Lipstick & Miniskirts

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Lipstick & Miniskirts Page 64

by John Dylena


  Reed didn’t answer, he just sat there, trying to recover from what just happened. She stood him back up, pulled up his panties and straightened out his skirt.

  I felt it. I could feel the dildo inside of me…

  “Follow me.” She led him across the room to her personal vanity. “Remember Daniel?”

  “Yes.” How could he forget him? The man covered his face in plaster and promised to give him a convincing female face.

  “Good, close your eyes.” He did and she went over to her desk and picked up the box. She set it down on the vanity and opened it up. She pulled out the model head with the mask and the wig attached and set it down.

  “Ok, you’re going to feel some tugging and what not. Keep your eyes closed.”

  His eyes still closed, she removed the mask and wig and placed it on his head. She made sure there were no folds and that it was on straight. Then she turned the chair so that he can't see his reflection in the mirrors of the vanity.

  “Can I open my eyes now?”

  “Yes, but you still can’t see yourself.” She rolled a mini cart next to him and on it he could see many different types of makeup products.

  “Well, you look like a damn good woman right now, but some makeup will make it perfect.” She began the process. After some blush, mascara, eye liner, eye shadow and lip stick, she finished.

  “All done.”

  “Can I see myself yet?”

  “No, you still need one last thing.” She left and came back with the shoe box. She opened it up and revealed the shoes.

  “These are 5” black patent leather heels, the perfect heel for any secretary, with an added inch for sex appeal.”

  They did look sexy.

  She slid them on, and they fit perfectly. She lifted him out of the chair and walked him over to the full length mirror, which was turned around.

  “Drum roll please!” she said as she turned the mirror around, allowing him to see his new appearance.

  “Oh, my god,” he said. The heels were hard to stand in, and the shock of the transformation almost toppled him over. He stumbled and she grabbed him, making sure he didn’t fall. With his balance restored, she let him inspect his new look.

  He was lucky to get any words out because in the reflection was not Reed, or anything close. It was a drop dead gorgeous brunette, with the perfect figure, in a very sexy secretary outfit.

  “I can't believe this is me! I look so… so… ”

  “Sexy? Beautiful? Stunning? Feminine?”

  “Yes… all of those.” He continued to stare into the mirror. Still doubting, he made various movements and gestures and the woman in the mirror mimicked them perfectly. “This is the kind of woman I dreamed of getting with, now I am that woman.”

  “Oh one last thing.” She grabbed the velvet case on the table and showed it to him.

  “What is that? A necklace?”

  “No, better.” She opened it up. It looked like a band-aid, but it had electronic circuits on it.

  “What is that?”

  “Wait and see.” She removed it and applied it to his neck, right on his Adam's Apple.

  “Give it a second… ok say: hello my name is Reed.”

  “Hello, my name is Reed.” He spoke, but what came out of his mouth wasn’t his usual voice. Instead it was a female’s. “Holy shit! Is that my voice?!” He spouted gibberish, and listened carefully. “I have a woman’s voice!”

  “Now it is complete. Bye-bye Reed, hello Raye.”

  “Raye… ”

  She put her hand on his shoulder. “Standing in front of me is a woman, not a man, so you need a woman’s name.”

  “That does make sense.” He said, stroking his throat.

  “And since you will be working for me, there is one more thing I require of you.” She pulled out another case, this time there was a necklace in it. Except it wasn’t a necklace, but a leather collar with a gold heart tag.

  “A collar?!”

  “Yes, you are working for me, thus you are submissive to me, and therefore you’ll need a reminder should you think of acting up.” She said handing him the collar, “Put it on.”

  He held the collar in his hands and inspected it. On the gold heart tag was his name: Raye, written in a fancy cursive font. He wrapped the collar around his neck and buckled it. The gold tag shined brightly.

  “That collar also serves to cover your Adam’s apple and the voice changer… and from now on, you must address me as Mistress or Mistress Arina. Failure to do so will result in punishment.”

