Janet in TrainingChapter 8 The Competition
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Janet Walks On The Wild Side free porn video
Carl and Janet were both in their fifties and had been married over thirty years. As difficult as it may be to believe, Janet had remained a virgin until her wedding night. Both of them had remained faithful to each other during their entire marriage. They have always had a strong sex life together.
Janet was a very conservative, modest woman. She never wore any risqué clothing in public, made sure her dresses or skits were not too short and never displayed her ample cleavage. She was a very “well built” woman standing five feet seven inches tall, weighted one hundred and thirty pounds, and sported a 36D-28-34 figure. She would always say that she definitely had been passed down some of her mother’s good genes, especially with her breasts.
As the years went by, Carl began to fantasize about Janet being with another man. He would occasionally say things to Janet in sort of a joking way to get her reaction. Janet was never interested in hearing any of that and would tell Carl that something was definitely wrong with his thinking. Carl never gave up. Although it could be several weeks or months between bringing up the idea, he continued to mention the idea in one way or the other. He always got the same response from his loving wife.
Over the years their sex life cooled off as it does for most married couples as they get into their fifties. They were at the point where they were having sex one or two times a month and sometimes it was only a hand job or oral sex. Of course Carl was always up for a good fuck but most of the time Janet was not.
They received a wedding invitation one day from a very good friend of theirs whose daughter was getting married. The wedding was going to be in another State and of course they would be going. The reception was going to be at a hotel which made it convenient as they would be staying at the location.
Carl began to sort of tease Janet again about maybe she could hook up with a young stud at the wedding and perhaps fulfill his fantasy. Janet became very upset with him and his constant mentioning about her being with another man. At that point Carl offered a deal to Janet. He promised he would never bring the idea up again if, in return, Janet would let him buy her the clothes she would wear to the reception. Janet thought about the deal for several minutes and agreed only on the condition that she would see and try on the clothes before they left and if they met with her approval it would be agreed upon.
Carl wasted no time and within a few days he presented Janet with boxes and bags from a few stores which contained her ensemble for the wedding reception. Janet went to the bedroom with the packages to try on the items that Carl had brought home. She could imagine what he probably had purchased but made a promise to herself that she would keep an open mind. After all, wearing these clothes for one night among a room full of strangers would be a small price to pay for never having to hear Carl suggest to her about being with another man.
As she began to open the packages there was no surprise; a black dress that was much shorter than she would normally wear and a neckline that plunged and would expose her cleavage, a black sexy plunging, push-up bra, lacy black bikini panties, a black garter belt with thigh-dark stockings, a pair of very nice shoes with stiletto heels and finally a very nice gold necklace with a matching ankle bracelet which again was something she never considered wearing.
She looked at the ensemble that she had placed on the bed and thought to herself that there was no way she would wear this outfit anywhere. She stared at the items for a few minutes and looked at herself in the full length mirror in the bedroom. She did begin to wonder how she would look wearing the items. Her curiosity finally got to her and she stripped naked and began to try them on.
First was the garter belt, an item that she never had owned. She then put on the nylons and attached them to the snaps. She looked at herself in the mirror. “Hmmm, pretty sexy” she thought to herself but had to admit that if she did agree to go through with this idea of Carl’s she would definitely need to at least trim her full bush or perhaps even shave it off completely. After a few minutes she decided to put on the rest of the items. She slipped on the bikini panties and then the bra. The plunging, push-up bra made her 36D’s look like 38DD’s. She put on the dress and then the jewelry and stiletto’s. She gave herself a once-over look in the mirror and then went downstairs to see what Carl would say.
As Carl saw her approaching him, his eyes got big and his mouth dropped open. He was looking at the sexy wife that he had always envisioned. “Well, what do you think?” Janet asked. “You are absolutely stunning”, Carl replied.
Janet had to admit to herself that she did look sexy but definitely not slutty. She sat down in the living room and crossed her legs. The hem of the dress rode up her thigh and nearly exposed her stocking top. The ankle bracelet shown nicely on the leg that was crossed over.
“Well, is this how you want me baby? Is this how you imagined I would look?”
“Oh Honey you look terrific. How do you feel?”
“You really want me to be honest with you Carl?”
“Yes, of course.”
“I feel like a whore waiting for some strange guy to come up to me and tell me he wants to fuck me. That’s how I feel. Is that what you want?”
“No, of course not. I just want you to feel…you know…more…how should I put it. More womanly.”
