Some time ago Barbie Lee sort of challenged me in one of her blogs (https://bigclosetr.us/topshelf/blog-entry/78714/illegal-make...).
At the time I was not really in a shape to do anything about it and didn’t get a silly enough idea. Let’s see if this is silly enough. As for those who think I write too short stories: This is the longest I have posted here. It's also more narrative than most of them.

12 years from now.

My fiancée Mary and I were spending a quiet day in my flat when the door-bell rang. When I opened the door I found Tom, well really Thomasine, my fiancées tomboy younger sister there in tears and carrying among other things the ruins of her prom dress. As it turned out not only her dress had been destroyed. Andrea, their bratty freshman brother, had totally flipped out and hadn’t stopped at the dress but also destroyed Tom’s jewelry and even got in a cut or two with a pair of scissors in Tom’s hair. She looked a mess. All she had left were her shoes and panties and the prom was only a few hours away. Disaster!

There was only one thing to do. I went into my bedroom and got out MY old prom dress.

Mary (rather upset): Peter, why do you have that dress?

I was rather surprised. I thought she knew. This could be awkward. Well, we’ll take care of that problem later. Now we had more important things to take care of. As I started to check if my dress could fit Tom I absentmindedly answered:

- It’s my old prom dress. I graduated from West Peak.

Mary (with a gasp): The infamous West Peak Academy for Young Ladies?

Well, some may call it infamous. I prefer famous. A fame that I’m proud to be partially responsible for. You see, I’m the only boy ever to graduate from that high school/boarding school.

I still remember the 14 year old me standing outside West Peak Academy for Young Ladies on my first day of freshgirl year. Not freshman, freshgirl. Just as the students in their final year weren’t seniors but “Ladies”.

I was terribly embarrassed. I was the only boy standing there in my brand new school skirt, my first ever, and my bra, also a first, felt awfully awkward. And I wasn’t exactly invisible either. I was a large boy for my age so I towered over the other freshgirls. I cursed my fate and wished that I were anywhere else but there. At the time I had no idea about the circumstances leading up to that first humiliating morning.

West Peak had just been forced to abandon their girls’ only policy after more than a century. They had done so very unwillingly and had tried to save just a little bit by defining a conventional dress code for boys and another, extremely feminine, for the girls. You can imagine the despondency in the board room when they were informed about the court verdict proclaiming their new, segregated, dress code illegal. That is, until one of the board members realized that the second problem could take care of the first. They simply did away with one version of the dress code, making the remaining one apply to both sexes, and thus legal. They also reversed the curriculum changes so that all the comportment, beauty, ballet … lessons once more became compulsory for all students.

As expected when parents of the few boys admitted were informed about that and that their sons would be required to wear skirts, bras, panties, hose … they withdrew. All, that is, except me. My parents didn’t have much money but I had received several scholarship offers. My parents had chosen West Peak because of its stellar academic reputation and since it was going coed … I was not that pleased even before the terrible news. At the time I was a budding athlete and whatever West Peak’s academic reputation it was not exactly known for its sports achievements. When the latest changes were made known to us we had already declined the other offers since I had been accepted to West Peak. My choice was either to get the skirts, bras etc or go to the really rotten local High School. I and my parents disagreed. My parents won so there I was feeling the chilly wind finding its way up my skirt.

The school staff was not too pleased to have me there either. The only good thing was that I got a room of my own. Otherwise they tried to make me flunk out. That should have been easy since their standards were, and are, extremely high both when it comes to the intellectual and the feminine deportment part. Fortunately the “other” girls took me under their wings and helped me. It took me some time to get comfortable and proficient in girls’ clothing and even longer in the deportment department. At first I got some warnings. Fortunately not enough to get me kicked out. My new friends took turns helping me practicing make-up, walking, graceful movements and so on. I also blessed the fact that many of the “other” girls also were wanting in feminine skills so I didn’t really stand out.

