Womanized

by Nikki Crescent

  I closed my eyes and tried to imagine a girl. But I wanted to open my eyes so badly. I wanted to watch his big, strong fingers stroking my shaft. But I didn’t want to want that—I was straight. I didn’t belong in this simulation. I should have never put that helmet back on—so why was I putting it on for a third time? Why couldn’t I just leave it off?

  His cock was deep inside of me now, pressing hard into my prostate. I groaned and squirmed and then I started to bounce up and down. I felt his hard veins rubbing against the rim of my anus. It was a bit awkward in that car, even though the backseat was surprisingly spacious. I knees were crammed into the seatback and I had to keep my head tilted down so it wouldn’t bang against the roof of the car. A part of me was worried that people would see the bouncing car and know what was happening—and then I remembered that it was a simulation, and the people outside of the car didn’t think anything. Even Tim didn’t have any real thoughts—he was just a program with a huge, throbbing cock.

  “Oh fucking hell, that feels good,” he said with a deep groan. I had an erection of my own now. His hands were on my hips, so I decided to reach down and stroke myself. His gaze turned down to my shaft as I began to jerk it. He was mesmerized, and I was a bit mesmerized as well. I kind of loved the way my cock looked with all of my pubic hair shaved away. I loved the way it looked, towering over my little skirt. And I loved the way the tight black dress felt hugging my skin. Maybe I could see what Michael saw in the whole cross-dressing thing—and maybe I could even see what he saw in the whole being a prostitute thing. It was fun, and it wasn’t much different than my fantasy of fucking random women after rock concerts. At the end of the day, it was all just naughty fun with strangers.

  “I’m going to come in your fucking asshole,” he groaned.

  “Come in me,” I begged.

  “But I want you to come on me first. Come on my face. Cover me with your warm jizz.” He leaned his very famous head forward just as the euphoria was starting to swirl towards the tip of my dick. I squeezed my cock tight and I jerked it quickly. I took a deep breath as that euphoria became more and more amazing—and then I unloaded on the famous director’s face. He even opened his mouth to catch a couple of shots. Then he let his head fall back as he groaned. I felt the hot blasting inside of me—he was coming, filling me up. I screamed and sunk my fingernails into his chest.

  “You’re such a little slut,” he said.

  I grinned. “You’re the slut,” I said. “Lay on your back.” So he laid himself down on that back seat. I stood up and quickly moved my ass over to his face. Then I pressed my hole against his lips and said, “Suck it out.” I felt the suction without immediately, without any hesitation. He sucked his own cum right out from my asshole. Then I stood up as best I could in that cramped car. “I need you to drive me to an ATM,” I said. I needed to get out of that simulation before I let myself move onto even more depraved things. Thankfully, there was a termination unit just around the corner. I hopped out from the car with my cock dangling down between my legs. I quickly followed the prompts on the screen, and then I was staring up at my white ceiling.

  There was a bit of cum on my chin. Apparently I’d had quite the cumshot while in the simulation. I used the towel to clean myself up, and then I went straight to my phone, to schedule a drop off time so that I could get rid of the tranny fantasy simulation unit.

  CHAPTER VII

  I was surprised when a man came to my door just a few hours later. “I’m here to pick up the simulation unit,” he said. “Do I have the right address?”

  I was silent for a moment as I stood in the doorway. I wanted it gone—at least I did until the man arrived to take it away. But now that it was ready to leave me, I wasn’t sure that I wanted to let it go. The thought of going back into that tranny world was exciting. I felt like I still had so much I wanted to experience inside of the unit.

  “Well?” he said. “I’ve got another unit here for a Kalvin Tapper. Is that you?”

