Secretary free porn video

I had begun serving on the neighborhood board to be sure things were done correctly. I had a lot of money invested in my house, and even though I was single, I wanted to be sure it kept its value. The board oversaw all the maintenance and improvements to community property; collected the homeowner dues; made sure everyone obeyed the covenants; and checked that new houses were built to our code restrictions. We also promoted social events and neighborhood parties. It seemed like a lot of work for just 12 people, but our goal was to have the best subdivision in our area. At first I was just a board member, but not an officer. Then after a few years I served as vice-president, an office with very few duties except when the president was out of town. Eventually I even served as the president, with my biggest accomplishment being that I supervised the contracts while we built a new neighborhood pool. Although I felt good about it, the time commitment to being president was a lot, so after two years I stepped down. My replacement, Jolene, wasn't our first female president, but was our first black president. She brought a certain confidence and strength to the position, not to mention being very persuasive and outgoing. Although I was effective within the board when I was president, I am reserved generally, didn't mingle a lot with other residents, and was not a particularly strong advocate for our neighborhood when working with the town or county officials. My weaknesses were Jolene's strengths and I saw immediately that she would be a big improvement. She was a well-known lawyer and used to being in control. I guess that is one reason I agreed to serve as secretary to the board when she asked me to consider that role. Although secretary was an elected board position, it was a very supportive position. It didn't have duties that required leadership or initiative and was viewed by many as a lower level position. You had to be able to take orders and do as the president directed; it was not your place to challenge decisions or look for solutions. The principal responsibilities were taking minutes of the meetings, handling any correspondence, and keeping records for the president. Jolene told me that since I had been president I would have a better understanding of her needs and she felt we would make a good team. The only factor that made me hesitate at first was that unlike Jolene not being the first woman president, I was the first man to ever be secretary for the board. But I had an understanding of how valuable good records were to your success as a president, and I liked her enough that I wanted her term to be as successful as mine was. So I agreed to serve her while she was president. The first eleven months of her term were very effective, with many gains and improvements for our subdivision. Her leadership was very forceful and she applied that control to her relationship with me on the board. The amount of work she asked me to do, was twice what other presidents, including me, had asked of the previous secretaries. We often met at her house or in the clubhouse office to go over documents, presentations, and even financial reports supplied by the treasurer. Jolene told me up front that she could be very demanding and critical. Almost everything I wrote she considered a draft and she edited them thoroughly. Even the meeting minutes, which were rather mundane reports, took an average of three drafts before she was satisfied enough to have me send them to our residents. Jolene also insisted that I accompany her whenever she met with someone, whether it was one of neighbors or the local town mayor. She said I was to take notes for her so she could focus on the meeting at hand, yet still have an accurate summary for her to review later. She used some of our funds to buy me an iPad to take notes and a large handbag in expensive alligator leather to carry it and my other secretarial supplies. It was very obvious to anyone that I was her assistant, both from our actions as well as our appearances. Jolene was a tall, very athletic woman who had played sports in college. She dressed very professionally, preferring tailored suits with trim pants and fitted jackets in muted colors. This conservative appearance was mirrored by her short well-kept hair, minimal makeup, and flat shoes. She projected a business-like manner at all times. Early on she dictated to me that I was to mirror that image. I was not to dress sloppily and was told that dress pants and shirt were required. She was also specific that a tie and suit were not appropriate, although I could wear a cardigan sweater if it was cool, which at first puzzled me. But then after working with her for a while it became clear. She didn't want anyone to miss the point that she was the leader and I was her assistant. I think the fact that I was two inches shorter than her with a thinner, non-athletic build helped reinforce that perception. My appearance had always been a reflection of my freelance consulting work where I did a majority of my analysis on my own and I didn't work from a central office. That allowed me to wear casual clothes almost exclusively, keep my hair longer at shoulder length, and wear small diamond studs in each ear. I essential had the same look I developed in college. Jolene was fine with everything except my jeans and t-shirts were replaced with dress pants and shirts when we were together. As she finished her eleventh month as homeowner association president and we prepared for our annual meeting, Jolene made it clear that she wanted to spice things up. Generally our annual meetings were held in the first week of October in the clubhouse. The president would give a summary of the past year regarding our association's business, the treasurer would provide the financial details, and the vice-president would conduct the necessary election of new board members. It was a fairly low-key if not boring event; with everyone mingling after the formal presentations while we ate some snacks and talked. I think this bland event was responsible for the very low turnout from the residents. Jolene had commented several times, that our social events, like the winter holiday and Fourth-of-July parties, greatly out drew our annual meeting. She felt this was a shame as the annual meeting was important and especially this year since she was in charge. So, it wasn't much of a surprise when she decided that we would try a different approach this year. Louise who was in charge of our social events had added an adult Halloween costume party this year. It was to be held on Wednesday October 28, still near the holiday but not enough to conflict with children's parties or Trick-or-Treating on Saturday the 31st. Jolene announced at the September board meeting that we were going to modify the Halloween event to combine it with our annual meeting. That way there would be more attendance and it would be much more of a celebration than other meetings. The rest of the board really liked the idea, and we were soon engaged in discussions of how to adjust the party plans, as well as choices for costumes and decorations. As Jolene wrapped up the meeting she gathered the officers and told them to consider costumes that would be linked to their board position. For example, since she was president and we had just come off two terms of the first black president in U.S. history, she was going to dress as President Obama. That set everyone talking off again, as it would be a radical departure from her normal conservative appearance to try appearing as a man. As the board members started to file out of our conference room, Jolene looked my way. "Tom, wait a minute I need to talk with you." That was not unusual, as I mentioned, we worked together very frequently and it was almost standard practice that we would go over a few details for 20 minutes after our monthly board meetings. "Of course, Madam President." That was an inside joke I often used with