A Boy Called Gillian

by Gillian Ogilvie

 

PART 5

 

I was looking forward to the Carol service and often had a peep at the gorgeous satin creation that I was to wear. However more excitement was on the horizon!

One day it was announced at my school that a Christmas Variety Concert would be held at the end of the year in the last week of school. Each senior school class was to provide an item and a prize would be given to the best item. There would also be some special items involving people from a few classes. Under this heading a gymnastic display would be given by the "Specialist Gym Team". I was a member of this team and was very excited at the prospect.

Then came the bombshell announcement that, to add a bit of spice and fun to the item, the gym team would wear GHS school uniforms! The mind boggled at the thought of doing a handstand in a gym tunic with black stockings and suspenders exposed! The news was met with very mixed feelings by the team, a few of which were big rugby players and not interested in anything "sissy". There was no getting out of it and we were told to borrow the necessary items of clothing from girlfriends etc. Gym tunic, panties, suspender belts and black stockings were mandatory and we would use our own gym shoes. I of course had no problem as I already had the entire outfit in my cupboard at home.

One of the boys in my class fancied himself as a playwright and wrote a play called " Le Café de Rot Mort" which he said meant The Café of the Dead Rat! This was to be our item and the cast comprised two Chicago type gangsters and a sweet young couple who were caught in a crime scene. The boy and his innocent girlfriend were to be involved in a bank robbery against their wills and police were to raid the café. The rest of the class was either cops or thugs. Naturally I was chosen to be the girlfriend due to my baby face and small build, so I had to prevail on my dear mum to make me an appropriate dress. We discussed the dress and decided that an innocent young girl would wear a flared dress with lots of petticoats. Mum had a taffeta dress and petticoats, which with slight alteration fitted perfectly. She borrowed a beautiful brown wig and size eight high heel court shoes and I produced the rest of the clothes to turn me into this gorgeous young girl.

The carol service was to be on Saturday and the Variety concert was on the following Friday and Saturday nights, so I had to attend two lots of dress rehearsals and three performances in my girlie clothes! I was over the moon with excitement and at last the first dress rehearsal arrived: the carol service.

This was an evening rehearsal and mum helped me dress and did my makeup at home before driving me to the Town Hall where the service was to be held.

The orchestra was all in white satin and the choir was in pink satin. The whole effect with the spotlights on was quite stunning and made me want to cry it was so beautiful. (What a sissy, but girls are allowed to cry when they're happy!)

Sitting down was interesting as my satin dress pulled tight across my legs and felt so nice. I noted that all the other girls in the orchestra had the same tightness across their legs and my young man started to stiffen accordingly! We played well and the singing as angelic. Eventually we all trooped out to waiting cars. It was amazingly difficult to step down the curb in my dress and getting into the car was equally difficult. I eventually pulled my dress up to my knees and got blasted by mum for being unladylike! I guess that there was still some boy left in me!

That night the little white angel had a very wet dream in which he was kissing a little pink angel. Nothing like satin rubbing together to give you dreams!

The next dress rehearsal was the Variety Concert, which was also held in the Town Hall. My first curtain call was for the play so I got dressed and made up at home. The pink floral dress had "puff" sleeves, a tight waist and a circular skirt. I wore beach bronze nylon stockings and white shoes with heels. The petticoat was superb, layers and layers of pink and white lace and tulle, which rustled with the taffeta dress and felt wonderful around my legs especially with the stockings swishing when my legs rubbed together as I walked. The wig was shoulder length with a fringe across my forehead. This and good makeup made me look very pretty and innocent. When I looked in the mirror I had some trouble with a stiff person fighting against my tight satin panties. Oh! How I loved dressing in these lovely clothes!

When I walked into the hall not one person recognised me, but all were full of praise when they realised who it was. The play went off well and was very funny in parts especially when a gangster pulled out a gun to threaten my boyfriend and I squirted him with a soda siphon! The best part was when the police arrested all the gangsters and my boyfriend and I were left alone to have a long lingering kiss. We kissed on cheeks not lips but from the audience it looked like lips!. Little did I know what would happen on the last night!

I had my gym clothes in a small suitcase so I was able to change backstage for the gym display. When I walked into the change room where all the gymnasts were changing they thought it was some girl that had got lost and there was a mad grab for things to cover their privates! I responded by lifting my skirts and flashing my panties at them. Some of them were battling to put on their suspender belts and stockings, so I was able to help them before donning my own uniform. I noticed that a number of the team had "hard-ons" from putting on girlie clothes! The tight navy school nickers soon sorted that out.

I shed my wig and carefully folded it into itself and into its box.