  I was still slow to respond. I looked down and saw that he had my unit. But now, my rock star fantasy suddenly didn’t seem all that interesting. In fact, it seemed kind of boring: fucking random girls after shows. And I wouldn’t actually be the one playing the shows. I would only ever get to experience the feeling of being on stage, and not actually the feeling of playing the music. And what was the point of that? All of the cheering was fake—programmed sights and sounds. I still wouldn’t have any idea what it felt like to actually write and perform music that the world adored. But in Michael’s trap fantasy, I felt like I could actually experience what it was like to get romantic with foreign locals and rich celebrities.

  Though maybe they were both pointless. Maybe it was all just little wires stimulating the release dopamine at the end of the day.

  “C’mon, man, I’ve got eight other stops I have to make before I can go home to my wife,” the Smith Gadgets employee said.

  “Yeah, I’m Kalvin,” I said. “I’ll go grab the unit.” I went to my room and took one last look at the expensive device. I was worried that I would regret fucking men inside of the simulation, but the only regret I was feeling now was in giving the unit away. I would never be able to afford so many features with my salary. I would never have access to so many cities in the world, so many periods of time, and so many celebrities. Now, I would just get a few major towns and sex with strange women. I couldn’t help but wonder if there would be anything stopping me from getting dolled up like a chick. Would the people in my simulation embrace me the way they did in Michael’s simulation? Would girls still want to fuck me if I was wearing lingerie and makeup? Could I grow my hair out or would I have to find a wig?

  I stuffed the unit into its case and then I brought it to the deliveryman at the door. He took it and pushed my unit into my apartment with his foot. “Call customer service if you have any problems or if you want a refund,” he said.

  I looked at the side of the box and saw my name. I opened the box up. It looked just like the old unit: blue and silver with the glowing Smith Gadgets logo. I got it plugged in and placed on my nightstand, and then I got that helmet on my head. I was hoping that I would feel better about the swap after a few minutes in the fantasy that I designed myself. Surely the regrets would flutter away as soon as those beautiful Japanese twins were standing naked in my green room once again.

  The unit kicked in after a few minutes.

  CHAPTER VIII

  I fucked the Japanese twins properly, without that confusion and anxiety that I felt the first time. Then, when I returned to my downtown hotel, another group of sexy, young groupies were waiting for me. I brought them up to my penthouse suite and had a nightlong orgy, letting the girls take turns sucking and bouncing on my cock. I made them do filthy things: eating out each other’s buttholes, fucking each other with strap-ons, which just happened to be in my hotel suite, and so on. It was a fun night, but it was all downhill from there.

  When I went into my simulation the next day, the scenario wasn’t too different. Now I was in Tokyo, playing for a large crowd of people. The simulation gave me more stage time: two whole songs, but it wasn’t very realistic, and the music wasn’t very good—though the crowd was still roaring as if it was the best music ever written. It was an unfortunate reminder that the crowd wasn’t real and I wasn’t really in a rock band.

  The whole time I was on stage, I wasn’t in control of my own body. The simulation was overriding my own controls, so all I could do was watch as my fingers moved along the guitar’s fretboard and my feet stomped on all of the correct pedals. As soon as that last guitar riff of that somewhat annoying song was over, I regained control of myself. I was able to wave my arms at the crowd and they all roared and waved back. It was kind of fun for a bit, but it got boring fast. After a few more times in the simulation, I ended up going to one of the settings terminals to make it so that the simulation would start after the show had ended. I was starting to wish that I would have ordered more variety with my
fantasy.

  I was even starting to notice that some of the girls were the same. Wherever there was a group of girls waiting for me, a few of the faces would be recycled from previous nights, as if the simulation only had a few dozen girls to rotate through. It was only a week after I got my unit that the Japanese twins were back in the crowd, smiling at me, hoping to be taken back to my green room—so I took them back to the green room, but that excitement was almost gone now.

