Cynthia's Affair Ch. 04

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Frustration and success.
6.2k words
4.33
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Part 4 of the 4 part series

Updated 09/22/2022
Created 03/09/2014
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As Cynthia left the therapist's office, she was determined and optimistic. She had said little in that last meeting, only listening and absorbing what was obviously good advice. She was resolved to be more aggressive, make herself approachable and, if the opportunity arose, to carry through. The sessions with Dr. Butler and the intensive introspection of the last few months had cleared her mind and let her see what she really wanted. The genesis, of course, had been David's thoughtless and humiliating behavior, leading her to consider an affair in retaliation.

Now, however, she realized that she wanted extramarital relations for the experience, for her own needs and personal desires. She still wanted, badly, to have the romantic closeness that she was not getting at home, the lack of which had started all of this, but she now was more aware of other potential sexual pleasures. Adultery and bisexuality, or their combination in a threesome, which would have been an anathema two years ago, now were tantalizingly attractive and not even particularly sinful. Certainly, the first of these was no longer taboo, and, as she prepared for the state-wide administrator's meeting, it was not school business that occupied her mind.

It was an all-day conference on Saturday, with an evening dinner and social session Friday, and, while she normally went to those things with another woman, this time she deliberately planned to go alone. Looking over her clothes, she realized that virtually everything she could pack shouted "high school principal," conservative and safe. Her underwear was serviceable, covering her very adequately, and was quite suitable for that "high school principal" outerwear. A quick trip to the local mall produced a much lighter, semi-frivolous dress for Friday night, unlike anything she had worn in years. A visit to Victoria's Secret resulted in a selection of lingerie that she normally would have considered to be scandalous, but now suited her desires exactly! These, along with a brief and completely sheer nightgown, the same one that had failed to tempt David, prepared her for what she hoped (and, a bit, feared) would be a memorable night. Unfortunately, the night was memorable only for disappointment.

She dressed for the evening with great care and with trepidation. She stood in front of the mirror, wearing a sheer, lace bra and panty set, coupled with a matching garter belt (instead of her usual pantyhose) holding up long, dark stockings. She was startled at just how sexy she looked, hardly like a mature married woman with three college-age children. When

she put on her dress she, unfortunately, but inevitably, was not as sexy, but she was still a very appealing woman. When she went down to the reception, she unquestionably was the most attractive woman there and admiring glances followed her into the room. Women she knew complimented her fulsomely on her dress and her appearance, with just the right amount of envy (or jealousy) in their voices.

Male reaction, however, was peculiar, basically dividing into two types of behavior.

Some acquaintances made a pro forma compliment on how nice she looked and, then, that out of the way, treated her as just another colleague, talking about school budgets, discipline problems, etc., soliciting her opinions and recommendations. Feminists would have been delighted, but, right then, Cynthia did not want to be seen as "one of the boys!"

Other men she knew just didn't seem to know how to deal with her. She was a high school administrator with a good reputation of handling difficult situations, a woman who most definitely was not a shrinking violet when dealing with administrative heavy-handedness. She handled herself well in the rough and tumble battle for limited resources. Yet, here she was, pretty, even delicate, dressed in a light, flowery, very feminine dress! They just didn't know how to relate to such contradictory views of the same woman, so their reaction was to back off and, in effect, ignore the paradox.

So, between those who, for practical purposes, dismissed the differences as unimportant and went on with "business as usual," and those who couldn't deal with it and turned away, Cynthia was left frustrated. There was no magic contact, no eyes across the room, no proposition ...... no anything! After the dinner and meeting, she went back to her room, removed the pretty dress, removed the sexy underwear, put on a mundane sleeping-type nightgown, and went to bed, alone.

