“So what are we doing?” she asked.
“We’re, uh, going to start by walking down 7th, to Times Square, and then we’re going to wander around Central Park for a bit. I, uh, think we’re going to get some ice cream, and then maybe see a show at Carnegie Hall. The producer standing behind the camera was nodding at me, letting me know I had it down right. They made me memorize the plan on the shuttle ride over.
We started walking, and Cassidy got right down to business, as if she was a robot being controlled by the producers—and maybe she was. “So, would you ditch me now if I told you that I was born a boy?” she asked.
I laughed and tried to keep my cool. I knew they were trying to get a specific reaction out of me. “No,” I said.
“Would there ever be a second date if you knew I was born a boy?”
“I don’t know—I mean—is it really so bad if I were to say no? If a guy wants to be with a girl, is that really so wrong? Can’t people do what they want?”
She looked away from me, suddenly looking disappointed. I probably should have lied, but I felt like I had to be honest. I didn’t want to patronize the girl with lies. Judging by the disappointment on her face, I couldn’t help but wonder if she was actually born a boy. Why else would she take my response so personally? Maybe she was just a really good actress. If so, it was a shame her talents were being wasted on some schlocky reality show.
“So tell me more about yourself. Where did you grow up? Do you have any brothers or sisters?”
She gave me a little rundown on growing up in the Midwest. Apparently her parents were quite conservative and she went to church every Sunday. I spent the next few minutes trying to figure out if that was evidence towards her being a chick or a dude. “Are you still a conservative girl?” I asked.
“I try to be,” she said.
“And are you close with your parents still?”
She looked at me. “Why wouldn’t I be?” she said.
“So you are?” If her parents were truly conservative Midwesterners, then they probably wouldn’t be okay with their son becoming a woman. So if she said that she was still close with her family, it meant—at least to me—that she was probably a girl and always had been.
She shrugged her shoulders. “I don’t really want to get into that. Didn’t you say that we were going to get ice cream?” She motioned across the street to an ice cream truck. We went over and I used the cash that the producer gave me to buy a couple of cones. She ate her ice cream in a girly, gentle sort of way, with little licks and a cute smile. The more I watched her, the more convinced I was that she was a chick. And the more convinced I was that she was a chick, the more I relaxed. We walked around the park with our ice cream cones and then we made our way over to Carnegie Hall for a symphony. Symphonies weren’t really my thing, and they weren’t Cassidy’s thing either. We snuck out the back door during the intermission, and then we found ourselves with no cameras on us, because they weren’t allowed into the theatre. “We should probably walk around and meet them back out front,” I said.
And then Cassidy looked at me with her pretty, shining eyes. “Well, they aren’t technically expecting us for another hour. Maybe we could go chat—just me and you.” She smiled, as if she was really interested in me and getting to know the real me—and not just the me that the producers wanted her to know. So we snuck away to a nearby bar and we got a seat in the back corner.
“How did you know about this place?” I asked.
“We used to come here when we were nineteen, because they never asked to see ID,” she said. She was suddenly much calmer and cuter without the cameras crowding us. It was such a relief to have a bit of privacy, even if I wasn’t technically alone. It was the first time in almost forty-eight hours that I didn’t have a whole team of people looming over my shoulder.
“This whole show is ridiculous,” I said. “I made one stupid tweet and now they’re treating me as if I said Hitler was awesome.”
“So the tweet really was just a joke?” she asked.
“Of course it was. I’m a comedian. I feel like everyone ignores that little fact.”
“So you don’t actually think that trans girls aren’t real girls?” She was staring into my eyes with a slight grin, as if she was getting let in on secrets that the producers didn’t tell her about. Did the producers say mean things about me to the girls? Were they trying to make everyone hate me?
“Well,” I said. And I had to think about it. “I don’t think they’re real girls. Only girls born with vaginas are real girls.”
“What about people born with both male and female organs?” she asked. “What about them?”
I sighed. “What about them? Everyone always brings up those weirdoes. What are they—like one in a million? There’s maybe ten of them in the entire country, and apparently we have to completely change the way we think about everyone because of ten weirdoes with birth defects.”
“What if I told you that I was born with both?” she asked.
“Were you?”
She smiled, as if she was about to laugh. And then I couldn’t help but ask, “Are you a real girl? Be honest with me.”
“According to you or according to me?” she asked, still with that grin on her face.
“Just tell me what I want to know. You know what I’m asking,” I said.
“Can’t you tell?”
My heart stuttered. I felt like I was being put on the spot—even though I was putting her on the spot. I knew that it was rude to ask. Who wants to be asked ‘Are you really a chick?’ If someone asked me if I was really a dude, I would have snapped. I wouldn’t just be sitting there with a grin on my face. But what else could I do? I only had her alone for another twenty minutes or so and I had so many questions that needed answered. “I think you’re a girl—that’s why I picked you,” I said. “By the way, you’ve got an olive or something on your shirt—just right on the inside of your collar there.” And then I realized I wasn’t looking at an olive. I was looking at a lavalier microphone. I had one attached to me as well—it had been there since I woke up that morning. The transmitter was in my coat’s inner pocket. I reached in quickly and pulled it out and saw that it was still beeping green, letting me know that it was transmitting. “Shit,” I said. Then I looked over and saw the camera in the window, hiding next to the wall.
