Girl 101 - I want a dress, please, mum

Girl 101 - I want a dress, please, mum.

I liked girl's clothes - and I was going to learn about them - that was all too clear. Both mum and my friend Gemma and now the headmaster said so. Girl 101 for Boys .... what was going on?
And now .... everything was changing.

I was sitting in the bus to school with Gemma, my long-time friend from Primary school. We were now both fifteen and we had been friends, probably even each other’s best friends for nearly 8 years. It had been a hard day at school, mock exams in practice for the real thing in a few months; lots of times that a question had been too difficult or an answer hadn’t felt right, or worse, my mind had gone blank. I was relaxed sitting next to Gemma who was wearing the school summer uniform of a cotton dress although without the optional jersey.

Suddenly, Gemma said, “You know, you’re doing it again.”

I jerked and looked at her with alarm. What was she talking about ‘doing it’ let alone ‘again’.

“Whhhh, what d’you mean?”

“Don’t worry, it’s just that I’ve noticed that sometimes, especially after a hard day, when we sit together, you touch my clothes. You do it in a very small, restrained way, but you stroke my skirt or my dress, you, I guess the word is, caress it, even fondle it. It’s certainly deliberate …. even if almost unconscious. What’s up, pup?” She did her occasional rhyming game with what she called me.

“I’ve never done it on purpose. I mean, er, ….” and my attempt at a reply faded into silence.

“I never said anything about it being on purpose. It doesn’t happen often and, really I don’t mind. But once in a while, I do wonder exactly why you are doing it and what it means about you, blue.”


“If I ask you to think about why you do it – would that upset you?”

“N…No. But I’ve just said that I’ve never done it on purpose, in fact, I’m not really sure what you’re talking about.”

“Eric, don’t flannel about. You can be up front with me – I’m your best friend and I have been for years. What’s up with you and this interest, considerable interest in my clothes, eh?”

“It’s nothing – really, it’s nothing. It’s just that I like the feel of the clothes, the cloth, the material ….. it, erm, interests me somehow.”

“Well, that’s more personal information than I‘ve gotten out of you in years. You may be, well, you are my best friend but there’s whole chunks of what makes you you that I don’t really have a clue about. But this sudden admission that there’s something special about the clothes that I wear – well, let’s investigate this a little, shall we, my blushing little sweetie.”

There was a fact I always tried to ignore. Gemma was actually pretty much the same size as me – but she always wore heels – only a couple of inches – but quite enough to be able to look down at me. And she had a figure – with waistline, breasts, real curves. She wasn’t a 10, 9 or even an 8 – but she was a pretty girl with a smile that could light up a room. And she was my best friend. We both had other friends – but what we had was clearly a bit special.

“It’s kind of embarrassing. I’ve obviously kept it pretty well concealed if you’ve never noticed until now. I like the variety – I like the fact that girls can wear such soft and silky and pretty clothes – while us boys have to wear rough, drab, dull materials with boring, uninteresting colours.”

“You goose. Why did you never say this. If you want to dress up then I’ll help you whenever you ask. I can teach you about make-up and all the best bits about being a girl.
I can, …..”

I help my hand up to interrupt. “Hold it right there. I have never, absolutely never wanted to be anything other than a boy. I enjoy having a penis – even if I haven’t got to share it with anyone yet. I ain’t never even thought about being a girl, I don’t want to be a girl, I don’t want to do or be anything. I just want …..” and my flapping mouth fortunately came to a halt.

But perhaps too late.

Gemma smiled at me, quite a nice, gentle smile in the circumstances. “I said ‘goose’ and I meant it. I have never thought of you as anything but a guy – even if you’re my best friend and I can talk to you about anything. I get insights into why boys do and say some of the things they do and say – and why some of that is so unbelievably, unbearably, overwhelmingly coarse, crass, stupid and grubby – and then you are equally good at helping me realize why once in a while they do something sweet, lovely and wonderful without even realizing they’ve done it. There is no way that you’re a girl ….. don’t worry about that. But this interest in non-boy clothes – that does interest me – considerably.” She paused. “Tell me more ….. and I will consider how to assist my friend who is definitely a boy but with an interesting interest in pretty clothes and so on.”

