“I need coffee,” I said. And then a large cup of café coffee was thrust into my hand. “It’s black—the way you like it,” said a short, nerdy looking assistant. The same assistant had my shoes and coat out for me, and he’d even gone through the trouble of locating my apartment keys, my wallet, and my phone, which was fully charged even though I’d forgotten to plug it in after my show. As much as I hated having that crew tailing me constantly, it was nice having my own little assistant.
The shuttle was nice: a big, black Mercedes Benz that could seat me and the entire crew, with a few seats to spare. The driver had some calming music on, which would have put me right back to sleep if it wasn’t for that nagging curiosity at the front of my mind.
The forty-five minute drive ended at a large warehouse in a district filled with large warehouses. A man in a black coat opened a large gate to let the shuttle in, and then we drove around to a large, empty parking lot. The crew hopped out quickly and got their cameras aimed at me, to document my walk from the shuttle to the studio. I was getting used to ignoring them—mainly just because they annoyed me so much, so the only way to keep myself calm was to ignore them.
As soon as I passed through the door, a little makeup girl waved me over. “We need to get you into hair and makeup,” she said. “Follow me, please.” I took another long sip from my coffee and then I followed the girl. She took me to a small room with a big, bright mirror, and then she started messing around with my hair and brushing powder on my face. I had to hold my breath at points, so I wouldn’t inhale the thick plumes of powder in the air.
The cameras continued to whiz around me, even when I was just sitting and having my hair poked and repositioned. I couldn’t imagine they were getting very much in terms of useful footage, but that was their problem—not mine.
The clipboard man came into the room. “Is he ready? The girls are all ready and the producers want to start shooting.”
“He’s as ready as he’s going to get,” the makeup girl said. “His hair just isn’t participating.”
“Well we don’t have time. He’ll just have to look like that,” said the clipboard man. I looked in the mirror and felt confused—my hair didn’t look any different than it normally looked. Was that no good?
I followed the clipboard man down a series of hallways, to an open doorway that was shining bright as it there was a captured UFO on the other side. It took my eyes a moment to adjust once through that doorway. The room was filled with lights: some one stands, some mounted to the ceiling, some fixed to the walls. They were all pointing towards a soundstage, surrounded by red curtains that I recognized from the episode of The Gamble that I watched online. This was where I would make my first gamble.
They had me stand in the middle of that stage for a few minutes as the cameras spun around me and grabbed various angles for the editor. One of the cameras got right into my face, and then I heard someone say, “Look more worried. Give us a more worried look!” It took a minute before I realized he was talking to me. But even with a bit of acting training under my belt, I didn’t know how to fake a ‘worried look’. So I just kept standing still. “Perfect. That’s great,” the same voice said. “Just keep standing there—don’t react until you’re spoken to—got it? Okay, we’re going to film in three, two, one—and action!”
Finally, the host walked out onto the stage, holding his microphone. He was waving at an invisible crowd behind the cameras. He even did a little bow with his hands pressed together, as if he was thanking the audience for their applause—even though the studio was silent. I guess they planned on adding some applause in the editing room. “Thank you! Thank you! We’re excited to be back with another thrilling episode of The Gamble. This week, we’re with comedian, Orrin Pearson—famous for his edgy, offensive brand of humour. Orrin is a New York City based comic—but you probably know him because of a tweet he made.” The host motioned towards a large screen, which was now showing that infamous tweet. I rolled my eyes but I fought back the urge to defend myself. Why did everyone think that my humour was edgy and offensive? What jokes did I make on stage that were offensive? Was my bike-stealing bit offensive somehow?
“Orrin agreed to come on our show, determined to prove that his tweet is true—that he can easily tell the difference between a biological male and a biological female. Well, Orrin—do you really think that’s a gamble you want to make?” He held his microphone out to me, and it took me a moment to realize it wasn’t a rhetorical question.
“Um—I guess so,” I said.