“Well Carl, if this is what you want then I’ll do it but I better never ever hear you mention, hint or joke again about me being with another man. Do you understand?”
Carl just nodded his head in agreement and mumbled that he did. “Can I come up and watch you undress?”
Janet smiled at him as she felt her panties becoming moist from being dressed so sexy. “Sure Honey. You can even help me if you want.”
They went up to the bedroom and Carl helped her get out of her dress and then admired her for a few moments as she stood there in her sexy undergarments. “I want to fuck you”, he said.
Janet did not say a word. Carl went over to her and positioned her next to the side of the bed. He knelt down, removed her panties and then gave her a guiding push so that she was seated on the bed. As he knelt between her legs, he spread them apart and ate her pussy until she orgasmed.
As Janet lied there in her afterglow, Carl stripped, stood between her legs, lifted them up as he stood at the side of the bed and fucked her. It didn’t take long until he was filling her pussy with his cum. As Carl was grunting and filling her, Janet had a second orgasm, something that she had not done in several years.
A few weeks later they were on their way to the wedding. Jane had packed everything that Carl had purchased and began to wonder if she would get many looks or if she would feel out of place. They checked into the hotel and had about four hours before the wedding and reception. Still dressed in their traveling clothes, they went down to the lounge to have a drink. Surprisingly, they met up with their good friends, the parents of the bride. Both couples were so glad to see each other as it had been a few years since they had been together. Their friends told them that everything was going like clockwork and they were actually able to take a few minutes to relax. After chatting for some time they had to leave to get ready for the ceremony and reception. Carl and Janet remained in the lounge and had one more drink before going back to their room.
They both showered and then started to get dressed. Having had a few drinks, Janet did not hesitate to putting on the clothes that Carl had purchased for her. As she was about to put the ankle bracelet on, Carl told her to make sure it was on her “right” ankle. Janet asked why and he told her it was more sexy as it was suppose to be a sign that she was married but dating. Janet gave Carl a strange look but at this point she didn’t really care.
The wedding and reception were beautiful. Things were going very smoothly. Janet noticed that she had received several “looks” from the men and a few women had complimented her on her dress. Needless to say, Janet was feeling comfortable.
The wedding reception was scheduled to end at 11:00pm and the clock was rapidly approaching 10:00pm. Janet had consumed several drinks, as had Carl and knew that she had only one more hour to wear her outfit and then would never have to hear Carl mention to her or tease her about being with another man. She was also feeling more “loose” than she had ever felt. She pushed back from the table a bit and crossed her legs. The ankle bracelet stood out on her dark shaded stockings as she dangled her leg.
Within a few minutes, one of the groomsmen came up to her and politely asked Carl if he could ask Janet to dance. Carl smiled and granted permission. The DJ had just started to play a fast song the happened to be one of Janet’s favorites. She accepted the young man’s request and they were off to the dance floor.
They danced to three songs and then the DJ announced he was going to “slow it down” a bit for the “lovers”. Janet was about to head back to the table when her dance partner asked her for one more dance. She decided to accept. The groomsman obviously had been drinking quite a bit and during the dance told Janet how beautiful and sexy she looked. He also told her that she had a great set of tits and offered to pay her one hundred dollars just to see them. Janet smiled at him and told him she didn’t think that was going to happen but did thank him for his compliment. The dance ended and Janet went back to the table to rejoin Carl.
Janet told Carl about the offer that had been made to her and of course Carl told her she should have accepted. Janet just gave Carl a look of disgust and didn’t say a word.
Now I must point out at this point that the entire wedding party were in their late to mid-twenties and both the bridesmaids and groomsmen were all very nice looking.
Over the next forty-five minutes or so, all of the groomsmen had danced with Janet and every one of them had complimented her on her attire and her breasts. And yes, they had all made cash offers of one sort or another concerning them. The “best man” was the last one to dance with Janet and at this point it was almost eleven o’clock. His offer was much more substantial than the others. He went so far as to offer five hundred dollars to titty-fuck her. Janet was both taken-back and surprised not say she was shocked both at the boldness of this young man and the amount of money he offered. At this point she just smiled and politely told him she was a very happily married woman and told him no.
Janet returned to the table and told Carl about the latest offer. Carl began to total up what had been offered to her and then began to recap. “Two of the guys offered one hundred dollars each to see them, two of them offered two hundred dollars each to feel them and one offered five hundred dollars to titty fuck you. That’s eleven hundred dollars for maybe what…fifteen minutes of showing your tits, having them felt up and one guy using them to get off. Where else could you make one thousand one hundred dollars in fifteen minutes?”
