I was being hassled to hurry up by my girlfriend, but I was not ready yet, not by a long way. How could I be, this was so odd, so out of the ordinary, how could I do it? The whole thing had sort of ‘snuck-up’ on me and I wasn’t ready, not by a long way. How could I be, after all I am a perfectly ordinary sixteen year old boy and it is not remotely normal for a perfectly normal boy to be going to school with his girlfriend, not when that school was an all girls school and I was expected to be, indeed had to be dressed as a girl. It was an invitation day, and each pupil had been asked to bring a friend to share a fun day, but the rules were strict and it had to be a girl friend, no boys were to be invited. So why was I expected to take part in this subterfuge? That I am afraid is a long story, so sit back and relax whilst I tell you how this all came about.
My name is David and these events happened many years ago when the world was a very different place from what we know today. In particular, in those days of the late 1950’s the sexual revolution had not yet even begun and my innocence and naivety would be difficult to understand today. I was an only child and had been brought up in a strict, sexually repressed and old-fashioned family where sex was just never discussed. My education had been in single sex schools since the age of eight and, as a result, had almost no knowledge or experience of the opposite sex. As a result the world of girls was a closed book to me (as indeed it was to many of my peers). Apart from a few grubby magazines that sometimes got passed around amongst the boys I had never seen a girl or a woman even partially unclothed, let alone naked. The censorship laws in those times meant that even the grubby pin-up magazines we could get hold of gave a very distorted idea of what a woman looked like; all evidence of her vagina and pubic hair was always airbrushed out. As a result most of us boys thought that impregnation must take place through the tummy button or the anus, which revolted us all. Add to this that, I was a late developer into puberty and at that time had no body hair, and a tiny, almost insignificant, penis and tiny testicles.
Thus, given this background, it is hard to explain about how the announcement about the school deciding to have a ‘school dance’ affected me and my friends. It had been decided by the governors and teachers of both our school and the nearby girls day school that it would help the pupils social development if there were to be supervised social activities between the two schools for the older pupils. As a first step an end of term dance had been proposed, discussed and organised, to take place in four weeks time. To ensure that we boys behaved properly, at least the fifth and sixth formers who would be attending, it was arranged that we would spend an hour each evening after prep learning how to behave and the rudiments of social dance. At that time this really meant the waltz and quickstep, with maybe a cha, cha, cha for those able. Certainly we were not to indulge in any ‘rock or roll’ style antics on pain of a detention at best and perhaps a caning (Still legal and widely practiced then) if we let the school down. These evening sessions told us how to behave toward young ladies, how to ask for a dance and some rudiments of proper etiquette. Principally, however, they were to teach us at least the basics of ballroom dancing. Inevitably, we had to, at times, accompany each other,/one of us taking the women’s part. Perhaps because of my small stature and slight build I seemed to do rather more of this than most, and this was to have repercussions in the future.
By the day of the dance we were all deemed to be ready to take part and we were all excused prep to allow us to get ready. At this time you wore a suit, or a smart blazer, a white shirt and a tie to any dance. At seven o'clock we made our way towards the big room (schoolhouse) where the dance was to be held. Scrubbed, suited and booted we awaited the girls, some of the older boys had already arranged to meet their girlfriends. Gradually our female guests started to arrive and we were all too soon starting to mingle shyly as we found seats around the dance floor. My friends and I sitting with a group of girls of a similar age making small talk as we got to know each other.
Once the music started it took a little time for things to get going, both the girls and us boys were inexperienced and it was some time before one or two braver souls got up to dance. I had fallen into conversation with a girl that I quite fancied and we seemed to be getting along well. Her name was Barbara and she was not only easy on the eye but also very pleasant to chat with. She was the one who suggested that maybe we should dance as it would provide an excuse for us continuing to chat. So we stepped out onto the floor and joined the waltzing couples and were soon dancing well together, better than most it seemed. However one or two spectators seemed to be giggling, then I noticed Barbara smiling amusedly at one of her friends. I asked her what was so funny and she blushed and said that I would be upset if she told me and we had better go and sit down.
