WILF
A Short Story
By Maryanne Peters

I was an experienced transvestite. I had been closeted for years. I denied it to myself and did not tell my wife the full extent of my need to dress. She was open to “kinky sex”, but she drew the line at anything more than that. I decided that I would lie to her as well as myself.

But some needs cannot go unsatisfied. I took up sprint swimming so that I could shave my body. I never really liked swimming, but a smooth body was important to me. I used to keep a secret stash of clothes and look forward to the days when I was alone and could dress up.

I engineered the occasional “business trip” or extended trips that were real to allow time to be able to dress and present as a woman.

Yes, it was not enough to stand in front of the mirror and jack off. I had to do more. I had to go out and be seen dressed as a woman. I found that more satisfying than spilling into my hand. To have a man stare at me as if I was a woman and then to smile at him as I walked by was like a drug I could not get enough of.

I had to keep on with it despite the risks. It was not getting attacked and beaten up that concerned me – it was having to explain the bruises to my wife. Initially it seemed that I was prone to getting mugged. But the best defense is to pass. I learned that.

“Hey you! You’re a guy, aren’t you?”

“I am sorry mister … just because a girl is tall and works out a little you assume she is not a woman? What is wrong with you?”

If you have the voice right, and you look indignant enough, he will back off.

But somehow success just encouraged me.

I was fighting it because of my wife and our two boys. To the boys anyway, I was a god, at least until they became teenagers when all kids realize that there father is a dick. But I tried to be the example of the man I thought those boys should be – masculine. I could do that too.

I always thought that the woman was the lie.

Then one day my wife found out. It was worse than that – she found the stash and then looked into what I was doing. I was away overnight and she followed me. She caught me in a bar being chatted up by a guy. It was the worst night of my life. She knew my secret, and so did he.

“Were you going to let that man fuck you up the ass?”

“Darling, I am not gay. I would never do that. It is just a game. A fantasy. A compulsion.”

But it was all over. I had to admit that I had been doing it for years. I had to tell her that it was a need – I had fought it and failed, but it was not going to go away. Some women may have accepted it, but she did not. Honestly, I admire her for that. I deceived her. I was in the wrong.

She could have kept if from the boys, but she didn’t. I don’t admire her for that. That was just spiteful. The boys were disgusted, and I could understand.

“Life is complicated, guys. People are complicated. Faults do not make a person bad.”

You can say whatever you like, but when people walk away in a situation like that, you have to just hope that one day they will come back.

She also told all of our friends and my work colleagues that I knew. It happens with all separations that friends are often left with a choice – “him or her?” But if it is “her or that?” the choice seemed against me. At my work at least my employers were more understanding.

“Bruce, what you do in your own time is your own business. Just keep your hours and meet your marks and we won’t have a problem.”

I still had a job, but everybody looked at me strangely, and maybe they were laughing at me behind my back, or maybe not. If I thought they were, that was the problem.

But I am practical person. You may have worked that out. You don’t address your nature like I had and keep it a secret like I did, without being practical.

The fact is that I was alone, so I could live however I liked, at home.

I let my hair grow. It was not my intention to grow it very long as I still worked at a man, but the sensation of pushing bangs out my eyes, or putting a lock behind my ear, or washing a full head of hair with floral shampoo, was deeply satisfying. Now I could do that.

My beard was always a problem when I dressed, so I decided to get selective electrolysis on my chin and top lip to keep the five o’clock shadow away. I could now also wax my arms, and use moisturizer on my body after shaving, and sleep in a nightie. It was not a thrill as such, but just a sense of happiness that made the loss of my family bearable.

With these improvements I could go out on the town as a woman. I was not the same kind of woman as I was before when I was not wearing a wig. I washed my hair and used all the hair techniques that I studied on internet vlogs to build volume and shape, and with shorter hair I needed to have my ears pierced and use drop earrings.

Somehow without a wig I felt even more secure. Every transvestite who relies on stealth fears the moment when the wig comes off and you are revealed as a fraud. A drag queen might say that this is the whole point, but not somebody like me. It was like I said to my boys – “People are complicated”.

I suppose this all took me to another level, or another few shifts along the spectrum from transvestite to something else, but I kept telling myself that it was still just a fetish – for want of a better term.

I suppose a few transvestites wonder what it would be like to live full time as a woman, maybe just for a while. The problem was my job. I treated it more as a reality rather than a problem, as in I had a job which kept me anchored to the reality that I was a man, albeit with an abnormal proclivity.

