The Leaving

by Jennifer White

   

Audrey paced the floor, as she waited for Jeff to arrive. She was sure that it was the big night! She had been dating him for almost a year, and everything was going perfectly. She was sure that he was going to propose to her, and she felt giddy from the excitement! He had been a little mysterious the past few days, and he had hinted that he was going to tell her something when he arrived. She pictured herself standing there on the altar, exchanging vows. How happy she would be!

Her phone rang, breaking her away from her wedding fantasy in her mind. She saw that it was Jeff's mobile phone, and she smiled. He was going to be there soon!

"Hello?" she said, as she picked it up.

"Audrey, listen" said Jeff. "I'm not coming over."

Audrey's hopes for the night were dashed, and she felt a deep disappointment.

"Aw..." she said. "Well what about tomorrow?"

"Not then either" said Jeff. "In fact, I'm not going to see you anymore."

Audrey felt the blood drain from her face. She couldn't have heard him right! No!!!

"What do you mean?" she said, her voice shaky.

"I mean that its over between us. I've got a new girlfriend, and I'm moving in with her. I'm sorry, but its over. It was a lot of fun, and I wanted to thank you for everything. But I'm planning my life with Loretta, and we're going to be married. So I have to let you go."

Audrey was so devastated that she couldn't even speak. The phone fell to the floor, causing the plastic to crack and the battery to fall out, as she stood there crying. How could he hurt her like that? If he was going to get married to another woman, then he must have been seeing her all along! Audrey had allowed him into her heart, and it was all a lie! She had let him go all the way with her, but he was seeing someone else at the same time! Her whole relationship with Jeff had been nothing but a lie!

She ran to her bedroom, threw herself on her bed, and broke down, sobbing. She screamed! She cursed! She shouted an anguished cry, before she rolled over and cried herself to sleep.

* * *

Far above the world, floating on a cloud, Goddess heard Audrey's desperate cries. It made Her feel sad to know that the males who She had created were still acting no better than they had when they lived in caves. Normally, She let events in the world go on without interference. But this situation called out for Her action. She devised a plan, and Her thoughts set it into motion...

* * *

Jeff walked confidently into Loretta's apartment. He had finally decided which woman he was going to commit to. Of course, he had been careful not to let Loretta know about Audrey! That would be a disaster, and he was careful to keep his story straight. But now he wouldn't have to worry about it; he had done the right thing, committing, which is what women all wanted their man to do for some reason.

He smiled when he saw Loretta. She looked awesome in her green plaid skirt! He loved the shape of the skirt, how it got narrow at the top where her waist was its smallest, and how it hung there, dangling straight across the front. She had on a black turtleneck sweater, which was nice and tight, making her boobs look so inviting. His eyes wandered down to her legs, which were covered in tights, which made the look so nice. And then there were the shoes on her feet, black with silver buckles, slightly pointy at the front, with moderate heels. They were just the cutest thing he had ever laid his eyes on!

"What are you staring at?" asked Loretta.

"Your shoes" replied Jeff. "They are just to die for! They're the "in" thing now. Where did you get them?"

"Oh, I've had these for a while, but they're back in style now" she said. "I'm surprised that you'd notice. Guys usually don't pick up on things like that."

"How could I miss them? They really compliment your outfit."

His tone sounded almost jealous of her, but Loretta ignored it. Jeff escorted her to his car, and they drove off downtown for dinner. She noticed that as they walked down the street, he seemed to be staring into all of the stores with women's clothing on display. She had a flash of doubt about her new fiancé cross her mind. All of the guys she knew who were *really* into women's fashions were all gay. She wondered if Jeff was gay too, and if she had just made a huge mistake. Now that they were engaged, was he showing his true self?

* * *

When Jeff got home from his date, he hurried to his computer. He didn't know why, but he felt like he *had* to find where Loretta had bought her skirt, and her shoes. He went onto the web sites for a dozen different clothing stores, browsing for skirts. He saved the pictures for the ones he liked, and thought were really cute. After three hours, he finally found the exact skirt that Loretta had worn, and he couldn't help it: he ordered one.

Then he was on to shoes. He looked at store after store, trying to find a match to what she wore that night. As with the skirts, he saved the photos of all the ones he thought were cool. But since Loretta's shoes were actually older, nobody had a precise match. But he did find one place that had a pair, very similar. He was going to order a pair, but they were all too small. He sighed, as he noticed that the store also sold intimate apparel. For the next three hours, Jeff surfed the web, downloading every picture he could find of bras, panties, girdles, garters, bustiers, corsets, and more.

