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As I walked down the street, hearing my heels tap on the pavement, and feeling the cool breeze brush my slip and skirt against my stocking-clad legs, I wondered if cis-women get the same sensual rush as I do from such things? Perhaps not as they are so used to it, and that also depends on them wearing skirts which so few young women do nowadays. As for me, well I wore trousers for over twenty years and have no intention of wearing them ever again except for rare occasions when a skirt is impractical, like climbing a ladder.

All this is by way of revealing that I am a trans woman and couldn’t be happier. In fact the day I woke up after my final surgery was the happiest day of my life, even if I felt sore. My older sister was there to greet me and welcome me to the ‘A team’.

Like so many others, I knew from an early age that I had been born with the wrong body, but when I tried to explain it to my mum, all she could say was that it was a feeling that I would get over, while I knew that I never would. She was a single mum, and I remember one time when I walked into her bedroom on a rare occasion when she was getting ready to go out with one of her few men friends. She was sitting in front of her dressing table, gazing into the mirror as she applied her makeup. I can recall that she was wearing a pale pink slip with lace around the hem and I stared because I could never remember seeing her wear anything like it before. I asked her if I could wear makeup when I was older and she explained that men didn’t wear makeup unless they were actors, and right then I decided I would be an actor!

My school days were not very happy. St Mark’s Grammar School was an all-boys school, and had quite an emphasis on playing sport and I was hopeless at it. Football or cricket were nightmares. If I was forced into a team, then I spent all the football matches ‘on the bench’, and as for cricket I was the last batsman to go in, swung wildly at the ball and rarely made contact. It was a rare occasion that I made it through one over.
There was only one of the boys who showed any kindness to me. His name was Rodney and I thought he was the handsomest boy in the school. Looking back, that was a strange thing for one boy to think about another. Well, that’s what I thought at the time.

There was one other boy whose name I remembered – Malcolm, and the reason for that was his skill at football. Almost single-handed he took our school through the inter-school tournament to the final and I’m sure we only lost because he was tripped – deliberately no doubt, sprained his ankle and had to spend the rest of the time on the sidelines, watching as the two goals he had scored were rapidly overtaken and we lost 5-2. Malcolm was also a good cricketer and it seemed a shame that one person should have so much talent in sport while others such as myself had none at all.

Malcolm was no academic but that hardly mattered since from an early age his sole ambition was to become a professional footballer, something he achieved, joining one of the Premier League clubs’ trainee squad soon after he left school.

The last year I was at school, we had a new English master, Mr Higgins whom we nickname ‘Enery’ and who was a great Shakespeare enthusiast. Each year, near Christmas, the school presented a play to which all the pupils, their friends and relatives were invited. It must have occurred to you that there are very few plays without some female characters, and having no girls at our school, we usually ‘borrowed’ some from the local convent school to fill the parts.

Mr Higgins decided that we would perform an abridged version of ‘’Romeo and Juliet’ and started to advertise the fact, confident that we would get girls to play Juliet, her mother and nurse. However, what he had not been informed because it was a great scandal, was that during the previous year one of the girls and one of our students had had a brief but passionate love affair which culminated at the after show party with the inevitable outcome. As far as I know they did not get married, but the other outcome was that the Mother Superior of the convent school decreed that none of her girls would ever join the cast of a St Mark’s play again.

I, along with a number of other boys had expressed interest in performing in the play, without a thought that I would play anything other than a male part, so it came as a great surprise when, as we were gathered around Mr Higgins in a semicircle in the school hall, he revealed that he would need some boys to play the part of females in the play, and of course mentioned that this was common practice in Shakespeare’s day. He asked several boys to read the part of Juliet, starting at the balcony scene which he had largely left untouched, getting one of the other boys, in fact it was Rodney, to read Romeo. Predictably they were hopeless, and then he turned to me. Of course, he was not to know that I had longed to be a girl all my life, so as I started to read those wonderful lines:

‘O Romeo, Romeo! Wherefore art thou Romeo?
Deny thy father and refuse thy name;
Or, if thou wilt not, be but sworn my love,
And I'll no longer be a Capulet.’

