Decision of the Shy Woman

Chapter 1

For over 15 years 57 year old Margret Carter has been divorced bringing up her 2 daughters by herself with very little financial support. She worked two jobs to make sure both her girls got a good education. They are doing well, but Margret still has their college note to pay off even though they got half their tuitions paid for through scholarships.

Margret is very shy only having a few dates over the last 15 years she was too busy providing for her children. They each had jobs, but that was just enough so that they could get what they needed above and beyond what their mother could pay for. Margret is not model pretty but keeping herself in shape and doing the best she could with what the lord gave her she presented a nice picture even though the clothes she wore made her look dowdy.

Carl Archer a ruggedly handsome self-made millionaire with two sons, divorced for two year and 49 years old, came into town looking at a few buildings that were on the market he makes old mill properties into condo’s and then sells them. He had a few buildings in the area he was interested in and contacted a lawyer in town who Margret worked for as a legal aid. The first time he laid eyes on the older woman he was infatuated with her shy demeanor and timid personality.

The lawyer did the work that was needed by Carl over the next couple of months they became friends and Margret during that time opened up enough for Carl to get the background he wanted to know about her. He asked her out to dinner on the pretense of saying thank you for the great work she did for him, but during the dinner both knew that there was something more there.

Every time Carl came into town he made sure he had at least one date with Margret. Over a few months they got to know each other better and Margret invited him to her apartment. Carl felt bad for Margret seeing where she lived although her apartment was spotless the neighborhood was rundown and he did not want to see her living there. Having bought a building in uptown that he was renovating he asked Margret if she would like to live in a new condo uptown. She said that she could not afford the rent; and so on the pretext of needing a onsite manager for the new condos Carl told her she could live rent free as payment for managing the complex.
Carl brought her over to see the condo it was over two thousand square feet and in one of the best parts of town. She even had off street parking under cover. It was a no brainer for her she said yes and moved in the first of the following month. The condo was empty when she saw it. Carl asked her in her opinion what type of interiors were needed colors furnishings and such. Carl had it furnished for her, so she did not even have to bring any furniture with her so she sold everything to her former landlord.

All this has happened over an 8 month period and Margret was becoming bewitched by Carl and he could see it. Carl was spending more time in the area he even set up a condo in this building for himself asking Margret to furnish it and giving her a credit card to do it with. They were the first two occupants of the build as it was still being renovated at the time they moved in.

Everywhere Carl went even out with Margret he always had a camera with him. He took many pictures of Margret everywhere they went. At first she was very intimidated by the camera, but Carl told her that she was a beautiful woman to him and loved to take her picture. It was now over a year that Carl met Margret and she was paying all her bills down and having a great time with Carl, her boss was very good to her also knowing that Carl was one of their bigger clients was sweet on her. On her part Margret did not know how rich Carl was and she never cared to find out. Carl knew this and was glad that she was not after his money.

One night Margret invited Carl to have dinner at her condo when she got a phone call about the student loan for one of the girls. They told her that if she did not make a balloon payment the interest would jump for the loan by 10 percent. Margret was very upset almost in tears at first she did not want to tell Carl her problem, but finally she told him that she would have to come up with 50 thousand dollars by the end of the month or one of the student loan interest would go up. Carl told her it will all work out and then the subject was dropped. They sat in the family room watching TV Carl wrapped his arm around Margret she felt so secure in his arms.

At work the following day Margret got a call from Carl he was supposed to be leaving and going to another one of his properties, but he put off the trip until the following day and he wanted to see Margret tonight if she was available. Laughingly she said she had to check her calendar telling him yes she could fit him in, but laughed and he hung up laughing also.

Mr. Herman got a call from Carl to draw up some paperwork for him to give a grant to Margret in the sum that she owed for the student loans he gave Margret the paperwork with instructions to find Carl and give him the paperwork. Mr. Herman had her leave early to bring the paperwork to Carl. She got home and called Carl on his cell to see if he needed the paperwork right away. He said no, so she told him to come to her condo and she will have supper ready for them.

As soon as she got off the phone with Carl Margret started supper cutting up the vegetables, boiling potatoes, making a pie, making a salad and marinating a steak she picked up on the way home. When the meal preparations were complete she went into her bedroom and removed the clothes from her closet that she decided to wear and put them on the bed.

She went into her bathroom took a long hot shower, then dressed in a red party dress forgoing the pantie hose that she usually wore with dresses, she opted for a matching bra and panty set. The dress was something that she bought a while ago and did not feel comfortable wearing out in public as she felt it was too revealing for her to be seen in public with it on. Margret figured that only Carl will see it and then she could find out what he thought about the outfit as she was down on herself she feels her breast are too small and she is getting secretaries spread from sitting too much even though the Attorney she works for has a gym pass for all their employees that Margret makes use of religiously.

