A Milf at the Country Club

This is a story about a woman who thinks her life, and sex life is slipping away. Unaware that she is in the prime of both, she reaches out to what she perceives as the only options available to her. To make this point clear, I tell you that women in their late 30's and 40's are at their most sexy and sexually appealing. This is a story about a woman who discovers pain heightens her experiences, and she likes it.

Part Thirty

Master takes in a temp while his main whores rest

Diane showed up for work in a business suit with a very short skirt, and a kick pleat in the rear, with a long raccoon tail plug which showed perfectly, and master was enjoying watching her walk around the office. Kathy was waiting in Diane's office waiting to be needed by master, sitting there wearing only heels. Master took care of some business that needed his attention, then called for Diane to bring Kathy to his office.

Diane: "Mr. Raymond, here is Kathy as you requested. Would you like me to stay or return to my office?"

Mr. Raymond: "Please stay in case I need your assistance. Kathy, do you know why you're here this morning?"

Kathy: "Yes Sir, I am here to take Kimberly's place."

Master sat up a little bit taller in his chair and had an annoyed look in his face when Diane slapped Kathy in the face with all her might. Kathy not being ready for that fell to the ground from the force of her strike.

Diane: "You don't get to take anybody's place you ambitious little slut. You are here for master to use while Kimberly is doing other things. What makes you think you are anywhere near good enough to replace Kimberly? And when did you stop addressing her as Miss Kimberly?"

Kathy: "Ma'am, I am sorry, I chose the wrong words, I didn't mean to insinuate that I was replacing Miss Kimberly in her position, and I apologize for not addressing her properly Miss Diane."

Mr. Raymond: "You've had some problems staying between the lines set forth for you lately slut. Is there a problem with your hearing or your ability to learn?"

Kathy: "No sir, Again I am sorry and I will do better sir. I only want to serve where I can."

Mr. Raymond: "Turn around and bend over with your legs spread wide."

Kathy did as she was told keeping an eye on Diane for her approval, or her disgust should she anger her again. Master looked between her legs and looked at Diane, and she knew exactly what he was thinking without saying a word, so she spoke first.

Diane: "I can take care of that right now sir. Would you like the honors or should take her and solve that problem in my office?"

Mr. Raymond: "Go get what you need and come back to take care of it here in front of me."

Diane left the office and returned about three minutes later with a tail plug with a bunny tail like the playboy girls had on the rear of their uniforms.

Diane: "Sir, all I have here is a size large with a rabbit tail and some lube. Would you prefer I go to the house and get other sizes and styles?"

Mr. Raymond: "Considering the events of the morning so far, I think the large bunny tail is in order. Kathy, did you not recognize that Diane and Kimberly both wear plugs with tails?"

Kathy: "Yes sir I did."

Mr. Raymond: "Then why did you show up without a plug and tail?"

Kathy: "Well sir, I'm not that anally experienced, and I've never worn a plug as part of my uniform."

Diane: "Well then, we're going to fix that right now. Stay bent over and don't tense up."

Diane lubed the plug and Kathy's asshole and proceeded to push and twist the plug, but it didn't go in easily. She looked up at master and again heard what he was saying without him speaking, so she gave it one huge shove and it popped into place. Kathy screamed out and Diane immediately slapped her hard on the ass, leaving a faint red hand print.

Diane: "Did anyone tell you to make noise you disgraceful slut?"

Kathy just shook her head and stayed in position waiting for someone to tell her to move. Master came from around his desk to examine the plug, pulling and twisting it causing Kathy discomfort, but she didn't make a sound. He looked at Diane and then went back to his desk, the entire time thinking Diane had the talents and abilities to train new sluts for him. What a person to have if you need them, he thought.

Mr. Raymond: "Yes Diane, it is quite tight, but it will loosen up before the end of the day. Now if you would be so kind, take this slut over to the corner and teach her the submissive position and have her remain that way until I want her."

Diane put her in her knees in the corner, ankles together, knees spread wide, her ass cheeks on her heels, her arms in the small of her back, and her gaze focused downward. Diane left the room for a moment and returned with a small crop whip and laid it on master's desk. Again, no words were needed but they spoke bushels with their actions and looks.

Mr. Raymond: "Say Thank You to Miss Diane slut."

Kathy: "Thank you Miss Diane for teaching me and installing my plug and tail."

Diane: "Very good slut, just don't screw up again here today, you make me look bad in front of master and I won't tolerate that."