It was as if I was in a dream. I’m sure that Mr Higgins was staring at me but he let me continue uninterrupted.
At the end of the scene there was silence from the other boys, and then someone started to clap and I blushed scarlet from my neck to the roots of my hair.

I won’t go into details, but obviously I got the part and Rodney was given Romeo. Two of the boys’ mothers were co-opted to play the parts of Juliet’s mother and nurse. I was given permission to grow my hair long, and Rodney and I spent hours rehearsing our lines, even doing it atter school. I loved spending time with him. Anyone who has seen the play will know that Romeo and Juliet kiss, and while we skipped that at first, eventually it had to be included in the later rehearsals. I had to pretend it meant nothing to me but it was in fact magical and I knew that I was in love with Rodney. I wasn’t sure how he felt about me, but of course nothing was ever said about it.

Eventually the time came for dress rehearsals and mum had made me a beautiful gown for the daytime scenes, and bought a nightgown for the night ones. She had also purchased a ‘training bra’ which was slightly padded to give the impression of the small breasts of a girl in her early teens.

It came time for the performances and they were scheduled for a Friday evening, and a Saturday matinee and evening. The school hall was packed and the performances went very well, one might almost say surprisingly well for a school production. Mum and my elder sister attended and later Mum passed on to me a comment she heard from one of the audience members as she left the hall.

The woman said ‘I heard that they had no girls in the cast this year but obviously they managed to get one to play Juliet’. I blushed when I heard this and didn’t know whether to act pleased or angry.

I should mention that at that time my name was Jack and now it is Jacqueline. Due to a misprint, whether by accident or design my name in the program was printed as Jac which could have been interpreted either way.
I had made up my mind that I wanted to study nursing after I left school, While nursing has always been thought of as a women’s career, there are now a number of men who have taken it up and at the risk of sounding boastful, I really thrived in the hospital environment, and passed all my exams with flying colours.

Five years passed during which I made up my mind that I was going to live my life as a woman. I passed all my tests, went on hormones and started on my ‘real-life test’. I could now dress as a female nurse and continue my career. All the other nurses knew about my transition of course but were very supportive, and the patients never knew.

And so I come to that evening when I walked down the road after attending a theatre matinee. Like most of the audience, especially the women, I had dressed up for the occasion, It was warm, so I wore a pretty dress with a flower pattern, together with stockings and heels, and ‘I felt a million dollars’ as the saying goes.

I reached the bottom of the street, turned the corner and stopped at the bus stop. I was standing there looking around when suddenly I saw him. He was sitting in a doorway in what looked like good clothes but they were stained and creased. He looked emaciated but there was something about him which looked familiar. Almost without thinking I moved closer to him. I had noticed a food stall just down the street, so I spoke to him.

“Hi, I’m Jacqueline. You look like you might like a feed. Can I get you soup or a sandwich?”

He slowly raised his head and looked at me. At first the look was suspicious and then he looked puzzled. I wondered if he would reject my offer and say he only wanted money for drugs but he didn’t.

“Yes ma’am, I’d appreciate that,” he said.

I walked over to the food cart and ordered a disposable cup of chicken soup and a ham sandwich, and carried them over to him. He thanked me and began to eat and drink ravenously. He obviously hadn’t had anything to eat for some time. Once he had finished, which didn’t take long, he wiped his mouth with the back of his hand and looked at me again.

“Do I know you from somewhere?”

“Well I’m a nurse – maybe you’ve been in St Mary’s hospital where I work?”

“No, never been there,” he replied.

“Do you mind telling me your name?” I asked, thinking that he seemed familiar to me too.

“It’s Mal,” he said. “I used to be a pro footballer.”