It was a little after five PM that Carl knocked on Margret’s door. She opened it and Carl was amazed at how gorgeous she looked and complimented her profusely to the point of her being flushed. There were a few people gathered around in the hall to see what that handsome man was talking about as not many people have taken notice of Margret, but tonight they saw a striking woman standing at the door and it took all there a moment to realize that it was Margret.

Margret grabbed Carl by the arm and pulled him into the hall of her apartment as he was embarrassing her with all the people standing outside her door listening to his accolades of her person. He did not know what the matter was and why she was so embarrassed. She told him and he said that he will personally help her develop self-image that emits a sense that she is a wonderful person and she is beautiful no matter what she is wearing.

Carl went out onto the deck and cooked that steak as Margret finished the preparation in the kitchen they had everything timed just right. Both sat down and enjoyed a wonderful meal. After cleaning up Margret remembered the paperwork she brought home for him, she went to her attaché case, retrieved the envelope and handed it to him. Carl in turn reached into his coat pocket and gave her an envelope. She opened it and there was a check for the student loan payoff he also gave her a letter that was in the envelope she gave him that stated the money was a grant from Stillwater group, so her note was all paid off.

It took her a few minutes to grasp what had just transpired and then she ran too him and jumped up wrapped her legs around him and hugged him. They kissed and he walked with her in his arms to the couch where they continued kissing while Carl slowly removed her clothing and was amazed at her beauty as for the first time he gazed at her lovely unclothed form. Margret did not stop Carl and she did not feel self-conscious that she was nude and he was still dressed as it felt right to her.

Carl picked up Margret and brought her to the bedroom where he stripped off in front of her on her part she took notice of the mighty weapon rising between his legs as he climbed into the bed with her and visually and manually explored her body. Working his way down to her breast telling her all the while how beautiful she is and running his fingers through her dark pubic hair and bringing his face down to her vaginal area inhaling her scent telling her how wonderful she smells. She spread her legs as he started to massage’ her very moist pussy. He slid himself between her legs and started to kiss the interior of her thighs working his way to her pussy licking and kissing her most intimate area while praising her form. Using his mouth and his fingers he brought her off within two minutes of started to lick her pussy. She was screaming her fulfillment at the top of her lungs. Carl laughed to himself we will see about the soundproofing in this building tonight he thought.

Giving Margret a few minutes to recuperate after which he started to kiss his way back up her body stopping at her breast and neck finally French kissing her. She could feel his cock at the entrance to her pussy. Wanting him inside her she reached down and inserted his member into her intimate passage with one thrust he was all the way into her flooded honey pot. They kissed with their bodies intimately connected and Margret for the first time tasted her pussy on his lips and this made her hotter. She was meeting all his thrusts and working toward another orgasm. The dance of love became more animated as they were trying to reach orgasm at the same time. Carl slammed into Margret balls deep and this caused her to start the most wonderful orgasm that she has ever felt and Carl was right there dumping his load of baby makers to add to her joy.

Carl rolled off Margret exhausted looking over at his love mate she was in her own bliss with a dreamy smile on her face both were soaking wet from their activity and Margret felt like there was a river flowing out of her well used vagina. After a few minutes Margret slid down to Carl’s mid-section and started licking his flaccid member something that she ordinarily would not do. She could taste their combined lust and it was not as distasteful as she remembered in fact it was turning her on cleaning her lovers’ member. Carl looking down at his lovers mouth taking his member in and licking all around it thinking that he may have found his soul mate but he would have to sit with her to discuss a future together as she is too nice a lady to make her do something that she feels is distasteful to her being.

Completing her task of making love to her lovers’ member and bringing it to full staff again she laid back hoping that he would use it on her again, but to her surprise he slid down to her mound and started to lick the dew off her vaginal lips on her part she opened her legs wide to give him access to her over heated sex. He lapped up all the deposits and brought her off another time and then laying back coaching her to embed her sex on his member after she came down from her orgasm.

Margret knelt over her lover and using one hand to aim his member she sat on it imbedding her pussy to the max. She was slowly riding up and down on his member with her eyes closed enjoying the full feeling she was getting from his cock something that has been missing in her life for a long time. All too soon she was racing to her climax as Carl shot his wad into her pussy. She was getting sore and he was raw from all the rubbing of their intimate areas. Rolling off him she was glad that she was beyond getting impregnated as her periods stopped many years ago.