  “What kind of punishment… Mistress?”

  “Nice save. It starts off easy; spankings, but more mistakes you make, the worse it gets.”

  He said nothing.

  “Come now Raye, time for orientation.”

  “Yes mistress,” he said.

  God, what have I gotten myself into. But hey, this is one hell of a body!

  THE EXPERIMENT

  CHAPTER IV: DAY 1

  He followed her out of the office and down the stairway to the lounge. Walking in high heels was foreign enough, but going down the stairs was even harder. A couple of times Reed had a death-grip on the handrail, otherwise he might’ve slipped and broken his neck.

  Yea, let’s not kill ourselves on the first day. Imagine the headline!

  Doing his best to keep up with her pace, he followed her out of the lounge and back through the series of doors that ended with the front entrance. She opened the half door and motioned for him to enter the reception desk. He moved the ergonomic office chair out of the way and looked at the desk in front of him. It took a couple seconds for the scale of the clutter to sink in.

  “Oh wow,” he said, marveling at the mess.

  “Like I said, I’m not very organized.” The wall of reception desk was high enough to hide the stacks of paper from visitors. Only if you walked right up to the desk did you see the anarchy.

  “Mixed in the mess are client info sheets, order forms, tax documents, mail… everything you can think of that a small business would require. Somewhere buried there is a computer and a very nice one too. Your job is to thoroughly organize these papers as well as create, update, and organize the client info onto the computer. It will probably take you a good deal of time, hell it’ll probably take you days. Also there is a telephone buried in there. You will also be required to answer the phone, schedule appointments, inform me when clients get here, escort VIPs to the lounge, and get them a drink if they ask for it, get the mail when it arrives and sort it, as well as handling money from the clients and sending out bills and invoices. Basically everything a secretary, receptionist, and intern does. Do I make myself clear Raye?”

  “Yes Mistress,” he replied, trying to figure out where he was going to start.

  “That's what I like to hear! Now plop that cute womanly ass in that chair and get to work!”

  “Yes Mistress.” He said, sitting down in the chair.

  “I’ll come and check back on you later, then we’ll go to lunch.” With her orders given, she unlocked the front door and disappeared back into the heart of the dungeon, leaving Reed to start organizing.

  After about 20 minutes of silence, Arina’s first client of the day arrived.

  Reed’s throat tightened and his mouth dried up.

  Ok Reed, act natural. You’ve dealt with secretaries and receptionists before. What would they say?

  The man opened the door and walked up to the desk. He was an older man in his late 30s. He wore a suit and tie, as if he drove straight from his office here. He walked with confidence, showing no signs of nervousness or hesitation.

  Must be a returning client.

  “Good afternoon,” he said.

  “Hello, do you have an appointment?” Reed asked.

  “Yes I do, at noon.”

  “One moment.” Reed slid the chair to the end of the paper pile where a clipboard with the day’s schedule was hastily written. Scribbled on the paper next to the word ‘noon’ was the man’s
name.

  “Mister… Rodgerson?” Reed asked.

  “That’s me,” the man said, tapping his fingers on the desk.

  Reed picked up the phone and pushed the button, connecting to Arina’s office. “Mistress, your noon appointment is here.” He said into the intercom.

  “Thank you Raye, I’ll be right out.” Arina replied. Reed hung up the phone and turned to the man.

  “You may take a seat anywhere. She’ll see you in a moment.”

  “Thank you… say are you new here?” he asked, hovering by the counter.

  “Yes, I just started today.” Reed said, smiling.

  “Oh, that's nice… I like your collar, did Lady Arina give it to you?” The man pointed to his neck.

  “Yes she did.” Reed replied, playing with the gold heart tag.

  “Looks nice on you.”

  “Thank you.”

  “So, what do you do in your free time?” The man asked nervously.

  Wow. It’s only noon on the first day of being a full-time woman and I'm getting hit on. His he nervous? Am I doing that to him?