Cassidy set me up. She snuck us out of that theatre because that was part of the plan. This whole thing was starting to look like a big ‘gotcha’ program. They were determined to embarrass me.
“You knew they were filming,” I said.
She looked over and pretended to be surprised by the sight of the camera. “They’re filming us?” she said.
I rolled my eyes. “And I thought we were actually having a nice time,” I said.
She looked at me with a slight frown. “I though so too,” she said. My heart stuttered. Did I just blow it was an adorable woman? Or did I just save myself from a humiliating disaster?
“I should probably get going here soon. I only got about three hours of sleep last night, and less the night before. I wouldn’t mind catching up.”
“Okay—it was nice meeting you, Orrin,” she said with a tone that suggested she wished she would have never met me.
We left the bar together, ready to part ways, and then the producer rushed up to us and said, “You have to walk her home. We need a better ending for this date segment.” Cassidy sighed, making me feel even worse about myself. But how was I supposed to react? How could the camera team have known where to find us without her tipping them off? She was the one who knew about the bar, and she was the one who brought up the whole transgender thing all over again while we were supposed to be free from the cameras. I knew that she was behind it—so why did I feel so bad?
Luckily, she didn’t live far away—just five blocks. We didn’t speak much along the way. I kept finding myself drifting further and further away from her, just in case she was really a male. I didn’t want it to
look like I was getting too cosy with a dude.
“Alright—it was nice to meet you, Cassidy,” I said. “Maybe I’ll see you around.”
“Maybe,” she said.
“Don’t leave yet!” the producer shouted from behind the camera. I looked over at him, waiting to hear a direction. “Do you think she’s a biological woman, Orrin?”
I shrugged my shoulders. “I don’t know. I guess I think so,” I said.
“I’m flattered,” Cassidy said.
“If you think so, give her a kiss goodnight,” the producer said.
I looked at Cassidy. “Yeah, I don’t think she wants that.”
“Afraid to kiss a boy?” she asked, rolling her eyes.
I was afraid to kiss a boy—with multiple cameras filming me and a producer excited to embarrass the hell out of me.
I sighed and then I looked into her eyes. “I’m sorry that I accused you of setting me up.”
“I’m sorry I made you think that,” she said.
“I really do think that you’re a girl,” I said.
“How romantic.”
“You’re pretty—beautiful even. I never really doubted you. I just doubted the show. They’ve been making my life hell for the past two days.”
She let a slight smile slip, as if she really was forgiving me. And now was my best opportunity to go in for that kiss they wanted so badly. But I still wasn’t actually convinced that she was entirely female. There was still a nagging little demon in the back of my brain suggesting that I was about to kiss a man. But what other choice did I have? Maybe the humiliation would be good for me. Maybe it would be humbling—or maybe it would at least look humbling, so that people could start the process of forgiving me for my stupid joke.
I leaned in. She closed her eyes and gently parted her lips. I closed my eyes and then our lips pressed together. And that’s when I was fully convinced that she was a woman. Her lips were plump and soft. No man’s lips could possibly be so soft. My heart was pounding ferociously before the kiss, but now it was calm. Even my trembling hands settled as they nestled on her hips.
“Want to come up to my room for a drink?” she asked with rosy cheeks.
“Only if the cameras don’t follow us,” I said. I didn’t hear any protesting from the production team, so Cassidy and I went into the building. We turned off our transmitters once we were in her elevator, and then we continued kissing. We kissed through the tenth floor hallway and then we kissed through her doorway and down her hall towards her bedroom. We didn’t even break away from our kiss as we fell onto the bed. Somehow my shirt ended up on her floor and somehow her white top ended up next to it. I unclipped her bra, exposing her small tits. Her bra had thick pads in it, giving her an extra cup size or two—but at least she had tits without the bra, and there were no signs of surgeries.
“Like my tits?” she asked.
“Yeah,” I said. But then I remembered that guys could develop tits after a few years of HRT—maybe they were hormone-induced tits. Maybe that’s why they were still so small. Or maybe I was just paranoid. I bent down and sucked on her nipples, making them hard. She moaned slightly. Then I started to slip my hands down towards her skirt. I started lifting it up, and then she stopped me, grabbing me by the wrist.
“You don’t want to ruin the suspense, do you?” she said with a big grin.
My heart stuttered. What was she talking about? Was she suggesting that there might be something unexpected under that skirt? I looked into her eyes. Then I watched as she sunk down, pulling away my belt and unzipping my fly. What if she did have a cock? Was I about to get a blowjob from a biological male? I didn’t want to ruin the moment by asking to see her pussy. I didn’t want her to think that I had any doubt in my mind. But I also didn’t want to get sucked off by a dude. So what could I do?
She pulled my already erect dick out from my pants. She gently pulled back my foreskin with a big smile on her face. “It’s big,” she said. “For once I can look forward to being the bottom.”
