Jacqueline & Diane

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Young woman learns so from her beautiful boss.
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The first time that I met Diane was my first interview with her. I was a little nervous, of course, as I sat in the waiting area. I had already filled out my application and had a meeting with the personnel manager. Diane was the office manager and the job reported to her, so meeting with her was the next step. I remember seeing her walk into the room, look at me and smile. She said my name and I stood up and shook her hand, and then she led me down the hallway to her office.

Even that day I noticed. She was wearing a charcoal gray suit with a white blouse and her long blonde hair was pinned very neatly in a bun. She wore make-up, but it was simple and understated, as were the few pieces of jewelry she had on. Everything about Diane's appearance was professional and business-like, except, she wore sheer black hose and black high-heeled pumps. Being more concerned with myself and how I looked and what I said, I didn't really think about it. I was wearing my "interview" suit - a navy blue jacket and skirt with a white blouse, tan pantyhose, and blue pumps with two or two and a half inch heels. I just tried to sit the right way and answer questions intelligently and do all the things you're supposed to do on a job interview to get hired.

Well, we talked for almost an hour and I felt pretty relaxed with Diane, and when we finished she congratulated me and offered me the position. The job wasn't much but it was my first professional office experience, so I worked hard and tried to learn as much as I could. Diane was a good manager, or at least I thought so. She was very aware of everything going on, and handled things in a very business-like manner. She didn't talk much with any of the girls in the office unless it pertained to work, although she always seemed to be a little nicer to me. She would smile when we made eye contact throughout the day, and when I didn't know something and had to ask for help, she would explain the answers in a gentle and encouraging tone of voice. Diane really made me feel comfortable.

I learned how to conduct myself in a business setting by watching her. She was always polite to people, especially customers on the phone. Her concentration on the work never wavered, and her demeanor and appearance were completely professional. Diane's suits and dresses were always conservative and corporate, very much the ideal for the office environment. But no matter which outfit she came to work in, she always wore high heels. It was a real contrast, seeing her in business suit and a pair of pumps with 3 or 4 inch spike heels, sometimes even higher. She was very attractive, probably in her late 20's or early 30's, with blonde hair, beautiful facial features and a shapely body, and maybe this was her way of expressing some femininity in her professional role. I couldn't quite figure it out and it certainly never came up in any conversation, so I didn't worry about it.

One afternoon around 4:30 Diane asked me if I could stay after 5 because she wanted to meet with me. She spoke very quietly to me when she asked, giving me the impression that wanted no one else to know about it. I told her I would gladly stay, she smiled, thanked me, and went to her office. I got a bit nervous over the next half hour as I tried to imagine what the meeting was to be about. The others in the office left right at 5, and I sat at my desk for a few minutes waiting for Diane to finish a phone call. I heard her hang up the phone and I got up and walked into her office. "Are you ready for me now?" I asked.

"Yes, Jackie. Thanks for waiting. Please close the door," Diane said.

I did and then walked over and sat down in one of the two chairs in front of her desk. Diane was finishing some paperwork so I waited for a minute or so as she made notes and shuffled the documents in front of her. Finally, she looked up at me and smiled as she let out a tired sigh. "I'm sorry to keep you waiting Jackie, but things are so busy right now..." she said.

"Oh that's alright, I understand," I replied.

She smiled again and said, "Yes, I know you do. You certainly have been doing more than your share of the work, and doing a very good job. That's why I wanted to talk with you today."

I thanked her and felt my cheeks getting red. I really valued her opinion and it was so nice to get such a compliment. Diane went on to tell me that she wanted me to be a Special Assistant to her, to handle projects as they came up, to report results to her, and to learn more of the responsibilities of her position.

"You see, Jackie, I think you're very talented and have lots of potential, so I'd like to give you as much extra help as I can. Would you be interested in working with me in this way?"

Well, I was so excited I told her "yes" right away and that I was honored that she thought so much of me to make such an offer. I thanked her several times as I was leaving her office and I could see that she was pleased with my reaction and response. I went back to my desk and as I was gathering up my things to leave, Diane came over to me.

