Paint Work


An eager young salesman looks to a fraternal organization to help him make the connections he needs to get ahead. Originally a contest entry, the object of the contest was to use the line "We are very disappointed in your progress" at least once in a small 30K story.

Paint Work

by Joe Six-Pack

Darren Kennedy had arrived home late that night, weary and worn. Not from working, but from anxiety. He was as skittish as a lost kitten, constantly on his toes and ready for anything. At any time, in any place, his world could have been turned upside-down.

Was he going to run from this danger? No. Was he going to hide from this threat? No. Not at all. He wanted it. He wanted it more than anything. His suspense was in the waiting. He wanted to know. He just wanted to be told. What was it they wanted him to do? And how fast he could do it?

The 'Grand Knights of the Royal Order of Ur', were a secret society with power and connections what most people dared even suspect. Known as 'The Magistratus' to those who had heard of them, the super-secretive guild had tendrils that reached into the highest positions of power and influence in the western world. Founded in the middle ages, its' orchestration of history accounted for the founding of the great civilizations of our time.

Well, at least that's what the brochure said. A very impressive brochure. A four-color job with pictures. Glossy paper. Ooo.

Darren had been handed an invitation to join by an old college friend, Ritchie Land, who he hadn't seen in years. It was the responsibility of every member to induct another, and previous attempts by Ritchie were unsuccessful. Darren was apparently a last resort. But that didn't bug Darren at all. This was a potential turning point in his life. It was perfect for him. Because he was a hand-shaker, a networker, a social predator.

He was in insurance.

His business depended on knowing people, getting references and recommendations. That's how he sold his policies. Cold sales calls were for suckers. What you needed was an "in" with potential clients. So, The Magistratus was a dream come true.

He had been staying up nights, dizzy with anticipation, knowing that the connections he could get from joining the society would put him on easy street. He had made it. He was with the big boys now.

The induction ceremonies were dull, slow and procedural. A lot of candles, some robes and a little speaking in tongues. It was a lot of show. All Darren had to do was stand and recite a few lines. But what he didn't expect was that the ceremony was only the first part of induction into The Order. There was a trial. A "trial of brotherhood" it was called.

Whenever a member of The Order was asked to help another, it was mandatory. You had to obey. It was the way of The Magistratus. Brotherhood above all else. Above family, above country, above business. The brotherhood was only second to God.

So the trial was the final test for Darren. He was to receive instructions from The Order. They would come at any time, he figured, and probably when he least expected it. Which is why he was a nervous wreck. He wanted to get this over with. He wanted to get on with his new, ultra-successful life. When would he know his task? When, when, when?

It had been three days now. He knew he was going to be kept in the dark, but this was driving him nuts! He was pacing his apartment, pacing like mad around his little living room, mumbling to himself. He hadn't even bothered changing out of his suit. And he was sweating right through it.

Suddenly, the sound of his ringing phone ripped through the room, shocking Darren out of his tense, claustrophobic world of anxiety.

He approached the phone tentatively. Was he scared? No! "Hello!?" He shouted boldly into the receiver. There was no answer. "Hello!!?" He shouted again. A near-silent static was all that he could hear at the other end.

Could he hear breathing? Was someone there? A deep, gravely voice spoke. "We are very disappointed in your progress."

"What!? What do you mean?" Darren said. "Is this the The Order? Hello?"

'Click' went the phone. The line was dead.

"Hello!?" Darren fruitlessly shouted again. "Hello?"

Progress? How could he have made progress? They hadn't even told him what to do! But maybe it wasn't The Order. Maybe it was a wrong number. No! Don't be stupid! Of course it was The Order! But he didn't know what it meant. What was going on?

He decided to call Ritchie. He would help. He dialed the number but stopped. It was forbidden. No contact during the trial with The Order and its' members. It was a strict rule of this 'trial of brotherhood.' You will not contact them. Failure to comply would result in dissolution. At last that's what he remembered. That made sense, didn't it? It sounded right at least. He could be wrong.

