Adwomen
A Short Story
By Maryanne Peters

Siobhan and I had gone through a similar education for a career in advertising. We shared a modest apartment in the city. We were both young and ambitious, and short of money. The only real differences were that she was a woman, and I wasn’t; and I had talent, and she didn’t.

So, imagine my private disgust when she got a prime job at the Garret Agency, and I was still only free-lancing. She got the job because she was what I was not. The Garret Agency only hired women.

Penelope Garret had been a high-ranking executive in one of the world largest advertising firms, but could not get advancement. She bemoaned that the industry was dominated by men, so she left her job to set up her own business, offering new approaches in marketing and promotion. The Garret Agency was highly successful.

Siobhan was only able to keep her position because of the work I did for her behind the scenes. We negotiated a deal and I received some of her salary package in return for doing a lot of her concept work, including scripting some of her presentations.

But it could not last forever, and when she was offered the opportunity to lead a team (based largely on the quality of the work I had done) she knew that she could not continue as she had done. She could not take the work home and have me do it for her. She needed to perform on the job. The problem with leading a team is that they look to the team leader for inspiration and she had none. She would be found out and she would be put out. Simple as that.

She was given two trainees from the staff but given the opportunity to recruit one person from outside to be on a level above those trainees. That is what led to her extraordinary idea. An idea that would change my life forever.

It was obvious that I should be that additional member of the team, but it was not possible. But Siobhan had the solution. I needed to go from being Eddie Boyd to Emma Boyd. And it needed to happen fast.

When she put the proposal to me I just laughed. I told her: “That is the single craziest thing I have heard in a lifetime.”

“Look at yourself Eddie,” she said. “You are not a big guy. Get rid of that thing you call a beard and tidy up that hair and would not look half bad as a girl. In fact, with those cheekbones and big green eyes, you would make a better-looking girl than a guy.”

I had let myself go a little working from home and not mixing with anybody other than her. The truth was that I lost a lot of confidence in myself. The only thing that I was good at was the work, and I put effort into that. I had lost weight, was pale from lack of sun, my hair was long and I had not shaved in six months – not that much growth had resulted.

“Let’s try a makeover,” she said excitedly. “If I can convince you that you could get away with it, then you have to consider it. And even if you slip up, we could say that you are a transwoman. I can’t see Penny Garret firing you if you are trying to be a woman.”

That last comment got me to thinking that it might just work. I said: “Maybe I could just take the job as a transperson? Like, just half a woman?”

“No,” she said. “That’s our back up position. I tell you, I think you could pass as a girl. You just need to follow my instructions. Now let’s go to work on that face. Starting with a shave …”.

That is what she did. She just gave me a makeover from the neck up. I shaved closely and she washed and styled my hair. When I looked at myself in the mirror I realized that she was right. Provided I said nothing and did not move, I could pass for a woman. In fact, I was quite pretty.

The possibility started to appear real, so I opened negotiations. I said: “To do this I still want a share of your salary on top of anything I earn. In fact, I want the package you are getting, with the difference out of your pocket.”

She was pissed. But she had to bite her lip. “Ok,” she said. “But you are a prick”. She was smiling as she said it, but she meant it. The hell with her. If I was going to go through with this it needed to be worthwhile. Without me she would not have the job. With me onboard we could go places.

We had some time to get me ready, and we needed it. It was not my appearance that was the problem, it was as I said – if I said nothing and did not move I was Ok. I did not carry myself as a woman. It was that way I walked and moved my hands. It was all wrong. I needed to be instructed by Siobhan and to watch women more closely to understand the differences. Fortunately, observation and imitation fitted with my artistic bent, and I picked things up fairly quickly.

When it came to my voice, Siobhan suggested that I keep talking to a minimum. Essentially, she was suggesting that I should whisper with her and let her do the talking. I could see where this was headed so I did my own work on this. I found voice coaching for transwomen on the internet and worked diligently to get it right, but I did not discuss it with Siobhan.

My facial stubble returned a little so we both realized that I would need more radical work to stop me developing a five o’clock shadow around five o’clock. That, and the full body wax was the hardest thing about “my transition”. But when the inflammation had subsided and the moisturizers had done their thing, I found that I quite liked the smooth skin. My hairless body was sensitive, but then there were the silky undergarments. It really did feel nice.

Then Siobhan appeared with a syringe and a bottle of pills.

