Becoming Belle : First Time Feminization

by Ava Hayes

  “You- so wait -you’re actually a man?” I said in disbelief.

  “Well that’s not the way I prefer to look at it.” she said sounding slightly offended.

  “You’re right. I’m sorry I shouldn’t have said that. That’s not what I meant at all. I’m just surprised. I don’t think think this is the right job for me.” I said setting my drink down and getting up. “I’m sure it’s a good job and I bet you’re a great boss but I just don’t think it’s right for me.”

  “Tom sit down. I didn’t bring you all the way out here to have you back out of the room like a frightened schoolchild at the mere sight of my private parts. This is a negotiation. You’re free to do whatever you like but after this morning I think you owe it to me to at least hear me out. Do you know how much this penthouse costs?”

  I looked around. “Oh god. I have no idea. Millions? Ten million?”

  “Twenty Million. It’s one of the five most expensive penthouses in the city but I don’t care I can make twice that in a year. How much did you earn at your old job? Per year?”

  “Well I didn’t last a year but maybe $30,000? slightly less I suppose.”

  “Imagine earning that every month working only a few nights a week and all you have to do is dress up pretty and spend time a little time with a handsome interesting man.”

  Thirty grand a month? That was insane. No matter what I could never hope to earn that kind of money . This whole situation was insane. Could I really go through with it though? What would I even look like?

  “I don’t know. I’ve never done anything like this. I’ve never even had a one night stand. Not that I’m against the idea but people just don’t really look at me that way. What makes you think I could earn that kind of money if I can barely give it away for free?”

  “As a man, sure. But give me an hour alone with you to do anything I want and you’ll see yourself the way I do.”

  My mind was buzzing with a million thoughts. I was uncomfortable, nervous, a little flattered, but most of all frazzled. Each of these thoughts bounced off the number 30,000 like a pinball hitting a target. How could I do something like this? But on the other hand how could I say no? I was 21 now. With that kind of money I could retire by the time I was thirty.

  I was turning the idea over and over in my mind rationally but there was a tiny part of me that I never knew existed. A part of me that was turned on by the idea. A part of me that wanted to get dressed up in sexy clothes and a wig and have a handsome man pay attention to me. To take me on expensive vacations and take me out to fancy restaurants and give me lavish gifts.

  I just couldn’t push the thought out of my head that it wasn’t me. It wasn’t something I’d do. I expressed the idea to Victoria as we sat down to dinner. I’d slammed my drink shortly after she mentioned the idea to me and she brought me another. The food smelled amazing and I suddenly realized I hadn’t eaten all day. I dug in. The fish was mouth watering and the side dishes were all equally amazing.

  “I agree. This isn’t something you would do.”

  “You do?”

  “Yes. And I see your life as that man. A man with no ambition and no direction. You moved all the way across the country for a job that barely pays you enough to live on. You live in a shitty apartment in a boring suburb with no prospects and no relationship. That’s the kind of life that the kinds of choices you make have led you to. So my question is why do you keep listening to that voice inside your head? Why are you listening to the voice that has led you to this point in your life. Don’t you want to make a change?”

  Everything clicked. What she was saying was exactly right. What was I going to do just keep making the same choices over and over that got me into this situation?

  “Here’s the deal and it’s a one time offer. If you walk out that door the deal is off the table. I want you to let me dress you up. I want you to go with me to meet a client. This is my date you’re not obligated to do anything other than tag along. If you do this with me I’ll forgive the accident. If you actually do a bit of work tonight I’ll pay you for a normal night’s work. Three thousand dollars. Enough to not have to worry about rent for a while while you find a new job. You can decide at the end of the night if you’d like to continue working for me.”

  That was a deal that was too good to pass up. Completely forgiving the accident debt just for playing dress up for a night and going with her on a date. It might be a little humiliating but nothing compared to paying off twenty or thirty thousand dollars in damages.

  “Okay it’s a deal.” I said finally.

  CHAPTER 4

  We finished our dinner and Victoria led me upstairs. We entered a room with big double doors that she called her ‘closet’. It was three times the size of my entire apartment. I finished my cocktail and started on a third.

  “My you sure are thirsty.” Victoria said laughing.

  “Yeah something like that.” I said.

  Her so called closet was absolutely astonishing. It looked like a store. There were clothes on hangers lining the walls and wooden stands with expensive designer shoes sitting atop them. There was an entire wall of handbags.

  She turned to me and said “What can I say? I love to shop. And it’s good for business. I have to keep my girls looking good.”

  She led me to a drawer near the edge of the room that was full of lacy panties and bras. That’s when it hit me that I was really doing this. She scrutinized a few pairs before deciding on a silky black thong.

  “Okay, time to pop those off.” she said pointing at me slacks.