What did they want him to do? He was supposed to wait for instructions, right? Wasn't that in the brochure? Hadn't someone told him that? Maybe he was supposed to go back to the hall or something.

A knock came at the door. Darren froze. Was it them? Of course it was! Should he answer? The knock came again. He ran to the door. No. He shouldn't answer. Yes he should. They were contacting him! He need to answer. No. Yes! No.

What to do? He had to do something! He undid his latches and locks, and peeked out the door as he cracked it open. There was no one there. He swung the door open wide, and looked down the hall. One way, and then the other. The hall was bare. Only the painters' cans from the ongoing renovation seemed out of place. Otherwise, it was totally vacant.

As he stepped forward, he kicked something. A small box. A small, unmarked brown box. It was from The Order! Probably!

Finally - a clue. He took it inside. What was it? What!? Should he open it? Maybe it was a trick. He hadn't received instructions to open it. Maybe they would kick him out if he tried to. Oh, God, he was killing himself with second-guessing. He grabbed a knife and ripped open the taped seal. He carefully removed the tissues inside and saw the contents of the box.

One pair of red high heel shoes.

Now what in the wide world of heaven and earth did that mean!? Women's shoes!? He checked the box again for anything. Anything at all that would clue him in. Just a little scrap of information was all he wanted. Darren actually found himself pulling out the hair on his head, he was so anguished.

What did the guy on the phone say? "We are very disappointed in your progress." That was his only clue. Then it struck him. This was an initiation. That was they key word: initiation. Like a fraternity. When he was in college, he remembered stories about guys who had to dress up like girls for a frat initiation. But that wasn't what this was about, was it? No. Couldn't be. But the evidence was right there. Women's shoes and the instructions. "We are very disappointed in your progress." That's what it must have meant. The progress of dressing like a woman. That was his task. His trial. He had the instructions. He now had to act.


It wasn't worth losing his job over, so he had called in to the office sick - maybe for a little while. He then spent the night ordering up clothes. A wig. A tube of lipstick. It was all overnighted to his apartment.

The next morning, he waited anxiously for the deliveries to arrive. He was perched in front of his door, ready to answer a quickly as possible, hoping that no one would see the embarrassing items. He heard a knock. But it wasn't his door. It was the apartment next to his.

He poked his head out of his door to check. "Hey." Darren whispered to the delivery man.

"Excuse me Sir! Are you talking to me, Sir!?" The brash delivery guy said.

Just his luck. "Yes." He tried to say quietly. "Are those packages for apartment 23-B?"

"Maryanne's Boutique!? Are you sure? These are for apartment 23-B!" The guy checked the door for the address. But they had removed the numbers for the painting. "They look like women's clothes, Sir!" Darren wanted to sock this guy. "Are you D. G. Kennedy? Apartment 23-B!?"

Darren tried as best he could to yell and still keep quiet. "YES!" He squelched.

"I see." The delivery guy rolled his tongue around in his mouth. "Sign here sir."

Darren grabbed the electronic pad and scribbled in something that looked not unlike his signature. The delivery man let out a deliberate cough. Darren threw the pad at him and slammed the door shut.

Opening his package, he sifted through the unfamiliar items and organized them. He slapped the lipstick on, crammed his feet into the shoes, stuffed some socks into his shirt and pulled on the wig. He stumbled around his apartment, and then yanked the giant floral print dress over his head. It was now or never. He couldn't chicken out. He'd walk around the building once or twice, and then get back into his apartment. Just enough so he'd bee seen. Darren headed for the freight elevator.

He walked around the block once, nervously, and staggered around like a drunken crane. He just kept his gaze straight ahead, and made no eye contact. It was a big city. These people had seen stranger, and didn't give him any trouble. He then skittered back into the rear delivery entrance of his building. At least he hadn't seen anybody he recognized.

Darren dropped himself on the couch and let out his breath. He was hyperventilating like a long-distance runner. Then the phone rang.

"We are very disappointed in your progress." The voice said.