Both fell asleep with Carl waking up and he started dressing. Feeling the movement on the bed Margret woke up also asking him where he was going. He said to his condo looking at him with tears in her eyes she asked him if he would stay the night as she would feel lonely without him. Smiling at her he got into bed spooning her with his arms around her and when they woke up in the morning they were still in the same position. Looking at the clock it was 9 AM an hour later than her start of work she was in a panic she has never been late to work in her life. Carl said don’t worry about it and picked up the phone getting in touch with Mr. Harman he told Mr. Harman that Margret was doing some errands for him and will be busy for the day. Then Carl told him to bill her time to his account.
They both took a shower together good thing that he had the foresight of having large showers put in this building and they had sex in the shower before they got out. Carl started to put on the clothes he had last night and Margret started to get dressed, but Carl stopped her saying I would really like you to stay nude if you would. She could not say no to him after what he has done for her and the wonderful time she had last night smiling she said OK master.

The last words were music to his ears Carl at this moment is surer than ever that he has found his soul mate than he was yesterday, but he will keep pushing the envelope to see how far this beautiful older lady will go to please him. He said that he was going to his condo to change she asked if she could go with him he said sure she started to get dressed, but he stopped her again giving her his dress shirt from yesterday saying this should cover you enough to get to my place. Can I at least put on some panties she asked? Not saying no, but he told her to put on the shirt see how much that covers then we will see. She put the shirt on it went to her knees as she is only about 5’3 and he is 6’5” so as long as she does not bend down nothing will show, but the sides of the shirt come up almost to her waist and anyone seeing a side view will realize that she is nude under the shirt. The shirt was light color and her nipples could be seen through the shirt in the right light along with her dark pubic hair. All in all Margret was basically nude going down the hall to the elevator lobby to wait for the elevator so they could go to the penthouse suite that Carl had. Good thing there were only construction workers in the building or is it she thought.

Getting into Carl’s condo she went to sit on the couch to wait for Carl to get dressed when he turned to her telling her to take off the shirt as he will be putting it with the clothes to be washed. She did as he asked without any though of her nudity and went to sit down and watch TV while she waited for him. He was dressed in a few minutes but he told her that he had to make a few phone calls.
It took him an hour and then he came over to sit with Margret. Looking at her Carl asked Margret how she felt being nude in front of him. Blushing as for the first time she realized that she was nude, but it felt so normal in front of Carl and that is exactly what she told him. He said great that is what I wanted to hear.

Carl then looked at Margret with a very serious look on his face Margret could tell that he was formulating his next thought so that it will come out as he wanted it to. He looked at Margret and said that he thinks that they are soul mates and he is falling in love with her, but he has a few kinks that he does not know if she will be happy with what he is going to say. She looked at him saying you’re not a serial killer are you? No I do not even like cereal he told her. They both laughed and then Margret said to Carl that we could probably work around everything else then as you have been the most generous person I have ever met and I have been falling in love with you also.
Margret was sitting on the couch and Carl was sitting across from her. When she first sat down she had her knees tight together but during their conversation she shifted position so now her vaginal area is completely exposed to Carl’s view. Margret could see that Carl was losing his train of thought and followed his gaze to her pussy. She laughed and asked him if her pussy got his tongue. This brought a belly laugh from Carl.

Getting back to his train of thought he told Margret that he is looking for a wife that is not afraid of being nude in front of people and someone that he can take pictures of nude not matter where they are. A woman that will remove her clothes at his request and dress as he requests I will be away for a week or so please think about this and if you think you can do this we can go forward, but if not that is alright I will still be your friend and love you as I do. All that has been given you is yours and anything else you need will be given, because I adore you.

Margret’s face is ashen she looks like she has seen a ghost; her perfect man wants to show her off. Will she be able to do it? She is sitting in his condo nude and she could feel her pussy moistening again and her nipples get hard. Will she be able to eliminate the stigma that her parents instilled on her about her body how it is dirty to show it? She brought all these thoughts to Carl and he said so far you have had the best time of your life this last 24 hours than you have had in the last 50 years and lightning did not strike you dead when you left your condo nearly nude. Margret said that Carl was right. Carl continued that you’re showing me your pussy now and nothing has happened beside you exciting me and you becoming excited. Again she said he was right, but I don’t think I can be nude in front of other people. I don’t mind being nude in front of you though. Carl said did you think that you could be nude in front of me yesterday morning? Did you have any idea that you would be sitting here comfortably nude with your legs spread discussing your exposure. No on both counts Margret said.

