I didn’t realise at the time how much a Halloween night out with my older sister Jenny when I was 13 years old would affect my life and would come back to haunt me many years later.

I was quietly lying in my bedroom playing war games on my laptop when Jenny burst into my room, without knocking on the door first as she normally would.

“What are you doing tonight Jack, have you anything planned, or are you just going to sit there playing games on your computer?”

“That’s exactly what I am going to do Jen. All my friends are doing things with their families and mum won’t let me go out on my own.”

“I’m going trick-or-treating with Susie, Linda and Babs, why not come out with us?”

“As if they would want me tagging along, I’d just get in the way, and I’m not sure that hanging out with a bunch of giggly girls is my idea of fun. Besides, I haven’t got a costume.”

“I’ve got a few costumes that I have worn for Halloween over the years. They are far too small for me now, but should fit you ok.”

“ I’ll look stupid in any of the costumes I’ve seen you in.

“At least give it a try, we might find one you like.”

After trying on a few costumes, princess, Snow White, fairy, even Wonder Woman, we decided that the least girly outfit was one for Peter Pan. Even though Peter Pan was a boy, the costume was still obviously more for a girl than for a boy with a belted tunic top with scalloped hem which looked more like a short dress, especially when worn over the green tights, and a pair of her old shoes with a raised heel and big shiny buckles. I looked at myself in the mirror and was shocked at what I saw.

“I’m not sure about this, I look like a girl, what if somebody sees me and recognises me?”

“A lot of men and boys wear female costumes for Halloween, it’s not unusual and I’m sure nobody will think anything of it. If it really bothers you I can brush your hair back and hold it with a couple of slides and add a fall at the back, just like my ponytail. A little bit of glitter make up and some lipstick and you’ll look just like the rest of us girls.”

“Oh, alright then, you’ve disrupted my game anyway and I’ve now dropped back a level and am not in the mood to catch up again, do your worst with me.”

As she had suggested, my hair was soon restyled, and light makeup applied.

“Wow Jen, this might work ok, I don’t know what you think, but I reckon that nobody will recognise me or take me for a boy. This could be fun.”

“Come on , we are late, let’s go to meet the others.”

After getting a few funny looks and jokey comments from mum and dad, we went out to meet up with the her friends.

“Oh, don’t you look cute Jack Carter, or maybe it should be Jane for tonight.” Joked Babs giving me a hug, “You should come out with us more often.”

“Just for tonight you are one of the girls with us, you'll get an equal share of any of the treats we get, and then you can come back to mine afterwards for a bit of a party to share it all out with us.” Susie added.

“As Babs said, for tonight you are Jane, that's who we will tell everybody you are, but you will have to behave just like the rest of us, we don’t want anyone finding out who you really are.” Linda reminded me, and I agreed with everything she said, I didn’t want to be found out either.

I really enjoyed being out with the girls, and had a lot of fun. After the initial joking and giggling they treated me as if I was really Jane, just like any of their other friends. We had a lot of fun going around the neighbourhood, most people just gave us sweets, but some who were having parties of their own invited us in for a drink and some cake. Even indoors I was not recognised and I just relaxed and acted like the others.

Back at Linda’s afterwards they all decided to ditch their costumes and change into some ordinary clothes that Linda dug out for them. As I was watching them changing, seemingly they had forgotten that I was a boy and undressed down to their undies in front of me, Linda threw a bundle of clothes at me.

“Come on Jane, you too, you can’t sit there in your Peter Pan costume all night. Get changed or we will come and do it for you.”

I looked at the clothes that she had picked out for me, unsure what to do, I didn't know whether she was deliberately trying to embarrass me or whether she was just looking on me as another of the girls. but decided that if that is what would keep them happy l’d put on the tartan mini kilt, embroidered blouse and white ankle socks to blend in with them.

After a lot of chatter and giggling about the photos Babs had taken on her phone while we were out in our costumes and eating all the treats we had been given, it was soon time to go home.

“Ok Jack, pick up your costume and we’ll get off home and tell mum and dad everything we have been up to.”

“What? You can't expect me to go home like this Jen, what will Mum and dad think?”

“Don't be silly, half the neighbourhood has seen you dressed as a girl and we had a lot of comments about how cute we all looked, including you, what is wrong with mum and dad seeing you too.”