  I was starting to wish that I would have kept Michael’s simulation unit. He had so many extras programmed into his simulation. He had all of those cities and all of those people. When I was buying my unit, I didn’t think that I would care for the variety. I thought that my rock star fantasy alone would be enough to keep me satisfied—but it had only been a week and I was already getting bored. And that boredom was quickly turning into depression. Every time I saw a familiar face in my unit, I would remember how much money I spent on the damn thing, and then I suddenly wasn’t in the mood to fuck. With all of the repeating girls, it started to feel more like pornography than sex—and I suppose it was technically pornography that I was somewhat in control of.

  It was two weeks later when I decided not to spend the night in my simulation. It remained on my nightstand untouched for the first time since it arrived at my door. And then the next night, I stayed out of the unit again. I found myself dreaming of Michael’s unit, and then I would wake up wondering if there was any way to get it back. When I finally went back into my own unit, I ended up trying to relive a little bit of the fun I had in that tranny prostitute simulation. I asked one of the groupies for her clothes and then I found some makeup in one of the green rooms. I spent hours of simulation time trying to doll myself up. And then I went back to my hotel and had one of the groupies fuck me in the ass with that strap-on dildo. Finally, I had some of that excitement back—but it just wasn’t quite the same. After a few nights, it started to feel mundane, spending an hour or two in front of the mirror just to look good for some simulations that would have been just as excited if I smeared black ink all over my face.

  I tried taking my female guise to the simulated streets. No cars pulled over to pick me up, even when I was standing on a dark street corner in nothing but lingerie. Every person I stopped on the street said, “Hey! Aren’t you the guitar player for Over Oleander!?” Every single person in that simulation was programmed to recognize me, even when I was dolled up like a prostitute. Maybe I shouldn’t have told the Smith Gadgets people to make me as famous as they could.

  It was the end of the month when I wrapped the unit up and put it back in its box. Sex in the simulation was fun, but it wasn’t worth that horrible guilt that I felt every time I put that helmet on and remembered how much money I spent on the thing. I found myself on the Smith Gadgets website, reading through the longwinded return policy. They accepted returns after fifteen days. I was beyond that threshold, but I wondered if they would allow an exception. I called and waited on hold for an hour, just to hear, “We don’t allow any returns after fifteen days. Sorry.”

  “Is there any way for me to change my simulation? I don’t even want a custom one—I just want one that someone else got. Michael Peters—just put his program into my unit.”

  “I’m sorry, sir, but it’s not quite that simple. You can order a new simulation, but you still have to go through the process.” And that was her way of saying: ‘If you want Michael’s simulation, pay us the hundred grand that Michael paid for his.’ And maybe that was only fair. If he paid that much, it probably wasn’t fair that I pay less than half to get the same thing.

  I posted my unit for sale on eBay, for five grand less than what I paid. It didn’t sell, so I dropped it by another five grand, and then another. Finally, someone bought it at a loss of fifteen thousand dollars. I wasn’t proud of the sale, but I was happy to have the thing out of my life, so it wasn’t in my house reminding me that I wasted most of my life savings on a glorified sex toy.

  But even with the unit gone, I still found myself reminiscing about the time I spent in Michael’s simulation. I could still practically feel that excitement of being in a room alone with one of those men. My heart would still jump at the thought of being all dolled up and sexy, catching my own reflection in one of those simulated mirrors. I loved the idea of being in Paris one night and then in Amsterdam the next. And it wasn’t long before I started to wonder: what was stopping me from doing that in real life?

  CHAPTER IX

  I had enough money to travel for at least a few months if I wanted to. There were overnight trains that went from city to city in Europe that weren’t terribly expensive. And maybe I wouldn’t be spending nights in glamorous penthouse suites, but it wasn’t the glamorous penthouse suites that made that simulation so enticing.

  The only question on my mind was: could I pull it off in real life?

  I went online and ordered a few things, just to see: a makeup kit, a wig, a dress, a pair of panties, and a pair of heels. I ordered everything express, but I still had a night to kill. I spent that night shaving my legs and armpits and plucking my eyebrows.

