My name is Diana Averton and I always considered myself to be a simple and practical kind of girl. At least I did until I met him. But before I talk about him, I should tell you a little about myself first. I am a twenty-year-old blonde who would best be described as elfin, or even pixie-like. I am only five feet tall and weigh in at ninety-eight pounds, and most would think that a good stiff wind would blow me off my feet. But, though I may be slight in stature, I am a tough and wiry girl that was always able to stand my ground. But, once again, that was before I met Him.

After high school I did not have the chance to continue into college, so I took a position with a temp agency and worked a variety of assignments as an office assistant. For over a year I moved from one position to another, usually for a month or two at a time. Then, just a few days after my twentieth birthday my company sent me to work for him. At first I thought nothing of it, as I had worked as a receptionist at other law firms in the last year. But Roland Black was unlike any employer I ever worked for, which I learned the day I first encountered him.

When I arrived at his office, a gated townhouse near the financial district, I sensed something was odd. There was a young Asian girl sitting at the desk near the front door who looked like she was sizing me up as I entered. After I told her who I was she asked me to take a seat and that Mr. Black would be ready for me shortly. I waited and watched the girl at the desk for almost half an hour before being told he was ready to see me. During that time I observed how robotically stoic she appeared, as she worked on her computer and answered a few phone calls.

But, as confident as I felt about being able to handle this new assignment, when I entered his office and saw him sitting there, I suddenly felt weak in the knees. When my eyes met his I almost froze in my tracks, the way his steel blue eyes bored into me had an immediate impact on me that I did not expect. He was an older man, exemplified by his jet-black hair peppered with a fair amount of gray. He gestured for me to take a seat in front of his desk and I was glad he wanted me to sit because I felt like I needed to, but why I was feeling like this perplexed me.

I was still a virgin, but I had a healthy sex drive and often admired handsome men, but never someone as old as him. Mr. Black, however, had a very profound affect on me. Something about the way he was looking at me made me feel weak and insecure, feelings I rarely experienced. But rather than making me want to bolt, I instead felt a strong desire to find out why he made me feel this way, even before he said a word to me. What I had yet to realize was that this meeting was going to change my life completely. I was facing a man who would take me on a journey of self-exploration that would alter my perception of reality and turn me into something I never anticipated. This is where my story really starts and I have been instructed to share it with you now.

Chapter 1: Hired and Attired


“You are Miss Diana Averton I presume?” Mr. Black asked me once I was seated.

“Yes sir,” I answered, my usual loquaciousness abandoning me in that moment.

“I see you have had some experience with law firms in the last year. That is good, as I run a small private practice with very few clients, and they expect anyone working for me to treat them with extreme respect. I say this because they will likely treat you with far less deference or patience, can you handle that?” Mr. Black asked.

“Yes sir, I always treat clients and customers with utmost respect, no matter how they behave,” I answered.

“Good, but let me ask you this, how would you handle a client that chose to make a rude comment about your appearance or attractiveness?”

“I would thank them sir and then make sure that they received the same level of service I would provide someone who was more…polite.”

“In this day and age many women feel the need to work in a politically correct environment, but unfortunately most of my clients are too wealthy and entitled to follow the new norms. Are you sure that this will not bother you?”

“Whether it bothers me or not is irrelevant Mr. Black, since they will be your clients, it will be my obligation to make sure they are satisfied,” I answered. I was young, but I had already dealt with a few men who were too forward and always handled them by graciously declining their advances. I got a strong impression this would be a regular occurrence in this place, but I was never one to raise a ruckus, preferring to disregard those who chose to be vulgar or ignorant.

“I bring this up because I will require you to sign a document stating that you are aware and able to accept that my clientele may say or act in sexually inappropriate ways and you will not file complaints against them. As I said, I have a small practice that serves a select group of people that do not conform to many of society’s values and I need to know that your skin is thick enough to handle some, shall we say, offensive behaviors? Will you be willing to agree to those terms?”

“As long as they don’t physically threaten me I can handle whatever they may say. I would be willing to sign a document to that effect,” I answered, feeling a bit uncomfortable and wondering why this was so important to him.

