Rent or Forfeit 23

Chapter 23: Dressed For Success

Back home that evening, Tommy was slumped on the sofa watching television when Monica knocked softly on the door frame. “Hey, can I come in?” she asked with a gentle smile.

“Sure, take a seat,” Tommy replied in a tired-sounding voice, gesturing to the cushion next to him.

Monica crossed the room and sat down, her hands resting in her lap. “So, how was work today?” she asked lightly.

“Alright, I guess,” Tommy muttered, not taking his eyes off the screen. “Well, apart from everyone thinking I’m a girl obsessed with the colour pink,” he added, the sarcasm dripping from his voice.

Monica let out a small sigh. “Look, I know all this seems a little extreme, but it wasn’t supposed to be like this. It started as a way to help you, to push you to get your life on track. But you know Sarah… she always takes things too far.”

“Too far?” Tommy snapped, finally turning to look at her, his glossy lips twisting in frustration. “Monica, look at me! She's evil. That's what she is. Why else would she try to turn her brother into a girl?"

“I know,” Monica said softly, her tone apologetic. “You’re right. Things have gotten out of hand. I’ll talk to her, okay? See if I can get her to ease up. But, you need to understand… Sarah’s been through a lot. She’s the one who found me… after… after I tried to end things.”

The room fell silent. Tommy’s eyes widened as the words hit him, and his lips parted, but no sound came out. After a moment, he looked down. “Because of me?” he asked, his voice barely above a whisper, guilt etched into every word.

“It’s not about blame,” Monica said, offering a sad smile. “That was a long time ago, and I’m in a better place now. And honestly, so are you, right?”

“Right,” Tommy echoed faintly, lowering his gaze to his painted toenails nails and smooth legs. His throat tightened as he swallowed hard.

Monica reached over and squeezed his hand. “I didn’t mean it like that,” she added quickly, sensing his discomfort. “I just meant you’ve grown up a lot. You’re more considerate, more responsible. And honestly,” she smirked slightly, “you make a super cute girl. I know there’s a part of you that likes being Tammy.”

“What? No way!” Tommy exclaimed, yanking his hand away and waving his long-nailed fingers in protest. “I’m a man! Men don’t like… this!”

Monica shrugged with a knowing look. “Some do. And there’s no shame in that. People like what they like. I’ve seen the way you look at yourself in the mirror when you think no one’s watching. Are you seriously telling me there’s nothing about being Tammy that you enjoy? Not even a little?”

Tommy opened his mouth to protest, but the words didn’t come. Finally, he sighed, looking sheepish. “Well… I guess it’s not all bad,” he admitted quietly, a faint blush creeping into his cheeks. Then, almost immediately, he straightened up and added, “But there’s a lot I don’t like: my feet hurt like hell after a whole day in heels, these nails make everything a nightmare, and all the pink! It’s super embarrassing.”

“I knew it,” Monica exclaimed, latching onto the part she wanted to focus on. “And there’s no need to be embarrassed. It’s just a colour. I actually think you’re really brave. It takes guts to do what you’ve done - experiencing life from the other side. You’ve even seen first-hand what it’s like for women in the workplace.”

“Well, not for much longer,” Tommy muttered, shaking his head, and crossing his arms, frustration etched across his face.

“Why? What happened?” Monica asked, her concern evident as she leaned forward.

“Nothing, really,” Tommy groaned. “It was always just a temp job. But this woman, Jill… She said I could stay on, but only if I go into work looking like a—” He hesitated, searching for the right word. “Like some… slut.”

“What?” Monica gasped, her voice rising in shock. “What do you mean? Explain. What exactly are you talking about?”

Tommy rolled his eyes and chuckled dryly before launching into the story of his conversation with Jill earlier in the break room. He didn’t sugar-coat anything, recounting Jill’s pushy behaviour and how she wanted him to dress provocatively to impress the boss. Monica listened intently; her expression serious as she let her brother vent without interruption. When he finished, she tilted her head, her eyes narrowing thoughtfully.

