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The Office I was finishing out my internship at Calico Industries. I had been there 2 ? months working as a graphic artist in their main facility. Calico was spread out at six different office complexes, but all were within 20 minutes driving time of the main building. Most interns worked with central staff and since that is where the graphics branch was set up it made sense for me to be there. I had hoped to get on full time, as I had finished my schooling in the spring, but there had been no mention of me getting a permanent job. I was packaging some drawing jobs, done by others in our group, at the front desk, when I saw her walk in our wing. She was scanning the signs as if she were looking for someone. I would normally offer some help to anyone acting that way, but in her case I was eager to offer assistance. Even at first glance, she was strikingly attractive, despite how she was dressed, looking young although she was probably in her mid-30s. Her dark brunette hair was cut very short, but it framed her gorgeous face. The bone structure, full lips, and big brown eyes were set in such a way that even her lack of makeup did nothing to detract from her beauty. Her clothes were unusual for a woman at Calico. She was wearing a dark brown, pin-striped suit, white shirt, flat loafers and a subtle print tie. There was nothing feminine about her outfit, but the tight fit showed her slim feminine curves. She projected beauty and a sense of style that most women couldn't match. Even without heels, she was tall, easily looking down at me at my 5'7" height. I realized I had been staring at her since she entered the building, so I decide to ask if she needed help to keep her from feeling strange. "Good morning, welcome to Calico Corp. Can I help you?" I was smiling broadly, and knew I sounded friendly and non-threatening, at least my co-workers told me that. I had a rather high pitched voice for a man and one of the office girls told me once that she loved the lilting tone when I spoke. I guess if I had a deep baritone voice it would seem out of proportion with my frame. I had a narrow waist that made my hips look bigger but lacked a broad chest. Combined with my short stature, it gave me a delicate quality to my appearance. That was reinforced by my cherubic looking face; I just never got rid of my baby fat in my cheeks. Despite being 22 years old, most people assumed I was a teenager. I also had a penchant to dress oddly. I liked to think that my sense of style was unique and an expression of my individuality. The dress code at Calico was business formal that prosed a bit of a problem for me, since I owned no suits and only two sport coats. During the week I struggled to meet their requirements. But today was casual Friday, and I took advantage of it. Going through college I wore shorts almost exclusively, so on Fridays I brought that look to work. Today, I wore khaki shorts, a white dress shirt, a beige flowered vest, and loafers with no socks. Ever since I had been at work, I limited my jewelry, of which I normally wore a lot and kept my double pierced ears to simple studs. I had my long blonde hair pulled back in a ponytail, which with the scraggly beard I had been growing all summer, made me look a bit like an artist. I had hoped the beard would make me look more mature, but it never really filled in and it was so light in color that it lacked presence. The lady visitor just looked me over, smiled as if mildly amused and then came closer for a question. "Good morning, I'm Alice Mann from the Kings Pike branch and I'm looking for Roger Gardner. He supposedly runs the Graphics Department. I need to review a few projects." "Oh yes, Mr. Gardner's office is down this way. I'll be glad to ring him for you, if you'd like or I can just take you there." "Please let him know I'm here. I really don't like to just show up at someone's office. Are you his secretary?" I smiled at that, for a couple of reasons. First no one at the Central Office of Calico used that term. Administrative Assistant was the title for office help, usually shortened to Admin. Second, I had never seen a man in that role, not that it wasn't suitable, but usually the office managers hired cute young girls. I assumed it was a stroke to their ego and gave a more standard look to visitors. But I let this go, and made the call to my boss. The usual Admin had gone to the bathroom and since I knew how the office intercom phone system worked, I just did it for her. Once I had informed him that Ms. Mann was at the front desk, I told her that I was only an intern in graphics but glad I could be of help. Her smile made me feel appreciated, and as she started to walk toward Mr. Gardner, she turned to me. "I should have guessed that you weren't a secretary. No manager would allow such a scruffy little beard for someone in the eye of public, or for that manner, those hairy legs. Otherwise, you'd be cute enough and apparently efficient as well. Thanks for your assistance, Mister...?" "Lynn Clark, mam, nice to meet you." She went on to her appointment and I spent the rest of the day helping others prepare their work. That was one part of being an intern that had been disappointing. I had not done any projects on my own. Mr. Gardner preferred that I handle the distribution part of the jobs, so the artists could focus more time on their work, which generally meant repackaging standard company images to supplement proposals or product contracts. Not very imaginative at all, but they seemed happy enough. I got the impression that the pay and benefits were good for this area. I had two weeks left, but by now I understood that Mr. Gardner had no long-term need for my services. After my usual weekend, I had made it till Tuesday afternoon, when he called me into his office. This was unusual, as he normally just dropped by the little cubicle I had to give me work instructions. Mr. Gardner was friendly enough, but I think he was more concerned with pleasing higher management than cultivating his worker's