Jolene. I told her once that she created such a presence that perhaps we should give her an official title. I headed to the small business office where we normally met after board meetings. I was shortly joined by Jolene, but she was followed by the social chairwoman Louise, and Beth, another board member. Once inside, Jolene shut the door, went around behind the desk, and sat in her chair. I had already sat down at a smaller chair to the side of the desk where I usually took notes if Jolene was meeting someone or where she gave me many of my other orders. The two women took the primary chairs facing the desk. These chairs were upholstered with arms and sat up a bit higher than my plain wooden, armless chair, but not as high up as Jolene's leather executive chair. Although some might have seen it as a bit degrading to have to sit at such a small child-like chair below everyone else in the room, I had gotten used to it and it did help me focus on the more important speakers in the room. As we all sat facing Jolene, waiting for her to tell us what this was about, I crossed my legs, bringing my feet back toward the chair. I held my iPad waiting to take notes if necessary. "Tom I wanted to be sure you understood my directive at the meeting about our costumes for the annual meeting. I can trust the other officers to come up with the appropriate outfit, but I assumed you would need some help. First, it is pretty obvious as secretary that your costume should be a female one. I don't think you can envision male- based attire that would be as fitting for your office as a female one. Second, since you would likely need help, I have already spoken with Louise and Beth. They have agreed to help you prepare. Third, we also discussed possible options for your secretarial costume and rather easily agreed that a stereotypical look, like the women in the Mad Men TV-series, would be an ideal choice. In that era, the 1950s-60s, women had very feminine and rigid dress requirements, which were enforced even more so for the secretaries that worked in business at that time. Beth has researched some potential outfits that would project that very look. Finally, because you are so much associated with me as president, I want you to be completely believable in your costume. Nothing is as lame or honestly insulting to women as a man who wears a woman's costume in a sloppy manner with little imagination or tries to be a caricature of a real woman. So it will be imperative that you get adjusted to the dress requirements in order to appear fully comfortable in your outfit. I've asked Louise to ensure that you meet those requirements. Of course, I will supervise this process, and both women have agreed to keep me in the loop as we progress. Since the meeting is more than six weeks away, I'm sure we have time to get everything perfect if you give it your full energy. I can count on you to make this work, can't I?" Like so many things Jolene said, this was more of a rhetorical question to me. When she had mentioned costumes related to the board positions, I immediately pictured myself in a 1800s type outfit, with a waistcoat, maybe a top hat; something similar to what would have been worn by the framers of our government, or even a Bob Cratchit-look, similar to an accounting clerk. So hearing her outline my costume as she did was a surprise. Despite being a bit in shock about this turn of events, I nodded my head and agreed to her plan. Louise and Beth also chimed in that they were certain I could be very convincing as a 50s' secretary if I did all that they asked. They wanted me to meet them tomorrow afternoon at Louise's house to begin. That would work for me, as I was flexible in my work schedule. Seeing that everything was settled about my costume, Jolene dismissed the women and we spent some time going over the details of the meeting. After twenty minutes of directives from her, we finished and got up to leave. As she was locking the door, Jolene turned to tell me one last thing. "Tom, I expect you to make me proud at this event. I've always counted on you to do as I've asked and you always deliver. This will be the first time I am in front of the whole neighborhood as the association President and I want it to be perfect. So give it your all during the next few weeks and do everything that Beth and Louise ask of you. If you do that, I'm convinced you can present the perfect secretary image to compliment my presidential one." I smiled and told her I would do my best, despite my inner misgivings. Hearing I was to be portrayed as a woman made me worry about how others on the board would see this especially the other men. The board had been evenly split between men and women. All the men worked full time, while only Jolene did for the women. She said it was good to have representation of the half of the neighborhood that stayed home and were there longer. The split had never been an issue, even though most of the women on the board had been recruited by Jolene and were extremely loyal and supportive of her. That is, until I became the secretary. It became apparent quickly that I was going to vote her way most if not all of the time. I had crossed over to the other side in the opinion of most of the men, if for no other reason than I was reluctant to disagree with Jolene because we worked so intimately together. I could only imagine what they would feel and say once they saw me fully clothed as a woman. I might never be part of the men's club again. But I shook off those feelings and focused on other tasks. You would think I would be concerned about how it might affect my romantic relationships. But to be honest, I hadn't dated anyone seriously in several years, or even been on a casual date in months. Given that I lived in a suburban neighborhood, full of families or retired couples, I never met women my age, at least single ones. So that aspect of portraying a woman wasn't a problem. The next day I showed up at Louise's house at the time she suggested. I was a bit nervous and not sure what we were going to do today, so I went very casual wearing some khaki shorts and a simple polo shirt. She greeted me at the door with a big smile. Louise was a pretty woman, with dark hair, sparkling blue eyes, and lightly tanned skin from time spent running. She was about my height, and probably weight, with long lean legs, average bust size, and an outgoing, friendly personality. "Come on in Tom, this shouldn't take long. We only have a few things to do, mainly to get us started. You know good and well how Jolene can be, so we wanted to be proactive about this whole process. I know you may feel a little uncertain or even fearful of this costume idea, but I can guarantee that you will be the hit of the party. The good thing is that Beth and I agreed that you have all the features needed to be convincing; at least good enough for this event. I hope you have fun with this; I know Beth and I plan to." With that she lead me inside to her kitchen table where Beth sat, drinking some tea. Beth was shorter than us, but average height for a woman. She had light brown curly hair, brown eyes, and fair skin sprinkled with freckles, reflecting her Irish heritage. She was fairly curvy, with a big bust, and although I didn't know her well, she always seemed friendly and outgoing. Once I was seated with my own drink, Beth spoke up. "Tom the two things we need to do today is get your measurements so I can order all the components for your costume and determine what grooming you'll need to be attractive. I've seen you at the pool before and looking at your legs now, I can tell that we will need to remove some body hair if you are to match your costume. You could shave, but if you use a hair remover you can generally get a smoother result that lasts a bit longer. Can I assume you've never used a depilatory before?" A bit more embarrassed at this point as I realized how far the ladies intended to take this, I nodded my head and with a slight smile told them I had