The Trans Ultra Collection Vol 2

by Ursula Lovelace

  Being a comedian was hard. More often than not, the joke was on you. It wasn’t telling the good joke that was the hard part. It was trying to get on stage in the first place.

  Everyone always told me that I was a funny man. I could tell jokes about everything from politicians to pineapples. It always seemed like a nice enough gig to support yourself. Everyone needed a laugh from time to time, right?

  Unfortunately, no one told me the joke about supply and demand. There were plenty of comedians in town. All of us fought for a gig since there were just so many spots to go around. If you knew the guy who owned a club or bar, then you had a leg up over the competition.

  It was awful for a guy like me who had just moved into town. Whenever I got up on stage, people loved my performance. However, I would have to wait months for the opportunity. Even then, it didn’t pay very much. I had to juggle a few odd jobs to stay afloat.

  I remembered that bar manager’s words about female comedians. Women were a rare breed in the world of comedy. Many establishments were trying to appeal to a wider clientele by hiring women for their standup comedy segments.

  The comedy world was a close-knit one and I had heard that female comedians were in high demand. They were compensated with better pay than their male counterparts. Bouncers were there to block hecklers from disturbing the performance. Some of them ended up with large fan followings on social media. I couldn’t help but be jealous.

  Women got the royal treatment while I got royally screwed. I believed a good joke was a good joke. It didn’t matter who it came from as long as it funny. I guessed who it came from and how it was told mattered to audiences.

  Comedians tended to gossip like old ladies. We shared trade secrets and rumors like it was knitting advice. I knew that women had preferential treatment when it came to landing gigs. They got spots in some of the nicer establishments in the city. They didn’t have to worry about performing at a seedy bar with an illegal firearms deal going on in the back.

  Hell, I knew a few women who worked as stand-up comedians full time. They had a steady stream of jobs heading their way. They didn’t have to live hand to mouth like a guy like me. These women even had fan clubs and sold merchandise like they were Jerry Seinfeld.

  I knew there was no point in being jealous but I was. These girls were living the dream. They were telling jokes and earning big bucks for it. I wished I could quit my stupid odd-jobs and work full time as a comedian.

  Working gigs at small comedy clubs didn’t pay the bills. I spent more time cleaning tables or walking dogs than coming up with new material. Being a comedian had always been my dream. I loved getting in front of people and winning them over with my jokes. The paycheck wasn’t as important as fulfilling my dream.

  I truly felt like myself when I made a crowd of strangers laugh. I loved putting smiles on their faces. I enjoyed making them laugh so hard that it felt like their rib cages were bending. It made the boredom of my odd jobs more tolerable.

  People loved my material. I could meet a complete stranger in an elevator and make him laugh. When waiting tables, some of the guests even said I should’ve been a comedian instead of a waiter.

  If only they knew the truth.

  I knew I couldn’t support my career as a comedian indefinitely. Working on stage took time away from my other jobs. Between practice and travel, I was barely breaking even on these gigs.

  I was spending more time as a waiter than as a comedian. Rather than telling jokes to crowds from a stage, I was down there serving drinks to crowds. Whenever I looked up, I saw a comedian making the crowd laugh with his lame jokes. I had way better material.

  I knew that clubs gave female comedians the royal treatment. They tended to attract more people. This meant they got a better cut of ticket sales and other bonuses.

  Funny as it was, one of my skits involved the fact that I would get mistaken for a woman. Between my lean curves and smooth face, people accidentally believed I was actually a woman. I couldn’t recall the number of times a guy had hit on me at a bar.

  That last bit always got a laugh out of the crowd.

  People used my appearance to make fun of me but I didn’t mind. As a comedian, you needed to know how to take a joke at your expense. That was how you became better at telling jokes.

  I made my appearance into my armor. I didn’t need to be ashamed of how I looked. Hell, I could talk like a woman if I raised my voice by an octave. That never failed to thrill an audience.

  One day, I practiced my feminine voice for a joke and had a complete revelation.

  I didn’t need to be jealous of those female comedians if I became one of them. Clubs, bars, and other establishments were on the lookout for up-and-coming women. If they were as well paid as I was told, then I could find steady work as a comedian.

  I was coming up with a new skit involving my woman’s voice. It involved role-playing as a woman named Megan. Now, I didn’t just have to speak as her. I could pretend to be Megan as my new identity by dressing up as a woman.

  Admittedly, this was on the less than legal side of things. I could land in a lot of hot water for this stunt. However, I knew that the registration process for comedians wasn’t strict. I could make up a fake background for Megan. If anything, I needed to make sure Megan’s material was up to snuff. She needed to make the audience laugh to keep her job.

  As outlandish as this idea sounded, I couldn’t stop thinking about it. I tried to get it out of my system by thinking about the holes in my plan. Yet, it only seemed to embolden me. I kept hearing from clubs requesting referrals for female comedians.

