Maureen; Surprised By My Boss

Today was to be a special day for me, a day I have been looking forward to for weeks. At work I was scheduled to work on my presentation for the monthly board meeting, so I would be in my office all day alone except for my secretary. Jennifer was super efficient, handling most things that required my input without having to consult me.

With no planned meetings and the likelihood of being in my office all day I could indulge my fantasy, dressing in feminine underwear. Of course all of the feminine frillies would be concealed by my three piece suit. I refrained from doing it very often, never knowing when I might get called into a spur of the moment meeting or have a visitor show up in my office. Most of my fellow colleagues were away at a meeting about sexual discrimination, a class I had already completed several months ago. My immediate boss Glenda, was out touring the different branches, so I felt safe in indulging some of my fondest fantasies.

I loved the feel of feminine lingerie, a bra and panties the most sensual for me. Then there was the stockings and the garter belt, the camisole or slip, lets face it I was a female underwear junkie. It took me over an hour to dress this morning, deciding what to wear and how far to give into my fantasy. I ended up going all the way, even adding breast forms in my bra cups. I preferred a modest size usually a B cup, although I did have a C cup pair for when I was adventuresome. I used adhesive to secure them, knowing my vest and sport coat would hide most of the protrusions on my chest. I slipped a pair of high heels in my briefcase, just in case I found the time to wear them a little today.

Dressed to the nines, I put on a white dress shirt, added my pants and my vest before slipping my suit coat on. We always kept the offices cool, a sure fire way to eliminate any afternoon naps by the employees. That made it perfect for me indulging my fantasy and not sweating to death in the many layers of clothing I chose to wear. Thinking I had everything, I headed to my car and drove the thirty minutes to my office.

Once there I greeted Jennifer, engaged in small talk with her for a few minutes. Then announced my plans for the day. I asked her to not bother me if she could handle the problem herself. She told me not to worry, she would take care of everything, so that I could get my presentation finished. I entered my office, closed the door and signed onto the computer. I checked my emails looking for some change from what I had been told was on the schedule for today. Everything looked okay. So I gathered the things I needed to work on my presentation and then slipped off my sport coat and unbuttoned my vest. The breasts showing some now, the swellings on my chest not usually found on any male.

I proceeded to work on my presentation for over two hours, making quite a bit of progress in completing it. Of course I took many opportunities to stroke my frillies, shifting in my seat often to feel the silk slide over my hairless skin. I slipped my sport coat back on, then made a trip to the bathroom. I entered a stall then had to remove several layers of clothing before I could relieve myself. After finishing and wiping, I pulled up my panties and made sure the garters on the garter belt were snug. I started to pull my pants back up when I felt the tampon I had placed in my pocket this morning. It would complete the fantasy, so throwing caution to the wind, I unwrapped it and gingerly inserted in my anus. Without lubrication if was a little more difficult, but eventually it slipped in. I made sure the string was hanging down then readjusted my panties and pulled the pants back up. It was definitely a turn on for me, my penis trying to poke a hole in my panties, even though I had him tucked back between my legs. I had to wait a few minutes for things to return to normal, then returned to my office.

I kind of ignored who was in the hall as I headed back, anxious to get back to the safety of my office. It seemed busier than normal, although no one said anything to me. Jennifer told me she was stepping out to get lunch, did I want her to get anything for me. I declined and she left the office. I hurried inside, opened my briefcase and removed my heels. I shed my shoes and my socks, leaving the stockings showing a little. I slipped on the heels, then walked around the office to savor the feelings.

I was headed back to my desk when the office door opened and my boss Glenda poked her head in. I panicked and quickly headed to my desk. Well Glenda was already nearby and grabbed my wrist pulling me out into the hall. She was muttering something about why I had waited so long to complete my physical.

I don’t think she had noticed my heels until the sound of them on the tile floor of the hall made it obvious that one of us was wearing heels. Since she wasn’t wearing heels today it became obvious who was. She smiled, but kept heading in the direction of our company doctor. I tried to put on the brakes, but in the heels I had little success of stopping her from dragging me into the doctor’s office. Once there she let the nurse know I was here for my company physical, apparently the last one needed to complete the company physicals for the year. She entered the examination room with me telling me she wanted to see what other surprises I might have underneath my suit. I resigned myself to being found out as I started slowly undressing, but Glenda was impatient and soon had me down to my female underwear, my male clothes folded neatly in a chair by the door. The doctor and nurse chose that time to enter, the lady doctor the first one to notice my choice of clothing, then looked at the file she had in her hand.

She asked if I had a name I preferred. You don’t look much like a Martin in those clothes. I was focused on the floor, hoping it would open up and swallow me. Glenda raised my chin and told the doctor to put down Maureen, until I decide on a name for myself. Glenda went over to another chair in the examination room and made herself comfortable. I gave her a stern look, but she just giggled. “I would not miss this physical for a million dollars. So let’s get on with it.”