“It’s not easy to say it all in one go – out loud like this – when I’ve never really worked it out for myself.“

“For a start, I can’t go much further than what I said – I am so jealous of the wonderful variety of things that a girl can wear that the average bloke will never have the opportunity to enjoy, well actually not even sample so as to decide if there is potential for enjoyment. I’ve made lists of all the options that girls have that a boy just can’t get close to.

"Been making lists, have we, mmmmm.”

“Well, you know me – I like to be thorough.”

“So, what else do you do – if I’ve never noticed before – what do you do to keep this interest subdued but sufficient and comfortable.”

“I suppose I do a lot of watching. I love girls so much but I love what they wear even more. You know how much I enjoy being with you when you’re shopping or even window-shopping. It gives me lots of opportunities to … er, watch and enjoy.”

“And all the time your interest is just in the clothes – not in the girls or in being a girl.”

“Oh, come on Gemma, I’ve been pretty clear about this – clothes yes, wanting girls – but when I’m older and I find one to have a relationship with – then I’ll want a girl as a lover – but wanting to be a girl – I’ve made that clear, haven’t I.”

“Ooookay, then here’s my offer. You will always be my best friend – but if you’d like to try on any of my clothes then you’re very welcome.”

“Gemma, my friend, I do hear what you say – but for a while yet, I’ll hold back on trying on any of your clothes. I do like the idea of going beyond just being interested in what you girls wear and actually getting the opportunity sometime in the future to be a little more daring. I’ll be thinking about it – quite often actually – until I’m ready. So thank you very very much for being so understanding. And continuing to be my best friend.”

“Don’t take too long. I’m kinda interested in the idea of helping you and teaching you and giving you the opportunity to actually DO something about this interest of yours. But can you help me a bit with some guidance – how long have you been aware of this? Have you done anything about it before? I can’t believe that you’re keeping all this long-term and deep interest under control with an occasional furtive fondle of your best friend’s dress as we travel home on the bus. Eh?”

“Errr, what am I supposed to say?”

“A bit more of the truth perhaps. Let’s wait until we’re home. We can sit quietly in my room and get comfy. Then – it’ll be time to get to grips with this thing of yours.”

I couldn’t prevent the grin that flickered across my face.

“And don’t think smutty thoughts. It’s ugly and unnecessary. Even if it confirms that you are really a boy – because of course we girls never think smutty thoughts. No, of course that’s not true – but I think girls being smutty is probably rather different from how boys are smutty. For a start, all girls know that boys minds are always thinking about girls and sex and everything in between. You blushed, That proves how your mind works. But boys don’t have a clue whether girls think about them in the same way. They know we talk about boys – but they and you don’t have a clue what we talk about. It’ll just be the two of us finding out about this interest you have and what we can do about it.”

“Ssso, Doctor Finkelsteinervitz, you think you can cure me.”

Gemma joined in with our long-standing joke, “Nnno, no, no, I neffer make zee promises – I cannot cure you but I remembers my oath and I shall not harm you – not enough to notice.”

I giggled. And it was a giggle rather than a chuckle.

“And that’s another thing you do, not often, but now and again, you giggle – and somehow actually I like it. It wouldn’t be right for most boys – well not for any others that I can think of – but when you do it – it’s okay.”

I could tell that I was blushing even more – my cheeks felt hot.

“So my Frankenmissy, you want to wear ze pretty soft delicate girly clothes – but you don’t want to stop being a boy. Shall we see what I’ve got in my wardrobe that attracts you – heh?”

“Eerrrmmmmm …. yeah, I’ll go with that. What sort of stuff are we talking.”

“Now – that was just horrible. I’m not going to turn you into a girl because you said that was not what you wanted – but if you’re going to look like a girl then the least you can do is drop almost every syllable of what you’ve just said. No ‘yeah’, no ’stuff’, no slang, no more of the obvious boyness. It’s yucky. Well I mean, when you’re not in full boy-mode you need to adapt and camouflage. I guess you don’t want to be publicly labelled as a ‘boy-in-a-dress’.”