I warily made my way home with her, trying to avoid eye contact with anyone we passed and was glad to get back into the house, that is until I saw the look of shock on Dad's face.

“Its about time you were back home Jenny, and what on earth have you been doing with Jack.”

“It’s ok Dad,” I jumped in to defend Jenny, “we’ve had a load of fun tonight and it was a good laugh being out with Jenny and her friends with everyone thinking that I was just another one of the girls. I'll go up and get changed and then we can tell you all about it.”

“You don’t get away that easily, you can stay as you are until bedtime, now come in and tell your mum and me everything.”

Things went back to normal for the next week, but on the following Friday at school I started to notice people giving me funny looks and sniggering or giggling when I passed by. Nobody said anything to me, but it was obvious that something was up.

I normally walked home from school with my best friends Harry, Bob and Darren, and on Fridays we usually stopped off at the games arcade for a while. After I had waited at the school gate for them for a quarter of an hour, I realised that they had left without me and I just went home feeling confused as if I had done something to annoy them.

As I went in Mum was glaring at Jenny, obviously in the middle of an argument, Jenny just looked at me with tears in her eyes.

“ I'm so sorry Jack. “ she sobbed.

“What's up Jen, what have you done?”

“Babs left her phone unlocked lying on her desk when she left the room at morning break. When she came back a few of the lads and girls were all looking at the photos on it from Halloween and somebody recognised you all dressed up. Soon the photos of you had been passed around on social media and half the school had seen them. There are a lot of sarcastic comments and name-calling on all the chatline groups, you are the big joke in the school at the moment. That’s why your friends are giving you the cold-shoulder and there is a lot of giggling when you are around.”

“What’s the big deal everyone dresses up at Halloween, and I'm sure that I was not the only boy wearing a girl's outfit. Anyway it was only a tunic and tights, it's not as if I was wearing a dress or anything.”

“That's the problem, a couple of the photos and videos were of you back at Susie's wearing the skirt and blouse and with the fall still pinned to your hair like a pony tail. You seemed to be enjoying yourself and you looked ever so girly.”

“Stop worrying about it, there will soon be something else for them to gossip about and someone else to pick on.”

“The other problem is that I heard some of the girls really having a bitching session about you, calling you all sorts of horrible names, tranny, fairy, pervert and things like that. I had a real shout and scream at them telling them not to be so nasty and it turned into a bit of a cat-fight. I was sent home to cool off by the principal and was told that I might even be suspended.”

“Thanks for sticking up for me. I don’t say this very often, but you are a super big sister, come and give me a hug and we’ll get through this together.”

Over the weekend the girls came round to check that Jenny and I were ok and all promised to try to dampen down the worst of the nastiness. They invited me to hang out with them, but mum thought that wouldn’t be a good idea as it would only give an impression that I wanted to be like them, with them.

Whilst nobody actually made comments to my face, it was obvious from then on that I was being treated as a social outcast. The lads were no longer walking home with me, there were no more invitations to visits to the games arcade, and in class none of the boys wanted to sit next to me or be my ‘buddy’ in the science labs or craft workshops A couple of times when I came out of the shower after Gym, I found that my underpants had been replaced with girls’ knickers which I just put on without any comment, not wanting to give them the satisfaction of arguing or appearing embarrassed. Apart from those occasions, I was generally being ignored by all the boys, although some of the girls were quite happy to talk to me and let me sit with them at lunchtime.

The only one of my old friends that stuck by me at all was Darren, who I had known since nursery school. He was one of the most popular boys in the school, well thought of by the other boys, and beginning to get noticed by the girls and was well able to cope with any comments about being friends with the school weirdo. He often joined me when I hung out with the girls and quite enjoyed the attention he was getting from them.

Over the rest of my time at school, I just kept myself apart from the rest of my classmates and learned to just accept that I would never overcome the reputation of being a tranny freak. It wasn’t helped by the fact that when all my classmates were growing and putting on weight and muscles, that I stayed short and skinny. I thought to myself that Halloween had just been a one off event for me and that I had no intention of dressing in a skirt again, but other than Darren, Jenny, and her friends nobody wanted to believe it.