never done anything like that. Louise spoke up next. "Well they are fairly easy to use. We bought the spray-on type and you will probably need to use at least one can. The only trick is to be sure to apply enough everywhere and still keep it even. Then you just have to wait a few minutes for it to work and wash off. But as I think more about it, you will probably need to do more than just your legs. Given Jolene's expectations, we'd be safer to do your body too, certainly your chest, arms, and underarms at least. Tell you what, it won't take long, let's just do it now. I think I have an old swimsuit bottom you can slip on and then we will apply it for you. That way we can be sure we do it the way Jolene wants." "It can't be that hard, I should be able to do it at home. I mean women do it all the time, right?" "Don't start that now; you told us you would do what is necessary to make your appearance believable. You're right that women do it all the time, but most don't have a lifetime of hair all over their body to tackle at one time, and their first time wasn't easy either. Just follow us upstairs and we'll have it over in no time." This time, Louise didn't wait for any more rebuttals, heading for the stairs. Beth looked at me and motioned for me to follow and then she dropped in line behind me. Louise took us to her master bath, which was rather nice, with a large walk-in shower, dual sinks, and a luxurious soaking Jacuzzi tub. She went on to the attached bedroom, returning in a few moments with a small floral bikini. It looked tiny in her hands and even worse when she handed it to me, consisting of two small panels connected on the sides by thin straps. The ladies then stepped out of the bathroom. "Just slip off your clothes and put on this bikini bottom." As they shut the door I lifted up the small garment; at least it had a lining that gave it double material. How could I fit in this? Reluctantly I took off my shirt, shorts and underwear. Pulling on the swimsuit, I could tell it wouldn't cover me in front and even in back, the suit only went down halfway on my butt cheeks. I shook my head and called out to the ladies. "Louise, I don't think this is going to work. I mean, it barely covers me in back and there is not enough fabric in front to cover my privates, if you know what I mean. How about I just do the hair removal at home?" "Honestly, we've gone over that already. We are doing here and now. As far as the coverage, I wanted it to be as brief as possible. You certainly don't need a Brazilian-type look, but you will need to be smooth to your bikini line. Try the trick that most female impersonators do, just take your boy stuff and tuck it back between your legs. I'm sure there is enough material there to hold you long enough to do what we need." I was getting frustrated now, but went ahead and did what she suggested. Pushing my cock down and back I could feel my balls slip inside my body. I held my cock tight with one hand, while working the small suit up and around until I had it in place. I had to admit that did the trick although it felt really uncomfortable and much of my pubic hair was poking out from under the bathing suit. I opened the door only part way, as I spoke to them. I was still hoping they would reconsider. "It's better, but are you sure it will work? A lot of my hair is sticking out." I stood where I thought they might be able to see, but still partially shielded. I was a bit embarrassed that merely by putting my cock between my legs that I could achieve a smooth look in front. I knew I didn't have a large one, but still it should have more of a presence than this. But Louise wasn't about to dawdle any longer, pushing open the door and walking in, with Beth right behind. "Oh that will do perfect. I expected your hair to stick out like that. We won't use depilatory under your suit but can go right next to it as long as we trim the longer hair. Take these scissors and you can trim it. Step in the tub, that's where we will work on you." I felt my face turn a bright red, but did as Louise asked and started trimming the hair sticking out from the bikini. It only took a few minutes and when I had cut enough, the ladies started applying the depilatory. They spread it over my torso, legs, underarms and even my forearms. Anywhere that had a significant amount of body hair. After they finished, I stood there giving it time to work, the whole time feeling really awkward. Louise and Beth sat there chatting about possible costumes for themselves, as if this was something they did every day. They also both examined my hair, seemingly pleased at its length and thick nature. They commented that it would do well for a variety of hair styles and that I was lucky to avoid having to use a wig, as they can be tight and hot to wear. Finally, Louise decided it had been on long enough, so she started the shower to allow it to warm up. Once it was ready, they left the room and I stepped in. The foam washed off my body quickly, taking the hair with it. Looking down, I was amazed at how effective it had been as I now looked bare and smooth. Peeling off the suit, I dried off. Wiping down my legs and chest, I was struck by how different my body looked now. Louise had left a pair of plain beige panties for me to slip on while they measured me. Not sure if they expected it or not, but I went ahead and tucked myself again, figuring it might be less embarrassing. As I left the bathroom and entered the master bedroom, both women turned toward me. "Now you look so much better Tom. Your skin has such a nice even tone and so smooth. It really was a shame to hide it under that ugly hair. But what really surprises me is your body. I can almost see a natural hourglass shape. Let's do some measurements to see what we've got." As Louise spoke, Beth had moved around me, checking to see if they had missed any hair. Satisfied, she stopped behind me, and shocked me by running her hand up the back of my thigh, removing it just as she reached the crease where my thigh met my lower butt cheek, at the edge of my panty. Her action caused me to break out in goose bumps and I turned to look at her. She was smiling and winked at me. "I think Jolene is going to really like your new look. She told us that we had to deliver a realistic female. Seeing how cute you look in those panties, I know we are on the right track. Turn around so, I can put this tape measure around your waist. Louise, write down these measurements for me." A bit embarrassed by her boldness, I turned to face her as she asked. She looped the cloth tape around my waist, measuring me above my belly button, which seemed high. I pointed out that the normal waist of my pants was much lower. Beth laughed, and said for women the natural waist was higher due in part to their broader hips. If I was to mimic a girl, then we needed to move your waistline higher and in fact this was the narrowest point of my torso, even if it was just below my breasts. Again her touch sent shivers up my spine. "Twenty-eight inches at the waist; that is really impressive. Most guys tend to be thick in the middle, but you have a trim look. Let me check your hips: 34 inches. Not real big, but your narrow waist gives a good contrast. Okay, let's check your chest, or more accurately your bust. Louise, the band is 36 and across his nipples measures 38. You have a little flesh there, maybe not enough to call them breasts, but certainly your proportions do fit the hourglass body type. We can certainly work with this to give you a feminine appearance. But I need more than those measurements, let me finish with the rest. I'll call out his rise, torso length, leg length, neck, and foot sizes. Just jot them down in that order Louise." Beth continued measuring with the rise being the most embarrassing, since it covered the distance from my belly button down to between my legs and back up to just above my butt. As she lined the tape up, I gave her a questioning look, but she just smiled and told me that