Boss Turned me Into a Shemale

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Boss Turned me Into a ShemaleI should’ve guessed something was up when my boss Victoria winked at me on our way into the office. She’s about 5’9″, 130lbs, she just got a boob job last winter, and as she walks by her ass bounces in the sexiest way I’ve ever seen. Work started normal enough. Our company was in the testing phase of software for a military application. I wasn’t clear on its purpose at the time. One of the women in my team walked into my office and told me Victoria needed to see me. I walked into Victoria’s office and closed the door behind me. “Chris, what’s the darkest secret you have?” I still didn’t think anything was the matter. I replied, “I can’t think of anything I’d want to bring up at work. What’s going on?” “We tested the new program on some our employees, including you.””So?” She laughed and moved around the desk to show me her iPad. “Does this look like someone we know?” She rapidly swiped through the pictures. Every one of them was from my home computer, and they were all in varying stages of cross dressing. “I think our new software works pretty well doesn’t it?” I was in total shock. I stared into Victoria’s eyes completely at her mercy. “This is going to be a dream come true for both of us believe it or not.””What do you mean?” I asked still not fully comprehending what was going on. “Instead letting this leak to all your coworkers, friends, and family, I’m going to turn you into a shemale porn star.” I was frozen by the thought of being exposed to everyone I know. So I said,”how do we start?””I didn’t think you’d object. First of all you’re getting a new assignment. You’ll work from home now. 2nd you’re going to move into my guest house leaving all your belongings behind. Especially your clothes. 3rd, starting now and incrementally over time we’re going to change your appearance so you look as good as her,” she showed me a stunning picture of Bailey Jay on her tablet. Or I can just go ahead and get these sent out to everyone. I’ll even rent a billboard on the highway with you dressed up so cute.” “I’m in I’m in. Please don’t expose me like that. What do I need to do now?””That is excellent to hear. I already booked our appointments for the day. We need to make sure you’re healthy.” We drove in Victoria’s convertible merc to a strip mall. “Over here baby,” she said and held the door for me as we went in. It was some kind of health clinic. “Do you have an appointment,” the lady behind the desk asked. “Yes we do,” said Victoria, “it should be under Sasha.” She mentioned to me as she said it. “Ok follow me please,” said the lady. She led me into an examination room and told me to get undressed. I waited for a couple of minutes before the doctor walked in. “Isn’t Victoria great? I’m so glad I could help her with this. Bend over the table please.” “You know Victoria?” And right then he injected something in my butt. “We’re longtime friends. Ok, 2 shots to go and then you’re done.” I had forgotten to ask what the shots were of before Victoria and I walked out the door. Our next appointment was a laser hair removal center. “Goddess, all my hair?””Everything bellow your eyebrows. Have fun, I’ll be back.” Victoria had already paid for 5 sessions I found out and sat through the procedure. I was going to miss my facial hair a little bit. Who was I k**ding p? The chance to live out my dream with the help of someone as hot as Victoria was everything I’d ever wanted. I came out after my session to find Victoria in the car waiting. “We can’t start you tanning until after the laser treatments are done. Otherwise we’d be heading there next. I got you some clothes. You will put them on at our next stop.” The next spot turned out to be an all inclusive spa. We walked into the lobby. “Hi, I made an appointment for 2. We’re Victoria and Sasha.” The young girl behind the desk raised her eyebrows and then handed us our itinerary. Victoria read it aloud, “first we’re doing mani/pedis because you’re going to have to keep up wi this now. What color should I get you? I’ll decide later. Then, you’re getting those nasty eyebrows waxed and shaped. Then we’re going to do something about your hair. Any questions?””Can our nail polish match?” Victoria laughed. “I knew I made the right choice to do this. Yes babe, we’ll both get sparkling neon pink.”The mani/pedi went fine. The lady doing my nails didn’t believe me at first when I told her what color I wanted, but went on with it. I must say they looked fantastic. For the longest time I resented my small delicate hands. Now I was grateful for them. Next was waxing my eyebrows. Victoria sat next to me when the lady came in. “I want them as high and thin as you can possibly do,” Victoria asked. “Are you sure?” Asked the wax technician. “Yes please. They’ll look so good in a pencil line high arch,” I said surprised at the words I had just uttered. My eyebrows came out looking so fem and cute, just how we wanted them. Finally, it was my turn to get a haircut. “Actually, we are going to put in extensions today,” Victoria informed me. “We want your real hair to get shoulder length.” When I was finished I had stunning dirty blond hair that had bug curls in the ends which fell just bellow my shoulders. “Sasha, you look incredible. Do forget to change and I’ll see you in the car.” Victoria handed me a small