For the last 6 months Roselyn has been talking to a young man called Jon on the computer. She met him through an add on an Internet bulletin board in the people to people section. The message stating very simply "Looking for woman 50 and older that would like to make a lot of money in a short period of time." With an email that you could click on attached to the message where you could leave your email address and name if interested.
She read the Ad a dozen times, but when curiosity got the best of Roselyn she sent him a message and Jon sent back his email address explaining that he was 30 years old and has made enough money to last him the rest of his life which he made on an Internet business. He is looking for a woman or women that ar3 at least 50 years old. They have to be married and her husband has to accompany her on all her adventures.
While corresponding with her the only thing that Jon told Roselyn was that she would have to do whatever he asked her to do with her husband's approval. Once that she said no or her husband did not approve of the adventure that was the end of their relationship with Jon. He would pay her off what was owed them and that would be it. Jon was willing to pay any lady that he accepted the following: For one day 2,000 dollars, for a week 20,000 dollars for a month 100,000 Dollars, and for a year 4 million dollars. Roselyn did not say anything to her husband about this opportunity. Being very naive she did not have any idea what the implications were of this advertisement. Furthermore Roselyn did not know how her husband would react if she told him about Jon's Ad, as they married out of high school she had never dated anyone else and he had never dated anyone else, to her knowledge also. She was 15 years old and he was 17 years old when they met in school.
It was Friday afternoon at about 2 PM when Roselyn's husband Charlie came through the door over 2 hours early.
"What are you doing home so early? You missed me and could not stay away any longer" She asked her husband smiling at him.
"I just got laid off." He stated very grimly.
This revelation was just what she needed to make up her mind about applying to see if Jon would accept her. She was just 50. Roselyn is 5'9" tall with short black hair. 34b breast, 23" waist and 36" hips. Her completion belies her Italian heritage and her brown eyes sparkle when she is talking. Roselyn could melt you with her smile, but you have to watch out for her Italian temper. Her husband is over 6 feet tall and his makeup of many nationalities has diluted any strong characteristics of nationalities making him extremely laid back. This is a good match for Roselyn. They have gotten along famously together all these years.
After dinner Roselyn went into the den where her husband was watching TV and told him about Jon and that she wanted to apply to see if he would accept her. He asked her if she really wanted to do this. She told him that seeing that there will not be a paycheck any more and they would pay a lot of taxes if the dip into his retirement fund it is the only wise thing to do. He reluctantly agreed and she sent an Email to Jon stating that she and her husband were interested in meeting Jon.
Within and hour she got a reply. He asked for a picture of her, which she emailed to him as she had some pictures on disk. Ten minutes later she got an email asking where they lived. She told him that it was in a small town in the northeast. Jon said that he will meet them at their city Airport the next day at 11 am. Their airport was a small Northeastern airport with no commercial carriers. They were to go to the counter at the airport and introduce themselves and the airport manager will direct them to Jon's plane.
It was a very restless night for both Roselyn and her husband Charley. They did not know what Jon looked like or what he would ask her to do. She is a very proud and modest lady, who embarrasses easily, but they need the money at this time and with her limited marketable skills and both of them being over 50 years old each their employ ability is very limited in their area of the Northeast.
The next morning Roselyn got up at 8 am. She went through her closet and picked out a few outfits that she thought were appropriate for the meeting today. Her husband got up before her and was out side doing yard work, before it got too hot. Roselyn nervously went about her preparation for their coming meeting with Jon. Taking a shower she trimmed her pubic hair, making sure she got all the hair around her anus. Roselyn shaved her legs and under her arms. Roselyn got out of the shower drying her body thoroughly with a nice soft towel and looked in the full-length mirror in back of the door. She still had a good figure even after 3 kids she thought to herself as she was checking her vaginal area spreading herself open in front of the mirror. She turned red with embarrassment when she felt herself moisten and her nipples become erect. Roselyn did not know why she did all the grooming of her very personal areas today as she doesn't usually do this when she goes out. She has never opened herself up and checked her labia as she did today she thought to herself. If anyone asked her to display herself in this manner she would be humiliated. She would even be embarrassed if her husband asked her to open her most intimate parts to him.
Drying herself, she walked nude into their bedroom, with a towel around her damp hair, noting to herself that this is something she does not usually do either. Walking around the house nude is something foreign to her but she was excited. In front of her bedroom mirror she fixes her hair. It took her twice as long today as it usually did she wanted to look extra special today for her meeting with Jon.
