A Boy Called Gillian

by Gillian Ogilvie

Part 1

 

I was a second child with an elder brother five years older than me, so when I was due to be born my dear mother was very keen to have a little girl and thus make a "pigeon pair". She had bought lots of pink clothes and had even decided that the baby would be named "Gillian".

Lo and behold in September 1933 little Michael arrived! What a disappointment this must have been! However, in spite of the initial disappointment I was brought up as a perfectly normal little boy with loving parents and a caring elder brother who taught me much of what I know about life and how to live it.

We lived in the heart of the sheep-farming area and in 1939 the Wool

Board decided to have a slap-up dinner dance, no doubt to celebrate a record wool clip. It was decided that a grand Ball would beheld at which a "Wool Queen" would be chosen and crowned. My father was chairman of the organising committee and my mother was involved in making the crowning ceremony as brilliant as possible. The crown was to be carried on a blue velvet cushion by a pageboy and I was selected to carry out this important function.

The ball was scheduled for the night of 16 August 1939 at which time I would be nearly six years old. In due course my page outfit was designed by a Mrs Green, a local dressmaker, and I was taken for the first fitting. Mrs Green's son Bernard was unfortunately present, which worried me as he was an oafish lad and stood grinning at me during the fitting in a way that clearly indicated that he thought I was a terrible sissy!

My costume comprised a little red velvet tunic, red satin pants, white stockings and a white satin shirt with lace at the wrists. I can still vividly remember the feelings that shot through me when I first tried on the clothes at that first fitting. The feel of the satin pants was stupendous and the fact that they had no "fly" and had elastic round the legs convinced me that they were girls panties. The feel of the red velvet tunic was also wonderful and of course wearing white stockings for the first time, with suspenders fixed to my shirt, was for some strange reason most enjoyable. My reaction to this delirious bouquet of feelings was strangely to throw a complete tantrum and stamp my feet, which were very attractive in black patent leather shoes with large gold buckles. Bernard then capped it all by saying that I looked like a little girlie! He was sent out of the room and I was pacified by my doting mother.

The great day dawned and I was bathed and my hair washed in some special shampoo to make it lighter and shinier. I was made up with rouge and a touch of lipstick and the exciting costume was carefully put on! Everyone said I looked pretty good and the newspaper described me as "an adorable little page boy in a red velvet costume".

As I walked into the town hall one of my brother's friends said in a loud whisper " you look like a girl!" I was angry, but somehow delighted, at this second comment regarding my girlish look!

And so the Wool Queen Ball encouraged the strong seed of my feminine side, which I am convinced was there from birth and was to grow over the years.

The following year I went to school for the first time. It was a co-ed school so I had my first brush with schoolgirls in their navy blue school uniforms, which consisted of gymslips, white shirts, and blue "sateen" panties to match. Short white socks and single strap black shoes completed the picture. I was entranced by those wonderful garments and whenever one of the girls bent over to pick something up I enjoyed a glimpse of smooth silky panties (sateen was a sort of soft shiny cotton material rather like my favourite satin.) I often wondered what it must feel like to wear such delicious garments and was desperately envious of the girls who were so lucky! I actively disliked my rough, drab, boring grey flannel shorts and even refused to wear underpants because I didn't like having a Y-front!

It is interesting that at this stage of my life I was unaware that there were any physical differences between girls and boys and couldn't understand why girls were dressed differently!

About a year later when scratching through a jumble drawer I came across the red satin pants. I immediately thought of the school uniforms and the urge to put them on was completely overpowering. I nipped into the toilet, took off my trousers and with shaking hands drew on the satin wonders, which by this time were pretty tight, as I had grown somewhat since the ball. What a feeling! I pulled on my trousers over the satin pants and went walking about the house with my heart beating madly but feeling like a million dollars..........a cross dresser at age seven?!

On many occasions I wore my red satin "panties" under my grey flannel trousers and revelled in the slippery feel and the knowledge that I had a secret, which nobody knew about! Eventually the pants couldn't stand the strain and split from top to bottom! I was devastated but all I could do was consign them to the garbage can.