bag and walked out. I went into the bathroom bursa escort and took at my new clothes. A high waisted thong in electric blue, knee high socks, short shorts, and low cut long sleeve shirt. I had just taken my clothes off and almost reconsiders when the door opened slightly. It was Victoria. She scooped up my men’s clothes and quickly left. Leaving me with on other choice of clothes. So I put them on and walked out to the car. “Let’s get you home Sasha. You’ll be so excited about your new home.” I was pretty excited and very euphoric. Victoria opened the door to her guest house when we arrived. I had never seen a place more girly in décor. Everything was woman centered. Victoria led me into the bedroom. “Baby, I’ve gotten you some clothes that should last you until we can go shopping again. I got you your own computer too. You’ll be putting it to good work trust me. Good night my lil tranny superstar.” And with that Victoria left. I was insanely horny from everything that had transpired. I jerked off and came 3 times before I went to sleep. “Rise and shine lil baby,” Victoria pulled back the curtains and let the sunlight through my room. “Come on we have a lot to do today.” “I’ve been meaning to ask you. What did the doctor give me in those shots?” “Baby, in 3 months it will become very obvious. Now get dressed. She watched me as I pulled on a neon yellow thong, cut off short shorts, and a tank top. “You are going to be such an amazing woman.” Our first stop was a tattoo parlor. Victoria knew exactly what I was going to get. “We need her tongue, ears, and belly button pierced. After that she’s getting a couple tattoos.” She held up her phone showing them an ornate tribal pattern with stars in it. “We want this on her lower back.” She swiped to the next picture it was two words in script with hearts that read “forever limp”. This one guest above her little clitty. I wasn’t even embarrassed. I was just amazed how much Victoria was taking control. The tattoo guy went away to draw up the tattoos and get ready. “Victoria, why would that tattoo say ‘forever limo’?””Because it will come true in the next couple of days. One of those shots the doctor gave you is an anti androgen. It’s usually meant for prostate cancer but in this case it’s going to give you a much needed shift in hormones.” I looked at her speechless. “I know it’s a huge fantasy for you. You’re welcome baby. He also gave you depoprovara and estrogen. Your breasts are going to look so amazing baby. You’ll be curvaceous finally. You’ll get hips and a bigger ass. You don’t mind do you Sasha?” “That sounds perfect to me. Can I get implants?” “Of course babe, but we want them to develop a little first so they aren’t stretched so tightly when their done. You’re getting DDs btw.” The tattoo guy walked back over. “Come with me please and lie down here.” I spent the next 6 hours in that chair in some position or another. We were right by the window too so the whole time I was getting my tramp stamp everyone who walked past saw my thong sticking out. Which was the least of my worries. I now have 2 permanent markings that forever brand me as feminine. “Baby, they did an amazing job on you,” Victoria hugged me and we walked to the car. My back was very sore after all the tattooing was done. Victoria had brought jewelry for the piercing people to use. I had 3″ gold hoops in my ears, a dangly rhinestone cherry belly button ring, and a glow in the dark tongue right with “69” written on top of it. I was pleased with how I was turning out. “I feel like I’m meant to do this,” I said. “Baby you were.” We drove to what looked like a department store, but turned out to be a giant sex shop. “I’m going to get most of your clothing here. No need to dress you up in anything but lingerie and club wear, right?” This place had everything. We walked up and down rows until our kart was filled. Dozens of pairs of thongs, almost all of them rode really high up like over the hips, garter belts, micro skirts, fishnet tops and dresses, several thong bikini sets, and all sorts of costumes.”You might not like this Sasha, but do you see that dildo over there?” She was pointing at one called Bam. “Yes,” I nodded. “Babe, it’s 3″ wide and 14″ long. By the time you’re ready that should slide in and out of you as easily as 1 finger.””But why? I’ll be so loose then.””Nothing is hotter than a ginormous dildo slamming into a tiny limp dicked tranny. Especially if I’m slamming it in.” We picked out several different size butt plugs and dildos. “You will wear a butt plug almost all the time now. Understand?” I nodded. Later we checked out and the cashier said, “your special order items are ready today. We’ll bring it out to your car for you.” “Thank you so much,” Victoria said leaning over to give him a long look at her perfect tits. We walked to the car and a clerk met us there. I helped him put the 2 large packages into the trunk. “You’re shoe’s untied Sasha,” Victoria said. I knew what she was getting at. So, keeping my legs strait I bent over at the waist to reach my shoes all while the clerk stared in almost disbelief. I knew for sure my thong was sticking out high when I heard Victoria’s phone take a picture. “Let’s go babe,” she said. As we drove I asked, “what’d you get?” “It’s going to be your new best friend. One is a fucking machine to bursa escort bayan give your boy pussy the work out it needs. The other