it was necessary to properly fit some old-fashioned foundation styles. Since I was going to be a 50s secretary, a good girdle was almost always necessary. When she finished, she went to Louise and they quickly studied the total numbers. They seemed real satisfied with my proportions, commenting several times that I was trim and well balanced and should look nice in just about any dress. I was becoming more and more embarrassed just standing there, and finally Louise noticed and told me I could get dressed. She said to just drop her panties into the hamper in the bathroom, unless I wanted to get a jump on wearing my costume. Beth chuckled at that, but I just went and changed. I couldn't believe what had just happened and my visions for how the party might go weren't looking good. It really struck me how much I changed, after I was dressed and my new bare legs were visible in my shorts. I resolved to wear pants from now on when I was in the public. Not much happened over the next week, but on Thursday I got a call from Beth. She had ordered my costume pieces and they had arrived. She and Louise decided it would be good to try some out to see how I would look. I agreed to meet them at Louise's house at one the next day. I showed up as planned, I knew I would be changing so I just wore my boxers, jeans and long-sleeve shirt, my new standard wardrobe since they removed my body hair. Louise let me in, greeting me warmly. We went right up to the guest bedroom where Beth was standing by the bed. Spread out across it was a pile of women's clothes, including lingerie. On the floor were at least 4 pairs of shoes. I was stunned at the amount of clothing and spoke up. "Wow, this is a lot of stuff for one costume party. Why did you get so much and where did it come from? I certainly won't need this much." "I ordered the dresses and most of the skirts from a vintage clothes site; fortunately you are well within the size range of women in that era. But we will need to check to be sure it all fits you. The lingerie and some of the blouses and skirts came from a site that specializes in bras, stockings, panties, and foundations that overlap the 50s and 60s. All of these items are new, and can be returned if we don't need them. Again, you seem to be a natural size for most of these. Personally, I can't wait to see everything on you. I think you are going to look darling." "I agree Beth. I can't wait to see him in everything. But you know the orders that Jolene gave us. She wants us to dress Tom in one outfit, complete with lingerie, do his hair and makeup to see how it looks. So I guess we will have to spread everything out over a few days. But I'm confident you've picked out sizes that will work for our secretary." "Well, it just seems like a lot for me. I don't know why we couldn't have just used one outfit. I mean, shouldn't a fifties secretary outfit be pretty easy to find at a costume store? A blazer and skirt, or maybe a long dress would do wouldn't it?" "Oh Tom, don't be such a spoil sport. This will be fun, trying on different outfits and looks. Besides, you know Jolene. She is a stickler for details and insists everything be perfect. There was no way she would let you go to the meeting in just any old costume. It has to be realistic, make you look good, and satisfy the requirements of the day. The good thing is we have several weeks to get it right. Besides, unless you've been hiding something from us, you're going to need time to get used to the clothes. It may seem simple to dress like a woman, but just knowing how to move in a skirt or dress, keeping your legs together, and sitting properly will take some practice. Not to mention walking and feeling comfortable in high heels. As for us, finding the right makeup and hair style will take some work too. I don't want Jolene to think we let her down. She's right that not only does the whole costume need to work for you, but it will reflect on her as well. So, given all that we need to do before the party, let's start. I think the first option, would be this nice blue floral dress. It has a full skirt that should hit you right at the knee, a high neckline, with a cute sleeveless look, but should fit tight enough to be sexy. That's part of the costume we need to emulate, the mix between business attire and sex appeal that secretaries of that era were expected to project. Beth, what underwear did you pick out to go with this dress?" "It's the white ensemble. I found a cute bra in sheer white with lace cups that have that cone or bullet shape so common in the fifties. There were matching sheer white briefs and a lace trimmed garter belt that I paired with dark tan, seamed stockings. Of course it needed a couple of crinoline slips to give the skirt its full appearance. Tom, I think if you just change into the panty, we will need to help you with the rest, at least this time. I expect that after a couple of times, you'll get comfortable putting on your own bras, foundations, and hose. By the way, I'd suggest you tuck yourself again, as this panty is fairly sheer." Beth was grinning widely as she handed the full panty to me. I was overwhelmed by both the detail they had put into the outfit, and the indications of how much time this was really going to take. Louise made it sound like not only would I need to try out several different costume combinations, but I would need to practice acting like a woman as well. As I took the brief and went to the bath to change, I had already decided I needed to convince Jolene that this was too much. Once I was alone, I undressed and pulled the panty up my legs. I could tell immediately that Beth was correct. The material was so sheer, that if I didn't tuck my cock back it would easily be visible to the women. Although the style was what some might call a granny panty because it went up to my natural waist, because it was sheer and had lace accents at the legs, it actually looked kind of sexy. Well it would have if it had been on a real woman. Once I had it adjusted, I opened the door and joined the women in the bedroom again. "I see it fits. That's a relief, because often online sizes don't match measurements. Let's get the rest of your underwear on. I'll show you the easiest way to put things on and then you'll know for the future. First the bra: just put it around your waist backwards. That will let you put the eyehooks and loops together to hold it on. Then spin it around so the cups are in front, slide the straps over your arms and pull it up to hold your breasts. In your case, once you have it in place we can fill it with forms. As you get more comfortable with the design, you can put on your bra by slipping your arms through the straps, reaching back and hooking the band, and then adjusting the cups in front. Either way will work." I did it as Beth first described, until I had the bra positioned correctly on my chest. Seeing I had followed her instructions, she continued. "What's so cute about this bra is that the cups are super pointy. So pointy, that even if you had breasts, they wouldn't fill the tips. So the company sells these little cone pads that fill out the tip of the cups. I also bought you some silicon forms that replicate normal breasts. These have attached nipples, can be glued on if we want, and are the top of line. Jolene told me not to scrimp on the accessories. So go ahead and fill up your cups." Again I did as she directed and I could tell that she must have ordered a large size, because I now had two cones jutting forward from my chest; they looked huge. Beth handed me the garter belt next, and I hooked it in front and slid it around, similar to the bra, until it was in place too. She showed me how to bunch up the stockings to slide them up my leg. She pointed out that I had to keep everything lined up, because there was a dark seam running up the back of the stocking. It took me a few tries on the left leg, but I soon had it attached to the garter belt with a straight seam. The right leg went a little