Kevin was a relatively simple guy. He sat down at his desk, reading various e-mails regarding issues with computers. The job was boring, and he really hated it but the information technology department paid well, and he was always rather gifted with computers. Still, tonight was a special kind of night for Kevin. There was a party after work and he and his fiancée Sarah had agreed to go. While it might seem like a silly reason to get excited, Sarah had agreed to let Kevin dress them for the occasion. Perhaps we should back up a little bit.

Ever since Kevin hit puberty, nothing felt right about him. He found himself at the mall, sitting in the food court and people watching. Others would people watch for various reasons but Kevin specifically would hone in on the women in their mid-twenties. Of course, he would look at their respective attractiveness but he was more interested in their clothing and shoes. Kevin always found men’s clothing boring and unappealing while women’s clothing was creative, sexy, and vibrant. There were so many styles and cuts, from various tops down to their shoes. Through puberty, Kevin found himself on the short end of the growth scale. At twelve, he stood five feet tall but when he graduated high school, he was among the shortest of his class, standing a mere five feet five inches.

While he was in college, Kevin had attended a party off campus where the theme was crossdressing. Men would don dresses and skirts while the women wore suits and dress shirts. Generally, Kevin was the kind to avoid parties but he was inspired. This party would give him a reason to go shopping for women’s clothes. Even at twenty years of age his body had never matured all that much, giving him a very androgynous body type. Just to make sure he wasn’t spotted, Kevin had gone to another city to shop. That night, he walked into the party wearing a wig, a red dress and black heels. His breasts were water balloons and worked well enough. He had worked hard on his makeup as well and during the party, was truly mistaken for a girl on two different occasions. Ever since then, Kevin was hooked on crossdressing.

Fast forward to four months ago. Sarah was out with her friends for the night so Kevin thought it would be a great opportunity to play dress up for a little while. They had been together for four years and Kevin knew that she would usually stay out until two in the morning or so. Being as it was eleven, he knew he had time. Opting for a more intimate outfit, Kevin had himself dolled up with red lipstick, and a lingerie set with garters. He had walked to the mirror, which was in the corner of the room. The clicking of his heels on the floor as he walked was one of his favorite parts of dressing this way. Kevin was so busy looking at himself and getting lost inside his own mind, he didn’t hear the front door open. When the bedroom door opened, he heard a gasp and turned to face Sarah, who was speechless. “Kevin?! What on earth…”

He didn’t know what to do. Here he was, standing with his male parts tucked between his legs. His mouth opened and closed several times before he came clean and told her about his secret fetish. Sarah didn’t say much that night, choosing to spend the night with a friend. Kevin was certain he had just lost her. The next day however, Sarah returned to the house and had a long talk with him. For weeks the subject was not brought up again. It wasn’t until they were eating breakfast together on a Saturday morning that Sarah asked him how many outfits he had. “I have a total of four outfits. The lingerie, a red dress, a summer outfit consisting of jean shorts and a halter top, and a more professional outfit with nylon stocking, a black skirt and a pastel pink blouse.”

“Can you wear one of them for me?”

Kevin was shocked, but if Sarah wanted to see him wear them, he wasn’t going to complain or argue. She wanted Kevin to go all out with makeup and hair and wear the blouse, skirt, and stockings. He did as she asked and an hour later, emerged out of the bedroom. Rather than water balloons, Kevin had paid for breast forms several years ago in a C-cup, and was wearing them. Sarah studied him for several seconds which felt like an hour to him. “It’s really kind of amazing. You do really look like a woman. Okay Kevin, I’m going to try something. I want us to go out today like girlfriends. I trust you have a female voice?”

Kevin cleared his throat and spoke in a soft, higher pitched voice. “Yes, I’ve used it from time to time. Sometimes when I’m stuck at the call center at work alone, I’ll use it when people outside the company call.”

“What do you call yourself?”

“Katrina. I accidentally used it one time on an intercompany call and people thought we had hired someone new.”

“Well then Katrina, give me a few to get ready and we will head out.”

Kevin was in shock. Not only was he dressed as a woman in front of his fiancée, but she was wanting them to go out, in public, in broad daylight? When Sarah returned to the living room she grabbed her purse and walked toward the door. It wasn’t a long drive into town, only six miles or so, but to Kevin, the trip felt more like a cross country haul. His eyes darted back and forth, wondering if anyone would recognize him. He flipped the mirror open on the visor and examined his makeup. Was there enough? Did he miss any spots when he shaved? It was a wonder Kevin survived the trip. By the time they parked, he had put himself into a manic state of mind. Sarah turned the car off and looked at him. “So here’s the deal. If you enjoy this so much, dressing up like a girl I mean, I want to see it in action.”

Kevin cleared his throat multiple times as a frog seemed to have a stranglehold on his vocal chords. “But I’ve never actually gone out in public like this. It’s always just been something I did at home.”

Smiling, Sarah shrugged and checked her hair in the rearview mirror. “This is your dream though right? To be a woman?”