“No – that would be ghastly. I’m just a boy with a real interest in a wider choice of clothes. So you want me to look like a girl but you agree that I’m not going to be or become a girl.”

“Just so, Miss Dolittle.”

“But – thinking about it - why do I have to look like a girl. It’s not as if I’ll be going out or anything.”

“Now how’s that for negative thinking, sweetie. I’m not going to force you into anything – except a pair of panties perhaps. But I’m not going to force you to go outside or to go into town. If I can make you look good then you will be able to decide for yourself whether you’re able or willing or even eager to join the girls in town.”

“Once again I’ll revert to eerrrmm – but yes – if I feel comfortable and confident then I’ll think about that. I’m not making promises – but I won’t say no – yet.”

“That’s good enough. Now step forward, milady, and feast your eyes on the wonders of my wardrobe. Anything that takes your fancy, place on the bed. If you can find, say, five outfits to start with then that’s going to give us both an idea of what you’ll be looking for later.”

“Five – I can tell you three of the ones I want to try straightaway. There’s the green dress with the dark green and white trim that you wore last Sunday, the summer dress with the giant poppies, the dark red hot pants with the silky cream top, oh, and the cream and brown layered skirt and whatever top you recommend. Oh, and the green velvet waistcoat but I don’t know whether that’s with the pale green dress or the pale yellow trouser-suit. And …”

Beth held her hand up to interrupt me. “Enough, enough for now. You’ve been looking at my clothes much more carefully and thoroughly than I ever guessed. First off, we need to get you ready for trying on my clothes. So, get in the bathroom and shower but use my girly shampoo and soap. If you smell right then you’ll be getting into the mood more easily. And congratulations – just the amount you were able to tell me about the clothes proves to me that you are wanting exactly what you’ve already said. Some people would say that only a girl would be able to talk about clothes that way – but there’s lots of men in the fashion industry – and they work with clothes every day without becoming girlish. Well, except those who were that way inclined already – which just proves to me that every group of people is a spectrum. Too much talking and thinking – go and get ready for your first experience with your preferred style of clothing.”


“And I’ll expect you to have shaved under your arms and anywhere else that needs it. And asking you to do this is NOT to make you more girly. If you’re wearing any of my clothes then it’s perfectly reasonable to want you to smell right, at the least. And as for the hair, you won’t get anything of the right feel from my nicely girly materials if you’re covered in fur. And actually I know that you’re not that hairy anyway so a little trim shouldn’t be a problem, eh?”

“Grrrrrhhh” I mumbled – just to show that I wasn’t doing everything she asked without argument.

Some while later, a nicely smelling fairly furless body emerged from shower. One towel wrapped around the waist and one around the head.

Gemma squeaked. “You do NOT walk around like that in my bedroom. Get that towel up where it should be, Miss Dolittle. Stop pretending to be such a boy.”

I suddenly realized what she was talking about, grabbed the towel and reset it around my chest a la girl. And I grinned with a sudden deep expression of happiness that perhaps I was going to be treated as my girl self for a little while. Girl time was coming! I giggled – and this time I knew why I was giggling.

But I still mostly felt like a boy who loved dresses rather than a boy who had a girl hidden away inside. It was just the first time that I had the chance to see if there was anything girly inside me - I had to find out.


Oh we had such fun that afternoon. Gemma helped me put do so many things that were new to me.

What can a girl tell you about her first bra – well, it was wonderful. I loved the way it held me, the way it squeezed me around the chest, the way it made my small boy-breasts shape themselves into the cups. I loved the stretch of the straps over my shoulders. I loved it when Gemma showed me how to check that everything was fitting properly. The back-band – was it too tight or too loose? The cups – did they sag or squeeze? The sides – were they making red marks anywhere? The shoulder-straps – were they too tight, did they need adjusting? I was learning so much of the secret life of a girl. I suppose none of it was actually ’secret’ but it was certain that only the rarest boy would ever know that girls had so much to cope with in such an apparently simple thing as a – bra.

