Shorts Story

A  different kind of story, about a teen age boy having to wear shorts . No diapers or AB.  But I think some of the readers of this blog will appreciate it anyway. Specially part two with some boy to girl cross-dressing, gender-confusion, coming of age stuff.

Part 1

When I was a primary schoolboy some 40 years ago we wore a uniform that consisted in summer of navy blue shorts, under a white and blue striped shirt, and a blue sweater. The trousers were real short and had tight fitting legs. On an ordinary school day we would wear short blue socks, but for special occasions white knee high socks were required. In winter the shorts were replaced by grey pants.

When around the age of 12 we went to secondary school, uniform regulations didn’t change except for the fact that we were free to wear shorts or normal trousers all year long. Of course we considered shorts to be childish and the kids whose parents made them wear them, were mocked by the others.

Towards the end of the winter of my first year in secondary school I fell off my bike, tearing a big hole in one of my two pairs of trousers. My mother was very upset and told me I would have to manage the rest of the school year with just one pair. She would arrange to wash and iron my pants during the week-ends when necessary.

A couple of weeks after that accident however, an evening at dinner I dropped a complete plate of food on my lap. It was impossible to wear my pants without having them washed. The next day was a school-day so my mother, after first making a big fuss, promised she would wash them and would let them dry over night and iron them in the morning. The next morning however she realised she had completely forgotten.

Running around in my underpants I made a big fuss saying that I would have to stay home that day. My mother went to fetch a pair of old uniform shorts and, observing it was a nice spring day, suggested I would wear those to school that day. I raised even more hell, telling that that was out of the question. Right at that moment we heard the honking of the neighbour who always took me to school since his children went to the same school.

My mother got even more worked up yelling that I was not going to stay home. My father, who up to that moment hadn’t intervened at all, slowly raised from his chair, trusted the shorts in my hands, and quietly said:” I’ve had enough of this discussion. Now you put on those shorts immediately, get off to school, and from now on you’ll wear shorts until the end of your schooldays. Understood ?” Knowing my father, I realised it would be stupid to protest on such a moment. So fighting back my tears I pulled on the shorts and, as the neighbour was already honking for a second time, grabbed my briefcase and ran out.

The mocking remarks started right after I entered the car. In the car I found, as always, my best friend Paul, his younger brother Alex, and his older sister Anna. Paul was only 6 months younger than me, but as his birthday was in the beginning of the year, he was one grade below me, attending classes in the last year of primary school. Alex was one year younger. The two boys went to the same, all-boys, school as me. Anna was 1,5 year older than me and went to an all-girls school right across the street from my school.

At the time I was rather small for my age and I was quiet shy, especially with girls. As neighbours we had known each other for a long time but that didn’t prevent me from being the object of a lot of teasing by this 13,5 year old, precocious girl. Joining her and her two younger brothers in the car, wearing my shorts was an invitation she couldn’t let pass. Once at school I enjoyed the same kind of attention all day long from my class mates.

And all day long I thought about what my father had said, hoping he hadn’t been serious with his threat to have me wear shorts all the time. But that afternoon when I came home I immediately knew my hope had been in vain. I found my mother sitting at the sewing machine converting all my trousers into shorts. My father had cut off the legs of all my pants and my mother was sewing new rims on them. I started screaming and crying but I knew this was definite.

At school my position changed instantly. Up to that day, despite my shyness I had been able to be accepted by the “in-crowd”. But now everybody took their distance. Small, shy, and wearing shorts, there were limits to what they could accept. The teasing became relentless and much meaner than before. So slowly I started avoiding them and began hanging around with the 10% or so of boys wearing shorts. I became even shyer, especially when there were girls around.

I was used to spend after school time, weekends and holidays at Paul’s place. Together with, Alex, who was one year younger, we had great times. When we had been younger Anna had often joined our games, but a couple of years ago she stopped participating in our games The fact that I was wearing shorts all the time didn’t change anything in my friendship with the two brothers. I continued to spend most of my time at their place. Since Anna always more or less ignored me anyway nothing changed. Furthermore it was soon summer holiday which we spend mostly in tennis shorts and swim suits, so the fact that I was not allowed to wear pants went quiet unnoticed.