quicker. Beth laughed and commented to Louise that I seemed to be a quick study. At that point, she said I was ready for the dress and held it for me to step into. Once I had both feet inside the skirt, she pulled it up, moving it over my pointy boobs, and then zipped up the back. It fit comfortably, if a little snug, with the clingy fabric molded over my cone-shaped breasts. With the dress in place, she got the two crinoline half-slips and helped me pull them up under the dress. The change they made in the dress profile was very noticeable, as I now had a full skirt that ballooned outward from my narrow waist. Beth slipped the shoes, pumps in a blue that matched my dress, on me to complete the look. I tottered a bit in the heels, but the women loved the total look. "Beth you did a fabulous job with this outfit. It so looks like the fifties, with the full skirt and pointy breasts. Even the stockings with their seams and reinforced toes and heel, everything is so accurate. I assume you've got a hairstyle in mind to go with this outfit?" "Yes, I think we will just do something simple. A side-part, with sweeping bangs, and lots of curls at the end should be enough. The makeup will look simple too, although it will take more work. He'll need full foundation, concealer and blush to give his face more of a female contour. His eyes should be spectacular though, with eyeliner, sultry shadows, false eyelashes, and mascara. His natural blue color is already attractive, but with makeup I can make them stand out. I'll finish it with a nice solid red color for his lips. For the party, we'll match his lipstick shade to his nail polish so, he'll be fully coordinated. The final touch will be his accessories. I bought a slim ladies' watch in silver with a set in matching simulated pearls of bracelet, necklace, and pierced dangly earrings. I think Jolene will really approve of this outfit." With her plan laid out, Beth and Louise went to work. Louise curled my hair with a curling iron and Beth applied the makeup. It seemed to take forever, as it was embarrassing to have them fussing over me and making comments about cute and sexy I was looking. After an hour, they had me fully costumed. Standing in front of the full-length mirror, I could see they had done a good job. I had to admit, I did look very feminine and a good match for the fifties image they were striving for. They had me get up and walk around a bit and it was obvious that I was not adjusted to the 3-inch heels or even moving with such a full skirt. Seeing my difficulty, Louise spoke up. "Tom, although I think Beth has nailed your look, it is obvious you are going to need some practice to get your image right. I've got a plan that will help with that, but first I need you to strike a pose. Jolene wanted us to take a few photos of your outfit and send them to her cell, so she can check it out. So, why don't you stand over by that chair in the corner, so I can get the whole outfit?" "Wait, nothing was ever said about photos. I mean, that seems a bit much. Can't you tell her everything looked okay?" "Hello? We're talking about control freak Jolene here. How many times does she re-write just the simple notes you take in our board meetings? You really think she is going to be satisfied with us telling her what it looked like? Of course, I could call her now, maybe we could just go meet her somewhere, maybe grab a cup of coffee, and she could check you out that way, if you'd rather not use a photo. How does that sound?" Grumbling, I knew Louise had me. No way was I going anywhere today looking like this. Although, I suspected it was an empty threat anyway, I took no chances and walked over to the chair. Smiling, Louise told me how she wanted me posed, took several photos with her cell, both front and back, and then sent them to Jolene to review. "She'll likely get back with us tonight or tomorrow, but we can go ahead and work on getting you used to walking in heels and adjusted to how your costume feels. I wish I had time now to stay here and give you pointers, but I have an appointment in about 15 minutes and I need to leave. But I do have a few things you could do for me in the basement; some simple chores that will help you get more comfortable in your outfit. Beth, I know you need to leave too, so I'll check in with you after I hear back from Jolene. We can decide what's next at that point. So Tom follow me and I'll get you started." We left the bedroom following Louise. Beth continued out the front door while we went to the basement. I had to go really slow, as each step in the heels was an adventure. It didn't help that I couldn't see my feet beneath my billowy skirt and had to move my arms differently due to my new 'breasts'. I wasn't sure anyway, that I understood what Louise had in mind for me to do. We finally got to the basement, which was finished. It consisted of a main recreation room, a bath, and a laundry room. Louise stopped in the laundry. "Tom, the first thing you need to so, is walk around more in your heels. Nothing will help you adjust more than just doing that. Second, I want you to get used to how your new costume is wider and restricts your movement, as I'm sure you noticed coming down the stairs. Third, you need to practice moving in a more feminine way, especially your stride, how you hold your arms and hands, and the art of sitting down in a chair. As I said upstairs, if I had time, I'd just sit here and ran you through some practice, but since I don't you will work on your own. It turns out that I've got a few things you could do for me, while you practice. As a starter, I've got some wash in the machines. The dryer has clothes that need to be folded and the washer has a load that needs to be transferred to the dryer. If you will take the clothes out of the dryer, fold them, and then stack them on the table next to the stairs that will help. You can also do that for the clothes currently in the washer after their cycle in the dryer. As you work, try to concentrate on taking small steps when you walk; a woman's stride is normally much shorter than a man's. Try walking more on your toes, at least till you get used to the higher heel height that can help you adjust. If you aren't carrying anything, keep your arms tucked to your body at the elbow, with a limp wrist, hands relaxed. Going through doorways, you may need to grab the sides of your dress and crinolines to fold them inward. It's not good to let them just brush the frame as you go through. While you wait for the second load to dry, use the vacuum against the far wall to clean the carpet in the main room. That will give you more practice walking and negotiating furniture with your wider skirt and I imagine having a bust will take adjustments too. In between, practice sitting down. I know that sounds silly, but you need to smooth out your dress and crinolines as you go down, so they don't get wrinkled. I should be back in an hour or so, but if you finish those chores, take the clean clothes upstairs. Putting them on my bed will be fine. After I'm back, I'll see how you're doing and then we can remove your makeup and you can change out of the costume. Are you clear on everything?" Although I was a bit perturbed at having to do chores for Louise, I just nodded my head in agreement. "Well okay, I'm off. I think you are doing wonderfully and I really appreciate you helping me with these things. I needed to get these done, and since we spent so much of the day on your outfit and appearance, you helping me will make up for that. One last thing we need to do is put on an apron. Beth ordered a full skirted, bib style. It's hanging on a hook in the laundry. Just wear it over your outfit that will help keep it clean while you practice. If anything comes up, just ring my cell. By the way, my husband Jay usually gets home after 6 and the kids won't be here before 4. See you later." It worried me a bit to be in Louise's house alone, especially since her family could come in and not know anything