Lipstick & Miniskirts

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Lipstick & Miniskirts Page 62

by John Dylena


  He stepped into the hallway and she walked up to the entrance door and locked behind him. “Why did you lock it?” He asked.

  “Security. I have a fair amount of cash behind that desk, and since I am the only person working here, I can’t keep watch over every part of my operation here.” He followed her into the room. “Ok sit here” she said, motioning to the red velvet chair. She sat down opposite him., Between them was a wooden table, and scattered across it were documents.

  “Right, let’s get on with it shall we?” she said, cracking her knuckles.

  “What time is your next appointment?” he asked.

  “2:30pm, why?” Her eyes were still on the paperwork in front of her.

  “Here’s ten-grand. I’d like to reserve you until then,” he said, setting a manila envelope on the table.

  She looked up from the papers and smiled. “Well then, what can I do for you… or to you?” She picked up the envelope and peeked inside.

  “Well, I was hoping you can enlighten me. You see, I've recently come across something that has been bothering me for some time, and after thorough research I have decided that someone of your particular… specialty… can help me.”

  She frowned. “So you’re paying me ten-grand for a philosophical debate?”

  “Basically… yes. If you’re not comfortable with that, I can go to another person,” he said.

  “Oh no, you have me wrong. It’s been a long time since I've been able to have an intellectual conversation like this. Most of the time it’s all about physical pleasure. So enlighten me to your ‘predicament’, and we’ll see if I can help.”

  He sat up in his chair, his hope restored. “Right, so I was on the internet some time ago and I discovered that it has been said that a man’s greatest fear is becoming a woman. And I’ve been thinking, why is that so scary? I mean, there are some people whose lives won’t be any different if they were a man or a woman, then again, some would be drastically different. Me, personally, I consider myself the former and was hoping someone like you can give me your perspective on this, seeing as you’re a woman who is also skilled in knowing what a man wants and desires.”

  The room was quiet. The awkward silence unnerved him.

  “You know what, follow me, you deserve to be ‘enlightened’ in a more comfortable setting.” She stood up and led him out of the room back into the hallway. There were several rooms on either side, and a big doorway at the far end. He followed her down the hallway and stopped in front of one of the doors. She unlocked the door with one of the many keys on her key ring. It opened to another hallway, smaller than the one they were in. At the end was a large pair of wooden doors, which also required a key. She turned the brass knob and entered into a big lounge area furnished with a bar, big comfy couches, a fire place, and a staircase.

  “Sit,” she said pointing to one of the couches. “Thirsty?”

  “No thanks, I'm good,” he said. “Where are we?”

  “This is the lounge, where my VIP guests get to relax and wait for their sessions. That door leads back to the entrance, and that staircase leads to my office.”

  “Oh nice,” he said looking around. When she was finished making herself a drink, she sat back down on one of the couches next to him. She took a sip of her drink, then set it on the glass table.

  “Now, where were we… oh yes, you asked for my point of view on the question of whether a man’s greatest fear is becoming a woman.”

  “Correct.”

  She cleared her throat. “Well the thing is that a woman’s life is not the least bit easy, and it doesn’t matter whether you’re attractive or not. Take the unattractive woman, one who perhaps is overweight, maybe has bad skin or terrible hair. She will constantly be under the scrutiny of those typical ‘rich cheerleader’ types, follow? They will be tormented by both outside and inside forces for not being what society has deemed ‘attractive’. But then there is the opposite end of the spectrum: the drop-dead gorgeous women, those who set the bar. Their life isn’t easy either; they gain a lot of attention, both good and bad, but mostly unwanted attention. Those women are under constant stress to keep their appearances up, and because of it are most likely to be sexually assaulted, harassed or even raped. They never get taken seriously if they try to get anywhere in life. You said yourself that there are men who if they somehow instantly became women their lives won’t be any different, and others whose lives will be drastically different, correct?”

  He nodded.

  “Well, I’d like to add to that. Imagine you take a group of men, and turn them all into women. I believe there will be not two, but three outcomes. The first one: some of them will be overjoyed and excited with their new bodies. They will eventually give into their bodies’ urges and any trace of their previous male subconscious will be gone. They’ll become hookers, prostitutes, strippers, escorts, etc. The second outcome: there are those who, like the first group, are ecstatic when they receive their new bodies. The difference is they learn to respect and control their new urges and use their heightened attractiveness to get far in the world. They become those you see on the top 10 hottest CEOs, presidents and VPs of companies, doctors, politicians, etc.

  “And then there are the unfortunate. They are the ones who dread their new bodies and long for their muscular, hairy, rugged bodies and of course their dicks.” She stopped and let her words sink in. Moments later, she continued. “I gave you my opinion on the subject, now it’s time for you to tell me why you think men fear becoming women.” She stood up, straightened out her leather outfit and sat back down, crossing her legs.

  He was caught off guard. He expected her to tell him everything he needed to hear and not have to explain himself. “What you told me was enlightening, but I feel the reason why men fear becoming women is well, no offense… there are men who see women as the weaker sex, whose sole role in life is to be submissive and do what the man tells them to do. They stay at home and do all the housework, chores, and take care of the kids, while the man brings home the money and is allowed to have all the leisure time he desires. From what I read, some men fear becoming a woman because the presence of a vagina signifies weakness and submissiveness.”

