Rent or Forfeit 21

Chapter 21: Princess Tommy

The day had started off miserably, and not just because of the freezing January wind whipping through the city. After opting for Monica’s challenge over Sarah’s, not wanting to give Sarah the satisfaction of having him as her servant all week, Tommy woke to find an outfit waiting for him. A quick glance at the ensemble hanging from his wardrobe door filled him with regret.

Walking over to the eye-catching outfit, he inspected it with dread, knowing he’d have to wear it out in public. Reaching out, he ran his fingers over the frilly skirt, feeling its soft, lightweight fabric. For most eighteen-year-old boys, wearing a skirt like this in public would be a nightmare - not to mention the strappy, low-cut top and thigh-high boots with their towering stiletto heels. Yet, Tommy was almost used to wearing such clothes by now; what turned his stomach was the colour. Apart from the crisp white top, the whole outfit was girly-girl pink - a colour he despised.

After a long shower, trying to ignore what the day might bring, he returned to his room to find Monica waiting on his bed.

“Morning, Tammy! How did you sleep?” she asked with a bright smile.

“Yeah, just great,” Tommy mumbled, his irritation evident.

“Oh, don’t be like that. Remember, you chose to be my princess for the week. Now that it's happening, you can either sulk all day, annoy Sarah, and make things harder for yourself, or you can put on a smile - like a proper princess - and try to have some fun with it.”

Tommy sighed, too mentally drained to argue. “Okay, Mon, I’ll try,” he said, forcing a small smile onto his plump lips.

“That’s the spirit! Now come over here, and I’ll help you with your makeup,” she said brightly, gesturing toward the vanity.

Tommy trudged over and sat down, eyeing the pinks and pastel colours laid out in front of him. “I’ll be out of this crazy house soon,” he thought, taking a deep breath. “I just have to tough it out a little longer.”

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After being made up by his sister, Tommy endured an excruciatingly uncomfortable bus ride into the city - each stop bringing fresh stares, whispers, and the occasional stifled laugh. He tried to ignore the attention by looking out the window, praying the journey would end. Shrinking into his seat hid him from view but also made him more aware of his humiliating outfit: the frilly pink skirt riding up his pink-pantyhosed thighs, the towering heels of his boots clattering against the floor as he struggled to find a comfortable position. Finally, after what felt like hours, the city centre came into view. Yet, any sense of relief vanished as his sisters led him straight from the bus to an unwelcome destination: a hair salon.

He followed his sisters inside, the bell on the door chiming loudly, drawing every gaze in the room. Almost immediately, a stylist came over, clearly expecting him, and began fussing over his outfit, asking him to spin and pose while showering him with compliments like “precious,” “dainty,” and “beautiful.” Tommy’s cheeks burned, and he felt a strange relief when he was finally led to the stylist’s chair, letting the attention turn elsewhere.

“You just relax,” the stylist said with a bright smile. “Everything’s arranged, and when I’m done, you’re going to look like a million dollars.”

Tommy grunted as the stylist guided his head back into the sink. He had no idea what “look” they had planned, but at this point, he wondered what more she could possibly do to make him look even more like a girl.

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Hours later, Tommy stepped out of the salon, feeling tense and uneasy. The cold wind immediately bit through his short, bright-pink jacket, making him shiver as he adjusted to the change in temperature.

“Look, Mommy! That lady looks so pretty, just like one of my dollies!” a little girl’s voice rang out nearby, making Tommy cringe. He ducked his head, hoping to avoid her gaze.

“Come along, Jessie,” the girl’s mother replied, pulling her daughter closer. “Let’s not bother the woman,” she added, giving Tommy a disapproving glance as she hurried them away.

With his head bowed in shame, Tommy tottered through the town centre, painfully aware of the stares from nearly everyone he passed. He hated the attention, but he couldn’t blame them for looking – he’d have stared too if he saw someone strutting around in head-to-toe pink, a low-cut top leaving little to the imagination, and trying to navigate the uneven cobblestones in towering thigh-high, hooker boots. Worse still, his hair and makeup were just as eye-catching as the outfit below.