Quite a few girls had to leave the Academy for failing to make sufficient progress though. By that time I desperately didn’t want to fail. Not only had I found better friends than I ever had had. I also just loved the intellectually stimulating environment. In my old school I made sure not to make my good intellect too obvious. At West Peak? No need! The Academy may have had a reputation of being girly girly but the intellectual stimulus! The reveling in learning and really giving your brain a work-out! I’m bright but I had never had such encouragement, never found such JOY in learning. I didn’t mind the strict learning discipline, I embraced it!

As for the physical work-out I was distinctly discouraged from participating in sports. I did manage to qualify for the cheer leading squad though – they needed a big strong “girl”. In my Lady year I even became captain. Otherwise my need for physical activity was channeled into ballet. Not that I could have known that in my first ballet class. While most of the girls had taken ballet for years I wasn’t the only beginner. However, putting on the pink tights and black spaghetti strap leotard alone in the small cupboard I was told to use as a dressing room (I didn’t start to change together with the other girls until later) I felt I couldn’t be more embarrassed. I was wrong! The frequent, forceful and rather intimate corrections I received (a lot of it involving poking in my butt and thighs) took my embarrassment to completely new levels. That disappeared completely at the end of the class. The teacher complimented me for very good work! She was the first teacher to be on my side. In later years she even stretched things so far as training me in masculine ballet movements. Of course I had to follow the main program too, including pointe shoes when I was ready. For the recital the morning before the Prom I was given a solo. I was by no means one of the best dancers but by then the Academy had realized the treasure they had in me. I did fouettés en pointe. Oh, don’t be silly, not 32! I did 8 and I’m damned proud of it!

My prom really was a dream. As is the tradition West Peak held it together with WMI, a (mostly) boys’ military academy. A gay student had been selected to be my date. He really was extremely handsome in that uniform. He was also the perfect gentleman. He didn’t try to do anything untoward. He wouldn’t even have kissed me if I had objected. I didn’t. We kissed – a lot. He was a master kisser. I learnt sooo much that night. Mary really owes a debt of gratitude to John, not that I will ever tell her.

When I left West Peak Academy for Young Ladies I was well prepared for University – in some ways. Academically I breezed through given my base and study discipline. Socially – not so much. I tried dating girls. I was successful – in befriending them. Not that I didn’t lack dating opportunities. I was like sugar to the femmy-appreciating gay “flies”. No matter how much I tried I couldn’t keep them from buzzing around me. Not that I didn’t have fun with my girl friends but it wasn’t what I had planned. It was until I was finishing my master when this lovely girl turned up on campus. SHE was bright enough to appreciate ALL my sterling qualities.

I admit it was a bit awkward meeting her father for the first time. Oh, not for my “slightly” feminine mannerism, though he had commented on them earlier. No, the embarrassing part that he was the kind and extremely demanding manager who just had selected me, over the objections of his manager (I was “just too girly”), for the plum job I was one of 50 applicants for. I didn’t know and Harry (privately)/Mr Arnolds (at the office) as well as Mary categorically deny any previous knowledge. No matter, I have since proven that the job was the right one for me and that I beyond any doubt was exactly the right person for the job.

The dress I was fitting to Tom, or rather the other way round, was the dress I had worn on MY Prom. Fortunately Tom wasn’t that different in size from what I had been that night. Taking stock of my resources I realized I had everything necessary except make-up. My old had mostly passed its use by date. Tom’s colors were close enough to mine to make me feel secure in knowing what to buy. Being a stunning natural beauty Mary is absolutely hopeless when it comes to cosmetics or the other Arts of Feminine Beauty (where I had got A+) but she IS capable of taking a list to the nearby cosmetics shop with strict instructions to call me if there was anything she couldn’t get. I told her very firmly NOT to rely on any advice in the shop. As it turned out that wasn’t necessary – phew!

I on the other hand had my hands full. Starting with Tom’s hair I soon started weeping. The cuts Andrea had applied were absolutely unforgivable but that was not the worst. That “salon” she had used was beyond criminal. Tom really had fundamentally the most beautiful hair but after what they had done with it I was fortunate, and skilled enough, to get just a LITTLE of her absolutely fabulous lustre to reemerge. I would have to make sure that she got some COMPETENT help when her hair grew out. What was there now was sadly beyond help, at least according to my standards. I gave her a femininely slanted tomboy haircut. Well, she was the school tomboy so that fitted.

