and stay in shape.

After his run, he returned home and immediately went to get a shower. Once finished, he dressed and went down to the kitchen. His mother was there, still wearing the collar and leash. He smiled at her. “I am glad to see you are complying. You will be rewarded for your compliance, pet.”

He picked up an apple and headed for the door. “I have a 10 o’clock appointment. We will discuss your reward when I get home. Don’t do anything to fuck it up.” He headed out the door and went to Emma’s house to check on her appointment with Heather.

 

[wickedpen]

Heather was in a bad spot. She owed more than she had and the market had been soft. Emma was a big fish and Heather needed the sale. She was calculating how low she thought she could talk her client into going. She was calculating how much she was willing to give of herself to make this sale. Her manager told her is she did not make a sale it was going to be her ass. And she also knew that meant endless blow jobs or unemployment.

She pulled up to Emma's place in her four year old Lexus she had bought when she was rolling in cash but now could not afford to change the oil. She needed it to appear successful and attract clients. Same for her clothes. She got out in a black pencil skirt to her knee and a yellow blouse tailored to promote her perfect assets, her 34C tits. Her hair was long and blonde and eyes sparkled blue. She was hot as the Florida sun but broke could be.

She rang the bell and put on her "let's slose a sale" smile for Emma.

 

[BeachBum25]

As Michael approached Emma's house, he saw Heather walking to the door. "Fuck, she looks good." He allowed her to go inside, and he waited a few minutes before going to Emma's door; his mind on Heather's hot body.

Ringing the doorbell, Michael stood confidently in front of the door as he awaited Emma coming to get him. Although Emma had set this "appointment" up, Michael wasn't sure what her plan was. Yes, since she was so wealthy, she had influence over Heather, but Heather was married and getting her naked wasn't going to be an easy task.... or was it?

When Emma opened the door, Michael smiled at her and stepped forward to kiss her on the cheek. "Good morning Emma. It is really great to see you. I apologize for being a couple of minutes late." He stepped into the foyer of her home and looked around for Heather.

 

[wickedpen]

"Michael" Emma said pleased to see him and accepted his kiss and ran her hand over his back. "Come in Heather, I told you about her, my real estate guru" Emma said laying it on thick as she slid her arm into Michael's. Heather stood in Emma's living room and smiled as the pair entered and Emma introduced her.

Heather smiled and her body language and dilated pupils gave away an immediate attraction to Michael. Heather extended her long slender arm and said "Hello, nice to meet you. You are Amy's son? Sorry, it's kinda my job to know who is who around here." she beamed at Michael.

"Don;t forget about me you two" Emma said noting the clear attraction between the two. "So Heather, I am thinking of getting a second unit as an investment. I mean you know what I have done with this place and I have some friends," Emma started. Heather cut her off. "What you have done with this place? It is beautifully decorated but have you expanded?" she asked fearing the by-laws would cause problems that would screw up this deal.

"Maybe it's best if i show you" Emma said smiling at the young woman. Emma then turned and walked to the door that led downstairs.

 

[BeachBum25]

Michael allowed his eyes to wander over Heather as Emma introduced them. The outfit she wore accentuated every one of her amazing curves. There was no doubt he would enjoy that amazing body.

“Yes, I am Amy’s son and I was recently introduced to Emma, who is a very good friend of my mother’s. Emma and I really hit it off and I thought I would stop by to say hello. She insisted that i meet with you in case there was some business would could transact in the future.”

He looked down at the rock on her left hand. “Wow, that is a nice ring. Your husband is very lucky, and by the size of that diamond it would seem that he wants to keep you very happy.” He smiled at her and then turned to Emma who began to discuss business with Heather.

When they moved toward the stairs to the basement, Michael followed. His eyes immediately went to Heather’s hot ass. Moving with them, he let the ladies go down the stairs first, and then proceeded down behind them.

 

[wickedpen]

Heather was surprised by the basement. "This is unusual, I did not know this was possible?" she said as they walked into the pool area.

"Oh it is possible" Emma said "and if you ever feel like a swim or a soak in the hot tub just let me know."

Heather looked a little confused as Emma seemed to be giving a house tour, not putting money in Heather's needy hand.

"So, Emma you said something about another unit?" Heather said.

Emma smiled, "How much do you make off a 'unit'?" she said emphasizing unit with air quotes.

Heather grew nervous as Michael was smiling at her.

"I don't know maybe five thousand, why?" she asked.

"If I were to give you five thousand dollars how would you entertain my friend Michael here?" Emma said with a smile and a glance at Michael.

Heather swallowed her pride in a second and then looked at Michael. She paused and knew she would only take home twenty five hundred from the sale and this was pretty much a cash deal. She could pay off everything and then some, her mind raced and her nipples grew. She fingered the wedding ring. She was not a naive little girl.

"What do you have in mind?" she asked softly.