“No one will touch you, I can assure you of that, but some might suggest things to you that may sound disturbing. Given that you are an attractive young lady will only add to the likelihood that my clients would treat you this way. But in general most of my business is done by phone or email, so the occasional in person meetings will be the exception and not the rule. I don’t want to scare you off, but I also need to be sure you know that some of my clients can be rather risqué.”

“I can handle them sir,” I answered. This was nothing like any interview I ever had before and I was confused, but the sound of his voice combined with his penetrating stare was having an odd side effect on me. I was dressed in a gray skirt and jacket with a white blouse and my simple black two-inch pumps. I was looking very business-like, but as he spoke I began to feel the tickle. That was what I called it when I felt attracted to someone and, though I tried to suppress it, my virginal sex became warm and moist while listening to him. I kept my knees tightly together with my hands in my lap, trying to ignore the physical effect his commanding presence was having on me.

Thankfully he switched to the more mundane description of the duties and tasks that would be my responsibility. I would answer phones, type up letters, manage his files, and several other rather ordinary office tasks. He then informed me that Lee, the girl who was in the reception area, was leaving at the end of the week and that I would need to learn the job before she departed. Since it was Monday, I felt a week learning from her would be sufficient and I told him so. But throughout the interview that feeling refused to go away, becoming worse when he steered the conversation in another unusual direction.

I was a little surprised when he said, “As far as the dress code goes, what you are wearing is acceptable in any normal office, but I expect my assistant to look exceptional. Did you happen to notice how Lee was dressed today?”

In fact I had, remembering how flawless her makeup was while I waited. But now that he asked, I also realized that the bright yellow, skin-tight dress she was wearing was more akin to something a woman would put on to go clubbing rather than what a receptionist would wear. I had dismissed it as none of my business, but now he made me remember how attractive she looked when I had followed her to his office.

Not even considering how inappropriate this was, I said, “She looked impeccably dressed Mr. Black, but I don’t own anything quite as nice as her outfit.”

“Not a problem, I will provide you a stipend for clothing and I will take you to a shop after work today to get you an ample supply of appropriate office attire. That is, of course, if you choose to accept the position. Furthermore, once you have your wardrobe you will have to arrive an hour early everyday to have Lee do your makeup and hair. She will help you find the perfect look and once she has left you will be required to maintain it. Is this all acceptable?”

Again, disregarding how totally improper his terms of employment actually were, I was not only intrigued, but my excitement was escalating too. I meekly said, “Yes sir,” again unable to use my voice as liberally as I normally would.

With a wry smile he said, “Are you sure? I know this is probably unlike any interview you ever had, but as I said, this is a unique type of position that I need to fill.”

“Yes sir, I am pretty sure, but it is a little unusual, please forgive me,” I answered; feeling flustered and a bit worried.

“I know my approach is disconcerting and it is meant to be. And from my point of view you are handling it perfectly, so you may relax now, I just wanted to see how you reacted to the unexpected. You are doing fine and I think you will fit in nicely here, but I must ask again, are you sure you can handle this kind of job?”

His compliments made me feel much better, and coupled with the way just talking to him was affecting me, I replied, “I am very sure that I will like this job Mr. Black.”

When he said, “Good girl,” I felt a rush of satisfaction and attraction that almost made me blush. But he was quick to send me off to Lee to fill out some paperwork and start to learn what she did every day. I hoped it would give me a chance to cool down. Lee was all business and very direct that first day, ‘you do it this way,’ was her preferred phrase as she went through her daily regimen while showing me what she was doing. It did help alleviate the sexual tension I had felt during the interview, but once five o’clock came and Lee left, I was left alone with him again.

To say it felt strange would be an understatement, but once he took me outside and opened the door to the limo that waited for us, I felt exhilarated. Though this was far and away the strangest job requirement I ever encountered, the idea of a free wardrobe provided by this older sexy man made me feel special. I was a little self conscious about this condition at first, but once I spent some time with Lee I realized she was built just like me, she just wore very high heels that made her look taller. Given how good she looked in her form fitting dress, I was now looking forward to wearing one just like it.