This struck a chord with me. “There was a Malcolm at my school that wanted to be a professional footballer,” I said.

“Yeah, that was me, but it was an all boys school – you couldn’t have been there,” he replied.

“Well in those days my name was Jack,” I said, blushing slightly and not even sure why I had admitted that.

“Jack,” he said slowly, peering at me. “Yeah, I can see it now – Jack who was no good at sports; but I would never have known if you hadn’t told me.”

I blushed even deeper. “Yes, that was me, but if you don’t mind me asking, what happened to you?”

Mal managed a rueful smile. “Buy me another sandwich and a coffee and I’ll tell you the whole sordid story if you like,” he said.

Just up the street was a café with some outside tables. I knew they wouldn’t let Mal inside, but I guessed they would accept him outside, especially if I was with him, so I invited him to accompany me and have a proper meal. Mal scrambled to his feet, picking up his coat and a dirty blanket and we walked up the road to the café – an odd couple if ever there was one.

We sat at an outside table and a waiter came out to serve us. It was obvious that he wasn’t too happy about Mal’s appearance but he said nothing.

“I should have told you, I’ve got no money – what can you afford?” asked Mal.

“Whatever you like,” I replied, so he ordered a steak, chips and salad while I had a coffee. I waited while he consumed his meal rather than quiz him while his mouth was full. Eventually he was ready to talk.
“Alright, you want the story, I’ll tell you and then you’ll want to go and never see me again and that’s fine. Thank you for the food.”

“Tell me your story and let me make up my own mind about that,” I replied.

“Well, you know I always wanted to be a professional footballer, and I got my wish after I left school. I joined a training squad for one of the top teams, I won’t mention which one, and I went well. It was only a matter of months until I played my first match for them and I scored a goal. The world was my oyster. I was now on a good wage, more money than I’d seen in my life, and I started to spend it. I bought a flat and a flash sports car. You know the expression ‘a fool and his money are soon parted’? That was me – the fool.

Life was great. I went to the best restaurants and the women were around me like bees around a honey pot.” He paused and looked embarrassed. “I don’t mean that all women are like that but some do seem to chase after footballers, and they are the expensive sort. Then I started to gamble, and that was my real downfall. I quickly went through my savings but there were people who were happy to loan me money and were never in a hurry for me to pay it back, but I should have realized, payment is always required in the end.

“One day two men appeared at the flat. I was informed that it was time to start repaying my loans. They told me how much I owed and I was shocked. I told them that I didn’t have it at present and I needed time to pay. They said they would tell their boss and left. I went to the bank but after reviewing my account statements, they weren’t willing to loan me the amount I needed. I couldn’t approach the club after all the money they had paid me and I had to tell that to Laurel and Hardy, well it was more like Hardy and Hardy, when they came back. But now they had a proposition for me. It seemed their boss was also a gambler but a smarter one than me because he liked to be sure he would win. If I would ‘accidentally’ miss scoring a few goals, he would start to write off the loan.

“Now I was a pretty good forward and it was rare for me to miss scoring a goal or two per match, but the next match I was to play, I got the message that I should miss at least one goal. The opportunity came and normally it would have been an easy shot, but I kicked the ball over the crossbar. The game should have been a draw but we lost one-nil. If it has stopped at that it would have been ok but a couple of games later I was given the message to miss again and this time the crowd didn’t like it and I was booed. I started to worry, but what could I do?

After the third miss of an absolute sitter, I was called up before the management team who asked if my eyesight was going bad. I felt so distressed I broke down and confessed everything. They asked why I hadn’t come to them first and they would have helped me. I cursed myself for being a fool, but by then it was too late. They said I had to leave the club but they wouldn’t admit to games being rigged, so it would be put about that I had suffered an injury and couldn’t play anymore. I sold up my flat and my beautiful sports car and made enough to clear my debts, but now I had nowhere to live and suddenly very few friends.