Describing the disappointing occasion with Cathy later, she had to admit that she had been both disappointed and relieved. If someone had been overcome by her new sexy allure and swept her off of her feet, she would have loved it! Being undressed, her Victoria's Secret revealed, and carried off to bed for a night of erotic sex play, would have been perfect! However, she had to admit that no one there that evening raised her blood pressure or caused her juices to flow. "I honestly don't know what would have done if someone had suggested something! I really want something to happen, but, I guess, I want something more than just having sex....heaven knows. I do want that, but I just couldn't see being that close to anyone who was there! It was fun, though, being dressed like that, thinking how they would react if they had been able to see under my clothes. Boy, would they have been surprised at what I had worn underneath! It was funny enough to see how a lot of them reacted to seeing me 'out of uniform,' anyway!"

"You'll have to show me that underwear sometime -- it must really be something! As far as the people at the meeting are concerned, I'm not surprised at their reaction. School administrators are not the most 'with it' people in the world! Still, it's too bad that things didn't work out. Unfortunately, I doubt that you will be satisfied to have a one-night 'fling' with someone you really don't know. What you want is a relationship, and I don't think you can get that at a conference unless you just are with someone you know and something spontaneously develops. A friend with whom you can have sex, like with Don Anderson and me, is perfect. Just pleasant, intimate fun with no hang-ups, but there is no way that you can arrange that. On the other hand, I think that you could enjoy the physical excitement of having sex with a virtual stranger if a spark did fly between you. Maybe you'll have better luck when we're at the NEA convention this fall."

"Maybe, but I'm pretty discouraged. You know, it's been almost two years since all this started. I was worried then about what was going to happen when all the kids were gone, and that time is now! Joanie [her daughter] was a high school sophomore then and she will be a college freshman this fall. Two years of thinking, counseling and, for months now, therapy, and I haven't done anything! All I've done is find out that I really want...no need...something, and, damn it, I can't get it! In books and movies two people meet and fifteen minutes later they are in bed! I know that real life and fiction are two different things, but having some kind of extramarital experience shouldn't be this difficult!

"In any case, I'm going to try something else. You know how David and I spent a few days with Julia and George Simpson in North Carolina three years ago. They invited us to come down again, and we're planning to go there in July and I'm going to see if anything can develop. I've always been close to both of them, and, while I don't know if a threesome is possible, as Dr. Butler instructed, I'm going to make myself available. I was thinking of them in that threesome fantasy I showed you, and I'm going to see if anything can actually happen. I still don't know about doing anything with her, but I've always thought that he was attractive. We'll see!"

So, the third week in July, Cynthia and David drove to North Carolina, arriving late afternoon. Things worked out as in her fantasy at first. They talked, had dinner and, around 10:00 pm, David was exhausted and went to bed. Things continued well, with a late swim proposed by Julia followed by Cynthia's hesitation about not having gotten her suit out yet. Things immediately went sour, with Julia, rather than proposing a nude swim, simply said, "Oh, that's no problem! You can wear one of mine, we're almost the same size."

Unfortunately, Julia was right and her suit fit well enough. It was very snug over Cynthia's considerably larger breasts, making it impossible for it to "accidentally" fall down, eliminating that ploy. (Interestingly, when she had fantasied about a threesome, the other woman had larger breasts.) Once again, hopes for an erotic idyll evaporated, and after a quiet, refreshing, but frustrating, swim, they all went to bed. For the next three days, they had an enjoyable visit, marred only, for Cynthia, by the sense that another possible opportunity was passing by.

On their last day there they had been in the pool for some time, Cynthia lying on a large float while the others swam around. She really had hoped that something would happen during their visit, but all she could see now was a long trip home feeling even more depressed than she had before. Finally, her frustration boiled over, and she decided to do something herself! David and Julia were by the steps, some distance away, and, taking the opportunity, she reached behind her neck and undid the tie holding her suit up. Making sure that her back was turned toward the others, she pulled the suit down almost to her waist and then stretched the front up just enough to drape over her breasts. Calling to George, she asked him to help her oft of the float, something she usually did. Now, George always had been interested in her breasts, which are much bigger than Julia's small A-cup, and when he lifted her up or helped her off, he almost always managed to "accidentally" touch them briefly. The touch was never overt or long lasting, something that she had to notice and react to, just an incidental part of helping.

