It was quiet up in my apartment—too quiet. We walked in and I locked my door, even though I knew the producer had a key of his own. But they were still out looking for us on the streets of New York City, so we still had some time. We stood awkwardly in my apartment hallway. “Want a drink or something?” I asked.
“I guess so,” she said.
So I went to the fridge and got her a beer. It was all that I had. She cracked it quickly and took a long sip. I cracked one of my own but I didn’t take a sip right away. Instead, I watched her. I looked at her closely and studied her figure. She still had those narrow shoulders and those wide hips. She still had that gentle face and that beautiful hair. She was still a woman as far as I could tell.
“That camera team will probably be back soon,” I said, hoping she would get on with this ‘proof’ that she apparently had.
She stared into my eyes for a moment. “This is very embarrassing—I hope that you know that.”
“I can imagine,” I said. And then she continued to stand still, as if she was waiting for me to tell her that she didn’t have to show me anything. But if I was going to suffer through some humiliation in the morning, then I wanted to know that it was justified. Though I was almost positive that Susie had nothing to show me. Maybe she would show me some bulge in her panties—a fake cock put there to give me a heart attack. But I was going to make sure she gave me definitive proof—proof that she didn’t have because it didn’t exist.
She took a deep breath and then she lifted up her skirt, showing her panties. To my surprise, there was no bulge. I was just looking at a totally normal pair of panties on a normal girl. Then she reached down with two fingers and she began to pull her panties to the side. Suddenly, a long cock flopped out. It had been tucked back, between her legs. Her ball sack was deflated as her testicles were inside of her body.
And I was speechless. My heart stuttered and then I took a closer look. It must have been fake. The production team probably paid a lot of money for it. I looked around me, trying to spot hidden cameras. Maybe the plan was to get me alone in my apartment. Maybe the crew had set up many little cameras while I was sleeping, hoping to get all of my humiliation documented. “It’s fake,” I said as my skin began to turn red. “It’s like something they use in movies.”
She rolled her eyes. “Feel it,” she said.
“No,” I said.
“Then what other proof do you want?” she asked. She let her skirt fall down, covering that cock up.
My heart was still racing. I bit down on my tongue and I wiped the sweat off of my forehead. “Let me see it again,” I said.
So she lifted up her skirt. It was still dangling there. And how could I know that it wasn’t fake? Even if I touched it—I didn’t know what a prosthetic felt like. Maybe it would feel exactly the same. “Get it hard,” I said. My voice was trembling slightly. I felt like a complete lunatic, but I had to know for sure—and I knew that there was no such thing as a fake cock that could become realistically aroused.
Her face became red. “And how do you want me to do that?”
“I don’t know. Think about something sexy.” I took a deep breath. I looked over at my thermostat, to make sure it wasn’t cranked past one hundred degrees. It was actually a few degrees below room temperature.
“I can’t just get myself aroused,” she said.
I smiled. “So it is fake,” I said. “Any guy can get himself aroused. You just massage your dick until it’s hard—it’s not rocket science.”
“But I’m not a guy,” she said with a grin of her own. “Girls are more complicated than guys. We need more than just rubbing.”
I shook my head. “Bullshit.”
“Take off your clothes,” she said. “And rub your cock. Get yourself hard. That might do the trick.”
I laughed, and then I realized that she was serious. Did she actually want me to strip down in front of her? Did she really want me to jerk myself off like an idiot—probably with a dozen hidden cameras pointed at me? I looked around. “Where are the cameras?” I asked.
“Take me somewhere you know there aren’t any cameras,” she said. “Or are you just determined to think that you’re right?”
“Fine,” I said. I thought for a moment and then remembered that the building manager sometimes left the door to the roof unlocked. There was a garden up there, but it was late now—there was no way anyone would be up there, and there was no way the production team even knew about it. “Follow me,” I said. I led her back to the elevator and then we went all the way up to the top floor, down the hallway, and up the ladder to the roof. It was a warm night and the city lights were impressive.