Then we moved on to the panties. Gemma and I both got a bit embarrassed with the necessity to actually look at and, for me, to touch my genitals. I had read about ‘tucking’ and knew that somehow or other my testicles could be .. er .. encouraged back into their cavities – but I didn’t know how to do it without using more force than seemed comfortable. And who was going to teach me. It wasn’t as if there were guidebooks or local shops which advertised their services to boy-girls. Andi did understand the need for things to look right – even while I did repeat that I wasn’t anything other than a boy who loved clothes.

But it was still wonderful putting on that first pair of panties. It was the wonderful way the material felt as it stretched just that little bit over by bum and round my front. It felt so good – and so much better than the thick, clumpy boy’s pants that I had always had before.

Gemma then pulled me towards her wardrobe – a glorious jumble of colour and material and dresses and blouses and all those lovely girl-words. I was lost for words.

Gemma pulled out a skirt and blouse, “I think this might be best to start with. We can try some more things later.”

“Please ……”

“What, honey, do you want something else.”

“Could I try one of those longer dresses first. Somehow, I’d feel more …. I want to feel the swirl and swish of a dress around my legs. To see if it really is as wonderful as it looks.”

“Well, of course, you can. It would be silly not to give you something special on your first afternoon. But we do have plenty of time. ….. Is there anything else that you really want, that you really really want.” And we both giggled as she did the Spice Girls riff. “And I’ve put the outfits you mentioned to one side – when you’ve had a little practice and they will look right on you.”

“I’d like a little bit of make-up and, if you can, to do something with my horrid boy-type hair.”

“Your hair’s not so bad. There’s enough length that I can push it around a bit – I’d like to try anyway. But as for makeup – I’ve only learnt to do a bit of it for myself. Perhaps ….. No. I’ll wait and see about the perhaps.”

“What do you mean.”

“Well, Big Sis may be visiting this evening. From what she writes, well, emails, it’s quite clear that she knows some quite, er, colourful people at Uni – and she might be more willing and certainly more capable with the makeup for you.”

“No. No. No way. On the first afternoon of giving my inside-girl an actual outside – I’m not ready to have anyone else knowing or interfering or …. No.”

“Don’t be silly. I wouldn’t take any risks with my new girlfriend. Trust me.

“Well, when you push a bit quick, it gives me the worries. Let’s just be careful …. And slow. But, for now, puhlease, get me that lovely green dress you wore a few weeks ago.”

“Oh, that dress. I did notice you noticing me and all the time it was the dress rather than the contents. Oh, poo.” Gemma giggled.

In a few moments, Gemma had found the dress and was helping me to slide it over my shoulders in a cascade of slippery-lined chiffon. Not that I knew at that moment that it was chiffon, I was going to learn all the right words as soon as I could.

I wriggled with excitement as the lovely dress poured down and over my skin. I saw the difference in my frontage as my very small breasts stuck forward an inch or so. I loved it. I felt so real – for the first time in my life – I was more girl than the boy I had presented as for fifteen years.

“Oh, that feels so wonderful. I love it.”

I swirled around and felt, for the first time, that wondrous swish and swoop as the frothy material billowed around my knees and calves. I told myself that it was such a girly sensation.

And it felt right. It felt better than anything I had ever worn. It was wonderful.

By the end of the afternoon, I had tried on lots of Gemma’s dresses, some skirts and some blouses. And we had both come to the conclusion that I was much happier as a girl than I had ever been as a pretend-boy. That’s how Gemma described me as she saw my behaviour during the day.

“You’re not pretending to be enjoying this are you – it’s for real. I did think for a moment or two that what you were saying was just a way to get into my bedroom – or something weird like that. But I can see so much more clearly now. What you’ve been doing is pretending to be a boy – it’s not now that’s wrong. ‘Cos you’re not pretending to be a girl as far as I can tell. Oh, this is so exciting.”

“And potentially so difficult. But even though this has been truly wonderful, I am still certain that I’m just a boy who loves pretty clothes.”

“Yeah, that’s for sure. – even though I think sometimes your girl-inside is pretty eager for more.”

“Who can we talk to that won’t go all creepy or shouty about it.”

“Do we know anybody a bit older than us who does any of the LGBT stuff – though we don’t need the L or the G or the B as far as I know. They’re all about sex and nothing to do with what I feel.”