Then, probing for information to a question that confused her, she asked gently, “Do you like the job?” Her tone was calm, but her intent was clear - she was trying to understand. Did some part of Tommy actually like the idea? Was he bringing this up because, deep down, he was looking for her permission, her acceptance?

“Kind of,” Tommy admitted after a moment’s hesitation, his tone softening. “It’s easy work, and everyone else is really nice. And honestly… I don’t fancy going back to that temp office to start over.”

Monica nodded slowly, understanding dawning on her face. “Okay,” she said, her voice firm but kind. She had her answer. “I think you should do it, but on your terms. Don’t let this Jill woman push you into doing something you’re not comfortable with.”

“And how exactly do I do that?” Tommy asked, scepticism clear in his voice.

Monica smiled warmly, her confidence reassuring. “Set your alarm for an hour earlier tomorrow, and we’ll figure it out. Together. Deal?”

Tommy stared at her for a moment, his plumped lips pressed into a reluctant pout before he nodded. “Deal.”

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The next afternoon, Tommy tottered into a conference room on sky-high pumps, their tight ankle straps biting slightly with every step. Mr Hopkins, already in the room, was leafing through a folder on the far side of the large space. He barely acknowledged Tommy’s entrance, leaving him standing awkwardly in the middle of the room, unsure of what to do with himself.

After what seemed like an eternity, Mr Hopkins finally looked up and smiled politely. “Tammy, would you call down and ask for a pitcher of water for the table? Our guests will be arriving shortly, and I’m sure they’ll appreciate something to drink.”

“Yes, Mr Hopkins. Of course,” Tommy replied, forcing a nervous grin onto his heavily made-up face.

Before he turned to strut over to the phone, he caught Mr Hopkins’s gaze lingering on him. The businessman’s eyes roamed over his feminine form, pausing just a little too long, making Tommy’s stomach twist with a mix of nerves and a strange, confusing thrill. He felt a warm flush creep up his neck, his face heating beneath the layers of makeup.

His outfit certainly demanded attention. The pink pleather miniskirt clung tightly to his hips, its hemline ending daringly high on his nylon-clad thighs. It was the kind of attire that turned heads and raised eyebrows, hardly what one would call professional office wear. But Jill had been thrilled with the look that morning, her approval as enthusiastic as it was unsettling.

Jill had been equally excited about the matching long-sleeved sweater which clung to his slender frame and dipped low enough to showcase an eye-catching glimpse of his faux cleavage. “Perfect for charming the boss,” she’d remarked with a wink, her eyes lingering on his dramatically voluminous hair. Monica had insisted on blow-drying and styling it that morning, giving it a fullness that only added to Tommy’s discomfort as Jill’s gaze swept over him.

(See image 23)

Apart from the grogginess of waking up extra early, Tommy had surprisingly enjoyed spending time with Monica that morning. Her cheerful attitude and endless compliments had been contagious, and they’d shared plenty of laughs while putting together his look. The final pink ensemble screamed "girly girl" - a look that Tommy couldn’t have imagined himself wearing a few months ago. Yet, as he left the house that day, he felt an unfamiliar sense of confidence. The stares and whispered comments didn’t seem to bother him as much; he held his head high, deciding to own the attention.

The business meeting was long and, for Tommy, a surreal experience. Standing by Mr Hopkins at the door, he greeted two sharply dressed men with a forced smile. After the introductions, he tottered over to the sofa, carefully navigating the plush leopard-print carpet in his towering 16-centimetre stiletto heels. Every step was purposeful, his full focus on not wobbling. Once the men were seated, Tommy smoothed the short hem of his form-fitting skirt over his backside with his long, acrylic nails, the creak of the material audible in the otherwise quiet room. Slowly, he lowered himself onto the sofa, folding his nylon-clad legs neatly at mid-thigh.

For hours, he sat in silence, scribbling notes while the men discussed business. The tightness of the skirt and the pressure crossing his legs applied to his groin area caused all kinds of discomfort, but he didn’t let it show. Keeping his posture straight, he smiled throughout, pushed out his enhanced chest, and occasionally bounced one leg in what Jill had called "a flirty way." This, of course, was all part of her master plan - she’d been the one scheduled to accompany Mr Hopkins to the meeting, but claiming to feel unwell, she’d arranged for Tommy to take her place.