The doctor examined me, then when it was time for her to check my prostrate she stuck her hand down there and played with the string hanging out of my body. She told the nurse to get her the female physical form, since the one in the file is obviously the wrong one. Giggling a little as she had to repeat her request to the nurse twice. I was helped up onto the examination table and my feet were placed in stirrups, a single strap to each ensuring they stayed there. The stirrups were spread wide and the panel underneath my butt was lowered, leaving me exposed from the waist down. Of course, I was redder then red, doubting if the humiliation could get any worse. Well she removed the tampon, with a plop then inserted a speculum into my anus and opened it up exposing my insides. She shook her head in disgust, mumbling something about females these days telling the nurse she needed a certain type of douche. The nurse went to retrieve it as Glenda was about to split a gut.

The next twenty minutes seemed like an eternity as she poked and examined my insides carefully. Then she placed a large bowl under my butt on a smaller shelf slightly below where I was laying. The nurse returned with the douche, the size of the bag that was attached to the nozzle scaring me to death. The speculum was removed, as I let out quite a sigh, glad to have the thing finally out of my ass.

While the nurse was getting ready to administer the douche, the doctor was removing my bra and manipulating the breast forms. Too much going on so I zoned out only to come back to the here and now suddenly as something quite large was inserted in my anus, then the warm fluid flooded my insides. It kept invading me, much more than I thought I could handle. After the bag was empty I felt like I was going to spew liquid out of my ass, my mouth and nose, the feeling of that much liquid in me overcoming all of my normal tolerances. All of the liquid that had been forced into me finally left me by my anus, the room now smelling like flowers, the scent of the douche quite overpowering.

The doctor would make notes in my new file, then go to the next item on the list. It was over an hour later when the physical was finally over, The doctor asking to talk to Glenda for a few moments privately. They stepped out of the room as the nurse finished cleaning me up down below. The nurse complimented me on my stockings, wondering where I got them, she might give them a try herself, much sexier than pantyhose. She was sure her hubby would enjoy the look and feel of her in stockings. She did ask if I had a boyfriend, but I never did give her an answer to that question.

When the doctor reentered she told me they were going to sedate me for a while, something she noticed in her examination needed correcting. Nothing invasive, just a minor correction that would make me feel much better about myself. I was still out of it some so I just nodded my head in agreement. A few minutes later I was given a shot, and was sound asleep a few minutes after that.

When I awoke things seemed much different somehow. I laid there trying to focus on anything and get some of the fuzziness to clear out of my mind. Finally a few thoughts found there way to my conscious mind and I looked down at my body to see what was different. I was still in my female lingerie, my breasts seemed a little bigger but maybe it is just my eyesight not focusing properly yet. The nurse was there to unstrap my feet from the stirrups and help me sit up. I noticed something swing against my neck, reached a hand up there to see what it was, finding I now was wearing earrings, the pierced type not clip on like I usually wore.

Then with my eyes finally focusing some I noticed that the front of my panties was smooth, I immediately reached my hand down there to slip under the panties to see if junior was still there. I let out a loud groan, nothing but a slit, moist and warm was there. I previously had a penis in that space, but he had vanished. I looked at the nurse, and she smiled, then suggested that I check out my breasts. I eased my hand up to my bra and grabbed a hold of the breast form through the fabric of the bra. Surprise, surprise I could feel my hand touching my breast, something that has never happened before. I promptly fainted, too much for my feeble mind to process, much less handle.

A mirror was placed in front of me as my eyes opened again, the nurse having used a wet cloth to bring me around. A startled look at the image there, cleared my mind right away. No longer a male in female underwear, now an honest to goodness female that seemed attractive and well endowed. That was the image displayed in the mirror, blinking my eyes several times did not change that image. My face was still male looking, but everything from the neck down was looking very much like a female.

I had a million questions but I could not verbalize anything. Glenda returned to the examination room with some papers in her hands. “We have straightened out the mistake made when you were hired, now your records have been changed to female. You will need to use the female restroom in the future, and fraternization with male members of the staff are frowned on while at work I have included a dress code for the female employee, and have arranged suitable clothing for your return to your office. I suggest you spend the afternoon purchasing proper attire for your job, since I will be sending out a memo this afternoon company wide, clarifying the mistake that had been made and the resulting change in your name and appearance.

I looked at the chair my male clothing had been placed on noticing that only a dress was there now. Something to cover up my feminine image is better than nothing. I swallowed hard, reached for the dress and stepped into it, Glenda helped me with the zipper and I was pushed out of the doctor’s office. I quickly made my way back to my office, hoping no one would recognize me dressed as a female. I was still in the heels and someone had released my ponytail and brushed out my hair. The one pair of earrings that were drop earrings swaying to and fro on my neck, keeping me off balance and disoriented as I teetered along in my heels.

Back in my office Jennifer poked her head in the door, asking me if I wanted her to make an emergency appointment at the Turnabout Gurl salon in town. How she knew about the salon baffled me. Another sigh, I guess I have not been as stealth in experiencing my fantasy as I thought. I nodded my head, and she returned to her desk to make the call. A few minutes later she reappeared, telling me they would squeeze me in as soon as I could get there.

