It helped that I had done a full makeover. I shaved off what little body hair I had. Hell, I even shaved my balls. I also applied makeup and a perfume I rather liked. The lipstick made my lips look more plump and feminine.
I spent a good hour putting on the wig. I knew it would give me away if I put it on wrong. I completed the look with a padded bra with gel molds. It gave me a respectable enough bust.
My dress fit me like a second skin. It was a blouse and mid-thigh skirt combo that looked well enough. A pair of garters connected my dark stockings to my underwear. My panties hid the bulge of my crotch well enough.
I knew I looked great.
The only question was whether or not the Scarlet Masque’s management bought it.
When I walked into the nightclub, I certainly turned a few heads. Thankfully, they were allured rather than repulsed by my appearance. I approached the waitress who I had spoken to earlier as Ben.
“You must be the one who called us about the job offering,” she said with a smile. The waitress didn’t seem to have the slightest idea who I really was. Everything was going well so far. “I didn’t quite catch your name.”
“It’s Brenda,” I said with a smile. “Thank you for having me here.”
“We’re always looking for fresh recruits,” she replied. “The job is great and I’m sure you’ll fit right in. Follow me, I’ll take you to the boss.”
I raised an eyebrow as I followed her. “He wants to see me?”
“Chase tries to interviews everyone, especially the new girls.”
She led me into Chase’s office. It was a ritzy looking place. The walls were full of sports trophies and photos with famous people. The Scarlet Masque must have made a lot of money. As for Chase, he was waiting for me in his leather chair.
He was silent for a moment as I sat cross from him. It was like he was scanning me for a reason to reject me. After closing the door, I tried to cross my legs and look as feminine as possible.
Finally, he broke the silent. “I didn’t quite catch your name. A lot of girls come into this office. I reject most of them.”
“It’s Brenda, Mr. Simmons.”
“That’s Chase,” he growled back. “I’m Mr. Simmons to my business partners. You’re new around these parts? You don’t look like you’re from around here.”
I nodded. “I moved in a few months ago. It’s why I’m looking for work here.”
“Lucky for you, I’m short on waitresses,” he said with a sigh. It seemed like we were skipping over the typical interview process. I didn’t know whether they were that desperate for staff or he saw something special in me. “We’ll put you on a trial basis. You make one mistake or get out of line, you’re out of here. Got it?”
I gulped and nodded. “Got it.”
“You’ll be given a uniform in your size,” he continued. I remembered the sexy uniforms all the waitresses wore. “More importantly, make sure you keep in shape for it.”
I knew that Chase was rather frisky for a boss. I wondered if he played around with the waitresses. I hoped he didn’t lavish any attention on me. Regardless, I had my foot past the door. I just needed to keep my head down and do a good job.
“Thank you so much!”
However, Chase was stone-faced. “Wait, there’s one more thing.”
My heart-thundered.
Had he discovered my identity?
I asked nervously. “What is it?”
He gave an uncomfortable smile. “I really like you, Brenda. But how badly do you need this job?”
I didn’t know what he was after. “I don’t understand, sir.”
“This is an easy, well-paying job,” Chase continued, still smiling. “How badly do you want it?”
I didn’t like the sound of this. However, I was crossdressing and practically committing fraud to get a job. I couldn’t stop now in spite of the bad vibes I was receiving. “I really need the job…”
Chase reached down to his crotch with his hand. “Let’s see how good your skills are. How about a blowjob for the job?”
To my shock, he unzipped his pants and pulled out his erection. It was thick and pulsated in his grasp. I knew what he was planning. Chase wanted me to suck his cock so I could get this job.
I thought about getting up and leaving. I had signed up to be a waitress, not a whore. However, I needed the money.
I had put in too much work to back off now. As strange as it was, I wasn’t too grossed out with the prospect of sucking his cock. Dressing up as a woman made it feel more natural. “Okay…”
Chase smiled and pulled his seat in closer to mine. “Good…”
I watched his cock grow harder between his legs. It was becoming monstrously long with thick veins bulging from its sides. The tip glistened with a drop of pre-cum. I wasn’t sure where to begin.
I decided to lean forward and kiss the head of his cock. Chase groaned as I ran my tongue down the soft underbelly of his shaft. I went down to his balls and kissed them. They were so much bigger than mine.
I opened my mouth to suckle his balls. Then, I reached out to cup them as I licked all the way up his shaft. When I reached the top, I kissed his wet tip.
I didn’t think of myself as a man sucking another man’s cock.
I was Brenda now and I would do anything for the job.
Chase groaned as I swallowed his cock. “Oh yes… take all of it in. Damn… you’re a good little cocksucker!”
Perhaps, I was a natural. I reached over to caress his balls as I sucked him. He looked like he was having the time of his life. The man groaned and closed his eyes as he submitted to my sucking.
