There are reasons why a boy wants to go shopping alone.

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“Don’t worry about me, I’ve got to go shopping. I want to buy some things that fit properly this time.”

“Why? Are you buying a set of bra and panties?”

My eyes went wide with shock. I gasped.

“Oh come on. How could you possibly believe that I didn’t know?"

“Erm.”

“What I can’t work out is the level of girl-boy you are thinking about. I think, at least I think I think that you have no intention of becoming a full-time girl and wanting your bits rearranged. I think your penis is quite important to you – judging by the, um, debris on your sheets!”

Erk, gurgle, attempted splutter

“So, taking a guess, it’s either that you want to know some of what it’s like being a girl, OR maybe it’s the textures and colours that attract you – Boy-stuff being so drab and boring. Anything to say yet?”

“Maybe so. Maybe someone has put you up to this – a boy making a dare. No – that might get you trying on ONE pair of panties and proving how daring and so not-gay you were. But buying your own? Buying a bra, or rather another bra , ‘cos the one in your stash is just so unsuitable. Did you steal it from somewhere? That’s just grubby, nasty and actually wrong – and rude too.”

“Still unable to speak, hmmm? Perhaps your eyes flickered when I said ‘buying’. Have you been buying your own things? If so, what have you got hidden away in some private stash. And don’t try to hide it. The Big secret is known by me. There’s very little I can say apart from – I have heard about your type of behaviour. I’ve researched some of it. And some web-clicks take you beyond weird or ugly. I can promise you that I know more than you expect. Probably more than you want me to. I can promise you a few things. Me knowing is NOT the end of your world. Me having you mega-deep-screwed by all this would be an end of some of my world. I do love you. Because you’re my kid. And I want a kid that’s happy even if a bit out-of-the-ordinary rather than one that’s screwed up. I’ve seen the stats for the screwed-up. It’s not happening round here.”

Pause

“Am I getting a bit loud, dear?” She waited ….

And still I had nothing to say. Well, nothing that I thought would be helpful. A seventeen year old boy being caught out buying a BRA. Not a good place to be in.

“Well, bloody right I’m feeling loud. And I’m making sure that I don’t actually imitate the volcano. There should be no secrets between us. Yes? No? It’s not the girly stuff – right. It’s the secrecy, the nearly-lying.. Your behaviour is not acceptable. Yes. You hear me?”

Oh, yes, my hearing was fine. My pulse and my brain might be on high but ….I kept schtum. But I was thinking busy, busy, busy. I wasn’t going to get out of this … but what would be the best outcome? Think, thou scurvy knave. Use both brain cells. Breath-holding was contra-indicated.

“So. Let’s go upstairs and you can show me what you’ve got. Then I’ll know a bit better what might be sensible or even possible next. Mmmmm?”

I didn’t move.

“Come on, kiddo. Let’s go and find out what’s changing in our life.”

I felt dreadful … alarmed … excited … fearful … wondering … hopeful … all at once. Trying to contain all these emotions, all these feelings – I didn’t know if I was going to burst or crumple.

Somewhat numb, I climbed the stairs following my mum. I couldn’t help it. I noticed she was wearing my favourite shiny stockings and the VPL clearly showed the lacy outline of her panties. I couldn’t help it. I was always watching women. Well, more often – girls. And I knew it wasn’t who they were – it was what they were wearing. Oh Golly, what was going to happen now.

Mum must have turned to check that I was following. “You’re looking at my legs again, aren’t you.”

Could this get worse?

“Is there a particular part of the woman’s body that attracts you … or a particular item of clothing. I do need to know if this pastime is going to progress. You can’t do it ‘a bit’. You know how that’s, first of all, never going to give a good result and, second, against my rules. All or nothing should be the way forward. So, let’s find out what you have to wear, what you want to wear and how much we need to budget so that you can be, what, a part-time girl, an all-the-time-out-of-school girl, or whatever is your plan. You do have a plan, yes?”

I still could find no way to say anything. I was thinking furioso. Probably more thinking about what DID I want than I had ever done before. Previous thinking had been more like daydreams and wishfulness-but-lacking-in-concrete.

What did I want. First, I wanted to wear pretty clothes when I wanted to and when I was sure it was ‘safe’. That meant indoors unless and doubtfully-maybe if I ever felt confident enough to go out when dressed. I did wonder if there was a halfway-house. I was very keen to wear panties as often as I could. I did love the feeling of snug when I wore a bra. It didn’t make me feel feminine even if it probably the most feminine-specific garment apart from a period-pad. I wasn’t unaware of the differences between boys and girls. I knew about sex – even if putting a condom on a cucumber is barely an essential life-skill.