“Could start with the internet – as long as we’re careful. No names, that’s for sure – and no details about age or location. We need sensible answers from some people who’ve been there before.”

“Aren’t we both being amazingly sensible. It feels good doesn’t it.”

We both looked at the clock at the same moment – “Better get out of these pretty things. We do not want your mother saying anything.”

“That’s for sure. And as soon as you’re ready, I’ll make sure there’s not a trace of make-up or anything like that. All mums can give lessons to Sherlock Holmes as soon as their antennae start twitching.”

“That’s for sure.”

It took time, but there were some minutes sitting downstairs before Mrs Cowan came home so that we could relax and be the two buddies that we often were – two bumps on the sofa reading our homework notes.

“Hello, kids, everything going alright. If the kettle’s hot – hint hint – I’ll make some tea for us all when I come downstairs.”

“You’re nearest, your turn.” Gemma gave me a massive nudge with her pointy elbow. I trundled off to put the kettle on and get the cups and everything ready. When I got back to the sofa, Gemma watched me closely. She whispered, “Now, if you weren’t pretending to be a boy, you wold have sat down more carefully, lowered yourself into the seat and swept your dress or skirt from under you so that it wouldn’t get creased. You’ll have to practise for when you’re being a girl.”

“What are you two whispering about, it’s not polite and you shouldn’t need to do it when it’s only the two of you. Do I calculate that it’s something you didn’t want me to hear. You’ll have to be more careful of Mrs Sherlock,” Gemma’s mum smirked.

All that evening, I was conscious that Gemma’s mum was watching me – very carefully. I was right. After I had left, she went to speak to Gemma.

“There’s something going on with you and Eric. And he smells different – less boyish. Strangely he smells of your shower lotion. What is going on? And don’t try to lie – I can always tell when you lie.”

“Wha – no you can’t, can you. No, don’t answer. I’ll tell you what I’ve been doing today with Eric. It’s none of the things you’re expecting or guessing at.”

“That does leave some leeway – even though you’re very young still.”

“Eewww, mum. Too much, too much already.”

“Get on with it.”

So Gemma told her mum about my interest in girl’s clothes. Mrs Cowan jumped to all the wrong conclusions, asked all the wrong questions.

Is he gay? …. No.

Does he think he’s a girl and wants to become a girl? No.

Am I going to have to stop you seeing each other? No.

Is Eric some sort of pervert? Don’t be silly mum.

Is Eric ?

“Oh Mum, get with it. It’s exactly as Eric said – he thinks it’s unfair that girls and women get to have all the fun with colours and materials and slinks and slither and sheer and shiny …. He just wants to be up front about it and enjoy himself. And I would rather I help him than anyone else gets involved in something so important to my best friend.”

“Does his mum know?”

“Um, not yet, but soon.”

“It’s going to be within the next 48 hours, I think. Or I’m going to have to get involved. It’s not proper that Eric is doing this on his own – well, with just your help. And for what you’ve done, I’m proud of you. Not super proud because you should have been more up front to me – but still, proud.”

Gemma grinned. Compliments from her mum meant a lot.

So, next day, Gemma told me what was going to have to happen.

Strangely, I didn’t get stressed. I didn’t panic. I didn’t explode. I was amazed by myself. I just got through the day, possibly better than some other recent days. I let all the aggro drift past me, which disconcerted the aggro-ers. Bullies can’t cope when the victim successfully shows no effect at their efforts.

So – I got home and prepared for mum to come home. I didn’t do the cooking as such but I was perfectly capable of doing the prep-work, peeling potatoes and carrots, chopping onions and the like. Getting out the ingredients for whatever I wanted mum to make – or on this occasion for a dish that she had left instructions about. And tonight, it was chicken in a white sauce with chopped peppers, onions and green peppercorns plus peas and carrots on the side. Quite a lot of preparation. As I sometimes did, I wore an apron to ensure I didn’t splash my clothes. Why make a mess and have to wash an otherwise clean shirt.

When mum came in I had just about finished and was taking off the apron. “Honey, you can keep the apron on if you want to help with the cooking. It’s about time you started some simple lessons. You’ll be in deep doodoo if you get to college and expect all the work to be done by the staff and the girls. Not a good start to being a successful human.”