  “Interesting. Very interesting,” she said. “You are partly right on that concept. In my line of work, I have seen my fair share of men who see it that way. I have had wives and girlfriends drag their SOs here so they can be forcibly feminized. Heck, I've even seen men come in here—purely voluntarily—and asked me to doll them up and turn them into prostitutes. Both ends of the spectrum and everything in between. I've seen men break when they are made into women. I've seen the toughest and most burly men give in and become sissy sex slaves. One thing I have yet to see is a person ask me to turn them into a woman so they can experience life that way. Every client I have had came in for purely the physical pleasure, never the mental or emotional pleasure, they just want to be butt-fucked with a 10” dildo.” She spoke plainly, leaving Reed speechless.

  “Wow. I’ve never… ”

  “You said it yourself that if you were to become a woman tonight, that your life wouldn’t be any different, correct?”

  “Yes, but that was just a quick thought.”

  She leaned forward, taking on a more aggressive posture. “Why is that? Do you not have a job? Wife? Kids?”

  “None. I’ve had a few girlfriends, but nothing serious.”

  “How old are you? 23? 24?”

  “25.”

  “Do you work?”

  “Currently unemployed. However, now that I think about it, if I were turned into a woman last year, my life would definitely be complicated.”

  “Why’s that?”

  “Well, I sold my business few months ago, and because of it, I came into a lot of money, so I won’t be working for a while.”

  “What do you do to keep yourself occupied?”

  “Work out, video games, listen to music, watch movies… ”

  “Any hobbies?”


  “Not really.”

  “Perfect. This conversation has given me an idea.”

  “Oh? What's that?”

  “You see, what I deduced from this is that each man who became a woman would experience it differently. Each of their lives would go down a different path. Sometimes the paths will converge, but then they will separate once more. My idea, as well as the answer you have been looking for is that in order for you to come to complete absolution and enlightenment, you need to experience life as a woman.”

  “Ah. But ho—”

  “And I have the perfect way for you to do that,” she added. “You said that you’ve into a good amount of money, so you won’t be working for a while, and you have no hobbies, and I'm guessing you’re bored almost every day.”

  “What is it you are asking of me?”

  “Come work for me”

  “Seriously?!”

  “Yes, I told you when you arrived that I am short-staffed… ”

  “Yeah I remember.”

  “So here is the official invitation: I need a secretary/receptionist. Having one would not only make my life easier, but my clients’ lives too. All my paperwork, client’s information… everything… is jumbled and needs to get organized. Plus, having a secretary would allow me to spend more time with my clients, which would increase customer satisfaction and thus would generate more business.”

  “I follow.”

  “And this will be purely voluntary, you came into a lot of money recently so you don’t need to get paid. And thus there will be no need for a written contract. You can work for me for as long as you please… a day, week, month, year, whenever you want to stop, you just let me know and you won’t ever have to hear from me again.”

  “You seem excited about this,” he said, scratching his head.

  “I am, and from your body posture and language, you seem interested too,” she replied.

  “No I am not!”

  “Oh please, you can’t fool me.”

  “Ok fine. I find the whole idea… interesting.”

  “This would be a great opportunity, not a lot of people are given this chance.”

  He thought about it for a moment. In his mind he weighed the pros and cons. It was true that he was getting bored of doing the same thing every day, and this would help immensely. “Ok, I’ll do it.”

  “Good answer. However, there will be some ground rules and should you break them, there will be punishments.” She smiled, “and if your curiosity ever gets the better of you, I can always schedule a session for you.”

  “Uh, sure. Thanks for the… offer, I think.”

  “This is so exciting!” She laughed, “Ok look, we have an hour until my next client, so follow me to my office and I’ll get your measurements.”

  “Sure, I'm free for the rest of the day,” he said, standing up. He stood up and followed her to the staircase and up the stairs. While he was going up the stairs he looked up at her to say something, but he forgot what when he noticed he had a full view under her skirt.

  “You know, you’re gonna have to get over those manly desires if you’re going to go through with this,” she said.

  He quickly looked away. She did know how a man thinks. He blushed slightly at the embarrassment and then shrugged it off. They reached the top and walked up to two large double doors. She grabbed both knobs and turned them, opening the door to her office. “Welcome to my sanctuary,” she said, walking in.

  He was speechless. The room was fully and lavishly decorated. She had floor rugs, a large wooden desk, couches, windows that looked out into the street, as well as the lounge. There were monitors showing the feed from the security cameras, several large leather trunks, and three steel door lockers.

  “Stand there,” she said, pointing to the open area next to the desk. She went behind the desk and fumbled through some of the drawers. After a minute or two of searching she came out from behind the desk. “Ok, strip down to your undies, including shoes and socks.”

  After hesitating for a second, he began to remove his shirt.

  “Hurry up! I haven't got all day!” she ordered.

  At her command, he removed the rest of his clothes and set them aside. While he was doing that, she went back behind her desk and grabbed a small wooden box and set it on the table next to him.