* * *

When she was preparing for their next date, Loretta decided that she was going to test Jeff. It was late fall, and summer colors were definitely out. Instead of the muted browns she would normally have selected, she picked a pair of white pants to begin with. Since it was chilly, she went with a layered look on top, starting with a pink cami, then adding a powder blue sweater with a deep V neck. It was a color combination she would *never* dare ware at that time of the year. But she wanted to get Jeff's reaction.

When he arrived to pick her up, she saw a slight look of disappointment on his face.

"What's the matter?" she asked.

"I thought we were going out" he said.

"We are, dear" she said.

"Oh, that's good" he replied. "I'll wait here while you get changed."

Loretta felt a sinking feeling inside. He knew more about fashion than a man should. Something was wrong. She was relieved in a way that she had discovered it before they actually married. But it disturbed her that Jeff would keep such a secret from her. If he had held back about that part of himself, what else hadn't he told her?

There was also a second part to Loretta's plan. She told Jeff to wait in the livingroom, and she'd be back after she changed. While she was in her bedroom, he would be on the couch. She had her copy of Cosmo and Vogue sitting on the table, along with a copy of Sports Illustrated, which she had bought just for the test. When she returned to the livingroom, she saw what Jeff was reading: Vogue. He was pouring over it intently, checking out the latest fashion trends. Not good.

Loretta went through the evening, pretending that nothing was wrong. But she decided that she was going to have to confront Jeff about his interests the next time they got together. She just didn't have the courage yet. It would have to wait until another night.

* * *

Jeff looked at the clock. It was 3:00am, and he was tired. For the past eight hours, he had been downloading thousands of pictures from the internet. He had gone through the web sites for three different department stores, saving every single picture from the women's clothing department. He sorted the pictures into folders, based on how cute the clothing item was, as well as the model wearing it.

Jeff had memberships at several pornography sites. He downloaded the latest pictures from them as well, and sorted them into the same folders as his beloved clothing pictures. He didn't really notice that in his folder named "Best of the Best", there were more clothing pictures then there was porn. And of the porn pictures, every one that made it into that folder was a picture of a girl masturbating with a dildo, or one of a girl with her mouth wrapped around a man's penis.

For the past week, he had been obsessing over the pictures. He had a couple of gigabytes worth of them by now, but it wasn't enough; he needed to have more! While looking at the clothing pictures, sometimes he'd see something so cute that he couldn't help it; he *had* to order it. The boxes arrived in the mail, and he'd carefully take his new treasure out, and hang it in the closet. Or put it on his desk so he could see it while surfing the web. Slowly but surely, his collection of women's clothes was starting to grow.

Jeff marveled at the picture of one woman, wearing a little black dress. He loved her hair! And her makeup made her eyes look so pretty. He wondered how she did that. He started to explore sites that talked about makeup, products and techniques. Then he searched for sites devoted to women's hair. He had more pictures to save now, and more things to buy...

* * *

A month had passed since Loretta had made her discovery about Jeff. She finally decided that she had to confront him. If he didn't have a good explanation, she was prepared to give him back his ring. She invited him over, and sat with him on the couch, where they shared glasses of wine. She looked at him, and she was startled. It looked to her as if he had plucked his eyebrows a bit. He had never done that before!

She was going to start talking to him, and she put her hand on his shoulder. Her stomach sank when she felt something underneath, like a strap. Was he wearing a bra? Or a cami top? He had something on underneath that a guy shouldn't be wearing. She removed her arm, and looked him right in the eye.

"Jeff, I need you to be honest with me" she said.

"Certainly" he said.

"What are you wearing underneath your sweater?"

"Oh, its just a tank top T-shirt" he said.

"Show me" said Loretta.

"You really want to see it?"

"Yes. Show it to me."

Jeff shrugged, and pulled off his sweater. Underneath, he had on a really cute cami. It was white, with pink flower decorations stitched in on the front. It was made of a silky material that glinted in the light. The straps were thin and cute. Loretta realized that she had one just like it, but in green! He had bought himself something just like she wore!

"That isn't a T-shirt" she said.

"Yeah" admitted Jeff. "But I wear it like one. Cute, isn't it?"