What!? "Hello!" He cried into the phone. It was already dead.

Darren shook the receiver angrily. Wasn't that good enough!? He dropped the handset back in place and then made his way to the mirror. Then it became obvious. He looked like a joke. Pantyhose bunched around the ankles, lipstick scribbled on his face, his fake breasts were cockeyed. That was the problem. He wasn't fooling anyone, and had no idea what he was doing. He needed professionals.


Darren was pleased with the results. Looking in the mirror, he could still kind of see himself in its' reflection. But the edges were softened, the flaws covered. He looked not altogether completely masculine. The make up was a bit gaudy, and his strong features were still very much in evidence. And he did look a bit like a drag queen.

But that's kind of what he expected, when he made the appointment at "Makeovers by Violetta" down in the gay district. He had blown a few hundred bucks and gotten the whole treatment. His brows were tweezed, his ears pierced, and he had invested in a new, far more convincing wig. Now he looked like a vegas showgirl crossbred with a construction worker, but it was about what he had expected. And worth every dollar, he suspected.

Darren strode down the street, taking it slowly on the heels, as he walked up and down the sidewalk in front of his apartment. Onlookers might have assumed a touring production of La Cage aux Folles was in town, with the sparkling red gown he wore. He had long chandelier earrings and ostentatious costume jewelry. He even had his nails done in red and one inch long. It was outrageous, but Darren didn't much care. Just as long as The Magistratus saw.

After giving it twenty minutes, he thought he had gotten the point across. Then, from his rhinestone-riddled purse, his cell phone rang. His wig fell halfway off his head, he was so surprised.

"Yello?" He said into the phone.

"We are very disappointed in your progress." The gravely voice croaked.

"Damn it!" He bellowed to the pedestrians nearby. "What do they want from me!?" He had to hold himself back from smashing the phone onto the pavement.

Everyone looked at him. Then he had a clue. Voice. He still sounded like a man.


"Hellooo?" He sang. "Kennedy residence, how may I help you?" The voice was tender, soft and smooth. Darren had practiced it for three days straight. He found some courses on 'speaking with a feminine voice' on the internet and crammed in the time to study. He continued to hum, getting his vocal chords in shape.

"Hellooo?" He tried again. He had it just about perfect. Darren kept speaking, idly. He needed to keep practicing. "Hellooo, coffee mug." He said. "Hellooo shoes." Darren was still wearing the pumps. He figured that at any time he might be checked on that, so he had them on all day. He was actually quite nimble in them now.

Finally, the phone rang. "Hellooo? Kennedy residence." Darren said. Perfect. He figured that this was the trick. When he answered the phone, they didn't like the way his voice sounded. Now that he had the dress, the look and the voice, how could he not be everything they wanted?

"We are very disappointed in your progress," the voice said. "Click," the line went.

Darren was wild with anger.


Darren knew he had it straight now. There was still one flaw in his disguise. He knew for sure this time he had the problem licked. For a while there, he felt it all slipping away. All the success. All the money. All the power. But now that he had figured things out, he was in like Flynn. Whatever that meant.

No wonder he wasn't making 'progress' fast enough. He was a load. Darren was about five-foot nine, but he weighted almost 155 pounds. Not fat for a man, but for a woman? That was too much. Way too much. He couldn't even wear a real dress at that size. Every outfit he had ordered over the past two weeks was plus-sized, to hide his manly proportions. But if he was going to get into a real dress and look like a real woman, he had to lose weight fast.

He had started with simple workouts. Not fast enough. He then graduated to weight-loss supplements and severe celebrity diets. Still not fast enough. He then opted for a little liposuction. Not a lot, but enough to get his waist down to size. He had been wanting to drop a few pounds anyway. And as a result of all his efforts, he had now dropped to a svelte 115.

In addition, he had to wear a compressive garment after surgery. It would be there for a couple weeks. They had two types, male and female, so of course he took the female. And it was exactly what he wanted. His waist was down to twenty two inches, and the doctor said it would get even slimmer after the swelling was gone. And maybe it was him, but his butt and hips seemed larger, as the garment squoze his fat down into his rear. Perfect. It looked extremely feminine. The whole procedure was expensive, but it was certainly worth it to make progress with The Order.