I wondered what the mystery was, had I committed some horrible ‘faux pas’? Was I about to be dumped, even before any relationship began? What exactly had I done that had caused people to start giggling? I asked Barbara to please tell me, and she just giggled some more then said that it was really nothing, it was just funny. I pushed her for details and she explained that I had been dancing brilliantly, but I had been doing so ‘in reverse’, that I had been dancing the girl’s steps and that she had been leading me rather than the other way round. Now it was my turn to blush and wish for the floor to swallow me up. Barbara noticed I was upset about this and suggested we go to the refreshment area and get a drink. We talked for a long time and I explained that as I was very much the smallest of us boys that I often found myself being asked to act as a partner to the bigger boys much to their amusement and my shame. I say shame, but secretly I very much enjoyed dancing and felt that I was rather good at it. In every other activity I was always the last to be picked for the team because I was so small. Barbara found my explanation amusing, but also indicated that she liked a boy who could dance and was not into the big, ‘macho’ type at all. Just as well really, as I am anything but big, or macho. Standing only five feet three inches tall and being slightly and delicately built I was the very opposite of most of the boys at school.
We got on really well that evening, so much so that arranged to meet away from school one evening. Although I was a boarder, I was allowed two passes a week into town, after prep and back by ten o'clock were the strict rules. Barbara was a day girl (in fact they all were) and lived in a small town nearby. We arranged to meet at a well known coffee house in her town, and away from the artificialities of the school dance got on extremely well and over some few weeks became firm friends. So much so that she asked me to her home on one or two occasions and I had got to meet her parents who seemed more than happy to welcome me into their home. As time went by I sometimes joined them for a meal and with the agreement of the school I often enjoyed Sunday lunch with them. Barbara had told her Mum and Dad about what had happened at the dance when we met for the first time, and how I was so much better at dancing backwards. This seemed to rather endear me to them, and they and Barbara took to always calling me Dee. Barbara and I had been ‘going out’ for about three months when, with special arrangement with both the school and my own parents they offered to take me on holiday with them at half-term.
As my parents were currently both in Nigeria with a British Embassy legation I would normally have to stay at school for the ‘half’ and was delighted with this very generous offer, and looking forward to it immensely. Thus it was that I, some two weeks later, found myself getting off the plane at Marco Polo airport with Barbara and her Mum and Dad, Mr and Mrs Burns and making our way to baggage retrieval. I was looking forward to a week in Venice, and it would be so much nicer with Barbara than on my own or with my parents. However, before we could get away there was the small matter of baggage retrieval and that is where the troubles began. The Burns’ bags were quickly located but of mine there was no sign. after waiting until all the bags were clear Mr Burns went to investigate and discovered the horrible truth. As I had not cleared the old tags off my cases, they had been sent out to Nigeria to where my parents were and it would take six days to get them back to the UK. As we would be away for only the week, it meant I would not be reunited with my luggage until we returned to the UK. There was nothing for it but either to return to the UK or carry on and buy what we needed in Venice. Practicality meant we carried on and after the luxury of a water taxi ride we arrived at our hotel the ‘Malibran’, near to Rialto at about six pm local time.
It was at this point that things took a decidedly strange turn. A brief discussion at the hotel reception soon established that not only were all the clothing shops now shut, but as this weekend was a special saints day it would be unlikely that we would be able to buy much, if anything before Monday, well over 65 hours from now, and the only clothes I have are the ones I am stood up in! What a pickle, how was I going to manage? Two and a half days without a change of clothes and already hot and dirty from the journey! It was Barbara who came up with the idea, and it soon became apparent that as crazy as it was it would be a solution to the problem. Barbara had carefully talked over her idea with her parents and Mr And Mrs Burns were happy to go along and in fact were both intrigued and amused by it.
Barbara’s plan was simple enough, but surely it could never be expected to work. Her suggestion was that I should share her clothes for the time we were there as they were mostly t-shirts and shorts and at worst they would appear androgynous upon me. Although I was very doubtful I agreed to give it a go as there was no alternative. I took the offered clothes, a pair of denim short, shorts and a western style shirt, and for underneath a pair of white ‘Sloggi’ briefs. After showering I pulled on the briefs, marvelling at their light weight and soft texture before stepping into the shorts, which were indeed very, very short and fitted surprisingly well except that they were rather snug at the front and flattened out my bits giving a rather girly profile. The shirt, although very much lighter in weight than a man’s shirt and buttoning up the wrong way was, well just a shirt, although it hung rather low and oddly at the waist. Once I had finished dressing I went to see Barbara who giggled a bit and showed me how the shirt was meant to be knotted at the waist rather than just hang. When she had finished I looked in the mirror and was amazed at what I saw. I looked just like a girl, and I looked quite sexy. At her suggestion we tidied up my rather overlong hair and with the addition of Barbara’s hairpiece clipped in and a very little make up this is how I ended up looking.