"You're aware that normally only chicks wear camis?"

"Yes. But you wear one just like this, so when I put it on, it makes me think of you."

Jeff thought that was sweet, and she would appreciate it. He wondered if he should mention that he also had on a pair of her panties, which he had borrowed from her laundry basket the previous time he had visited her. But she didn't seem happy for some reason.

"Jeff, you're a very sweet man" said Loretta. "But this just isn't working out between us. I'm afraid I need to give you this back."

She took the engagement ring off of her finger, and handed it to Jeff. He took it and slipped it onto his own finger, which gave her the creeps! He didn't seem upset. In fact, he smiled. He was happy, because now he was going to have more time free to go online. He wouldn't have to interrupt his web browsing to go out and visit Loretta anymore. He wouldn't have to get out of his pretty clothes anymore, and dress in those dreadful things that men had to wear. He'd be able to wear a skirt at home, with nobody to bother him. He was going to have it made.

* * *

Jeff sat down in front of his computer. He had on an outfit very similar to one that Loretta had worn, with a green plaid skirt and a tight black turtleneck that showed off his large fake boobs he wore inside the latest bra he had purchased. He looked in the little round mirror from purse, and checked his lipstick to see if it needed to be touched up. He noticed a little bit of black under his eye from where his mascara had flaked off a bit, and he brushed it aside.

In the month since Loretta had broken up with him, he had concentrated fully on his new obsession with clothing. He had so many things now! He wore them around the house all he wanted now, along with his growing collection of accessories. He found a store online that sold women's shoes in larger sizes, so they could fit his feet.

Today he was downloading pictures of women wearing makeup, or sitting in chairs with beauticians applying the makeup to their faces. That was so exciting to think of being able to sit there, and for someone else to make you look pretty. He had learned so many techniques, but a professional could always do a better job than you do.

He paused to put his hands on his large fake breasts. He hadn't noticed, but more and more he had been saving pictures into his "Best of the Best" folder, with women holding their own breasts in their hands. He had been so into boobs that he felt compelled to go out and find a place that sold breast forms, so he could feel what it was like for himself. The first time he put them into one of his bras, the felt so *right*. Now he felt naked without them!

Jeff sorted some of the latest porn he downloaded. He found a wonderful picture of a woman masturbating with a dildo, and he moved that picture into his special folder. A few photo sets later, he found one with a woman going down on her man, which reminded him. He opened the box he had received the day before, with his latest purchase: a large, ultra-realistic dildo. He took it out, and placed it into his mouth, just like the girl in the picture was doing with her man. He felt such a thrill go through him! He just loved dildos, and he had started to collect more and more of them.

He crossed his legs, which were freshly shaved. Loretta hadn't even commented on it when he first shaved them. Of course, it was fall so they were hidden under his pants. But in the spring, he'd be able to show them off. He sighed as he went to the web site for a new lingerie shop he found, where he downloaded and saved every single picture, stopping only to purchase a pink teddy for himself. It had fluffy white trim, and it just looked so cute that he needed to have it.

Now he went to another web site, where the sold prom dresses. He downloaded, sorted and saved every single picture from there as well. He felt so good looking at all of those pretty pictures. The girls in them were so lucky; it was easy for them to look pretty. If only he could look that pretty himself. He considered buying himself a sparkly prom dress, but decided that he needed to lose some more weight first.

* * *

"Next" said the woman.

Jeff put down the copy of Vogue, stood up, and smoothed out the front of his shirt. His outfit was rather androgynous, and only an expert would know that he was actually wearing women's pants. It excited him to think that he was in public, wearing women's clothes, and nobody even knew it but him. He followed the woman to the chair, and sat down.

"My, your hair is a mess!" she said. "Its so long and shaggy. How would you like it cut today?"

Jeff handed her a photo, from a picture he had downloaded. The woman in the photo had platinum blonde hair with bangs hanging straight across, just above her eyebrows. Her hair was short, but full. The sides framed her face, and curled in a little bit at the bottom.

"I would like this haircut, please" he said.

"Are you sure?" asked the woman, not understanding why a man would want his hair done that way."

"Yes. Just like hers" said Jeff.

"Okay" she replied, shrugging her shoulders. It wasn't her place to tell him how he should style his hair. If he preferred a very feminine style, who was she to say no? A customer was a customer. And so she got down to work.