But when downsizing came along, I had the option to take a redundancy package and I was thinking about it. Then as if to push me through that door I found the advertisement in one of the transvestite websites that I visited from time to time.

It was the offer of a job to “A mature wannabe woman looking for the chance to experience total immersion in life as a woman”. From what I understood the work was in administration in a large office and came with the option to take accommodation in an adjoining block, but the rate of pay was low for the work. The ad closed with the words “Please submit a resumé and a photographic portfolio”.

My first reaction was that this was some creep who wanted to hire a transvestite for his own pleasure and take advantage of the fact that such person might jump at an underpaid job just to live a few months on the other side. On that basis I was ready to reject the chance and the redundancy.

But then I figured that the redundancy would allow me to try this. I could try to live as a woman, just to see what it was like and then go back and find a job somewhere as a guy if it did not work out.

I thought that there might be plenty looking for the position, so I decided to put it down to chance and send in my CV and some selfies.

A week or so later I received a letter advising that I was on the shortlist, and a request that I attend a zoom interview. The man on the other end identified himself as “Will”. He seemed like a regular guy – he was older than me and good-looking and he was more interested in my qualifications and work experience than asking me to show him how I looked.

“You’re overqualified and with plenty of experience,” he said.

“But no experience as a full time girl,” I replied.

“Well, you’ll get that because you have the job.” Just like that!

I took the redundancy, moved cities, took on an apartment belonging to the company, and was ready to start work the following day when I got another call from Will.

“I have booked you in for a makeover,” he said. “Just to give you confidence on your first day. We normally expect you to start at 8:00 but tomorrow you hairstyling and makeup starts at 8:00 so you can report when you are done.”

The hairstylist told me to forget about the wig. I had enough hair for a short bob and all it needed was treatment to make it soft and shiny, and a new color. A new color for a new life.

The beautician said that I had a lot to learn about the right makeup for a daytime look, but she was ready to help. She loved the permanent depilation I had done and booked me in for more. She gave me a perfect makeup job.

I felt like a million dollars when I walked into the office and met Will for the first time. He was taller than me even in the heels that I was wearing and he was charming. I felt then that I had made an impact, and I had.

The first time that he took me to dinner he admitted that his motives in recruiting me were less than honorable.

“The truth is that I had a personal assistant before you who was transgender, and she was the best PA I have ever had. Like you she was overqualified and had taken the job simply so she could make a new start and live a female life. When she left to get married after her surgery, I was not able to replace her with anyone who was any good, so I decided to try to find somebody in the same circumstance. I now see that I am taking advantage of your deepest need and desire. Please forgive me.”

I said – “To be honest I am a little relieved. I was worried that you might be a tranny chaser of some kind, interested in me sexually, I mean.”

“Well, I am not a tranny chaser. I am only interested in women. But …”.

He simply stopped talking and he looked at me. It seems crazy to say it, but it was the kind of look people write songs and poems about. We just stared at one another in silence over our poached salmon.

“I am not a woman … yet,” I said. The extra word just appeared, as if he had forced it out of me. I thought that I knew what I was, but now it seemed that I was becoming something else.

Anybody who knows will tell you that a transvestite and a transwoman are two very different things. I had always assumed that I was the first of these, but even in the relatively short time in which I had been living the life of a working woman, I was starting to wonder if I had been wrong all along.

Or can people change? Why was I attracted to him? I had never felt for a man the way I felt for Will. When I cruised for compliments and free drinks in bars as part of my cross-dressing thrill seeking I could recognize a good looking man and warm to his advances as a part of the great game of human sexuality, but this was something else.

If this was love then I wondered if I had ever felt this for my wife in the same way.

Will reached over the table and took my hand gently in his. “Would you accept an offer of another makeover from me?” he asked.

A few weeks later I was checked into the Beautifex Cosmetic Surgery Clinic. He had specified nothing drastic. He still wanted to see me. He just wanted the maleness removed. My browbone was ground down and my hairline pulled forward. My nose was made a little smaller and my lips a little bigger. And then there was my chest – two big round creamy white and jiggling breasts – but not over-stated.

And a few months after that a different hospital, and a further, more substantial surgical procedure.

I invited my wife and sons to the wedding, with a letter apologizing for not being the person that I really never could be. It was just that back then I never realized who or what that person was. I was somewhat surprised that all three of them turned up. But I was not nearly as surprised as they were to see the woman I had become.

A woman that other men might like to … a WILF.

The End

© Maryanne Peters 2021