appreciation. He started out with the same canned chatter about work, etc., but soon switched to the fact that I only had a week left and that despite how good my work had been that they did not have any openings for employment. However, there was a short-term need for graphics assistance at one of the branch offices and I could finish my term there if I wanted. Since I had nothing to lose, I agreed and he gave me directions to the building. I noticed right away that it was the Kings Pike location and I was to report to Ms. Mann. That information peaked my interest immediately. That night I reflected on our brief meeting and her parting comments. So the next morning, I put together my best company outfit and shaved off my failed attempt at a beard. I wanted to start off right with her. The location was a small single story building and from the parking lot, I could see that there were only a couple of dozen employees. As I entered, I could tell the layout of the building was different than the main location; Kings Branch had a small lobby with a front desk rather than a foyer with multiple hallways leading to different departments. I guess it was more like the wing where I worked. There was no one at the front, so I looked around till I saw Ms. Mann's office. I knocked lightly, as I could see her at her desk and softly spoke. "Good morning, Ms. Mann. I was told to report here today, I'm Lynn Clark." She swiveled in her chair to face me. Glancing up and down, she checked me out before smiling and motioning to a chair for me to sit down. "Oh yes, I remember you Lynn, I asked Mr. Gardner if I could have you for a few days. I hope you didn't have any problem finding this location; we're a bit smaller than the Central Office. I needed someone to work up some images for several proposals and wanted original drawings. The standard office images are so drab and I wanted something with a bit more flair. Based on your appearance when I saw you last week, I took a chance that you might be a bit more creative than the usual staff. Do you think you can deliver?" "Oh yes, I love to draw. If you can give me some description of your ideas, I'll be glad to work up a couple of draft options for you to choose among and then give you a full color image if needed. I can work either with digital or hand drawn formats." She responded immediately to this offer, and we began a quick back and forth covering her image needs and her conception of what that should look like. I was ecstatic as this was the kind of work I had desired all summer. After we went over the requests she took me back to a small studio that had everything I needed. On the way she introduced me to others on her staff. It was apparent that they all respected her and I could see genuine interaction when they spoke. I was already feeling a thousand times better about how I would finish my internship at Calico. As she left the office, she turned to tell me something else. "Lynn, I am glad that you shaved. That beard did nothing for your look. Also we observe Casual Friday at this branch too, but I expect you to maintain a professional level of appearance even if a bit more relaxed. I want my staff to enjoy work, but I have standards they must meet. You okay with that?" "Oh yes, most definitely Ms. Mann. I just appreciate the opportunity you are giving me." As she left, she smiled. I was in seventh heaven. The work flew along until nearly quitting time. I took her six rough sketches and she was very impressed, telling me to continue work on four of them. She outlined how she wanted changes made and solicited comments from me about certain aspects of each drawing. Thursday I got to work early and drew my designs all day, checking with her once to be sure that I was still on track. She was friendly, but smirked a bit when she first saw me. I guess my attempt at a corporate image was pretty weak. If I had been here all summer, I would have spent some of my salary on a suit or at least better trousers. I made my mind up at that point, that tomorrow I would wear one of my most creative short outfits. Most of the time in college I wore just regular khaki or jean shorts, but for special occasions I had better combinations, with more color or higher quality items. I was going to go with what I thought was my best look. I woke early Friday and took my shower. Mindful of her comments, I took the plunge and shaved my legs. I felt awkward doing it, I mean I know it was not typical for a man to have shaven legs, but knowing her opinion, I felt it had to be done if I was in shorts. At first, I was only going to shave up to my knee, but I decided I might as well go all out and continued up my thighs. Putting on some lotion, I felt a little odd but I knew it was necessary. My outfit was centered on a pair of Madras print Bermuda shorts. They were mostly green and beige plaid over a white background, but with a narrow pink stripe woven in. I matched the shorts with a faint pink oxford long-sleeve shirt and a vest that matched the shorts. A pair of my nicest brown loafers completed the look. I know some might think the overall look was a bit feminine or gay, mainly because of how coordinated it was, but I liked it. I think it was so fashionable that it seemed unlike me, so it fit my aim of being a bit unconventional. Like the previous days, I got to the office early and had just finished the final designs when Ms. Mann arrived. I couldn't wait to show her, so I almost followed her into her office. I noticed right away, that she was dressed casual too, wearing tight blue jeans, and a white dress shirt. On anyone else, it might look plain, but she made it look pretty hot. As she got to her desk, I stood in her doorway. She looked at me and I held up two of my best drawings. I saw her smile as she glanced my way. "That looks much better. I like your flair and appreciate you taking my suggestion." I had been looking at my drawings as she spoke, and as she finished, I looked back at her. To my surprise, she wasn't focused on the designs, but was looking down at my shorts and legs. I