Barbara was excited and insisted we show her Mum and Dad, who were amazed at the transformation. After a long discussion it was suggested that it might be best, if I was prepared to agree, for me to pretend to be a girl during our stay. If there was any problem over passports Mr Burns would explain that I was in the process of ‘transitioning’. Although I was somewhat uncomfortable about all this I had little option but to agree. Once these matters had been settled we went out to enjoy dinner. This experience was a revelation. Not once did anyone doubt that I was what I appeared to be and that Barbara and I were pretty teenage sisters enjoying a holiday with Mum and Dad. I soon stopped worrying about how I was dressed and how I looked and began to enjoy the attention I was getting and ended up having a wonderful evening with my quasi-adoptive family. Thus the ‘die had been cast’ for the rest of the holiday and who knew what adventures awaited. When we returned to our hotel, Barbara and her Mum had a whispered conversation after which Barbara handed me a small bag and said I was to get up early and have a bath and put on what was in the bag and await her and her Mum who would help get me dressed for the day. She suggested it would be a good idea if I were to ensure that I shaved every hair from my body and that her Dad had put a razor and shaving cream in my room. This was not really a big deal as I am not that hairy anyway and only need to shave twice a week at most.
For the rest of that week I continued to wear a selection of Barbara’s blouses, shirts, shorts and jeans and seemed to be accepted as a rather tomboyish girl rather than a boy in drag. It turned out to be rather fun fooling all of the people all of the time and I was quite enjoying being a girl for the week. However, our final evening was to be rather different. The senior Burns had been invited to a rather lovely restaurant by some very well connected friends and it had been suggested it would be nice for their daughters to come along as well. This caused them to ask if I would mind playing along as these people were rather important to Mr. Burns business interests. It would, however, mean I would need to be dressed in skirts as well brought up young ladies would not be seen in top restaurants in trousers. As the Burns had been so kind to me I agreed that I would go along with whatever they decided would be right.
Thus it was that at five o’clock after a long soak in a scented bath ( Barbara had added some bath salts to my bag of goodies) I was sat on the edge of my bed very self-consciously wearing only a tiny pair of black thong panties with lace around the waist and a sweet pink bow at the front, feeling very exposed. At the sound of a gentle knock on the door I let in both Barbara and her Mum who had come carrying a huge bag of things. “ Let’s look at you”, they said, and made me stand and pose whilst they whispered together. Barbara’s Mum then announced that having talked matters over with her husband and daughter that they agreed I needed to embrace my feminine side rather more if I were to carry this off and as and as they had planned a rather special night I would need to wear something suitable and so I would need all possible help. Thus she had bought a selection of suitable clothes and that Barbara was to stay with me and help me get ready at the same time as finishing getting herself ready. As we would of necessity be alone we were subtly warned that this was to be regarded very much as “all girls together” and there was to be no shenanigans or funny business. Mrs Burns then left us to get ready.
Barbara looked at me sitting in my tiny panties, and reached out and gave me a quick hug and kiss before emptying the huge bag onto the bed. Commenting about how proud she was of me for agreeing to do this she started to sort out the masses of very feminine lingerie that had tumbled from the bag. Once she had things arranged to her satisfaction she completely surprised me by unzipping her skirt and letting it drop to the floor as she pulled otf her tee shirt to stand in front of me wearing only identical panties. This was so totally unexpected all I could do was to stare open mouthed at the vision before me. Barbara just laughed and said quietly, “ all girls together! Remember you promised Mum, and by the way she wants you to call her that this evening - please. Saying this she put her arms around me and gave me a lingering kiss. As we broke apart I was, however, getting rather embarrassed parading in this skimpy underwear in front my girlfriend and seeing and feeling her nakedness and a certain part of my anatomy was trying to draw attention to itself. My panties were beginning to bulge a little. Barbara noticed and I was standing blushing and trying, with very little success, to hide my erection I stammered an apology and asked what I could do about it and she explained that this was something she knew about as her Mum had told her that she and her Dad sometimes played dressing up games in private and the same thing happened to him. She then asked if I ever played with myself and blushing I admitted that I did, but I knew I shouldn’t. She told me it wasn’t something that I should be afraid of or think was dirty as it was perfectly natural and it was what I needed to do now and that she would be honoured to watch if I were to show her how I did it. Handing me a box of tissues she said “Don’t take too long and don’t mess up your pretty panties as we have a lot to do”. I slid the tiny garment carefully down and my erection, tiny as it was sprang out from their tight confines. Barbara said “ Wow, it’s smaller than I expected, but it is very pretty, can I kiss it?” I could hardly speak so I just nodded and nearly swooned as she delicately held it and kissed the throbbing end gently. I had never experienced anything like this before and it was so unexpected that I exploded into the tissues after just a few seconds and I wiped myself up. Barbara gently pushed the previously proud, but now flaccid flesh firmly down between my legs and pulled my panties tight to give me a smooth front just like her own.