"I was going to the mall to get a bite to eat and maybe do some shopping. Would you like to join me, Jackie?" She caught me by surprise because I had never seen Diane socialize with anyone in the office, but I was still so excited by our meeting that I didn't hesitate more than a moment and said "yes." We reached the parking lot and Diane offered to drive, so we got into her red 300ZX and drove off.

Once at the mall, we stopped and had a light dinner of salad and iced tea, and then strolled around. Diane looked at suits in several different stores and tried on a few. With each one she put on, she asked for my opinion. I told her each time that the suit looked great on her and truthfully, every one of them did. It felt a little odd at first, but Diane was so sincere and relaxed that it was like being out shopping with one of my girlfriends. Here was my boss, this beautiful and successful professional woman, a woman I looked up to and whose opinion I valued, wanting to know what I thought. She finally decided on a light tan wool suit that fit her so perfectly, it didn't need any tailoring so she paid for it and took it with her.

"Thanks for your help, Jackie. It's nice to have someone besides the saleswoman telling me how things look on me," she said to me as we left the store. "Of course, now I'll need new shoes to go with my new suit," Diane continued with a laugh, "You don't mind, do you?"

"Oh no, not at all. In fact, I need some new shoes myself," I replied.

"Great," she said with a soft smile, "I'm glad you came along tonight. It's nice to get to know you better away from all the craziness of the office." Her words were so nice and sincere that I felt a little flutter inside as we walked along there in the mall, aware of her letting me see another side of herself that she had never shown at work. I thought that it was one of those special moments that rarely happens between two people, especially for a boss and one of her employees.

Diane led me into a shoe store where we began browsing. I noticed a selection of dress shoes along one wall and I started to look for a pair of black pumps for work. Diane had gone to another part of the store where I could see her looking over a selection of high heels on display. I had a low-heeled pump in my hands, waiting to ask a salesperson for a pair in size 7, when I wandered over to Diane. She had already asked to be brought a pair of beige leather pumps. The shoe in her hand had a slim heel that must have been 4 inches high. It was exactly the style of shoes she wore to work; just like the dark blue pair she was now wearing.

She turned to me and said, "Have you found anything?" and then noticed the shoe in my hands. "Oh, that's nice Jackie. You know, I've always liked to wear really pretty shoes to work. Some women complain about having to wear heels, but even at the office I like to look nice," she said.

"I guess I thought I should stay conservative at work," I replied awkwardly, not really knowing what to say. "Actually, I don't even own any 'real' high heels."

"Well, you have a nice figure and nice legs; you could certainly wear them if you wanted to," Diane told me with a smile, "And anyway, your work and your demeanor are always very professional. You don't have to worry about conforming to every rule there is; be yourself."

As I listened to her, I was touched by her compliments for my work and by the fact that she had noticed me in a physical way. I had been complimented by other females - friends, relatives, co-workers - but there was something special about it coming from Diane. And there was something about what she said, and how she said it... like she was secretly encouraging me to wear heels like she did. I stood there silently for a minute as Diane turned to sit down and try on the shoes the saleswoman brought out to her.

Then the woman looked over at me and asked, "Would you like to see anything?" Without a thought, I pointed to a black leather, high heeled pump on the table in front of me and said, "Yes. Size seven, please." As she walked behind the counter and disappeared into the back of the store, I returned the low-heeled shoe to the shelf where I found it and took a seat.

I watched Diane strolling slowly around the store in the new shoes and I found myself gazing at her and admiring how gracefully she moved and how feminine she was in those high heels. And I wanted to feel like she looked. I slipped off my work shoes and bent forward to remove the black heels from the box placed in front of me. It took a moment or two for me to wiggle my toes into each shoe and then press my heel down so each foot was nestled into the pumps. I remember looking down and thinking that the heels looked nice on me, and then I stood up to walk in them. I wobbled a little at first, but I stepped slowly and carefully towards a mirror and adjusted to them quickly. First facing the mirror and then turning from side to side, I glanced at the reflection and was very pleased. They were very pretty, and I felt pretty wearing them.

