But he didn’t mind taking the bus. He only ever used his car when he was going on dates. His job was conveniently located one block from the bus that picked him up one block from his house, and the grocery store was on the same bus route.
CHAPTER III
Ernie was at home when he heard his doorbell ring. By the time he got to the door, his visitor was gone, but there was a package on his doorstep. He brought the box inside and tried to remember if he’d ordered anything online. He couldn’t recall, though that was usually the case before opening a package.
He looked for the sender’s information but couldn’t find anything. He couldn’t even find his own address written on the box. Was the package hand delivered by the sender? Or was it sent by private courier? Before opening the box, Ernie went to the window to see if he could spot anyone walking down the street in the opposite direction. But there was no one there.
He returned to the box, now feeling a bit worried, though he wasn’t sure why he was feeling worried. He retrieved a knife from the kitchen and cut away the tape. Inside the box was a little beige dress, a pair of panties, a bra, a dark brown wig, a little pair of heels, and a small fabric bag full of makeup supplies. Ernie dug into the box to see if there was a note, but there was nothing. The box had obviously been delivered to the wrong address, but there was no return address anywhere to be found—no information at all about the sender.
Ernie checked the whole box again, hoping to find even a phone number so he could have the box returned to its rightful owner. But there was nothing. So he taped the box back up and put it in the front hall closet, so it would be close when the rightful owner came to pick it up.
It was the next day when Ernie found a letter in his mailbox, also with no information written on the envelope. He brought it to the kitchen and opened it up. It was addressed to him:
“Ernie, I’m sure you’re wondering why I sent you a box of women’s clothing. Well it’s really quite simple. I want you to wear it. Tonight, I want you to put the clothes on and step outside at exactly 11:00 PM. You don’t have to stay out for long—just walk to the sidewalk and back. If you check your e-mail inbox, you will see a pending e-transfer for the amount of $400.00. If you accept the money, then you accept your challenge. Oh, and please try to look your best. I’m looking forward to seeing you. Sincerely, M. Maker.”
Ernie had to read the letter a second time before he realized it was real. He pulled out his phone and checked his inbox. Sure enough, there was a pending e-transfer from an M. Maker for the amount of $400.00. But Ernie didn’t know anyone with the last name Maker. Who was this person and why did he want Ernie to put on the women’s clothing so badly?
Ernie was ready to throw the letter out along with the box of clothes, and then he remembered that his rent was due in two days, and he didn’t have the money. He’d tried reaching out to his wealthy parents, but they hadn’t picked up the phone, and they never leant him any money anyway. So he found himself staring at that box of clothes again. Out of curiosity, he pulled out the pair of shoes. He tried slipping one on his foot. The shoe fit perfectly—and the dress was in his size, too. How did this mysterious M. Maker get his shoe size and his dress size? Even Ernie didn’t know his own dress size—and why would he?
He shook his head, realizing he’d actually been considering the crazy proposition. He stuffed the dress and the shoes back into the box and he stuffed that box into the front hall closet. He needed money, but he wasn’t about to stoop to that level…
Though he found himself wondering if it would really be so bad. All he had to do was put on the dress and the wig and a bit of makeup and step outside for thirty seconds. He could be dressed and undressed within an hour—and four hundred bucks is a lot of money to make in a single hour—especially when you’re unemployed and behind on all of your bills.
Ernie found himself feeling frustrated. He had no way of reaching out to this M. Maker guy, to figure out why he was willing to pay so much for such a silly task. Maybe M. Maker would be hiding in the bushes with a camera. Maybe he would snap some photos and use them as blackmail. But who would want to blackmail Ernie? What had Ernie ever done to anyone?
Ernie immediately thought of his landlord. His landlord hated him. Whenever Ernie went to drop off a rent cheque, his landlord would remind him, “All of my other renters pay their rent on time.” But even if his landlord was frustrated with Ernie’s slow rent payments, why would he set up such an intricate and expensive blackmail? Four hundred dollars is a lot of money, and the clothes, wig, makeup, and shoes were probably worth a decent amount as well.
