At the very least, I could get direct feedback from Sunstone Records. This audition seemed more luxurious than the one I had done as Greg. We were deep inside the label’s offices. They were giving us the five star treatment with complimentary coffee and other treats.
Despite the extravagance, I was focused on impressing the staff here. I didn’t know whether or not Willie Browning would be listening in on my performance. In either case, I needed to do my best.
I was everything Sunstone Records was looking for in their next popstar. I was young and had raw talent. My feminine looks were a boon when auditioning to be a female singer. They could mold me into the next superstar. Of course, the fact that I was a cross-dresser complicated things.
One of staff members called out. “McKay, Alicia.”
A dainty woman sat up straight and walked into the recording booth. She had this cute girl next door look similar to Carly Rae Jepsen. Nonetheless, she looked as though she had called up for her execution. It reminded me of how I used to be.
Everyone here except me looked like they were praying to every deity in existence. So much was on the line for them. I knew that not all of them were from major talent agencies or rich families. Some of them had been struggling to make it in this competitive business like me. Winning the contract would be a dream come true for them.
A contract with Sunstone Records was a license to print money. Any struggling musician could become an overnight sensation with their backing. The best music producers in the world would work with you. They gave very generous contracts to lock in top talent. You would be set for life if you made it through their grueling audition process.
Me?
I didn’t care if I got the contract or not. Nadine wanted her headhunting bonus but I was here to prove a point. I was a born pop diva even if I needed a dress and a bit of makeup. If I couldn’t make it as Greg, then Gertrude would finish the job.
It helped that I couldn’t accept the contract. I didn’t have much to lose. It emboldened me in a way I never felt before. I was going to dazzle the judges.
That’s when one of the assistants called out my name. I gathered my water bottle and strode proudly to the recording booth. “Coming!”
Even the assistant noted my swagger as she opened the door and led me inside. “I’d wish you good luck but I don’t think you’ll need it.”
The audition was a total breeze. I sailed through every challenge they threw at me. No note was too high and no song was too sugary for me to sing.
When you came down to it, the process wasn’t all that different from the one before. Sure the recording booth was bigger but I still singing in front of a one way mirror. I didn’t know who was on the other side of the glass but I knew I had impressed them. I overheard them gushing over me through the speaker.
They seemed completely gaga for Gertrude. I couldn’t blame them since I had tailor-made this persona for them. I knew they were in search of raw talent. Of course, my skills had been honed through years of practice and stage experience but they didn’t need to know that.
I went through every song they threw at me. They were testing my nerve and stamina. I knew they wanted me to break or strain my voice. However, I had trained for weeks leading up to this moment. Mentally, I had reached a new plateau as Gertrude. I never second guessed my abilities.
I wondered if Willie Browning was on the other side of the one way mirror. The man was difficult to please. If I won him over, then I was a shoo-in to get the contract.
Soon, they tested my vocal range. I naturally had a high pitched voice so it wasn’t difficult for me to sing in female vocal ranges. I couldn’t sing in a baritone if my life depended on it but I was born to sing in soprano.
While I had fumbled before as Greg, I was nailing this audition as Gertrude. I suspected that the women before me had been a bumbling mess. The stakes were high but I was as cool as a cucumber. That went a long way in this business.
Finally, the audition came to a close. I immediately knew that I was the top of the pile. “Thank you for coming, Gertrude. We’ve loved having you here.”
I wanted to celebrate but I decided to play the role of the humble singer. “No problem. Thanks for having me. I’ve been a fan of your music label for years.”
“Just wait a moment before security escorts you upstairs.”
That wiped the smirk off of my face. “Security?”
Before I could process what was even going on, a tall security guard walked into the room and said. “Come with me.”
Chapter 5
I came crashing down to earth.
I didn’t know how they had caught me. Every part of my performance had been immaculate. They even said that they loved my audition. Nonetheless, the security guard stood before me like a statue.
I tried to hide the sense of panic I felt. “Excuse me?”
Looking a bit impatient, the man repeated his instructions again. “Please follow me.”
I figured this would go easier if I didn’t try to fight. “Okay…”
Making a turn down the hall, I followed him to the elevator. I didn’t know how I had let my real identity slip. None of Sunstone Records’ employees seemed to have noticed anything odd about me. In fact, they seemed to think I was perfect for the role.
I wondered what they would do to me. I could end up in prison for committing fraud. I hoped Nadine didn’t end up in trouble as well.
Maybe I was overthinking it. Perhaps, they liked my performance but noticed a discrepancy with my paperwork. We had spent a couple of weeks coming up with a cover story. Chances were that there were a few mistakes in there. I could probably come up with an elegant excuse and get myself the hell out of here.
We rode up the elevator to the buildings apex. That was where the executive offices were kept. I didn’t know why we were going up if I was in trouble. If anything, I figured they rough me up for lying and dump in the back with the garbage.