Carl finished with I do not want an answer now, but think about it and remember we are shooting for you to be comfortable to strip when I ask you to, but it will be done in phases as you have done so far. Margret told him she will at least think about it and with that Carl looked at his watch telling her that he has to catch a plane in 3 hours so they would have to go.

He handed her his suit coat and told her to put it on, but leave the buttons undone if someone is in the hall or elevator hold it closed with your hands otherwise leave it open he instructed Margret. She turned red with embarrassment but did what he asked. They did not meet anyone in the hall and when they entered her condo he asked her if she wanted to ride with him to the airport and then the limo would bring her back to the condo. Not wanting to have the time with him end she said sure.

Walking into the bedroom Carl retrieved the discarded red dress from last night and gave it to her saying this should be acceptable to wear to the airport. She started to get the bra and panties but Carl stopped her. The dress had large buttons on the front and it was long in the back and came up to within 3 inches of her pussy in the front when she sat down her pussy would be showing, but she figured it was a test so she put on the dress and makeup then off they went to the airport a 30 minute drive.

When the limo came to pick up Margret and Carl the driver jumped out and opened the door for both Carl had Margret get in first and no matter how hard she tried she could not keep her modesty in this dress her boobs showed when she bent forward and her pussy showed when she sat to get into the limo. On top of that as soon as they started off to the airport Carl was unbuttoning her dress and sitting next to Carl on the hump with her legs straddling it spread her pussy for the driver to see. She could feel Carl run his hand under her dress and start to rub her well used pussy. It was only a few minutes and Margret gave into the pleasure that Carl was giving her and disregarded the fact that she had no modesty left intact.

At the airport Margret got out of the limo her dress was almost all unbuttoned and she did not care she was sad that Carl was leaving and gave him a big wet French kiss in front of the departure building on his part he rubbed her pussy as they were kissing. Unknown to her she was almost totally exposed as she watched Carl disappear into the terminal. She got back into the limo not bothering to button up. The driver was looking at her exposed parts all the way back to the Condo, but they did have a lively conversation also on the way back and he was a perfect gentleman as he opened that door for her even though her breast and pussy were showing as she exited the car.

Chapter 2

The following 10 days Margret talked with Carl every day but nothing was mentioned about their discussion before he left and if Margret brought it up he said that they will discuss it when he gets back. The good thing about working it kept her mind off her loneliness and when her boss asked if she wanted to work over time she did. The time went very slow for her she really missed Carl.
Sitting home at night she was trying to imagine what it would be like being nude with everyone else dressed. Whenever she was home she stripped nude to get used to being nude. During the weekend she would go out onto her deck nude and sunbath it was semi private and the building facing her condo was not occupied yet, but there were workmen there during the week, so she was careful when she went out there when she got home from work.

The weekend before Carl came home unbeknown to Margret there was a crew of tapers working in the apartment that overlooks her deck she got out there about 11 AM and was sitting there with her legs comfortably parted reading from her kindle when she saw something in one of the upper windows she looked again and it was noon time there were about 9 men looking at her. She put the kindle down in her lap to protect what modesty she had left and waved to the men. They opened the windows and waved back they stared to get rowdy, so Margret went into her condo and sat on the couch facing them they could still see her but she could not hear what they were saying. Then it dawned on her that she was sitting out on the deck and the guys could see her, but for the rude remarks she would have stayed out there if they were polite. Margret realized that her answer to Carl will be yes she will do as he asks her she loves Carl more than her modesty.

Monday morning Mr. Hermon called Margret into his office with a large amount of papers that had to be sorted and many pages that had to be typed. He told her that it was for Carl as he is contemplating purchasing another property that he saw at the other end of the state. He would like it done by Wednesday afternoon when he gets back into town he would like you to bring it with you when you meet him.

Margret worked very late Monday and Tuesday night, Wednesday Margret was finishing up the work at noontime, everything was sent to the printer when Margret got a call from Carl saying that he was ahead of schedule and will be at the airport by 1:30. Mr. Harmon told Margret that she could use that shower that was in his office if she liked as the limo will be at the office at 1 PM. To pick her up

At twelve thirty a courier came to the office with a box for Margret she went to her desk and opened it. There was this beautiful dress in there blue like her eyes and made of silk. The note said do you like it? If so wear it only. She brought the dress, her makeup to the shower room and started to take a shower noting that she had to hurry to get ready in a half an hour. Getting out of the shower she realized that there were no towels in the rack she knew there were extra towels in the closet outside the shower room door.
She had no choice but to go out and get one hoping that Mr. Hermon is not in his office. Opening the door and peeking out Margret did not see anyone, so she darted for the closet and in walks Mr. Hermon getting a shot of her firm little buns. Saying oh the hell with it she got the towel from the closet thanked Mr. Hermon for letting her use his shower while drying off in front of him. He was stunned to see this lovely younger lady in all her glory he knew he should turn away but could not.

