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🕑 Added 2024-08-02 16:57:06 +0000 UTCChapter 10: Rapunzel
On Monday morning, Tommy was jolted awake by the shrill sound of his alarm, feeling utterly exhausted. It was a strange experience to be up so early, meticulously applying makeup to ensure it was perfect for his interview. Despite the sleepiness weighing on his eyelids as he carefully blended his eyeshadow and lined his waterlines, he tried to stay positive as he prepared for the day ahead.
As Tommy stepped out of the house into the freezing morning air to catch the bus into the city, he felt a mix of anxiety and vulnerability. It was his first solo outing dressed as a girl, yet he found some comfort in knowing that on his previous trips with his sisters, he had passed without incident. He remembered Monica's advice as he tottered to the bus stop atop a pair of heels far too high for such a crucial day. She had assured him that if he carried himself with confidence and kept his head high, people would be less inclined to stare - after all, nobody likes maintaining uncomfortable eye contact in a public space. To her credit, it seemed to work. After a few initial nervous encounters, Tommy relaxed into his role as an attractive office lady, with onlookers either pretending not to notice him or quickly averting their gaze.
Everything was going smoothly until a creepy man chose to sit unnecessarily close to him on the bus, pinning Tommy against the window. With his pantyhosed legs squeezed tightly together, putting pressure on parts that a typical girl wouldn't have, Tommy felt incredibly uncomfortable. To make matters worse, the man persistently tried to engage him in conversation, which Tommy counted with the occasional one-word answer and staring intently out the window. He learned a valuable lesson that day: in the future, always sit by the aisle.
Twenty minutes later, Tommy found himself on a plush black sofa in a high-rise building in the city. Rubbing his hands up and down his silky legs, he tried to warm them after the chilly journey that had left them numb. The wait was torture as he fidgeted and fussed with the hem of his tiny shorts while strands of platinum-blonde hair filled the peripherals of his vision.
He was still adjusting to his new, ultra-girly hairstyle, with every frustrating strand that fell across his makeup-caked face serving as a reminder of his questionable life choices. Saturday afternoon had once again led him to an unwanted trip to the beauty salon, where the feminized man was forced to sit for hours while his hair was tediously dyed and extended. He had opted for this partly because he still couldn’t stomach the thought of a spray tan, and partly because his hair was already long and femininely styled, making him question what difference a change in style would make. To be fair to Sarah, she could have chosen a much more embarrassing style than the one he ended up with. That isn’t to say Tommy liked having his hair transformed into a platinum blonde mane extending to the small of his back. Especially when Sarah had chuckled afterwards, telling him his hair now matched one of her childhood dolls - a doll whose hair Tommy had once maliciously snipped off with scissors, a spiteful act from their younger days that now seemed like a lifetime ago.
Tommy's heart raced as he sat on the sofa, waiting anxiously to meet Monica's friend Claire. He readjusted his position, crossing one leg over the other and resting it above the knee - a movement he had observed many women make and one that helped him feel like he was blending in. As he shifted, the sheer black tights sliding against each other produced a soft swishing sound of nylon on nylon, echoing through the quiet office space and heightening his nerves.
Straightening up, Tommy reached to remove a strand of his sickeningly feminine hair that had adhered to his glossy red lips, feeling like a fish out of water in his feminine outfit. He regretted giving in to Monica’s suggestion to wear her blouse and blazer to the interview, but he had only himself to blame. That morning, unsure of what to wear, he had asked his sister for help. She agreed on one condition - he wasn't to complain. At the time, he had been grateful for the assistance, but now, as he felt the suffocating snugness of the silky blouse and the agony in his feet from what Monica had called "her matching Mary-Janes," he wished he had just gotten ready on his own.
"Tammy Jenkins!" a voice called out, sending shivers down Tommy's spine. "Miss Jones is ready for you!" With a deep breath, Tommy rose to his aching feet, his towering heels clicking loudly against the hardwood floor as he forced a smile toward the woman who had called his name.
(See image 10)
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"So, how did it go?" Monica asked, her eyes sparkling with curiosity as soon as Tommy stumbled through the front door. Despite her eagerness, Tommy didn't share her enthusiasm.
"Awful," he replied quietly, relieved to be home and longing to retreat to his room to rest his weary body.
"What? No way! What happened?" Monica asked with concern, taking her crossdressed brother's arm and leading him to the living room sofa.
Flopping down on the sofa, Tommy looked at Monica and took a deep breath. "Well, first I embarrassed myself in front of the receptionist by leaving my purse on the sofa. Then, I was so nervous I messed up all the questions. It was super humiliating, Mon.”
“I’m sure it wasn’t as bad as you think. These things happen,” Monica replied, trying to reassure her brother. “What did Claire say after? Can she help you out?”
"Yes," Tommy replied glumly, lowering his heavy eyelashes, “she thinks she can find me some work, but she thinks I'm a girl!" he added, his frustration showing as he balled his fingers into fists. “What if I slip up and she sees that I’m not?”
"Well, I'm not surprised if she treated you like that," Monica replied, rolling her eyes. "Have you seen yourself lately? You look like a super cute young woman! I hate to say it, but that outfit looks way better on you than it ever did on me."
"Then don't say it," Tommy replied, sounding annoyed. "I don't want to look like a cute woman. I want to look like a man!"
"Hey! Don't get all moody on me," Monica snapped. "I’m the one who spent hours helping you get ready this morning. Try to look on the bright side. Now you can finally make some money to pay the rent. After that, you can dress however you want. Oh, and don't worry about Claire. I already told her you were my brother.”
"What?!" Tommy exclaimed, his head shooting up in surprise. “Are you serious!? She called me Miss Jenkins the whole time!"
"Well, what did you expect her to call you when you look like an adorable little Barbie doll?" Sarah said, strolling into the room to join the conversation.
Tommy didn't respond, deciding it was better to hold his tongue than get into an argument when all he wanted to do was get to his room and free his throbbing feet from their high-heeled prisons.
By the end of the week, Tommy had come to terms with the fact that, for the short term at least, he would need to work as a girl. Each morning, he eagerly checked his emails, hoping that Claire from the agency would have something for him. He kept telling himself that a few weeks of work would pass quickly, and then he could return to his normal life of computer games and comfortable clothing.
The situation he found himself in was surreal and far from ideal, yet the prospect of earning money gave him hope. He hoped the forfeit he would choose that Friday evening might be the last, allowing him to leave all the "girly nonsense" behind for good. And just in time, as the options seemed to be getting worse. This week, the choices presented to him were: ‘Fill the cups of your new bras with breast forms, and tuck your member flat inside your new matching panties,’ or ‘Pierce your ears and start wearing an assortment of earrings.’