is called a sybian. It emits very intense vibrations. You’ll love it.”We got home and unloaded the car. “Strip,” Victoria commanded. I did so she knelt down and spit in her hand. Then she produced a cage out of one of the bags. It was extremely short. She proceeded to put me into chastity and locked up the cage. “Babe you have the tiniest little dick I’ve ever seen. This cage won’t be necessary in the near future, but I cannot allow you to cum like a boy. From now on you can only cum for being fucked in your sweet ass. Now, I’ve wired up the room so that there’s a camera shot of almost every angle in here. There’s a microphone in the ceiling too. You need to start making videos. You’ll start solo and then we’ll work in other people. Now, show me how you fuck yourself.” Time started flying by it seemed. We’d go to the spa twice a week. I was on my final laser hair removal by now. It is so nice not having to worry and shaving or stubble. I was going to be completely smooth the rest of my life. My hair was now my own. I still did it in big curls and dyed it a lighter blond than it is naturally. I hardly noticed my clit not getting hard anymore. It was so shriveled and limp that I had trouble tucking sometimes. The sybian was giving me all the pleasure I needed. When I rode it cum oozed from me in an almost endless stream. When Victoria was there to watch me shed catch some of it in her hand and make me eat it. Wearing increasing size of butt plugs was catching up to my goal. I still needed lube but that 3″ diameter giant slid in and out of my ass now as fast as the fucking machine could go. It felt incredible. And looked even better. On the screen you’d see me with my long blond curls get in a doggie style position and get blasted by the toy on the end of the machine. Watching the videos later I couldn’t believe how flat my ass was when I first started to where it was now. The tramp stamp above it really accentuated my new hips and curvaceous ass. Then, one day we wee out running errands when I noticed we’d driven to the doctor’s office. “I wanted to sunrise you so here it goes,” Victoria said as we walked in. We both were taken into the waiting room. I stripped down to my matching black bra and thong. My breasts were not large by any means but clearly there. They’d been growing little by little over the months. It was nice not having to pad a bras completely now. The doctor came in. “It’s so great to see you two. Victoria, you look stunning. And hello to you Sasha. If you wouldn’t mind bend over the table for me.” I did and received a shot of estrogen, provera, and anti androgen in succession. “Ok, Sasha are you ready?” “Of course,” I said totally unaware of what was coming. “Your breast development is going well it looks like. These are the implants we’ll be using.” The doctor held up 2 enormous breast implants. He handed one to me. It was firm yet squishy. Kind of like a gummy bear. “These will go under your pectoral muscle so that they stay high and perky forever. We’re also going to feminize your face today as well as a few other things I’m sure Victoria’s told you already. Now if you’ll put on his gown a nurse will be in here shortly to take you into surgery.” This was an amazing surprise. Gave Victoria a happy and excited look. “You’re so amazing Goddess. Thank you so much for doing this all for me.” These were the last words I said before being wheeled off into the operating room. In addition to the breast implants my face was feminized, my Adam’s apple shaved, and my lips injected with collagen. I didn’t need an liposuction mostly thanks to a d**g Victoria had been giving me. It turns on the pigment in your skin so that you become and stay very tan easily. As a side effect, you almost have no appetite. It took several weeks before I was fully recovered. I dare anyone to point to where the incision was made for my implants. My breasts turned out as spectacular as Victoria’s. They could barely be contained in my bikini tops now. I almost didn’t recognize myself in the mirror now either. I looked 100% a woman. Tanning had been one of my favorite past times. I’d lay out in the middle of the yard for about 2 hours every day. I was very careful to wear the same high waisted thong bottoms and matching black halter top. I loved that everyone from around the neighborhood could see me. Every now and again someone would honk from the high road that went pass higher on the hill from our house. I loved it. The attention I was getting now was amazing. Like I was living in a dream. I had the deepest thong bikini tan lines that accentuated my now giant round ass and wide hips and on top I had a pale pattern from where my bikini top held my DDs. I was tanning one afternoon when Victoria got home. “Hey baby, We’re going to a friends house and a photographer is going to take pictures of you.” “That sounds great. Why do I need pictures taken?””For you website silly. Did you forget you’re going to be a porn star?” I almost had forgotten to be honest. “What do I need to bring?””I already packed for you and got you so,e new accessories,” Victoria said handing me an overnight bag. “You’re the best baby,” I said and we drove off. The photographers house was a escort bursa mansion. We greeted each other and he instructed me to wear whatever I felt was most elegant and naughty. I slipped on a hot pink thong that sat above my hips along my tan