“Oh no,” I said. “If that is what I think it is then that is going way too far.”

“Look,” she began, “You have to face reality. This isn’t forever, for either of us. But while you are pretending you need to get it right. These pills will stop any beard coming back and will soften your skin and improve your hair. And they will prevent erections. In an office full of women a tent in your dress would not be a good look.”

“And what about the syringe? I asked.

“Yes,” she replied, “They are more of the same, but I am suggesting monthly shots to coincide with a monthly cycle. You will not understand this Eddie, but you will be in a woman only environment. This is essential.”

I didn’t understand, but I went along with it. I am not sure why. I remember thinking as I felt the cool fluid entering my system: ‘where will all this lead me?’. Anyway, it was the last time she ever called me “Eddie”.

When the day came I washed my hair and Siobhan styled it a little. I applied my own makeup as she had taught me. I needed to be confident in my new skills. She had picked out a skirt and blouse for me. The overall look was ‘low-key’. I was to appear uninteresting. That was not my personality, but I could see why – a person in disguise does not want to draw attention to herself.

It suited Siobhan too. She was still the alpha female, or she wanted to be. I was to be the quiet and invisible toiler. Her problem was that even in this outfit, with awkward makeup and manner, and not even being female, I was actually prettier than her. I think she knew it too.

Meeting with Penelope Garret was like 30 seconds in a tornado. She shook my hand, looked me up and down, asked two particularly astute questions, announced her approval and moved on, surrounded by attendants. I was impressed. It made me wonder how Siobhan had been able to hang in here for this long.

The answer was, that at the lower level, there was not the same level of competence. In no time, I was standing out. And I could talk too. Much to Siobahn’s surprise and perhaps disgust, my practised feminine voice sang out confidently.

Almost immediately I ditched her look for me. With my first paycheck, supplemented by a chunk of hers, I went shopping. I suppose my eye for a theme enabled me to develop my own style and colour palette. The same with the makeup and the hair. It was just long enough to wear up, which could be both feminine and practical, and allowed the use of some colour or decoration. I was really enjoying these other creative outlets.

For an artistic person like myself, who believes that an image should tell a story, I understand the advantage that women have over me in their daily appearance. As a man you cannot do this. Even if you do just a little, it is not the risk of being called “a fag” that is the problem, it is the risk of not being taken seriously. My look said colorful, confident, individualistic, practical, and serious about the business that I was in: Advertising.

Penelope liked the look. She sat in on one of my presentations, and she liked my delivery too.

It was becoming clear to Siobhan that I was a threat, but she knew her limitations. So, when I was appointed as a team leader instead of her, she told Penny that she would like to stay on my team. She had to take a pay cut, but she actually made on the deal because I no longer insisted on a share of her salary.

It was all going really well, and I was not giving much thought to anything other than work. I spent long hours at the office, even after Siobhan had gone home. When I was at home I still did some freelance, although I was not taking on any new stuff. And the pills had kept any thought of sex out of my mind. Not that I could have pulled any women looking as I did.

But it was the day when I first noticed my breasts that I was forced to address my situation. It had been a hot Friday and I was having a shower after work. I was using a nice floral body wash but as my hands passed over them I realized that not only were my nipples sensitive but I had two fleshy mounds behind them. Big fleshy mounds. It seemed incredible that I had not noticed them before. Showering in the morning was always a rush, but it seemed crazy that I could have missed them.

Siobhan had been out but when she came home she found me sitting in my robe crying. I seemed to do that sometimes lately, but now I had a reason.

“Look what your injections have done to me,” I wailed at her. “These aren’t going away. I’ll need surgery to get rid of them.”

“Just not yet,” she said smiling at my new assets approvingly. “It’s still early. Let’s go out and show those girls off.”

I could not believe what she was saying. I thought that she was my friend. Sure, I had overtaken her at the agency, but we still shared an apartment and worked together. But her idea was that any problem could be solved with a night on the town and a few too many cocktails.

Her contribution was a push up bra and little black dress. Somehow when I put them on I brightened a little. The bra did its job and with the assistance of some well pleased gel inserts, from the next down I looked like a porn star. For my face and hair, I played around until I had something I liked. Then Siobhan changed and we went out.