She finished drying off in the shower room but left the door open and dried her hair then put on her makeup. Margret walked out into Mr. Hermon’s office and asked him to zip up her dress for her. Standing there back lit Mr. Hermon could see that the only item of apparel she had on was the dress that disappeared when she was back lit. The dress had sleeves but the front of the dress plunged almost to her waist and the sleeves threatened to go down to her hands, thus exposing her breasts, but the back was relatively speaking much higher it went to the middle of her back. The bottom was like her red dress, so when she sat down her pussy would show and when she bent down her breast would be exposed.

At precisely 1:25 PM Margret was walking to the limo parked in front of the lawyer’s office with her attaché case and all the paperwork she produced the last 3 days she was antsy as she missed Carl so much. The drive seemed to take forever and the wait at the luggage pickup before she saw Carl was a century. Finally she looked up on the escalator and she saw her handsome young man coming down the stairs, his camera dangling from his neck. She ran over to him jumped up and hung onto him kissing him just as he disembarked the moving stairs. Margret’s pulled back and said yes, yes, yes I will do it and then kissed him again.

The chauffeur was standing next to them and Carl handed his carryon bag to the chauffeur, while he half carried Margret to get his luggage off the turntable. The Chauffeur took the luggage and Carl walked out the door of the arrival building with his arm around Margret. He walked by a bench then stopped looking at Margret he said that he would like a picture of her on the bench she sat down and he took a few pictures then he told her to put one leg up on the bench with her foot on the edge and the other on the ground then drop the upper leg to the side. She did it without blinking and her pussy was on display for the Carl the Chauffeur and everyone else that walked by. Carl was ecstatic that Margret did as he asked.

They got to the car with the chauffeur holding the door Margret slid in showing all her intimate charms to the two men. She could feel her vagina drooling as the men looked at her most intimate areas and her nipples were so hard they hurt even rubbing against the satin. Margret took her time getting in to prolong her exposure. After everyone was in and they were on their way back to the condo Carl was kissing Margret and trying to get to the zipper in the back of the dress. She stopped kissing him and turned so that he could undo the zipper she let the garment fall to her lap and they continued kissing while Carl massaged her breast. He was soon trying to get to her pussy so she got up off the seat so that he could finish undressing his lovely older woman. Taking the dress she put it to the side noticing the large wet spot on the back of it as she spread her legs wide for Carl to gain access to her molten pleasure palace she could see their driver watching the action in the rear view mirror.

They are almost at the condo complex when Carl had 4 fingers buried in Margret’s very wet pussy and she is on the verge of cumming as they pull up to their stop. Carl tells the driver to go around the block again and she came like a freight train spewing her juices throughout the back seat and there was the sweet smell of the female orgasm permeating throughout the limo. Carl gave Margret his suit coat she put it on, but leaving it unbuttoned she threw her dress over her shoulder and headed into the condo complex. The limo driver followed with the entire load of luggage they all went to Carl’s apartment.

Carl opened the door and Margret was the first one in she put her dress over the couch and took off his suit jacket thus rendering her form completely nude for the two men’s viewing pleasure. The chauffeur was helping Carl bring in his bags while Margret was sitting with her legs positioned as in the photo that Carl took at the airport leaving her engorged pussy lips visible to the men. Carl tried to give the driver a tip but he said that the sight of the mature ladies pussy was tip enough for him.

The driver said good bye and shut the door this is when Margret jumped up and unbuttoned Carl’s pants then pulled down both pants and underwear at once she was on his pecker like a hobo on a ham sandwich giving him a blow job. They spent the whole night at Carl’s Condo and in the morning Carl asked Margret if she would like to come to work for him at 3 times the salary.
He did not even get all the question out of his mouth when she said yes. First thing in the morning Carl called Margret’s boss telling him that he will have to get a replacement for Margret and Carl said that he would pay for the replacements training.

ajtoeknee[at] All rights reserved 2014-2020
– Shared with you at

2 thoughts on “Decision of the Shy Woman

  1. Doris, WoW! What a great story… I love to see Margret in person for real. I also feel there is so much beauty in a more mature woman. I love the story lines.


    1. Hey Dwight,
      I liked the story too, very much. I’m also sure that there are more Margrets out there for real observation. If you have a little story about one, don’t hesitate to write it down – I’ll be happy to publish it.

      We can ask AJ (the author of this story) if his fictional character Margret has left some real photos to share. What you say, AJ?

      Hugs and kisses to you,


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