  That’s when I knew I had to do this. I began by making up a profile for Megan that seemed believable enough. She was a novice comedian who had an innate talent for telling jokes. Then, I went on to purchase clothes.

  On stage, I needed to look like a woman. It wasn’t the first time I had dressed up as a woman. In my early days as a comedian, I dressed up in drag for a laugh in college.

  When I wore a dress again, I was shocked at how comfortable it felt. It didn’t feel like I was cross-dressing for a gag. This felt so natural. The soft fabrics were like a second skin. It sure beat my t-shirt and khakis combo any day of the week.

  I had to admit I looked pretty damn good in a dress. Most men’s clothing was way too big for my frame. These lady clothes fit me like a glove. Well, the glove parts more so than the rest. I even ordered some extensions to give my already long hair some flow.

  Having been before a crowd in the past, I knew they would scrutinize every inch of my appearance. That was why I needed a padded bra to help improve the illusion. The audience needed to believe I was a real woman in order to enjoy my jokes.

  Next, I took care of my makeup. I actually had some experience putting on makeup. Even male comedians dolled themselves up a little when they got on stage. I even learned what types of makeup worked best under stage lighting. Believe me, you didn’t want your makeup to melt and land on your feet!

  Still, I was new to doing my nails and putting on lipstick. After a few failed attempts, I eventually got the hang of it. A bit of blush and eye shadow really brought out the softness of my face. You could hardly tell it was me. I’d go as far as to say that I looked kind of cute.

  When you combined my new look with my feminine voice, you had a complete transformation. I could barely recognize myself in the mirror. Strangely enough, I felt more comfortable as Megan than as Mark. It felt less like cross-dressing and more like putting on a favorite outfit.

  Perhaps, being a woman was filling me with confidence. I had a real opportunity to be a successful comedian. I just needed to seize it.

  Chapter 2

  Of course, I was putting my entire career on the line. It would take just one person seeing through my disguise to end everything. I could end up banned from performing at practically every club in the city. Worse, I could wind up behind bars. Nevertheless, I needed to test my new persona.

  I decided to meet with Jim as
Megan. The man was looking to have more female comedians at his establishment. Besides, he had already seen me as Mark. If anyone could see through my disguise, then it would be him. In case someone figured out who I was, I would rather it happen in his office than on stage. I could always back off and say this was a new skit I was testing.

  Finally, I called up Jim and introduced myself as a friend of Mark. He was immediately interested in me. In fact, he was willing to book an opening for me tonight if I met with him in person. I was in the running.

  My voice had held up but my appearance needed to pass as well. I met with Jim in his office above the bar. This would be Megan’s real test.

  To my shock, the man immediately bought my appearance. “You must be Megan. It’s a pleasure to meet you! I don’t know why Mark never mentioned you earlier.”

  I giggled. “He must be trying to hog up all the work for himself. You said you had something for me?”

  “Yes, something just opened up,” Jim said gleefully. The man was tripping over himself to give me work. “Will you be ready to perform in a couple of hours? One of our acts cancelled her booking at the last minute. We could really use someone like you to fill that slot.”

  “Of course,” I replied with a smile. “I hope they’ll like my material.”

  Jim smiled back. “I’m sure they will.”

  While I waited for my slot to come up, I thought about how easy it had been to land a comedy gig. Most newbie comedians needed references to even get their foot through the door. As Mark, I often had to audition against other comedians to secure a slot. I was shocked at how an opportunity just fallen onto Megan’s lap.

  As I prepared for my performance, I made small-talk with the bar’s stage crew. All of them believed I was a woman. A few of the men even asked for my phone number. I couldn’t remember the last time I got such treatment.

  Eventually, if came time to mount the stage. For the first time in years, I got stage jitters. It wasn’t like I was new to performing in front of a large crowd.

  I was just new to performing as a woman.

  Nevertheless, it time to get this show on the road. I had prepared my material just the same way I did as Mark. I hoped it worked as well when said by a woman instead of a man. The announcers introduced me like I was a wrestler. “This lady is young but feisty. She’ll make you laugh and pay for it. Give a warm welcome to Megan!”

  A lukewarm set of applause followed as I walked on stage. They gave me strange looks as I took the mic. I could immediately tell that this was a tough crowd. I needed to use my best material to win them over.

  “I always love a new crowd,” I said with a bright smile. “I recognize a few of you from alcoholics anonymous. I don’t think any one of you are going to win a token at the next meeting.”

  That got a chuckle out of them.

  “Do you know what’s the difference between you guys and this bar’s stockroom?” I asked, priming them up. I glanced at the bartender for good measure. “That stockroom holds less liquor!”

  The audience erupted into laughter. After that, it was smooth sailing. I went from joke to joke and had them all laughing their lungs out. None of them heckled me or acted obnoxious. I guessed Jim and the bouncers screened out anyone too troublesome.

