My naturally feminine body made the transformation easy. I never had much body hair to begin with. I couldn’t grow even a moustache. My naturally long hair meant that I didn’t need a wig. A few extensions did the trick.
As a performer who had been on stage, I wasn’t unfamiliar with being dolled up. Most stages came with big TV screens that magnified your appearance. There was also a fishbowl aspect to being a performer. People just scrutinized every aspect of your physical appearance. I knew I had to be twice as careful when cross-dressing as a woman.
Thankfully, I had Nadine to help me through the more minute aspects of being a woman. For example, women had breasts and I needed to have a pair myself. My manager had the brilliant idea of using gel molds to puff up a bra.
Following her instructions, I wore the bra and filled it up with the gel molds. It was surprisingly comfortable. “Wow, this isn’t too bad…”
She giggled and poked them. They moved like the real deal. “I knew you would like them. They’re a little big but that can be a nice asset to have in this industry.”
I rolled my eyes. “Okay, what’s next?”
My manager took off the cap of a lipstick. “The fun part.”
I had to admit that learning to put on makeup was fun. I was no stranger to putting on a bit of makeup before an audition or performance. However, women’s cosmetics was a whole world onto itself.
There was so much to learn about makeup. I needed to know the right amount of lipstick to apply so that I didn’t end up looking like a prostitute. The same principle applied to eyeliner and mascara. I needed to use just enough to highlight my eyes. I was shocked when I saw my reflection. Piece by piece, Gertrude was starting to come together.
The clothing was a bit more complicated. Nadine went through her wardrobe for old clothing. She pulled out a few dresses that looked to be my size. “I used to wear this back when I was a few dress sizes smaller.”
I took an instant liking to women’s clothing. They were soft and silky to the touch. It didn’t chafe or rasp against my bare skin. It almost felt like I was wearing nothing at all.
A pair of thigh-high stockings brought out my toned legs. While I wasn’t an athlete, I did keep my body in good shape. I loved how the stockings were tight but flexible enough for me to move in.
We finished it off with a bit of jewelry. A pair of modest studs sat prominently on my ears. I was thankful for the fact that I had pierced my ears years ago in college for a bet.
The shoes, however, took a bit of time getting used to. Nadine picked out a set of pumps for me to walk around in. After a few hours of practice, I could strut across the floor like a top model.
Finally, all the pieces had come together. Gertrude was an absolute stunner. I couldn’t believe I was actually the woman in the mirror.
Nadine whistled. “Looking sharp, babe.”
I sucked in my lower lip. “Do you think people will be able to see through me?”
My manager patted me in the back. “I see you every day and it’s hard to tell that it’s really you.”
“At least singing will be easy,” I said. My natural voice sounded like that of a young woman. It would be easy to sing anything the audition threw at me. “I just have to maintain my appearance.”
It almost felt too easy. I looked at my reflection again. Gertrude was a real belladonna.
While not much had changed, the small details had brought out my laden beauty. A touch of blush made my cheeks look more pronounced. Lipstick made my lips look bee-stung like that of a supermodel.
It was funny to think of myself in this way. As Greg, I never thought of myself as some heart throb. I wasn’t manly enough to be on the cover of a Men’s Health magazine like Brad Pitt. On the other hand, I was also too pretty for an industry full of professional pretty boys.
But being Gertrude was perfect for me.
The woman’s slender body was eye-catching. That wasn’t to say that I had the right curves for the dress. With my padded bra, I filled it out nicely.
Nadine interrupted my thoughts by clearing her throat. “If you’re done admiring yourself, then we’ve still got a long road ahead of us.”
I blushed in embarrassment. “What do you have in mind?”
“You can’t go walk into an audition without a background,” she answered. “Gertrude is going to need a history and a resume. It’ll raise too much suspicion if can’t remember what you did for high school.”
“You’re right,” I admitted. I would be asked all sorts of questions during the audition process. I knew I couldn’t go on being Gertrude forever but I needed to play her well enough to fool the judges at the management. “We’ll need to come up with something believable.”
“The audition will start in a few weeks,” Nadine replied. While I might have failed as Greg, I had a leg up as Gertrude. I knew what they were looking for in their search for the next female pop idol. I could finally succeed and maybe even meet Willie Browning in person. “We don’t have too much time but we’ll need you to practice being Gertrude. You’ll need to come up and memorize her entire history.”
I giggled. “You seem excited about this.”
My manager rubbed her hands together. “I can’t wait to get my headhunting bonus from Sunstone Records.”
I rolled my eyes. At least one of this was doing it for art rather than the money. “Let’s get started.”
Chapter 3
The next few weeks were a blur. I spent each day learning how to be a woman. Nadine was there to guide me every step of the way to being an honorary member of the sisterhood.