Mum had asked another question. I had to speak my first words in some minutes. “Sorry, Mum, I have no idea what you just said. Can you repeat please.”

“Are you wearing panties right now, was what I asked.”

“No, I’m not.”

“Ah, perhaps communication has begun. How many pairs of panties do you have? How do you get them washed? And a larger question, sorry, no an actual demand – show me what you’ve got.”

“I’ve got six pairs and I wash them out every time I wear one. Rinse and towel-wrap to dry then hang in my wardrobe overnight. I’ve got most of my things at the base of my chest-of-drawers.”

“What, hidden beneath the bottom drawer?”

“Yeah.”

“Wrong answer. I don’t like ‘yeah’ and quite clearly you’re not looking after your extra clothes properly. You’re going to learn to do much better.”

“You’re going to let me keep my things?”

“Yes. I’ve been reading -and thinking about this. All the sites make it very obvious that if a boy does get into dressing, then he’ll keep doing it unless and until there is a need to change the habit. This might be his whole life going down the pan. It might be assault or an equivalent while dressed. It could be something else. Maybe getting a girlfriend would change something. It is not at all clear in the very many pages I’ve been looking at. One thing is clear – the depression that can occur when dressing is prevented is not good for the child. The suicide rate and self-harm rate that occurs is so many times the rate for the so-called normal kid.”

“Oh.”

“That’s about the most limited response I’ve ever heard from you. ‘Oh’ doesn’t say very much apart from you haven’t done any significant research yourself. Surely you must have found out that you’re not the only kid who dresses up?”

“Oh, I know there’s others. I just don’t actually know anyone. I don’t know anyone who knows anyone … but then what I do is not easy to talk about.”

“No, talking about being different sure isn’t easy. I’d agree with that.”

“What? What sort of difference are you talking about. I mean for yourself.”

“N’n’n’n’no, we’re not talking about me. Let’s say it was someone, actually two someones I used to know. And their difference wasn’t about being boys who dressed up. Okay.”

“Erm, okay. I won’t press. I may wonder though.”

“Wondering is okay. Thinking would be better. But we’re drifting off topic. Let’s see these clothes.”

Gradually my stash of pretty, well, used-to-be-pretty clothes made a set of untidy piles on the bed. Lifting out the bottom drawer was a well-practised manouevre. Underneath was a gap about four inches wide where I had built a couple of compartments. My six pairs of panties. The box of pantyhose. Two skirts, three blouses and a cardigan. I dug out my only dress from the back of my in-bed drawer. I’d built a sort of interior wall which made a second stash-space of about 8 inches.

“And where did you get these things? Mmmm?”

“Oh, I did buy them all. In the supermarkets and at the thrift-shops.”

“I’m not surprised they don’t match in any satisfactory way. You may know about colour and texture – or think you do. But you don’t learn well just by looking or watching. Now I’ve got some questions. Sit.”

There was a pause while we arranged ourselves in the two available chairs.

“Now, I guess you’ve been thinking. I’ll ask some simple questions? Are you gay?”

“No. I like girls, or at least I would like to like girls. Boys … no, no, no, I don’t think so.”

“Are you bisexual?”

“No, again, I really don’t know. I think my sexual activity is sufficiently not-yet-active that what there is, mostly, is just in my mind. Not yet real. Okay?”

“How often do you dress up? How often would you like to dress?”

“I do like panties. I’d like to wear them all the time, really. But other things, that’s not often. I’ve only worn the dress twice. I wear the blouses and the skirts maybe once a week.”

“And the bra. Not that it’s the right size anymore.”

“I wore it a few times but it never looked right – I tried stuffing it with socks and so on. I saw some breast-forms at the supermarket and did wonder about them. I guess I didn’t like the risk of the checkout girl, well, y’know.”

“I can guess, honey. I remember wanting to look like I had bigger breasts, until I wanted them smaller. But that was so many years later. I’ll give you some help with all this. Mind you – I still don’t actually approve of you dressing. Not actually because of the dressing – but because it makes you too easily labelled as ‘different’. And ‘different can mean dead’.”

“I’m not planning that, Mum.”

“Honey, it ain’t YOU that’s going to make you dead. It’s you that makes the choice to be different. It’s THEM who are the people who can make you dead.”

“Oh. Again, I guess. But trying to be helpful. I’d like to be able to dress at home quite often. Not every day, mind you. Though that might change. Can I dress at the weekend? That’d give me a better idea of what I want?”

“Would you want to be dressed outside the house? For church, maybe?”

“God, no. Just in the house when there’s enough time. I want to be relaxed about all this, not stressed out of my skull.”

“What do you want to have in your wardrobe?”

“Does that mean you’ll help me?”