I ended up in a cheap boarding house, and the first night there most of my few belongings were stolen. I managed to get unemployment benefits which is barely enough to live on. A couple of weeks ago I was wandering the city streets thinking perhaps I should throw myself under a train when by pure chance someone recognized me. It was Rodney from school. You might remember him – didn’t you act with him in a school play once?”

At the sound of Rodney’s name I could feel myself blushing. Of course I remembered Rodney and our kisses.

“Er, yes, we were in ‘Romeo and Juliet’,” I said.

“That’s right,” Mal said. “You did a darn good job as Juliet. I guess I can understand why now. Sorry, I hope I’m not embarrassing you.”

I tried to laugh it off. “It was a long time ago,” I said.

“Anyway, Rod was really kind – he shouted me a meal just like you did and he bought me a cheap phone, put his number in it and asked me to call him regularly so he knew I was ok. He even offered to let me stay at his place but I didn’t like to so I thanked him but refused.”

“So where do you stay now?” I asked.

“I’m sleeping rough under a railway bridge with the other homeless men, but it’s pretty safe because none of us have anything worth stealing. Anyway, the next time I ring Rodney, shall I tell him I saw you?”

“Better not,” I said “Maybe he’s got a wife, she wouldn’t like it.”

“No, he’s single again. He did get married but it didn’t last. I sort of hinted for him to tell me what went wrong but he wouldn’t say. Anyway, I’m holding you up, I guess you were on your way home. Would you mind if I had your number too, just in case?”

‘In case of what?’ I wondered, but I gave it to him anyway, and we parted ways. I wondered if I would hear from him again.

Two days later, I had a phone call in the evening. It wasn’t Mal, but the voice was vaguely familiar. “Jacqueline? This is Rodney from St Mark’s. We went to school together. When Mal rang me he told me he met you and that you had a lifestyle change.”

“You could call it that,” I replied, feeling my face reddening.

“You know, I’m not really surprised?” he said. “Do you remember us in ‘Romeo and Juliet’ in the school play?”

Remember? How could I ever forget. I couldn’t think what to say, so I said nothing.

“Well, I’ve never forgotten it,” said Rodney. “You were amazing.”

“Thanks,” I replied and there was another pause.

“Look, I hope you won’t think me forward after all this time, but Mal seemed to think you are single and so am I, so would you mind me asking if you’d come to dinner with me?”

I finally found my voice. “Er,no. I’d like that” I replied.

The upshot was we arranged to meet at one of the city’s best restaurants the following Friday. There was a reason for that – it was my day off and I would need most of it to get ready.

One of the advantages, some people might call it a disadvantage of being a woman is deciding what to wear to an evening out. It’s so simple for men – just a nice suit, shirt and tie and they’re ready. I looked in my wardrobe and decided that nothing there was suitable for a dinner with Rodney. I wanted him to see that I was now one hundred percent a woman. Well no, I couldn’t have children so make that ninety percent.

Then I remembered seeing a beautiful evening gown in a boutique window I passed on my way to work. It was silk and in the palest of rose pink colour. I had salivated over it but realized that I had no reason to buy it, but now I did. The following day after my shift at the hospital, I went to the store, and thank goodness it was still there.
I tried it on and it fitted perfectly. The shop assistant said it might have been made for me, something she probably says to all the customers, but I believed her, and I bought the dress.

For the rest of the week I found myself ridiculously excited at the thought of my first date with a man since my transition. All sorts of scenarios played out in my head – supposing Rodney turned out to be a sleaze? Well, he didn’t know where I lived and I could always block his number on my phone. Then again, he might turn out to be ‘Mr Wonderful’.

Like most trans women I had wondered what it would be like to make love as a woman. Was it as good as everyone said? Well it couldn’t be worse than my few experiences as a man which never felt right to me, nor I’m sure to the girl I was trying to please.