“No! Well, I mean, not… really? I never really thought about bringing myself out in public like this.”
“You didn’t really answer my question.”

Kevin sat there with his hands in his lap, looking down at his fingernails, which were painted pink. It wasn’t that easy of an answer but Kevin couldn’t articulate it. It wasn’t that he wasn’t happy with Sarah. In fact, it was quite the opposite. Sarah had been the best thing that had happened to him. At the same time, dressing up in such soft clothing gave him a completely different kind of thrill, one that Sarah couldn’t give him. He conveyed this to her, but her reaction was very stoic. “I see. Well then, let’s go. Remember, we are going out as friends only. No holding hands or kissing. I work in this area and I don’t want any crazy rumors to start.”

Kevin nodded and the two spent the day not as future spouses, but as two friends out for a casual Saturday afternoon. Kevin followed Sarah into a coffee shop. He was certain that everyone was staring at him as they stepped to the counter and Sarah gave her order. The cashier looked square at Kevin and said, “and what can I get started for you miss?”

Kevin’s heart skipped a beat. The lady hadn’t even batted an eye in calling him miss. He felt his shoulders relax and gave the cashier his order. When the lady asked for a name he told her Katrina and they both stepped to the side to wait for their coffee. With the monkey off his back so to speak, Kevin really started to feel more comfortable. He even garnered a few looks from other men. While he wasn’t attracted to men, the fact that another guy thought he was good enough to take a second look at did excite him. They went to the mall together to window shop and Kevin, who had spent years paying attention to different kinds of women’s fashion, surprised Sarah with how much knowledge he had. By the end of the trip, Sarah had bought two new outfits solely on Kevin’s expertise.

After several hours, they walked back to the car. Kevin had gotten to the point where he was even walking with a subtle sway in his hips. The car ride home didn’t seem nearly as long this time as they talked all the way just as they had during the outing. Walking through the front door, Sarah dropped her purse on the table along with the outfits. “You really amazed me you know that? I didn’t expect you to carry yourself so well.”

Kevin smiled. “I was really surprised too. I figured it would be much more difficult.”

Tilting her head, Sarah moved to the kitchen to get something to drink. “We are home now Kevin, you don’t need to talk in that voice anymore.”

That comment brought Kevin back down to earth. He apologized and went to the bedroom, taking off the clothing, makeup, and nail polish. As he stared at his clothing and wig, Kevin felt a swell of pride, knowing that he was able to pull it off and Sarah seemed pretty impressed as well. Maybe divulging his secret to her wasn’t such a bad thing after all!

Back to the present day, where Kevin was answering e-mails and staring at the clock, waiting for the work day to end. Tonight was a costume party in the city. The theme was ‘Pimp and Ho’ and tonight, Sarah would dress as the pimp, while Kevin would get to be the ho. The hours drug by and Kevin had finished his normal work already so he spent the rest of the day surfing the internet.

One of his favorite artists was a woman who went by the name of Phoenix. She didn’t do much in the way of crossdressing art, however she had a sense of style and flair in her artwork while her stories, though not really his cup of tea, were written in a way that he really enjoyed reading. Granted, most of her stories were completely off the wall and unrealistic. Men being turned into hugely pregnant women, women turning into dogs and horses, even a series of stories about her ‘family’ where all kinds of strange transformations occurred. Her online persona wasn’t exempt from odd changes either. Regularly, she would make art of herself with fox ears and a tail, or pawed feet. Really, there didn’t seem to be a form she wouldn’t try out. Kevin sighed, thinking about what it would be like to actually be able to transform himself as easily as she did in her artwork and stories.

When work ended, Kevin hurried home, picking up some fast food for Sarah and himself on the way. It was going to take him a long time to get ready for this event. To pull off the look, he was going to be wearing platform heels, an item that he didn’t dare ever try to walk in. Kevin got home before Sarah and immediately put the platform heels on to try and get used to them. Sarah opened the door right as Kevin took a step, and laughed when she saw him trip and fall onto the couch. “Not as easy as it looks, right?”

Kevin chuckled. “I never said it was easy. I don’t know how you wear things like this. The only pair of heels I ever wore were only two inches. These are like six! It feels like I’m on stilts almost.”

With a giggle, Sarah sat down at the table to eat quickly. Kevin joined her as soon as he was able which, given the shoes he was wearing, was a full minute later even though he only had to walk forty feet. “So Kevin, you really want to go through with this tonight? I mean, I totally understand if you want to back out.”

Kevin frowned and shook his head. “No way! We worked too hard on outfits to just bag it the day of the event. I can totally walk in these, once I get the balance correct.”

“Okay but if you want, we can swap the roles to more, conventional ones, if you like. Just let me know.”

Sarah hurried through her meal, only picking out parts of the wrap he had gotten her and disappeared into the bathroom. It was nice of her to offer that, but these shoes weren’t going to stop him from dressing up! He got up and continued to walk around, becoming more and more comfortable walking in them as time passed. Checking the clock, Kevin moved to the bedroom and began getting himself ready.