We ended up at a small shop that had to be very exclusive, since he used an intercom to announce us and gain entry. A young woman let us in and guided us into it what looked like an old-fashioned sitting room with a very refined looking older woman standing there waiting for us. The girl that answered the door looked just about my age, and like Lee, was stylishly dressed and made up to look both innocent and alluring.

But once we entered the parlor she disappeared and the lady said, “Roland it is so good to see you!” She held her hand out and he bowed and kissed it like a gentleman, it was so…elegant. Then she looked at me and said, “Where are my manners?” Do tell me who this beautiful girl is dear boy!”

“This is Diana, my new temp girl. She needs a new wardrobe of course,” he said.

“Don’t they all? Now if you want me to do this right you will need to leave her with me for an hour, as you well know,” she said. Then she turned to me and said, “Hello Diana, I am Viola and I am going to make you look spectacular once Roland departs.”

“Thank you ma’am,” I replied, feeling like an insignificant mote in the presence of these two people. I had never felt like that before, but I had the distinct feeling that they had plans for me and I had to follow their lead. I was always better at following than leading, but this was different, I was feeling more passive than I usually did.

He then said, “I hope you don’t mind staying here without me Diana, but Viola always works better when there are no men present to distract her. I promise to be back in exactly an hour and will get you some supper before I take you home. Is that alright?”

“Yes sir, I will be fine with Miss Viola,” I said, not sure why the attraction I felt for him was spilling over to this woman, both of them had to be more than twice my age. But here I was, standing silently beside them and feeling like I was playing a game whose rules I did not understand. But the sense of mystery was too spellbinding to resist and I meekly waited for Mister Black to leave.

After the young girl returned to escort him out, Miss Viola led me into another larger room filled with racks of clothes. Against one wall was an area with three mirrors forming a semi-circle around a raised platform. She had me stand on it after telling me to remove my shoes. She looked me up and down for a minute or two, having me turn around a few times in the process.

But then she caught me off guard when she said, “OK, let’s get those clothes off so I can see what will work for your body type.”

I said, “OK,” as I removed my jacket, handing it to her when she reached out to for it. I fumbled with my skirt, as my natural modesty began to emerge, but I managed to shimmy out of it and hand it to her. I unbuttoned my blouse and shrugged it off, but once Viola took it I stopped and just looked at her.

She looked at me and said, “Now the rest,” smiling benignly as she spoke.

“All of it?” I asked, my general shyness making me hesitate in that moment.

“Yes dear, now be a good girl and do as you are told,” she said.

At first I was offended by her remark, but the way she said it and how she was looking at me ignited a strong compulsion to obey her. I found myself sliding my slip and pantyhose off before I even realized it. And once I did, I continued until I finally handed her my bra and panties too. I stood there with one arm covering my small breasts and a hand over my sparse blonde bush, unable to take my eyes off hers. I could feel my cheeks flush and my skin tingle in the cool room, but when she looked at my stained panties I thought I would die of embarrassment.

She held up the soaked gusset for me to see and said, “I see that Mr. Black has had an affect on you, young lady. So you find him attractive despite the age difference?”

I just stared at her, totally mortified by what she just said, and I replied, “No I don’t! I mean, no I’m not…I…I…I have a condition.”

“Yes dear, we all do, now put those arms down at your sides. There’s no need for modesty here, I have seen more tits and pussies than you can imagine.”

I found myself obeying her again, even though I wanted to put my clothes back on and run for the hills. But the way she was looking at me held my urge to escape at bay while I did what she told me to. She gestured for me to turn again and I complied, feeling like I had to do it or she would scold me. She had been nothing but polite, but something told me not to provoke her.

After a couple of rotations she stopped me and with a gleam in her eye, said, “Looks like you are 32B-22-30, five feet tall, and 101 pounds. Would that be right?”

I wanted to say that I only weighed ninety-eight pounds, but she was right about the rest, so I just said, “Yes Miss Viola.”

“Very good, now put these on and I will get something I think will look just right for you,” she said, as she handed me a pair of thin latex panties. My incredulous look prompted her to add, “They will make sure your ‘condition’ won’t tarnish any of the nice clothes I bring out for you to wear.”