"Those are very nice, Jackie. Do you like them?" Diane said as she walked up beside me.

"Mmm, yes, I do like them," I replied, still staring into the mirror.

Diane remained next to me for a moment longer, and then went to the counter to pay for her purchase. With her gentle encouragement, I decided to buy the high heels and I remember at that moment I was sort of excited about my decision. I guess there was something about Diane's approval, and wanting to be like her, and even being a little "wild" that made it fun.

We left the mall and drove back to the office parking lot so I could get my car. Diane told me she enjoyed the evening, and I thanked her again for her offer, and for inviting me to go out with her. It was quite a day, and I had a hard time falling asleep that night.

The next day, I wore my new shoes to work. It felt a little strange in the morning as I stepped into them and saw myself in my full-length mirror. Dressed in my dark gray business suit, white blouse, and tan pantyhose with these black high heels instead of my usual, conservative pumps I was very self-conscious. But thinking about Diane and what she had said the night before, I relaxed and headed to the office.

I had to concentrate on walking more slowly than usual in the heels but I felt nice in them and I thought my legs looked nicer, too. It was a very busy day at work and I was occupied all day long. Diane smiled when she saw me in the morning and even took a second to come over to my desk and tell me that I looked very nice. I thought it was sweet of her to do that especially because of how hectic it was. We didn't have time to talk about my new responsibilities or anything else that day, but I was aware of how good I felt all day.

Over the next four or five weeks, Diane gave me more special projects to work on and I was able to handle most things. When I needed help, she patiently explained things and encouraged me. We were working together more frequently and maintained our good business relationship in the office. After work, we were often the last ones to leave, and Diane would invite me to go out to dinner once or twice a week. Sometimes we would also go see a movie but usually we would just sit and talk in a restaurant, or go to the mall. It was a chance to unwind, and we got along well.

It was nice to develop this friendship with her because Diane was a few years older than me and I really admired her professionalism and confidence. I was actually flattered that she wanted to socialize with me and form a friendship outside of work. I found myself emulating her and I valued her opinions and approval.

In the weeks following our first shopping trip, I returned to the mall several times to buy new suits and dresses because I wanted to look my best on the job. I also bought quite a few pairs of high heels to wear to work. I found that I really liked the way I looked and how I felt when I wore them. Although I bought most of my new things when I was by myself, Diane always noticed and complimented me when I wore something new to the office. Every time she did, it made me feel special.

One evening at the mall we stopped into Victoria's Secret and started to browse. We moved through the store ending up in the room where the bras and undergarments were displayed. Diane said she needed a few new things and began to pick out lace bras. I had never really shopped in the store before so I was a bit fascinated by all the exotic things they had. I wandered around and came up to Diane who had moved from the bras to a wall rack where she looked through a selection of garter belts.

As she took a hanger out and examined the tag on the pink lace garter, I asked, "Is that for you?"

"Yes," she giggled. "Does that surprise you?"

I began to smile and blush, and I replied, "Well, no ... I guess, I ...," as my voice trailed off.

"Have you ever worn a garterbelt and stockings?" Diane asked. I shook my head and looked away, feeling slightly embarrassed and un-sophisticated. Diane touched my shoulder and said softly, "Don't be embarrassed Jackie. I didn't mean to make you feel uncomfortable."

"Oh, I know you didn't," I said as I turned back to her, "I just never knew anyone who did, or bought them for herself. I always thought that women got lingerie like this just to wear for their men."

Diane laughed and said, "No, not always. I guess the first few times I bought things like this it was for the guy I was with, but I realized how pretty I felt when I wore really nice lingerie and I decided I could wear it for myself. I actually prefer stockings over pantyhose; I always feel bound up in pantyhose! And," she leaned in closer to me and lowered her voice to a whisper, "it's kind of fun to wear something sexy underneath business clothes, and nobody ever knows it!"