“Okay,” she said. “Now strip. Get me aroused.” She shimmied down her skirt and then she shimmied down her panties, revealing that very real looking cock. But I knew it had to be fake.
I took a deep breath, and then I pulled off my shirt. I tugged down my pants, and then she said, “Slow down. Make it sexy. If you want to get me aroused, you’re going to need to put in a bit of effort.”
I forced a smile and slowed myself down. I gently tugged my pants down to my ankles, and then I stood up straight. I took the waistband of my boxers and began to dance them slowly down my hips, first revealing my pubic hair, then revealing the base of my shaft. “Is this doing it for you?” I asked.
“You’ve actually got a pretty nice body. You should wear clothes that show it off more,” she said with a big smile.
“What can I say? I go to the gym about once a month.” My face was red-hot as I pulled my boxers over the tip of my shaft. I was standing naked in front of a woman with a fake cock, standing on top of a building where we could be seen by anyone with a half-decent pair of binoculars.
“Now rub it,” she said.
So I took my cock and began to rub it with my fist. “This is very embarrassing, by the way,” I said.
“Rub it slower. You look like a monkey at the zoo.” She laughed. I had to admit: she had a cute laugh—and a very feminine laugh. How could a man learn how to laugh in a feminine way? Isn’t laughter an automatic and instinctual thing? I rubbed my cock slower. But it wasn’t getting hard. “Show me your titties,” I said.
“Titties? What is this—high school?” she laughed again. Then she gently took the base of her top and lifted it up. She wasn’t wearing a bra. She had nice, perky tits—but I could see the subtle scars from her implant surgery. Lots of girls get implants—not just t-girls. But for implants, they were nice. Her nipples were perky and her breasts looked soft. She took one and squeezed it gently. “Do you like them?”
“They’re nice,” I said. And now I could feel a tingling in the tip of my dick. I was getting hard. I kept my gaze glued to those breasts—at least I tried to; but every few seconds, I couldn’t help but look down at that cock, which was starting to seem bigger. It was even starting to curve slightly to the side. But that must have been in my imagination, because it wasn’t real and fake cocks can’t become erect.
“I’m getting hard,” she said. My heart skipped a beat.
“No you aren’t,” I said. “But nice try.”
She reached down and grabbed her dick. She lifted it up and gently pulled back her foreskin. Now her testicles were in her ball sack, having descended after being stuffed up all day. I could almost see that ball sack swelling, and then veins up and down her shaft looked darker, as if they were pumping blood into her shaft. But it just wasn’t possible. She couldn’t be a man. She was too beautiful. She was practically my dream girl—but how could my dream girl have a cock?
I stopped rubbing. I found myself watching her. She let go of her shaft, but it remained upright, now erect and throbbing. “Believe me yet?” she asked. She reached down and covered it. She had dark red cheeks.
“Wait—it’s fake. It has to be fake.”
She rolled her eyes. “Why can’t you just accept that some transgender chicks are your type?”
“You’re not my type,” I said. My voice cracked. “I
mean—you’re very pretty, don’t get me wrong. But you’re—you’re a man.”
“A man?” she said. “That’s rude.”
“Don’t get me wrong. You’re beautiful and convincing. And you sound just like a chick. And your body is… it’s out of this world.”
“So what about me is manly to you? Is it just my cock?” she asked.
“I don’t know,” I said. I felt panicked, like my world was crashing down around me. Were my critics right? Were there t-girls who were just as feminine as real girls? And if Susie went and got the full reassignment surgery, what would be left for me to cling onto? Was I really going to start judging my women based off of their DNA? Was I going to demand a DNA test from every girl I wanted to ask on a date? At some point, I needed to accept that some traps could really be women, or I was going to drive myself crazy.
“I’m sorry if tomorrow is embarrassing for you,” she said. “I hope you don’t think that’s what I want.”
“It’s fine. Maybe I deserve it,” I said.
“I don’t think you do. Our opinions are based on our experiences. It’s easy to judge an opinion, but it’s not so easy to judge a person’s experiences,” she said.