This time, however, things were different. Cynthia raised up and he put his hands at her waist to help her off, but, as he did so, the suit top slipped down and both breasts popped out. He was so startled at the exposure that he just held her there, staring at the turgid, pink nipples projecting toward him. Cynthia broke the trance by leaning forward and sliding off of the float, and, as she did so, his hands slid from her waist onto the breasts under the water. At first his touch was tentative, but, when she didn't immediately pull away and cover herself, George took advantage of her acquiescence and cupped and fondled both breasts. The entire episode didn't last more than a minute, if that, ending when Cynthia leaned back, giving him one, last look, and, then, reluctantly pulled the suit back up. Nothing was said the entire time, and no reference was made to it later, but the mutual enjoyment was obvious in the smiles they gave each other as they left the pool.

There was, however, one more, relatively minor, sexual contact between them. When they dressed to prepare to leave the following morning, Cynthia put on a light, summer blouse without a bra. When standing by the car, exchanging the traditional goodbye kiss, George was able to feel her breast with only the thin fabric in the way. It was a very pleasing way of saying goodbye!

As she recounted the story to Cathy later, she admitted that she had been shocked at her own behavior. "I've never done anything like that in my life before! I still can't believe that I not only took the initiative, which I certainly have never done, but that I actually deliberately exposed my breasts and let him feel them. That's the first time anyone, other than David, has touched my bare breasts since we were married! But, boy did I enjoy it! Something else, too. After that I know for certain that I do want to do more. I still am not sure about a threesome or if I'd want sex with both George and Julia, but I am sure that I'd let him screw me if I had the chance! I thought... no, I was almost sure... that I would enjoy extramarital sex, but now I know it! You and Dr. Butler are the only people I could admit that to, but it's the truth."

"Well, I'm certainly glad that something worked out for you down there. That really did take a lot of nerve! It's good that your mind is clearer on things, but I'm afraid that the real problems still exist. Wouldn't you know that your first possible prospect is way down in North Carolina!"

Cynthia giggled, almost like a teenager, saying, "I don't know about that! Julia has been trying for years to get George to come north and visit us, but he just doesn't like to travel. But, just before we left, he said that since the kids are in college and we have so much room now, they might think about coming up in the spring! I wonder what changed his mind!" Then, more seriously, "I know what you mean, though. There certainly are no prospects around here, so I guess I'll just hope something does develop at the NEA meeting in Chicago. I do feel better about things, though."

The rest of the summer passed rapidly, as usual, with getting a daughter ready to enter college, combined with her normal administrative duties, keeping Cynthia well occupied. Finally, however, with Joanie off to freshman orientation, she had to endure "empty nest" pangs in a house that suddenly seemed too large. Worse, her fears about her relationship with David were realized. There were no overt marital problems, just a feeling of living with a close relative, not a husband. The wall of indifference that had sprung up two years ago persisted and Cynthia admitted to herself that she felt no real urge to tear it down. The exhilaration coming from the brief sexual encounter with George had worn off, but remembering the excitement of that relatively minor infidelity made life with her husband seem blander than ever. Thus, when she and Cathy took off for the annual NEA convention -- four nights in Chicago -- she was more than ready for a new adventure. Cathy was also eager, for Don Anderson had called saying that he would be there Saturday, the last night, and would take her out to dinner. So, both women had something to look forward to.

They arrived in Chicago, registered at the NEA table and went sight-seeing before attending the evening banquet and "get-together" reception. The following day they attended workshops that interested them, met a number of people they knew and, then, just mingled. Unfortunately, while Cynthia, surprisingly, found several of the meetings to be of value, she met no one that interested her personally. It appeared that this conference would be like the last one, professionally useful but not what she had hoped for otherwise. That night she was quite depressed, feeling old and unattractive, doomed to a dull, boring, uneventful life, and nothing Cathy could say would console her.