  Everything was at my door the next morning. I rushed it all inside and got started right away with my makeup. I filled in my eyebrows and rubbed some concealer all over my face. It was strange how I knew what to do from the practise I got in my simulation. I already had hours of practise putting on eyeliner and eye shadow and blush and highlight. It wasn’t even an hour before I was staring at that familiar face that I knew so well from Michael’s simulation.

  I got that wig on my head and then I squeezed my body into my little black dress. I swayed from side to side as I ogled myself in the mirror. I looked so cute, and now my heart was pounding viciously because I wasn’t in any simulation—which meant that I actually looked cute. Maybe there was no mind games being played in that simulation. Maybe that really was just the way I looked. Now I found myself wondering if that Michael guy looked nearly as good.

  I spent that whole morning practising my voice, and then I got the idea to go down to the Aritzia on the street corner, to buy some more clothes, so that I had more than just a little black dress. My heart raced faster as I stared out my window at the shop. Could I really do it? Would everyone look at me and know that I wasn’t really a woman? Or would I pass? And what did that mean if I passed? Was this really something that I wanted to have in my life?

  I went to my front door and gently grabbed the handle. My hand was shaking, but now that I had the idea in my head, I couldn’t turn back. I threw the door open and I hurried towards the elevator, afraid my neighbours would see me. That little black dress suddenly felt extremely little. I kept reached down to tug on the skirt, making sure it was covering my bum. I think it was.

  I felt even more exposed when I stepped outside and could feel the warm breeze teasing up my shaved legs. There were people all around me, walking by, and some of them were looking over at me. I wasn’t used to people looking at me. I was used to being invisible. And I definitely wasn’t used to men smiling at me. At first I tried to avoid their gazes, but I could feel them all around me. I had to force myself to look up, so that I wouldn’t look like a psychopath. And they really were smiling at me, and as far as I could tell, they weren’t laughing the moment I looked away.

  I went into that store and fluttered from rack to rack. I picked out a few dresses, a couple of skirts, a few cute tops, some leggings, some costume jewellery, and a little handbag to replace my leather wallet. “Finding everything you’re looking for, miss?” the store clerk asked me. I heart leapt at the sound of that word: ‘miss’. I turned and looked at her, and she was staring at me with a warm smile. Was she just being polite, or did she really think that I was a miss? “I’m good,” I said.

  “Want me to take all of this to the counter for you?”

  “Sure,” I said, handing her my pile.

  “We just got our fall line in and there’s a brownish-orange dress that would look super cute on you. Do
you want me to get it from the back? We still haven’t put any of it out yet.”

  “Sure. That would be great,” I said. And the dress did look cute on me, so I bought it as well. I took everything home and spent the rest of that afternoon playing dress-up in my own apartment. It was fun. I felt so alive. I felt that same excitement that I felt in Michael’s simulation. I felt like I could do anything—I could go to Europe and hope from city to city. I could go to a ritzy bar and be hit on be celebrities. I could just sit out on some café patio and enjoy the excited gazes of single men. I could experience Michael’s simulation once again without having to put on any silly helmets. The experiences would be real, and the excitement was definitely real.

  That night, I touched up my makeup and went out. I didn’t know where I was going—I just knew that I wanted to be out of the house, spending some time in my new real-life simulation. I walked down the busy streets as the skirt of my dress bounced and bobbed, probably exposing a little bit of my bum behind me. I was only out for fifteen minutes before I got my first catcall: a group of young men across the street, headed in the opposite direction.

  It was a nice feeling, and I didn’t want it to end. And unlike the simulation, it wasn’t going to end until I wanted it to. There were no limits on how long I could be out. There were no shops and bars I couldn’t go into because they weren’t programmed.

  I went into the first busy bar that I walked by. It was a place I’d never gone inside before because the lines were always so long. And I didn’t even intend to go inside, but as I was walking by, the bouncer opened up his little barricade and said, “Go ahead.” Apparently I was pretty enough to skip the line. I was the kind of girl they wanted inside of their bar, so that guys would want to come back again and again.