I had the occasional drink after work, but I had never gone out like this. It only occurred to me when we were in a bar that it was almost a first being among men. I say that because every day I commuted among men, sometimes lunched where men were, and I had even met male clients, but this was different. I could feel and sometimes glimpse men watching me. Watching me approvingly.

The funny things is that Siobhan was right. It did make me feel good. Not the drink, it was being surrounded by people having fun. And I almost felt that I was the cause of some of it. People (men that is) wanted to be around me and talk to me. I was chatty but a little coy. You have to be when you have a secret in your panties – even just a little one. It seemed as if there was a year of smiles and laughter around me, in just that one evening. I forgot all about my growing problems.

I must have been propositioned at least 10 times. I mean propositioned as in “let’s go somewhere quiet”, or “I’d love to meet up with you again”, or “here’s my number – call me”. I found 4 different business cards in my handbag when I got home. Siobhan had one!

I did not go into the office on Saturday morning. Instead I went shopping with Siobhan and bought some evening clothes. We went out Saturday night to – somewhere completely different. Siobhan and I latched on to a couple of bond traders, and they took us for a late night supper.

“I would jump this guy in a flash,” she said as we were both in the Ladies Restroom. “But I know you can’t, so it would be too complicated.”

For a moment I had a pang of regret that I was unable to “jump” my one of the two. He was handsome and rich, but a really nice guy to. If I was a real girl I would have been happy to have sex with him. Afterwards the idea that I could have that thought made me shudder. I had never had a gay thought in my life as a man. Now I was sad that I could not have sex with a man?

I did go into the office on Sunday to work on a campaign, and while I was there Penny popped her head into my workspace. For some reason I was wearing a floral dress over my push up, instead standard Sunday sweats. She remarked how good I looked.

“I think that you should come with me to a dinner on Wednesday night,” she said. “It is a potential new client, and a big one. All men, but they want us to help them break into the female market. Let me tell you, we girls have got to use all our assets to win the business, and you have assets.”

Siobhan was almost beyond being envious when I told her. But she just said: “Win and the client and make sure our team has point on the project. We need to pick up the annual bonus next month.”

It occurred to me that with all that had happened, Siobhan might have every reason to be burning up with jealousy. I was better at my job and more attractive to me, and it was all a lie. But she appeared to be driven by practicality, as if she knew her shortcomings but knew that we could do well as a team. That was the way it appeared.

There would be eight of us at the dinner. Penny and I, and another partner in the firm, Grace, on our side; on their side the Chairman of the client and his wife, and 2 male executives and one female executive. Penny suggested that she, Grace and I all go to the salon together after work to get ready, and we talked about what we would be wearing.

We also talked strategy. Grace was strong on the numbers, Penny was broad strategy, and if the opportunity presented I was to be creative - float some specific ideas. We spent the whole day preparing, but I knew that I could not develop effective ideas until I understood the client’s intentions.

The salon was a new experience but I loved it. Penny persuaded me to lighten my hair, and to add some curls. She even added some curls to her own hair which was usually straight and quite severe. We had manicure and pedicures for our open toe shoes. There were also facials and a little eyebrow shaping. Then makeup applied by a professional beautician.

In that environment I found myself talking with Penny almost as an equal. I think that by the time we were out of there I had a much better understanding of her personality and her ambitions. My admiration for her only increased. She was a total professional but imaginative and creative – a perfect advertising person.

I chose my dress. It was asymmetrical and a little weird, but it spoke of my style and the colors were perfect. And there were my breasts on display. I understood now what role they had. They looked round and ripe. I felt really good. It seemed strange to me just how different it was being a woman. Sometimes just looking at yourself in the mirror could be uplifting. I don’t think that I ever had that feeling as a man.

At dinner I found myself sitting between Tom Fielding and a guy called Piers, and opposite the Chairman whose name was Frank. Penny sat on the other side of Tom with Grace on her other side. Tom was older but tall and handsome. Piers was younger and also very good-looking. I later found out that Piers was Tom’s son and that the Fielding family owned the biggest stake in the business. But initially I just thought that he was the young marketing guy.

We started talking to one another about the latest trends in marketing theory and we could not stop. Frank raised some business questions and we politely remained silent for a bit, but then went back to our own conversation.

Penny who had been focused more on business turned to me and said: “We could do that; don’t you think Emma. Targeted at women, should it be a woman selling it?”

I had no idea what she was talking about. I was in my own world with my new friend. Then suddenly an idea just came into my head. Not even into my head – it just came off my tongue.