Then Ernie found himself thinking of his mechanic. He still owed his mechanic about four hundred… But why would his mechanic go through so much trouble? And how could his mechanic have gotten his shoe size? At least the landlord could have let himself into Ernie’s suite to find out Ernie’s shoe size…
And then there was William—the guy who set Ernie up to be fired. Though Ernie still wasn’t convinced that William had set him up. Ernie had heard rumours before that employees could demand raises and companies were obligated to give them. Besides, Ernie couldn’t think of anything he’d ever done to upset William—certainly not enough for William to go through so much trouble.
It was 10:00 PM when Ernie received an e-mail notifying him that his cell phone payment did not go through. “Please update your payment information or your service will be cancelled in four days,” the message read. Ernie felt sick to his stomach. He’d always wondered how people ended up homeless, living on the sidewalk, begging for small change. Now he was starting to understand. His heart started pounding as he looked back over at that front hall closet, where that box of clothes was hiding.
And he caved. He opened the box and he started getting himself ready. He slipped into his dress and then he got the wig onto his head. The wig had long bangs that hung over his eyes. It was a surprisingly realistic wig, maybe even made from real human hair. The dress was short, hardly covering his whole bum, but it wasn’t like he was wearing into town—he was just wearing it out to his sidewalk and back.
He thought the dress looked silly with his hairy legs, but he didn’t care enough to do anything about it. There was a pair of panties in the box, but he didn’t bother wearing them. He was able to scrunch his underwear up enough under the dress that they were invisible. For his makeup, he didn’t bother with half of the items in the bag. He just rolled a bit of mascara onto his eyelashes and then he did his best to draw thin lines around his eyes with the eyeliner. His work was sloppy, but he didn’t actually look too shabby. He actually looked kind of cute.
He did a few little poses in front the mirror before realizing it was 10:55 PM. He quickly went into his e-mail and accepted the money transfer. Then he found himself standing by his door, waiting for 11:00 PM exactly before emerging from his house and making the stupid walk.
His heart was pounding. He stared through his peephole to make sure there wasn’t a crowd of people watching. He couldn’t see anyone. The windows of the neighbourhood houses were all dark. He checked his phone’s clock. It was game time. He took a deep breath and then he threw the door open. He started walking down the sidewalk, moving quickly so it would be over and done with quickly. He stumbled slightly in his heels but he managed not to fall. He turned around as soon as he reached the street, and he started hustling back towards his front door. He wanted to look around to see if he could spot anyone watching from the bushes, but he was too afraid to look. He bit down on his tongue and tried to convince himself that there was no one watching.
He slammed the door firmly behind him and he quickly took a seat on the couch to catch his breath. He was strangely exhausted, his heart pounding at a mile a minute. He’d just walked outside dressed as a woman. He pulled out his phone and checked his bank balance. The money was all there—and there was no way for the sender to retract the payment. And so what if this M. Maker guy posted some video on the Internet in an attempt to humiliate Ernie? Ernie didn’t
even look like himself with that wig and that makeup. No one would believe it was actually him.
He found himself in front of the mirror again, staring at his face, impressed by how good a little bit of makeup actually made him look. He ran his fingers down his cheekbones. He’d never noticed how prominent his cheekbones were before. And his eyes were so big and beautiful…
He shook his head and said, “Snap out of it, man.” He went to the bathroom and got himself cleaned up. He didn’t understand what he’d just done, but he didn’t need to understand. Now he had enough money to pay his phone bill and most of his rent—enough to keep him off the streets for another month, anyway.
CHAPTER IV
Francis had just gotten home from work when there was a knock at his door. He wasn’t going to answer it, assuming it was just someone soliciting money for some political something or another, but the person at the door just kept knocking. So Francis caved and answered. “Is something wrong?” he asked.