Janet responded, as she took a big gulp of her alcoholic beverage. “Carl, I love you and as far as I’m concerned my body is for you only. Besides we don’t need the money and... and…you know. I’m just not that type of person.”
Carl went on to plead the case for her to do it. He told her it would sort of fulfill his fantasy of seeing her with another man and also she could donate the money to breast cancer research which was a program she supported dearly as she had had a few women she knows develop breast cancer. He made his final point by telling her that no one here really knows her and she most likely would never see any of these people again.
Janet took another big gulp of her drink and Carl could tell she was thinking about it. Her mind flashed back to how she looked in the lingerie Carl had bought her and how sexy she felt in her new dress. The best man was very attractive and thinking about him naked with his young cock between her tits certainly heightened her arousal. She took one more gulp and finished her drink. She looked at Carl and asked him how he proposed this would happen. He told her not to worry. He would handle everything. He suggested she get herself another drink and take it back to their room where he would join her shortly and give her the details.
Janet did as Carl said and as she left for their room Carl rounded up the groomsmen. He spoke with them as a group and no one else was around to hear. He told them that his wife had reconsidered their offers. At this point the men looked shocked that she would tell her husband about what they had said. He reassured them that he was ok with the idea and told them this is how it would happen if they still wanted to go through with it.
Carl told them they should arrive at their room at midnight. The payment that they offered would be paid in cash when they entered and they would give Carl their cell phones and any cameras that they had as there would be no picture or video. He also told them that they would remain clothed and that they would not touch themselves in anyway while they were in their suite. He recapped with each of them what they had asked for and the price. He also gave them a chance to change their mind as to what they wanted to do with Janet and also told them that in no way would she fuck any of them. The groomsmen were all in agreement. Nothing changed.
Carl went back to the room and briefed Janet on what was said and what was going to happen. He also gave her another drink which she gladly accepted. Needless to say at this point Janet was intoxicated but not to the point that she did not know what she was doing. He told her to stay dressed and wait in the bedroom until he called her out.
They prepared the living room of the suite by setting up five chairs in a row and then putting down a sheet on the floor where eventually Janet would lie down and the best man would titty fuck her. Carl told Janet that he would take some pictures and also video the whole event so they could watch it later. Janet agreed and the suite was made ready.
Janet was in the bedroom when the groomsmen arrived. Carl opened the door and gave them a warm greeting and a smile. He immediately collected their cell phones and went over what each man was going to do and the price they had agreed to pay. Everything was agreed upon and the men pulled out their cash. One hundred dollars from number one and number two. They were only going to watch as they said they would pay to see her tits.
Two hundred dollars from number three and number four as they wanted to feel them. They would be allowed to feel her up for one minute each as agreed.
Number five, the best man, would remove his clothes completely and then would be allowed to titty fuck Janet until he came one time. It was made clear that he would not shoot his cum in her face or hair and he would make his best effort to shoot his entire load on her tits. He agreed.
Carl put their money in his pocket and placed their cell phones on the kitchen counter. All of the groomsmen took their seats in the chairs and Carl went to the bedroom door. He opened the door and told Janet it was time to come out.
Janet came out of the bedroom wearing exactly what she had been wearing at the reception. Carl looked over at the five men who seemed to look a bit disappointed. Janet walked over and stood in front of the five men. She smiled and asked how they all were doing. Each responded in a positive and polite manner. “Shall we get started”, she said with a smile. And with that she took a few steps back and turned her back toward them. She looked over at Carl and asked him to come over and get her zipper started.
Carl walked over and undid the clasp at the top of Janet’s dress and then slowly pulled down the zipper about six inches. He asked Janet if that was far enough and as she reached her arm behind her back she was able to grasp the zipper with ease. She told him that was fine.
She then began to pull down the zipper as the men watched. She pulled it down very slowly and her black bra strap became visible and shortly after the top band of her black bikini panties and garter belt. She turned around to face the men. She looked them in the eyes and continued to smile at them as she slipped the straps of her dress off her shoulders and begin to remove her dress.
All of the men seemed to be frozen as they watched. She took off her dress and then stood there in front of them wearing her black bra, black panties and garter belt, dark nylon stockings and her high heels. And oh yes, let’s not forget the sexy gold ankle bracelet. Janet slowly turned around a complete three hundred and sixty degrees so they could get a total good look at her.