It was so nice to be in my favorite uniform again but we had to face the problems of doing gym in skirts. The very first vault was over the "horse" and as I was the smallest and therefore the first to come over the horse my gym skirt hooked on the pommels and I was suspended in mid air! We decided that I would do this on purpose at the show and two guys would lift me off! Later my slow pull up to a handstand on the horse was fairly revealing as my legs went up and my skirt went down showing panties, suspenders, gaps and stockings! We all did somersaults with a huge flurry of skirts. The finale was a pyramid with all the "girls" standing on each other's shoulders and a junior in boy's uniform climbing to the top to hug one of the "girls". The pyramid then slowly collapsed. This event was going to be a hit. After the rehearsal I noticed a definite reluctance among the gym team to shed their uniforms. They all minced about drinking cool drinks, wiggling their hips and being limp wristed. At the end of the rehearsal they went home still dressed in their gym tunics. They obviously loved dressing up for the performance! Clearly a large percentage of men would love to dress but are prevented by deep-rooted pressure from parents and peers. If these pressures are lifted they have a ball for as long as possible! (They would, of course, never admit this to anyone!)

During all this time I allowed my hair to grow as long as the school rules would allow which was down to collar level. Just before the carol service my mum suggested that I should have a more feminine hairstyle so she made an appointment with her hairdresser. On the appointed day I was taken to the hairdresser and seated in a special chair to have my hair washed. I was very excited by being surrounded by women and girls all being made pretty. The whole place was full of the wonderful perfumes of the shampoos, setting lotions and so on that gave me that old excited feeling in my tummy.

It was decided that I should have "curls and some bangs". I didn't take much notice of the decision but started to wonder what I would look like at the end of the process. My hair was put into rollers and coated with setting lotion, after which a hair net was placed over the rollers to hold them in place and that made me feel very girlish. Later I was put under a dryer which blew hot air over my head and I guess made the curls permanent. It was very exciting but the best was when the process was complete and I was allowed to look in the mirror. I really did look girlish even though I was wearing boy's clothes. I was a bit panic-stricken thinking about school and what my friends would think, but it was too late, there was no going back!

While we were at the hairdresser my mum suggested that to really complete the "makeover" I should have my ear lobes pierced. I really wasn't mad about this but went along with it out of interest and after all I did love all girlish things! This procedure was done by the hairdresser and was quite easy although it stung for a few minutes when the studs were inserted. Then as we were about to leave mum looked at my finger nails and decided that they should be manicured, so down I sat and the manicurist got to work. She was a young trainee, very sweet and careful not to hurt me. After the cuticles had been trimmed and the nails had been shaped, a lick of clear varnish was painted on. Finally some nice hand cream was smoothed on and rubbed in. My hands felt super and I walked out of the shop on a cloud.

I had been so good that mum asked me if there was something that I would like as a little reward. We were just passing a lady's outfitter and in the window was a gorgeous pink satin "baby doll" nightie. I pointed at it and as a joke said "How about that?" To my utter surprise my mum said "Oh that's a great idea, I would love to buy that for you!" So into the shop we trooped and fortunately I wasn't asked to try it on as mum could estimate the size. The shop assistant took a box from the shelves and we set off for home with the box in a big packet.

At home mum gave me the packet and said "There you are my love, I hope you enjoy wearing it! You must try it on and make sure the size is right." I dashed up to my bedroom, locked the door, and with a wildly beating heart opened the box. I had assumed that the nightie was just a nightie but I discovered that there was also a pair of matching satin panties with some lace around the legs. I quickly stripped off my clothes, shoes and socks and pulled on the panties. The feel of the satin gave me the usual hard on but when I slipped the nightie over my head I just couldn't believe how feminine I felt.

The nightie came to just above my knees and in the mirror with my new curly hair and studs I looked simply stunning! I had a secret lipstick and put some on to enhance the image just as my mum knocked on the door. I let her in and she just gasped. "You really should have been a girl!" she smiled giving me a hug. "I would have liked that." said I with feeling. "Would you really?" Mum asked. I just blushed, smiled and said, "Yes I would!" No more was said but mum looked very thoughtful. I couldn't help wondering what she was thinking, but it would be some time before I was to find out.

That evening when supper was finished I said I was very tired and would like an early night. Dad was asleep in his favourite armchair so mum gave me a knowing smile and kissed me goodnight. I had a nice bath with some of mum's fragrant bubble bath, and needless to say put on the new "baby doll"! In bed it felt wonderful when I moved or turned over and I was soon fast asleep. I had the most wonderful wet dream in which I was dancing in my nightie with the manicure girl who had done my nails! It was great but of course I had to rinse the panties in the morning to get rid of the white stains.