  “What here? You want me to do it in the middle of the room?”

  “Here’s as good a place as any. I showed you mine now it’s your turn.”

  Well if I was doing this I’d better do it. I turned away from Victoria and pulled my pants down around my ankles.

  “Those too.” she said pointing to my boxer shorts.

  I sighed turned around and let my boxers fall to my ankles.

  “Come on now don’t be shy. Let’s see what we’re working with here.” she said.

  I turned around and Victoria audibly gasped and put her hands to her mouth concealing a smile and giggled for the first time. She looked at the tiny silky black thong in her left hand and threw it aside then began searching for something a bit more accommodating.

  “Well that complicates things a little bit but it’s not a problem. I’ve got to say I was not expecting that. No offense but who knew that a man like you was such a man.” she frowned while looking down at my inconvenient member. Then she reached into the drawer and pulled out a strange strap. It was like underwear but a bit different.

  “We need to get you into this.” she said pulling it up around my waist. She grabbed my cock as though it were the most natural thing in the world to do, I definitely wasn’t complaining, and stuffed it into the pouch. It was like a hard shell that held my cock back and minimized it’s size. When she took my cock in her hand I got really turned on and began to get an erection. She looked up at me and said “Whoa there tiger. Save it for the job.”

  After she had my cock securely fastened away she pulled out a different lacy black thong. It looked very similar to the other one but was large enough to conceal my encased manhood. The string slid between my ass cheeks. I found it really uncomfortable at first but the more I walked around in it the more I got used to it. Even beyond that I started liking it.

  She opened another drawer and this time she pulled out two plastic bags filled with silicone.

  “What the hell is that?” I asked.

  “It’s going to make your breasts look natural.” she answered.

  My breasts? I guess I was going to have to look every bit a woman and that included having tits. She found the bra that matched my panties and I slipped my arms through the straps. She clasped it in the back and slid the big cool packets into the bra. The cold made my nipples stand up.

  “We’ll come back here after we fix your face.” she said leading me
from the room in just my lacy panties and bra. We went into the next room and there was vanity with lights around it and a vast array of makeup neatly arranged around the desk. She beckoned me to sit in the chair and then immediately went to work. She had a series of small compacts and she took them out one by one.

  First she took out some kind of cream. She used it to sharpen some of my features and soften others. It also made my skin look great. Then she dabbed a brush into a pink powder and brushed my cheeks with it. Next she took out a pencil and lined my eyes with a dark eyeliner. The final touch was a tube of pink lipstick. She told me to pucker up and then expertly applied it. She combed my hair back and laid a ginger wig atop my head then fussed with it.

  The face staring back at me was unrecognizable. I could not accept that it was me. The big luscious lips, the gorgeous face, my long red hair was so convincing as were my big tits. I was so… attractive. It was the first time in my life I’d felt that way. I tossed my hair from shoulder to shoulder and smiled at the mirror in a coquettish way.

  “You’re actually getting into this.” Victoria said.

  I looked down sheepishly. I’d been so wrapped up in myself I’d honestly forgotten anyone was there.

  “No don’t be embarrassed. Use it. There’s no shame in liking the way you look. I hated my looks before too. But I changed and now I am the absolute best version of myself that I could possibly be. I wouldn’t change anything about who I am for the world.”

  She led me back to her ‘closet’ and picked out a dress. She settled on a slender black Louis Vuitton dress with. She picked out a sapphire necklace and matching earrings with it.

  “Careful with the jewelry. It’s worth more than the car.” she said with a wink.

  I checked myself out in a full length mirror. I couldn’t believe it. I was a fucking 10! This was all so unreal. It was like I was dreaming. None of it made any sense. My confidence instantly shot through the roof. I had never had any desire to dress up like a woman but after seeing how I looked I was eager to show off for the world.

  “My god!” Victoria said “You are more gorgeous than I could have possibly imagined. I mean I thought you’d be hot. I thought you’d be hot enough to make a living but you’re like A-list hot. You’re like one of the girls I call when a foreign leader requests a companion.”

  “Holy shit really? Does that really happen?”

  “More often than you’d think.” she said shrugging.

  “So what are we going to call you?” Victoria said cradling her chin with her hand and tapping a finger on her cheek. “Tom won’t do but I like Belle. Tom Belle you will henceforth be known as Belle Thomas.”

  “Belle Thomas.” I said. It had a nice ring to it.

  I did a twirl in front of the mirror and made faces just to see what I looked like when I was happy, surprised, interested, upset.

  “Well look at the time. We need to go.” Victoria said.

  “Go where?” I asked.

  “You’ll see.”

  CHAPTER 5

  By the time we’d finished getting me ready it was nearly 9:30. The sun had set and the city lights were twinkling like a sea of diamonds. We rode the elevator down to the parking garage where the same black Range Rover was waiting for us.

