Meeting Karen Pt. 01

"Your decision to become a female Carrie?" as Karen released Carrie's strand of hair.

Carrie smoothed her dress as she settled, considering whether she should further reveal her true feelings, and then she looked at Karen. She was still upset at the idea that Karen had suggested. She could still see quite a bit of Karen's upper thigh, as the woman sat beside her.

Karen smiled, as she understood Carrie's look.

"So what Carrie. You saw my panties,"

Carrie picked up her wine glass, as she needed to try to calm down.

- - - - - - - - - - -

Gary had worked for almost three years with Karen's husbands' firm. He had been with two other firms, before he accepted the position with Charles' small law firm. At his previous position, with a larger firm, he had met a woman. They had slept together several times, but Monica had quit her position and had decided to move to another city. Gary had enjoyed Monica's ideas of variety and one night while in bed together, Monica asked him, and he had accepted, her request to wear a pair of pantyhose while in bed with her. Monica loved the feeling of nylon covered legs rubbing, together with Gary's, and they would ruin two pairs of hose' each time they played her game.

The salary Gary received grew as Charles appreciated Gary's patience and meticulous legal research. Gary did not aspire to become a partner, as he enjoyed the investigations, rather than the legal courtroom representation.

Early on, while employed at Charles' firm he was introduced to Karen, at the year-end party. Gary had watched a slightly inattentive Charles around the beautiful Karen. She was at about five years younger than Charles, and therefore nearer in age to Gary. He wondered how his boss had met her, and why did the two seem a little remote? Gary couldn't begin to understand the needs of a lovely woman, and the care necessary to look so ravishing. Karen was dressed in a red dress that first evening, which fell to just below her knees, and she worn gold sandal heels. Her hair was up and woven in a tight, careful twist, and a small diamond cluster clip held it all together. Gary had to purposely look another way, since he was so attracted to Karen, and her visage. For her part, Karen seemed to know all of the other staff members and spent time with each. When Gary met Karen that first time, at an office gathering, he was blown away, for Charles was kind of ordinary.

That evening Gary slipped out early to get away from Karen, and he went to a bar. He had to sort out his thoughts.

Sitting alone at a bar with a wide TV screen showing a baseball game, he drank his pint. The place was half empty when he watched as a couple came in and sat in the stools opposite him. Slowly Gary began to notice that the girl on the right seemed cute and normal, but her friend was clearly a cross-dressed man. Gary could hear a good bit of their conversation and he pretended to be into the game but was trying to listen carefully.

The girl across the bar giggled.

"See even the barmaid didn't look twice. No one cares Skippy," she said, and she turned and kissed her friend.

"Thanks for doing this with me Skip," the woman said.

"You know, you could definitely pass with just a bit more work. Why, I spent only ten minutes on your face. That's half of the time I need to be presentable every morning."

Gary listened as the man, Skippy, spoke of the weird sense that everyone was looking at him.

"It's unnerving to think. Just look at that guy across from us. He could have already decided I am a fruit!" but Gary didn't flinch or look in Skip's direction.

The woman, maybe nearing thirty years old, stopped Skip.

"You did this for me, not for yourself honey, so I am the one who is happy," her hand came up and adjusted Skippy's hair.

"I think we will need to get a better wig, and then I'll be riding you all night sweetie!" and Gary watched as the woman turned and passionately kiss her friend, not worried about what the other patrons thought.

Gary was shocked by their comfortable display of this erotically charge moment, he now watched as the woman caressed the clearly feminized man's chest. Gary had become rock-hard and had to look away. He downed his drink, stood up and dropped a ten note on the bar and left. The two events of the evening would propel his near future.

Two months after the bar incident, Gary had begun: the investigation he determined would be Carrie's and she would, select, decide and determine her true self. The opportunities slowly developed as she re-defined her world from the remnants of Gary's life. During that first year, as Gary initiated his dressing, he was less careful with the look and details of his Carrie look. He considered if it was a fetish, as he dressed almost daily now, but there was something that drew her into this sensual shift each evening, after arriving back at the condo.

- - - - - - - - - -

Nearly ten months later, Gary's phone buzzed, while he was on his lunch break and down the street from the office. It was Charles' cell number.

