Penny; A Difficult Choice

The rumors were rampant, ever since the company was bought out two months ago speculation has been absurd. The new owners were evaluating everything, its productiveness, and if it fit into their new grand plan for the future. I had a particular bad feeling about today, but decided that staying away from work for a day might be worse than showing up. By lunch, I pretty much knew my time employed was coming to an end. Five of my colleagues in the same department have already been let go, cleaning out their desks, and being escorted off the property. Since I did not get a chance to talk with them, I have no idea what they were told for the reason they were being let go.

Then I saw Nora’s secretary headed towards my cubicle, any doubt about my termination now gone. Sure enough she escorted me to Nora’s office, then closed the door as she left. Nora had me sit in front of her desk, while I tried to throttle my emotions and at the same time be brave. The being brave part was not working, a few tears were forming, but had not made their presence known yet.

Nora and I have been friends since college, in fact she was the reason I got this job here some five years ago. She is my immediate boss, a position she has held for the last two years. She was always the driven one, doing extra while cleaning up the messes that others created. It apparently worked for her, her position in the company quite secure. There was even talk about her being promoted to the CEO position soon, the existing CEO being transferred to another company, the owners being the same for both companies.

As I tried to get comfortable in the chair, she wanted me to listen very carefully to what she had to say. “There is a favorable way out of this for you, but it would be very costly, especially to your male ego. The rumors about the company closing part of their operation are true. Your division no longer exists, and you’re the last employee to be notified of that decision. You will get four weeks’ severance pay, but your medical benefits and any other benefits end as of this conversation. I will supply you with a letter of recommendation if you wish. Of course, if asked I will give you a good reference.”

I could feel the tears now dripping down the side of my face, for being a male I was far from unemotional. I could see big changes in my life, a lot of what I had accumulated, I will no longer be financially able to keep. The apartment will have to go, way too much rent for someone unemployed. I had no grand ideas about getting a job anyways soon, the job market was still almost non-existent, and a whole division of employees now similarly without jobs would only make matters worse. Then there was my car, at the time I was so happy to get a deal on this sporty model, now it seemed like another foolish blunder on my part. Add in the fact that I am renting furniture, that I eat out at least four times a week and it points to a very dismal future for me. All of that will have to end and soon, or I will be out on the streets in less than a month.

Nora was staring at me, with a small smile asking if I was back to the present with her. I blushed red, but nodded my head that I was again listening. “I have a way out for you, another job here, but quite different than what you have been doing. It will be working for me, I am aware of your abilities, and feel you will fit right in. There is always a catch, and this job has a big one. This job is available for you, but you will not like what you have to do to get and keep it. Listen very carefully to me, this is the part that will be hard to swallow.”

“The job is available only to Penny.”

Oh shit, I had no idea it was this bad, Penny was my name when I appeared in a college play that ran for almost fourteen weeks, a new school record. I played a ditzy blonde female, more enamored in what clothes I wore than in my work or love affairs. Don’t ask how I got the role, I still have no idea how me showing up for auditions and reading for the male lead got me the leading lady role. I soon dressed the role 24/7 since adding the prosthetics and doing my hair and makeup was taking so much time. It was alright, I guess, I got an A in the drama class because of it, and kidded about it for the remainder of my college years. My character name stuck, even at graduation I was referred to as Penny by all of my fellow students.

Now to keep my job here I will have to live the role again. More than a few tears did slide down the side of my face, Nora interrupted my meltdown asking me to empty my desk, then I am coming home with her, and we will talk some more.

Her secretary came in, grabbed my hand and we went back to my office. She furnished a box for me, and watched as I packed it. My vision was clouded with tears, I am really not sure what actually got put in the box. I had very few personal things here at work, my interaction with anybody almost non-existent. Maybe a hello when I came in but that was it. In my division most everybody kept to themselves, a few females having lunch together every once in a while.

Then I was taken back to Nora’s office. I tried to get loose from her secretary, I just wanted to be alone and wallow in my own little pity party, but she would have nothing to do with that. I was left in Nora’s office, just about ready to break into a huge sobbing mess. Nora finished a phone call then grabbed me and walked me out to her car, holding the passenger door for me until I got in. I presume she was not taking any chances on me running off before she got me to her home.

The ride was in silence, while I was trying to figure what I was going to do, nothing making any sense, everything I thought up seemed so ridiculous and inadequate. I was totally out of it, only becoming aware of where I was at when she parked her car in her garage. I tried to resist, just wanting her to take me home so I could be depressed by myself. Instead, I found myself sitting on her guest bedroom bed a few minutes later, as she went to get me something to drink.

I just sat there, I should get up and leave, but I had no idea of what to do or how to accomplish any of it. My car was still at work, so getting back to my apartment meant a cab or getting Nora to take me. Since she was the one to kidnap me in the first place I was stuck here with her.

She was back with some hot chocolate, a favorite of mine that we used to share a lot of in college. She always made it so good, way better than I could ever manage. We sipped on the chocolate, then she took my empty cup and set it on the nightstand and pushed my head back onto the pillow. She kept her hand on my chest to prevent me from sitting up again and soon I was lost to the world.