From experience, I could tell he was about to go off. I felt a warm jet of cum hit the back of my throat. I nearly gagged but I held onto his cock. His rapid fire orgasm continued but I got used enough to it that I could start swallowing.
Chase kept on coming hard inside my mouth. Yet, I drank it all down. I couldn’t help but feel proud of doing the deed as Brenda.
After he finished, the man groaned as I licked his flaccid prick clean. “Oh baby, you’re the best. You’re hired!”
After that little exchange, Chase cleaned up and offered me a contract. I made sure to sign it with Brenda’s name. Finally, I handed it back to him. “Here you go.”
He smiled. “I don’t usually hire girls without a trial period. But you’re extra special.”
I blushed. “Thank you.”
Chase continued. “There is a lot of money to be made here, especially from tips. However, I do give out bonuses for good work. If you stop by my office at the end of the week for a… performance review, then I could see if you deserve a bonus for your hard work. I’m sure you wouldn’t mind an extra hundred dollars going your way.”
I would have to be an idiot not to see his innuendo. It was something I would have to keep in mind. Some extra cash for a blowjob didn’t seem so bad. “I understand.”
To my surprise, Chase slapped me on the ass and said. “Make sure your uniform fits snuggly. I like seeing a nice ass in that.”
After that episode, I went to undergo orientation with the other waitresses. They were surprised that I was hired so quickly. However, there was a staff shortage so they didn’t ask too many questions.
They gave me a uniform which I dressed into privately. It was tight and rather form-fitting. I knew I looked good in it.
All of them brought my story as Brenda. I told them I had moved here from the other side of the country. I said that I was taking night classes at the local college. There was enough of a mix of truth and lies to be believable.
I had been more worried that women would see through my disguise but these waitresses never suspected a thing. In fact, they were surprised at my waiting skills. I had worked as a waiter for years so all of this came second nature to me.
After the orientation ended, I went to my apartment and collapsed into my bed in exhaustion. It had been a crazy day. I had planned on going to the Scarlet Masque and applying fo
r a job by pretending to be a woman. Nothing about giving my would-be boss a blowjob was in that plan. Stranger still, I kind of enjoyed sucking Chase’s cock.
I thought about his other offer. If I visited him at the end of the week, he would give me extra money. I wasn’t sure if I would accept it. Chase could ask me to do kinkier things. Worse, I could risk revealing that I was a man. I needed to keep my head down and collect tips.
Yet, I was excited as hell at the idea of sucking a man’s cock. My prick was getting hard at the mere thought of it. Still dressed in my new uniform, I reached under my skirt and pulled down my panties.
My erection sprang free and brushed against my stomach. I didn’t know why I was so hard. I guessed the act of crossdressing and not getting caught had awoken something within me. It was a thrill to deceive people and not have them suspect a thing. When I looked in the mirror, I saw Brenda instead of Ben.
Nonetheless, I recollected myself and prepared to work the next day at the Scarlet Masque. I had an amazing time working at the nightclub. The customers were friendly and tipped very well. During my first night, I made nearly a thousand dollars.
I was successful beyond my wildest dreams. I never made anywhere the same amount of tips waiting tables as a man. Sure, the male guests could get a bit rowdy but I was generally treated well by them.
I still needed to come up with a cover story for why I was out all the time. I told my parents and friends I was doing work for one of my professors and getting compensated for it. It was a believable enough excuse for my absences.
As the week passed, I got used to the work. Well, I never got used to guys asking me to go out with them. I knew they planned on having sex with me. I could only smile and put them down gently. I didn’t want to upset customers who tipped well. If anyone got too physical, the bouncers would come in and tell them to take a hike.
However, there was one guy who caught my eye. He was a handsome dark-haired young man who would come have a few drinks at the bar alone. I knew a few of the other waitresses had a crush on him. With jealousy, they told me that the guy was always looking at me.
One day, I served him a drink. “Here you go.”
“My name is Jason,” he said, taking the drink. The man was just a little older than me. I guessed he was either working or studying for a post graduate degree. “Nice to meet you, Brenda.”
I smiled at him when he gave me a sizeable tip. “Thank you.”
Jason slid a business card across the table. “I work in telecommunications. If you ever want to go out and have a bite to eat, you have my number.”
I took the card. There was no way I could pursue a relationship with another man. “I’ll keep you in mind, Jason.”
I felt a little disheartened over the exchange. Jason seemed like a nice enough man compared to the men I usually met at the Scarlet Masque. However, I couldn’t risk blowing my disguise. I was just making too much money to chance it.
He wasn’t the only man I avoided. I didn’t go to Chase for a ‘performance bonus.’ It wasn’t that I was repulsed at the idea of blowing off another man. I just couldn’t risk things escalating and having him interested in fucking my ‘pussy.’
