I had been looking for work in the want ads and noticed there weren’t many choices. Most of the jobs were menial labor or fast food types and didn’t pay much. But I did find a job opening listed at a local law office. I circled the ad then drove down to apply.
I entered the small out of the way building and noticed a stack of papers and books on a couple desks in the main office. After asking if anyone was in I heard a ladies voice. She told me to come into her office. I entered to see her moving about the paperwork while she talked on the phone. After she motioned for me to take a seat I waited until she was done with her call.
“Can I help you?” She said with a smile. I showed her the ad she had placed in the paper for a legal secretary. She took her seat and looked me over as I handed her my resume.
“I do need a secretary very badly as you can probably tell from the mess of papers and books in here” she said. “I know these days that there are a lot of male secretaries out there and you seem well qualified” she continued “but I am more in the market for a woman secretary, it’s more traditional, you understand.”
I told her that I had a degree and would rather use my brain than have to twirl either a spatula or a shovel. She seemed to understand as I continued about really needing a job and after I nearly begged for the chance she finally relented.
“You don’t mind doing what is usually women’s work then?”
I told her I didn’t mind. With that she hired me and had me report bright and early the next day.
It didn’t take long to get the place in shape and within a couple weeks I pretty much learned all I needed to know. I worked at my desk answering the phone and typing reports in the outer office and Donna worked in her private office. She was a good lawyer, was in her early 50’s or so and had a bit of a buxom build. She was larger than I was and with me being slightly built and short as well she was also a couple inches taller. She often teased me that I should maybe wear high heels around the office so I could be taller than her! I then thought it a bit strange as I noticed that her clothing seemed just the slightest bit masculine in appearance.
I passed the comment off until a couple weeks later. I had been working there for a month and everything was rolling right along when one Friday afternoon Donna called me into her office. It had been a bit slow that week and it was nice to not have to hustle quite so much and I thought that after the work got down to a routine it would be a pretty good job, especially since I was making about ten bucks an hour more than most any place else in town. I went into Donna’s office and after closing the door behind me took a seat and awaited what she had to say.
I figured it might be some extra work, or maybe her thanking me for getting everything caught up or maybe even her telling me I could leave early for the weekend but that isn’t what happened. She rummaged through her desk drawer then brought over a small, paper bag package and handed it to me. I opened the package and reached in to feel something slippery and silky then pulled the material out and noticed I was now holding a pair of ladies panties! They were full cut, white nylon briefs and very feminine all done up with lace and bows!
“What’s this!?” I questioned with a funny look on my face.
“Just a little something for you Dennis” she said with a smile. “I’d like you to start wearing them under your suit when you report for work. And don’t worry, I will pick up enough of these pretty, feminine panties to keep you properly dressed from Monday through Friday. You don’t have to pay me for them, consider them a bonus.” She said as she returned to her desk and took her seat.
I folded the panties and put them back in the bag. “I don’t think so Ms. Roberts.”
She didn’t like my apparent stubbornness.
“What did you say?” She said.
I repeated that I wasn’t about to wear women’s panties but she only giggled slightly as she continued.
“I told you this was traditionally women’s work didn’t I?” She said.
I said that I remembered that but continued on thinking she was joking. I got out of my chair saying I had work to finish before five o’clock but she replied by saying “you’re not dismissed yet! Pick up that package,” she said with a demanding tone. “Monday morning you will come to work and I will check to make sure you are properly dressed.”
I told her I wouldn’t do it! She then ended the argument.
“You’ll report to work on Monday wearing these panties under your suit or you’ll look for another job!” She said with authority.
She relaxed a bit by telling me it really wasn’t that big a deal and that I would get used to it.
“I just like knowing my little secretary is dressed just a little feminine underneath. And what’s the worry? Who’s going to know?” She finished, then said I could return to my work.
I didn’t know what to think! If I didn’t do what she said I would be out of a job and in a real jam! I quietly gathered up the package then left her office closing the door behind myself as I left.
I dreaded the following Monday morning. I got up, showered and got ready for work. I took my suit off the hanger and grabbed a fresh shirt and tie then noticed the package Donna had given me sitting on the dresser. With no way out at least for the moment I took the package, reached into it then took out the panties and began putting them on! I finished dressing as usual and then drove to work.
I entered the office and had just started for the coffee machine to make coffee when I heard Donna call me into her office. I entered the office and as I closed the door she was already moving towards me asking how my weekend was. She then moved in close and reached for my pants! I startled back. “Just relax now, I’m not going to bite!” She said as I stood there.
She reached over and holding my belt with one hand unzipped my pants with the other. She then reached in and felt the front of the panties I was indeed wearing. She felt the creamy smoothness and could feel the lace trim at the front and the little bows at the front of the lace trimmed legs.
“Feel good don’t they?” She said with a wicked smile as she felt me through the panties.
Just as she started to stroke my member I pulled back and she withdrew her hand and returned to her desk. I could feel my face redden with embarrassment as I quickly zipped back up then mentioned that I had coffee to make.