“I think a man should sell it. Woman do listen to men. But he should tell everything about why it would not be preferred by men. That marks it as a product for women. They will listen to him but buy it because he wouldn’t. I think that could work.”

There was silence around the table, so I felt I needed to add: “Just an idea. We would need to talk it through”.

Tom said: “What do you think Piers?”

“Let’s do that,” he said. “Let’s see that idea developed and presented. So, I guess that means you’re hired ladies.”

It surprised me that it was Piers who made the decision. He seemed only a little older than me, and I assumed that he would be low level. He made the decision to hire us. Then he turned to me and he didn’t talk about it all, he went right back to what we were discussing before business rudely diverted our attention.

After dessert Frank and his wife left, then Grace, and then everybody except Tom and Penny and Piers and me. Tom suggested that we go up to the sky bar for a night cap. It was clear that he was interested in Penny beyond business. I understood that he was no longer married, and everybody knew that Penny had always been single. There was some thought that she might have been a lesbian but it was pretty clear to me that, at least in the case of Tom, she certainly was not.

We had a cocktail, and then another. Piers whether I would mind joining him on the terrace, I think he said for a cigar. I told him that he could light up but that I did not smoke.

“Neither do I,” he said. “It was just to get you alone for a minute.” I laughed.

It was a little cool at that height and he chivalrously put his jacket around my shoulders. He said: “It looks like we might be working together so I felt I needed to ask what your view was on office romances?” He paused. “As a rule, I discourage them, but all rules must accommodate exceptions.”

It felt like more than flirting. It felt like something very serious was under discussion. The truth is that I sort of liked the idea of romance. But of course, there could be no intimacy. I had a penis for God’s sake. The thought that my attraction to this man might be sexual, let alone homosexual, never crossed my mind at that point.

I found myself saying: “As a rule, I don’t like rules. They don’t fit with my rebellious and creative …”.

He kissed me. What I should have done at this point was to push him away and spit out any of his saliva that may have entered my mouth. So why, oh why, did I throw my arms around his neck, making his jacket fall from my shoulders onto the tiles. But his arms were there, wrapped around me.

“I feel I may have taken advantage of you,” he said. “Maybe too many drinks. If you still feel as passionate as this in the morning, then we must talk. After business hours, of course.”

When we got back inside, I saw that Tom had his arm around Penny. I was now starting to get a little worried that evening might close with sex, and that meant me being outed as a tranny and a fraud. I suggested that we share a cab and she agreed.

“In all my years in this business,” she said as the cab pulled away with only us in it, “I have never fallen for a client. But no at forty, a career businesswoman, I think I have just found the man of my dreams.”

“Me too,” I said, slightly dreamily.

“It must be the work first, Emma,” she scolded. “But what a guy – charming, intelligent, witty, good-looking and so, so rich.”

“Penelope Garret,” I scolded back. “You sound like a gold digger.” And we both giggled like school girls – like school girls talking about boys.

So exactly what was going on in my head. It wasn’t until I lay in bed in the morning that I even thought about it, I slept so well that night. But lying there I needed to rationalize the fact that I had returned the kiss from Piers, perhaps with interest. The hormones must be turning me gay. Or had I always been gay, or bi, or perhaps transgendered. That might account for how easily I had fallen in to the role of Emma, how comfortable I felt in her body.

But I had to get to work.

After my shower, I looked at myself in the mirror with my penis tucked between my legs. That made more sense. I looked so much better without it. I looked normal. I looked like a normal but very pretty, young woman. When I opened my thighs, it flipped out. I looked like a freak. I burst into tears.

On my way to the office I wondered how I could ever have a happy life. I was so much happier as Emma than I had been before. I had all of the skills that were needed but with the looks and confidence to sell those skills. I had style and grace too. And now I had romance. But it was all a lie.

It was as if I faced to options. I really was on the horns of a dilemma, and about to be gored. I could go back to a drab life and look forward to a man’s future of responsibility and fatherhood, or I could choose the vibrant and colourful world of womanhood and surrender my last vestiges of manhood. There was no other way.

What would you do?

Penny almost decided for me. When I presented my draft proposal a week or so later she asked to speak with me privately.

“Tom is getting very serious with me,” she said. “And he tells me that his son is crazy about you.”

“His son?” I asked.