  I didn’t understand why my material was so effective. It was the same stuff I said as Mark. I guessed it who was saying them that mattered more. The audience was in love with Megan, especially the guys.

  Some of the men wolf-whistled at me when I told a sexy joke. Their dates didn’t appreciate the attention lavished upon me. These women were beautiful but I had the combination being attractive and funny. No one could resist that.

  After that successful showing, Jim signed me up to be a regular performer. Plenty of other places were interested in me as well. It turned out that someone in the crowd had recorded my performance. I was going viral.

  It helped that I wasn’t like other female comedians. I didn’t drone on about my period or anything like that. Hell, I didn’t know anything about a woman’s bodily functions. I just used the same material I said as Mark. This time, it was a woman telling the same jokes.

  I was contacted by some pretty ritzy places. They wanted me to perform at their fine establishments. After struggling to land a gig in seedy bars, it was nice to work in an air-conditioned four star hotel. The crowds there were less rowdy. The management even offered to have a limousine drive me around. I didn’t have to work odd jobs to keep a roof over my head any longer.

  I was moving on up to bigger and better things. My audience got richer and richer. This meant the payout was bigger and bigger. It wasn’t long before I was negotiating with people over my cut of the ticket sales. Indeed, I was becoming that big of a draw.

  I decided that Megan needed to treat herself to a girl’s night out. If she was going to tell jokes to an upscale audience, then she needed to look a little upscale herself. I splurged a bit on a new dress and fancy jewelry. It had a hefty price tag but I could afford it now.

  My legend grew and grew. Megan had an unofficial fan club that was huge on social media. Many considered her to be the hottest comedian in town. That wasn’t exactly a hard contest to win. Nevertheless, it was strange that a fake persona had such a fanatical following.

  I found out that I liked being Megan outside of the spotlight as well. I loved wearing women’s clothing. I especially loved slipping on a set of new lingerie. They felt so soft and silky smooth against my skin.

  My sex appeal was one of the reasons I had such a huge fan following. Sure, my jokes were great but people came for the whole package. A bit of eye candy never hurt a performance.

  After years of struggling for work, the tables had turned. Everyone was asking for Megan. I could actually pick and choose when and with who I wanted to work. I preferred nice hotels and other upscale venues. They didn’t need to be too fancy. I just needed a place where I could relax and do my routine in a nice environment.

  While I turned down most offers, I did take jobs that intrigued me. I got one such offer from a hotel chain called Grey Hotels. Apparently, it was a luxury brand reserved for the rich and well to-do.

  “Hello, this is Megan,” I answered, cradling the phone against my ear. “I got your message. You want to book a show?”

  The man on the other line answered. “Yes, Mr. Damian Grey would like to see you.”

  Even though the man couldn’t see me, I raised an eyebrow. “Damian Grey?”

  “He’s the owner of our esteemed hotel chain,” he said with pride. Having only recently moved up a tax bracket, I was ignorant of the rich and powerful men in the area. “He wants a private booking. Mr. Grey is a big fan of your work and is eager to see you again.”

  I had fans in high places. “Really? Then let me thank Mr. Grey in person.”

  “I’ll have a limousine ready for you.”

  This sounded serious. The last time I gave a performance to a private audience was when I did a mock run through of a skit for my parents. If the guy was as rich as I was led to believe, then I would set for life.

  Chapter 3

  I learned the Mr. Grey had been a huge fan of me ever since he saw the viral video of my first performance. It sounded less like a private comedy session and more like a date. I guessed I’d have to let him down gently if he came onto me.

  Nonetheless, I dressed to impress that night. I went to a private spa to freshen up before dressing up as Megan again. I had picked up an elegant one piece dress that showed a bit of leg. A new set of black heels worked well with my dress. It was strange having more clothes than I knew what to do with. A year ago, I was struggling to make rent.

  I wasn’t sure what Damian Grey had in plan. Regardless, I waited for the limousine to arrive and take me to him. What I didn’t expect was that he would be in the limo to begin with.

  Like a movie star, the young hotel magnate stepped out of the limo and greeted me. “You must be Megan.”

  I nearly stammered. “
P-pleased to meet you, Mr. Grey.”

  “Call me Damian,” he replied, flashing a smile at me. I wasn’t the only one dolled up for the night. Damian wore a designer three piece suit. His handsome face was clean-shaven as if he was posing for the cover of a men’s magazine. “Please, have a seat. You are the guest of honor for the night.”

  I immediately knew I liked the man. For a billionaire hotel tycoon, the man was humble and down to earth. I never expected someone like him to be a fanboy of my work. It was a good thing that good comedy didn’t discriminate by your annual income.

  “Thank you for having me Damian,” I said, enjoying myself in the rear seat of the luxurious limo. It had everything from a television to a wine cooler. “I didn’t expect a man like you would like listening to my jokes.”