Doing her make up she was still nude, when Charley walked into the bedroom. It was nearly 9:30 and he wanted to know if Roselyn would like him to cook breakfast for both them. He was pleasantly surprised to see she was naked. Charley loved to look at her naked body. He might be prejudice but to him she was the most beautiful woman in the world. Charley went up in back of Roselyn and started to massage her back at her shoulders and worked down her back to her butt and waist. She leaned back into him and he felt a stirring in his groin and also some doubts were cropping up in his mind. He had a good idea what Jon would want from his wife, will he be able to watch her humiliate herself in front of him and this stranger?
He stopped rubbing her back when she asked him. "Charley what outfit should I wear today."
Charley liked her to wear dresses, and skirts. The outfits she had laid out were not anything that he likes, so going to her closet he picked out a short denim skirt and an almost see through white button front blouse that he bought her a few years ago that she didn't like to wear because it was almost transparent in the right light. Going to her dresser he picked a matching bra and panty set of flesh colored almost see through material. Roselyn blushed when she saw the outfit that Charley picked out as she did not like to go out in public in outfits like that.
It was a warm summer day and she has a chance to make big money, but in the back of his mind he knew that before the day was up Roselyn would probably be naked in front of this stranger
After the breakfast dishes were cleaned up they got into their car for the drive to the airport. Roselyn told Charley that he could stop the proceedings anytime he did not like what was happening. Charley told her that she could stop the proceedings also if she was uncomfortable with what she was asked to do. They could find something else to do to make money maybe a home business thought Charley
They got to the airport at about 20 minutes to eleven. Going to the information desk they asked where Jon's plane was. The tower manager told them he was inbound and will be landing in about 10 minutes. They went to the windows facing the runway and watched as the largest jet they ever saw landing at their airport, it was a 737 that landed on the east west runway. Charley and Roselyn did not leave the windows as they thought that the plane that just landed was not Jon's. They were in aw when the Manager of the airport came over to get them to bring them out to the Tarmac to the 737.
As they got to the plane the stairs were just being rolled up to the door and a man that was very thin was standing in the doorway waiting to come down the stairs in back of him was a pretty woman a few years younger. She was about 5'4" with a white blouse, no bra, a short skirt that was about 5 inches above her knees and of a material that moved with her body. They came down the stairs and Roselyn could see that she was not wearing any panties; her nipples were clearly visible in the light of day. They introduced themselves as Jon and his wife Courtney. Roselyn took an immediate dislike to Jon, but she liked Courtney. Charley notices the lack of clothing of Courtney also, unlike Roselyn he liked both Jon and Courtney.
Courtney and Roselyn talked for a few minutes as did Jon and Charley, then Jon said that he wanted to get started in a very businesslike I am the boss type of attitude. They ascended the stairs to the plane. The plane was divided up into rooms. They were in an office/ living room area as they entered the plane and were greeted by 4 man the flight crew with a male Flight Attendant
Jon sat down in the back of his desk with Courtney standing beside him; Charley and Roselyn were seated in front of the desk by the Flight attendant. The flight crew left the plane after being dismissed by Jon.
Jon started by saying. "I am very intrigued by older woman. The picture that you sent me does not do you justice; you are much more attractive in person. I am looking for a woman that will do as I ask. My wife is in agreement that I can do this. I am looking for someone that I can help out financially also as they do as I ask. If they refuse to do anything I ask then they will be paid and that is the end of our relationship. They will not be asked to do anything that will cause them any permanent damage or anything that will be illegal. Is there any questions so far?"
"You mean that I only have one chance. If I do not want to do something I am paid off and that is the end?" Said Roselyn.
"Yes that is right to a point. I will give you a few minutes alone with your husband to decide if you want to go on with this adventure. When you say no to one of them that is the end of the game, unless we can come to some other agreement or another adventure that is of interest to both of us." Said Jon.
Courtney came over with a contract for Roselyn and Charley to sign. She made it up as she is a lawyer. It stated in short that they were here of their own free will and could leave any time they wanted to. If they do not want to do as they are told then Roselyn will be paid off and the contract is null and void, unless a mutually acceptable adventure is accepted, in place of the one that was refused, by Jon, Courtney, Roselyn and her husband.
Roselyn signed it with some trepidation, while Charley signed it with a feeling of adventure.
Taking the contracts from them and handing them to Courtney he said. "The first thing we have to do is have these documents copied for your records. The next thing is to make you more to my liking Roselyn. Do you or your husband have any problem with you removing your skirt so we can alter it to my likings and remove your bra, as I do not like seeing undergarments through any lady's shirts."
Charley said. "I have no problem with Roselyn removing her bra and having her skirt modified."
With a very shaky voice Roselyn said, "Do you have a place where I can go to remove my bra and could you give me a skirt to replace my skirt while you modify it?