Starting the next school year however things became much worse. I was now one of the only boys of my grade wearing shorts. Paul had made the transition to secondary school and had his recreation time now at the same time and place as me. But of course he now also wore trousers. Our friendship was put to a rude test since Paul was under pressure from his cooler classmates to drop this shorts wearing 8th grader as a friend. But after some embarrassing and awkward time, we remained friends and together hung around with the shorts-boys from his grade. Paul and I had been champions at playing with marbles, a game that normally wasn’t played once out of primary school. But we soon had formed a small group of 7th graders to play with us. This confirmed our status as somewhat childish boys, especially for me as the oldest of the group. This became even more so when after a couple of months the weather got colder and I was the only boy in the whole school to wear shorts.

I begged my father to change his mind but it had become something beyond discussion, or reason. During the summer things improved again, but then at the beginning of 9th grade I hit bottom.

Our school had started a process of rapprochement with the girls school at the other side of the street. It didn’t offer anymore the direction I had chosen to follow from that grade on, but the girls school accepted boys in that direction. The result was that I found myself with some 15 other boys attending classes in a girls school. For some classes, such as physical education, as well as for the lunch time, we would cross the street and join the other boys in the boys school. To make matters worse I found myself in the same class as Anna who the previous year had had to do her year over.

Here I was, 14 years old, wearing shorts, attending class with a 15 year old girl, who of course made it very clear from the first moment that I shouldn’t count on her leniency because I was a friend of her brothers. She either ignored me, or would ridicule me in front of our classmates ( “come back when you’ll have some hair on those legs”, “you better go play with your dinky-toys”, “this is nothing for little boys” were some of her favourite remarks). And when I would cross the street to the boys school things weren’t any better. Alex had joined us in secondary school but contrary to his brother wasn’t going to loose his friends by playing with a shorts-boy. And since I wasn’t there most of the time he soon had convinced Paul to take his distance from me too.

On top of that, times were changing and the dress code was adapting itself to this new times: there were only a handful of 7th graders who started the school year in short trousers. I had become quiet isolated. During the recreations in the girls school I would mostly hang around by myself. Keeping as far away as possible from my classmates, I would watch the 7th graders rope skipping or elastic jumping. Most embarrassing would be when some teacher would take pity and would ask those 12 year old girls to let me join in their games. I would of course protest but the teacher and the girls would insist, and when I finally relented one of my classmates would pass by, cementing my status as a little kid not fit to be in their class.

And, as I said, at the other side of the street things weren’t any better. There I was now also forced to hang around with the 3 or 4, 12 year old boys who wore shorts. But they obviously found me somewhat weird. And on top of that, word soon got out that at the girls school I was seen rope skipping. If the shorts-boys had at first been somewhat proud of the attention this 14 year old was paying them, they too preferred from then on not to be seen too much around me.

I was quiet desperate. I didn’t know it at the time but I had hit bottom. From there on things would slowly start to turn for the better. But that’s stuff for another story.

Part 2

Was it because of the new study direction, or the different teachers, I don’t know, but until then I had been a less than average student, and now became one of the best of my class. Then winter came, and I was again the only boy in the whole school wearing shorts. But contrary to the previous year when this had only reinforced my young boy image, this time I became somewhat of an eccentric, braving the freezing weather with bare legs.

The next summer things began to change real fast. I was now almost 15 year old and had finally started to grow. Little by little my tennis game had become very good and I started to have successes in local tournaments. I went to BBQ’s and after tennis tournament parties, wearing my eternal shorts. Everybody was by now so accustomed to my shorts, which I preferred to be very short and sporty, that nobody commented on it anymore.

But then suddenly there was this new girl who became a member of our tennis club. She was 16, very good looking, with very long legs, which she liked to show, frequently wearing shorts. She soon made remarks, but quiet different from what I had been used to. Now I suddenly got complements on my sexy legs. Despite my improved status I was still very shy with girls and turned red every time she made such a remark. This made her laugh and incited her to do it even more frequently. After a couple of weeks Carinne, that was her name, and me had become good friends.

The fact that this gorgeous, sexy, older girl had become my friend was so astonishing that I had wet dreams about her. And because of that I started having erections whenever we met. Wearing my short, tight fitting shorts this was hard to hide and she noticed it almost immediately. She thought this was hilarious and from then on would do anything to get me into that embarrassing situation. For instance we would have a drink after a game, sitting next to each other, talking with some other friends. And she would lean over to me, put her hand on my crotch for just a second and whisper something in my ear. I would immediately get such a huge erection that I feared my shorts would burst open. And then she would ask me to fetch something at the bar. I would try to save time hoping the erection would go over before standing up, or casually grab a sweater and hold it before me. It was horrible, but I loved it. And I managed most of the time to hide those embarrassing situations from the others, but on a couple of occasions someone noticed and made remarks about it, making me turn red and stammer.