realized what she meant by the comments and blushed. Seeing my reaction, Ms. Mann laughed and asked for the designs. As I handed them to her, she mentioned that she normally had a cup of coffee first thing. I took the hint and went to the coffee maker in the lobby and poured her a cup. "The designs are just what I had in mind, Lynn. Good job. Now I need to blend them with the text. Normally my secretary Tracy would handle that, but she is out today. Do you mind working it up for me? I sent the files to her computer share area. You can access them with the computer at the front desk and the layout formats are also in that area. Just place your drawings in the space saved for them and format for printing. It shouldn't be too hard, and I can answer any questions you have. Also, since you'll be at the front, just answer the phones and welcome any visitors." I was so thrilled by her approvals of my work that I gladly agreed to help. It took me a little while to find the files, insert my drawings, and format for printing, but I figured it out pretty well. The phones were just like the system at Central, so those were no problem either. I spent the rest of the morning finishing her request and then printed out one copy of each proposal for her to review. There were only a few corrections and then she showed me how to send them to our production printer for high quality copies. Once I had them sent on the way, I sat back in my chair. This had been the best few days of my time at Calico, and I was feeling pretty good. Just as I was about to head back to the vending area to grab something to snack on, Ms. Mann came out to the front desk. "Lynn, you did a great job on those designs and proposals. How about we go out for lunch to celebrate? I'll treat. There is a nice little soup and salad place right down the block, so we can walk there." Of course I agreed, not only to get something good to eat, but spend more time with her. Ms. Mann was the kind of boss I would love working for. At the diner, we chatted about a range of stuff, like my college experience, what I thought of the internship, and Calico Corp. I tried to be polite, but honest. Several times, she had me laughing. I liked her personality as well as her sense of humor. We were finished and about to leave, when she asked me another question. "Lynn, I can't help but notice that your casual outfit is much more put together than anything you wear during the week. Most days, you look like you just grabbed something from your closet in the dark. But the way your shorts, shirt and vest match and the fact that you feel comfortable wearing such a coordinated outfit makes me wonder. What's up?" "I guess I always preferred shorts. I mean I wore them daily at college. Mostly they were every day styles, but I did take the time to create some complete outfits, like this one today. My other clothes are like you describe a hodgepodge of fabrics, colors, and styles. I really never feel put together or even comfortable in them like I do shorts. But if I had a real job, I could focus enough to create a professional look for every day." "Well shorts if done properly, can be a professional look too for some positions. You just need to properly accessorize the outfit. You already have a great start with the matching vest and color coordinated shirt. One thing you would definitely need to change is your boxers. I can see the top of them through the shirt and they have too much fabric for such tight shorts. Let me show you a better alternative." I just nodded and we left the diner heading down another street. After a short walk we can to an area of small specialty shops, including one that had displays of women's lingerie in the front window. I was a bit embarrassed, but followed Ms. Mann into the store. She walked around a bit, but soon found a display with a mannequin wearing a pair of lace hipster panties and a lace trimmed camisole. Spread out around the mannequin was a selection of different colors of the two items. She picked up a pink pair of the panties. "A style like this is tighter and fits close to your body. It would be much better under your shorts. Also, colors that match your outer wear are always a nice choice for lingerie. An undershirt like this camisole completes the look. These are nice because of the touch of lace, which would allow you to have them show a bit if needed. I'm not sure of your size, so I'll have a saleslady measure you quickly. Just follow me to the back." I was stunned and more than a bit embarrassed, but because the past few days had been so nice at work, I followed her. She spoke to a saleslady at a counter, who recognized her, and they took my measurements. Knowing my sizes, Ms. Mann went back to the table and picked a pink set of camisole and panty. She handed them to me. "Lynn, slip these on for me. I want you to see how better fitting underwear will help you look more professional. I'll pick out some more colors, basic ones, which should go with any outfit. Because I like you, I'll cover these costs. Now hurry along." I guess I felt trapped; I didn't want to disagree with her but was uncomfortable with putting on woman's underwear. But I did what came naturally to me; I went along in order to avoid conflict. The panties felt a bit odd once I had them on. They did not go up to my waist like the boxers but the silky fabric felt real nice. The camisole was the same. I had worn undershirts before, but this was tighter and the spaghetti straps were very different than any male undershirt, not to mention the lace trim around the top and bottom hem. I put on the rest of clothes and came out so Ms. Mann could see, gingerly holding my old boxers in my hand. "That is much better. You have a smoother silhouette without the bunching from your boxers. Do they fit okay? Not too tight? I always felt that proper underwear was essential for a stylish outfit. Sort of like the foundation of a house, even if you don't always use a shaper to achieve it. This style of panty and camisole has just enough spandex that it will make any outfit hang better