Friday finally arrived, and I had my preparations all mapped out in my mind. This was another contrast from preparing for a date as a man, which only required a shave and shower or bath before putting on a suit. I wasn’t complaining, you understand? Preparing for a date was all part of the enjoyment of the occasion. It started with a scented bath, followed by a trip to the hairdresser to put up my hair in a French roll. I could do it myself of course, but I wanted it to look perfect. Then it was back to my apartment to start getting ready in the late afternoon. My first job was to paint my fingernails and toenails pink to match my gown.

I had decided to wear my best lingerie set which was satin and a pale pink, not unlike the gown. Why did I chose it? Well it wasn’t because I expected Rodney to be ripping my clothes off – well not on a first date anyway. No, I enjoyed wearing pretty underwear because of the feel and look of it which made me feel sexy and feminine. Next, I donned very sheer pantihose. I know a lot of woman no longer wear stockings but I believe they make a woman’s legs look better, and besides, I like the feel of them on my legs. Then I sat down in front of my dressing table and started to apply the ‘war paint’ This took quite a long time because I wanted it to look perfect.

Finally I was satisfied and now it was time to put on my new gown and three inch heels. I stood in front of the full-length mirror and gave a slow twirl, thinking to myself that if Rodney didn’t like what he saw, well I couldn’t do any better than I had.

I timed the taxi to arrive five minutes after I was expected since I wanted Rodney to arrive first. The Maitre d’ bowed when I entered and led me to the table where Rodney was sitting. I confess my heart thumped in my chest when I saw him. At school he has been a good-looking boy, but now, ten years later he was one of the handsomest man I had ever seen. At my approach he stood up and from the look in his eyes it seemed I did not disappoint him. The Maitre d’ drew out my chair and slid it in to the table for me to sit down.

“Jacqueline!’ said Rodney. “How nice to see you again after all this time.”

I smiled and replied, ‘It’s good to see you too Rodney.”

“I’ve often wondered how you were doing,” he said. “However, the last person I expected to put us in touch was Mal. That was quite a surprise.”

“Well, I did tell him not to say that we had met,” I said and found myself blushing.

“Why would you do that?” asked Rodney.

“Well, I’m not exactly the person you used to know any more,” I said, my face burning.

“If I may say so, you look a lot better than the boy I used to know, but maybe a little like the person who played Juliet. Do you ever think of that?”

“Yes, I enjoyed that time,” I replied, thinking that I particularly enjoyed our kisses, but I wasn’t going to say that.

Seeing that I was embarrassed, Rodney picked up the menu and said “I suppose we should order.”

It was a wonderful meal and I enjoyed the conversation. To my surprise Rodney revealed that after studying English at university and getting his Master’s degree, he was back at St Mark’s, this time as senior English master and also Deputy Headmaster. I offered my congratulations. There was no doubt in my mind that I wanted to spend more time with Rodney and I hoped he wanted the same. I wondered what had caused his marriage to break up? Surely his wife could not have wanted a better man?

Eventually, as we enjoyed a post prandial port, the conversation turned to Malcolm and his problems. It seemed that Rodney also knew the real reason that Malcolm had ‘retired’.

“I’d like to do more for him,” said Rodney. “He’s a good person at heart and it’s a shame he was captured by the scourge of gambling.”

Eventually the evening was over, and Rodney escorted me to my taxi.

“I would like to see you again,” he said, and I smiled and said that I would like that too. “Call me,” I said, and I kissed him on the cheek.

That night I had wonderful dreams, erotic dreams involving me and Rodney. I was quite disappointed to wake up!

A week later Rodney and I met for dinner again. I wore my favourite lingerie set again and another silk gown, my ‘second best’, and this time I agreed to going to his house for coffee afterwards. I knew I had already fallen in love with him which seemed ridiculous after such a short time. Later, sitting on the couch the subject of the ‘Romeo and Juliet’ play came up again.