I smiled back. “Gee thanks, mum, I really really do want to be a successful human being so I can avoid the aliens when they come.”

“You geek, you.” She smiled back. “So, you’ve done the chopping – now it’s time for the hot oil, the frying and the sizzling. The burning of the fingers and the subtle smell of burnt skin.”

“Oooh, horrid. You’re going to make me run away screaming with pain and fear.”

“Now, that’s just being silly – if not girly. But then you are already wearing an apron.”

Somehow my brain decided that this was an opportunity …….

“So – are you suggesting that if I’m doing – carefully worded – ‘girly’ jobs then you want me to be wearing ‘girly’ clothes?”

“Oh no, you’re not going to catch me out with overt simplistic prejudice and stereotyping. You know my rules – you wear the correct clothes for whatever event. If you’re cooking – then you wear something to keep your clothes clean. In this case – use an apron.”

My mouth spoke all by itself – "but if I was doing a female job then you’d expect me to be wearing the right clothes?”

“Um, yes,” she hesitated with her answer.

The mouth continued “and if I was wearing boy clothes I’d be expected to do boy jobs and similarly in feminine clothes than I’d be expected to do feminine tasks?”

“Am I getting a little puzzled at this chain of thinking?”

“It’s just logic, mother dear”

Well, use your brain properly – I’m not falling for the ‘A cat has one more tail than no cat; No cat has four tails; therefore every cat has five tails’ - you did that one when you were only eight. But hold on a second ….. do I calculate that you're asking if you have to wear feminine clothes for feminine tasks – if I were to decide that certain tasks in the house were ‘feminine’ rather than just jobs to be done.”

“Well, are there any such tasks? As long as there aren’t then there will be no need for me to wear a dress. Phew”

“Hmmm, this needs some thinking about. Perhaps there are tasks that I never ask you to do because subconsciously I see them as mum-type tasks or even as unsuitable somehow for you to do ….. I see I may have been unattractively stereotyped in my actions and attitudes. Perhaps we need to investigate and experiment.”

My heart went pit-a-pat. “I’m not sure about this, mum. But if you’re going to insist I have to wear a dress for some jobs, at least let me have some involvement in the choice.”

“What, you sound almost like you want to wear a dress.”

“Half the world wears dresses, mum. Perhaps I ought to know something about how it all works. I’m well aware that I know almost nothing about girls – and perhaps I ought to take whatever opportunities there are.”

“Ohhh..kay, let me think about all this. But I am willing to promise that I won’t make you wear anything silly or sissy. If I decide you’re doing a girl task – then proper and sensible age-suitable clothing will be made available. And if eventually necessary, you will be allowed if not expected to help make informed choices. After all, at this moment you couldn’t make a list of more than about four varieties of the colour green. Any teenage girl with the faintest interest in fashion could give me two if not three times as many off the tip of her tongue. That’s the sort of thing that boys know nothing about. Simple tasks like cooking, cleaning and so on – any competent male should be able to keep his pit tidy, keep himself fed and watered.”

“Are you up for this, bhoy?” and she put on her real deep-south slave-boss voice.

I grinned back. “Yeah, I’m in. If you tell me it’s a girl-job then I’ll be willing to wear the right clothes.”


In the morning, mum said she was building a list of jobs that she never asked me to do – and she was deciding which of these were because I was a boy and which were because I was too young. She said she’d be thinking about it during the day at work.

I began to wonder exactly what I was letting myself in for – just so that I would get the chance to wear pretty clothes.

By the end of the week, we had designed our new way of life. We did both agree that this was going to be a short-term thing just so I had a bit more idea about life for #the other 50%’.

I did tell Gemma and somehow the idea spread over the next month or so – until the head heard about it and asked for more information.

I didn’t have much contact with him so I hadn’t got an opinion about whether he was good or bad at his job. But he was clearly more switched on than I had expected.

“Thank you for coming in to my office – this should only take a few minutes. I’ve been hearing some odd but interesting comments about you two and how Eric is ‘sort of learning Girl-101’. Can you tell me a bit more. Because I’m interested and wondering how many of our pupils need to understand the other 50% a bit better. Rather than looking at the fun bits – which I do want to know about later – tell me what the bad bits are for each of you.”