An hour later, Jeff's hair looked just like the woman in the picture. He went over to the nail counter, and told them he wanted a full manicure and pedicure. They were glad to oblige, filing and trimming his nails, before painted them in the playful pink color that he picked out. There was a spring in his step as he left the salon, looking more feminine than he ever had in all his life.

* * *

Almost six months to the day after his new haircut, Jeff finally got back the paperwork for his new legal name: Connie. There wouldn't be any more confusion with people calling out the name "Jeff", and having someone looking so feminine responding. He was Connie now, legally. He was so happy as he went to get a new driver's license picture taken, using his new name.

Back home, Connie celebrated by using his latest dildo on himself, while he imagined that he had a *pussy* to put it in. Of late, he had been obsession over pictures of pussies. He was especially fond of close-ups. He imagined what it would be like to have one for himself.

"Oh, I wish I was a girl!" he said out loud, as he looked at one particularly gorgeous woman with her legs spread wide open. He had realized his own need to have a pussy. And he wished with all his heart that he was a girl. Suddenly, he felt something inside that made him very sad: Audrey. He suddenly realized how terrible he had been, and what he had done to her. He was so filled with regret that he started to cry, ruining his makeup.

All night Connie couldn't get her out of his mind, as he thought about what he had done to her, and how he must have hurt her. Now that he felt like a woman on the inside, he had empathy for her, and realized what she had gone through. And that was when it hit him: he realized *why* he wanted to be a woman. Audrey. Ever since he had lost her, he had wanted her back in his life. Now he was trying to *become* her. His mind reeled as he realized that he wanted to *be* Audrey. In his heart of hearts, that was what he wished for, more than anything.

He called her up, and asked her if she'd be willing to come over and talk to him. She had moved on with her life, and had completely shut him out from her heart. They *had* been friends for a long time, so she agreed to come for a visit the next day. She had no idea what Connie had done to himself since she left. She was going to be in for quite a shock!

* * *

Audrey knocked on the door to the apartment she had been in many times before. But that seemed like a long time ago, almost as if it had been someone else, or another life. She waited, then watched the door swing open.

"Oh, I'm sorry. I have the wrong apartment" she said, upon seeing the blonde woman who opened the door.

"No Audrey, you have the right one" said Connie, as she waved for her to enter.

"Jeff?" said Audrey, her voice barely a whisper.

"It's Connie now" he replied. "I've gone through a few... changes."

Audrey came in. She was stunned to say the least, and she asked for a drink. As she sat on the new couch, she marveled at how the place had been redecorated. There were plants now, and colorful art posters. Gone was the sports memorabilia, replaced with furnishings showing a more highly refined taste.

She was amazed that her ex-boyfriend looked so much like a woman now! He walked like a girl. He talked like one. He sat like one, and acted like one in every way.

"I have to tell you" said Connie, "I came to realize that I made the biggest mistake in my life. Words can't express how sorry I am for what I did to you, and how awful it was for me to have treated you like that. I'm not asking for your forgiveness; I don't deserve it. I just want you to know how sorry I am, and that I'll regret it forever. Since I lost you, I came to realize that I missed you so much, that I wanted to *be* you. You are my inspiration. I want to live my life as you would live yours. I want to be just like you."

It was a lot for Audrey to take in all at once! She talked with Connie, and it took many hours for him to tell her everything. How he lost Loretta. How he started to become a girl. And how he planned on getting an operation so that he could really *be* a woman.

"I asked you here today, because I need a friend. I need someone to help me as I transition fully to womanhood. I know its a lot to ask, but I was hoping that you could be my friend, and support me."

Audrey had a small tear in her eye.

"Of course Connie. I'll do anything you need to help you."

Now Connie's eyes started to tear up. But for the first time since he had broken up with Audrey, he felt something inside: pure happiness. It was like a weight was lifted from his shoulders. He felt joy again! He was going to become a woman, and Audrey was going to be there to support him! Audrey came over and gave him a hug. They were girlfriends now, and forever.

* * *

Far above the world, floating on a cloud, Goddess smiled. Audrey had found peace and happiness. Connie had seen the light, and was well on her way to becoming a woman. And Loretta had a new lover as well. All three were happy now. Where there had been sorrow and hurt, now there was only happiness an love. There was one less male in the world to cause grief and pain, replaced by a feminine soul who would only think of others, share of herself, and keep the world at harmony and peace.

  

  

  

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