I gathered my things placing them in my briefcase and heading to my car. Jennifer gave me a hug as I passed her desk, telling me I like you much better as Maureen, Martin was so uptight at times. Blushing many shades of red I thanked her and hurried out of the offices, anxious to get to the safety of my car. Once in the car, I just sat there for several minutes trying to piece together what had happened. No conclusion other than it was seemingly one disaster after another this morning. I did check my breasts again as my hand slipped up under my dress to see if they were real. I pinched my nipple through the fabric of the bra and almost lost it, the sensual feelings swamping my overworked mind.

I did eventually make it to the salon, once I checked in I was taken to a treatment room and undressed so they could see what might need to be done to make the transformation complete. With all the clothes removed, my female sex looked quite authentic, even including the tell tale sign of a tampon string handing from my new vagina. I then focused on my breasts, trying to see some seams where they were attached to my chest. Absolutely nothing there, they were apparently a part of me.

The gal that manages the salon entered the room, asking me if I liked the new feminine equipment. I gave her a puzzled look, as she smiled telling me that several of her technicians had performed the work on me at my office. The vagina is fully functional, junior glued back out of the way for the near future. The breasts are our newest breast form, glued to your chest after all of your body hair was removed permanently. They are there from now on, a D cup size if you are interested. They bond with your skin so there will be no seams, transmitting touch to the nipple underneath. They never have to be removed for cleaning allowing the skin underneath to breathe naturally. They can be removed later after a year, but not before that time. Your earrings are lasered in, the holes never closing up, three holes in each ear for your selection of earrings.

Now I presume you want us to finish the transformation, hair, makeup, and of course a suitable wardrobe for an executive with your company. Oh, we can’t forget some long fingernails, the ultimate finishing touch to your new persona. I promptly fainted again, a few words still plodding their way through my mind, vagina full functional, breasts real and D cup in size, not removable for a year. In the mean time they had started working on me, washing and conditioning my hair. A received a suitable feminine haircut and then the rest was placed in curlers. Way too many in my opinion. My nails were worked on as my hair was being dried, extensions and a bright peach polish to make them shine, the end result. Makeup followed, then the curlers were removed and the style brushed out.

Several carts were pushed into the room, containing my new wardrobe, each piece to be tried on to make sure it fit properly. Most everything fit, so after donning one of my business suits, the rest of my things were bagged up and taken to my car. I was advised to hang them tonight in my closet so they would not wrinkle, then place my new silky bras and panties in a drawer. That also applied to the garter belts and stockings. The bill was rung up and I had to pay half of it, the company picking up the other half. My half was over two thousand dollars, about thirty bags and garment bags worth.

As I made my way to my car I was still in a daze. Fully feminized, a complete female wardrobe and apparently working as a female in the future. Quite a lot to get my thoughts around. I did make my way home, having to make ten trips to get all the clothes inside. Then to get room to hang my new clothes I had to take almost all of my male clothes out, placing them in the bags that I had just emptied. Three hours later I had hung all of my new clothes, all of my male clothes already in bags to be done something with.

I decided I needed a more through look at my female figure, undressing down to my panties. I was reluctant to take them off, not really wishing to look at the pussy that was now where my penis used to be. Then, of course, my body decided I needed to pee now, so another new experience as I sat on the toilet after sliding down my panties and removing the tampon that had been inserted at the salon. It took me a while to get focused enough to let it out, the resulting spray that got me and the toilet wet having to be cleaned up now. I presume I will need to buy more toilet paper now, if what I used just now is any indication. With that experience burned into my mind I finally made it to the mirror to get a closer look at what had been done to me. The breast were almost perfect, at least to a former male they were. Perk nipples and hardly any sag to them as I cupped one with my one hand, instantly feeling the touch of my hand. My nipple hardened some and a pleasant feeling spread through the rest of the breast. Gawd how I am going to handle all of these sensations?

As I looked into the mirror my fairly small hips seemed wider and bigger, the small amount of hair that used to reside there now gone, according to one of the techs permanently. My eyes finally ended up focusing on my eyebrows, or I should say the lack of any eyebrows. Nothing there anymore other than the penciled arch that had been applied to the space above my eyes.

I went to the kitchen and made me some tea, something toi take my mind off of my appearance and changes to my body. I dressed in a nightie, crawled under the covers and a short while later managed to get to sleep. Thankfully I did not dream or if I did I do not remember any of what I dreamed about. Thank goodness for small favors.

I dressed in some of my new clothes, then did my makeup and hair. The hair style was easy to brush back into place, the makeup job not near as good as the salon but hopefully adequate for today. I slipped my stockinged feet into a pair of heels and I was ready to head to work. I said a silent prayer as I drove the distance, hoping today would be manageable, so many things that could go wrong and apparently not within my ability to control anymore.

Jennifer smiled at me as I entered my office, laying a couple of emails on my desk. Yep, I was now official, Glenda announcing that I was now presenting as female, any comments or kidding will result in your immediate termination. She was never much for long winded speeches in any meetings she conducted. Since my gender has been changed on the company records, this is not for the short term but for as long as I work here.

Hey, at least I get to wear my silky underwear any time I want. A minor benefit considering all the other things that go along with being female. No complaints though, I will take it as it comes after being surprised my my boss.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

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