The morning went as usual until after lunch. Donna got back about a half hour late and after hanging up her coat she smiled and put another package on my desk as she left for her office. I could tell the package was from one of the local lingerie stores. I couldn’t believe she was serious but realized she was as soon as I looked inside and saw another dozen or so pairs of ladies panties! They were in several pastel shades and all the full cut type and all had lace and were adorned with appliques and other lacy trim and little bows. I quickly closed the package and put it in one of the desk drawers realizing that I would now be wearing panties to work every day! I was a bit sickened to see that the days of the week were embroidered on one set of the panties as well when I got them home and took them out of the package!
The next morning I was back in Donna’s office for inspection. She had me take my pants down this time and then rubbed her hands over the cool, slippery pink fabric.
“My, you seem to like the pink ones hummm?” She said with a giggle as she looked me over then pulled them up tight on my waist and squeezed and rubbed my bottom through the shiny nylon.
I asked how it could possibly matter which color I wore and she giggled, satisfied I was still following her orders.
“But there’s one thing though,” she said as she looked me over. “I’d like to have you start shaving,” she said as she saw the sparse but noticeable hair on my legs. I felt shocked!
“Shave?” I said with a gasp.
“Yes, you’ll look so much better in these when you are properly shaved,” she added as I pulled my pants back up.
“How much to I have to shave?” I asked in quiet terror.
“Everything silly!” She said with a giggle. “Tomorrow morning I will expect to see you nice and smooth all over without a hair below your eyebrows except for your ‘bikini cut’ down below” she giggled at allowing me to keep a little hair.
I pleaded with her to not make me do this but she was insistent! It was either that or get ready to start looking for another job with what most likely would be a menial labor one with a lot less pay! I quietly returned to my desk and finished out the day.
The next morning it was inspection time with Donna again in her office. This time she made me strip down to my socks and panties while she looked my now totally shaved body over! Later that day she called me in to her office once again and this time handed me several pairs of nude, support pantyhose! I knew what was next. Now in addition to wearing panties to work I would now be wearing women’s hosiery to work too! And the next day it was another inspection. Donna noticed my panties under the shiny nylon pantyhose as she fondled my now shaved and nyloned legs!
“Mmmmmmm, don’t they just feel delicious?” She said as she marveled at how the nylons shined in the light and how they felt under her hand as she rubbed the material against my legs! I started having second thoughts about continuing working for Donna and even though I needed the job I thought about just quitting while the quitting was good.
But as I finished pulling up my pants and tucking in my shirt once again Donna told me she was giving me a raise for my being a good secretary and such a good sport. She then handed me another package and told me how nice I would feel with a pedicure! Then once back at my desk I noticed the nail polish and other do-dads in the package!
The days went by and with the workload I found I actually forgot about the panties and pantyhose from time to time, just like Donna had said by saying “don’t worry, you’ll get used to them in no time.”
With another week came another feminine addition to my lingerie wardrobe, and then another, and another! The following Monday I was standing in Donna’s office before starting work while she looked me over once again. By now, she really had me decked out! I was wearing my panties and pantyhose complete with my now red nailed pedicure done up in a bright gloss red that showed through the toes of the stockings. She had also added a tight girdle briefer panty to my wardrobe and showed me how she wanted me to “tuck” myself so I wouldn’t show a bulge. Finally, she had me wear a pair of white nylon pants liners and finished the look with a matching, lace trimmed nylon camisole! I was now, underneath, totally dressed!
I begged her to let me take off the camisole saying the straps would show through my shirt but she wouldn’t have any of it! She said if I was worried I should start wearing T-shirts and / or keep my suit coat on at all times. I thought the next step was the last straw though because the following Monday, she brought a pair of high heels to work that were in my size!
The shoes were black patent leather pumps and Donna made sure to get a pair with open toes to show off my painted toe nails! I was grateful that most of our work was corporate and didn’t involve a lot of walk in traffic but I drew the line at wearing high heels and complained immediately!
“What are you doing to me Donna!?” I asked with a quizzical glare as I stared at her. But she only smiled with her usual air of authority knowing full well who was in control.
“I thought you said ‘who’ll know’ and that nobody could tell I was wearing ladies lingerie? If I wear these shoes around the office what happens when somebody comes in!?” I said in a terrified tone. “They’ll freak out!”
“Don’t worry!” She said. “You just get yourself a pair of loafers and keep them under your desk. Then, if someone comes into the office you can change shoes without them knowing.”
“But what about these nylons?” I said pointing to my ankles.
“Your pants are long enough, just put your dress socks in the drawer until you leave at night.”
She had it all figured out and even though I tried to argue further it did no good. Then she told me If I could learn to master the heels in a week she would give me another raise!
It became very strange almost surreal. She watched as I went back to my desk and took off my wingtips and black dress socks. My nyloned feet complete with red nail polish were now clearly evident! And worse now because I was stepping into women’s high heeled shoes! Donna smiled with satisfaction at seeing them on me.