“Ain’t nobody here in this room but you and me. And the evidence on that bed suggests you haven’t got a clue about dressing as a girl, looking like a girl, feeling like a girl, let alone being a girl out for the day with her mum. Does my honey have a clue?”

“Erm, oh.”

“Let’s take a break. In the morning I want you to tell me what YOU think we should go shopping for. Obviously you need panties that fit. You need a couple of blouses and skirts that fit and match. You’ll need a bra otherwise the blouse won’t hang right. And with the bras you’ll need forms. Will you want a dress too?”

That evening I went to my computer and accessed a sub-directory. Of course I’d given it a meaningless name, I’m not dim. It was filled with pages from the net. Dresses and just every thing I’d found and enjoyed over the last 6 months. Other directories had older stuff that I had decided was less fashionable. I had a sub-sub called favourites and that had about fifty pictures. I printed them all at four to a page and took them downstairs.

“Here, Mummy. I’d say that your list does cover a lot of what I’d like. And you can see some of what I’ve liked recently. And it would be enough for anything I can see myself doing.”

“What’s your girl-name, honey?”

“Would you guess that it’s actually now going to be Honey. I was thinking of myself as Laura for a while but actually I love you calling me Honey. So can I choose Honey, please.”

“Oh, Honey, that’s so neat. Yep, Honey it is. Does Honey want anything else?”

“Can I have a nightie as well.”

“That won’t break the bank. I’ll let that one pass. And when we go to the shops we might see some more things you’d want.”

“You want me to come to the shops with you …… looking at girl’s clothes. That’s going to look, um, no, it’s a bit risky isn’t it?”

“There’s a risk. But everything I’ve read says that if you behave as if you have every right to be doing what you’re doing in the place and time you’re doing it, behaving with confidence and certainty … it’s usually okay.”

“Are you sure?”

“That’s the way it’s going to be, Honey. Get dressed. You can wear panties if you want but that’s all. We’re going to be out for a good few hours.”

“Are you sure?”

“It’s what is going to happen. If it makes you happier, we can go over to Mosstown rather than here is Donaldson.”

“Yeah, that’d be a good idea. Less people likely to know me or you. Yes, please.”

“Ten minutes – at the door. Okay.”

“Yes, sir.”

“Give over, Honey – or things’ll get sticky.”

“Oh, puns is it now. That’s beeing silly.”

“Enough. Get ready, pronto,”

I sat there while a few minutes passed. I didn’t spend all that time deciding which pair of panties to choose. I was dithering about whether I really was going to go shopping to pretty colourful girl-clothes for ME. Or whether I would bottle out. I did know that doing that would probably mean being told ‘if you can stop then you’ve stopped and we’ll have no more of this dressing. I didn’t want that. So …. decision made. Honey was going shopping.

At the door, Mum did something I could never have expected. She gave a tiny spray of perfume onto my collar saying ‘Now you’ll feel so much more girly. I think it’ll help.”

I’d never thought of perfume before. I’d never dared. It made me feel … wonderful. And just that bit extra girly. Now I really wanted to go shopping. With my Mummy.

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In the car, we talked about what I liked. I suggested we sit in a café and I’d say what I liked and even what I didn’t. I wanted to show that I was looking for somewhere near ordinary-with-a-bit-of-style. With what I had scrounged together, I knew I didn’t have a style yet. I liked the certainty of showing a feminine image with skirts and a dress. But I knew, from lots of watching, that I wanted some cute culottes, maybe even something towards a romper. I saw one girl wearing a really cute dress until I saw from the back it was shorts-style .. thus a romper. I wanted some stylish trousers, calf-length chinos maybe I knew I wanted colour and textures that were really not allowed for the typical male. It was going to be interesting to see what we found.

So, we sat in that café. Near a couple of clothes shops – with lots of teenage girls going in and out. Some women too with their offspring. For a moment, I thought one of them looked awfully boyish – but I changed my mind when I saw the beautifully-applied makeup. That had to be a girl.

“Honey, shall I keep some notes or do we do it all from memory?”

“Not too many, or it’ll feel like a school lesson, yeah? But there’s bound to be things that I’d forget otherwise.”

We’d been doing our watching for about an hour before we actually got into the shop. By now it was lunchtime so most of the customers were now happily at their local feeding-trough. There were still some people around as well as a few assistants. Most of them weren’t doing any actual assisting but busy chatting to each other. None were using phones so we guessed that there was a shop rule against them.

Mum didn’t hesitate. We’d already agreed that shopping was going to be from the inside out – so panties and undies first, onwards to outerwear and shoes.