I couldn’t just coast off of my singing ability. I needed to look the part of a popstar as well. The people at Sunstone Records would inspect everything about my appearance. I needed to be the complete package. This meant a trip down to the local spa.
It was embarrassing at first but I ended up enjoying the full spa treatment. The staff went to town on making my hair as smooth as silk. They trimmed my nails. The masseurs shaved off any offending body hair with a bit of wax. They even plucked my eyebrows. I felt like a new man.
Well, a new woman to be precise.
I practiced being Gertrude in my apartment. It was surprisingly easy disguising myself as a woman. My natural speaking voice was perfect for her. The feminine clothing I wore was more comfortable than the clothes I wore as Greg.
She felt more like a person onto herself. The woman was confident where I was sulky. As Greg, it felt like every audition was a funeral. Now, I was actually looking forward to singing in front of those notoriously harsh judges at Sunstone Records. I never felt such a burst of self-assurance before in my life.
Even Nadine agreed with my renewed confidence. “You’re going to win it hands down, Greg- I mean Gertrude.”
“It’s not like I can continue being Gertrude if a miracle happens and I actually get the contract,” I replied, admiring my makeup in the mirror. I could finally do it without Nadine’s help. “Just pulling this over Sunstone Records is enough for me. Besides, I might get one-on-one feedback from Willie Browning.”
I wasn’t stupid enough to think I had a real shot of getting a contract. It would probably go to some stuck up diva who came from a well-connected family. Besides, I couldn’t go on being Gertrude forever. What Nadine and I were doing wasn’t anything close to being legal. Sooner or later, Sunstone Records would catch onto the fact that I wasn’t exactly a woman.
Nevertheless, I focused on perfecting my act. I decided that Gertrude would be a young woman who was cocksure of herself. She didn’t have any of Greg’s insecurities. While she looked like a sweet girl, Gertrude had the confidence of a Grammy winning diva. A bit of poise never hurt in an audition.
Nadine helped me practice my act by allowing me to speak to her other clients over the phone. I posed as her assistant and spoke to people on her behalf. I could practice utilizing my new persona in a controlled environment. Some of them were friends of mine but none of them could tell it was me.
My manger wasn’t satisfied with the little experiment. She decided to kick things up a notch. “Gertrude, we’re going to go out for some karaoke. It’ll be a girl’s night out for the two of us!”
I always loved a night of karaoke. It was like flexing your muscles. I got good practice by performing in front of a crowd. “Sure let me get out of this dress-”
Nadine stopped me. “No, you’ll go as Gertrude!”
I stared back at her disbelief. “What?”
My manager smiled at me. “You need practice performing as Gertrude in front of a crowd. What better way to do it than a round of karaoke in?”
I wasn’t as convinced. “What if something goes wrong?”
She giggled. “It wouldn’t be the first time a transvestite sang on stage at the local bar. You need the experience. Come on, let’s get going.”
I couldn’t argue with her logic. My new persona needed to be battle tested. “I hope nothing goes wrong…”
When I walked outside, it felt like my skin was on fire. I felt so self-conscious of how I looked. I hadn’t worn anything too flashy. It was a simple one-piece dress that didn’t reveal much.
Despite going to the local bar, I wanted to blend into the crowd. It was an unfounded concern. No one gave me a second glance as I walked down the street. Well, that wasn’t entirely true. I got a few smiles from the men walking by us. Usually, I was completely ignored as Greg.
The attention I received only multiplied once we got to the bar. We sat at a table and ordered a couple of drinks. To my surprise, someone paid for our drinks. Nadine laughed and said. “I should bring you with me here every day.”
I shrugged. “Maybe they paid it because of you.”
My manager pointed to a man in the distance. He was staring straight at me which made my shudder. “No, that man’s trying to get under your skirt, Gertrude.”
I wasn’t as sure. “Maybe he knows I’m a guy…”
“You’re too paranoid,” Nadine said, enjoying her drink. “Just sit back and enjoy the attention.”
I listened to her words and began to relax. A few free drinks helped calm my nerves. I couldn’t remember the last time I got so many freebies at a bar.
Soon, a spot opened up on the stage for karaoke. With a shot of liquid courage, I walked up to the microphone and began singing. It came naturally to me since I had performed before the same crowd countless times before. Sure, I was a wearing a dress this time but everything else was the same.
I was an instant hit at the bar. I didn’t know what I was doing different. I sang the same pop songs in the same manner I did as Greg. I guessed looks mattered a lot when it came to my voice.
I couldn’t remember the last time I had enthralled such a crowd. They were all singing along with me. Usually, I got my fair share of jeers and heckling. Now, they were like putty in my hands. I felt like Freddie Mercury at Wembley Stadium before a mob of adoring fans.