She smiled at me and said how much she had enjoyed that and that there would be other experiences we could enjoy ‘ If I were a Good Girl!’; but now we had better get ourselves ready.
She had decided that a basque would be absolutely right and help my figure and had chosen matching boned black lace basques for us to wear. She showed me how to put it on and push the garter tabs under my panties so that I would be able to go to the toilet without needing to virtually undress. Oh, garter tabs! Of course this meant I would need to wear stockings, and I was shown how to carefully roll these up my legs and attach them. Next she produced these very glamorous sandals as she was the same size as me. I slid them onto my stockinged feet and marvelled at how comfortable they felt. It was only later that Barbara told me they were expensive designer shoes by Jimmy Choo and her Mum had decided upon them so as not to frighten me with more uncomfortable cheap heels. She then had me practice walking up and down until they were sure I could manage the heels.
Looking into the mirror I was amazed how girly I looked, and I said to Barbara that if it wasn’t for my flat chest I could easily pass as a real girl. She blushed a little, and said she had forgotten something important and had me loosen the basque and sit in an upright chair. I felt her gently massage my chest and her insert something soft and cool into the bra cups before tightening everything up rather more than it had been before. When I looked down I let out a gasp of astonishment - I had boobies, little mounds on my chest that my touch confirmed were me! Barbara explained that by massaging the skin of my chest upwards as she tightened the boned basque that she had added to the bra cups a couple of small ‘chicken fillets’, small bra stuffers that girls used to enhance their assets. The result was little titties that looked about an A to B cup. She asked me to sit whilst she got ready and then attired in a similar manner to myself she got to work on makeup and hair. By the time she had finished we looked alike, maybe not twins, but definitely sisters.
As Barbara finished my lipstick there was a knock on the door and Barbara’s Mum entered and passed us both two more items, a very short black lace full slip and an exquisite cocktail dress that had a translucent top in a smokey grey colour and a black lace skirt that fell just below mid-thigh and waited whilst we slipped these on. The outfit was It was exquisite, soft, delicate and weighed virtually nothing, but made me look like a million pounds. I just couldn’t help twisting around and admiring how I looked. I was concerned that the dress showed rather too much as the almost transparent top displayed those glamourous underpinnings and even my little breasts were quite evident. In addition the very short skirt would show my stocking tops if I were not very careful in how I moved. However, both Barbara and her Mum assured me that this was OK and would be all part of the fun we could have tonight. A little innocent teasing would be exactly what would be expected from two attractive teenage girls. She now explained that for tonight she and Mr Burns were going to by my Mummy and Daddy as their hosts assumed Barbara and I were their daughters and they hoped I could agree to this. Of course I agreed, and asked what they were going to call me as surely they couldn’t have a daughter called David. Barbara suggested That we keep it simple and use my initials run together, DT said and spelt as Deety, and this was agreed. It was now time to go and introduce to Daddy his new daughter.
A few minutes later we arrived outside the door of the Burns’s room and I was led in by Mummy to meet Daddy! The look on his face was priceless, a true, literal, jaw-dropping moment. Mummy ( Mrs Burns) asked him what he thought of his new daughter Deety. “ If I didn’t know there is no way I could possibly tell,” he muttered “give us twirl girl and let me see you properly”. Cheekily, I swung round in a rapid pirouette letting my skirt fly and flashing both knickers and stocking tops. He told me to stop showing off, but that I had behaved exactly as Barbara would have done in the same circumstances and that I more than passed and that Barbara and I would definitely be going with him tonight. (Later I learnt that had he not been convinced by my appearance we would have been left .). At this Barbara ran to him and said “Thank you, Daddy” and kissed his cheek, so I did exactly the same, causing both him and me to blush.