One day she asked me to come over to her place because she wanted to show me something. There was nobody at home at her place. I would soon learn this was almost always the case. We went straight to her room, where she opened her wardrobe to reveal the largest collection of shorts I had ever seen. She had shorts in all colours, and all kind of models and shapes that one could imagine.

She started taking out her favourites, and would ask me which ones I preferred, and we discussed the reasons for which we would prefer one or other model. After I had strongly defended my preference for one model she trusted it in my hands and told me I could have them. When a few minutes earlier I had fervently defended the aesthetic qualities of that specific pair of shorts I hadn’t thought about me wearing them. It was a very girlie model, made of red and white gingham, stretching fabric. They were very short, with an elastic waist, no fly, and two fake pockets both in the front and in the back. Being taken by surprise I didn’t know how to react except for thanking her. But that was not what she had in mind.

She told me that I should try them on. I don’t know if I didn’t dare to refuse or secretly wanted to try them, a fact is that I went to the bathroom and a few minutes later came out wearing those shorts. Of course I had another erection. Carinne came up to me, put her hand on my thing and telling me I looked lovely gave me a short kiss on the cheek. I was of course in heaven.

From then on we would often spend time at her place and she would make me try on different kinds of shorts. She always insisted I try on the more girlie models. So I would wear pastel coloured shorts with a high waist, closing with a short zip on the side or the back, or bright-coloured short-alls, or extreme short cut-offs. The next thing was that we went to department stores to buy new shorts, if possible identical for both of us. To go each to the respective fitting rooms, holding the same shorts really excited us. The way the staff looked at me embarrassed me of course, but at the same time I enjoyed it tremendously.

This continued during the whole summer. Carinne had become my tennis-partner in double mixed matches. She lived very close to the tennis club from where the bus would leave to bring us to tournaments. To save time in the morning, on the nights before matches I would stay over at her place. Her parents were usually not there, so our game would continue during those nights. On one of our first visits to the shopping mall we bought identical girls pyjama-shorts for both of us.

Carinne was an only child and her parents had spoiled her with toys since she was born. Since none of those toys had been discarded, Carinne had a huge collection of toys, for all ages, filling a complete, very large, playing room. Before soon we would dress in our identical girls shorts and play together with Barbies or other dolls. The sexy 16-year-old could instantly turn into a little girl, and I soon learned to do the same.

Towards the end of the summer she insisted I would go out wearing girls shorts. At first I refused but relented when she insisted. I was hopelessly in love with her and couldn’t refuse her anything. So I began occasionally to wear girls shorts in public. Although I took care to choose the less conspicuous models, it didn’t take long before our friends started making fun of me again. To my dismay Carinne seemed to enjoy it, and even joined in the teasing. Our shared private secrets didn’t prevent her from treating me as her kid brother in public. When she was surrounded by older boys, as was usually the case, or with girls her age, such as Anna, she would always send me away after a while. She managed to do this in a friendly way, but nevertheless it hurt every time. She would for instance remind me I had told her I still had a lot of homework to do. Or worse, she would point out to a group of younger boys, and tell me I shouldn’t neglect my friends so much. I always took the hint and went away, leaving her with the others.

The last weekend of august, the tennis club organised an end-of-holiday party. As I had played a very strong season, and Carinne and I had won the finals in the double mixed club championship for adults, I looked forward to the party. The party consisted of a family BBQ in the late afternoon followed by a dance. The prices of the championship were given during the meal. During the beginning of the meal Carinne didn’t object to me sitting next to her at the table of the young adults, waiting to be called forward. Receiving the trophy together with Carinne was without doubt the high moment of my life. But it was immediately followed by the expected letdown.

After receiving our prize I went back to sit at Carinne’s table. But then made the mistake to go for another serving. When I came back I found some 18 year old boy had taken my place. I looked pleadingly to Carinne hoping she would let me stay in respect for the ovation we had received together a few moments before. But in vain. Carinne, putting her arm around my shoulder and looking towards a table with the younger kids, said she thought my friends were waiting to congratulate me. Before I could protest she kissed me on my cheek and gave me an encouraging pat on my shorts. Nothing else I could do but give her a kiss too, and walk over to the kid’s table where I was indeed enthusiastically received. After all it was not a small feat for one of them to win a trophy in the adults championship.