line. I found a matching halter top in the bag and tied it on. God my boobs were huge. Victoria had given me a silver body chain for around my waist, a new shiny belly button ring, a rhinestone choker with matching bengals, ankle bracelet, and earrings,and two platinum rings molded to have a heart on top of them. In the bag were hills that only a stripper would wear. The clear platform ones. They looked so good on me. I’d been practicing wearing heels for awhile now and had not trouble in these. Even if the heel was 6″ high. The shoot was going very well. Victoria looked very proud for me. Even the photographer said I was a 10. I loved doing my sexy poses showing off my tits and flaunting my ass. I even love how tiny my dick is now. There’s probably no way to wake it up while I’m on these injections. And in reference to my big round ass and huge tits my cock looked extremely tiny. I made sure to point out my tattoo for many of the shots. “How adventurous are you,” the photographer asked me. “I’m game for almost anything,” I answered. For some reason then the sound of my own voice hit my ear and I was delighted to hear a soprano effeminate voice coming out of my mouth. “I want to take some shots of you in a very public place so we can get people’s reactions in the shots.””Sounds great,” I said. Victoria came with and we drove to the beach side board walk. I had on one of my most scandalous outfits. Black cotton/spandex Shorts that were so short you could see the underside of my butt cheeks and that were so tight they rode up my ass crack making them very clearly outlined. Underneath I had a reflective yellow thong that rode way higher than the shorts. I had a matching yellow string bikini top underneath a black baby tee that ended about 3 inches bellow my breasts. I had on just as much jewelry and a pair of platinum platform heels on. Just by walking I saw people’s heads turn. Victoria was next to me when we stopped near a substantial crowd. It was about 50 college age k**s on spring break. Victoria dropped her keys in the ground. On cue, I stuck my ass out and slowly dove forward showing off my boobs as I reached down and picked up the keys. I knew our photographer had been snapping pictures but until I stood up I hadn’t realized almost everyone was staring at me. Several of the guys kept trying to talk with us. Of course they were very interested in an aspiring pornstar. I was loving it. I pulled my shorts down and let everyone take a turn slapping my ass. I kept flashing my tits too I was so comfortable. I stripped down to my bikini and got some pictures that were worthy of sports illustrated. It got dark and we went back home. The pictures turned out amazing. Seeing a whole circle of people around me while I am bending over will never get old to me. In a couple more weeks my site was up and running. Victoria and I put my videos all over the web. I was getting tens of thousands of views per day. Victoria interrupted me one afternoon as I was laying on my back taking a humongous dildo all the way in and back out with the fuck machine. It was so effortless now. “Sasha baby, who’s your favorite male porn star?” She already knew when I said, “Mandingo,” without hesitation. “I’ve just booked 5 black guys for your first gang bang. I couldn’t get Mandingo, but trust me these guys are huge. The smallest is 8″ and one guy is over 12″. Are you ready? This is your last step to becoming a real porn star.” “I can’t wait,” I moaned as my limp clit spurted another stream of clear jizz. “I know you’ll do great. Most of it’s going to be double penetration just so you know. Come over here.” I had taken the dildo out of my ass as she was talking and slid over towards her on the bed. “Get on your hands and knees baby,” Victoria commanded. I presented my ass to her. I turned my head to the computer monitor and could see us perfectly framed on camera. Victoria covered her hand with lube and pushed her fingers into my ass all at once. My ass gobbled up her fist with ease. She drew her hand all the way out before stuffing it in me again to the elbow. She was hitting my prostate in the best way each time she penetrated me. The started to go faster and faster with her pumping pulling her fist all the way out each stroke. Even from where I was I could see my hole was gaping. “Put your legs over your head,” Victoria said. I did so in a way that my dick was inches from my mouth. If I was any more of a man I could’ve sucked my own dick. Victoria kept giving it to me. The pleasure felt like it was emanating through my whole body. I saw some cum start to dribble out of my cock. The dribble of cum kept getting thicker as Victoria worked my ass. Rope after rope of clear cum fell out of my cock right onto my face until it was covered. This lasted about 20 minutes. “That’s enough for you now baby,” Victoria said giving me one final stroke causing another rope of fluid to land directly in my mouth. “I want to tell you something else. You’re going to be on tv. I was interviewed for an HBO series and furnished them with your complete transition. It airs tonight. I told them it was ok to use your real name and talk to people from your past. I hope you don’t mind.” “Of course not. There’s no point in hiding this now. We put in too much work for it not to get attention. I love you Victoria.””I love you too Sasha.”

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