  “Well, I like to watch movies—”

  “Now now, don’t be hitting on my secretary. She may be new, but for now, she is off limits.” Arina said standing in the doorway.

  “Yes, I apologize Mistress.” The man said, turning away from Reed.

  “Raye, back to work… you come with me.”

  “Yes Mistress,” they both said in unison. He motioned to Reed before walking through the doorway leading into the dungeon. Arina smiled at Reed before closing the door. Reed was once again left alone with the papers.

  “God damn she has so many papers… but at least she’s consistent.” He said, trying to develop a system for organizing them.

  Journal Entry, Day 1:

  Well it happened today, I walked into Arina’s—Mistress Arina’s——shop as a man, and for many hours I was a woman. The transformation was slow, but man it was effective. It only took an hour, but within that hour, she put me into a body suit, dressed me up, gave me a new face and hair, and changed my voice!… oh yeah my “vagina” was penetrated by a vibrator dildo and I was hit on by one of her clients.

  I spent the entire day organizing her papers and man, I am not even halfway through sorting them all! Fortunately I was given a lunch break. During that break I went through a crash course on how to walk, talk, and act like a woman. Then she gave me a purse, complete with emergency makeup kit, tampons (yes, tampons), and a fake ID for my female persona, Raye.

  So basically I put my wallet and keys in the purse and we left for lunch. Yes, I had to go out in public dressed in my secretary outfit. We went to this restaurant and I had to order a salad, but fortunately she was more lenient with the drinks. The whole time I felt like I was being looked at, so it was awkward, and I wanted to get back to her dungeon ASAP. In the car ride back, she reassured me that I’ll get used to it… hopefully I can.

  The rest of the day was spent organizing papers; I had to answer the phone a couple times, schedule some appointments, and greet her clients. One of them was a VIP, so I had to escort him to the lounge and get him a drink. He spelled it out to me when he ordered it, which made making it easier.

  When 7pm rolled around (her weekday closing time) she walked me through the undressing process. Remove makeup first, then collar, voice strip, mask, clothes (which she had me put into a special hamper), shoes, which I had to put back in the locker. I’ll probably be wearing those again…… which I don’t mind. The whole thing has got me intrigued, and I’m honestly looking forward to dressing up again. After the clothes came the body suit, which was surprisingly easy.

  She told me that before I come in tomorrow, I have to shower and shave my arms.

  Tomorrow is going to be another interesting day.

  THE EXPERIMENT

  CHAPTER V: LAST MINUTE ADJUSTMENTS

  Waking up early, Reed eagerly dragged himself out of bed. He jumped into his shower and shaved, preparing himself for another day at work. In the back of his mind, he was still worried at the fact that he was excited to go to work, where he would turn himself into a woman and work as a secretary at a BDSM dungeon.

  “Good morning Reed.” Arina greeted him as he walked into the lobby. She was sitting in one of the chairs, reading a magazine.

  “Morning,” he said back.

  She looked up at him from behind the magazine. “Morning… ?”

  “Oh, good morning Mistress.” He replied, praying he wouldn’t get in trouble.

  “I'm gonna let that one slide,” she said, standing up. She tossed the magazine onto the table next to the chairs and walked up to Reed. “Let me see your arms.” He rolled his sleeves back and showed her his hairless arms. “Good, good, you shaved them. I saw you made some progress with the paperwork.”

  “Yes Mistress. There is a lot, but I expect to get it all sorted by the end of the day or tomorrow. Then I can work on digitizing them.”

  “Good, yes, I did expect it to take a while, but you’re going faster than I expected, good job. Good work earns rewards.” She winked.

  “Thank you Mistress.”

  “Now upstairs! Everything is in your locker.” She opened the door and he followed her to her office. Inside were the three lockers, however, one of them now had a placard that read: “Raye”. “That is your locker, and it will be yours for however long you work for me. Now, get dressed! I’ll be timing you! I hope to see an improvement every day. I’’ll stop the clock when it’s time for makeup… now go!” She clicked the button on her stopwatch.