on you. Just be sure to take good care of them. As for those boxers, you won't need them anymore. Just throw them in the trash can over there." With that she turned and headed for the counter. I reluctantly threw out my old underwear and met her at the counter. The saleslady had rung up camisole and panty sets in nude, white, black, baby blue, and peach. She said that if I wanted any more colors in this style, that I could get a discount on additional purchases. I already felt like I had too many for my taste, but thanked her anyway. I also thanked Ms. Mann, as I didn't want her to think I was ungrateful. We headed out the door and back in the general direction of the office. Ms. Mann was talking about how to accessorize an outfit to make it look professional, quizzing me about jewelry, shoes, etc. We were passing a shoe store when she suddenly stopped and pointed to the window. It took me a minute to figure out what she was pointing out, when I saw them. It was a pair of high heel, rounded toe pumps. The base color was light beige, but they had a pink and green plaid overlay. I could see immediately that the color scheme matched my shorts and vest. "That is exactly what I was talking about. A nice shoe that coordinates or accents your outfit can totally finish a look. That shoe is a perfect match for your outfit. I can't believe it, usually with a plaid or other combination of colors you would just pick one of the primary colors to match. But these are so perfect we have to check them out. Let's see what sizes they have." She didn't wait for an answer, but grabbed my hand and pulled me into the shop. Once again I was overwhelmed by the suddenness and forceful action of Ms. Mann. She asked the saleslady for some help and she gladly assisted us, even calling her by name. Ms. Mann had correctly assumed I did not know my size for women's shoes and had the lady measure my foot. It turns out that I wore a woman's 7 and half, a small size even for a woman, but especially for a man. They did have the shoe in that size, and soon I was trying to stand in the 3 inch heels. Ms. Mann held my hand as I took a few steps. She told me to walk on the balls of my feet and just use the heel for balance until I was more comfortable with them. I felt awkward, not only because of the heel height, but more because they were women's shoes. I could feel my face glowing, but neither woman acted as if it was at all unusual for a man to be trying heels like these. Ms. Mann continued to talk about how they set off my outfit; it was obvious that she felt like most women, that a good shoe was critical to your appearance. I was starting to get the hang of walking in the heels, so she let go and sent me down the aisle telling me to walk back and forth a bit to get more comfortable. Comfortable would not be a word I used with these, even as I became adjusted to them I could feel my calves tighten and toes pinch in reaction to the shoe design. Ms. Mann went to a display of hosiery and after quickly looking over the items, selected a pair of sheer to the waist, nearly nude color pantyhose. "Lynn, although the bare leg is common today especially for younger women, to appear professional in something like you have on now, you must use hosiery. The finish that a nice pair of pantyhose gives your legs makes them an essential part of a wardrobe. Either a colorful pair of tights or something sheer like these would be appropriate. Since you have so much color in your shorts and shoes, I think sheers would be best. Go into the change room, and put on these for me. I want you to see how they help your overall appearance. Do you know how to put on hose? It's easy; just be careful with the fabric, gather up the leg until you are at the toe and gently slip them up your leg. The attached panty should come up to your waist and fit snugly over your new pink panties. Go on." I was totally bewildered. I mean wearing women's lingerie was strange, but at least they were hidden. The shoes and now the pantyhose were totally visible; it would be obvious to everyone that I was wearing women's items. I wanted to say no. I wanted to tell her thank you for her help. I wanted to tell her that I didn't think this was the look I should have. But I knew it was important to her and I liked the job and working with her. So, I rationalized that it was only for a day and she was paying for it all. I agreed and took the hose. Although I had never tried them on before, I had seen how women did it. Following Ms. Mann's instructions and what I remembered from seeing my older sisters, I was able to get them up my legs without a problem. What surprised me was how nice they felt on my smooth legs. The silky fabric seemed to caress my legs and even the tight feel of the panty seemed sexy. Once I had the shorts and shoes on I came out for her to see. "Now see what I mean? You look much more professional. If you had some nice jewelry and maybe a bag, it would be perfect. Think about accessorizing this outfit and you could wear it any day of the week at work. In fact, do you have a coordinated shorts outfit in black?" I told her I did, but almost immediately regretted it. It wasn't one I wore often, mainly because I had purchased it at a repeat store and after I got it wondered whether it was actually a woman's outfit. I used it just when I felt like being really different. The outfit was a matching blazer and pair of shorts, in a small black and white check pattern. The shorts did not have a long inseam coming just to mid-thigh and the blazer was designed so that it narrowed at the waist before flaring out at the bottom. I only wore it with a black turtleneck, fingerless gloves, and some military boots. It was sort of my winter shorts statement for parties or wacky college drinking events. When I confirmed that I had a black outfit, she went to a display and picked up a pair of black heels. They were even higher than what I had on, with a sling back design and a small bow on the toe. Holding up the shoe, she turned to the saleslady. "Do you have this in his size?" The