Francis didn’t recognize the man standing on his doorstep. He was a younger guy with shaggy hair and a suit that was too big on him. “Hello Francis,” the man said. He sounded strangely nervous. “I’m here to invite you to a charity dinner, raising funds to help kids with cancer.”
“I’m sorry, but I don’t have any money to spare right now,” Francis said. He tried closing the door but the young man stepped a foot in the way.
“Please just listen, sir,” he said. “You don’t have to pay anything. The dinner is free and there is no donation required.”
“Then who is paying for the kids with cancer? And who’s paying for the dinner?” Francis asked.
“I’m sorry, but I don’t know. But we would be very happy if you would come and support the cause.”
Francis was silent for a moment, trying to wrap his head around the presented offer. “I don’t get it. I think I’m going to pass,” he said. He tried closing the door again, but that foot remained the way.
“Please, sir—I think you should go. Your support would be tremendously appreciated. And there will be lots of singles there.” Francis finally clued in—his name must have ended up on some mailing list when he signed up for that online dating website. He knew he should have read through the website’s terms before agreeing to them. “It’s an event you won’t want to miss.”
“What do I have to say to you to leave me alone?” Francis asked, feeling increasingly frustrated.
“Tell me that you’ll go to the event. I’ll put your name on the list. There will be lots of food and many singles in attendance. Try to think of a better way to meet a partner,” the young man said, his voice sounding rehearsed.
“Do you work for the charity?” Francis asked.
The young man was silent. “I’m putting your name down. Here’s the information. We look forward to seeing you there.” The young man handed Francis a flyer and then he took off. He got into his crappy car and zipped away. Francis looked down at the flyer. The event wasn’t until Friday—five days away. Apparently a suit and tie were required for men, which meant Francis would have to get his suit pressed and cleaned. And the event was on the other side of town, which meant he would have to take his crappy broken car instead of the bus. It didn’t seem worth it, so Francis tossed the flyer into his recycling bin.
That night, Francis had a date with a girl he met on the dating website that had apparently given his address away to solicitors. She was cute in all of her profile pictures, and she was apparently interested in all of the same things as Francis.
But her photos turned out to be old—almost ten years old. Since the photos were taken, she’d put on nearly eighty pounds, and it turned out she wasn’t interested in any of the same things as Francis. Ten minutes into their dinner date, she said, “I have a confession to make. I changed my profile before messaging you, so our interests would be the same. I don’t actually know anything about jazz or horror movies. Oh gosh, I’m so glad that’s off of my mind. Now I can relax. You know what they say: honesty is the foundation of a good relationship!”
Francis found himself feeling horribly uncomfortable through the date. He ran out of things to talk about before the entrees arrived. And then his date insisted on ordering the baked desert, even though the waiter warned her that it would take twenty minute to bake. “We don’t mind. We’re having fun. We’re on a date—it’s our first date,” she said to the waiter. Francis sunk into his chair.
He gave the dating website another shot the next evening, going on a date with a girl he reached out to, who happened to be free and looking for something to do. “Want to see a concert with me?” the girl asked. “My friend bailed on me.”
So Francis went to meet up with her. In her pictures, she looked like a sweet little blonde with big blue eyes. But those photos were old and extremely misleading. Now, her hair was dyed black. Her fingernails were painted black and she had tattoos on her neck, one of which said ‘CUNT’. The concert was in a grungy bar, and it was a death metal band. Francis’s black-haired date threw herself into the middle of a mosh pit and started bouncing from person to person. When she finally emerged, her lip was bleeding and she had a bruise forming on her face. “What’s wrong? Don’t you want to dance?” she asked Francis.
Francis excused himself for the bathroom, and then he snuck out and ran home. As soon as he got home he deleted his online dating profile and started coming to terms with the fact he would probably never find love. And maybe that was for the best. Maybe he was better off alone, sleeping by himself in his bed, waking up staring at his blank wall. Maybe dying alone wouldn’t be so bad.