The day of the Carol Service dawned and I kept having that wonderful excited sort of butterflies feeling in my tummy. I decided to do some practicing as the music was quite hard. While I was hard at work Mum came in and suggested that I should wear a dress round the house just to get really used to moving like a real girl. She had been to town and bought me a layered Spanish style pink floral skirt and a pretty matching blouse with puff sleeves. I was also given a pair of sandals with slight heels and delicate white straps. Finally a pair of pink satin panties and a satin slip were handed to me. In no time I was transformed into a gorgeous young girl with curly hair. I had lunch dressed like that and reveled in the feel of those clothes on my smooth bare legs.

After lunch I went back to practicing my violin but this time I went to my bedroom where I could see myself in the big mirror. What a vain young lady! I wore my bra and breastforms which of course added to the feminine feelings rushing through my body. After a half our I needed to go to the toilet to wee. I hadn't tried this before and it was such fun to pull my panties down among the froth of petticoats and skirt. It was surprisingly difficult to keep all this from going into the pan when I sat down but eventually I succeeded an managed to push my Willie down between my legs and wee like a real girl, straight down!

After I was all back decent again I decided to go for a walk in the garden and smell the roses. I really felt like a girl and enjoyed the delicious feel of the cool breeze playing around my legs and lifting my skirt with cheeky little puffs. Back in my bedroom I took of my skirt, blouse and shoes and curled up on my bed for a nap. The next thing was my mum knocking on the door telling me that I must bath and get dressed for the Carols. My clothes were all beautifully ironed and laid out on the bed by my dear mummy by the time I had finished my bath and in ten minutes I was all ready to go. A last check of violin, music etc and I went out to the car where my Dad opened the door for me. I think he rather liked having a daughter to spoil although he never said much about it.

I think the biggest thrill of the carol service was when we walked onto the stage in our long white dresses. It was impossible not to walk in a feminine way, as the dress was fairly narrow at the bottom. The whole thing was a huge success and again the head mistress congratulated me on looking very pretty. Joan was also in the orchestra and we kept together for the tea party afterwards. Brian was in the audience and we met him after the performance. He looked so handsome and gave me a kiss on each cheek to say "well done". I really melted inside and wanted so much to kiss him properly but that would have to wait for later. There was no doubt in my mind that, whether I was dressed as a girl or a boy, I was in love with Brian.

The school concert went very well the following Friday and was especially exciting as the whole of GHS was present. On the Saturday night our kiss was somewhat different as my boyfriend kissed me full on the lips and the audience erupted with glee! Afterwards I found Brian very withdrawn and eventually I asked him what was the matter. He answered that he was jealous of the kiss my "boyfriend" had given me in the play. It seemed that Brian might be in love with me as well.

The answer came at a most unexpected time weeks later when I went to borrow a tennis racket from Brian one afternoon after school.

I was in my school uniform and Brian was in his. He was alone in the house and asked whether I would like a cold drink. I said yes and went with him into the kitchen to get the drinks. He handed me a drink and our hands touched which as usual was like an electric shock for me and he obviously felt it too. Then I nearly died of surprise because he have me a little kiss on the lips and said, "You know I really love you!" I was dumfounded for a few seconds then whispered "I love you too" Whereupon we put our arms around each other and hugged for a long time.

What followed will remain with me to my dying day! Brian kissed me and his tongue forced open my mouth to a full French kiss with our tongues intertwining and our lips locked together. Somehow the fact that we were two boys kissing deeply made it ten times as sexy as anything I had ever experienced…...

Looking back, I will always remember those heady days when I experienced tingles and tummy excitement from dressing in girls' clothes, but unfortunately over a fairly short time the hormones of "boy puberty" kicked in with a vengeance and with all the attendant changes! My voice dropped, I grew whiskers on my face and hair all over my body. My shoulders got broad and I grew fast until I was six foot two inches tall! In fact I lost all of my feminine looks and just could not look convincing in girly clothes, so all the cross-dressing stopped.

Life goes on and I later married a lovely girl and had thee beautiful daughters! I retained wonderful memories of my pre-teen escapades which I wouldn't have missed for anything. My mother and I never discussed the past but I often wonder what she had in mind for my future when I intimated that I would like to have been a girl. I do know that she adored her three granddaughters and used to spend much time making pretty dresses for them. Perhaps that compensated for not having her own daughter!

I believe in reincarnation, so maybe next time round I will be a lovely little Girl called Gillian. (Rather than A Boy called Gillian!) I would love that!

 

End of Story

  

  

  

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