about me, but I started on the tasks she had outlined. I found the apron, put it on, tying it in back. I tried to think of the assignments as training exercises, rather than chores, because it felt like I had been taken down a peg. I focused on walking as she had described and carrying my body as she wanted. It felt really unnatural and I had to exert a lot of effort to let my arms go limp; that seems like a contradiction, but men tend to be tense and hold their muscles at the ready. The work itself was easy, as I did my own laundry and housekeeping. The chores, okay that's what they were, went quickly and I even had time to carry the folded clothes up to Louise's bedroom. I had to admit doing work forced me to move and walk like a woman and I was able to get past having to concentrate on my actions until they became more instinctive. I started getting more worried, as it was already 3:30, close to when her kids would arrive. I didn't want to be here when they got home. Finally Louise returned. She was generally pleased with the fact I had finished all the assignments and complimented me immediately on how femininely I moved. I had figured out how to walk without wobbling in the heels, but they were getting a bit painful, so I was glad to change out of my costume. Louise showed me how to remove the makeup. I brushed out the curls in my hair, and then dressed in my regular clothes. Louise had me put my costume in the guest bedroom closet and a small dresser; although she wanted me to take the panties home and wash them out by hand. Also she noticed when I was getting dressed that my toenails were a bit rough, and I had some callouses on my feet. If I was going to continue to wear hose, that would likely cause a snag or run. Louise said she had a great manicurist, so she gave me her number and told me to make an appointment for a pedicure. I wouldn't need polish, but she could make my nails and feet smooth and soft. Louise indicated that she would call me after she got some feedback from Jolene. I was gone just as her kids came up from the bus stop. I heard nothing from the ladies for a few days, which was fine by me. But I did make an appointment to get my feet done. Surprisingly it was relaxing and felt good, once I got over the initial embarrassment. When I looked at my smooth feet and buffed nails I could really tell a difference. They were such an improvement I went along with the manicurist's suggestion that she do my fingernails as well. I finally got a call from Louise. It turns out that Jolene liked the dress, but wasn't sure it was really the most appropriate look for a secretary. So she asked that we try another one. Louise also mentioned that Jolene had wanted to see the lingerie we used for each costume, so before we tried on a new one, I would have to put on what I wore the first day, so she could take some photos to send to Jolene. She told me since I had washed the matching panty, to just wear it over when you come. Because she felt like we had more to do, Louise asked me to be at her house at 10:30 the next morning. I agreed, but I had already decided to call Jolene and stop this now. As soon as I hung up the call, I dialed Jolene's number. "Hello Jolene, yes I'm fine. How are you? That's good. I just wanted to talk a minute about the costume party the board is having for our annual meeting. I agree that it is a cute idea to combine the events, and even to have the board dress appropriately for their offices, but I think we're going too far with choosing my secretary outfit. I know you want everything to be perfect, but the outfit that Beth put together should fit the bill. I mean it really looks like something from the fifties and it actually fits me, so let's just go with it. Looking at all the clothes she ordered, it seems like overkill and it has to be expensive for all that. I mean it is just one night." "Well Tom, I'm glad you agree that it's a good idea for the party event, but I think you're underestimating how important it is to find just the right outfit for you. First of all, you are going to be wearing a woman's costume, so there is the hurdle of having an outfit that makes you look convincing. You did look okay, and if I didn't know it, I would have assumed you were a woman. Second, the outfit has to convey your role as a secretary. I know the dress that Beth picked reflected the fifties'. I mean what other era had such full skirts and those cone-shaped breasts, but when I first saw the dress I thought more of a housewife. I want you to look perfect. If this costume does that better than the other choices, then we can come back to it. The good part is we have time to choose, and I decided that we could use the discretionary funds to cover these costs. I mean the other board members will be able to come up with costumes that are fairly straight forward, but yours is more difficult, so it is only fair to cover that expense with the extra funds. Plus there is the matter of you achieving more natural feminine behaviors. Louise said you made progress in how you walk and your body language, but she said you need more practice." "I guess I see the value in what you are proposing, but Louise said you wanted photos of the underwear for the outfits. What do you need that for?" "Come on Tom, you know how I much time I spend on each detail of everything I do. If I can't understand how the shape you have is achieved in a costume, how can I be sure we've done everything possible to give you the perfect look? I mean, I trust the ladies to a certain point, but it will still be my call. If I want you to wear the underwear combination from one outfit with another one, then I need to know all my options. Take this like an order given a secretary by her boss in the fifties. Just don't worry your pretty head, trust me, and do as I ask." Jolene laughed as she said this last part and I knew the argument was over. I had worked with her enough to know when her mind was made up it was fruitless to keeping arguing your point. So I decided to just limit the damage. "If you insist that I try other outfits, can you at least tell Beth to pick the one she thinks best represents the fifties' secretary? That might save us all some trouble." She agreed that would be okay, and we wrapped up the call. Reluctantly I realized I was just going to have to work my way through this whole episode. So the next day, I showed up at Louise's house wearing my freshly laundered panties under my male clothes. When she answered the door, she welcomed me, told me that Beth was running a bit late, and maybe I should just go on up to the guest room and put on my lingerie from the previous time. I agreed and went upstairs. It seemed more than a bit odd to be putting the same underwear on that I wore last time, but at least now I knew what to do. I was able to get everything put on, adjusted and was just beginning to really feel uncomfortable being dressed only in my underthings, when Beth arrived. The women joined me in the bedroom. "Tom, I think the best way to do this will be to go ahead and put your makeup on and get your hair started. I want to try a curly hairdo today, so Louise has plugged in her hot curlers. Once your hair is rolled and you are made up, she can take a few photos for Jolene of the underwear from your last outfit. Then you can change into your lingerie for today. This time we'll get photos of that before completing your costume." I nodded my head in agreement and went to the closet to retrieve the blue pumps. I slipped them on as I sat at the vanity next to the window. The women began working immediately, Louise curling my hair while Beth did my makeup. This time I could see what both were doing as they worked. I guess it made them feel more connected to me to explain each step as they went. At first they tended to talk over each other, but after a couple of minutes they worked out a rhythm. I could actually understand what they were doing this time. Soon my head was covered by twenty or so curlers; I