"I'm glad that you picked up Gary," Charles said.

His boss was in Court and he required a file immediately, but it was at his home, and he couldn't reach his wife Karen.

"I need you to head to my house, now, immediately Gary. The file is sitting on my desk, in the upstairs office. My wife might be around, somewhere, but it seems she is not near a phone, and I can't leave the courtroom. Please hurry Gary."

The call went dead as Charles terminated the connection.

Gary drove the five miles to the home of his boss and parked in the drive. He had been here only once, for a weekend afternoon event. There were no other vehicles in the drive, and the garage door was closed. He found the hidden key as Charles had suggested, and he opened the large front door, calling out as he entered.

"Mrs. Stout? Hello. Is there anyone here?" but there was no sound.

He headed across the stone floor to the curving stair and moved up several steps when he heard a muffled sound; he paused.

Someone said, "Who is there?"

He was a woman's voice, but it was muffled, so Gary remained on the lower stairway. He waited for the person to come to the upper landing. A few moments later he saw Mrs. Stout.

"Hi," was all he could say, as he looked up to this lovely beauty.

Gary saw that she was strikingly dressed, again in a skin hugging black dress. Her face was radiant, and her lips were a deep red. Gary wondered if this was how Charles' wife dressed every day, ready for a club luncheon, or a party. He noted her tall red-colored heels and her nude legs, as he surveyed her from ten feet below. The dress edge stopped his review at her exposed knees.

"Oh, it is you Gary," she said as she began to walk down the stairs.

"I have just heard Charles' message," she stopped a moment as Gary continued to stare up at her. His eyes roaming back to her sexy heels, to her exposed knees, and his eyes settled on her face. She was a vision to Gary.

"Good afternoon. I believe the folder is there," as Mrs. Stout continued to descend the steps, she was pointing downward toward the doorway.

Gary watched carefully, each of her steps, and he noticed her details of her tall shoes, and her smooth, silky covered legs, and the hem edge of the tight dress, as it shifted with each step, as she now she was nearly beside Gary.

"There on the table," as she was directing his attention to the small mahogany side table, near the door.

Gary didn't immediately move, as he was studying Karen as she made each step. His rude observation lasted almost twenty-seconds now and he surprised Karen.

"Gary, close your mouth. Evidently, you're not used to seeing a woman of leisure," she said, as she stopped a few steps above from the where Gary remained looking up at her.

She smiled, "Charles likes me to spend his money, so I have adjusted to his whims," but as Gary turned to move away down the staircase, he heard Karen following him.

"I do apologize Mrs. Stout, I didn't mean to stare," he said as he walked quickly to the table near the door. He turned as the sound of her heels on the floor indicated that she was crossing the entry foyer, close behind him.

Gary turned briefly toward Mrs. Stout, and he smiled, "I'm sorry, but Charles is waiting for this. I do understand though, and I will try to be more respectful in the future, Mrs. Stout."

Again, she entranced him; noticing the details of her eyes, and her lips, and the hair wrapped about her ear, exposing the diamond stud.

Mrs. Stout moved and smiled, "Gary, you're staring once again."

She was now holding the edge of the tall glazed front door.

"It's Karen, with a 'K', Gary," and she now stood inches from him. Due to her heels Gary's head tilted slightly upward to look at her beautiful face, as she was a bit taller than him.

"Do you like me in red as well as the black dress?" she asked.

Gary was now perplexed, and he paused and turned slightly to again look at her, only eighteen inches away, and he felt his heart racing.

"Excuse me Mrs. Stout?" he asked, but he quickly understood. Mrs. Stout was referring to that last time she had been in the office. Gary must have been staring at Karen then as well.

She simply smiled, "Karen, and please remember that detail Gary. So, is it the red or black? Which do you prefer?"

Her smile was causing Gary to blush as she held the door, but he was so aware of each subtle detail, the décolletage of her bosom, the subtle color of her hair, the intense red of her lips. He glanced down a moment and noticed the small diagonal line of the slit in the dress hem, and as his eyes rose quickly, he admired the color of Karen's fingernails, a soft crimson, and the shine of her hair. Karen enthralled him.