Kathy just nodded and put her eyes back towards the carpet as instructed. Diane smirked at master before she left his office for her own, and master started to think about the past few weeks. How lucky could one Dominant man be to have two devoted sluts and whores at the very same time? He thought himself very special, and he wanted to test Diane's training capabilities as the one kneeling in his office was going to need a strong hand to get her straight. And it had been years since he had a slut with the talents to train the younger sluts, she was like a gift from heaven. He wanted to watch these two interact more and maybe expand Diane's duties in his house.

Mr. Raymond: "How did you come to work in my house slut?"

Kathy: "I was hired by Mr. Bernard, and although I didn't say I wasn't anally trained I did tell him I was eager to learn anything master had to teach me."

Mr. Raymond: "To be a slut in my house, you must offer up three holes at anytime you are requested. Is that clear to you?"

Kathy: "I will endure whatever training and activities master decides he wants from me, I just want the chance to please and serve."

Mr. Raymond: "Then we will work out a training schedule for you between myself and my right-hand slut assistant Marcus. Miss Diane will be taking over your day-to-day training, but the sexual training will be done by me and Marcus. It appears Miss Diane is not a favorite of yours or her of yours, is there any other reason I should know about as to why?"

Kathy: "I made some mistakes with miss Kimberly and here with you, and she thinks it reflects badly in her when I do things like that."

Mr. Raymond: "It does make her look bad, but not for the reasons you think. She recommended you to Mr. Bernard and you were hired from that recommendation. Just now, she acted out of concern that you were not being respectful to Miss Kimberly and myself, and apparently, she doesn't like that either. Just do as your told and don't attempt to overstep and you'll be fine."

Kathy: "You knew the circumstances of my hiring and yet you asked me about it sir?"

Mr. Raymond: "Listen up slut, there is nothing I don't know ahead of or at the time it occurs, and you would be well advised to keep that in mind."

Kathy: "Yes sir, I will sir."

Mr. Raymond: "Now I have work to get done. Climb under my desk and suck my cock while tend to my business."

Kathy did as she was instructed but never assumed her day would be spent under a desk, she had imagined she would be fucked then put in a corner until the next time he wanted her, but this was not going to be like anything she had experienced before. So, she steeled herself and self-committed to give the best oral experience to him that she was able to. She did a good job sucking without getting sloppy and using her tongue under the head of his cock, but she couldn't believe the control this man had. She had been sucking for at least forty minutes and he hasn't shown any signs of being ready to cum yet. It seemed her jaw was going to get training today as well as other parts of her, and she was doing her absolute best to impress master with her oral talents and commitment to the job. When a gentleman came in the office she pulled off his cock in shock and remained absolutely still and quiet. Master pushed his chair back, slapped her across the face and yelled at her.

Mr. Raymond: "No one told you to stop slut, get back under there and get to work."

After resuming the man and master conversed in business circumstances, he called for Diane on his intercom to come in his office. She walked in and noticed Kathy not in her place and asked Master about her.

Diane: "Where did your slut go master?"

Mr. Raymond: "Under the desk doing trying to do simple slut things."

Diane: "What do you mean trying master?"

Mr. Raymond: "She needs to learn not to stop doing what she is told until she is told to stop."

Diane: "Would you like me to take her and give her some further instruction?"

Mr. Raymond: "No, I'll tend to her for now, then I will send her to you for an evaluation on her oral skills on a woman. But I do want to tell you that you're not responsible for her actions, or her missteps. She will sink or float by her own actions."

Diane: "I wouldn't mind taking her training into my own prevue if you wish?"

Mr. Raymond: "You want to take over her training?"

Diane: "Yes, I think I would accel at it sir."

Mr. Raymond: "Very well, I will set it up with Mr. Bernard and let you have free reign over her."

Diane: "Thank you sir, I want to assist you in any way I can sir."

Master was elated that Diane wanted to oversee her training and was a bit excited about how good of a little part time whore she could make out of this slut. Kathy was still industriously shucking his cock and he thought it time to give her a rest, so he let himself come but he reached down and pulled her head fully down into his cock lodging his cock in her throat. She choked, gagged, and bucked but he held her there until he fully emptied his ball down her throat. When he released her head she was panting and heaving for air, but she made sure she swallowed every drop he gave her.

Mr. Raymond: "Now go to Diane's office and wait for her to tell you what to do, and don't disappoint her, she is going to be in charge of your training."

Kathy nodded and left his office and he called Diane to let her know Kathy was coming, and that he would like to use her pussy before the end of the day. Diane reassured him that she would make Kathy available for his every need. Master was satisfied with Diane, no more than satisfied, he was overjoyed even though she had not yet met his sexual proclivities, she was willing and working towards it.