  “Oh my,” she said examining his body. “A perfect specimen… not too hairy, nice build, not to muscular, thin… oh this is gonna be good. Now don’t move an inch.” She opened the wooden box. Inside were breast forms. “A modest size, but they do the job. Don’t worry, the glue is temporary. I'm putting these breasts on you so I can get accurate measurements.”

  “Ok,” he gulped. She applied a thin line of glue around the other edges of the breast forms then applied them to his chest. After waiting a minute for them to dry, she pulled out a measuring tape.

  “Arms out.” He stuck his arms out as she ordered and she measured him. “Let’s see… arm length, check… shoulders, check… breast size, check… chest, check… waist, check… hips, check… legs, check… shoe size… shoe size?”

  “Oh, 11.”

  “Right, so 10.5, maybe 10.” She wrapped the tape up and wrote down all the measurements on a notepad, then did some calculations in her head and wrote them down too. “Ok, those boobs should come off any minute now. Go ahead and put your clothes back on, and by that time they should be ready to peel off. I’ll be right back.”

  He put his clothes on, then before putting his shirt back on, he tugged at the breasts. There was some resistance but they came off easily. He set them on the table and Arina came back into the room.

  “Ok, I need you to fill this out. It’s a basic client information sheet… don’t worry about the payment, just mark ‘cash’. I’ll be done around 5pm. Come back at that time for the next phase.”

  “What do you have planned?”

  “Can't tell you,” she smiled.

  “Oh ok, yeah I’ll be back then.”

  “Good. Fill out the forms and I’ll see ya then. You’re free to go when you’re finished.”

  With that, she got up and left. When she was gone, he picked up the clipboard and glanced over the paperwork.

  “Let’s see, name, address, phone, cell phone, email, quick medical survey, other information, past mistresses, wants/desires/needs, and signature… done.” He finished, set the clipboard on her desk and left the office. He headed downstairs and out into the reception area. Not looking back, he headed outside and to his car. He noticed one more car in the lot, probably her next client.

  THE EXPERIMENT

  CHAPTER II: A NEW IDENTITY

  Reed went home and spent the rest of the day playing video games, his eyes constantly looking at the clock, making sure he wouldn’t be late for his evening appointment with Mistress Arina. In the weeks leading up to today’s encounter, he’d been to many different dominatrix websites, and they all showcased their specialties. It unnerved him, seeing men and women broken and in some cases beaten, all because deep down, they craved it and it brought them pleasure.

  As the clock neared 5, he wrapped up what he was doing and returned to her dungeon.

  “My my, 5pm on the dot. Good timing.” Arina said as he walked into the lobby.

  “Didn’t want to be late. Hate to get punished on the first day,” he replied.

  “Wait outside, I’ll only be a minute.” He nodded in compliance and walked outside. It was starting to get dark as he stood on the sidewalk, looking around. “Ok, let me just lock up” she said, coming out of the door. He looked at her while she had her back turned to him. It appeared as though she hadn’t changed her outfit, but then again, she was wearing a long coat. “Follow me.”

  He followed her to the parking lot and stopped at her car. It was a brand new, black Audi.

  “Well, get in” she said. He climbed into the passenger seat and before he could get his seatbelt on, the car was started and she whizzed out of the parking lot. The radio was set to a fami
liar station and the volume was turned up. “It’s only a short drive to the studio,” she yelled over the music.

  “What studio?”

  “My friend owns a special effects and makeup studio. He’s going to give you a new face,” she smiled. After a short drive, they arrived at her friend’s studio. There were no advertisements anywhere so it must've been a private studio. She parked in the underground parking and headed for the elevator. “Don’t worry, he’s very good at what he does,” she said.

  The elevator stopped on the top floor and they got out. It opened up to a big hallway with only one door on the other end. They walked up to it and she knocked on the door. Less than a minute later, the door opened and they were greeted by her friend.

  “Daniel!” she said.

  “Arina! How are you!” he said as they hugged. From the way he was dressed and his manner of speech, Reed assumed that Daniel was gay. “And you must be Reed, it will be a pleasure working on your face tonight.” Reed stuck out his hand, but Daniel swatted it away and gave him a hug instead. “My word, your face is so smooth. Oh Arina, you brought me a very good face indeed, and so cute too! Now come in, and Reed, you can have a seat in the chair over there,” he said, pointing to the barber shop style chair in the corner.

  The chair was extremely comfy and as he sat down he looked around the room. In front of him was a giant vanity: three mirrors and fully lit. On the counter top was a vast assortment of makeup items. There was a wide selection of wigs, most were female but there were some male wigs.

  “So, Arina said I am to turn you into a female… don’t worry, your secret is safe here. This is going to be tons of fun. She already gave me the details on the overall appearance and such, so when we’re done with the mask, we’ll try on an assortment of wigs to see what looks good on you, ok?”

  “Ok.”

  He covered Reed in a cloth then stuck two straws up his nose. “These are so you can breathe while I cover your face. Be sure to keep your mouth and eyes closed at all times and try not to move an inch, ok?”

 

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