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The Crossdresser did not Realize who they Were messing with. (Futanari on Male Story) Chapter 1
🕑 Added 2025-03-22 08:26:29 +0000 UTCThe silence did not last because the waiter came in, and we both ordered. I got myself a Salmon and scallops order, and Carly got herself the ten-ounce steak. I blushed as she said she would like it rare, and she turned her attention to me as the waiter poured her a red wine and me a white. I did not even know why I was blushing, but the attention of this beautiful sex goddess had her eyes on me, and I felt stunned. She was so tall and beautiful, and her stare just sent chills down my spine. I did not notice right away, but both her eyes were different colors, with one being this deep Amber that I did not even know existed, and her other eye was this violet that I could not help but believe to be so beautiful.
“Your eyes,” I said, my voice trembling a little, “They are different colors,” I told her, and she smiled brightly, “They are beautiful.”
“Mmm, Yes,” She said, “I have Albinism and a condition called Heterochromia. My albinism makes my eyes a bit nearsighted, and I don't do well outside under the sun due to the lack of melatonin in my skin, so sunny locations are impossible for me. My skin will die in the sun, but my sight impairment was dealt with by laser eye surgery. I can see twenty over twenty now, and my Heterochromia and my eye color make my eyes one of the rarest in the world. I am just a bundle of rare conditions that makes me one in a trillion,” She said with a massive smile.
“You look amazing,” I gasped honestly. She smiled brightly and licked her lips.
“Thank you, Angel, tell me about yourself, Angel,” Carly said, leaning forward, her large breasts pressing down on her arm, making them look even larger, and I gulped. “I am super interested in how you became a crossdresser.”
“I- Uh, Fuck,” I blushed as I accidentally cursed, but she only smiled. “I always looked like a girl,” I told her, trying my best not to show my nervousness. Those Amber and violet eyes just bore into me. The smile in them is dark and amazing. I wanted nothing more but to run away yet look closer at them. They were like two jewels that no one could ever see again after they were gone, and I took a deep breath. “I thought I may as well try it because I was so close to being one anyway from what people said to me growing up, so, I, tried it. Then, Um, I liked it.”
“I can see that,” she said, taking a sip of wine. “Tell me because we never really talked about it: Are you Bisexual?” She asked, her tone sounding innocent, but something told me that it was an important question to her.
I opened my mouth to reply, but I took a second and thought about it, “I would not call myself really attracted to men, but I always liked straight porn, and I like Trans porn too,” I admitted, my face so hot that I knew my blush was obvious. The way she smiled, though, told me that I made the right answer to her question, and she looked at me with much more happiness.
“Perfect, because I do have one more medical condition that makes me a bit more unique,” She said, “Already, I am one in a trillion baby, but it might even be worse than that. Add a couple more dozen zeros because,” She paused, “I am intersex. My doctors think I had a twin, and his cells merged into mine, and, well, it gave me both reproductive organs.”
Huh?
My mind blanked, and I looked at her. I could not find a single male feature, and she smiled at me. “What do you think? Are you going to reject me?” She asked, “Because I have a penis as well?”
Her question hung in the air, and I truly did not know what to say. After a minute, I found that I finally had words, and I replied, “Well, you accepted me for who I am, so why should I reject you for something you cannot decide?”
Carly smiled and looked me up and down. “I think, Angel, that I am falling a little for you. You are the first person to accept me without asking more questions or thinking I am lying. You know the coincidence that made me is something of an astronomical number that scientists would take a week to calculate, right?”
“Doesn't that just make you unique?” I asked, and she shook her head.
“Let's move on from that. What do you do for a living?” Carly changed the subject. “Or should I ask, what is your tech company in? Because I never asked that.”
“Oh, I am a software company. We started a business making fashion brands, and I made a great system integrating modern manufacturing plants and design. Most Companies in Fast fashion have been using this terrible system that is a major pain in the ass. I cleaned up the program and made a better system that also allows you to design in it. So you can take your idea and send it out without needing modification. It is all there in the application, which is also extremely customer-friendly,” I told her with a bright smile. I moved forward and continued, “It has cut down the time needed for a shirt design to go from concept to being made by one more day by cutting out unnecessary design integration. I now have a software contract with PVH Corp and have been customizing my software to their separate companies. Like Tommy Hilfigure, speedo, and a couple of their other companies,” I told her with a smile. “I am not a fan of the major company for various reasons, but I also love what I do, so,” I could only shrug, “I am not a saint.”
