Alexa’s heart was pounding as she walked up to the bar at the exclusive lounge. She had never done this before, but she was excited at the prospect. She strutted up to the bar with pure confidence and sat down to a handsome man wearing a Rolex watch. She turned to him and said, “Hello”. He turned to Alexa and said, “Hi, my name is James. This might be a bit forward, but you are truly a beautiful woman.” Alexa blushed and they continued talking and getting to know each other until James had noticed an hour had passed. He apologized and said, “I really need to get going, but it was lovely talking with you. Could I get your number so that I can call you sometime?”. Alexa happily scribbled her number down on a napkin and slid to to James with a flirtatious smile.”
Later that night, as Alexa ran through the day’s events in her head, she was snapped back to reality by the ringing of her cell phone. It was a strange number she didn’t recognize, but she picked it up. It was James on the other end.
“Hey, I know we just met today, and this might be moving a little quickly, but I have a gala I’m going to tomorrow night. I was wondering if you’d like to accompany me?”, he asked.
“I would love to, but I’m afraid that I don’t have anything to wear, and with such short notice, I’m not sure I’ll be able to pick something up in time”, she replied.
“Say no more”, James said. “Just swing by my place tomorrow afternoon. I live in the penthouse at the Chestnut Towers. Let’s plan around 2?”
Alexa happily accepted the invitation. She was shaking with excitement at the idea of attending a formal event with such a rich, powerful, and handsome man. Alexa noticed the time and realized it was getting quite late, so she got ready for bed, laid down her head, and drifted off with fantasies of what tomorrow night might hold.
The next day, she woke up and went through her usual routine: take a shower, do her makeup, get dressed, and get brunch at the bistro on the corner of her block. She took her time enjoying her meal and the bottomless mimosas when she noticed it was getting close to being time to meet James, so she asked for the check and paid her bill. Then she started heading towards the Chestnut Towers. She was curious and excited to see what James’s living situation was like.
As she walked up to the building she was in awe of how extravagant it was. “Tons of rich and powerful people must live here!”, she thought to herself. She walked in, and the man in the lobby asked who she was here to see. “I’m here to see James…er…I didn’t get his last name. He lives in the penthouse”, Alexa stammered nervously.
“Ah so you’re the young lady Mr. Anderson mentioned would be coming. Please, let me show you to the elevator”, the doorman said.
Alexa rode the elevator all the way to the top of Chestnut Towers. The doors opened. There was a nervous energy flowing through Alexa as she stepped off the elevator and into one of the most luxurious rooms she had ever stepped foot in. There, sitting in a chair waiting, was James Anderson. He had a powerful air about him that was so exhilarating to Alexa.
“Good afternoon, Alexa. My assistant Phillip is in the other room with some options for you to try on for tonight. Feel free to take your time, but be sure to meet me in my room when you are finished”, James said.
Alexa walked into the other room to see an entire rack filled with extravagant dresses and another rack filled entirely with the finest and highest heeled designer shoes. Everything from Louboutin to Jimmy Choo to Valentino. Alexa was in heaven. Alexa tried on the dresses and shoes and settled on a black thigh-slit dress that was the perfect combination of sexy and classy. She decided that this would be perfect paired with a classic pair of black Louboutin So Kate heels. Once she had put on the entire outfit, she remembered that she was supposed to go see James in his bedroom. As she walked into the bedroom nervously, James said, “Wow you look amazing, Alexa. Any man would be lucky to have you on his arm, and fortunately for me, that man will be me tonight. I was watching as you tried on the dresses and shoes, and noticed that you got great joy from these expensive things. Is this a life that you would like to have, Alexa?”
“Oh this was such fun, and of course I would. What girl wouldn’t want her choice of designer clothes and shoes without a worry for expense?”, Alexa responded.
“That’s great to hear, but surely you owe something for those clothes, don’t you think, Alexa?” James said playfully.
“Oh, um, I suppose so”, Alexa stammered nervously. James stood with his hands placed on his hips. Alexa had considered using her body to get the things that she wanted but had never actually gone through with it. She was nervous but excited at the same time.
Source: reddit.com/r/eroticliterature/comments/10rz911/a_special_arrangement_30_mtf_40s_m_feminization
(2/2) Alexa walked over to James and ran her hands down his chest. She slowly got down on her knees as she ran her hands down to his thighs. She slowly caressed, making her way to the front of his pants, which had become increasingly tight. She had a smile on her face as she looked up at James. Alexa moved towards his zipper and slowly pulled it down. Suddenly, his huge throbbing penis came tumbling out of his pants and landed right in the middle of Alexa’s pretty face.
She giggled with joy as she grabbed James’s penis in her hand and slowly and gently ran her tongue from the base of his cock to the very tip, which she gave a few playful flicks with the tip of her tongue. Waves of pleasure ran up Alexa’s spine as she slowly wrapped her lips around the tip of his dick. Then, Alexa ran her lips all the way down to the base of his massive cock which touched the back of her throat. Gradually, Alexa began bobbing up and down quicker and quicker until James was pushed past his limit and climaxed in Alexa’s mouth and all over her face, ruining her meticulously applied makeup. The cum on her face felt like something to be proud of though. While Alexa had only done this once or twice, she got great pleasure from serving James in this way, on her knees.
James wanted to go further with Alexa. He began to unzip her dress. However, Alexa now became extremely nervous. She had a secret that most people didn’t know. Alexa actually had two sides, as did her body. James continued unzipping her dress. He slowly pulled her dress down to discover that Alexa not only had fake breasts glued to her chest, but also had a penis neatly tucked between her legs. This was the physical form of Alexa’s other side, Adam. While Alexa had been feeling more and more dominant in this body lately, the physical signs of Adam’s existence were still there.
Surprisingly, James let out a little chuckle. In his head, he was thinking that this is a perfect situation for him. He clearly had access to this woman he found incredibly attractive, and he had the opportunity to mold her into his dream woman, both physically and mentally. He just needed to make it so that Alexa was the only one present in this body when he was done.
James had recovered from the blow job that Alexa had given him and he was ready to start Alexa’s full transformation by making her submit to him completely. James slowly walked over, bent Alexa over the end of his bed, and slid the tip of his rock-hard penis into Alexa’s ass. Gradually, his pounding became harder and harder until he blew his load inside Alexa. Meanwhile, Alexa’s eyes rolled into the back of her head, and at that moment, any desire to hang onto Adam was fading quickly.