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My Big Break- Part 2
By RogerGirl

 It wasn't long before the success of Tiffany led us to bigger and more high profile events.  While in the beginning we primarily covered local businesses, one day we got a call to cover the opening of a new nightclub.  We were even sent press passes for the event.  Also, by this time we had switched to a new website that focused primarily on Tiffany and my friends took behind the scenes roles.  The rest of the guys went to Mara for makeovers hoping that they too could capture the success I had found as Tiffany.  Unfortunately, Doug and Eddie did not look very good as women.  Jonas, however, made a very attractive woman, and thus Joanna was born.  While the character of Tiffany was built around her sex appeal, Jonas took Joanna in a different direction.  After playing around with a few ideas, Joanna soon became the cute girl next door type.  Basically, she was the Mary-Ann to my Ginger for you "Gilligan's Island" fans out there.  With Tiffany's popularity increasing, my schedule was becoming busier so Joanna took on some of my work load.    

 We reworked the site to introduce Joanna to our visitors and the character quickly took off.  While Tiffany remained more popular, Joanna quickly built up a legion of fans who enjoyed her sweet, innocent, although very sexy, persona.  While I often had to play up my sexuality as Tiffany, Joanna came off as sexy by presenting herself as cute and playful.  As Tiffany I often wore short dresses and heels to look more adult.  Joanna, on the other hand, dressed primarily in short shorts and skirts and various costumes.  She also had a higher more childlike voice and would at times lick giant lollipops and popsicles.  That is not to say Jonas couldn't play Joanna more like Tiffany if he wanted to.  At times he would step up the sex appeal and take on a more mature voice and persona.  

 Eddie worked as something of an agent building contacts and organizing our interviews and working as a second cameraman while Doug primarily shot and edited the footage.  The website was making us money and we were even able to move into a bigger apartment.  It also allowed me to quit my day job and focus more time on the website.  Jonas also quit his job and began spending more time as Joanna.  While Tiffany was only a character I played for the website, Jonas found that he enjoyed dressing as a woman more than he had expected.  He had soon grown out his hair and built up his own personal female wardrobe.  While he didn't dress as a woman full-time, he would occasionally spend the day as Joanna and even go shopping with his girlfriend, who seemed to enjoy his feminine side.  The Joanna he played off-screen, however, behaved less like a character and more like a real woman.  

 On the night of the club opening, I arrived at the entrance wearing a sexy new mini-dress that Mara had ordered specifically for me.  She was in charge of transforming me into Tiffany and had set aside my own personal wardrobe full of sexy clothes and shoes.  I had worked on my character quite a bit, perfecting my voice and movements and making Tiffany as naturally feminine as possible.  I never tried to hide the fact that I was male, but I always did my best to present myself as a woman.  Unfortunately, Eddie and Jonas were unable to attend tonight since Joanna was busy at the opening of a 50's themed diner.  Jonas was really excited for the event and was looking forward to getting to spend the night as a cute waitress.      

 As I stood outside the club, I fell into a daze as I found myself in the company of my favorite celebrities, singers, and athletes.  Of course, this was no time to turn into a fan and I tried to act as professionally as possible.  Tiffany had become something of an internet celebrity, and many of the guests recognized me and took the time to let me interview them.  Meeting some of my favorite actresses was a dream come true.  The only drawback was I was dressed as a woman.  

 After several interviews, I interviewed the club owner and he called someone over to give me a tour of the club.  Being the club opening he was too busy to give me the tour himself.  That's when I saw her.  She was gorgeous and carried herself with an air of confidence that I loved to see in a woman.  Like the other women at the club, she was wearing a sexy blue mini-dress and a pair of 5" heels.  

"This is Gwen," the owner Michael said, "She will lead you on a tour of the club."

 Gwen smiled at me and I found myself momentarily speechless.  This wasn't the first time I had been around an attractive girl, but there was something different about Gwen.  It wasn't just the way she looked, there was a sort of spark.  I tried my best to stay in character as she led me through the club.  She took me to the bar where we ordered some signature drinks, then to the dance floor where we danced to a couple songs.  Finally we finished the tour in the VIP room and I gave my signature Tiffany sign off.  Gwen went back to her duties and Doug and I were invited to spend the rest of the night enjoying the club.  Doug took off and hooked up with some chicks, but being stuck as Tiffany my night was a little different.  I got hit on by quite a few guys and the girls were only interested in dancing with me.  