Carly smiled and shook her head, leaning back, “Problematic? I mean, child labor is problematic, but you are not the reason they are doing that. The honest problem is more systemic than that, and if those kids are not working, it is not like they would get an education from their government or various other things. It is a problem in their country. But I am not going to act like it is something that is good. So let us move on from that because it is a depressing topic, and we both seem not to want to virtue signal, which I appreciate.” Carly’s smile then returned.
“So, what do you do?” I asked, “You know more about me than I know about you,” I told her, and she smiled.
“You are right; I am not a fan of telling people what I do; let us just say I am in the material sciences and work at MIT. I don’t really teach, but I am very active in their research programs at their satellite research centers.”
“Oh, you are a scientist! I am an MIT graduate, but I am in software. Do you teach?” I asked, fascinated.
“Nope, I hate teaching. I tried it once, and the students were too busy ogling me to pay attention,” Carly said, and I nodded.
“They cannot help it,” I said, blushing hard, “I am having a problem from looking at you all over myself.”
The smile she showed was not one of a woman who hated what she had just been told. She leaned forward. “So you like what you see, Cutey?” she asked.
I nodded, and Carly leaned forward, put a finger under my chin, tilted it up, and I looked up for her. “Good, because I like the little cross-dressing girl in front of me, too. I think I want to take you home tonight already,” she told me. I shivered, my eyes widened, I flushed, and her perfect rose smell drifted over to me. I shuddered, and she grinned. “I like little crossdressers like you, but I guess we will have to see what dinner is like,” She finished, and her fingers touched my lips, and she smiled, “You are really good with your makeup too, good girl,” She told me, and I shuddered, and I twisted in my chair as my cock throbbed against my panties. “Now, tell me more about your hobbies,” she ordered. She let go of me and leaned back again, and I shuddered as I missed her touch a second after she left.
At that moment, there was a knock on the door, and a chiseled man walked into the room. He reeked of a strong manly calzone, and his muscles were visible even through his clothes. He was in a suit that showed the level of class at the place we were eating, and he smiled at Carly. “Wow, you are beautiful,” he commented. He came inside, put down plates quietly, and looked at Carly a bit longer than he should have.
Then he refilled our wine, “Please ask if you need anything. Also, this button will summon me if you need anything,” He said, reaching forward and grabbing Carly's hand, and I felt ashamed. I could tell that he was flirting with Carly, but I did not know what to do about it. He was clearly being a bit too handsy, but I always froze up in these situations, and so I turned, knowing I would see that look I had seen in so many women when I tried to shoot my shot in the past.
To my surprise, I saw a cold look on Carly’s face. She opened up her hand and looked at the button to summon the waiter. Then, she looked at the piece of paper in her hand, and she looked at her steak. “Angel,” she said slowly. I almost flinched, and my heart dropped in her cold tone. I had heard it so many times from my father and mother in the past, and I felt panic rising in my chest as I knew that she was about to leave the date. My mind knew it, and I opened my mouth to say something so she did not have to reject me.
“I am going to do something later that will paint me in a bit of a bad light, but I believe that I am very angry, and I hope that you will forgive me for this in the future for ruining our first date a little,” Carly said.
“Please—” I was about to say something, and I did not know what I was going to say as my brain caught up to the words she said, and I froze. That was not what she was supposed to say, and I looked at her sharply in surprise. Her face was hard and cold. The smile was no longer there, and she was looking at the sheet of paper. My eyes widened as I looked at the back of the paper, and I bit my lip.
Then Carly surprised me and turned the note around. I saw the phone number on it and then the note. ‘I know you are looking for a real man. Call me!’ I flushed, and I hated how bad I felt, as I did not know how to defend myself to her.
“What a fucking trash piece of shit like him thinks he is a real fucking man is fucking bullshit. What a fucking piece of fucking trash; he is not even fucking worth me stepping on his fucking balls,” She sneered, and her face sneered, which made my cock throb. Even her angry face was so elegant, sexy, and reeked of sex. She was so amazing, and I shuddered, looking at her with a tint of fear as I did not understand what was going on. “Fucking shit, ruining my date with the first real fucking-” She cut herself, then her entire demeanor changed instantly. No longer was she angry. Instead, she smiled and looked at me with a bright smile. “Sorry about that,” she said, “I am a little angry. Please, don't worry about that note and that waiter. I would be a fucking moron to think that a fucking waiter is more of a man than a crossdresser with a multimillion-dollar company. I prefer you over him anyway, so don't think about it.”