I have often wondered why Carinne treated me that way, and why I accepted it. At the time we sometimes talked about it. Carinne would explain to me, and to herself, that her parents had always pressured her to be the best, and she enjoyed shedding all this pressure by playing a little girl without any responsibility. I would answer that I was so much in love with her that I would do anything to be with her and to please her. As for us wearing shorts we would agree we just loved the way it looked. And Carinne would often repeat she found my legs sexy.

It is difficult to understand what our real motivations were. With hindsight I think they were very complex. It is obvious our little games had an erotic nature. However, although Carinne often rewarded me with a kiss, sometimes stroked my legs or furtively touched my crotch, we never went beyond those almost brotherly contacts. I guess both of us were testing our sexual orientation.

I was obviously experimenting with my gender, although at that time “gender confusion” was something we had never heard of. Since I didn’t know the difference between cross-dressing and homosexuality I wondered if I was gay, but the fact that I was only attracted to girls didn’t make it easier for me to understand.

For Carinne on the other hand, I think I was a “safe” way to experiment with some lesbian or bi-sexual tendencies. At the same time there was in this game also an element of female domination. I enjoyed obeying Carinne’s quirks, and unconsciously took pleasure being humiliated in front of my peers. And I suppose Carinne enjoyed ordering me around and humiliating me.

But this last aspect didn’t square with her desire to play little girls games whenever the two of us were in private. I sometimes wonder if she hadn’t been a guilt-raked victim of incest, and her turning into a little girl was a way to become “pure” again?

But let’s go back to what happened after that summer. When school started I unexpectedly discovered grey trousers hanging in my wardrobe. My mother didn’t say anything about it, but I simply started wearing trousers to school. My parents never said why they decided to lift the ban, issued 3 years before, on wearing trousers up to the end of my schooldays. Did they just think it had been enough, or were they worried about my sexual orientation? I’ve never known, but it suddenly was all over.

Nevertheless I continued to wear shorts after school since Carinne insisted I do. Although with the weather becoming cooler, she completely stopped wearing shorts herself. That winter went by without any notable events, not that I remember any way. But at Valentine day Carinne had arranged for me to sleep over once again at her place. After dinner she took me to her room and gave me “our present”. They were two identical baby-doll nightdresses, consisting of a short shirt in a light, flower-print fabric, with puffy short sleeves, and assorted blooming baby-pants. I was horrified, but as Carinne insisted I relented and wore them that evening and night. Although once I had accepted to put the baby-doll nightdress on, I had settled into it as usual, accepting to play the whole evening with Carinne’s dolls. But having been made to wear complete female attire had bothered me more than I had realised at the moment.

And a couple of weeks (or days?) later something happened that would cure me of my dependency of Carinne’s whims. It made me turn away from shorts for a long time.

The tennis club organised a costumed carnival party and Carinne accepted to be my date. It was the very first time she did so, and I thought it was her way to reward me for accepting to wear the baby-doll dress on Valentines Day. I accepted of course to have her decide the costume we would wear to the party. On the day of the party she came over to my place wearing an old school-uniform. It consisted of a navy blue skirt with suspenders, which she wore under a white blouse and knee high white socks. She asked me to take out my old school-uniform consisting of navy blue shorts, a white dress shirt and blue knee socks.

Understanding we would go as a couple of school kids I thought this not very original, and a little embarrassing considering I had still been wearing those shorts the school year before. But then Carinne took off her skirt and blouse and, telling me to do the same, she told me that the idea was that she was going as a schoolboy and I would be a schoolgirl. Having to dress as a girl for the second time in a couple of weeks made me very angry. Of course after a while, as always, I accepted, and I found myself wearing the skirt over mary-jane shoes, the outfit being completed with a big bow tie.

Carinne (on the left !) and me

We were a big hit that evening. But I had to endure an enormous amount of mockery, since everybody understood this to be the apotheoses of all the previous months.

The next day I told her I stopped our games. For many years I was “cured”. I studied, started a successful career, married and got children. Starting in my mid-thirties however I began secretly wearing shorts, skirts and dresses, which I still do. As for Carinne, I completely lost her out of sight, but I’m almost sure she decided she was lesbian and looked for and, hopefully, found the real thing.

Clair