While he was upset I didn’t go see him, Chase didn’t fire me either. I was popular at the nightclub and a significant source of revenue for him. Besides, he had other girls who could entertain him. I was already making enough money so I didn’t need to worry about a bonus.
At the same time, I kept fantasizing about having sex with a man while crossdressing as Brenda. That blowjob during my interview had opened something wild inside of me. My cock would grow harder than ever before if I so much as thought about it.
I didn’t know why I wanted to suck and fuck other guys. I guessed I thought of myself as a woman when I was Brenda. It felt so natural when I put on her clothes. It felt so strange to enjoying myself as Brenda rather than simply doing it for the money.
As if to compensate, I tried to focus on my life as Ben. I tried to hang out with my friends and play sports. I even tried to date a girl but my schedule at the Scarlet Masque prevented me from spending too much time on it. More importantly, I just wasn’t interested in dating a girl.
I just didn’t enjoy being boring old Ben. Brenda was the center of attention wherever she went. People were nice to her and thought she was beautiful. I just couldn’t get the same response as Ben.
At the same time, I started a friendly relationship with Jason. He was a regular at the Masque and I couldn’t avoid him even if I wanted to. Besides, he tipped well.
In fact, the money was rolling in. I was making thousands of dollars for just waiting tables and serving drinks. It honestly felt like highway robbery.
I had to be careful since the money was off the books. I couldn’t just go around spending it wildly without attracting attention. The IRS would come after me and ask where it had come from. I couldn’t tell them I was working under the table by crossdressing as a waitress. I was probably past the limit to which the money had to be reported. I decided to deal with it later until I saved enough cash to pay for college expenses.
Over time, I learned that Jason was an executive at a nearby phone company. It was a boring job so he came to this nightclub to unwind. He seemed much more sophisticated than the other men I met.
I had to admit Jason was rather handsome. He had bright blue eyes that matched well with his thick, dark hair. The man was tall with an athletic body he got from recreational swimming. I could tell why the waitresses crushed on him so hard. Hell, I was getting a little hard for him.
Sometimes, I even forget that I was pretending to be a woman. My feminine persona had taken over my life. I knew this charade would have to come to an end one day. I had such a good time being Brenda. I didn’t want it to end.
I had many admirers other than Jason but he was the one who stood out from the crowd. He was sweet on me without being patronizing. I felt sad about constantly brushing off his polite advances. There was just no future between us.
Or so I thought.
Out of the blue, Jason asked. “Brenda, would you like to go on a date?”
I raised an eyebrow as I finished serving him a drink. “A date?”
He chuckled. “Well, I’ve tried to be subtle about this as much as possible. I guess it’s time for the direct approach.”
I wasn’t sure how to reply. I couldn’t risk Jason finding out who I really was. At the same time, I got along well with him. I had never connected to another person as well as I did with him.
“Okay, just a date,” I said. It didn’t have to be anything overly romantic. We could just be friends. At worst, Jason could lose interest in me and stop seeing me. “Nothing serious. I don’t want to get your hopes up if you’re thinking of us going steady.”
“I like you because of your company, not your looks,” Jason replied with a laugh. “Not that you don’t have a killer body.”
I blushed. “Okay, my shift will be over in ten minutes.”
Eventually, Jason and I left the Masque together. I changed out of my uniform and into my usual clothes. I wasn’t sure what the plan was for tonight. I had barely gone on any dates as Ben. This was my first date as Brenda.
Thankfully, he took charge and we visited a nice restaurant. Jason was a regular there and we got ourselves a nice table. After the waiter took our order, I said. “It’s nice having someone else take your order for once.”
Jason chuckled. “I was sure you’d appreciate having some time off.”
“This place is fancy,” I said, scanning the restaurant. It probably cost a small fortune to book a table here. “Being a telecommunications executive must have its perks.”
He leaned in. “Same with being the prettiest waitress at a night club.”
Our food arrived and we shared a delicious meal. Jason lavished me with praise over my appearance despite the fact I was haggard from a day of work and wearing my street clothing. Nonetheless, we enjoyed each other’s company.
>
When it came to dance on the restaurant’s outdoor dancefloor, I was too giddy to refuse. It was strange dancing with another man while wearing high heels. The slow tempo of the music helped me find my pace.
Jason was a complete gentleman. Yet, I couldn’t help but press my fake breasts against him. He returned the favor by cupping my ass.
Then, we kissed.
It was so sensual that I believed I was actually a woman. I had never planned on starting a serious relationship with Jason. It was doomed to failure. However, it was something I would have to deal with later. For now, I was happy to have his full attention.
The Trans Ultra Collection Vol 1 Page 13