Of course by this time all of them had full blown erections in their pants and were all dying to expose their cocks and start stroking but they knew the rules and remembered that Carl told them that any violation would earn them an immediate exit from the suite.
Janet turned her back toward the men again and they watched as she undid her bra clasp. She slowly slipped the straps off her shoulders and then held her bra against her breasts as she turned back around to face the men. Smiling at them she asked if they were ready to which they eagerly said “yes”. With that she pulled her bra off and exposed her tits to them.
None of them men were disappointed with what they saw. The two groomsmen who paid one hundred dollars to see them were told they could stay until the end and then they would all leave as a group.
Carl then announced that it was time for number three to get his feels in. The young man approached Janet and immediately placed his hands on her tits and squeezed them gently. He did this for a few seconds and then stood behind her and cupped them from behind. He also knurled her nipples which were very hard and protruding at this point and tugged them gently as far out as he could without causing her any pain. He cupped them again and then was told his time was up. He couldn’t believe how quick the minute went by but he obeyed and released her tits from his grasp.
Janet actually felt a bit sorry for the young man as he had paid two hundred dollars for something that went by so quickly. I’m sure what she said next was because of her intoxication but as the young man was starting to head back to his chair she asked him if he would like to “kiss the girls goodbye”. His face lit up and he quickly went back and gave each of her tits a nice kiss. She did warn him that no sucking was allowed.
After he took his chair, groomsman number four came up and did pretty much the same thing. He also was allowed a kiss on each breast.
Barely seven or eight minutes had gone by and it was now time for the best man to titty fuck her. Janet looked at him. Told him it was his turn and that he should strip completely. He did exactly what he was told and Janet marveled at his manhood which was close to eight inches in length, rather thick and stood out straight as an arrow.
With the man totally naked, Janet laid down on the sheet. Carl came over and handed Janet a bottle of sex lube. The young man wasted no time straddling her. Janet poured a copious amount of lube on and between her tits and then poured some into her hand and applied it to the young man’s cock. With everything well lubed he placed his cock between her tits and started gyrating his hips. His cock was sliding between Janet’s tits. Janet used her arms to push her tits together giving his cock a nice firm crevice to enjoy. It was probably less than two minutes when he yelled ‘I’m gonna cum”. Carl blurted out “remember on her tits”. At that point the young man pulled his cock out from between her tits, took his shaft into his hand and stroked himself off sending several long, thick, white ropes of cum all over Janet’s tits. As he finished he just remained motionless for a short time breathing rather heavily.
Janet looked up at him and said “I hope it was good for you.” The young man nodded, smiled and said “Oh yea, it was. I hope it was good for you too.” Janet smiled and told him that it was.
As the young man stood up, Carl came over and handed him a towel to clean his cock off before he got dressed. Janet watched and was suddenly overcome with a feeling that she wanted more. She looked over at the other four groomsmen who all seemed to be squirming in their seats. She told them that if they behaved and did exactly what she said they could all cum on her tits. Carl was more surprised than the men at this point. She told them that they could come up to her two at a time, kneel down, one on each side, drop their pants to their knees and jack off on her tits.
Needless to say they all bought into it. They did exactly what Janet had told them and soon Janet had four more loads of cum on her tits. She remained lying there until the men got themselves together and left the hotel room. Carl quickly came over with some towels and wiped up most of the cum from Janet. He then helped her to her feet. Janet wiped up the rest and before she went to the bathroom to wash her tits and upper torso Carl asked, “Well…how was it?” Janet looked at Carl, took his hand and then placed the palm of his hand on her crotch. Her panties were soaking wet with her sex juice. She looked at Carl “That’s how it was. It’s been a long time since my pussy was that excited.” And with that she went into the bathroom to finish cleaning up her tits.
When she came out she was still dressed in her lingerie. Carl led Janet into the bedroom where he removed her panties, ate out her pussy and then fucked her causing her to have multiple orgasms. They fucked four times before they got out of bed in the morning. Just before they got up, Janet told Carl there was something she wanted to tell him. Janet then told him that if the best man had told her he wanted to fuck her pussy, she might had let him. Carl was taken back. The reality of his wife actually fucking another man became a bit more real.
“So now you want to be a whore huh?”
“Well isn’t that what you have wanted for all these years?”
“Well I guess so.”
Well…maybe I’ll think about it,” were Janet’s last words.
If this story gets favorable reviews I definitely will do a follow up in the future.
Cayleigh
- 05.06.2022
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