affirmative answer made her smile and she asked the lady to add it to our purchases. She also picked up a matching purse, which had the same color black leather with matching bows on the shoulder strap. Putting it on the counter, she went back to the hosiery rack and selected a sheer black pair of pantyhose in the same style I was wearing. "Lynn, combine these with your black shorts and appropriate color- coordinated underwear. Accessorize them with some jewelry and wear your hair in a style other than a ponytail. I want you to come in Monday with that outfit. I have the feeling you will look professional. If you are able to pull it off, then you can wear shorts every day of the week as far as I'm concerned. I know your internship ends next week, but I have a feeling my regular secretary won't be back for a while. She's pregnant and went to the doctor today because she's been having some issues. I fully expect him to tell her she needs bed rest and to be off her feet over her last two months to be sure the pregnancy is stable. Given that Calico has a 3 month maternity leave for post-birth, Tracy could be gone as long as 5 months. If you're interested I think you can handle her job. I also have a lot of small graphics jobs that you could do as well. You'd be getting about 3 times your current pay, with medical benefits and accumulated vacation. I'd be filling a job need and getting the unique graphics support I have been seeking. So what do you say? If you're game, I'll put these items on the bill and pay for them." I felt like I had been punched in the gut but kissed on the lips at the same time. I was really uncomfortable with what I was wearing and imaging how I would look if I combined my blazer and shorts with her accessories. But I really needed a job, and liked working for Ms. Mann. Again rather than rock the boat, I just smiled and told her I'd try it. Her smile made me feel better and she finalized the bill with the saleslady. Thankfully, she suggested I just wear my loafers back to the office as I wasn't quite comfortable yet in heels. I still felt odd walking back with her wearing hose under my shorts but I was really thinking more about the added money I would be getting. Back at Calico, she had me put the pumps back on and work the front desk. She did confirm that Tracy called with the news she expected, so I was set for Monday. The rest of the day was a little unusual and I tried to stay at my desk as much as possible. A couple of the girls in the contracts office noticed my heels and loved them. I had to chat with them a bit about the design, shoes in general, and tell them the story about Ms. Mann's offer. They were thrilled, which surprised me. By the end of the day, I had adjusted to it a bit, convincing myself that it would be worth it for a good job. Once I had more money, I would buy some suits and step away from my shorts to a real professional look. I spent most of my weekend trying to adjust to my new look. I wore heels around my apartment and began to get where I didn't feel like I was going to face plant every time I crossed a room. But I also couldn't see why women loved shoes and heels so much. If I stood for any length of time, my feet and calves began to hurt. They did make your legs look good, but was it worth it? I tried on my outfit for Monday and decided that if I buttoned the two buttons on the jacket, then I could go without a shirt and not show off my camisole. The jacket was a heavy fabric, so it would be warm enough by itself; a shirt would make it worse. I also decided that I had to shave my chest if I wore just the jacket. Once I had that done, it looked odd to be hairy in just some areas of my torso, so I also shaved my belly, trimmed around my pubic area, and removed my underarm hair. I hated to admit it, but I really looked better without body hair. I mean, mine was not real thick, being patchy with lots of naturally lightly hairy areas. So being smooth all over made the bare places look better and didn't really emphasize them. By the end of the weekend, I had chosen all my accessories and felt comfortable enough for my debut on Monday. I woke up early, showered and washed my hair. Normally I washed it at night and put it in a ponytail. If I was to leave it free, then I needed to blow dry so it would be straight and full. It didn't take long to dress, even with putting on pantyhose , the black camisole, and panty. I had decided to use some silver jewelry I had that had black highlights. For my ears, I used two sets of hoops, one small and a larger pair. They were twisted in design with a black inlay. I had a black and silver bead bracelet, a silver necklace with a black center bead, and three rings. In college I always wore rings and tried to find a little bit of jewelry to match. By the time I dried my hair and put on the jacket, I had to admit I looked pretty professional, although not at all manly. The heels, hose and purse gave me a decidedly feminine look and I knew when I buttoned the jacket that it was a woman's because the way the narrow waist emphasized my hips. I had planned on getting to the office early and beat just about everyone in. I started the coffee for Ms. Mann and started checking my email. When she walked in, she gave me a quick smile as she passed to her office. I poured her a cup of coffee and followed her. Since this was my first official day as her secretary, I wanted to find out what all she expected of me. I knocked as I entered her office. "Thank you Lynn. Let me get a good look at you. Very nice, that outfit is even better than I expected. You have a great touch for coordinating a look. I imagine it is the same gift you have for creating your graphic art. I think we can go forward with you in similar outfits during the week. I have certain requirements for my secretaries. Since you will be at the front desk, I want you to look professional at all times, so if you need to upgrade your old outfits with better accessories or shoes, let me know. I'm willing to advance you some money to cover your needs till you get your check. As