The fabulous pink umbrella.

Henry woke up the next morning with a splitting headache. He hated headaches. As he stumbled out of bed towards the bathroom, he thought back to the night before: had he had too much to drink? No, he'd left the bar before he'd finished his first cosmo. It'd been that country boy's fault. Leroy Pickler didn't belong up here, Henry thought. Who the hell listens to country music in the middle of Maryland? Not him, you'd be sure.

Henry hadn't stayed out late last night. After he left The Bar, he headed to Diner Royale before sitting himself on the park bench next to the synagogue and surveying the sights. Becoming Dorothy thrilled him. He loved the makeup, the clothes, the hair, the shoes, the act. And best of all, no one knew that he wasn't legit. No one knew that Henry was also Dorothy – who could ever guess? They were polar opposites of each other; despite the obvious differences, Dorothy was an extrovert. She enjoyed going out, drinking, socializing, shopping. Henry, on the other hand, would never carry on a long conversation. He went out as himself only a few times a week, including his weekly Monday night trip to Ming Ming's for a solo dinner. The rest of the time he left Washington Heights apartments, he was Dorothy. And he never tried to pick up any other guys – he wasn't like that. He just dressed up for the thrill of it.

His head throbbing, Henry opened the medicine cabinet and took out the bottle of Ibuprofen. He popped two of them, swallowed, turned on the sink, filled his cupped hands with water, and drank from them. He made his way back into his bedroom, wondering what had given him such a monumental headache.

Then he saw the rain. It was pouring down, dripping from the ledge above his window, smacking against the glass. He walked over to the window and looked down over the town. On days like this, Washington Heights looked gloomier than ever. He saw a couple umbrellas here and there, making their way down either Baker or Bucher street. The umbrellas were all black except for one – a bright pink one that stood out fascinatingly among the bleakness of the town. Henry watched the pink umbrella intently – what a fantastic color! He'd have to get a new dress like that, he decided. Some ways up the street, the pink umbrella stopped in front of Diner Royale, and a figure dressed in a frilly pink and white showgirl-like dress emerged from underneath before stepping into the diner. Henry couldn't see much of the lady, but he knew that Dorothy would just have to meet her – and, of course, find out where she'd purchased that fabulous ensemble. It was time for a new wardrobe.

A night on the town.

It was pitch black outside by the time Henry was ready to leave. He had finished assembling himself. Tonight, he was wearing a knee-length wool skirt, light orange with off-white polka-dots all over it. He wore a modest off-white blouse, under which he'd donned his bra, a Wonderbra that had enough air and liquid inside it to create a substantial chest from nothing. Since the nights had become cooler, he decided to wear off-white tights over his freshly-shaved legs. Instead of a jacket, he'd gathered an orange shawl around his shoulders to keep himself warm. He wore pearl posts in his ears and a pearl necklace around his neck, which matched the off-white of the shirt and polka-dots. To top it all off, he put on his new brown leather boots with the one-inch block heel. As always, he had pinned his light brunette wig securely into place. Wouldn't want to lose that, after all.

Picking up his brown purse, he looked out the peephole of his door to make sure no one was around. He opened the door and stepped out.

He was no longer Henry. In fact, her name was Dorothy.

Dorothy began the descent down the grungy stairs and after eleven flights, walked out onto the street. She was greeted by a harsh rush of cold air that make her hair blow and her shawl whip in the wind. Dorothy turned and walked down the street. It was barely a block to The Bar, but by the time she got there, she was frozen stiff. She was immediately greeted by the loud shrieking of a microphone. She whipped her head over towards the front of the bar – there wasn't much of a stage, just a space – and saw a young boy in a cowboy hat sitting down in a chair with a guitar. She walked over to an empty seat at the bar and sat down. The bartender recognized her. "Good evening, Miss Dorothy," he said. "I supposed you'll be having the usual cosmopolitan tonight?" Dorothy replied, and the bartender started mixing her drink. The bartender had no idea who Dorothy was – for all he knew, she was the nice lady he saw a few nights a week. And he never saw her during the day.