Nonetheless, the doors opened and revealed the clean look of the executive offices. I didn’t have time to soak in the sights. The security was strict here but the man got the front desk to wave us in. This place was locked up tighter than Fort Knox. I knew Sunstone Records tried to protect their trade secrets but this was ridiculous.
Finally, the security guard led me to a nice corner office and knocked on the door.
A voice spoke through the closed door. “Enter.”
The guard opened the door and ushered us in. A man nearing middle age sat in a leather office chair. His three piece suit was custom tailored to his tall frame. He looked up from the Yamaha keyboard he was fiddling with to look straight at me.
It was Willie Browning.
He commanded the guard. “Leave us.”
The guard bowed as if the man was royalty. Maybe Willie was king in this office. “Yes sir.”
He shut the door closed and left me alone with Willie. I couldn’t believe I was face to face with my idol. The man had written and composed so many of my favorite songs. Like an idiot, I stuttered. “Y-your Willie Browning!”
“And you must be Gertrude,” he chuckled at my childish reaction. I immediately turned flush with embarrassment. “I’ve heard so many… interesting things about you.”
I didn’t know if this was an interrogation or an interview. I figured the big man himself wouldn’t be meeting with me if I had been caught. “You’ve heard about me?”
“This is the twenty-first century,” he said, pointing to his computer monitor. “We have live streaming. I saw everything from my office. You’re a very talented young woman. I don’t make that statement lightly.”
I nearly did a double-take from what I was hearing. A multiple Grammy winning composer was praising me. Stranger still, he actually seemed to believe that I was a woman. I didn’t know whether to jump up for joy or recoil in fear. I decided to play it safe and consider this another test. “What did you hear about me?”
Willie chuckled at my show of backbone. I could tell that
most singers swooned before a man of his stature. “We put you through the ringer but you still stood firm. Most women would break before the end.”
“I’m not like most women,” I replied, sounding believable. It helped that my statement was true. Nonetheless, it made Willie lean forward in interest. Playing hard to get only seemed to make him more fascinated by me. “Are you telling me that no one else caught your eye?”
I needed to get out of here. I hadn’t planned far enough to think of a way to bluff Willie. However, my defiance only seemed to intrigue me. “Gertrude, I figured you would be dying to work with me. It’s not very often a novice gets brought up to my office.”
I sucked in my lower lip as I thought about a response. “Maybe I don’t feel challenged enough at Sunstone Records.
That got a laugh out of Willie. “I like women who take the initiative. It beats working with someone who is just after a nice contract.”
I looked pensive. “So do I get the contract?”
It wasn’t like I could pretend to be Gertrude for years on end. Someone at Sunstone Records could catch on. Nonetheless, I had to look somewhat interested in the contract to avoid arousing his suspicion.
“The audition process isn’t over,” Willie stated. It explained why he had brought me up to his office. He wanted a one-on-one interview with me. “You need to pass the final test. Get up and stand before me.”
That sounded simple enough. I nodded and said. “Okay.”
The moment I got in front of him, the man grabbed my breasts from behind. “Now, breathe.”
I gasped when I felt his hands on me. Thankfully, my gel padded bra felt believable enough for him. Nevertheless, I was completely shocked. “Mr. Browning!”
Glancing over my shoulder, I saw that the man looked completely serious. “I need to know what you’re capable of Gertrude.”
I wanted to flee from his office. If Willie got too close to me, then he could find out that I was a woman. I could end up in prison or the insane asylum. At the same time, it would look too suspicious if I made a quick escape. There was a lucrative contract awaiting me.
I decided to play around for now. With his instructions, I did a few breathing exercises. I felt his hands knead my fake breasts every time I exhaled. I guessed he wanted to know my lung capacity.
Nonetheless, the man didn’t seem satisfied. “All this clothing is constricting your natural talents.”
Before I knew what was happening, Willie began unbuttoning my clothes.
“Wait!” I yelled, trying to stall for time. I figured it would go better if I did the deed. It was better than having him take off my panties. “I’ll do it.”
Taking the initiative, I began stripping off down to my undergarments. Willie watched with a smile on his face. I didn’t know whether it was my body or my singing talent that attract him to me. In any case, he didn’t have the slightest clue that I was a man.
Normally, I would’ve been terrified to strip before Willie. Now, I felt a strange calmness as I took off my clothing. Gertrude was fearless compared to Greg. She could stare down a top producer without batting an eyelash.
It felt odd to be the center of a man’s attention. As Greg, I had passed over more times than I could’ve counted. Some companies took one look at my resume and rejected me. Nadine usually had to hype me up in order to get me work.
Finally, I stripped down to my bra and panties. The bra hid the gel padding underneath well enough. Likewise, the cut of my panties reduced the bulge of my cock. Nevertheless, I knew one small mistake could unravel everything.