Gemma said “but I’ve not been doing the opposite of Eric. There is no ‘Boy-101’ that I’m doing.”

“Well, think about it. Do you think there should be such an opportunity – and what do you think you might gain from it. Give me two or three pages about it in a few days time, eh, Miss Cowan. And you can do the same as regards a proper series of lessons in Girl-101, Mister Oldman.”

He continued, “Now that you have brought the ideas to my attention – I can see significant benefit from a deliberate effort to attack ignorance, prejudice and potential abuse. Yes, I can see some downside in giving the wrong ideas to the wrong people – and any such teaching would need to be carefully structured and presented. Give me some more insight into how you are doing this Girl-101. I know there are some who will benefit from a similar mind-altering experience.”

This was far beyond where I wanted to be.

“I have to be open about this sir. You may be having the wrong idea about all this. Yes, it’s true that my mum, Gemma and Gemma’s mum are giving me some help in what we exaggeratedly call ‘Girl-101’ but it’s not that big a thing really. And I’m not one of those ‘boys who knows inside that he’s a girl’. I’m a boy. I’m male. I’m quite proud of my penis – even though I’ve not used it for its official adult purpose yet and I have no intention of doing so with anyone other than Gemma. I’m a boy expecting to be a man – but, here’s the bit that’s off-centre, I was and am interested, if not jealous, of girls and the hugely much bigger choice they have with clothes. I just love the feel of their clothes, the colour, everything – and that’s really what I’m learning about. This ‘Girl-101’ seems to have just grown out of that.”

“It’s been about learning how important it is for some girls, well most really because of peer-pressure, that their clothes co-ordinate, that the colours don’t clash – that sort of thing.”

“I did wonder. But I watched you this last week –and when you’re not with Gemma you come across as a satisfactorily average boy doing boy things in boy-style with your peers. I really do want to think about a few boy-lessons for girls and a few girl-lessons for the boys. Any improvement in what half my school knows about the other half should be a worthwhile target. By the way, if it’s any incentive – I’ll be talking this over with my wife – to see what I should have learnt and haven’t.”

Gemma giggled, “And will you tell us what you need to learn. It would seem fair if we have to tell you what we’re having to learn.”

The head frowned, “Don’t be cheeky …” then he paused. “Actually, that’s a lesson right there. How can I ask you to be open if I’m not open back to you. Although I may edit some of my feedback. Oh dear me, this may be more complicated than I first thought. But I’m not going to back off yet – I just need more information before I consider whether this is a good approach.”

“That was all a bit interesting. I never planned that we’d be making a difference to anyone else.”

Gemma grunted back at me. “Me neither.”

“Needs a bit of thinking about.”

“What’s your first item about what is not-good about being a girl.”

“How much peer-pressure can hurt if you ‘get it wrong’. I don't want to think about how the boys would react if they found out. Ooooh, not nice.”

“Wow, that’s a bit too much insight.”

“The girls have their way of being unkind - and, wow, how unkind some girls can be – even to the point of suddenly dropping and cutting a good friend for no easily apparent reason.”

“And how so very few girls are actually proud and confident of their body and looks. Even the pretty ones.”

“Wow, you have been watching and learning. Good girl-watcher thou are,”

Shut up, Miss Yoda. Or I’ll ask you what you know about the equivalent for boys.”

On the Friday evening, mum and I sat down and discussed the list. It was both hard work and yet somehow easier than I had expected. I took time and at the end of it I took a deep breath and said.”Well,mum, looks like I’ll be needing a dress of my own for all this work. Do we go shopping tomorrow?”

“So, you’re up for this then? No last-minute bottling out?”

“Yes, no, not sure, wait-and-see, let’s give it a go- any other little gems you want me to offer, mum?”

“Alright then. Let’s get ready and go out. I did get you some panties of your own – and some of my skinny clothes will fit – even if they’re not really the right sort of style for you. But they’re not too awful and we can get you some good clothes during the morning.”

“Er, that’s a bit sudden, isn’t it, mum.”