Before the bartender finished making the drink, the young boy on the stage started talking. "Excuse me, everyone – I'm Leroy Pickler, new in town, just got off the Greyhound bus yesterday, straight up from Paintlick, Kentucky. I'm tryin' to make my way best I can as a country singer, so if you'll be obliged to drop any tips right here in this bucket, I'd be real thankful." Leroy held up a dirty old paintbucket and placed it at his feet. When he looked up, he met eyes with Dorothy. He gave her a strange look before breaking eye contact and looking down at his guitar. "This song here's for my mama," he said. "I just know someday I'm gonna make her so proud."

Leroy began his song. It was a twangy country song, the kind like Dorothy's own mother used to listen to. Dorothy hated anything that reminded her of her mother. After the first song was over and he began the second one, Dorothy couldn't take it. She got up, threw a five dollar bill on the table and left her bright pink cosmopolitan sitting there, unfinished.

Meet Dorothy.

It was late in the afternoon, somewhere between four and five o'clock. The sun was slowly creeping towards the horizon, and the chilly wind of the autumn dusk whipped around Henry's face. He was sitting in one of those white plastic lawn chairs, which he'd leaned back against the sliding door, and he had his feet propped up on the balcony railing. The balcony was small. It was hardly wide enough to move around on, but he was glad he had one. He enjoyed the fresh air – although it smelled like a bad mixture of greasy Chinese food and old garbage, it was a welcome relief from the stuffy air inside the apartment.

As the shadows lengthened and the sun sunk lower and lower, Henry could feel the temperature dropping. The cool wind whipped across his face as he sat his chair down on all four legs and stood up. Oh, he was stiff. He hated his god forsaken mattress. In fact, he hated this god forsaken town. How he ended up here, he could barely fathom. But that was another story.

Henry opened the sliding door and went inside. The apartment was neat and tidy, just the way Henry liked it. He walked through the kitchen, which also served as a social room, dining room, and entrance to the apartment, and turned into the bathroom. It was dark in the windowless bathroom, and the light above the mirror dimly illuminated the small space. Next to the sink sat a set of drawers. Henry opened the top drawer and gazed at its contents. Red lipstick, fake eyelashes, eyeshadow, eyeliner, blusher, powder. A box of fake French-manicured fingernails. A bottle of cheap drugstore perfume. A pair of eyebrow tweezers and an eyelash curler.

He started with the eyes. First he drew the eyeliner on, just thick enough for it to be noticeable. Then he drew a thin line of eyelash glue around each eyelid before gingerly planting the eyelashes on, one by one. He had mastered this task, now, after quite some practice. He looked through his eyeshadow options, and chose a sparkle-y lavender one; he dusted his eyelids with it. Next, he picked up with powder. He brushed it all over his clean-shaven face before putting blusher on the apples of his cheeks. He was almost ready now.

He checked his eyebrows – had any stray hairs sprouted since the last time he'd plucked? Of course, he found a couple. He picked up the tweezers and plucked uncooperative hairs out, one by one. Setting the tweezers gingerly back in the drawer, Henry picked up the fake fingernails. He sat on the closed toilet seat and rested his fingers on his lap as he glued each fingernail to each finger. Like the eyelashes, he'd mastered this task; it took him only a matter of minutes.

Standing again, he picked up the red lipstick from the drawer. This was the one thing he absolutely hated, and he absolutely hated it because it reminded him of his mother. His mother, in turn, reminded him of his family. And Henry hated his family. They'd kicked him out when they'd learned he was gay – and his mother, who'd loved him so much up until that point, told him that she hoped she'd never see him again. Henry had been heartbroken.

He held the lipstick in his hands, running his fingers over the plastic green case. It was Clinique lipstick – the same kind his mother wore. As much as he hated his mother, he couldn't tear himself away from the lipstick. Plus, it was an essential factor in his makeup. He opened the tube and applied it carefully to his lips, smacking them together when he was finished.

Henry put the top back on the tube and put it into the drawer. Closing the drawer, he surveyed himself in the mirror. His face was ready. Now he just needed his hair and an outfit.

Then he would be ready. He would leave the apartment and hang around the Washington Heights neighborhood. No one would know it was him – he looked pretty legit. Plus, no one would recognize introverted, shy Henry's connection with a young, dolled-up night-dweller named Dorothy.