It turned out that they were all right after all. Life went on as normal for a while until the next Halloween.

“What are you doing this year Jack, do you want to come out with me and the girls again as it looks like all your old boy buddies don’t want to know you, and you can’t just stay in and be miserable? We are all dressing as St Trinian’s schoolgirls, short skirts, our bras padded out, ,black stockings and suspenders, over-the-top makeup, you know the type of thing. ”

“Don’t you think that there was enough damage done last year, if I went out with you like that, any hope I have of getting my reputation back will be totally lost?”

“You know as well as I do what people think of you already, it wouldn’t make any difference. By the time we are finished dressing you and making you up, nobody will recognise you anyway, there will be no way that you will be seen as anything other than just another one of the girls.”

“Will the girls be ok with it, I don’t want any sarcastic comments from any of them?”

“ This was not my idea, Linda suggested it, and the others thought it a great idea, honestly, you will be more than welcome, and you did enjoy yourself last year.”

“ Ok, but first check with Mum and Dad to make sure that they can live with it, and if I do this, there are definitely to be no more photos of me.”

Mum and particularly dad were not too sure about me dressing again, but in the end decided that it was harmless fun, agreed to it, and in some ways they were looking forward to seeing how good a job the girls made of me.

All afternoon, I was taken over by Jenny and her friends to transform me into a sexy schoolgirl. My naturally curly hair was straightened and cut into a fringed bob, what little facial hair I had was shaved off before being covered in a gooey face mask, and then being overdone with foundation, blusher, heavy eye make up, and bright red lipstick to match my newly cleaned and shaped fingernails.

The girls had decided to wear their school uniform blazers with St Trinian’s badges added to the breast pockets, blouses and ties but skirts that short would never have been allowed in school. With the others out of the room, I was totally stripped by Jenny, squeezed into an extremely tight pair of plain knickers which kept me tucked in place, over which their was another pair of black lacy ones which she told me would show. occasionally under the short skirt she then handed me, which only came down to mid thigh and barely covered the knickers. The others then came back in wearing their costumes and took great delight in seeing me fitted with a black lace bra which they stuffed with bags of rice to give me what they said was a full C cup shape which seemed to want to burst out of the white blouse I was given.

They hadn’t been too over the top with me, I was probably the most demurely dressed of all of us. Again, I had a great night with the girls. As promised there was only one photo of the group with me in it, which was taken on my phone for me as a memento, although, I took lots of pictures of the other girls.

After going around the houses trick-or-treating, we all went to a local coffee bar to chat about our night , what treats we had been given and the reaction we had got from people. We were just about to leave when a group off lads came in, took one look at us and made a beeline for our table. Luckily they were not from our school and didn’t know any of us, but I was still uncomfortable and worried about being unmasked, The girls however were enjoying the attention they were getting and we stayed a while before getting up to go.

“ I need to go to the washroom.” I whispered to Linda.

“ Me too,” she quickly said, “come with me, the girls room is just over there in the corner.”

“ I can’t go in there with you.”

“ Don’t be silly, you certainly can’t go in the boys’ room looking like that, you will never get out alive or at least intact, if you need to go you have no choice it’s only a washroom after all, what difference does it make whether it’s for girls or boys”

Last year I hadn’t had to face this problem, but the drinks we had been given on our tour of the estate and the coffee we had just drunk gave me no choice and I warily followed her in.

After a quick look around to make sure the room was empty, she pushed me into an empty cubicle. “Go on and do your business, as far as anyone else is concerned you are no different to us other girls, but don’t forget to sit, wipe yourself afterwards and tuck yourself back in place, just in case one of the lads tries it on and goes for a feel.” Thinking to myself that there could be no way that I could allow that to happen I did what I had to do and left the cubicle to find her touching up her lipstick and fluffing her hair in front of a mirror.

“Don’t forget your lips, the way the lads were looking at us we will be lucky to get out without a kiss and a grope from them.’ I was a bit shocked that she was so open with me, almost talking to me as if I was really a girl. Jenny had put a lipstick and mascara in the pocket of my blazer, and I quickly did a swipe of both as it was obvious that it would be expected of me.