"Courtney please take Roselyn into the next room and explain to her what I expect from her at each of these meetings and I will explain to Charley what I expect from him." Said Jon.
Both women retired to one of the other rooms, a bedroom, Once inside Courtney said. "Jon expects you to be dressed as I am at all times that he meets with you. By that I mean that you wear a skirt or dress with no bra or panties on. Jon does not like women that shave all the pubic hair off their pubic area, therefore I will show you how he likes to see a vagina trimmed." With that Courtney lifted her skirt to expose her vagina for Roselyn to see how she is to be groomed when she meets Jon.
A shocked Roselyn looked on as Courtney showing her most intimate being to Roselyn opening herself up without humiliation or embarrassment. Courtney's vaginal area was clean shaven but she had a perfect v of pubic hair on her mound. Roselyn was blushing to her toes and she could feel her vagina begin to moisten.
"Remove your bra and give me your skirt so we can modify it." Said Courtney.
A very humiliated Roselyn removed her blouse and removed her bra. She was stopped from putting on her blouse by Courtney and she had Roselyn put her hands at her sides so Courtney could look at her breasts. Courtney took each breast in her hand inspecting each. Roselyn's breasts are sagging somewhat, but looking very good for having 3 kids and being 50 years old. Her nipples are large even though her breasts are not very large they looked to be a very good match for the rest of her body. Roselyn's nipples became very erect with the ministrations of Courtney.
"Your breasts look very good Roselyn." Said Courtney as she rubbed each of Roselyn's nipples to excitement both were like pencil erasures by the time she finished rubbing the older woman's nipples
Blushing Roselyn Put her blouse over her shoulders but did not button it. She then removed her skirt and gave it to Courtney. She left the room with it then returned to Roselyn, who still did not have her blouse buttoned up.
"You can keep your panties on for the time being until your skirt is altered. I need to go over what is expected of you from Jon when you first meet with him each time. We are going to get a wardrobe for you to wear when you meet with Jon. You will wear a blouse that buttons down the front and skirt or Dress that buttons all the way down the front. Jon will expect you to let him to examine you each time that you meet with him. He does that to me every day also. I will show you this afternoon when we go back out there what is expected." Said Courtney.
Roselyn was beginning to regret that she wanted to meet Jon and signing the contract. She could not believe that she is topless presently in front of Courtney, not buttoning up her blouse, and standing here in just her panties while Courtney is telling her that she will be taking them off after her skirt is given back to her.
Courtney walking out into the main room again said to Roselyn. "Follow me so I can show you what is expected of you when you first meet Jon each time. Oh there is no need to button up your blouse."
Reeling from humiliation Roselyn followed Courtney out to the front area with her head down blushing furiously. Courtney said to Jon. "I would like you to demonstrate on me the inspection that you will put Roselyn through each time that she comes here to meet with us."
In front of Charley, Jon and Roselyn Courtney unbuttoned her blouse all the way and stood in front of Jon with her breasts completely exposed. Jon took each breast and examined it paying particular attention to her nipples. Roselyn was in aw that Courtney stood proudly in front of her husband and even smiled at Roselyn as she was being examined in front of everyone. When Jon was finished with her breast exam Courtney turned pulled her skirt up to her waist and rested her hands on the table with her legs spread for her vaginal inspection. Jon reached down with both hands to expose her anus, then inserted his fingers in her vaginal opening after he washed them. He had her turn around and he kneeled down in front of her. Running his hands through her pubic hair he reached between her legs and opened her labia for a visual inspection. Everyone in the room could see Courtney's clit erecting as Jon manipulated her organ.
Roselyn could see Courtney becoming very moist and she could feel herself becoming moist also. Roselyn hoped that her panties did not show signs of her excitement. Jon looked over at Roselyn and could see her nipples were erect. She was very embarrassed to think that she will have to go through the same inspection every time she meets with Jon.
The flight attendant came into the room while Courtney had all her womanly charms exposed and Roselyn's breasts were exposed. He handed the skirt to Roselyn. She stepped into it right in front of everyone it was about 6" above her knees and was slit up to the waist on each side and the front and back of the skirt. She walked to a mirror that was in the office as she walked toward it she could see her panties with each step she took. It was embarrassing for her to think she was that exposed she all but forgot that she was nearly topless her breast exposed as she walked.
"Now that your skirt has been altered it is time to take off your panties." Said Charley her husband.
Roselyn did not know what got into her but she reached under her skirt and pulled off her panties. She gave them to Jon when he asked for them. He felt them and found that they were very moist. A good sign he thought to himself.