My heart soared, and I did not know what to say or do. I was smitten, and I fucking swore she had a pink horizon around her, and I blushed harder. I don't think I could ever recover if she rejected me now. I was left stunned, and she picked up her fork and knife. “Oh, hiding with the food, Cutey?” She asked with a mischievous grin. She leaned forward, letting me see down her breasts, and she jiggled them a little, “Don't worry, Angel. Tonight, it is about us. I want to make this relationship work, and I hope you feel the same,” She finished and leaned back, took a sip of her red wine, picked up her fork and knife, and began to eat.
Silence overtook us, and I did not know what to say to this goddess. I tried multiple times, but at that moment, I was just speechless and wished that I could say something and she was smiling. “Do you top or bottom?” Carly suddenly asked. I was looking down at my food, and it was half gone. I don't even remember eating that fast, and she was leaning back with half her steak and potatoes finished, too. She was clearly enjoying herself with that smile on her face, and I could see it in her eyes.
“W-What?” I asked, not sure what she meant, and she licked her lips.
“I said, do you Top or bottom,” Carly asked. “I like being a top. Despite my anatomy, I am obsessed with being a top, but I wonder if you want to be a bottom.”
“Bottom?” I asked, and I flushed, “I- I am sorry, I,” I looked away, “I am a virgin; no one likes me. Not my family, not women, so I, um,” I flushed, and I felt like a worm at this moment as I felt her eyes staring at me, and I finished, “The closest time I could have; she laughed at me.”
I braced myself and waited for the laughter, but the room was quiet. I turned to look at Carly, and instead of a smile of mirth on her face, I saw that she was cold. “What?” she said, her voice dropping to a chilly Antarctica day, and I shivered hearing it. Her voice was so expressive, and it told you her emotions with such perfection.
“She, um, laughed at me,” I repeated, “I am not large, in,” I felt on the verge of tears, “You know, down there,” I admitted, and I felt nothing but shame, and I hoped she did not end the date here now. “Please, give me a chance, I have been trying to learn how to lick pussy good!” I said, turning to look at her with a pleading look, but I saw her with a cold expression, and I flinched.
Then it warmed instantly, to my surprise, “Sorry, I am not mad at you, I am mad at that woman,” Carly admitted, “No one deserves to have their body laughed at. Mirco penis does have a corrective surgery although it will not make you massive, it can give you something to work with. But again, some women like them smaller, and it is fucking disgusting that she would do that. I am so sorry you had to deal with that. I do not care about Cock size. There are toys and various other things to supplement sexual intercourse, and you should NEVER feel less than because of something so fucking stupid like dick size.” She finished, and I blushed and looked away, feeling a warm feeling in my chest.
“Thanks,” I said, “You are the first to say that.” I was going to die in love with this woman at this point. If she was lying or anything like that, I was going to be devastated. She was hot and smart. This was no bimbo, and she was even defending me. I really did not want to call this love as I had just met her, but damn, I was falling for her hard, and my face was red.
I picked up my drink and finished the white wine, and silence took over as we both finished our meals. Carly then leaned forward and smiled, pushing her plate to the side, “This has been lovely, I am hoping that I can convince a cute boy like you back to my place. And I do mean to graduate you from that troublesome Virginity you are holding onto,” Carly said, licking her lips, “So what do you say?”
My mind blanked, and she smiled as I stared at her and could only nod. “PERFECT!” She said delightedly, “I am going to make sure that you will not be able to walk for a month. I will make sure you have a nurse, but for now, I am going to call that waiter in. Please watch how I deal with trash boys like this one,” Carly said and hit the button.
My brain skipped, and I looked at her, confused, “What did you just say?” I asked, my confusion growing. I swore I heard something there that I should be worried about.
I did not get a chance to listen to her answer, though. There was a knock, and the waiter came in, and Carly smiled. “You were amazing, and so was the dinner. Please, I need to thank the owner or manager. Do you mind collecting them for me? I will ensure it will be worth your time,” Carly said, and the waiter smiled and nodded.