I woke up later, the room dark, apparently it was sometime after dark. I got up and used her bathroom, then made my way to the kitchen. I had been to her house before while in college, her parents now living in southern Florida, leaving the house to her. I opened the refrigerator looking for something to nibble on, found some eggs and made us an omelet, about the only thing I could cook and still live past eating it. No meat but lots of vegetables, some hot sauce and lots of cheese.

As I was turning it over for the last time Nora showed up a huge smile on her face. She got us two plates and some forks and we sat there and annihilated the omelet in less than fifteen minutes. I cleaned up, washing the dishes and pan, putting them away where they belonged. Nora sat and watched me giving me a clue every once in a while to finding the right cabinet. I wiped down the counters and she dragged me to her living room. I did notice that it was six AM as we walked by her grandfather clock.

I sat on the sofa, with her squeezing in right next to me, leaving the majority of the sofa empty. She has never been shy or unable to find words to state her point, today was no exception. “I have made an appointment for you to be converted to your Penny persona later today. I want you to try it for a month, no excuses, just go along with this and do the best that you can with the job. After the month we will talk again, and then decide whether you will continue. I know it is out of your comfort zone, but I need you and your skills. After a shower, I want you to change into the clothes laying on the vanity chair, then return here within an hour. Your appointment is at ten this morning and you will not miss it. Am I clear on this?”

I leaned closer to her, hugged her and thanked her for the confidence and trust in me. I got up and was swatted on the butt to get me moving faster. As I walked back to the guest bedroom, I am not sure why I didn’t fight her on this, her plan for me is so out there, but I have always followed her lead, I guess I am too well trained to stop now. Okay, the real reason is that I have no idea how to handle this on my own. Every scenario I come up with ends up in disaster for me, imminent disaster as I look at it now.

I got the shower, then looked at the clothes on the chair, what I suspected was there, a complete female set of clothes, at least I got a pair of pants instead of a skirt or dress. The pants were so soft, as they slid up my legs the goose bumps popping up everywhere. I made it back to her in time and I was whisked away to the salon. I tried to get her to let me pick up my car at the company parking lot, but she nixed that idea right away. No car no escape from my scheduled ordeal. To me it was going to be an ordeal, playing a female character in a play is vastly different to living as a female 24/7. Once she pulled up to the front of the salon I knew it would be much worse than that.

The place was huge, dripping of all things female. I know a couple of hours in there and there would be no masculine features left on me. Nora got me as far as reception then another lady came and collected me. I was dragged off to a private room in the back, my eyes darting back and forth at all the sights on my way there. I saw a lot of males there, in all stages of being feminized. If what I saw was representative of what they can do they are indeed good at their craft and I am now doomed.

As the door closed to the room I was led to, I swallowed hard, time for me to give in and give this a try, I seem to not have many options left, at least ones that I might want to explore. Maybe doing this is the right way, no time like the present to give it a try. My stomach was tied in knots, my nerves were shot and the tears were forming again, in preparation for another sobbing episode. I took a big breath and counted up to a hundred, trying to calm down and regain my composure. Well at least some of my composure, the ordeal facing me did leave me nervous and very uncomfortable.

How can you look forward to be converted to the female sex, something I have no exposure to except for the role in the college play? I did dress 24/7 for the play, but that was on a college campus where a lot of things were taken for granted without much fuss. This is about living and working as a female in regular society and interacting with that same society as one. Two different worlds in my opinion.

Methodically my masculinity was eliminated, my body hair being the first causality. It was waxed off, the suddenness and the pain kept me from thinking clearly. I was vocal for sure, but no one was listening to my utterances. Then two humongous breast forms were glued to my chest, while I was trying to figure out how I was going to cope with them junior was hid under a false vagina. As I looked at my image, what little resistance I had melted away. It was too late, Penny’s image was already partially there.

Over the next few hours her image was enhanced until there was no male me left. I stood in the front of the salon, my hair curled and highlighted, my makeup impeccable and my nails lengthened and in a delightful peach color. I was wearing a ladies business suit, a tight skirt and a blazer over a very feminine blouse. I was hoping for someone to take me back to Nora’s or better yet to my apartment. Well my karma must have been pretty bad since Nora showed up and promptly took me back to work. I was taken by her to her office, my attempts to do otherwise quickly quenched. I was shown to her secretary’s desk and told to make myself comfortable.

My eyes pleaded with her, all of this too much and too fast. She showed me a report she wanted proofed and typed up, helped me to log in to the computer system, then retired to her office. Several big sighs and I figured I better get started on the report. Why I gave in so easy, instead of walking out I have no idea. I did know the breasts and the vagina were affecting me, I somehow couldn’t picture myself a male anymore, now feeling rather submissive and docile, my previous extremely limited assertiveness now a thing of the past.

Then if I did walk out, how would I support myself. Getting rid of the car, the apartment and finding somewhere cheaper all seemed to be insurmountable tasks. I kept running every scenario I could think of through my mind, trying desperately to avoid what I was sure was coming.