At the end of the discussions, a deal had been struck, and the mood in the room was triumphant. The departing men were all smiles, none more so than Mr Hopkins.

“Thank you, Tammy. That went perfectly,” he said as Tommy closed the door behind the guests. “Mr Patel really took a liking to you. Mr Simons too.” Tommy blushed, remembering the way the men's eyes had lingered on his legs throughout the meeting.

“Come over here for a moment,” Mr Hopkins added, gesturing to the sofa. “There’s something I’d like to discuss with you.”

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“Oh my god! He didn’t? What a perv!” Maddison exclaimed, her voice brimming with outrage as Tommy recounted his day during their evening phone call.

“It wasn’t that bad,” Tommy said, trying to downplay Mr Hopkins’ light squeeze of his pantyhosed thigh as he offered him a permanent position at the company. “The important thing is, I’ve got a proper job now. And besides, he seems like a nice guy.”

“Oh my god! Do you have a crush on your boss?” Maddison teased, her tone shifting to playful curiosity.

“Eww! No way! He’s like forty or something,” Tommy shot back, horrified by the suggestion. “I just meant he’s... you know... like smart and funny.”

“Uh-huh, sounds like a crush to me,” Maddison teased playfully.

“Stop!” Tommy said with a groan. “Stop being gross. I don’t fancy Mr Hopkins. I’m just grateful for the job, that’s all. It’s going to be my way out, Maddy. A few months of saving, and I can quit, move out of here, and start over.”

“Sounds like a solid plan,” Maddison said approvingly. “But what are you going to do about your ID?”

“ID? What do you mean?” Tommy asked, his light-hearted tone vanishing as confusion crept into his voice.

“Well, you mentioned signing a contract, right?” Maddison replied, her tone taking on the air of someone explaining the obvious. “With the temp agency sending you, they probably didn’t check. But now that you’re going to be an official employee, they’ll for sure ask to see your ID. Are you seriously going to hand over a passport that says Tommy Jenkins with a picture that looks nothing like you?”

“Oh, shit! I didn’t think of that,” Tommy groaned, twisting a strand of his long, pastel-purple hair between his thumb and forefinger. “What am I going to do?”

“Hang on, give me a minute,” Maddison said briskly. “I’ll check something and call you back.”

The line went dead, leaving Tommy alone with his thoughts. For the next twenty minutes, he stared at his phone, his long nails tapping anxiously against its screen as he played out possible scenarios in his mind - none of them good.

When Maddison finally called back, he answered clumsily, his acrylic nails still not cooperating with the touch screen. “What did you find out?” he asked, his voice taut with nerves.

“Okay, I did some research,” Maddison said confidently. “And it looks like you’ve got two options.”

Two options?” Tommy repeated, his voice tinged with sarcasm - the image of the dreaded purple hat flashing through his mind. “Alright, hit me with them.”

“Option one,” Maddison began, “you tell them the truth - that you’re transgendered. Legally, they can’t refuse to hire you. It’s discrimination, and if they try, you could take them to court and win a ton of money.”

Tommy winced. "And the second option?” he asked not liking the thought of everyone at the office finding out what was beneath his skirt or having to go to court - money or no money.

“Well,” Maddison continued, “you could legally change your name and gender. You'll probably do this sooner or later anyway, right? And it’s easier than you think! You can do something called an unenrolled deed poll. Basically, you write a few sentences renouncing your old name, as they call it, and then declare a new one." Her voice took on a slightly hesitant rhythm, as though she were reading unfamiliar information. "Get two witnesses to sign it, and voilà! You can apply for a new passport. If you fast-track it, you’ll have it in a few days. What do you think?”

What did he think? Tommy didn’t know what to think. He sat frozen, stunned as Maddison rattled off the details like it was the simplest thing in the world. Could it really be that easy? One form, a couple of signatures, and poof - just like that, he'd become someone else. The simplicity felt almost surreal for such a life-altering decision. Yet, it wasn’t the process that gnawed at him - it was whether he could take such a drastic step.