As he exited in front of his building, Darren was dressed in his new, shapely brandy-colored peplum skirt set, which showcased his new slim figure. Someone from The Order had better been watching, because he looked good. He had spent the whole afternoon doing errands, making sure that whoever was supposed to see him, saw him.

He hadn't been idle with his recovery time, either. He had set up a new bank account and credit card under the name 'Kimberly Kennedy' and had even acquired a fake I.D. under the name. Just in case he was supposed to do that. He wasn't going to take chances. There was no way he was going to get caught with his pants down. Or actually, with his pants on - as it were.

Darren clomped down the street and hailed a taxi. When one wouldn't stop, he leapt out into traffic and waved his arms wildly in the air. Finally, one screeched to a stop. He tried to get in the car, but found that the tight, long skirt kept his from maneuvering well. He wound up having to hoist himself up, holding onto the car roof and twisting his bound legs into the car. He landed on his side, and his curly wig fell off his head. He quickly shoved it back on and sat upright, slamming the door behind him.

Then his cell phone rang. "We are very disappointed in your progress."


Dreams of his future became living nightmares. Darren could see it in his mind - the success he had worked so hard for was flittering away. The Magistratus weren't satisfied. He could see them. He really could. They were dark, shadowy figures trailing him wherever he went. Looking on from the alleyways. Hiding just out of sight. They were whispering. Disappointed. Shaking their heads. And still, he hadn't been able to figure out what they wanted. What was it they wanted?

But then he remembered what had happened when he had received the last call. It was when he was trying to get into the cab, looking like a fool. That was the holdup. He wasn't acting like a woman. That must be it. He was still his clumsy, ungainly self. He sounded like a woman, and had the shape and clothing of a woman, but he hadn't acted like one.

So he did a little research and found Dr. Paige Carslyle, a psychologist who specialized in helping transgendered men 'transition' into being women. But more important to Darren, she also specialized in hypnotherapy.

It had taken more money than he wanted to spend, but finally the doctor capitulated to using both talents on Darren. It takes a lot of cash to buy off someone's professional integrity these days. How long could he keep throwing money at this problem? It was going to have to pay off big.

But two weeks of two-a-day hypnotherapy sessions had done the trick. Darren was energized by the things he could see change in himself. The way he walked, they way he talked. They way he sat and the way he used his hands. He would glimpse himself in the mirror, and just by the look on his face it seemed like he was a different person. Gone was his expressionless facade. Instead, his smiling lips and open eyes were bright and welcoming. He kept his head held high. He stood up straight. He glided when he walked. It was all left the unmistakable impression of femininity, and now he could feel it all coming together for him now.

"Thank you, oh thank you so much, Paige." Darren gushed.

The doctor was all smiles. She really had out done herself this time. The change was remarkable. "Kimberly, please. It takes a lot of commitment to come this far this fast. You should thank yourself." She said.

Darren had to come up with a story to tell the doctor, because he couldn't tell anyone about The Order. It was forbidden. So instead, he constructed a lie around his "long suppressed" need to bring out "the woman inside." The first time he told this fairy tale to the doctor, he nearly broke out laughing. Fortunately, he made it look like his tears of laughter were of pain. The pain of never being able to be "the real me." It still made him smirk when he thought about it.

Darren had his hand against his chest, and tossed his other hand limply, waving off the credit given to him by the doctor. "I couldn't have done it without you, Paige. You've been absolutely wonderful through the whole process. It's been delightful. I can't thank you enough." He shook his hair out of his face. He had grown tired of the wig falling off his head, and had his natural hair done up properly. His brown hair was lengthened with extensions, now about shoulder-length, and styled straight with flimsy bangs over his eyes. And his beard wasn't the slightest bit visible. He figured that his new regimen of shaving twice a day had started to kill the hair follicles or something. That happens, right?