  “Good evening Felix.” Vanessa said to the driver as he opened the door for her.

  “Good evening Ms. Slate. You look lovely tonight. And so does your friend.” he said smiling widely at me. I could tell he had no idea who I was.

  When we were in the back seat he got in and closed the door then we were off to our destination. I still had no idea where we were going but I soon found out. The drive was a short one. After only about fifteen minutes he dropped us off at the most expensive and luxurious hotel in the entire city.

  We got out and strode through the entrance. I could feel the eyes of men and women alike staring at me as we walked into the lobby. I turned more heads in a single minute than I had my whole life prior. Victoria’s heels clicked on the marble floor but I wasn’t ready for them. I was likely to break an ankle and give the whole game away. She found me a pair of Louis Vuitton flats to match the dress. They were elegant and stylish enough.

  We rode the elevator up to the top floor. There was a fancy bar on the top floor with stunning views of the city but I’d gotten my fill at Victoria’s place. We both sat down at the end of the bar. I started to order from the bartender but Victoria stopped me.

  “There’s no need for that” she said.

  We waited less than a minute before the bartender brought us two martinis.

  “Courtesy of the gentleman over there.” the bartender said gesturing to a chubby older man sitting by himself in the corner.

  “Who is that?” I asked. “Is that who we’re meeting?”

  “Him? No. I have no idea who that is.” she raised the glass to him in acknowledgment then turned back around.

  We chit chatted for a few minutes before an handsome older man in his late thirties or early forties sat down. He had a square masculine jawline and a toned fit body. A thin beard, more of a five O’clock shadow, covered his face. His short sophisticated hairstyle was flecked with gray. It made him look more dignified. There were lines at the edges of his eyes but they just added character to his face.

  “Victoria you look fantastic tonight.” he said as he took a seat next to her. “Is this your friend?” he said motioning to me.

  “Yes this is Belle. Belle this is Mason.” Victoria said. He took my hand in his and gave it a kiss.

  “You look beautiful tonight as well, Belle. I assume you’ll be joining us?”

  “She might be.” Victoria said but her tone said don’t get ahead of yourself.

  We all got to know each other as we finished our drinks. Mason ordered a bourbon. He was an investment banker who used to be with a big prestigious firm but had recently struck out on his own. “No risk. No reward.” he said.

  After about ten minutes he said “Would you ladies be averse to taking this party back to my hotel room?”

  “Not at all. Lead the way.” Victoria said following behind him.

  My palms were starting to sweat. Were we going to do what I thought we were going to do? This sure seemed like the moment where if anything were going to happen it would. We got onto the elevator and we went down one floor. His room was huge. It seemed like this might actually be a semi-permanent space for him. Maybe it was his love nest?

  There was a record player by the wall. He put on an old upbeat piano jazz record and fixed himself another drink. He offered the two of us as well. Victoria declined but I accepted. My nerves were so frayed. I was excited that he found me attractive. Excited to have the attention of a handsome rugged man but at the same time it was still all so new to me. I couldn’t tell if I was actually attracted to him or if I was just feeding off the attention. I’d never had any kind of sexual feelings for a man before, the idea of it repulsed me, but now that I was dressed as a woman I was desperate for his attention and he was more than happy to give it.

  Mason inched closer to Victoria throughout our conversation. Before long I noticed she was rubbing a hand on his thigh. He smiled at her and did the same running a finger in long strokes up and down her leg. After a certain amount of flirting and caressing Victoria looked at me and said “Do you want to see how we like to have fun?”

  She dropped to her knees and pulled her hair back then undid his belt, buttons, and zipper. I was so taken aback by the suddenness of it all.

  “This is what he likes.” Victoria said as she fished his cock out of boxer shorts and gripped it in her fist. Mason looked just as surprised as me until Victoria licked the tip of his penis and then took it hungrily into her mouth. Then he threw his head back and moaned as he gripped the back of her head.

  It had all happened so quickly. One moment we were all talking and flirting and the next Victoria has Mason’s cock in her mouth. I watched them intently. My cock started to grow but it was held firm in its shell
. I couldn’t believe how turned on I was getting as his cock slid in and out of Victoria’s wet mouth.

  As the tingling between my legs grew I noticed that Mason was looking me over, sizing me up. Victoria was looking at me as well as she licked Mason’s big cock. I’d never had any desire to suck a dick before but watching Victoria made me curious. The tingling in my legs grew even more as she made eye contact with me then took it all the way down her throat.

  I found myself involuntarily inching closer and closer to them. It was like an out of body experience. The next thing I knew I was getting on my knees and Mason’s big dick was swinging in front of my face. I opened my mouth and closed my lips around his meaty shaft.