Surprised, I looked at her and the wicked little grin on her face and asked, "You wear this to work?" She nodded, and we both giggled like schoolgirls. I started to look at the rack of garterbelts in front of us, tentatively at first, but with Diane's prompting, I selected a complete set of lacy white garments. The bra, garter, and bikini panties all matched, and with a salesgirl's help, I got a pair of tan and a pair of sheer black stockings, also.

Diane showed me how to attach the stockings to the garter snaps, and also told me, "Put the panties on after you put on the stockings; it's much easier when you have to go to the ladies room!"

We left the store laughing and giggling, and when we got to our cars to go home for the evening Diane asked slyly, "So, what will you be wearing tomorrow?"

"Oh no, I don't think I could wear this to the office," I replied.

"Sure you can. Trust me, you can be the perfect professional and still have your own little secrets, Jackie," she told me. "Go home, try everything on, and see how you feel. It's up to you, but, I know I love to look and feel pretty even if it is just for myself."

I smiled and nodded, and then we said good night and drove off in our cars. I was excited as I got home and got undressed because I wanted to see how the lingerie would look on me. I had a little trouble with the garter straps, but after adjusting the length of each and fumbling some as I hooked the snaps to the stockings, I was done. I gazed at my reflection in the mirror for a long time, trying to decide if it looked good on me. I turned one way and then the other, and looked over my shoulder to see myself from the back. The white lingerie was very pretty, and after a while, I smiled because I felt, well, beautiful. Actually, I was somewhat self-conscious even though I was completely alone, but somehow I even felt sexy and kind of "bad", like a little girl who had gotten into her big sister's things without permission.

As I took the lingerie off, I still had doubts about wearing it to work the next day, but I kept thinking of Diane. Deep inside, I think I didn't want to disappoint her. So without admitting it to myself, I had already decided to wear my new lingerie under my work clothes.

The next morning I woke up early and showered quickly. I took the extra time to put on my sexy new underwear which I still was a little awkward with. After finally getting all four of the garter snaps right, I slipped on the tiny panties and took another look in the mirror. I picked out a loose fitting, long sleeved blue dress to wear. It was fairly simple, with a high neckline and a hem that came down to my knees. It had small, gold buttons all the way up the front, and a black patent leather belt around the waist. I guess I wanted to make sure my clothes were as conservative as possible so that no one could possibly know what I was wearing beneath. I stepped into a pair of dark blue high heeled pumps, and stared into the mirror for a few minutes to make sure there were no signs at all of my sexy secret. Satisfied that I outwardly looked as I normally did, I hurried off to work.

I didn't see Diane until late morning when she returned from a management meeting. We were finishing an important internal report and I was very busy. She came to my desk to ask for a document and hurried off, but before she did, she asked me how I was. I smiled and said I was fine. In her most business-like way she smiled and said, "That's good," but then winked at me. It was probably the first time I had ever seen Diane let her personal side show in the office. We worked very hard all day on the report, and long after everyone else had left, Diane and I remained to finish it.

At about 6:30 I walked into her office with the final document. Diane was seated behind her desk, her chair turned to one side, and she seemed to be staring off into space when I approached the desk and placed the report on it. "Here's the final version, Diane," I said. She didn't move or acknowledge me, and looking at her for a moment, I finally asked, "Is everything alright?"

She turned towards me with a start, and said softly, "Yes... yes, everything is fine. You did a great job on this Jackie, thank you very much."

I thanked her, but something didn't seem right and as I stood there wondering, Diane asked me if I had a few minutes. "Sure," I replied.

"Would you mind closing the door before you sit down, Jackie?" she asked.

I closed the door, and returned to sit in one of the chairs in front of her desk. I experienced a strange tingling inside because I had never seen her like this before and I wondered what was going to happen.

Looking at me, Diane said, "You look very nice today. You wore your new outfit today, didn't you?"

"Yes, I did. Could you tell?"

"No, not outwardly, but I thought you would," she answered. I sat back in the chair and crossed my legs as she continued. "You know, Jackie, I'm really proud of the work you do here and how you've grown since you started. You should be proud, too. I'm also very happy with how we have gotten to know each other outside of work. I really treasure our friendship, and I would never want to jepordize it."