"Now before you go, I want to make sure that you're still taking the pills, and promise me that you'll come and see me every few weeks just so we can chat and catch up." The doctor said.

"Oh, please, Paige. You'll never get rid of me!" Darren giggled. "But I thought the pills were just for these sessions."

The doctor shook her head. "No, no. Kimberly, you've got to take keeping those pills. All of my patients in transition have to take the pills."

That didn't make a lot of sense to Darren. The pills were to relax him for the hypnotherapy, weren't they? What else would they be for? "For how long, Paige?"

"Well, I'll tell you what. You go and see Dr. Thompson next door." The doctor gave Darren a card. "He can give you some subdermal implants that will last you the rest of the year."

That sounded good to Darren. He'd go right away. "That's very nice of you, Paige. I so appreciate everything."

After seeing Dr. Thompson and getting the subdermal implants, Darren decided to pick up a new outfit to celebrate his completion of therapy. He was curious to see what he'd select now that he had the so-called 'mind of a woman.' He was very disappointed to find that he had been attracted to the same sort of clothes he would have selected anyway.

He wore it out of the store, a red sheath dress that fell a couple of inches above the knee, with his ever-present red pumps. He was a little surprised to find that the size 10 was now a little loose on him, but he was still too big for an eight. He'd need to work out more. Darren also had gotten a smart little purse and some bracelets, a necklace and a cute broach.

He had used his 'Kimberly Kennedy' credit card to pay for it all, and it was just as well, as he'd misplaced most of his 'Darren' cards anyway. They were probably still in his wallet. Which was in his pants. Wherever those were.

As he toted his bags into the taxi - swinging his legs gracefully into the seat, he was pleased to note - he used the very feminine voice he had grown so accustomed to using. "Bridgewood Tower Apartments, please."

Then his cell phone rang. Maybe it was the girls down at the fitness club. Or it could have been Paige, or even Dee, his hairdresser. He removed his earring to answer the the phone.

"Hellooo?" He said, softly.

"We are very disappointed in your progress." The voice said.

"What!?" Darren screeched into the phone. "I've done everything possible!"

The dial tone was like a death sentence. Darren was furious. He stamped his heels on the floor of the taxi and shrieked in anger. He had worked so hard, he had done so much! He had done everything. Absolutely everything. Except for...

Wait a minute. That was the test. How far would he go? That's what the Magistratus wanted. They wanted so see what he was made of. Did he have the commitment? The commitment to give up everything to join the Grand Knights of the Royal Order of Ur?

"Okay. I've changed my mind." Darren told the driver. "Take me to the airport."


He had arrived in the rocky mountains without a single bag of luggage. Darren had looked it up, made a few calls and headed here straight away. It cost him a small fortune, but he'd prove that he was worthy to join The Order. This would clinch it.

Just about every cent he had ever saved was spent on it, but he kept telling himself that it would all pay off in the end, a hundred fold. Joining the Magistratus would solve any problems. Truly, he was convinced it would do even more than that. It would solve all of his problems. All of the problems he ever had. The Magistratus would save him. They would make him successful, wealthy, respected and feared. He would have everything he ever desired.

The appointment he had booked with the surgeon was for the works. Throat shaved, facial plastic surgery, breast implants and most importantly of all - vagioplasty. Sex reassignment surgery.

The doctor was reluctant to take a patient who had spent so little time in transition, but Darren convinced him with a check. He was the best doctor in the United States, a doctor known worldwide for his skills in this sort of operation. But not beyond taking a few dollars for a rush job. Within a couple of days, Darren found himself checking into the private clinic and signing consent forms. His life was now out of his hands.

But Darren wasn't worried in the slightest. He had seen the man who was on the plane with him. He saw that same man at the airport. He must have been with the Magistratus. Following him. That was it. He was being followed. The shadowy man was tracking him. He knew it. It had to be. They thought they could fool him? Ha! He could see through the smoke, see through the tricks. They thought they were testing him, but now he had the upper hand. He knew the plan.