She had to help me stand at first and giggled as I wobbled on the five inch stiletto heels as I moved around the office doing nothing more than trying not to fall. She had me continue to practice and coached me how to step until I started walking a little better. She then returned to her office. An hour later I heard her ask me to bring her in a fresh cup of coffee. I knew what she wanted, she wanted to see me mincing on the heels and did just that as I carefully made my way into her office with the hot coffee. Donna thanked me then watched as I teetered, the heels forcing my hips into a slight wiggle as I moved back to my desk. And that’s how it went.
As the days went by I would put on the high heels immediately after arriving to work and leave them on until my lunch break. After lunch however, it was back in the heels! The following Thursday I was just finishing putting away some files in the cabinet and walking back to my desk. It wasn’t five minutes later that a gentleman came into the office wanting to talk with Donna! I managed to slip out of the heels and put my new slip on loafers on and then escort the man in to see Donna! After he left I had to put the heels back on but I was shaken from the incident and complained to Donna about it.
She then said we were taking the next week off! I asked why and she replied “if you are worried about wearing the high heels we can do something about it so you won’t look or feel so out of place. And since you’re getting so good in walking in them it’ll be easy.” She said with another of her smiles and finished by telling me that I would be spending the entire week at her home.
I had an inkling of what was going to happen but not to the degree it happened! I threatened to quit and didn’t really care but Donna was insistent and with an even larger raise being offered I felt almost stuck somehow. The job wasn’t that hard, even in the heels but I knew after I was told the rest of Donna’s plan that I could never pull it off.
The first thing I was to do was pack up and move out of my apartment. I would be living with Donna now and after she was finished with me there would be no way I could really go back to my place anyway. Then the next week passed, and with the fifteen hour days and all the work it passed slowly! But soon it was Monday morning and the start of another work week.
I was terrified to get out of the car when we pulled up to the office but Donna insisted that I could make a go of it and that no one would even notice my changes. I was just the “new” secretary. I was nervous as I opened the car door and felt the click of my high heels as they hit the pavement. I took my purse and after leaving the car I made my way up the sidewalk with Donna. I could feel my new bust jiggling and feel the cool morning air swirling around my nyloned legs! And could hear the swish of my nylons brushing my calves and thighs with each step as I minced along in my tight, satin lined skirt on those five inch heels! I saw a few people moving about and driving past on the street but nobody pointed, or laughed or yelled out. I did notice a few women give me a passing glance as they went about their business and a few men looking me over as we made our way to the office door.
Once inside I was now the “new” secretary and would be known as Deborah. I hung my car coat up, set my purse on my desk then went about my regular duties by making coffee. Donna looked me over.
“Yes, you’re a proper little secretary now, very nice, very ladylike.” Then, issuing a satisfied smile she went into her office.
In being off for a week there was a lot of mail and paperwork to file and catch up on. I finished with the coffee then swished into Donna’s office to deliver her cup. She noticed me mincing on the heels, my shiny nylons swishing under my tight pencil skirt and my bust jiggling under my satin blouse as I set the cup on her desk.
“Thank you Deborah dear” she said as she casually went back to work.
“Yes ma’am” I replied as I returned to my duties.
I sat down at my typewriter and was glad that Donna didn’t have my salon nails made that long. This way they were short enough so I could still type. And I had a lot of correspondence to answer and a lot of typing to do. So I set to work. A couple hours later Donna left for downtown on a couple errands and I decided to stay through lunch to stay safe at the office on my first day totally dressed as a woman, and to get the extra work done.
I took phone calls, answered letters and did my filing as usual then noticed myself in the mirror at the new look Donna had helped to give me. I ran my hands over my feminized form and was astounded! She had dressed me from head to toe and from the skin out! She had gotten me a complete new wardrobe so I would be able to look like the perfect little feminine lady every day around the office. She had corseted my waist, and gotten me a well padded girdle that really widened my hips and rounded my bottom, and I could feel the weight and jiggle from the silicone breast forms that now sat snugly in the cups of my satin brassiere under my lacy, white nylon full slip and my blue, long sleeved satin blouse with high collar and large satin sash bow at the front.
My eyebrows had been plucked into a high and feminine arch now and my ears had been pierced. I could feel the gold hoops as they dangled against my neck from under my long hairdo that was now dyed a bright blonde and fixed in a feminine style that parted in the middle and feathered away from my face in large sweeping curls. I was slightly built and small in stature to begin with but looked nothing like a man anymore and any masculine nuances I had were now hidden by Donna’s intensive week long training session and any left over manly traces were now totally muted, covered up and totally concealed by the ladies clothing, hairstyle, makeup, perfume and jewelry.
The days and weeks passed. And although we had little walk in traffic, no one ever suspected that I was a man. They simply saw the name plate “Deborah” and behind the desk a feminine, shapely lady going about her secretarial duties as the scent of perfume hung in the air and the sound of swishing nylon echoed through the office whenever I moved in my seat or crossed my legs!