Amy Lives
A Short Story
By Maryanne Peters

It was a Sunday night - October 31, 2010 when my life changed, or maybe it began then. I had been married for less than a year to Romana, the woman I had always thought of as my best friend. We were ready to start talking about having children. I had always wanted to have children – it was a strong drive in me that I never really understood. I know now that there was a lot about myself that I did not understand, but that was going to change too.

We were invited to a fancy dress party, with the theme being that we should dress as our favorite singing star. My wife had decided that she would go as Adele, perhaps because she was carrying a little weight, just like her idol was then. But it was her idea that I should go to the party in drag, dressed as Amy Winehouse. It was not such a stupid idea, although I did initially refuse as a matter of male ego. I was dark with large eyes and not the best chin, and my nose was perhaps not quite as prominent as hers, but it could be accentuated with makeup. Makeup was the key to her look – those shaped brows and dark wings at the edges of her eyes. It was quite a simple look to pull off.

Ro was great with makeup. She had Adele’s look just right and was able to use her own hair plus a wiglet appear just like the singer. When she started on me, I was laughing and she was telling me to be still. She insisted on plucking a few hairs between my brows, which had me howling, but she swore that it would not show. Then she said that she might try to use my hair just as she had done, using my solid hair line and slight length to tease for height, and adding a long fall. She capped it off by selecting a sleeveless dress and drawing a few tattoos on my shoulders. She was very pleased with herself, and could not wait to show me “Amy” in the mirror.

I smiled and told her that if I looked like shit, I would not be going to the party. Then I came to the mirror and looked at myself, and everything shifted. I can’t quite explain it - It was like the world had moved under my feet, and it was now a different place. It was a strange mixture of horror and excitement, as if I knew this was going to change everything even before it did.

“Well, I think that you look fantastic,” Ro said, maybe sensing that my silent stare was disapproval. “You are definitely going as Amy … Amy. Yes, I will call you Amy all night.”

I had heard Amy Winehouse speaking on a short documentary about her album “Back to Black” and I found myself replying in her voice – a London cockney accent and a tone that was quite deep. I said – “Or right then, why the fuck not”. Ro seemed a little shocked but then clapped her hands with a laugh.

Somehow it all seemed so easy and natural that it should have seemed weird, but it didn’t. I walked in the heels Ro had found for me in some charity store, and I flapped my arms about and chattered in my fake accent all night. I was a huge hit. We were a hit, because Ro as Adele also did her best with Adele’s cockney talk – not quite as good as mine, but a good fit. Two London girls having a good time.

I have to say that a few people who met me, even people who knew me, were a bit thrown by my appearance and behavior. These were people who I now understand, realized that this was barely an act on my part – it was as if I had become somebody else.

It was only natural that I should be a bit flirtatious – I thought that it was in character to do that. But the disconcerting thing was that I found myself looking at men that I was talking to and having sexual thoughts. I just hoped that they could not sense it, but there were female desires welling up in me.

I was unsettled but having a good time. Again, it was a mixture of emotions that seemed powerful but confusing, and still enjoyable. I don’t think that I had ever had so much fun before that night. After it was over I remember spending part of the night awake and thinking about how my life had been a slow plod through an expected existence until the day of my death, with just a glimpse granted of another life completely.

When she woke Ro spoke about how wonderful that party had been for both of us, and I said that maybe we should do it again the following weekend.

“You mean go out as Amy and Adele?” she said.

“Well maybe not those names, but yeah … two girls, but maybe not from London.” We resolved that we would do just that, starting Friday night.

We were both a little late to our workplaces that morning, but so were many. I remember that when I sat at my screen everything seemed a little different. I put it down to a hangover, but that was not it. There was something hanging over me, but it was not the effects of alcohol – I had not drunk that much. All I could think about was the week being over and the chance to dress up on Friday night.

I would still be Amy, but not Amy Winehouse. The makeup was toned down, and the nose was hidden rather than highlighted. The look was really much more attractive. Ro decided to introduce herself as Rosemary, because she said that I was bound to call her Ro. She could not call me anything other than Amy when I was dressed as a woman.

We went out that Friday to a bar and we were hit on by men who bought us drinks. We just chattered lies to the guys for hours and then simply had to go when things started to get hot and heavy. We did the very same thing on Saturday night.

The thing is that during the day on Saturday I never stopped being Amy. It was sort of understood that this was all a part of perfecting the character that would emerge at night, but the truth is that I simply felt better as a woman – it just seemed right, somehow.

It may have been that weekend or perhaps a few weekends later, when Ro realized that I was more Amy than the man she had married. She was upset but she said that she understood that I needed to be true to myself and that she would help me.

It really was as simple as advising my work that I would be presenting as female from the following Monday, and then doing just that. For me it just came as a relief – I did not have to pretend to be a man anymore – I had found my true gender and I was now free to live it.

It was just Amy and Ro after that, but I think that we both knew that we could never last as a lesbian couple. I know that plenty of relationships do, where love survives total change because you have always loved the person not the gender, but in my case the gender changed everything.

I guess, perhaps like the lady who started it all, I was a little bit old-fashioned – more jazz and swing than rap and hip-hop. Maybe like her I could have been better off without men, who never treated her right, but I found myself attracted to them none the less. I had the looks that drew men in, and I used her as my example. Even without adopting her style I cultivated a look of that ‘little girl lost’ innocence with a mischievous enthusiasm. I was never short of propositions.

On July 23, 2011, Amy Winehouse died. I was very sad because whether or not you liked her music, here was somebody with real talent and a beautiful soul who had been cruelly plucked from the world. I somehow thought of myself as having an obligation to replace her – not as a singing star but as a woman.

After I had wept a few tears, I decided that I would take the step of leaving my manhood behind and book surgery. It was time to be able to accept some of those propositions. It was time for Amy to live.

The End
1462

© Maryanne Peters 2026

Author’s Note
In October 2025, over on Fictionmania, Lottie wrote a review to a story I had written as follows: “I was I thought a happily married straight man hoping 1 day to have kids when my wife convinced me to dress as a girl ( Amy Winehouse ) to go to a fancy dress party I couldn’t believe how good and convincing I looked when she finished dressing me and doing my hair and makeup. We had the best time and the next weekend I asked her if we could go out again with me dressed in ordinary girl’s clothes she agreed and it became a weekly routine for us, but it was after the first time that I realised that I should have been a girl. My wife also realised after a few weekends and we talked about it and she helped me become the girl I should have always been. Thankfully we are still best friends and we both acted as bridesmaids at each other’s wedding and we still have regular girls’ nights out but not every weekend because we are both mums now Tricia showed how much she loved me by having a surrogate baby for me using my banked sperm and a donated egg from my cousin. Please write a story based on my brief description of my life.”