And so, our new little family set of to meet Mr Burns new friends at the DanieÄºli restaurant. To say that we had a good time was an understatement. The food was wonderful and the waiters flirted outrageously with us girls(he he). After we had eaten we went on to a club where my ability to dance backwards in high heels was tested by both Mr Burns and Sn. Moretti. It was turned three in the morning when we returned to our hotel and Barbara was sent to help me get undressed before returning to her room, reminding me that we would need to leave at ten-thirty tomorrow and that I should be packed by then and wearing something androgynous so as to minimise any problems with my Passport. The next morning, after careful consideration, I selected by far the most feminine pair of pantiesto wear as a sort of farewell to a wonderful week. Over these I wore a soft shirt style blouse and a pair of pale blue chino type three-quarter length pants and on my feet Converse trainers. This was deemed suitable and indeed we had no trouble with the Border Force and were soon back at the Burn’s home.
There were still two clear weeks before I had to return to school and it had been agreed I would spend these with the Burns’. Whilst it was nice to be reunited with my missing suitcase and indeed the other clothes I had left at the Burns house it felt slightly disappointing to go back to boys clothing after my adventure in Venice. What I didn’t know is that I wasn’t the only to nice my change of mood. It was Barbara who asked me what was wrong, and I couldn’t tell her because it all seemed so silly, but it was her Mum who spotted the reason and she asked me why I had chosen to come home in Barbara's clothes rather than my own which she had had washed and ironed for me. Especially why had I chosen, of all things, that tiny pink g-string pantie to wear when there were plenty of others that were more substantial even including my boxers. I tried to explain to them both and they decided we should hold what they called a Family council to discuss the matter, all four of us. Thus later that first evening we were home Mr and Mrs Burns and Barbara sat down with me and started to talk and question me.
I explained that the week in Venice had been the very best time I had had in my life. Because of my small size and delicate nature I had never really fitted into the boy’s school camaraderie. Indeed, I had been bullied both physically and verbally for years. This week away, despite the unusual circumstances I found myself in had been the very best time that I could ever remember. Somehow, the crossdressing had released something within me and for the first time in my life I had felt free. I hadn't wanted things to end and this explained my choice of clothes for the return trip, and if this had concerned any of them why had no one said anything. Mr Burns then explained that from the very first time they had met me he had noticed something about me and as his profession was a psychiatrist specialising in teenagers he had become worried about me. He had actively encouraged Barbara’s interest in me and had become increasingly surprised at the way we complemented each other. It was apparent that whilst in no way being a sexual or gender issue that in terms of the relationship between the two of us that Barbara took the masculine role primarily whilst my role was more feminine and subservient. As things developed he had been in contact with my parents and with the school and had a clear idea that something needed to be done. Hence the holiday, the ‘accidental’ loss of my case, and the ensuring there were sufficient female garments in Barbara’s luggage. He was not at all surprised at the outcome and during the day had had a number of conversations with both my school and my parents, and as a result both Barbara and I had a number of issues to address and questions to answer. The result of these might affect our futures so did we want to confront these matters or go our separate ways?
As you can imagine the next couple of hours were to say the least emotional, not least when I learnt that Barbara wanted to both protect me and help me whatever I decided. We may have been young but circumstances had forced some very mature decisions upon us. Basically my parents and the school had insisted that if I were to return to either of them I would be required to undertake some form of aversion therapy and be purged of any feminine aspects of character. There were no ‘ifs’ it must be done whatever the effect on my personality, neither the school or my authoritarian father were prepared to accept less. As an alternative the Burns were prepared to adopt me and care for me in ‘loco parentis’ and support me whatever I decided. The next question was very much one of sexuality, did I feel I was in the wrong sex, would I want to seek gender reassignment ( with surgical intervention)? I was opposed to this and so also was Barbara. I am male, maybe not a good one and maybe with a few oddities, but I am happy being male even if I like dressing up. Thankfully Barbara felt the same way and really wanted me as a brother, not as an ersatz sister. That left only the matter of crossdressing and the Burn's made it quite clear that They felt this was an area they could not only support but also agree and encourage.
Thus it was that some six months later I found myself being hassled to get ready to try out a girls school for size.