“Let’s take that back!” shouted the clipboard man. “Orrin, we need you to sound a bit more confident. We’ll keep resetting until we get it. Still rolling—and action!” The host took a few steps back and then he walked towards me again. “Orrin agreed to come on our show, determined to prove that his tweet is true—that he can easily tell the difference between a biological male and a biological female. Well, Orrin—do you really think that’s a gamble you want to make?” He held that microphone out to me again. I really didn’t want to sound like a pompous ass, but I knew they were going to continue resetting until I sounded exactly like a pompous ass. So I bit my tongue and forced a smile.
“Let’s face it: guys look like guys and girls look like girls,” I said.
The host let a little fake gasp slip as he turned to the camera. “You heard it, folks—he’s ready to make his gamble. We’re going to set the stakes with Orrin right after these messages. Stick around!”
The room became silent as the host stared into the camera with a smile. I didn’t know where to look, so I just looked around, trying to figure out how they planned to humiliate me on television.
“Okay—cut! Perfect! Let’s move on. Get the girls out and let’s get final touches right away.”
Six girls walked out from a nearby door in a single file line. They walked straight to the stage and stopped on taped exes on the floor, as if they’d done a few rehearsals before I arrived. I looked at the girls. They were all thin and pretty. Most of them were shorter; two of them were tall, with Amazonian builds. They all had plenty of makeup on, and tight little dresses. One of them was showing a bit of cleavage, and another was showing a whole lot of cleavage—but her tits looked fake. I had a feeling that half of them were t-girls, and they were going to make me guess which ones.
But I figured it was a trick—somehow. Maybe they were all t-girls, or maybe they were all just normal girls who would lie and say that they were t-girls. It’s not like they were going to show me their cocks, so how could I really know for sure?
The clipboard man came onto the stage and he moved me over to a red X on the floor. “Just stand here and face the camera until the host tells you otherwise,” he said.
Then he ran off the stage and started counting down again. “Okay, let’s lock it up and roll! Camera’s speeding? Okay—and action!”
Now the girls were smiling, staring at the cameras with big smiles as if they were all excited to humiliate me for the whole country to enjoy. The host stepped back on the stage. “Okay, Orrin. With us, we have six girls—though in your mid-century opinion, only two of them are girls. Two of the girls standing in front of you are male-to-female transgenders. And two are cross-dressing boys. For this exciting two part episode of The Gamble, you’re going to pick the two girls you think are really girls—one today and one on our next episode. You will take your pick out on a date—maybe see a movie, maybe go to a nice dinner. You won’t have any idea if you picked a biological girl or a transgender or just a cross-dressing boy until the end of your date—and then you’ll do it all over again next episode. I bet that sounds pretty easy to you, seeing as you think you can easily tell the difference. Right?”
I looked over at the girls. This must have been some sort of carnival trick. They all looked like girls. They all had big eyes and nice hips and soft faces. Did they go out and find the most feminine trannies and boys on the planet? Or was I right with my original theory? Were they all actually gi
rls who were just pretending?
“Orrin?” the host said.
“Um, I guess I can probably figure it out,” I said. Then the clipboard man made us restart. Apparently I wasn’t confident enough again. They weren’t happy until I said, “This will be a piece of cake.”
“Well go ahead and walk up to the girls—take a minute before you make your first pick. And don’t forget, Orrin. If you correctly choose the two biological girls for your two dates, you will be going home with fifty thousand dollars. But choose wrong, and you have to do whatever our transgender girls—whoever they are—want you to do. Are you willing to take that gamble?”
“I’ll take that gamble,” I said. My heart throbbed. I didn’t know about the fifty grand. I could really use fifty grand, especially if I wasn’t going to be getting any gigs in the next few months.
I walked up to the girls and I looked into their eyes. They all smiled at me. One girl even gave me the ‘I want you to fuck my brains out’ look, as if she was desperately hoping I would pick her. Then I looked down from their eyes to their throats. I was scanning for Adam’s apples. Two of the girls had no lumps at all; one girl had the slightest lump that could have just been a slightly enlarged larynx. The other girls were wearing chokers, trying to throw me off. But lump or not—I’d heard of trannies getting Adam’s apple reduction surgeries, so it wasn’t enough evidence to make my picks.