That admonition, though humiliating, was fairly given thanks to my weak excuse for being so wet between my legs. She walked over to the racks of clothes while I worked myself into the tight panties, wanting to complain that they were too small. I did not because they were also extremely elastic and I managed to squeeze into them. The result left me feeling like my pussy and buttocks were vacuum packed, but when I saw myself in the mirror it made me shudder. The panties were nearly transparent and my pussy looked like it was on full display behind the thin latex.

“Here, try this on,” I heard Viola say and I turned around.

She was holding a bright blue tank dress that looked way too small. With Viola’s help I was able to slip into it, enjoying the way it clung to me like a second skin. Once the tight hem was pulled down to just above my knees, Viola began to zip up the back and I could feel the stays stitched into the midsection tighten around my abdomen. They helped mold the dress to my frame and pushed the padding under the breast cups upward to elevate my smallish tits. It made them seem so much larger and even created a cleavage, something I always wanted but never thought I had.

“Lovely, you have the body of a model my dear. How do you like it?” Viola asked with her voice sounding soothing.

“I can’t believe how good it looks on me!” I exclaimed. I was truly surprised.

“How does it feel; not too tight I hope?”

“No Miss Viola, it feels just snug enough.”

“You like that feeling, don’t you?”

“Yes, I never knew clothes could feel this good and look so amazing too.”

“Good, now slip these on and walk around the room,” she said, as she placed a pair of matching blue four-inch pumps on the floor next to the platform. I slipped my feet into them, not used to such high heels, but wanting to see how good they would look with the dress. I was not disappointed, they made my skinny legs look so much better and though I felt unsteady, I managed to strut around the room feeling like a fashion model.

She soon directed me back to the platform and had me strip again, and by then, I was comfortable with her and no longer felt modest. She gave me another dress to try on and it fit as well and the first, accentuating my body in ways I never thought possible. Not that I ever had much time or money to look for a sexy way to dress. The notion that these dresses would be what I would wear to work was not even on my mind, I was so wrapped up by how hot they made me look. Once I tried on three similar, but differently styled dresses, Viola handed my clothes back to me and instructed me to dress.

Seeing she had not returned the panties, I asked, “Can I have my panties back?”

“No, I will keep them and you can wear the rubber knickers home. That would be much safer than possibly leaking all over Mr. Black’s limo, don’t you think?”

I was about to object and demand the return of my clothing, but she was looking at me in a way that made me defer to her decision again. Instead, I just began to get dressed without responding. The way she silently smiled at me as I obeyed her told me that she knew I did not have the will to question her. Once I was dressed we returned to the parlor where the young girl was waiting with a black garment bag.

“Mia has packed up tomorrow’s outfit for you; everything you will need is inside the bag. Before the end of work tomorrow she will deliver another outfit for the following day. This will be a daily occurrence and you will bring the previous day’s outfit back for Mia to collect once we get started. You will return it in the same bag in which you received it. Is all that clear Diana?”

“Yes, but it sounds like a lot of work for Mia and you,” I replied, only to get a frown from Miss Viola.

“At any rate,” she replied, “Mr. Black’s limo is waiting for you. He sent me a message that said he had business come up and he sent his driver to take you home. He also said he expects you to be at the office tomorrow at eight a.m. sharp,” then she waved me off and I followed Mia to the door and was sent on my way.

The driver was very courteous and even had a bag of takeout chicken in the back seat to make good on Mr. Black’s promise to feed me. By the time I got back to my small apartment, it was actually a studio; I was in an odd state of mind. Though the chicken smelled good I was feeling a different kind of hunger, so I stripped off my clothes and jumped into the shower. I left the tight latex panties on as I doused myself under the water while worming my fingers into the clinging rubber garment. I soon had a climax so strong that I had to drop to my knees, and oddly, I relived my strange encounter with Miss Viola while I pleasured myself.

It was a strange way to start a new assignment, but after recovering from my shower and feeding my normal hunger, I curled up in bed. I was both nervous and excited about this strange new position, and the even more mysterious Mr. Black. As I slipped off to sleep I was pretty sure this was going to be a weird, yet exciting, adventure, and not the kind of boring job that had been my usual lot in life.