In a way I was lucky that Linda had forewarned me what to expect, as she was right, there was no way we could get past the lads to leave without a ‘nice to have met you’ hug and kiss from them all, including one whose hand drifted up my thigh, but he was quickly pushed away and put in his place.
“
Leaving the café we made our way home, arms linked, skipping and giggling, wished each other goodnight with hugs and cheek kisses, and Jenny and I entered our house to find Mum and Dad waiting expectedly to see how I looked.

“Wow Jack, or should that be Jane, you look amazing, did everything go ok?” Mum asked first, she looked to be ok with me, but dd rolled his eyes and looked away.

“Jane was fantastic , she really fitted in with the rest of us girls, she even had a hug and kiss from a group of lads in the coffee bar.” Which caused a bit of a worried frown from dad.

“Tomorrow all of us are going into school in our costumes like everyone else will be doing, but obviously Jane can’t do that and will have to go back to being stay-at-home boring Jack, shame really, she could easily get away with it, if only people were not so nasty since last year.”

Jenny and I went up to get changed for bed and to to clean off our makeup, and whilst it felt good to get out of the tight restrictive knickers, unhook the bra and lose the weight from my chest there was a tinge of regret that I could not wear my costume for school tomorrow.

Some people at school asked why I was not in costume, but I just replied that I had stayed at home as I didn’t celebrate halloween anymore after what happened the previous year, and I privately enjoyed my memories.

Despite many offers from the girls to go out with them as Jane, I steadfastly politely refused, and while I looked forward to joining them again at the next Halloween, anything more did not not seem a good idea.

There were two more years of being Jane at Halloween with Jenny and the girls, but they being two years older than me then started seriously dating and they all started doing things with their boyfriends, and so Jane was soon a distant memory.

I was glad to leave school and head off to university to study journalism and creative writing, happily looking forward to a normal social life with a wider circle of friends, forgetting all the bitterness and unpleasantness that had followed me through school. The only good thing that had come out of it all was that, having no choice but to spend a lot of time with Jenny and her friends, I was very comfortable in their company and was able to mix easily with new friends of both genders at university.

Throughout my first year there my life was more enjoyable than it had been for many years and my more relaxed frame of mind showed in the high grades I had achieved, life was beginning to look good again.

Things changed however at the start of my second year there when a few new people arrived from my old school and started spreading all the rumours about that Halloween many years before. I suddenly found that most of my new friends started being cool towards me, although it was not quite as bad as it had been at school. I also suddenly found that I was getting approaches from the LGBTQ society and its members suggesting that I get involved in their activities, but I politely but firmly told them that it was not my scene and that, despite all the rumours, I was totally ‘straight’ and heterosexual. The sudden curtailment of my social life I had been enjoying meant that I just threw all my time and attention into my studies and over the next three years I managed to graduate with a first-class BA, followed by an MA, and was looking forward to leaving academia and entering the frenetic world of journalism.

I returned to my home town and moved back in with my parents, although Jenny had now moved out into a flat nearer to her work. With the high-grade qualifications I had achieved, I had no problems getting a position as a reporter on a major regional newspaper, the Daily Post, and settled down to my new career. However my dreams of cutting-edge investigative journalism in the manner of Bob Woodward and Carl Bernstein were soon shattered. My new reality as the junior reporter was covering social events, weddings, fund-raising campaigns, small crimes, and local sports clubs, which although giving me a good grounding in how newspapers operate, was not the most stimulating and challenging use of my time and education.

Things were soon to change however when I received an unexpected call from my old school friend Darren Cartwright, who had been the only male to keep in contact with me from the old days.

After all the pleasantries and catch-up were finished, Darren changed his tone and cut to the point of his call.

“Are you still looking for that big story to kick-start your journalism career?”

“That’s a nice thought but I’m not getting anywhere near something like that, I am still stuck with a load of mundane day-to-day stuff.”

“I might have something that will help you, help me, and could lead to a big story. Are you interested?”

“Tell me more.” Although I had no idea of what he wanted he had sparked my interest.

“Not over the phone, let's meet for dinner tonight and I will tell you a bit more.”

We met up later in a local pub and had a pleasant meal and a chat about old times, before we left our table and found a quiet corner in the lounge where he felt more free to tell me what this was all about over a pot of coffee.

To be continued.