could feel the heat from them on my scalp. Louise worked a hair net over them to keep everything in place. Beth finished shortly after my hair was set. She used almost the same approach to contour my face; the application of concealer, foundation, and blush seemed straight forward. Beth did use a different set of colors for the eye shadow and lipstick, being a brighter pink this time. It was a bit harder to see how she did my eyes, as I was either looking up or down, depending on exactly what she was applying. It still amazed me when she was finished; my face was distinctly feminine, although still recognizable as me. When they were done, I stood up to pose for the photos; it seemed silly, but Louise had me lean over to look in the vanity mirror, as well as stand up, with my hands lightly touching my curlers, as if checking to see if they were dry. She commented that she didn't like taking 'line-up' photos, and these should show Jolene how everything looked without being dull. After what seemed like way too many photos, Beth said I could change into my next outfit. She laid out the lingerie on the bed, and the dress was hanging on the closet door. Looking at the lingerie, I was puzzled. I could recognize the panties, beige brief with all over lace, and the matching stockings, but one item seemed like a hybrid of a bra and a girdle, with garters hanging off it. The ladies laughed when I mentioned it. "That's what's known as an all-in-one, or a torsolette. It is like you said, a combo bra and girdle. It can be a bit of a chore to get on. You put your panty on first and hook the stockings last. To get started, you will have to bunch it up at the middle, step into it and pull it up to your waist. This may take some doing as it is fairly controlling, but for you it should a bit easier as you don't have wide hips. Once it's on your waist, pull the bra section upward, slipping the straps over your arms. With the bra in place, pull down the girdle over your hips. At that point you can zip up the side zipper which will tighten everything. You then attach your stockings to the garters, and put the forms in the bra cups. As odd as it looks, it was very common for women to wear in the fifties as it gives all over shaping and control. We could help, but I think it's better if you learn to do as much of this on your own as possible." "Okay, I'll give it a try. Once I have on the underwear, do you want me in my heels and jewelry as well for the photos?" "Yes, just come out and we'll get some cute shots. Then we can get the dress on and comb out your hair." I did as the ladies asked. It was a bit of a struggle getting the tight girdle up to my waist. I'd hate to imagine what bigger women did back in the fifties with such a garment. It gave me a well-defined profile, with a narrow waist and cone-shaped breasts .The rest went more or less like they described and I soon was out for photos. Beth really liked posing me and tried some new shots, like having me lean in to the mirror with mascara in my hand, as if I was doing my eyes and she unhooked a stocking and had me pose re-attaching it to the garter, with my leg extended. It all seemed way overboard, but I went along to get it done. When the lingerie photos were done, I put on the dress. It was a brown and tan tweed sheath dress. It was a fitted design, with a high neckline, pencil skirt, and ? length sleeves. It featured a series of three large bows running down the left side, starting right below the shoulder, one at the projection of my padded breast, and one above the waist. These bows were matched by one at the back of my skirt, where there was a modest slit. The bow decoration was continued on the toe of my shoes. Overall the dress hugged every curve, and without the tight body girdle, I wouldn't have been able to wear it. Even sitting down to slip on the brown sling-pumps seemed like a chore. When I was completely dressed, Louise came back to do my hair. Removing the curlers, she teased and combed my hair so that I had a very bouffant style. It featured high side-swept bangs, lots of volume, and loose curls all over my head that required lots of hairspray to keep in place. She finished off the look, with a large brown tweed bow that matched my dress. Beth touched up my lipstick a little, and then I posed for pictures. She had me sit with a note pad, as if I was taking dictation, stand with one hand on my hip, and a phone to my ear, or just with my elbows tucked to my side, arms extended with a limp wrist. Once she was done with the photos, she explained her plan for rest of day. "Like we did before, we want to get you more practice in the heels and today, learning how to walk in a tight skirt. You'll find that it will be necessary to take even smaller steps, as the tight hem of your dress will limit the range of movement. Because this outfit is tight enough that your hips and butt are more visible, I want you to learn to move your hips like a woman. An easy way to practice is when you walk imagine a line in front of you. As you step, bring your foot inward so it would land on that imaginary line. If you do that, it causes your hips to sway and wiggle a bit more like a woman would. While you walk, try to maintain an upright body position, with your shoulders back and bust forward. I also think you'll need to adjust to wearing a girdle; it's much more restrictive than the garter belt you used last time. You'll probably need to take smaller, more frequent breaths since it compresses your torso and diaphragm. But the good thing is, your body can be pretty flexible and you'll learn how to cope with it. Seeing how well you did last time, I have faith that you can get where all your movements have a natural feminine flourish. The final thing I want to start working on is your voice and speech. Women have a higher, softer natural tone to their voice and then tend to phrase things much differently than men. To practice all that, I've planned to have you do several tasks today. First, since it is about time for lunch, I want you to prepare and then serve Beth and me, as if we've come over for a ladies' luncheon. I've prepared a salad and bread sticks, as well as drinks. Everything is in the kitchen. There is a tray on the counter and I put your apron over a chair. Because we want you to be a fifties' woman, there are actually two aprons, the full white one, which you can use to get everything together, to set the table in the dining room, and when you do the dishes after the meal, as well as other household chores. But Beth also ordered a half-apron. It is sheer white, with Swiss-dot and rose decorations on it and a flouncy lace hem. It's commonly called a hostess apron, and almost every woman in the fifties' had several. The idea is to wear it when you bring food to your guests, or drinks, or serve them in any way. So after you've got everything ready, put on your hostess apron and we can eat together. After lunch, Beth and I need to head out for some errands, so I'll leave you a list of things to do. That way you can practice walking, bending, sitting, and generally get used to your outfit. The more you adjust to the restrictive feel of the girdle the better off you'll be, because the rest of the outfits all include one of one style or another. Do you have any questions, Tom?" It seemed like way too much, but I knew any protests would be ignored, so I just smiled and said okay. I went to the kitchen to get started. I could tell immediately that walking in this dress would be so different. Also, it was hard to remember how to hold my arms, adjust my stride to create more hip movement, and maintain an upright posture. I didn't want to say anything, but it had been automatic to slip back into my male movements during the gap between my dress fittings. The prep in the kitchen and dining room did not take much work, so I soon had everything ready for lunch. I changed to the half-apron, marveling at how different times were then. There is no way you could get woman to