How much the salon session had cost or who was footing the bill was a mystery to Tommy, as was the reason behind the barrage of photos they’d taken of him before he left. None of that, however, changed the jaw-dropping transformation he had undergone. They had gone all out on his new look, starting by removing his previous eyelash extensions only to redo them with even thicker, more dramatic ones. Then came the main event: his platinum blonde hair extensions were removed, and the stylist mixed up a strong-smelling dye, applying it liberally to his natural hair. Forced to sit through the process with the pungent paste on his head, he caught glimpses of other customers stealing glances, and he wondered what on earth the final colour would be. Anything seemed like it would be an improvement - until the stylist rinsed out the dye and brought over a set of incredibly long extensions in a pale, pastel purple. He nearly leapt out of the chair at the sight, dreading the thought of walking around with such a daring colour.

Resigned, he sat in a daze as the stylist carefully sectioned his hair and applied the new extensions, each strand meticulously fused into place. Lost in thought, he didn’t even flinch when another stylist arrived to reshape his eyebrows, simply closing his eyes and wishing he were anywhere else.

Reaching the bus stop in the centre of a large, open square, Tommy stood outside, braving the cold rather than joining the two elderly women already seated inside the shelter. The unforgiving cobblestones beneath his feet made standing still a challenge; any small movement risked his stiletto heels slipping into a crack and setting off a wobble that would be a fight to control. Cold and exhausted, he stood like a statue, silently willing the bus to arrive.

(See image 21)

"Stop pouting, Tammy. You look gorgeous," came Sarah's voice as she approached, hands full of shopping bags.

Tommy lifted his head slowly to see his two sisters watching him with barely concealed amusement. Their eyes sparkled as they took in his new look. "Oh, wow! They really did make you look like a princess," Monica said, sounding almost surprised. "Your hair is amazing, and - oh my god - your brows are so thin!"

Tommy took a deep, steadying breath, clenching his jaw. "Everyone’s staring at me, and I feel ridiculous," he grumbled. "Can we please get a taxi home?"

Sarah laughed, clearly delighted by her brother’s discomfort. "People are only looking because you look so unhappy. Try smiling a little. It looks strange for a girl dressed like you to look so miserable."

“Smile? Seriously?” Tommy whined. "The only thing that would make me smile right now is getting home. Please, Sare, can we just get a taxi? I’m freezing."

Sarah paused, taking a moment to look her feminized brother up and down before finally taking pity on him. "Fine," she said, reaching into her bag to find her phone.

Sarah unlocked her phone, scrolling casually before pausing. "Oh, by the way," she said with a sly grin, "I spoke to the salon manager before we left. She’s sending over the photos they took once they’re edited."

Tommy’s eyes widened, dread creeping over him. “Photos? Why would they send them to you?”

“Oh, didn’t I mention?” Sarah replied, feigning innocence. “The salon’s using your pictures in their new promotion. You know, for their website, social media, maybe a few posters.”

“Promotion?” Tommy’s voice cracked. “You let them take photos for that?”

“Relax, Tam,” Monica chimed in, barely suppressing her laughter. “It was a win-win. The stylist needed a model for her portfolio, and you got a free makeover. They were thrilled you agreed.”

Tommy’s face paled as the reality hit him. “You mean... anyone who walks in there is going to see me like... like this?”

“Oh, don’t be so dramatic,” Sarah replied with a dismissive wave. “It’s just a few photos, Tammy. Besides, you look amazing."

Tommy opened his mouth to argue but couldn’t find the words. His mind spun with the thought of every future customer walking into the salon and seeing his feminized image plastered across the walls. “But what if... what if someone I know sees them?”

Sarah shrugged “Well, I guess they’ll see just how stunning you now look.”