“You really are very beautiful. I mean—I guess I think you’re a woman—even with that—that thing.”
“Thanks,” she said. “That means a lot—especially coming from you.” She smiled. “But can you prove it?”
“Prove it? How can I prove it?”
“Well you slept with that Cassidy chick, didn’t you? Maybe—I don’t know—maybe we could fool around a little bit.”
“You want to fool around?” I asked. My heart fluttered. I was terrified, but also strangely excited. I felt like I was about drop a whole lot of weight off of my shoulders. I felt like I was finally going to get my career back, but for the right reasons—without having to lie. When the next person asked me about my tweet, I could really tell them that I was sorry, and mean it.
I walked over to Susie. I put my hands on her sides and then I leaned in to kiss her. And her lips were soft—just as soft as Cassidy’s lips—maybe even softer. I slid my hands up and down, feeling her curves. How did she have curves? She was a woman—and most women have curves. So why was I surprised? It was going to take some time before I was completely comfortable with the whole transgender thing—but that’s only natural. They couldn’t possibly expect me to change entirely overnight—though they were getting a pretty massive change.
I cupped her breasts and squeezed. They felt real, though a bit stiff. I gently pinched her nipples and rolled them, making them perkier. Then, it was time to cross the biggest barrier.
I reached down with one hand, across her stomach and across her pelvis. She was clean-shaven, making my first time with a tranny easier to handle. Though my heart still skipped a beat once my fingertips crossed onto her shaft. It was hard and warm, and I could feel it throbbing. I paused for a moment while I caught my breath and calmed my heart. Then I slipped my fingers around her curved girth. “It’s not so bad, right?” she said.
“I guess not,” I said. I looked down at it as I pulled back her foreskin. Her cock was actually kind of pretty in a feminine way. She clearly kept good care of it—keeping it clean and moisturized. I watched as I gently pumped it. Her tip was starting to turn a slight shade of red.
“Do you want to suck it?” she asked.
I sunk slowly to my knees. I curled my fingers around her cock and then I aimed it right at my lips. I didn’t close my eyes and I leaned forward. It was a strange sensation: feeling her cock in my mouth while smelling her floral perfume. I slid her shaft back, all the way to my throat. I slurped my tongue around it, feeling all of her veins and hard ridges. “That feels good,” she said.
I gently nodded my head, as much as I could without spitting out her dick. I kind of liked the way it felt in my mouth. It was warm and satisfying, cradled perfectly on my tongue as if it belonged there. I had my hands on her thighs, with my fingers wrapped all the way around to her perky bum.
I slipped my hands back, so they were more on her butt cheeks, with my fingers pressing into her butt crack. I even slipped a fingertip into her tight butthole, making her perk up and gasp. “You’re dirty,” she said.
“You’re hot,” I said, looking up from below her tall shaft. It was an interesting view: with her erection and her perky tits in the same line of sight. But I kind of liked it. My heart stuttered with arousal. “Turn around.”
She smiled and bit her bottom lip as she spun slowly, facing her bum towards me. It was a more familiar sight: a woman’s ass. I took her cheeks and spread them, revealing her puckering hole. I leaned in, nestling my face between her cheeks. I pressed my tongue into that little hole and I began to lick. It was only a few seconds before she was moaning and giggling at the same time. “What if someone can see us?” she said.
“Who cares?” I asked.
“Aren’t you worried about what your fans will think?”
And I figured she was referring to the commenters with their swastika profile pictures. “I could care less,” I said. I got my tongue in deep, making her perk upright and gasp. I even slipped a finger in, so that I could feel the inside of her body.
“Are you going to fuck me or what?” she said.
So I stood up, bent her over, and pressed the tip of my throbbing erection against her wet back door. I rubbed it in circles, teasing her and teasing myself. I felt calm—not worried at all about the fact that I was about to penetrate a biological male. But to even think of her as a biological male seemed absurd. She was a woman as far as my mind was concerned, and no amount of evidence suggesting otherwise could make me think anything else. I started pressing my tip into her butt. She clenched hard on my cock, which felt amazing. I pressed my fingertips into her sides as I held her tightly.