far as your duties, I expect you to handle all my correspondence, answer phones, greet visitors, work up the proposals for printing, coordinate my calendar for meetings and appointments, and generally support me as needed. You will also be the support person for the others in my office, although generally their work will require less of your time. For this morning, I need you to set up the conference room for our Monday group meeting. That means providing coffee and snacks. The little doughnut shop across the street prepares a small tray for us every week. Just go over in about an hour, pick it up and sign for it. You will be required to take notes at the meeting. There is a tablet for such work in your desk. But above all I want you to be pleasant, friendly, and outgoing. I think a good secretary is seen as a friend to everyone on staff, so take time to say hello and visit during the day. Tracy was very good at that. Things, like talking with the female staff about fashion or their social life and flirting with the male staff to boost their egos. Those kinds of details help everyone feel good about their jobs and make them more productive." With that she stood up, and unbuttoned my top jacket button and spread the lapels a bit. That opened up my jacket, showing the lace top of my camisole. Smiling she reached in her purse and handed me a tube of pink lip gloss. "Lynn just because you need to look professional, doesn't mean to hide your personality. It is okay to be a little flirty, even mildly sexy with your appearance. A touch of lace or shiny lips makes you more appealing to the guys and one of the girls. A secretary should truly be an office girl, as much as a professional administrator." This caught me off guard. She was further highlighting a feminine appearance for me. It was as if I had desired to be seen as a woman and she wanted me to know it was okay. I didn't know what to say or do to stop this without challenging her. I thought if I clarified the work aspect from her social descriptions, maybe I could stem the trend she was establishing for me. "Ms. Mann, I understand what you are saying. I expect it worked well for Tracy. Everyone seemed to like her and she had an outgoing personality. But I'm not her and I'm a man, so it is not really easy for me to act like she did. I already feel different because my clothes are more feminine than I have ever worn. Also, your job description is quite different than those for the Admin Support staff at the Central Office. Yours has much more of a social component. I mean you even refer to me as a secretary, which is a decidedly old-school term. I don't want to complain, but I do want to point out what I see as differences in how you and I see this job." Her smile now turned into a chuckle and she again ran her fingers down the edge of my lapels, stopping to fiddle with the lace trim on my camisole. She looked up from the camisole to my face. "Lynn, let me answer your last complaint first. I do use secretary for a purpose. An admin support term is purposely vague and gender neutral. Secretary usually implies a woman, or at least a feminine person, and someone who is sexually attractive. It also implies a bit more of a submissive role, someone whose function is to cater to her boss and that is definitely what I want. You will do everything the way I want it, including your behavior and appearance on the job. I prefer to have someone who knows they are expected to bring me coffee, pick up lunch, or fetch anything any time I need it. Although it implies a second class status at work, I compensate you by paying you more than the support admin staff at Central. As for you appearance, I'm just highlighting what seems to have been a natural inclination of yours. I have never met a man who wore coordinated outfits like you do, especially one that was centered on shorts. Not only did you wear one, but you had multiple such outfits, including this one that is certainly a woman's design. Also you seem eager to please me; I mean I make an offhand comment about your hairy face and legs, and next time I see you they are smooth. Your acceptance of my requirements for your underwear, shoes, accessories, even hosiery, for a professional look is final proof of both your feminine gender and your submissive nature. I don't mean to hurt your pride, but your appearance when your feminine features are highlighted is much more attractive than your masculine appearance. It is okay to realize that and take advantage of it. Once you start feeling more comfortable in your new role, you will find it easy to talk fashion and beauty tips with the other girls, or bat your new longer eyelashes at the men who you greet so enthusiastically at the front desk. Your voice is already feminine, but with a little more practice you can make it sultry as well. So don't feel offended by my requirements or title for you. I realized a long time ago, that I had a more masculine personality than a woman normally does, so I took advantage of it. I purposely wear my hair short, avoid makeup, and wear men's styles in clothes. I talk forcefully and make demands rather than requests. I am also brutally frank if needed. This approach, a more masculine one, has helped me become a better manager and the youngest to ever head up a branch office at Calico, not just because I do things as a man would do, but also because they are natural for my personality. So think about it and I'm sure you will find that it will be to your advantage to adopt a more feminine approach, as it seems to be your true nature. What you must remember is that just because you have a feminine gender doesn't necessarily mean you are gay. I project a very authoritarian and male-like image, but I have no lesbian interests at all. Don't let your gender inclinations be any more than a way to be successful, unless that also matches your sexual orientation. Is that clear? " I knew my face was blushing as I could feel the heat. Ms. Mann had skewered me with this response and it was effective, because it was based on truth. I hadn't