However, on Friday morning her luck seemed to have changed for the better. Attending a 9:00 AM session on teacher evaluation, Cynthia saw an attractive older man (probably about her own age, she 'thought ruefully) who looked familiar, sitting alone. Taking the seat beside him and introducing herself, she discovered that his name was James Cooper, D.Ed., and they realized that they had taken several graduate courses together years ago. After the session was over at l 1:00, they sat there talking about teaching problems, measuring teacher performance, etc., finally realizing that almost an hour had passed and that it was nearly noon. He invited her to lunch, and they continued talking, leaving the professional conversation and turning to more personal history. He was married, had two children about the same ages as her sons, and was an instructor at a small teacher's college -- in a town no more than 25 miles from Cynthia's school! Ironically, they had flown all the way to Chicago to run into each other when their schools were no more than 40 minutes apart! They talked about all the things they had done, places they had been and, suddenly, to her profound shock, Cynthia realized that while the elusive spark had not flashed between them across the room, it had done so across the table!

She was very attracted to him and, obviously, her feeling was reciprocated. They each had meetings at 1:00 pm, so they had to separate, but preparing to part, he said that he was conducting a session that evening and that it would be through by 11:00 and asked if she would be free later for a drink. Without thinking, Cynthia immediately replied, "Oh, I'll be free all night," Then suddenly realizing what she had said, quickly continued, "Oops, I didn't mean that quite the way it came out!" He just laughed and they made arrangements to meet after the session. As he started to leave, however, Cynthia nerved herself and, following Dr. Butler's advice on being more aggressive, called him back and said, softly, looking down shyly, "I really did mean what I said about being free all night."

Jim just reached out and lightly squeezed her arm, saying, "I really hoped you did!"

Cynthia went through the motions of attending another workshop before hurrying upstairs, eager to tell Cathy her news. Cathy was almost as excited as Cynthia, complimenting her on her boldness and encouraging her to be equally as brave later. After a quick dinner, Cynthia showered and began to dress for what promised to be a very erotic night ahead. Cathy watched as she donned that extremely revealing, extremely sexy lingerie purchased for just such an occasion. As Cynthia pulled up the long, sheer dark hose and fastened them to the supporters of the matching garter belt, Cathy said, "Honey, in that outfit you would tum anyone on, man or woman! Dr. James Cooper is going to be very happy!" That, of course, was exactly what Cynthia needed to hear, and, putting on a short, full evening dress, she went to meet her fate.

Cathy, anticipating a night alone in their room, undressed and got into bed, novel in hand to read herself to sleep -- if she could keep her mind on the book rather than on lewd thoughts involving Cynthia. However, her plans for a restful evening were rudely interrupted fifteen minutes later. The door was flung open and Cynthia was back in the room, her eyes brimming with tears of utter frustration. Shocked at her reappearance, Cathy sat up, her face filled with concern as she asked, "What happened, honey? What's wrong?"

"Everything's wrong, damn it! I got to the meeting room and it was completely empty and dark. A bell hop came up and asked me if I was Mrs. Anders and gave me this note from Jim." She handed Cathy a slip of paper with a short note that read:

Cynthia, I just got a call from home saying that my son has been in a car accident. I have canceled my session and I'm leaving right away. They don't think it's serious, but they're not sure. I called your room, but you probably were at dinner. If I can, I'll call you tomorrow or, if not, I'll write to your school. I can't tell you how disappointed I am. Jim

"I just can't believe this. I finally get exactly what I want and it all falls apart just like that!" Her face was the picture of disappointment, and she paced around the room, totally out of character with her usual calm demeanor. It was a good half hour before she finally slumped down in a chair, depressed and forlorn. Cathy tried to reassure her, pointing out that Jim clearly was very interested and her assignation was just postponed, not ended. Her comments finally seemed to have effect and suddenly, with a determined look replacing the disappointment on her face, Cynthia stood up and stripped off her evening dress. Standing there in her panties, bra, garter belt and hose, posing gracefully, she asked, "Do I look good like this? Did you really mean that I that I would turn anyone on, man or woman dressed like this?"

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