They would have him go through with the doctor's appointment. He would get booked into the hospital. Then they would probably wheel him into surgery, and even put him under anesthetic. But Darren knew what was really happening. The Magistratus would let him go all the way to the point of no return, waiting for him to give in. But then when they saw his devotion to The Order, they would yank him back from the brink, and congratulate him for having the commitment to follow instructions. To give everything up for the sake of the Magistratus. He'd wake up and it would all be in his grasp. Money, power, influence and peace. Everything in his life was going to be okay from now on.


It took longer than she expected to complete the surgery, but now that she was home, she felt so relieved to have it over with. The surgery got complicated, because when she woke up after the vagioplasty, things got a little weird for Kimberly.

She bent down to pick up the mail that had been left at her doorstep over the past few weeks. It was all addressed to that poor excuse for a man who used to live here. Bent down like this, her white miniskirt would have given any onlooker a show, as would her tight fire red crop top.

Dumping the mail on the table, she didn't even have the energy to kick off her heels before she sank into the sofa. It had been a wild ride the past few days. After she had had the complete SRS, according to the doctor, she had gone a little crazy. She didn't remember it now, but it seemed that she had caused quite a fuss and had to be drugged and restrained. She was supposed to have been yelling like a maniac about some sort of fraternal order.

Fortunately, Paige was an absolute angel, and flew out to help her deal with it. A few hypnotherapy sessions later, and Kimberly was back to normal, reminding her about her lifelong desire to be a woman. What an absolute godsend Paige was. She was a little cross for Kimberly rushing into surgery so quickly, but she put that aside and helped her pull through.

Now, finally, she was Kimberly. All the hard work and money had paid off. She was now a beautiful young woman outside, like she'd always been inside. A long journey had come to an end. She'd have to thank Paige in some way for helping her realize that.

And it was now so good to be home. But tomorrow, she was going to clean this place up, that was for darn sure! What a mess. In fact, why not get started right now? Kimberly shook out her trash bins into a bag and headed out into the hall to dump them down the chute.

"Hi there!" A voice came from her left. It was the lady who lived next door to her. They had never spoken before.

"Oh, hi!" Kimberly said.

"I'm Janice." The lady said. "I don't think we've met, but I had to ask, where did you get those shoes?"

"These?" Kimberly said, showing them off. "They are nice."

"I used to have a pair just like them but you know, I sent them out for repairs a few months ago and they never came back."

Kimberly was at a loss. "That's a shame."

"Do you remember back when they were painting the hallway?" Janice asked. "Well, they took all the numbers off the doors and I think everybody got deliveries mixed up for a few days. I was wondering if maybe my shoes ahd been delivered to you by mistake..."

"I don't think so." Kimberly said. "I got these as a gift. I think. It's tough to remember." Then Kimberly heard her phone ring. "Oop! That's my phone. Nice to meet you, Janice. Would you like to get together for tea sometime?"

Janice smiled politely. "I'd love to. Just leave a message or come by."

"I will!" Kimberly finger-waved goodbye and caught her phone before the machine picked up. "Hellooo?" She said.

"We are very.. Uh.." The deep, gravely voice said. "We don't know what the hell's going on with you."

"Excuse me? Who is this? I think you have the wrong number." Kimberly said, upset.

The voice sounded a little tired. "Look, Darren. Since you never showed up back at the hall for instructions, it's over. I don't know what the problem is with you, but the most recent information we've received is... distressing. Just go on with your life, and whatever you're into. We didn't know you were such a freak. Forget about us."

"Hey!" Kimberly was downright pissed. "You listen to me, you arrogant jerk! I can't help what I am inside! We all have to be true to ourselves, and I'd like to think people could appreciate that!" She gathered a second wind. "We've got to get past these dumb prejudices, and take people for who they are, not just what we want them to be! It's people like you who make life so very difficult and painful for others! As a society, we should be helping, sharing and loving with those around us!! And if your attitude is any indication, I'm very disappointed in our progress."

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