Maybe I could actually pull this stunt off with Sunstone Records. It wasn’t like I was trying to win a contract off of them. I just wanted to prove to them that I was a great singer. If I couldn’t do it as Greg, then I’d have to do it as Gertrude. Meeting Willie Browning would be a nice bonus as well.
Gertrude was an instant hit at the bar. The men wolf-whistled at me and the women sang along with me. It felt derogatory to even think of her as a disguise. She felt like her own person.
It made me consider continuing to be her after the audition with Sunstone Records. I simply loved how people saw her. She was succeeding where Greg had failed. In any case, I would cross that bridge once I reached it.
I knew the boys here would miss the lovely Gertrude. They asked for an encore performance from me. The women, however, were a little jealous of the attention their dates were lavishing on me. I imagined I’d get a similar reception from my rivals at the audition.
When I got back home, I had renewed confidence. People had brought my new look hook, line, and sinker. I knew I had what it took to dazzle Sunstone Records. I just needed them to accept me into their next round of auditions.
It was up to Nadine to sell me to the record label. We took a few profile photos of me as Gertrude. Then, we recorded a few demo tapes of me singing various songs. I didn’t exactly have a laundry list of experience to fall back on so I had to rely on my raw talent and looks.
Thankfully, Gertrude was the type of girl they were looking for. Within hours of sending my application, Nadine told me that Sunstone Records wanted to me to come to their next audition. They even said that their top talent would be there to oversee my audition. If I got the contract, then I could receive a multi-album deal worth millions. It was a dream come true!
Or it would’ve been if I wasn’t posing as a woman. I had gotten my foot through the door but I had to be careful. The management and creative staff at Sunstone Records was a different beast than a group of drunk patrons at the local bar.
Nonetheless, I couldn’t hide my excitement. “Nadine, I did it! They’re dying to see me!”
My manager laughed at my reaction. “Save your energy for the audition. These guys are pros at what they do. We need to make sure your cover story is iron tight. At the very least, I don’t think you’ll have a hard time winning the men over.”
I blushed. “You’re right. I make one mistake and it’s all over.”
It felt like the very first time I ever got a call back. Then again, it was Gertrude’s first. I had begun to think of her as a person onto herself. She was a perfect match for what they were looking for in a pop diva.
Nadine continued to laugh. “Please, I’ve never seen you so confident before in my years of working with you.”
She was right. Rather than being terrified, I was facing my challenges head-on. Being Gertrude gave me more confidence in my singing ability. My voice may have been a liability for Greg but it was Gertrude’s weapon of choice.
I smiled at my manager. “I’m going to nail this audition.”
Chapter 4
The next few days were especially hectic. I went on a crash course with Nadine about the finer points of being a member of the fairer sex. I learned how to sit down and carry myself properly.
All of this came naturally to me. Gertrude’s singing voice was second nature to me. I could perform songs with a poise I lacked as Greg. It felt like I was stripping off my skin whenever I took off my feminine disguise.
It was why I spent as much time as Gertrude as I could. I fooled everyone we met when I went outside. Countless men asked me out on a date but I had to refuse them all.
Finally, judgment day arrived.
I couldn’t remember the last time I was so confident going into an audition. Usually, I saw rejection as an inevitable conclusion. Now, I felt like I was the heavy favorite in a season of American Idol.
If anything, I was afraid to going back to being boring old Greg after this adventure. I had gotten so used to being Gertrude. It felt like there was a spotlight on me wherever I went. It didn’t hurt that men rushed to open the door for me like a proper gentleman.
Nevertheless, my greatest challenge awaited me. The people at Sunstone Records didn’t become one of the most reputable labels in the business by signing up the first person they met. Producers like Willie Browning had a keen eye for talent. More importantly, they would know if something was off about me.
I also had to deal with scrutiny from the other aspiring singers in the lobby. The women here glared at me. For once, I started to appreciate the fact that people ignored me as Greg.
“She must be from a big talent agency. It’s an unfair advantage if you ask me.”
“I bet she had Botox. Look at those cheeks!”
I couldn’t believe what I was overhearing. A gaggle of dolled up young women were staring daggers at me. As bad as it was auditioning as Greg, it never got this catty.
It was strange being the heavy favorite in an audition for this. I didn’t come from a famous talent agency or have any experience.
However, I did know what Sunstone Records was looking for. My failure as Greg had laid the groundwork for Gertrude’s success. I wanted to nail this and show them what I was truly made of.
It helped that my renewed confidence made me look like a completely new person. Sure, clothing and makeup helped but how I acted mattered a lot. I could make a man swoon with a simple smile.
Even if I refused the offer to sign up with them, I could still do smaller gigs as Gertrude. There was no real reason to stop being her, especially if people were willing to pay to hear her. People performed under fake names and alter egos all the time. Of course, I didn’t want to count my chickens until they hatched. I needed to win the contract before I could gloat about it.
The Trans Ultra Collection Vol 3 Page 8