admitted it to myself when I saw my image this morning, but the feminine Lynn was much more attractive than the masculine one could ever hope to be. Instinctively, I must have known this before, as the outfits that I was most proud of and felt good when I wore them, were obviously feminine. I also had a strong submissive streak and could easily be swayed to behaving how someone else demanded I behave. That easily explained how I would let a woman I had met only a few days ago, convince me that I needed woman's lingerie, pantyhose, and high-heel pumps to achieve a professional look. I really didn't have much choice and when I compared what she was asking me to do, to the prospects of having no job then the choice was easy. Once I came to this realization, the rest of the day flew by. I easily fit in the role of her secretary and by the end of the work day I think most of the staff saw me in that role. The ladies at work made a point of praising my outfit, and noticed my lip gloss. One, Mandy, even outright suggested, that I should use some mascara and eye shadow, as it would emphasize my lovely eyes and after work we went to a nearby drugstore to pick out a few items. By the time we left, I had everything I needed, including foundation, blush, a couple of lipsticks, and all the brushes and implements I could use. Mandy followed me home and we spent the evening trying out everything over a takeout Chinese dinner. I felt pretty awkward during the whole thing but when she left, Mandy leaned in and kissed my cheek telling me that she thought it was really cool that I was willing to highlight my femininity. Most men didn't have that kind of courage, and that it was definitely fitting for me. The next morning, Ms. Mann beamed at me when she saw my face. She complimented me on my improved appearance and acceptance of my new identity. The rest of the week went by as if I had blinked, but I was rapidly running out of outfits. I had become vain enough that I didn't want to start wearing the same things every week. When I whined about this at lunch with Mandy, she and her co-worker Meredith practically squealed with delight. They insisted that we go shopping that weekend. They knew some nice discount places where I could find something cute and current without a lot of money. I got up early Saturday morning and was ready when they came by. The first store catered to young women with a range of cute clothes bordering on professional yet flirty. Looking around I couldn't really find any shorts, especially ones that could be used to build an outfit around, and suggested maybe we needed to try a different store. They looked at each other and then back at me grinning, with Mandy finally speaking up. "Lynn, its time you break away from your hang up with shorts. I know you like them, and they are a cute but occasional look, but there is no reason to have that as your only option. With your great looking legs, you can be just as stylish if not more so, with a nice dress or skirt outfit. There are hundreds more combinations you can work with if you open up your range of clothes. I mean you are already wearing makeup, hose, and heels, does it matter if you use a skirt rather than shorts?" I couldn't deny their logic and although it felt odd at first, I soon found myself excited with the choices to be made. We wound up with several skirt, top, jacket combinations that could be used interchangeable to give me a whole new wardrobe. Although I was content with skirts, both ladies kept having me try on dresses as well, and I had to admit I liked the look of what they suggested. My only problem was that most of the dresses were cut to allow a woman's bust. A bust I didn't have. I pointed out to them, that my failing up top kept me from looking good in one flowery shift in lemon yellow that we all loved, and then both women agreed. But surprisingly rather than give up on the dress, Mandy suggested I just add a bra and some padding. Meredith whole heartedly agreed. They pointed out it was just another piece of lingerie and that it wasn't much different than the camisoles I wore almost every day. Soon I was wearing a nice lace bra and with a few socks used for temporary padding, the dress fit wonderfully. I was a bit concerned about the size they suggested for my bra, a 36 C, thinking I wanted something smaller. Both disagreed, they said I need that size to compliment my narrow waist and fuller hips. A larger bust gave me just the right proportion. Mandy admitting that her size up top was not all her, said she knew a lingerie store where I could buy some silicon pads that would fill out the cups. She also suggested that I look at some of the medium control shapers, like Spanx or Flexees, while I was there. Unlike shorts, skirts and dresses couldn't control any surprise male bulges that might appear. She laughed that tenting a skirt was not a good look! So by the end of the day, I had four new skirt outfits, in complimentary colors, three dresses, four bras, three long-leg shapers, and a set of silicon falsies. I had to max out my credit cards to buy all this, but both women insisted I was doing the right thing. Hopefully Ms. Mann would agree. I desperately need an advance on my salary if I wanted to eat this week and somewhat vainly couldn't wait to go back to the shoe store to find matching pumps and sandals for my new outfits. Although we had spent all day shopping, both women were so excited that they wanted to treat me to a manicure and pedicure at their local nail salon on Sunday. I wanted to act uninterested, but couldn't as the idea really appealed to me. The next afternoon, looking at the color choices, we decided a soft coral would complement both my skin tone and most of my new outfits. When they were done I loved my new look, but again whined about my lack of shoes. Both ladies laughed, saying this is too typical. So we made one last shopping trip to a shoe salon, where I found a darling sandal in yellow patent with a matching purse. They were perfect for my new floral dress. I had just enough room left on my card to