“Surely you already know your first pick, Orrin,” the host said. “Like you said—it’s easy to tell the difference. Isn’t it?”
I took a deep breath, still convinced they were screwing with me. But I didn’t want to call them out while the cameras were rolling, just in case they weren’t screwing with me. I couldn’t admit that the challenge was hard. I couldn’t take that hit to my ego.
I at least knew the two girls with cleavage weren’t the cross-dressing boys. Otherwise, it was a complete gamble. The two tall women had thicker, more athletic builds, but again—it didn’t mean anything. They were probably just chosen to throw me off my game. I’m sure one of them was a woman and the other was a tranny. But which was which?
“How are you girls doing?” I asked. They all smiled and nodded. But it was their voices that I wanted to hear. So I went to the girl at the start of the line-up. “What’s your name?”
“Cassidy,” she said with a very quiet and meek voice. The three whimpered syllables weren’t enough to make a diagnosis.
“How are you doing, Cassidy?” I asked.
She smiled and nodded, giving me nothing to work with. She was cute: a short blonde with her hair nicely braided French style. She had full lips and a small nose, with no signs of plastic surgery.
I asked the second girl for her name. “Barbara,” she said. Her voice was more confident, but there was a slight deepness to it. She was also the one with the slight lump on her throat. She had thick brown hair, which looked a little bit like a wig—so I decided that I wouldn’t ask her on a date, even though she really could have been a chick with a few slightly masculine features and a wig. Girls can wear wigs too.
The third girl introduced herself as Megan. She was one of the tall ones, but she had the biggest, shiniest eyes. Her voice was convincing and she had a nice body—but it was her legs that made me think otherwise. She had thick, muscular legs, which were clad with leggings—possibly to hide her leg hair, or the razor burn from a recent shave. I decided I wouldn’t ask her out.
The next girl was Laura. Laura was also tall, also with a convincing voice. She had the large breasts, which were obviously implants. I was pretty sure she had implants in her ass as well. Of course I knew that girls get implants all the time, but I had no other evidence to work off of. I just had to assume that she was a tranny and hope for the best.
Next was Susie. Susie was short, thin blonde, with a bit of a mousey look—she was my type. She had narrow shoulders and wide hips—and I was pretty sure that there was no such thing as hip or shoulder surgery. Her feet convinced me that she was actually a woman: they were small and stuffed into a cute pair of heels, which couldn’t have held more than one-hundred and fifteen pounds without snapping. I was positive that she was a girl.
And finally there was Tiagra. Tiagra was covered in tattoos. She had thick lips and a cute sloped nose. She was wearing more makeup than the other girls, but her hair was obviously real, as I could see her recently dyed roots. Her hands were small and fragile-looking, and she was showing a touch of cleavage—so I at least knew that she wasn’t one of the cross-dressing boys.
So I had three solid options: Cassidy, Susie, and Tiagra. One of them was definitely a biological male. Hell, all three of them could have been biological males—but I figured my chances were better with them than with the other three.
“Well, Orrin? Who are you going to pick? We need an answer so we can get you out and on your date.”
I looked at the girls again. I found myself staring at Cassidy’s slight body, and my heart told me that she was my best bet. “I’m going to go with Cassidy,” I said.
The host spun towards the camera and said, “Orrin believes that Cassidy is a biological woman, so today, he’s going to take her on a nice date, and then tomorrow, he’s going to learn Cassidy’s truth—is she really the biological female Orrin thinks she is, or is she the transgender he’s so sure doesn’t exist? Or, could Orrin be so wrong that he picked a boy in girl’s clothing?” My heart fluttered down into my stomach. The thought of that last option was so embarrassing—even the possibility made my heart ache with humiliation. I took another look at Cassidy. She couldn’t possibly be a transgender or a boy in disguise. Right?