Sarah tapped her foot as she waited in the living room. She had a baby blue suit on with matching slacks, a hat with a feather and a cane. “Come on Kevin! Just because you are dressing like a woman doesn’t mean you have to make us late! We need to…”

Her sentence trailed off as Kevin emerged from the bedroom. He had gone all out this time, buying new and larger breast forms in a DD-cup. His wig was done up in blonde pigtails while glossy pink lipstick covered his lips. Rather than a conservative outfit, Kevin had gotten a gold top with a heart cut out in the center of the chest. The top gave way to a black belt and a leopard print skirt. Fishnet stockings ran from his mid-thigh to his toes and the black platform heels completed the outfit. Sarah was dumbfounded. “How is it that you can look better as a woman than most women can? It’s just crazy to me.”

Kevin blushed and walked toward her. With the heels, he was several inches taller than Sarah whereas normally he was a few inches shorter. “I don’t know really, but thank you for the compliment!”

His voice was a little deeper than his normal female voice. Sarah could tell he was going for a more sultry sounding voice. They headed out and into town. When they arrived, Kevin, who went by the name of Kat for the night, drew a great amount of attention. Kevin fell in his role as a ho easily while Sarah walked around with him. Over the course of the night, and several alcoholic drinks, Kevin had really gotten into the role, even dancing which he would never usually do. Sarah’s eyes kept moving from side to side, seeing how everyone seemed to looking at him, and not as all at her. “Kat, I’m going to go outside for a bit. You want to join me?”

Kevin saw her lips moving but the music was so loud, he really couldn’t hear anything she had said. Nodding his head, Sarah turned to walk outside but Kevin stayed on the dance floor. The moment sarah left, he was swarmed by other people all dancing around him. Sarah turned back and saw this. Fuming, she stomped out of the party and to the car, where she sat for several minutes, staring at herself in the rearview mirror. She grabbed a piece of paper and a pen, and began writing.

Back in the party, Kevin was oblivious to the fact that Sarah was no longer there. The fact that everyone at the party thought he was a woman, combined with the outfit he was wearing, had put him into a blissful state in his mind. This was even better than the day he spent out in public as a woman! The deejay took a break and the dance floor emptied, with everyone going to the bar. When Kevin got there, the bartender slipped him a note. “From the pimp you came with sweetie.”

With a bit of panic, Kevin looked around the party but didn’t see the baby blue suit anywhere. He opened the letter and began to read.

Dear ‘Kat,’

You and I have been together for over four years and have gone through our share of toils and troubles. No matter what, I always was able to get through anything because I knew that you were the ‘man’ I loved. That said, I can’t do this anymore. I don't want to be in a relationship with one of my girlfriends and honestly, the only time you seem happy is when you are in drag. I need a man who is comfortable being a man and, I’m sorry, but you aren’t that man. I left money with the bartender for cab fare so you can get home. By the time you read this, I’ll be at home packing my things. I hope you can find happiness in life.

Sarah

It felt like a stone was dropped into the pit of his stomach. She had seemed to be okay with the occasional crossdressing. Hell, she had even suggested that they go to this party in drag! No longer interested in the party, Kevin gathered his things and left. He didn’t really know what to do or where to go. Part of him wanted to rush home, tell Sarah how sorry he was and promise to never cross-dress again. Something she said in her note though stuck in his head. Was he really only truly happy when dressed as a woman? Kevin walked slowly down the street as he lost himself in his own thoughts.

The lack of direction in his walking took Kevin around parts of the city he had never really explored before. After several turns, he didn’t recognize where he was at all. The area was dimly lit and had an ominous vibe to it. Feeling a bit vulnerable, Kevin saw a small shop across the street. The place had their lights on and seemed to be the only place open. Something drew him to the small shop. Perhaps it was the fact that it was open? Maybe it was because he could see a few really cute outfits in the window? Or maybe it was the pair of fox ears, visible on the window that reminded him of the artist he followed online. There was a sound behind Kevin that startled him and he wasted no more time, crossing the street and opening the door to the shop.

For how small the shop looked from the street, the shop itself was very spacious. There were aisles of clothing ranging from kids wear all the way up to outfits that were so large, an entire family of people could fit inside! Kevin continued walking around, finding an area with jewelry of all different kinds ranging from rings to collars. He was so entranced by the jewels he didn’t hear someone come up behind him. “Welcome to my little shop darlin,’ how can I help you tonight?”

Kevin’s heart leapt into his throat. The voice was feminine but a bit deep in tone. Kevin turned slowly and nearly fainted. Standing in front of him was a woman with foxlike ears and a tail. She was tall, with fire red hair and violet eyes. She smiled, revealing two canine teeth. “How nice it is to meet you. My name is Phoenix.”

Kevin’s eyes rolled into the back of his head and everything went black as Kevin fainted.