“Cut it out,” I said with a snap.
She laughed and shook her head. “C’mon—I’m just having fun. You aren’t seriously still thinking about all that trans stuff, are you?”
I bit down on my tongue. “No,” I said. “Of course not.”
She bent down and slipped my cock into her warm mouth, and then I closed my eyes and tried to imagine a wet pussy between her thick thighs, hiding under that skirt. But the image of a throbbing dick kept finding its way into my imagination, so I opened my eyes and shook my head. I couldn’t let those thoughts take over my head.
She was pumping my rod now with a tightly clenched fist. “Do you like it?” she asked, biting the bottom corner of her lip.
“Yeah,” I said. “That feels good.”
“Are you going to come for me?” she asked.
“I’m going to come in your tight little pussy,” I said.
“No—I want your come on my face. I want you to come for me now.” She tightened her grip and started beating faster. And she was good at rubbing my dick. She seemed to know exactly where to put pressure, and she knew exactly how much pressure was perfect. It almost seemed like she had tons of practise—maybe on a cock that belonged to her. I tried to push that thought away. “C’mon, Orrin. Come for me. I want your hot load on my face.” She had both hands on my cock now. She was beating me quickly, staring into my eyes. I looked down at her small tits, which were jiggling as she shook my rod like it was a piece of gym equipment. She was biting down hard on her bottom lip. Her cheeks were red, but probably not as red as mine. “Fucking come on my face,” she said.
I closed my eyes and bit down on my tongue. I could feel my orgasm coming. I tried to hold it back, but that only made the sensation more intense. I groaned and squirmed and then I opened my eyes just in time to see my hot load making a big mess of her face. She opened her mouth to accept one shot on her tongue. The rest landed on her cheeks, her chin, her lips, and her nose. One blast even teased her eyelid. She reached up and wiped all of the cum down towards her mouth. She licked it up with a big smile on her face. “You made so much cum,” she said.
“Did I?” I asked, still flustered and confused. I still wanted to reach for that skirt—yank it up to see if there was a bulge or not. Why was she hiding it from me? Was she just messing with me, or did she really have something to hide?
I looked at my phone while Cassidy was in the bathroom, getting washed up. I had a message from the producer. “Spend the night with her. We’ll see you in the morning.”
I didn’t want to spend the night with her, but I didn’t feel like I had a choice. I didn’t want to break the contract that I didn’t read, and I didn’t want to offend Cassidy.
She came out of the bedroom in a red satin nightie. “Should we go to bed? We’ve got to be at the studio at seven in the morning.”
“Sure,” I said. “But don’t you want to get a bit of pleasure too? I feel like I got all the good stuff.”
She winked. “I’m fine—just tired. I hope you don’t mind snoring, because I’ve been told that I can get pretty loud.” She skipped over to the bedroom and hopped into the bed. “Mind turning off the lights?”
That night, I tried to keep my distance from her in the bed, which turned out to be impossible because she kept nudging herself backwards into me—pressing her soft tush into my crotch. I put my arm around her, feeling her soft body and her small, perky tits. I was exhausted from two nights of very little sleep, but I still couldn’t fall asleep. Whenever she started snoring, I found myself wanting to reach down. I just had to get one quick feel in to know for sure: did a boy or a girl jerk me off? I hated that I didn’t know. I hated that I would find out on television—and even they might lie to me. The only way I would ever know for sure is if I felt for myself. But could I do it without waking her up? She hardly knew me—what would she think if she woke up to me grabbing at her pussy—or her cock?
I managed to fight back the urge to feel bet
ween her legs. I kept telling myself that she was a girl, no matter what the producers told me in the morning. I got sucked and jerked off by a chick, so I had nothing to worry about. They could try to embarrass me in the morning, but it wasn’t going to work. I knew the truth. I could feel her soft bum pressed into my crotch. Men don’t have soft bums like she had. Men don’t have tiny, cute feet like hers, or long, soft, beautiful hair. Cassidy was a woman, no matter what anyone said.
CHAPTER VI
They took me away in an earlier shuttle than Cassidy, and then I didn’t see her again until the director called, “Action!” All of the lights were beaming down on me, and Cassidy was standing on the far end of the stage, waiting for the lights to be turned on her.
The host walked out onto the stage and immediately started his bit. “So yesterday, Orrin went on a date with Cassidy. The date had some ups and some downs—let’s take a look.” He motioned towards the screen, and I was surprised to see that they’d already edited our date together. They showed us getting ice cream and chatting around Central Park—and then they showed our little spat in the bar and our awkward walk back to her place. They showed us going into the apartment building. Then, they apparently got a shot with a very long lens of Cassidy shutting the blinds of her bedroom, letting the whole country know that things got hot and heavy once the cameras weren’t on us.
Now the host was holding a microphone in my face. “So things got pretty heated last night, huh? Did you find out for yourself if Cassidy is the biological girl you thought she was?”
I shook my head. “Nothing happened,” I lied. “We just hung out for a bit. Cassidy is a really nice girl.”
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