 At the end of the night, the club began to empty out and I waited at the bar for Doug to take me home.  As I finished my drink, Gwen came over to the bar and sat down by me.  

"I'm am exhausted," she said, "I don't know how long I am going to last working here.  The music is so loud and I'm constantly getting hit on.  These shoes are even worse."

"Why don't you find another job?" I asked.

"Nah," she said, "As much as I hate about it, I love being here.  I'm trying to become an actress and I'm hoping I can get my break working here."

"Well, if it's any consolation," I stated, "I think you would make a great actress."

"Thanks," she replied, "I've seen your videos, you're pretty cute as a guy too.  Too bad you're gay."

"I'm straight," I said defensively, "I have nothing against gay people though.  I have friends that are gay, but I'm straight.  This is just something I do for the interviews.  I don't dress like this at home."

"Well, in that case," Gwen said lighting up, "Maybe you'd like to take me out sometime.  I'd expect you to take me out as Tim though, I don't date women.  Especially women who look hotter than I do."

 She entered her number in my phone and walked away.  I just sat in silence as Doug came over to see Gwen walking away.  

"Damn," Doug said, "Even as a chick you get hotter girls than we do."

 We both laughed and he took me back to Mara's to change back.  When I was back to Tim, we stopped for a bite to eat before heading home.  I called Gwen the next day and we made plans to go out the following week.  With the opening of the club, she was busy all this week.  Now that I wasn't working, I had a lot more free time between jobs.  I didn't plan to play Tiffany forever, and tried finding jobs as Tim.  Unfortunately, Tim just wasn't in as high demand as Tiffany.  

 Finally, the night of my date had arrived.  It had been a while since I had been on a date, so I was feeling pretty nervous.  I showed up at Gwen's apartment in a dress shirt and black pants and was met by Gwen, who was looking as gorgeous as ever.

"Well, it's nice to meet the real you," Gwen said with a smirk, "I'm a little jealous of how you can look so good as a guy and a girl."

 We laughed and I took her out to a local restaurant I had profiled as Tiffany.  The owner knew me, even as Tim, and was happy to accommodate us despite the crowd.  As it turned out, my profiles had not just been good for me and my friends, it was good for the businesses we profiled as well.  The owner was more than grateful for his rise in success and wanted to make our night as special as possible.  I almost felt like I was in that scene from Goodfellas where the main character takes his girlfriend out for the first time.  

 As the evening went on, I found out Gwen and I had quite a bit in common.  We both enjoyed the same kinds of movies and TV shows, were fans of the same sports teams, and had attended the same college.  At the end of the night, I took her home and she gave me a short kiss at the door.  She was a lady after all and wasn't the type to have sex with a guy on a first date.  

"Call me," she said as she went inside, "Oh, and by the way.  I'd love to borrow that dress you were wearing the other night."

 We both laughed and I went home feeling better than ever.  Over the course of the next few weeks, we went out several more times.  Eventually, we were dating full time and after dating a while, I moved out of the apartment I was sharing with my friends and moved in with Gwen.  Jonas had also moved out of the apartment a few months earlier and was living with his girlfriend Bridgett.  While Bridgett and Jonas often shared clothes and spent a lot of time together as women, Gwen and I were much more keen on my keeping Tiffany at work.  It wasn't that Gwen had anything against my dressing as a woman, she would often borrow some of Tiffany's dresses and lend me some of her own to use for my interviews, it was more that neither of us had any interest in making Tiffany more than a character I played.  

 By this time, Gwen had gotten several additions and even had a few bit parts on some popular TV shows.  Most of them involved her playing a corpse, but she enjoyed the exposure nonetheless.  I too was finding even more success as Tiffany and was soon covering more club and bar openings and local concerts and events.  In a couple years, I was no longer just working in Los Angeles, and had been invited to travel to bigger events.  It was also around this time that I first appeared on television when I got a call to do a few correspondent pieces for Jimmy Kimmel.
Tiffany's profile has taken off and soon is being requested for more high profile events.  This leads to the creation of Joanna when Tiffany's schedule becomes to busy and Jonas is forced to pick up some of the slack.  It is also around this time that Tim meets his future wife while covering an event as Tiffany.  
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January 20, 2014


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