“Well, yes. And also no. I’m not going to make you look like your wearing poorly fitting and well-used second-hand clothes as if from a sister or cast-offs from the charity shops.

“Mum, are you sure about this?”

“Yes, I am. It’s going to be really important to watch you learn some worthwhile facts about us – the ‘other 50%’. You may be doing it because you enjoy the clothes – but it may turn out that you’re setting an important example. I never meant you to grow up as anything other than an ordinary boy – but it turns out that you’re not ordinary. And I want to support you and encourage you in being different. I only want one thing from you right now – I want an upfront open request ‘Please mum will you buy a dress for me.”

“I can do that – but like I said before, I want to be involved in the choice. “

“Darling child, I wouldn’t have it any other way’.

“Please mum – will you buy a dress for me – and I want panties and all the trimmings too.”

I saw my mum take a deep breath ‘Let’s go.”

Later that morning, wearing a new skirt – pale grey with dark grey trimming on each panel and a lovely smooth satin primrose yellow blouse, Mum took me to be fitted for my first bra. It was so wonderful. Having Gemma put a bra on me for the first time was so enjoyable and amazing – but this was even more significant. I was out in public in girl-only-territory. I was wearing a skirt and blouse so that it would be easy to undress for the fitting. I did not expect mum to out me as a boy and I was pretty confident that the shop assistant would just do her job and fit a bra to the nearest available body.

As it was, mum slipped up. She and I tiptoed up to the counter and she said, “I’d like to arrange a fitting for my son, ooops sorry, my daughter Erica.”

The assistant calmed her down. “Now don’t worry. Our job is to fit bras to people, young and old. If your son, who does look very pretty, wants to wear a bra so that he can look even prettier – well my job is to sell him a selection of bras. I would never have guessed – well perhaps when he had his top off and I could see his real physique – but right here and now – I see a skinny girl with very small breasts. And, like I said, my job is to find a bra and ensure a proper fit.”

She was so kind, and so helpful. Even when I stood in front of her, naked to the waist, I wasn’t upset or stressed in any way.

She had a smooth, continuous series of comments and questions which taught me so much about the wearing of such an intimately feminine item. "Does it feel like the band rides up your back? If it does, your bra is either too large or needs to be tightened. If it's still too loose after you've adjusted the band, it's time to go down a band size (and possibly up a cup). And don’t forget that at certain times your breasts can change by as much as a cup-size."

"Since you don't have much breast tissue, you won't have to worry about your 'girls' spilling over or bulge under the cup? If they did, your bra cups are too small and you need to go up a cup size. You won't have to worry about that as we're going to add a bit of padding."

"You'll notice these cups don't pucker or gap. If they did, your bra would be too large. I'll make sure that doesn't happen.

"Do your straps slip and slide? This is like the biggest problem for us gals. If you've adjusted your straps and they still fall off, either the band is too big or your bra has lost its elasticity. If you have sloped shoulders, opt for a racer back bra or a style with convertible straps. I love racer back and sports bras myself. We can talk about them later if you're interested."

"Do your straps feel like they're digging into your shoulders? If so, I can try loosening them. You shouldn't have this problem unless you start wearing falsies and the size is too big for your bra. We shouldn't have to experience this until you're a little older."

"Many women wear a bra with an underwire. If the wire pokes and prods, you're wearing a cup size that's too small. But you won't have that problem because we're padding and I'm obviously not going to suggest you wear an underwire bra yet – that comes a lot later both in size and years. But maybe a special occasion or strapless bra might come your way!"

Bra-fitting ! - It was wonderful and I was learning so much. I knew that I knew so little. I might not have the inner feelings of being feminine as my interest was in being a boy who wore dresses– but my knowledge was zero – or even perhaps negative because of my years of male indoctrination.

Girl 101 – I was at least 100 lessons short of being ready for it.

And yet I was still determined that I was a boy, that I would not become a girly-boy. That I was in no way a ‘sissy’. I was going to marry Gemma if the future didn’t split us up. And I would be a normal boy – apart from a delight in wearing silks, satins and the like.

And there was the potential of Girl 101 and Boy 101 at school – who knew what surprises that might make happen. And what changes as the boys learnt about girls and the girls learnt about boys.

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