Chapter 22: Brian Becomes a Sissy, Part 9

Brian watched Helena drive away in the cab. He sighed. Insisting he met his commitment to feeding Tim and going in drag with him to Sporties was the right thing to do, but why did it feel like he’d blown another chance with Helena?

‘You’d think doing the right thing would feel good,’ Brian mused. ‘Typically, it feels like shit, though.’

After texting Tim that he’d see him the next evening, Brian went to bed early. The thought he’d blown another chance with Helena sent the black dog of depression to visit, and Brian didn’t want to think. He got up on Friday feeling melancholy, but as he drank his morning coffee, he gathered his strength and girded for battle. Another day as good as the previous four, and not only would he break his own personal record for trades, he’d break the firm’s all-time record. The one held by Chris Savage.

Breezing into work, Brian said a cheery hello to the receptionist before momentarily stopping. He looked at her curiously before saying, “Umm, you’ve done something different with your hair. Changed its colour and shortened it by quite a bit. It looks good!” He walked to his desk, leaving a stunned Rebecca, the receptionist, gaping at him. It was the first time any male had noticed she’d changed her hairstyle, let alone complimented her for it.

Previously, Rebecca had lumped Brian in with the rest of the so-called alpha males working here who acted all macho and boastful. ‘Beta chumps’ is what Rebecca called them behind their backs. ‘Small dicked wannabes who couldn’t find a woman’s clitoris with directions and a magnifying glass.’ It was no wonder she turned to her girlfriends for relief most Friday nights. She’d heard Brian had broken up with his girlfriend and wondered if he was available.

Unaware of the damp pussy he’d left behind him, Brian logged into his computer and opened his trading program. Looking through the nightly results from the Nikkei and Dow, he started making notes and identifying trends. There’s an old saying in the finance industry. “America sneezes, and the rest of the world catches a cold.” George W. was in the White House, and Brian was worried about America’s economic future and her growing international debt. The problem was that Europe was even worse, and most of Asia was a basket case. Brian began moving his various portfolios closer to home, investing in resource companies such as Rio Tinto and BHP Billiton. It was time to move away from speculation and into blue-chip stocks.

“That’s it for the week, champ,” Chris Savage said at Brian’s shoulder.

Brian looked up and saw that it was almost five. He looked at his ongoing stock value and smiled, satisfied that he’d made a solid profit for the day. He closed off the last sales, logged out, and shutdown his computer.

“Didn’t like how the Dow Jones looked?” Chris asked.

“I think there’ll be a correction either tonight our time or Tuesday morning for us. By Friday next week, I’ll move back in and pick up solid stocks in profitable companies that are currently low and then sell them when the rebound happens.”

“I did the same thing. You surprised me by seeing the trend at the same time as I did. Well done.”

“Thank you, Sir.”

“Very good. Keep up the good work, and your name will come up for partnership again.”

“I look forward to that, Sir,” Brian said dutifully while thinking if Helena was still prepared to invest, he’d talk to Harry Mills about starting their own firm before then.

Chris smiled and walked away. He thought, ‘I’ll milk a few more months from him before he gets antsy about not being made partner. Then I’ll hit him with the buy-in figure. He’ll need at least another year to save that much. In the meantime, the firm makes all that profit, and all we have to do is to pay his wage.’

Brian got off at the shops on the hill above the start of Chapel Hill Rd so he could purchase some Chinese takeaway to eat with Tim later. Deciding he hadn’t gotten enough exercise lately, he walked down the hill and then back up to his street. He looked, not expecting to see Helena, and wasn’t surprised that she wasn’t there. He sighed, wishing he could turn back time again. However, as the saying goes, ‘Wish in one hand. Shit in the other. See which one fills up first.’ He went inside and put the takeaway in the fridge.

With time to kill, Brian changed the sheets and put a load of washing on. Then he got in the shower and carefully removed every speck of hair he could find on his body. He couldn’t reach his entire back, but it was only his lower back that was hairy, and he was certain he’d gotten that. Once he’d finished, Brian wrapped a towel around himself and removed the clothes from the washer. He took them outside and hung them on the line.

Millie, his Southside neighbour, was also hanging washing. She looked over, and despite being a married mother of three, her juices flowed. She’d surreptitiously admired Brian ever since he’d moved in. He never closed the blinds in his exercise room, and she often perved on him as he worked out in just his shorts and runners. In a teasing tone, she said, “You’d look better without the towel!”

“Maybe,” Brian returned, smiling. “But then I’d have your husband climbing the fence, holding his shotgun.”

“I’d have called it a cocktail sausage,” Millie said, not really joking. “But sure, his,” she made air quotes, “shotgun.”

Brian laughed. The washing was hung, and he didn’t know what to make of her flirting, so he smiled at her and turned to go inside. About halfway to his side door, Brian ‘accidentally’ let the towel drop.

“Oh, my!” Millie gasped. “Turn around!” Brian laughed again, picked up the towel and shook his muscular ass, and went inside. “Spoilsport!” Millie called after him.

Brian shook his head. Ever since Helena had crashed so dramatically into his life and Brian had stopped chasing every skirt in his vicinity, women had come onto him. Millie was mostly teasing, but he knew if he’d taken her up on her implied offer, she’d have had him nuts deep inside her in a flash. Brian marvelled again at the differences Helena had wrought in him, but then his depression crashed back over him, almost drowning him with sorrow about had badly he’d fucked up.