wear such an item today, or even an outfit like this one. It was almost like the male fashion designers were requiring such restrictive and frivolous outfits for women just to keep them in their place. It was hard to imagine seeing yourself as anything but a man's plaything or servant in these get-ups. Once I had the food and table ready, I called the ladies in. We sat around the table, just talking like we would in any situation. But with almost every time I spoke, one or the other would critique or comment on my speech, the inflection, or even the choice of words. For that reason, lunch took longer than I expected. Also, Louise commented that I didn't seem to be carrying myself with the same feminine style that I had developed by the end of last time. I agreed, saying it was hard to remember all the body language differences between a man and a woman. We talked a bit more about it, and then they had to go do their errands. Louise gave me the list as they headed out. The chores were mostly routine ones with a fair amount in the kitchen, cleaning counters, sinks, and table. I also used a dry mop to pick up dirt from the floor. Other chores like gathering up dirty clothes from the bedroom and taking then to the basement to put in the laundry, or making the kid's beds and picking up the mess from their floors, or taking recycles and old newspapers from the kitchen to the garage, all seemed designed to keep me in motion, practicing my walk and getting used to the tight skirt. By the end of the afternoon, I was dying from the girdle. The shoes weren't as bad this time, I had at least adjusted to them, but the girdle seemed so tight and unbending, that it affected all my movements. Finally, I heard Louise's car return. Once she was inside, I gave her some demonstrations of what I had been practicing. She really liked how I had improved my walking, complimenting me on my natural hip wiggle. But I hadn't got my arm position or my limp wrist and relaxed hand back to where it had been the previous time. "It disappoints me that you seem to have regressed on your behavior. You've added a sexier, more feminine walk in your hips, but your arms and hands are all wrong. Plus, you are hunched over too much and seem stiff in some ways. Your speech made some progress, as you consistently use a soft and higher pitch in our conversations, but your sentence and word structure is still masculine. I hoped you'd pick these things up faster. Is that what you see Beth?" "I agree totally. Tom started really well last time, but it's as if his memories of the changes just evaporated since then. The fact that he picked up the walk so quickly and elements of a woman's voice shows me he has the potential, but maybe we aren't doing enough. I thought if we got together a couple of more times before the party that he would be fine, but now, I'm not sure. What do you think of doing four or five days of consecutive practice? We could get him into all the costume choices, let him have more time to adjust and then see where we stand?" "Wait a minute, I understand you think I need more practice, but I've got things I need to do as well. Even though I manage my own time, and work from home, I have deadlines and meetings too. So although I see where you coming from, we need to realize this is just a costume party and if I don't make a perfect fifties secretary, will it really matter?" Beth and Louise both looked at each other and back to me as if they were surprised I interrupted the conversation. They seemed both exasperated and angry that I would try to interject my view into the decision. Beth shrugged her shoulders and rolled her eyes at Louise, who just smiled. She turned toward me like I was a child or a simpleton. "Okay Tom, we understand you have needs as well. But I don't think that they are that big a problem. Certainly not big enough that we want to jeopardize what we've started here. Jolene assigned your costuming and conversion to Beth and me, and we intend to complete the assignment. What we will do is accelerate your costume tryouts, so Jolene can have time to select your debut outfit. After that, we can dial it back to a more practice level. Beth, how about this plan: Tom comes over the next two days to my house and we get his last two outfits photographed and fitted. We expose him to all the feminine behavior, movements, and conversation requirements we want implemented. Then he can transition to doing these at his own place. We will check in on him, but he will be free to do his business work and his own housework. After a few days of this, we can see if need to adjust his training as we get closer to the party." "I like that plan. I also think we need to let him be more invested in his conversion. If he does his own hair and makeup, it could help him with his feminine behavior. If we follow your plan, do more with him the next two days rather than leave him alone, we can give him instant feedback. My problem is timing. What's your schedule look like the next two days? I'm available mid-day tomorrow and the morning the day after." "Tomorrow's tight for me to, although I can be here to get him started. If you can pick up for me in mid-day, I can join him late afternoon. The day after is better, if you can cover the morning. I like your ideas on makeup and hair. I was thinking if he rolls his own hair tonight, when he comes over tomorrow, then we just have to brush it out and spray it. We can show him how to do that from then on. That saves time. Same with his makeup, once he gets basics down, then he can do his own. Also there is no reason, he can't take the lingerie that works with each outfit and he can get dressed in those at his house." I stood there as they talked, feeling left out and helpless. I tried to interject once, but Beth put up her hand and shushed me into silence. Finally when they worked out their plan, they made a schedule and gave it to me. We went upstairs and I undressed. Because I had done more walking and work today, Louise had me put both the all-in-one and the panties in her dirty clothes hamper. She said one of my chores tomorrow, could be learning to hand-wash delicate items, so those would be part of my assignment. She dug out a bag of old-fashioned plastic curlers. Briefly showing and describing how to set them and a pattern I could use to do all my hair, she gave me those. Beth had gathered the lingerie and hosiery for tomorrow's costume and put it in a floral tote for me to take home. The more they talked they decided if I wore a robe over my lingerie, then I could just go home in my outfit when I was done. I tried to interject but again they ignored me. Beth said she was leaving early tomorrow and if I wanted then she could pick me up to drop me off here. Louise said that would work, as she could take me home at end of the day. By now I was getting frustrated, but I felt helpless because I had removed all my clothes and was sitting at the vanity removing my makeup. Finally they were satisfied with the plan and let me get dressed. I headed home, happy for the day to be over, but dreading tomorrow, well even tonight as it dawned on me I would be rolling my hair before bed. I ate a light dinner and spent the rest of the evening working. I had a lot to catch up on, as I had a deadline at end of the next week. After making good progress, I decided to take a shower, wash my hair and try to roll it. Following Louise's instructions, I managed after a few first time failures to get all my hair in the curlers. Once I figured out the system it was straight forward. First I worked curling gel into my hair. Then, I sectioned my hair into three areas, top center and each side. Starting with the top near my forehead, I used the small comb Louise gave me to separate a lock of hair that was about the size of the roller. Rolling the hair around the curler from the end all the way to the scalp was easy, as the brush style of the curler grabbed the hair. I just clipped on the plastic holder to the curler at that