Now Gary stuttered as he looked back at her face and smiled.

"Ah, well, ahh, both actually. You are lovely in either Mrs. Stout, but I really must leave," he took a step, but then turned.

Gary stopped, realizing his error, "I meant to say Karen," and he moved off the entry steps and walked quickly towards his car, but he turned again to look at Mrs. Stout.

He saw her smiling.

"Be careful Gary," she said as he now skipped to his car.

He got into the car and saw that Mrs. Stout was still at the open door. He started the car and turned the car to leave, and then he looked back as she waved.

As he drove off, he realized that he had been impolite, and he hoped that Mrs. Stout wouldn't reveal his intense inspection of her outfit and presence. It was curious to him that he wasn't undressing her, but rather reviewing every detail to remember. He could not recall being so close to such a beautiful woman before. Karen was intimidating. Gary wondered what that must feel like. He remembered a classmate in college, and his study partner, who once suggested that other women hated her. She was a very good-looking woman with a large bosom. He wondered if Karen was hated by other women like Claire had been. As he reminisced, he recalled a statement of Claire's: 'I've got great tits!'. He now seemed to recall that Mrs. Stout had a Master's from and small Massachusetts College, which had reputation of being quite difficult, so together with her appearance, she was intelligent also. He empathized that Karen may live with intense pressure. As he parked outside the Courthouse, he remembered her look while she stood near the top of the stairway, looking down at him.

Gary delivered the file to the courthouse guard and returned to the office. Later that evening Charles came into his small office, to apologize for the inconvenience.

"Did you see Mrs. Stout, or was she out?" Gary quickly realized he needed to be clear.

"Yes Charles, she must have heard the message you left, and she had brought the folder to the front door."

Charles then asked, "So you didn't encounter Karen?"

The subtle misunderstanding surprised Gary, "I did see Karen, briefly," he said.

Charles smirked, "She runs around all day, and Karen dresses to the nines, every day. I love her for that," and he turned to walk back to his office, but Gary stopped him.

"Here boss, the keys. I was in a hurry and I forgot to put them back in the hiding place," as Charles reached for the keys.

"If she was near, I know why you forgot," Charles turned and walked off, still saying something.

Gary heard Charles speaking, but he was now distracted, trying to find the reason that Karen was with this man. His boss was sort of good looking, and he had benefited from his family's connections. Though Charles could be charming, he was also aggressive. Gary could admit that Charles was quite intelligent, and he had a good sense of humor, but was that enough to have a woman like Karen remain close? Then Gary had a difficult thought, as he considered whether Charles was a seriously good lover, with a great cock. He had never thought of another man's genitals, and he shook his head to erase the vision he had now in his mind, of Charles's dick hovering above, but in Gary's imagination; in his mind, Gary saw that it was Karen on her knees.

Then it wasn't; in his mind he imagined it was Carrie, licking and sucking off Charles!

That evening Gary visited the mall. Nordstrom would become the supplier of the wardrobe Carrie wore each evening. The earlier purchases had been completed on-line. Now he wanted to learn more about the habit he had been developing, and shopping was necessary. He needed to better understand the grade of the fashions he wanted to acquire and wear. The first stop was a dancewear shop, though his was a private lesson, his dance instructor Toni had requested that Gary wear the correct leggings. He selected three pairs of leggings, each with stirrups, in black, as well as two pairs of the high-waist shorts she also required, which were really more of a thong.

The curious statement Toni had made, hit close, "Go with a garment one-size smaller, as you are losing the flab and the spandex can still fit you Gary."

At the women's department, he resisted the need to see how the dresses he had selected fit, instead buying several of each, sizes eight and ten.

"Shall I gift wrap these, sir?" the clerk asked. The twenty-year old assumed that Gary was shopping for a lover.

"Thank you, here is a note, to place inside the box Miss." He had thought of this detail, and knew that the returns could be mailed back, so long as the receipt was included.

Gary had been buying his intimate wear on-line, but today's encounter with the beyond gorgeous Mrs. Stout, Karen, had changed him. He was beginning to understand that his oafish, unsophisticated dressing would never be acceptable again, as Carrie evolved. He would actually buy several new bras and slips and panties tonight. He decided he would risk the humiliation and the questions.