He went to take out the recycling when he noticed that flyer on the top of the bin—the flyer for the charity dinner, which he was apparently signed up to attend. There was supposedly going to be singles there—maybe giving it a go wasn’t such a bad idea. It was a free dinner, after all.
CHAPTER V
It was two days after walking out to the street in a dress and a wig when Ernie received another box, once again unlabelled, and once again full of women’s clothing. This time there was a black pencil skirt, a grey sweater, black thigh-high stockings, and another pair of black strappy heels. There was no letter in the mailbox to accompany the box of clothes, but Ernie had a feeling that letter was coming.
He found himself sitting by his bedroom window, where he could see anyone coming up to his door. He ran to the mailbox after the mailman dropped the mail off, but there were no strange letters from unknown senders. So Ernie went back into his bedroom and he continued to keep an eye on his doorstep. But eventually he got tired and had to go to sleep. When he woke up, there was an unmarked letter in the mailbox, and he knew it was from M. Maker.
“Ernie, you did good the other night, but we both know that you can do a lot better. You didn’t even bother to shave your legs—and yes, I noticed. Your eyeliner was sloppy, so at the bottom of this letter is a list of makeup tutorials that I think you will find very helpful. Tonight I want you to go to the bar, have a drink, and then head home. You can pick the bar—but you need to up your game. I don’t want to see any leg hair and I would like it if you put more effort into walking like a lady. Elegance is important, you know. You can either wear the dress from last week or the clothes I dropped off yesterday—or you can mix and match—I’ll leave that up to you. And once again, accept the challenge by accepting the e-transfer in your e-mail inbox. Oh, and by the way, I could tell that you had your boxers bunched up under your dress. I put panties in the box for a reason—so wear them.”
Ernie’s heart throbbed and his gut turned. He couldn’t possibly go to the bar dressed as a woman. It was one thing to walk to the street and back, but it was another thing to walk eight blocks, order a drink, sit with a group of strangers, and then walk back home—and they would be strangers if he were lucky. It wasn’t unusual to bump into people he knew at the local bars, and Ernie wasn’t about to get on a bus, or risk taking his unreliable car across town.
He had no i
ntentions of accepting the challenge until he saw that e-transfer in his e-mail inbox. This time he was being offered $900.00. That was a lot of money—more than enough to cover the rest of his rent, and to get his vehicle properly fixed. The job prospects weren’t looking great, so maybe it wouldn’t hurt to fill the gap with a quick jaunt down to the bar. M. Maker only said he had to order a drink—he didn’t say that drink couldn’t be a shot of whiskey. Ernie could be there and back in twenty minutes if he was efficient.
So he accepted the money transfer. As soon as that money went into his bank account, his heart started pounding. His hands trembled and he found himself trying to control his breathing. He was really going to do it.
He started having second thoughts later that afternoon. What if someone did recognize him? What if one of his neighbours saw him slipping out from his basement suite? What if he went to order a drink and he froze up, and everyone in the bar could tell that he wasn’t really a woman? Was the humiliation worth a measly $900.00? It was too late to backtrack. He had no way of returning the money to M. Maker, and he didn’t want to see what would happen if he didn’t follow through with the promise he’d made when he accepted the money.
So he started getting ready early. He slipped into the pencil skirt, which unsurprisingly fit perfectly. The sweater was tighter than he expected, but it looked good, especially with the bra underneath, once the bra was stuffed with a few wads of toilet paper.
He spent some extra time doing his makeup. He watched a few of the tutorials suggested by M. Maker, and he even got a few helpful tips from the tutorials. One of the tutorials showed him how to do some basic contouring, which helped in making him less recognizable.
It took nearly three hours before Ernie was satisfied with his look. Then he stood in front of the mirror and scrutinized every little detail. He looked cute, and strangely feminine. Did this M. Maker know that Ernie would look feminine or was it just a coincidence?
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