“Absolutely. I will tell the chef who owns the place that you wish to thank him personally and want to see him, " he said and departed.
“Fucking moron,” She sneered as he departed, and she leaned back, “Who the fuck does that little fucking shit think he is. Hitting on someone like me in front of such a fucking cutie,” She said and looking at her nails, “I will ensure he remembers this fucking lesson.”
I was looking at Carly and did not know what to say; she was a little scared when she was mad. The sneer on her face was so hot, elegant, dark, and sinister. I did not know how to deal with it. It reminded me of those bullies, but this was even darker and was not pointed toward me. It was pointed at defending me and herself; I did not know how to feel about that.
Then, a woman in a white chef's outfit came in. Her demeanor looked a little rushed, and the waiter was right behind her. “Hello, I heard you wish to talk to me,” The Chef said, and Carly smiled, but I did not see it in her eyes. No, her eyes were cold and calculating, and that Sharktooth smile grew larger.
“Hello, The food today was DELICIOUS. I loved it,” Carly said, and the Chef smiled. I would love to come here again for the food. If you do not mind me being presumptuous, I would love to give you a little feedback, for I think it would bring your restaurant to a higher level.”
“Oh, Please. I am always open to suggestions. I usually don't take them in person, but sometimes it is nice to hear them,” she said, and Carly nodded.
“I am sorry for taking you out of the kitchen again; amazing,” She complimented, “The issue I have is in your service,” She continued and brought out the note, “I am here with a date for the first time, and we were looking forward to having a lovely time here, and your Waitor decided that I should have this note from the restaurant. I really did not appreciate how this made my date feel and how it hurt out the night,” She said, handing her the note. The waiter's face paled instantly, and the chef opened up the note. Her smiling face turned dark. You could see the contempt on her face, and she turned to the waiter.
“Get the fuck out for tonight,” She snapped, “I will review the footage and double-check the claim, but if this is from you, I will take full action against you. Your mother may have helped you get this position, so I will make sure that she hears about it.” The Chef finished, and she turned back, “I am sorry, I cannot take a customer completely at their word without some evidence, but this does look like my nephew's writing, and I will deal with it. If you come back in the future, I will PERSONALLY ensure that you will never see his face. Please let me comp the meal,” She finished.
“Oh, that is not necessary,” Carly waved her hand. “I am thankful that you will not just take my word for it. Science really dislikes only eyewitness testimony. I will pay and tip you personally,” she said, pulling out a dozen bills and dropping them on the table. Thank you for the wonderful meal,” she finished and stood and smiled at me. “Coming?” she asked, and I found myself leaving with her before I knew what was happening.
Then I was in the back of a car, and it was driving away, and I had no idea how I ended up there. I looked around stupidly. I was now inside a leather-seated car with a driver driving us away, and I looked at Carly with a tilted head, and she smiled. “Surprised?” She asked.
“Well,” I replied slowly, “Yes, I was a little lost on you defending me,” I told her honestly and blushed, “But then, I am now in this,” I motioned all around me at the expensive car.
“Oh, I am rich; don't think too much about it,” She said with a soft smile and then moved toward me. She got up from her seat facing me, and she sat beside me, and she pushed her breasts up against my arm. “You would not reject me now, right, because you have me wanting you, Angel,” She whispered into my ear, “I want you laid down with me deep inside you,” She then kissed my ear a little, and I did not know what to do. I was lost at sea, and my mind swam desperately without a boat.
She pushed me a little, then made me look at her, and I found her towering over me, her cleavage dangling before me and her smile sinister. “Stop being a little bitch, and fucking kiss me, Angel.” She demanded, and I blushed.
Then her lips met mine, and I was in heaven with her licking my lips and then pushing open my mouth. Then she invaded, and I moaned, and suddenly, I wrapped my arms around her, and my nose took in the rose smell of her perfume, and I pulled myself closer, no longer caring if I was being sloppy. She reacted instantly and kissed me back, only wanting more.
I do not know what I did in my past life to get the attention of a sex goddess like this, but she clearly wanted me. I was not going to say no, and I wanted only more.
Comments
jdhawks94
Damn , that’s fantastic writing!!!