My fascination with girls and the clothes they wore at prep school continued until I started at the exclusively boys college at the age of nine, but then a new influence began.

My mother was a professional musician and decided that I should learn the violin. As there were no violin teachers at the boys' school it was decided that I should learn at the Girls High School, known simply as GHS. The music rooms were in the main girls' hostel, which housed over a hundred boarders from standard 3 to matric. Twice weekly in the afternoon I would enter this holy of holys to have my music lesson. The place was packed with girls heading out to play tennis in their short white tennis skirts and to play hockey or whatever. Some were simply relaxing on the lawns with their gym skirts pulled back to get the maximum of sun on the lovely long legs. The senior girls wore long black stockings during the winter and many a suspender did I see as school-bags were being picked up!.....all very strange and exciting to a young lad like myself, but I loved it!

At age twelve I had become a good violinist and I was allowed to play in the GHS orchestra and became an indispensable member with many good friends among the girls who accepted me as part of the team. I was very much the envy of my school friends and often played postman taking love letters back and forth between the two schools. The GHS orchestra was where my first cross-dress story actually began.

When the end of year prize-giving came up, the head mistress refused to let me play in the orchestra as she felt it was not right for a boy to be in the girl's orchestra. My teacher was furious and phoned my mum who was equally angry. "We should dress him up as a girl then no one would know" said my mother half joking. My music teacher being a lady of quick brain said: "well why not?"

After much discussion the head was consulted and she agreed on condition the "girl" was absolutely authentic and indistinguishable from any of the real girls in the orchestra. I was duly told of the plan and needless to say flatly refused, on principle, but was inwardly beside myself with delight! I knew I could pull it off, as I was at that time slight of build, fairly short, and fair with pink cheeks and fine features. I had not yet developed a beard, which was to help matters, and my voice had not "broken" and was still a sweet girlish treble.

Two days later was Friday and when I returned from school my Mum called me to her bedroom and there on the bed laid out were the most exiting garments I had ever seen: A navy blue gym dress, a white shirt with long sleeves, a suspender belt, a pair of sateen panties with elastic top and bottom, a pair of long black stockings, a pair of girls' black school shoes and a red and white GHS school tie.

I must point out that in those days there were no panty-hose, hence the suspenders. I had sometimes caught a glimpse of these mysterious items of female clothing but now I was to actually find out how they functioned.

My mum told me to take off all of my clothes and then came the exiting part. First I put on the suspender belt which was quite tricky but Ma helped. Then a thrilling bit when I was shown how to roll up the stockings and carefully pull them up over my legs and clip them onto the little metal and rubber clips at the ends of the four elastic suspenders attached to the suspender belt. After turning the sateen panties round so that the leg holes faced to the front I pulled them up over the stockings until the waist elastic was firmly around my waist. The stockings were not quite long enough and two "gaps" of white thigh appeared at the top of the stocking tops. Next came my white shirt which was just the right length to tuck into my panties.

At this stage mum told me to walk across the room to "get the feel of the stockings etc. What a feeling that was! The suspenders tugged at my stockings as I walked, and the stockings rubbed together with the sexiest swish-swish. The gym slip was next and this was also a great feel as it fell round my waist. When zipped up at the side and with the belt buttoned, the firm tightness was most exiting

Lastly the tie and shoes were put on. The latter made me bend down and I relished the feel of pants and suspenders pulling tight as I bent down! "You must be careful never to show your panties," said my mum "So always keep knees together and bend them rather than bending down".

My hair was fairly long which was the fashion, so mum was able to make two bunches and tie on two blue satin ribbons to complete the girlish look. I was then taken in front of the full-length mirror to see myself and I nearly burst with ecstasy at this pretty little girl standing in front of me. I had really never felt so excited inside me as when I saw myself as a little schoolgirl.........I guess my years of wondering "how it felt to wear girls clothes" were now being resolved.