Next was dressing her. She was only slightly smaller than I had been and, unfortunately for her, as tubular. No problem though, I knew how to handle that.

I got out my very first bra. Whatever had made my mother buy such a frilly one? Now it was perfect. I also got out my breast enhancers. Sadly, Tom was in even more need of them than I had been. The waist of the dress was way narrower then Tom’s. My waist had never been that diminutive. That’s why I had worn a painfully tightly laced corset that night. Tom needed slightly less force to get the same delightful hour-glass figure I had had at my Prom. The corset is a sturdy one with steel stays.

I still had the spare pair of stockings I had got for my Prom that matched the Prom dress. They hadn’t been easy to find. I never had learned to accept pantyhose. I liked, well actually like, the movements of garters and hate the feeling of being contained around my derrière (which is also why I prefer thongs or boxers). The corset had garters. When I carefully had sculpted Tom into the dress and noted with relief that her shoes went well with the dress Mary had returned with the make-up.

As expected Tom’s skin (or should I call it hide?) was in a pitiful state. She really would need some coaching and lessons but that was for later. My skill was up to the challenge.

I had finished my oeuvre and was attaching my heirloom necklace to Tom’s, or by now definitely Thomasine’s, very swan-like neck. While admonishing her that she had to take very, very good care of it since it meant so much to me - it had gone from mother to daughter for four generations in my family.

Given the circumstances I was quite pleased with the result. Thomasine was now much prettier and feminine than she would have been even without the incident. Her boyfriend was quite stunned when seeing her. The girl Thomasine has a shy smile that really is something. Mary snapped her fingers to get him back to reality and we made sure they got on their way.

Alone again Mary cuddled up to me, kissed me and asked whether I thought Andrea would benefit from a change of schools - to West Peak.

I was relieved that Mary’s initial negative reaction had passed but while I had no doubt at all that Andrea would benefit tremendously from attending West Peak Academy for Young Ladies I was sadly aware that it would never do. He would never be able to live up to the very exacting standards there.

And the fact that he’s a boy? Not a problem. Starting already on my first day at West Peak I was in the center of a media storm. That attention varied over time but West Peak gained national fame (or if you prefer infamy). The school directors decided to try to just sit it out. At first they tried to get rid of me but then I became popular not only among my fellow freshgirls but also among older students and teachers. And I managed to fulfill their very exacting standards. By the end of my freshgirl year I even got a prize for my feminine skills. Which of course was widely reported in media.

For my second year I was not the only boy in school. More than one in ten freshgirls were boys. Very pretty and feminine boys. As a rule they out-girlied the GGs.

When I started my junior year the Academy had realized that they had stumbled over an unexpected but profitable business model. Instead of trying to hide me I became a part of the Academy’s new branding. Me and the majority of the freshgirl class. That’s why I later got a solo at the recital.

I remember leaving West Peak Academy for Young Ladies. I noted that some vandals had removed the “ie” in the entrance sign for West Peak Academy for Young Lad(ie)s. I reflected that no one, absolutely no one, back in the Academy would agree. We all (with one possible exception) adhered to the new motto “Mens Sana in Corpore Muliebri” or as often vulgarly translated – Girly geeks. I resent that version very much. While we are bright and have learnt to make the most of our brains I wouldn’t call us geeks. We are much too refined for that.

While not really allowed according to laws etc the Academy has managed to keep up the number of genetic girls. They don’t want the proportion to fall below 10%. Sadly the attrition rate is higher among GGs than among the other girls. Sensibly enough the Academy has refused to lower their very exacting standards as to both intellectual and feminine achievements and improvements.

West Peak now is unusual in that final exams in the Lady year are taken already in March. Since ther year after I left April is for The Operation. They even got a state law passed that automatically recognizes anyone in her Lady year to qualify. As it turned out no one has reached her Lady year without being fully committed.

So you see, I’m still the only BOY ever to graduate from West Peak Academy for Young Ladies.