“That was the first time I saw the real you,” said Rodney. “It was the day of the dress rehearsal. I came out of the dressing room and you were standing in the hall, wearing that beautiful gown, with your hair braided and your makeup done. Your back was to me but you must have felt my eyes on you because you turned around and smiled at me. My heart thumped, you were so beautiful, and I knew I would never love like that again.”

“I remember that time,” I replied. “You looked so handsome. I’m sure I fell in love with you at that moment.”

“I think that the reason the play went so well was that we weren’t pretending to be in love, we were in love. Then came the kisses. I’d only ever kissed a couple of girls and never a boy of course, but when I kissed you it was exactly like kissing a girl. I’ve never forgotten it”

I said without thinking “Ten years between kisses is a long time.”

“Far too long,” said Rodney as he smiled at me and his lips gently came down upon mine.

Much later I awoke. It was dark and Rodney was lying fast asleep on the bed beside me. I couldn’t help smiling – making love as a woman was so much better than my few attempts as a man. What is more, it was obvious that I had given Rodney as much pleasure as he had given me.

With the coming of dawn, Rodney awoke and we make love again before I had to get up to go to work. After a shower, Rodney drove me home to change into my nurse’s uniform and dropped me off at the hospital.
Sharni, my best friend at the hospital took one look at my face and said “You look like the cat who got the cream”, and then she laughed as I blushed furiously. ‘Tell me all about it at teatime,” she said.

‘This is ridiculous,’ I said to myself. ‘You’ve only been seeing Rodney for a couple of weeks and already you want to marry him.’

Rodney and I spoke on the phone almost every day, and a week later he phoned me and said that he would like to invite me to his home for dinner and that we would have a special guest – Malcolm.

“I owe him so much for putting us in touch again and I think I’ve found a way to repay him,” he said. He refused to say more.

That evening I did not dress up like I had for my first couple of dates with Rodney as this would be ‘smart casual’, but I still wore a pretty dress, stockings and low heels.

I was pleased to see that Malcolm had made an effort to look tidy for the evening. He appeared to be wearing a new shirt, trousers and shoes and I wondered if Rodney had helped out with the purchases.

Rodney turned out to be a competent cook. The meal was simple, steak, mashed potatoes, mixed vegetables and gravy, followed by fruit salad and cream. Afterwards we sat in the lounge and chatted comfortably.
Rodney said “Malcolm, I have a proposal for you. The Physical Education master at St Mark’s came to see me recently. He is keen to improve team sports at the school and maybe even compete in the local school competitions, particularly football and cricket. He asked if we could employ an assistant PE teacher who specialized in these areas. I spoke to the Headmaster who gave his approval and I thought of you, Malcolm – would you be interested?

“Me?” Malcolm looked shocked.

“Yes, you,” said Rodney. “This isn’t charity, Mal – you’d have to work hard and we’d expect results, but I think you are the right man for the job.”

Tears began to run down Mal’s cheeks. “I’d love to do it,” he said. Then his face fell. “But I’ve got nowhere to live now.”

“I’ve thought of that,” said Rodney. “There’s a small flat in the school grounds. It used to be occupied by the groundsman, but he left recently, so that would be part of your position too, and it would come with the job, rent free. How about it?”

“What can I say but – when do I start?” said Mal.

All that happened two years ago. Rodney and I got married last year and I am now the school nurse at St Mark’s. The Headmaster will retire at the end of the year and I think there is a very good chance that Rodney will step into the position. Mal settled into his job very well. This year, the football team were runners up in the local schools’ competition and the senior school cricket team made a good start in the local competition, winning four of eight matches and drawing two. We have great expectations for next year.

It's amazing to think that three lives have changed for the better and all because I offered a man who was down on his luck, something to eat.

And so ends my tale of love and redemption and all I can hope is that we all live happily ever after.

THE END

I would like to acknowledge the help of my dear friends Lucy and Charlotte who provided the seed that grew into my story. B.W.