He sat on his couch wearing only the towel until he heard a cheery, “Knock, knock. Yoo-hoo, is there a hunky gay virgin living here who wants to dress as a girl and come out?” Unable to resist chuckling, despite his depression, Brian let Tim in. Tim held two bags up. “I come bearing gifts. Where shall I put them?”

“Come into the kitchen. I’ll stick our dinner in the microwave, and you can show me while it heats. Would you like a beer?”

“Sure,” Tim said teasingly. “I’ll drink some more of your rich-bitch beer.” Tim entered the kitchen and put the bags on the table. He saw Brian wore only a towel and that his eyes were red. “The email didn’t work, huh?”

Brian half shook his head, half shrugged. “It did kind of. She was waiting for me when I came home on Thursday. We spoke, and she said she’d meet us at Sporties tonight.”

“So, small steps, but progress all the same. Maybe seeing you out with a bunch of drag queens might help her see you in a different light.”

“One can only hope.”

The microwave dinged, and Brian brought out the rice and the two meals he’d brought home. He’d gone for a fairly standard Aussie man’s selection: Stir-fried chicken and cashews and sweet and sour pork. Tim rolled his eyes at the bland choices.

“Jaysus! You could have at least gone for the Mongolian lamb. Something that has some taste to it.”

Brian shrugged. His palate was pretty tame. Even Mongolian lamb was a little spicy for him. Still, the meal was relatively tasty, nourishing, and filling. The new friends ate and drank beer in companionable silence. After eating, they took a turn each in the bathroom to clean up and brush their teeth.

When Brian returned to the kitchen, Tim said, “Right, let’s get started.” He looked at Brian’s face critically. “Go shave again, and this time, after you’ve shaved with the grain, shave against the grain. That’ll give you a closer shave. I have an astringent to use after you’ve shaved to ensure your face doesn’t rash.”

Brian obeyed, and when he returned, Tim handed him a bottle of witch hazel. Brian poured some into his hand and then splashed it onto his face. “That stings,” he muttered.

“Yeah, a bit at first,” Tim replied, agreeing. “Now sit here under this light and let me fix your face.” Tim spread Dermablend foundation over Brian’s face, explaining what he was doing along the way. “I’m using Dermablend because it gives the best coverage, especially for blokes like us. You probably didn’t notice, but I played a lot of rugby when I was at school. My face has many scars from nicks and acne. Dermablend covers them all.”

Tim then used a dark red blush to bring out Brian’s cheekbones and to streamline his brow, nose, and jaw. He described what he was doing, how, and why. Eyeshadow followed. A light colour on the inner lid, blending to a magenta on the outer. Next, Tim used an eyebrow pencil to draw Brian’s eyebrows in and a little higher, increasing the brow’s arch. Eyeliner came after that, with Tim drawing wings out from the corners to make Brian’s eyes appear wide and rounder. Fake eyelashes followed the eyeliner, and then Tim drew Brian’s lips. He made the outline about 5 millimetres wider than Brian’s actual lips, and then painted them in, giving Brian a pouting, bee-stung look.

Tim examined his work and smiled. “Hmm ... I’m a fucking genius. Hang on, I brought one of my wigs.” He retrieved it from the bag and put it on Brian’s head. “Honey, if you’re going to wear wigs all the time, it’d be better if you either shaved your head or cut your hair really short. Something like this,” Tim added, rubbing a hand over his short, spiky hairdo. Tim adjusted the wig until it sat properly and then used hair clips to ensure it remained where it was. “Okay,” he said. “Go check yourself out.”

Brian stood and walked to the bathroom. He turned the light on and studied his reflection. When Helena did his makeup, he looked what he was—a man wearing makeup. The image staring back at him looked like a butch woman attempting to tone down her inherent masculinity, but clearly a woman, nevertheless. He was impressed.

From the kitchen, Tim lisped, “Move your ass, honey. We’re running out of time for me to get to Sporties and change for the first show. Get your delicious ass into some stockings, panties and a bra and get it in there quickly.” Brian obeyed. When he got to the kitchen, Tim handed him a skin-tight, spangly dress that seemed barely long enough to cover his ass. “Up on the table so I can tape your cock and balls away.”

Brian obeyed that instruction, too. Then he put the dress on. As he’d feared, it was only just long enough to leave him decent. “When you get out of the car, walk with your head up and your shoulders back. Strut like you’re the queen bitch and own everything and everyone around you. Trust me, if you do that, every straight and bisexual guy’s eyes will be on your ass and tits, and no one will know you’re a tranny cos they’re sure as fuck not looking at your face.”

Tim looked at his watch. “Shit! We need to hurry,” he said, rushing him out the door.

Tim drove them to Sporties, parking in a reserved spot at the back. He ran inside, leaving Brian to get out and enter on his own. Gulping nervously, Brian got out of Tim’s car and walked up the stairs. It wasn’t until he reached the back door that he realised that unless you had a key, it couldn’t be opened from outside. He returned down the steps and walked up the driveway to the street. He only remembered to strut when a car passed and a guy yelled, “Fucking poofter!” out the window and threw a beer can at him. It missed, fortunately. But the act angered Brian, and he strutted to the front entrance like a model down a catwalk.