“Piers is his son,” she said. “Your young Mr Millionaire and his father, Mr Multimillionaire. I think that we have hooked them both.”

She was smiling and so was I. My first thought was not about the money, it was the feeling of knowing that somebody was ‘crazy about me’, especially when that guy was as great a guy as I knew Piers was. Then I had a sudden thought in my head of my life as the wife of such a man. Loved, and living in luxury.

I had to take a grip on myself. I had to shake off these thoughts. I was a man. A man in a dress. A man dreaming about my prospective husband.

“This is going to be difficult,” I said, sadly.

“So, you still have your tackle?” she asked.

“My what?” At that moment I simply had no idea what she was talking about. But there was no doubting that she was looking at my crotch.

“How long have you known?” I felt deflated. Who else knew my secret.

“At the dinner I noticed something,” she said. “It raised the possibility. You have now just confirmed it. I never would have guessed. You are a perfect woman. So, I can only guess that you have not had the operation yet.”

Yet? I simply said: “I had never regarded it as necessary. Before now, that is.”

“You need to tell him,” she said. “Many men would not consider a relationship with a transwoman. You need to let him pull out. But if he wants you, then I think you should make a life together. He is a fine young man. No woman could do much better.”

She walked over to me and hugged me. I realized it was because my eyes were full of tears. I am not even sure why. It was just too much emotion, I guess.

She told me that we were presenting to Piers the following day, so we needed to get ready. That meant both presentations – the material and the ladies in charge. Get together with my team, and book the salon again. I rushed back to my station to tell everybody the good news.

It did not even notice how angry Siobhan was. Maybe she had been angry all along and I never even noticed? Maybe I was like Pollyanna, prancing gaily through a happy life as evil grew around me. Everybody has their breaking point, and I suppose when somebody like Siobhan learns that the girl (who is not really a girl at all) who took your job, has now attracted the city’s most eligible bachelor, something has to give.

When we presented, I was hoping that Piers and I would be winking at one another across the table. Tom was certainly doing that to Penny. We both looked stunning. Why was he so cold? It was worse than that – when I did catch his eye, the look was a millions away from the looks we had passed only a few nights before. It was a look of disgust. I knew that he knew what I was. I just did not know how.

I suddenly felt physically sick. I had to excuse myself in the middle of the presentation. I rushed to the ladies and I threw up. I retched and cried a million tears into the toilet bowl.

Penny came to look for me. She told me that they had bought into the campaign, but Piers had requested that I not be involved. I burst into tears all over again. She put an arm around me and hugged me. Somehow that made me feel a little better.

“I suppose Siobhan can manage it?” I said, trying to focus on the work.

“She would be the natural replacement,” she said. “But she apparently knows who she is and will not have her. Something about betrayal. I don’t understand what that is about.”

“I do,” I said.

I had to go home. I could not function. Two people that I cared about were now dead to me, or I was dead to them. I was an emotional wreck, not assisted by now being hopelessly female. Sometime we girls just have to take a box of tissues and sob it out.

I was expecting to hear Siobhan at the door. I had put the chain on so that her key would not be enough. I wanted to confront her. I was steamed up. I was going to do something awful to her. I swung the door open with a face that I sure looked as wild as harpy.

Piers was standing there.

I wonder now how I must have looked. I had been crying and throwing up all afternoon. My special hairdo was a mess. My makeup was totally ruined. I must have been the ugliest woman on the planet, if I were one. And I would have looked as mad as hell. But then suddenly, not. Then I would have looked at him with utter despair, the despair of somebody who could have known such perfect, and who had lost it through her own selfish deceit. What kind of look was that? Surely just as unattractive.

Why then did he take me in his arms? Because I fainted, that is why. I did that most feminine of things when confronted with the ultimate shame – the shame of being seen for what you are. A worthless impostor.

“Emma?” My name through the haze. My name. Emma. Not whatever that other name was.

“I’m sorry,” he said.

“Oh Piers,” I said. “I am the one who should be saying that. You have every reason to hate me.”

“You might be right about that,” he said. “But for some reason, I don’t. I thought I would, maybe I even want to, but I can’t.”

“I must look awful,” I said. What a thing to say. I was slumped in his arms. He must have caught me before I hit the floor. He was holding me, brushing the hair away from my face, still wet with tears.

“Pretty bad,” he conceded. “But still beautiful to me.”

The End

© Maryanne Peters 2019