CHAPTER V
I didn’t have to do any of the planning, which was nice. The production team already had my whole date planned for me, though they made it look like I was the one who did all of the work.
They even let me return home to sleep for a few hours before they woke me up to get footage of me getting ready for my date. “Orrin—why don’t you tell us how you’re feeling? Are you nervous? Is Cassidy the kind of girl you would have asked on a date outside of this show?”
I shrugged my shoulders. “I don’t know. I don’t really know anything about her.”
“Okay, let’s take that back. I’m going to ask the same question. This time, I want you to sound more excited about your upcoming date. Make it sound like you’re really hoping that Cassidy is the real deal.”
I rolled my eyes. They were going to get me to say exactly what they wanted me to say. Hell—I probably picked exactly who they wanted me to pick. I wasn’t excited for the date, but they wanted to make sure that my potential humiliation was as horrible as possible—and apparently that meant making me look like some head-over-heels fool.
They made me unlock the bathroom door while I showered. It was weird having a microphone dangling over my head while I stood naked under a stream of water. The cameraman even popped his camera through the shower curtain. I covered my cock quickly. “Don’t worry—we’ll blur everything in post,” he said. But that still meant that him and all of the postproduction guys would see my cock. So I kept my hand over my crotch.
“Blur my hand then,” I said. I cut my shower off early.
When I got out of the shower, there was a bouquet of flowers on my counter. “That’s for Cassidy. You got it from a florist on 4th, just off Broadway,” said the clipboard producer. The flowers looked expensive.
“Does she know that you’re planning this whole date, or does she think that I’m really planning it?” I asked.
“You are planning it,” the producer said with a grin. Even if Cassidy was a transgender or a gay boy in girl’s clothing, I still didn’t want to hurt her. I didn’t want to get her hopes up thinking that I was actually interested in her—as if this was some sort of dating show. Despite what some people thought, I still believed that transgenders and gays were humans with feelings. I just thought that it was easy to tell the difference between the real deal and the imitation brand—th
ough seeing those six chicks in that line-up really made me wonder if I could be wrong. At least four of those girls looked and sounded like perfectly convincing chicks. And maybe there were more like them around. Maybe the broad-shouldered, flat-jawed trannies I saw on the streets weren’t the only transgenders walking around New York City. Maybe they were everywhere—all around me—and I never noticed because they were perfectly convincing.
I tried to push that thought out of my head. I didn’t like to think that I’d ogled a man before—or worse, hit on one in a bar, or kissed one thinking she was really a she.
I was still mostly convinced that all six of the women on that stage were actually just women. And at the end of the show, four of them would lie and say that they were boys in disguise, or men with some alterations and extra hormones. It’s not like they were going to pull up their skirts and show the world their bulges—and even if they did, the bulges would probably be fake.
I met with Cassidy on a street corner near Times Square. It was out of the way for both of us, but it looked nice for the cameras. She was in a new outfit: a white sleeveless top and a long black skirt, which flared outwards and extended down to her knees. She was carrying a little red clutch and on her petite feet she wore a pair of crisscrossing black heels, which showed off her white painted toes.
She had her hair tied back tightly, proving that it was real—but she now had a black lace choker around her neck, as if she was trying to hide something. “Nice to see you again,” I said when I approached her with the flowers.
“Are those for me?” she asked with her meek voice. I wish she would have spoken up a little bit so I could make a better male or female diagnosis.
“Yep—from a florist on, uh, somewhere near Broadway,” I said. I realized that my hands were shaking when I reached the flowers out to her. “You look nice.” Her top, like the dress she was wearing at the studio, kept her chest covered, not giving me any hints of her cleavage. But I was still convinced that she was a real woman. She had the thin wrists that only women seem to have, and her feet were so small. But it was her little nose and her soft features that really had me convinced. I’d never met a man with such a gentle jawline or such narrow shoulders. If she really was a man, then she’d gone through some seriously radical operations—and she was probably overly girlish to begin with.
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