Since my mind was not functioning the way it should it took me almost three hours to redo the report. The wasted time was consumed thinking of how I was dressed and trying to figure a way out of this new situation I found myself in. I handed Nora the report, then started back to my desk. Nora stopped me having me stand there as she reviewed what I had done. The smile said it all, I was exactly what she wanted in a secretary, although she would like me to concentrate on my work and not on my appearance a little more. I was given more things to do, so I wandered back to my desk, after getting something to drink from the break room. I passed several females that I had met before the change in me, I was greeted warmly, with no mention of my looks or new job. I managed to finish all the work she had given me, by quitting time, then gathered my things trying to think how I was going to get home.

When Nora had brought me to work I did not see my car in the parking lot, but was too afraid to ask where it might have ended up at. Nora came out of her office, grabbed my hand and we made our way to her car. I managed to ask about my car a few minutes later, but was shocked when she told me she had it towed off. Most likely where you had it financed will have repossessed it by now, so you need not worry your pretty little head about such trivial things.

“Oh, I have had your male things donated to charity, and ended your lease on the apartment. With what you now make it was really too expensive for you. For the time being you are staying with me, so get used to it.” I looked at her, wondering if she was serious or if she was pulling my leg. Oh gawd she is serious, my whole life turned upside down in the span of a couple of hours.

“Now do you have any more concerns, I don’t want any more worry lines to show up on your cute adorable face.” With that last remark I turned down the visor and looked at my face in the mirror, trying to see if there were worry lines on my face. Nora just giggled away for the remainder of the trip. When we got to her place I was drafted to help make dinner, some salads and assorted fruit the fare for tonight. I have to admit it wasn’t what I was expecting, actually quite delicious and satisfying.

We talked a little bit about my day, it was nice and I realized for the first time I was relaxed and able to talk about things without breaking into a sobbing fit.

The thirty day trial over Nora decided that I would be her P.A permanently, I was told of her decision and I nodded my head. I was doing better as her secretary/PA, handling things quickly and with little stress. I even was interacting with my fellow PA’s, something I had never even attempted in my masculine persona.

Nora decided she needed to buy a house, she did get the promotion to CEO and of course I went along as her PA. We looked for weeks for the right place, eventually finding it in a gated community not far from work. Although I can drive again since a proper driver’s license was obtained for me, most of the time I go in with Nora. When she travels for the company I usually accompany her, so we are seldom apart. Due to her focus on my past all of my male debt was cleared up, and anything not essential was done away with. That specifically pertained to my male clothes. According to Nora I will never wear another piece of male clothing in my life.

Away from work I have assumed the housewife duties, cooking and maintaining our home. Since she is the CEO we have frequent parties at the house for the management tier, where I serve as the hostess for these affairs. I am sure there are quite a few rumors circulating about the two of us, but nobody has made any of them public. Since the company is doing so well under her leadership, any attempt to discredit her would be foolish.

Away from work I am her lover, the amount of time she spends on pleasing me is unreal. I try to return the attention, but her happiness and orgasms come from spoiling me rotten, something she does with ease. It was about a year later from when Penny first made an appearance that Nora and I took a short vacation. It was sudden as I was getting ready to go to work, a bikini was thrown in my face. I stared at the item, then at Nora. She giggled, told me to pack it in my suitcase along with some other warm weather clothing and be ready in half an hour. She ended up having to help me as I was suddenly in panic mode. What do I take, where are we going and what about work? None of my questions were answered, she got some things in my suitcase then closed it up. I was dragged to the front door, a cab there to take us to the airport. Three hours later we were checked in to a villa in Cancun. I got to wear the bikini once, all the rest of the time I was flat on my back being ravaged by my boss and lover. Why we had to travel all the distance for me to never see much of the area will remain a mystery.

We did make a stop on the way back at Las Vegas, I was proposed to, married and the marriage consummated all within a short time span. On the way to the airport I slid a quarter into one of the one armed bandits and won five hundred dollars. All in all a very successful trip. As we were flying home I looked at the rings on my fingers, a wedding band and a gorgeous engagement ring fit for a princess.

Once back home I was booked into the salon for a full makeover, something that would take a week to complete. When it was completed there was never any doubt as to my gender. The breast forms were removed and replaced with ones that were sucked from my body. Junior was hid under a very realistic vagina, Nora preferring to show her love for me with a dildo, in either of my two orifices. For the first couple of weeks after I returned home my breasts were the preferred play toy, my nipples so sore and swollen from her efforts. When she finally moved further down I let out a huge sigh of relief. She still paid them a lot of attention but I could handle her mouth on them so much better than when she manipulated them with her hands.

That wasn’t the only changes, however, as my hair was lengthened, my eyebrows eliminated, my lips plumped and numerous other cosmetic enhancements. A new wardrobe, this one more casual, perfect for a wife to an executive. I still helped on occasions at work, especially if there was something important to complete. On business trips I still accompany her, her regular secretary not near as experienced as myself.

All of this resulted from a choice so many months ago, a difficult choice that I accepted after a lot of pushing and shoving from a certain individual. A choice that I am so happy with and a spouse that I am so in love with.

Story Complete For Now

© 2016 thru 2021 Fran Cesca Walker

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