An hour later Gary stopped for dinner and considered his newfound quest; he had decided his major goals included his feminine awakening and the empowerment it might bring. Gary intended to self-realize, through this new lifestyle and his re-education of his feminine self and Carrie's dressing. To Carrie her perspective had changed, and together with his new mental motivation, an important socio-cultural awareness was necessary. He would work on developing a historical consciousness of the needs of women. He would from this moment forward develop and support the basics of gender equality. He had come to realize that this was more than a quest. And she would be patient, as she knew that everyone's timeline might be different. At this moment he had changed the personal pronoun; Carrie knew now that this was her gender selection. Therefore, her focus must be on an inclusive life and her entire world would shift.

As she drove home that night, she considered how she would have to overcome the fear; the reality of being an ugly man, wearing a dress; though Carrie recalled that even Skippy, from the bar months ago, wasn't ugly, and that gave Carrie some measure of hope. She now had a pretty good notion of what she would need to do, to look and act like a woman, to feel feminine. Carrie had determined, that afternoon as she looked up, as Karen walked down the stairs, that she would accept that she was learning to live as a trans woman. She had read of the 'real life' tests, and Carrie knew her work life was still essential. That person had been Gary, a man of medium height, and now at one hundred fifty pounds, with a lot of dieting and exercising ahead.

Later that week, at the dance studio, Toni remarked.

"Something has changed Gary. Do you care to explain?" Toni had come across the dance space.

"I mean, to another woman?" Toni asked.

Toni suggested to Gary that she had noticed his voyeur like stare, and she now understood.

"In French this word, voyeur simply means, 'one who looks', and now I see your actions as a learning process, but Gary, you will need a new name."

Toni was the first person Gary had told of her transition plan, and Toni was supportive.

A month later Gary changed his name on the receipts for Toni's lessons to Carrie. It was a small step, but one she felt was correct. The processing of her legal paperwork would follow, but it would take Carrie months before she would initiate the action. Carrie was anxious that her legal career could be stymied by the request, and she was certain Charles would eventually find out.

A few weeks later Toni said to Carrie, "Most women, are ordinary and even homely, but also, though not beautiful Carrie, they can still also look sexy and gorgeous. It's an inquiry for each of us, learning to know how to be striking and unique. It can, but it doesn't include purchasing the most lavish clothing. But Carrie, you need to see that they are not 'lesser women', just because they don't look like models."

Toni was near Carrie at the dance bar, "But your face is," Toni paused.

"What is it Toni?" Carrie asked, as Toni carefully studied Carrie's face.

Then Toni moved away from the mirrored wall and folded her arms across her chest.

"You may be more lovely than I had first considered Carrie," hearing this Carrie smiled. "It could be the additional weight loss," as Toni came beside her at the ballet bar.

Carrie felt Toni touching her hair, "Even though you've decided to let your hair grow, and you haven't learned enough about blush and eyeliner!"

After making an effort and staying focused, Carrie's life did change, and she found it necessary to adjust her work attire, so that she could conceal the altered state of her body. It was easy to begin the hormone therapy, but there were issues, and her bottom's width was affected first, not her chest. She would race home after finishing work and remove the suits that she still wore each day. These now were too large, and her belt size was shrinking each month or so. Gary's old suits helped somewhat cover her changes, but several people had mentioned that her weight loss was clear.

"Your face and hands," were the typical comments others offered at the office.

Though Carrie was working out and dancing at the studio with Toni, who had become a friend, Toni hadn't mentioned her concerns, as Carrie had become comfortable wearing her feminine clothes to the studio. Toni tried to explain to Carrie the body shaming that she had encounter before she was dancing regularly, and she didn't want to make Carrie any more anxious as she adjusted to the hormones, and the emotions she knew Carrie was dealing with.

One evening Carrie did explain her quandary to Toni.

"Each morning I am happy as I assembly my outfit and begin to dress. Then I pull up those trousers and I know I will again disguise myself, solely for the good paycheck," and Toni saw how upset Carrie looked.

"I have resisted making the application for my legal name change," Carrie said softly.