“You’re so big,” she said.
“You’re tight. But I can fix that,” I said with a big grin.
She was already moaning, already halfway towards her orgasm. As I sunk in deep, I reached around and grabbed that beautiful cock. I squeezed it and stroked it, revelling in her throbbing. I felt her warm tip and then I wiped up the drop of pre-cum that was oozing out. I brought it to my lips and tasted it. It was sweet.
“Fuck me already. Please just fuck me!”
I started pumping her, making her moan and groan and squirm. I couldn’t take my eyes off of her, and I could take my hand off of her cock. I kept pumping, desperate to make her come. I wanted to taste her load. I wanted to feel her thick substance dripping off of my fingers. I wanted to rub it up and down her shaft and then I wanted to smear it all over her perfect, perky bum.
I was thrusting her quickly, loving every second inside of her tight tunnel. I would slap her ass to make her clench, so the pleasure would become even more intense. And then I wasn’t sure the pleasure could possibly become any more intense.
“Fuck,” I groaned. “I think I’m going to come.”
“Just ten more seconds,” she said with her teeth clenched tight. She started to scream and then I felt her cock bloating up. I slid my hand up to her tip and then I felt that first blast of warm wetness. She was coming and I was catching it like a human condom. I waited until the palm of my hand was full, then I spread that goo down her long erection. I smeared some on her backside, and then I licked some off of my fingers. It was so delicious—she was so delicious. I couldn’t hold back any longer. I came in her tight hole.
She screamed and I groaned and nearly toppled over with her. But somehow we stayed on our feet. I pulled out of her tush and watched as my creampie oozed out of her, falling out in globs down her beautiful thighs.
“You have to stay the night,” I said.
“That won’t just make tomorrow more embarrassing?” she said.
“No,” I said. “If anything, it will just make people extraordinarily jealous of me.”
Her face was bright and lit up. She was smiling and biting her bottom lip. We fu
cked again that night, while the camera team was asleep in my living room. We tried to be quiet, but I’m pretty sure we woke everyone up when Susie came. She screamed and made a bit of a mess of my bed sheets—but I didn’t mind.
They took her away in an early shuttle that next morning. I didn’t see her again until she was standing on the stage.
“So Orrin—we understand that you already discovered Susie’s true gender,” said the host of the show once the cameras were rolling. “Why don’t you let the audience know what you learned?”
“She’s a woman,” I said.
The host smiled. “Right—well, she wasn’t always that way, was she?”
I shrugged my shoulders. “She’s a woman now, isn’t she?” I said.
“So you’ve changed your views—that’s great to hear. You may have lost the gamble, but you’ve gained a whole new sympathy.”
I shook my head. “You didn’t answer my question,” I said. “Don’t you agree that she’s a woman now?”
He looked at me with an awkward smile. “Of course I agree,” he said.
I smiled. “Then I didn’t lose the gamble,” I said. “You told me to pick two women, and I picked two women. Unless you’re now saying that Susie isn’t a woman.”
The host stuttered. He looked at the camera with a terribly awkward smile and then he looked back at me. “I—uh—I suppose your right.” Now he was looking at the producer, who was shrugging his shoulders and shaking his head, as if he didn’t know what to do. “Should we cut?” the host hushed.
“You can do as many retakes as you want,” I said. “I’m going to say the same thing. Susie’s a girl. And by the way, we’re going on another date today. You’re welcome to follow us around for a bit if you need more footage.”
“I—uh—I guess you’re right. I guess you did pick two women, so you technically are the first winner of The Gamble. How does it feel?” He held the microphone out to me while looking back at the producer.
“It feels good. To be honest, I’ve never felt better—and not just because you’re going to give me a lot of money. I feel… happy. I don’t know if I’ve ever felt this happy. I’m just so excited to take Susie out on another date. I think we’re going to check out that museum that we missed yesterday. What do you think?”
Womanized Page 51