My Mum suggested that, as she had to go to town to buy some milk, I should go with her and get used to my new gender eg walking with neat steps and not great strides like a boy. I walked down the stairs from my Mother's room in a cloud of ecstasy, and then outside where a cool breeze was blowing. What a feeling to have the breeze play about my legs and touch the gaps at the top where stockings and panties met! Sitting on the leather car seat was also nice as the leather was cold on the gaps.

In town I was sent into the cafe to buy the milk and so I stepped out of the car and tugged my skirt down at the back as I had seen girls do. As I walked the few steps along the pavement I glanced into the shop windows and saw the reflection of this pretty little schoolgirl walking along the street. Wow! what a gas!

In the cafe I was shaking like a leaf as it suddenly dawned on me that I was a girl and thrill of all thrills as the shopkeeper handed me the milk he said: "There you are my girl, good- bye." My Girl! I could have died with bliss! Heart beating I ran back to tell my Mum, who was most amused and said "well you are a very pretty girl". I thought I would burst with joy and settled back in the seat to enjoy my new good fortune. I had settled into the new role so easily that I really was enjoying myself immensely.

The evening was by no means finished yet as my mum announced that on the way home she had to collect some papers from her friend Mrs Johnson. Now Mrs Johnson had two children; a boy Brian who was fourteen and a girl called Joan who was my age, played violin in the GHS orchestra and was sort of my girl friend. I thought nothing of it as I could sit in the car and wait while mum went into the house.

When we arrived all was well until to my horror Joan came out to the car to say hi! Fortunately mum had explained the situation to Joan and her mother so Joan wasn't at all surprised to find her boy friend dressed in a girls school uniform! She asked me to come in and see her new violin bow so I climbed carefully out of the car and walked into the house. Here I met Mrs Johnson who gave me a hug and said that I made a gorgeous girl.

Joan was still in her school uniform but she had been playing hockey and was wearing short white socks instead of long black stockings. "Why don't you change into socks?" asked Joan. "I will lend you some and you will be so much more comfortable" I agreed and we went into Joan's bedroom which was normally a forbidden area. I was rather embarrassed but Joan soon put me at my ease and assisted me to unclip my stockings and take off my suspender belt. I had to take my shoes off and then replace the stockings with neat white cotton socks.

With shoes back on I was able to enjoy some delicious new feelings of bare legs touching the hem of my gymslip and of cool air playing around bare legs. I also found it exciting to be there with Joan dressed exactly the same as me, as I was able to watch how she moved and sat and took her hanky out of the leg of her panties to wipe her nose!

"I like you much better as a girl, Mike" said Joan "and I am going to call you Gillian .......will you be my best friend?" I gave her a hug and said I would like that. (I enjoyed hugging Joan as it seemed exciting somehow for two girls to hug) Then to my great joy Joan gave me a little kiss right on the mouth, which was even more exciting.

My mother called us and the magic moment was gone but then as we walked out who should arrive but Joan's brother Brian. He smiled at me and said "hi" but obviously thought I was one of Joan's school friends. As we climbed into the car I heard him say to his mother "Wow, who was that gorgeous babe?!" I immediately fell in love with Brian!

The next thing was Mrs Johnson saying to Joan " Why don't you ask Gillian to go to the rugby to-morrow afternoon?" "She will need as much experience as possible if she is to pull off being a girl at the prize giving concert" So in no time my weekend was arranged: Town with Joan and Brian to drink milkshakes, then college rugby in the afternoon and a party in the evening. And to cap it all, tennis on Sunday at the Johnson's house.

As we drove home I was wondering where Gillian would get the correct clothes to attend all those functions. My mum however said that Mrs Johnson would sort it all out. Joan was the same size as me and would lend me all the necessary clothes.

That night after doing my homework, still dressed in GHS uniform, I said goodnight to my parents and reluctantly took off my precious uniform and went to bed. I dreamed about kissing Joan....... in our school uniforms!

  

  

  

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