I wondered if Willie would do the same exercises again with me. I got my answer when he eyed me from head to toe. He was practically drinking in the sight of my bare skin. The man was interested in more than just my singing ability.
With his breath hot upon my cheek, I felt his cool fingertips explore the contours of my body. His hand stopped at my bra and gave it a squeeze. If I ever got out of this, I really had to remember to thank Nadine for her ingenious idea about the gel molds.
I felt his finger go down my abdomen. My heart thundered as he approached my groin. I knew his eager hands wanted to go inside my panties. It didn’t help but my cock was getting hard for some reason. I started panicking when a finger dug under the waistband.
Letting my instincts take over, I leaned forward and kissed Willie. That stopped his hands from probing further. It was a sensual kiss that left my lips burning. The music producer seemed to be utterly enthralled by me.
I didn’t know why I was enjoying this so much. An erection was forming underneath my panties. Perhaps, being Gertrude for so long had made me think of myself as a woman. I dressed and sang like a woman. Making love like a woman wasn’t too much of a step up.
It almost felt like an audition. I had to embrace my new persona if I wanted to get out of this. I knew I was winning Willie over. The man’s stern expression had softened from my kiss.
We held each other as he whispered. “I want to fuck you.”
An exhibition streak overwhelmed me as I whispered back. “Fuck me.”
We kissed again. This time, there was an animalistic desire in both of us. Our tongues wrestled. Our lips smacked. I didn’t mind the slightest bit that I was making out with another man. His lips were just as soft and passionate as that of a woman.
I felt the desire and vitality in his body. Willie wanted to fuck me senseless with his prick. Of course, I didn’t have a cunt for him to stick his prick in.
Finally, he broke the kiss and cupped my ass. “You have a great ass, Gertrude.”
I felt my ass bubble up in between his fingers. That gave me an idea. If he couldn’t fuck my non-existent pussy, then I had something else for him. “You want to fuck my ass?”
Willie didn’t need to be told twice. He immediately began undressing as I thought of a way to make this work. Soon, the man’s lengthy shaft came into view. A patch of hair crowned the base of his prick. It wasn’t fully erect but it was utterly massive compared to mine.
Speaking of which, I was getting hard as well. My erection was painfully stiff. It threatened to burst out my panties. I knew had to take charge before he found out about it.
I leaned over the chair and pointed my ass at him. Then, I carefully pulled down my panties while carefully hiding my cock and balls. I pressed my thighs together to prevent them from slipping back out. “Fuck me!”
Willie took the bait and guided his cock towards the rosebud of my ass. He pressed the head of his shaft against it so I could get used to it. I felt my ass open up from his teasing. Finally, he slowly entered me with his massive prick.
I gasped in utter surprise. “Oh Willie…”
He began to steadily fuck my ass. I focused on keeping my balls hidden as he railed me. It was difficult due to the sheer force of his thrusting motions.
My erection began to make a tent in my panties. I couldn’t remember the last time I had gotten so hard. Something about dressing up as a woman and getting fucked by a man was pushing all the right buttons. Thankfully, Willie was too busy drilling into me to notice.
His shaft probed deep inside of me. My ass had strictly been a one way street until now. Willie was touching parts of me that I didn’t even know had existed. We were both growing unbelievably hard from this. In fact, I knew I would come at any moment.
Willie began long, slow thrusts that buried his cock to the hilt. I almost felt like I was being split in two. The man was pushing me to my limits.
Soon, the pain I felt was replaced by pleasure. All of my senses were going haywire. It was like a supernova was erupting in my body. I was enjoying this more than I had any right to.
My erection felt trapped in my panties. It was like a rocket about to go off. Willie wasn’t too far from his climax. I sensed him grunt as his thrusts grew more ragged. His balls slapped against my ass as he struggled to hold onto me.
Finally, Willie erupted inside of me and yelled. “I’m going to cum!”
I
saw him closed his eyes and go into autopilot as his cock unleashed its payload. I felt a warm splash of cum coated my insides. His pelvis ground against mine as he broke out into a series of frantic thrusts.
I came as well inside my panties. My cock grew firm as a concrete pillar and let loose a stream of semen. The strange and explicit nature of the situation had primed me to blow. It was an earth-shattering orgasm I had never experienced before.
Finally, Willie collapsed on the floor in exhaustion and gathered his breath. “What a fuck!”
It gave me time to dress and hide my erection. Willie dressed as well and sat back in his chair. You wouldn’t have been able to tell that he had fucked me six ways to Sunday.
“Gertrude, not many women are able to impress me,” he said with an affectionate smile. The man didn’t know he had been fucking a man. Then again, maybe my ass was just that amazing. “However, your various… talents have convinced me you’re the woman for the job. Congratulations, you’ve won the contract. Welcome to Sunstone Records.”
The Trans Ultra Collection Vol 3 Page 9