get them. Meredith said all that was left was for me to get a new hairstyle, so we went back to her place where she used hot rollers to try to give my current cut a new look. Playing around with several sets, we finally chose one that gave me a nice wavy curl to my hair. I couldn't believe how great my hair looked with this subtle adjustment. Meredith gave me a nice little diagram and some of her old sponge rollers to use that night. If I just set my wet hair before bed, when I woke I could comb them out to get the same look she achieved with the hot rollers. All this seemed so exciting and yet I was a bit fearful of what Ms. Mann might think of my new look. I mean I was a man after all, but with these changes I was going to look fully female not just a fashion forward male. I hardly slept that night, so I got up early to get ready. I had taken a bath the previous night and shaved everything smooth again. For my debut, I had chosen the yellow floral dress with my matching accessories. I slipped on my peach blush lace bra with the matching camisole and bikini. Pulled on some sheer black hose, my new Spanx shaper and then sat down to do my makeup. I took my time, doing everything carefully. When I finished, I felt my face had never looked better. My new dress felt great. The feeling of tightness as I pulled up the rear zipper was wonderful. Removing my hair curlers, I teased out my curls into soft waves that framed my face, using some hair spray to set the look. My new shoes, purse, and some silver jewelry finished the look. I had never felt better about how I looked, but the test would be Ms. Mann's reaction. As usual, I made it into the office before she did. I had coffee ready, checked the weekend emails, and verified her schedule for the day. I had just opened her office and started her computer for her when she arrived. Ms. Mann saw me from behind, standing just inside her office, and as she approached she greeted me and I turned to welcome her. "Lynn, are you wearing a dress? Do you think a man wearing a dress to the office is appropriate or professional? From the look of it, you've got on a bra, a very padded one. I also see you've styled your hair, got your nails polished, and if I'm not mistaken from the smooth lines of your skirt, you're wearing a girdle as well. I guess you weren't satisfied with just panties, hose, and some light makeup. I guess I really didn't evaluate you properly. So how do you explain your appearance?" I was stunned at her reaction to my new look. I thought she would be thrilled, but she sounded as if I had committed a crime. She seemed so supportive, even initiated my earlier forays to appearing feminine, that this new attitude was bewildering. I began to blush, furiously, and my brain spun trying to think of what to say. Finally, not knowing how else to answer I blurted out the truth. "I, I, I.. I was trying to look more like a secretary. I thought you were encouraging me to find the look that felt natural to me. Mandy, Meredith, and I went out to get some new outfits this weekend, but trying to stay in outfits based on shorts was impossible. The shift to skirts and dresses seemed like a small one. From there, I just went with the flow trying to make everything match and seem appropriate. I guess I didn't really understand your directives, but I was just doing my best. I'm sorry if I went too far." "So appearing as a woman, in a dress and padded bust is what feels natural to you now, and represents what you think of as secretary apparel?" "I'm sorry, but I guess I do. I mean my friends said I looked nice and thought I appeared passable. Obviously, I was wrong in my thinking." Suddenly Ms. Mann's face went from serious to smiling. She reached out with her left hand to stroke my right arm. "Well I think you look very professional and very appropriate for my new secretary. In fact you look stunning, and I might add quite sexy. That dress not only shows off your dynamite legs and narrow waist but with your new foundations highlights your female curves. Surely you thought your face and hair looked better today than you've ever looked before didn't you? Well I do. You are going to be a great first impression for my division of Calico. But you have to be sure about it. Don't waver in how you see yourself. I don't want doubt to creep in about your new look and identity. Being sexy and feminine is as much about confidence and attitude as it is about curvy butts and big breasts. So don't let anyone raise questions in your mind about how you look now, understand? Just one thing you need to do: place an order for your new name tag, Lynne Clark." The relief that washed over me felt like a tidal wave. Ms. Mann's compliments made me blush for another reason, but also made we feel really devoted to her. She had intentionally questioned my look to be sure I was okay with it. I knew now that this was how I was always meant to look and how I really wanted to look. The feelings of dressing, applying makeup, doing my hair, all felt so good and appropriate this morning that it had to be right. Now hearing her describe me, gave me confidence that I would never go back to looking like the oddball male image I presented before. Seeing the smile spread across my face, she swatted me on the butt and told me to get my sweet little ass up to the reception desk. I replied yes mam, and strutted toward my new place, my new life. I had entered this summer not knowing what or where I really fit in a business. Now I knew my role in the office and I fully intended to be the perfect secretary. Better even, because I would also be the only one who could draw, design, and image her work. As I reached my station, Ms. Mann let go a low wolf whistle. Turning, I could see a look in her eyes that told me, that more than likely my new submissive feminine place would not end behind a desk, but likely in her bed. I would learn to love serving beneath her in every way. Well at least I would serve her in my fantasies, hoping to make it real. In any case, I knew coming to this office was the best move of my life.