  Reed quickly removed all his clothes and set them aside.

  “Neatly! A woman is never a slob!”

  He quickly folded his clothes, then opened the locker. He pulled out the body suit and began to slide it on. He stopped at his groin area and attached the vagina. He adjusted the tube, then pulled it up past his waist and up to his chest. He grabbed the breast forms and stuffed them into the body suit. He slid his arms through the holes and his neck through the neck hole. When it was on completely, he made sure there were no creases or folds, and made sure his breasts were straight.

  “A-hem.” He stopped and looked at Arina. She was holding something, but it wasn’t a pen instead something thicker: a sharpie. Then he remembered he had to insert the rectum. He gulped, grabbed the pen and bent over. He slid his hand down his crack and found the hole. He slowly inserted the marker. Arina let out an annoyed sigh, and loudly tapped her foot. He took the cue and quickly inserted the rest of the pen, then rotated it around inside. Then he pulled it out and set it aside.

  She let out a little giggle when he stood back up. He went to the locker and pulled out the shrink wrap packages and set them on the table. It was the same outfit as yesterday, at least he thought it was. He put on the bra, then the belt, followed by the stockings and finally the panties. All were the same as yesterday. Then he grabbed the blouse and put it on, noticing it was slightly different. It was fitted to show off more of his cleavage, for it was tighter around his waist as well as having a more defined V-neck. Then he put on the skirt. It was only slightly shorter, but definitely noticeable.

  “I thought your outfit needed some fine tuning. Don’t worry, it won't change any more after today.”

  He slid on the heels then walked over to the vanity and sat down on the chair. One thing he noticed was that his hips swayed more when he walked.

  “I see your movements have become more natural, and those heels don’t seem to be giving you a problem either… this is good yes?”

  “Yes Mistress,” he replied.

  It’s weird how natural this is becoming…

  He grabbed the mask and pulled it on and opened the velvet case, putting on the voice patch, followed by the collar.

  “Nice job.” She said, stopping the timer. “Now tomorrow I expect you to go just as fast including the time it takes to put on the makeup.” She sat down on the counter next to him, smiling. “Now, you will be doing all the m
akeup by yourself today, but I will be guiding you.”

  He opened up the makeup kit in front of him and proceeded, with her guidance. When he was done, she did a close inspection. “You did a good job, but there is room for improvement. If you want, I can send a kit home with you so you can practice. Now put your belongings in your purse and head downstairs and get to work.”

  “Yes Mistress,” he replied.

  She remained in her office as he walked down the stairs, navigating through the hallways back out to the main lobby. He took the keys out of his purse and unlocked the front door. Smiling to himself, he sat down in the large chair behind the counter. He surveyed the massive paperwork pile, cracked his knuckles and looked at the clock.

  “9am. Time to work.”

  THE EXPERIMENT

  CHAPTER VI: SHOPPING!

  Journal Entry, Day 4:

  Well it’s Thursday, which means I've been working for Mistress Arina for 4 days now. Each day getting ready, which she has dubbed “the process”, gets smoother and smoother. Yesterday I got dressed no problem, but it took me too long to put my makeup on, so I was subjected to my first punishment, spankings. I have to admit, while it was painful, I was slightly turned on by it; a sexy secretary getting spanked by a dominatrix. While I have had fantasies about two women going at it like that, I never thought I’d be the one dressed like that getting spanked.

  One thing I noticed is as the days go by, I can feel myself changing. I feel as though I'm becoming Raye more and more. I see things differently. When Mistress Arina takes me out to lunch, I see the world in a different way. I'm nearly done with all the paper work, and because I'm working on the client profiles, she had me sign a confidentiality contract. She sees on average 5-6 clients a day, mostly men, but some women; no one I know or even recognize. Most of them are regulars, and nearly all of them have tried in some way, shape, or form to hit on me, but the Mistress reminds them that I'm ‘off limits’.

 

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