To my surprise, we didn’t spend long on the panties. Mum had measured me in about 47 different ways and simply said “get a pack of day-to-day panties, white is better but coloured if you really want. You can get 4 or 5 pretty ones too in size S. We’ve got more important things to get next. A bra or two, of course. And onwards.”

We’d talked about how I should behave. I was worried most if Mum had insisted on a actual bra-fitting. If I got that far undressed, at my age, complete lack of boobage would make my situation very obvious. She’d said that in the shops we were going to a fitting would be rare. She had a good idea of what size would suit. We’d buy, find a suitable place to get changed so she could check, then either keep or return as necessary.

We chose, well she chose the size and I chose the look – we chose three bras. And checked that returns would be accepted. They said the bras had to have their labels and be obviously barely-used and preferably within 2 or 3 days in the box and so on. It felt a bit icky that something so intimate and personal could be returned but I wasn’t going to make it more difficult. But I was so looking forward to having my own bra that fitted me.

xx

After lots of giggly over-excitedness, we bought three bras, in sets with matching panties. The prettiest was pink satin with black trim. I'd show a picture if I could.

As we were leaving that area, I saw a lovely nightie and we bought that too. Mummy – (sometimes it felt right for Mummy, sometimes for Mum) suggested I had a set of long, short, sleep-panties and a coat. After a bit of effort we found the necessary. All in white with a pale pink trim. I was looking forward to bedtime now as well.

The geography of the shop took us to shoes next rather than dresses or skirts so we looked briefly at the enormous range. I had my feet measured by a gadget which said size 5 – no real assistants available. Then Mummy said that a heel of an inch and a half or maximum 2 inches would be it. But she said flats or ballet shoe-type would be the first thing. Not my usual trainers unless the choice was obvious.

I never realized how expensive some of this girl stuff was when you bought new. But Mummy was not too obviously worried. She let me have some flats in black, white and pastel-pink, and one pair of ballet-type shoes, and finally one pair ‘to learn with’ of black and tan inch-and-a-half heels. I rather wanted the two-inch block-heels but I was told that they would just lift my legs but wouldn’t teach me how to walk and balance properly. I was allowed to try them but they did feel quite heavy on the feet.

So nearly a dozen panties and three bras in one bag; 4 shoes in another. And onwards.

Mum commented as we walked, “It’s a bit of a shame you aren’t getting your First pretty Panties, your First Bra and so on.”

“I didn’t really think I could say, Mum, can you help me buy panties, bra and so on. I’ve read about it being steps on a Rite of Passage for a Mum and Daughter. But this ain’t so. I’m just a boy buying clothes which the Mob, Them, would most likely disapprove of me having, let alone wearing.”

“Honey, I’m not dim. But you’re all I’ve got. And it’s true what you say. But it’s also true that neither of us can actually do the First Bra and enjoy that moment the way it should have been. But let’s concentrate on the positives. Let’s find some pretties for you.”

I need to point out that, for onlooker purposes, my Mum is quite short so it wasn’t massively unlikely that she would be looking in the girl-focussed shops rather than in the women’s shops. And I’m not a big hulk. I’m five foot seven and fairly skinny. Almost without thinking, I’ve let my hair grow quite long – the schools have mostly given up on the hair-rules. Probably 90% of the girls have beautiful long hair; I don’t know how the peer-group pressure prevents any of them going for a modern fashionable bob or whatever – but I love it that they have long hair. It’s one of the things I’d love to have.

Hair-wise, Mum had brushed my hair so it looked at least non-boy. It did make me feel quite a lot more at ease with this exciting yet almost-frightening experience. The occasional waft of that perfume was a gorgeous reminder of what could be.

I was beginning to relax, well, as much as I could – and that was more than I expected. But you can’t stay at panic-mode for very long. Unless you’re my mother’s sister Jane. Wow. And grudgeville too – till death do us part. Not nice. Keep away from all – I mean ALL - the trigger subjects and she was actually quite fun really.

But I didn’t dare to get too relaxed. I somehow knew that if I actually started joining in with the looking, touching, feeling, trying and buying then there would be more risk. Attempted-confident was the best I was hoping for, minimum risk and all that.

But it was so difficult not to get involved. I wanted to do the touching, testing, trying. And after a while that’s what I started to do.

“This is pretty” Mum said, holding up a white blouse with mid-size ruffles down the front and flounced sleeves. Just at the exact moment, I held up another one in red with gold trim and said ‘This is nice.”

We both laughed, or actually it was a giggle from her and a sort-of-giggle from me. It was truly a special girl-moment.

“Both?” she said and I nodded-grinned my thorough agreement.

Soon we were having such fun. The risk of being caught was out of my mind. Then I saw the girl from before. There was something about her that really caught my attention. But then Mum called and I was swept up in looking at a really cute romper very like the one the girl was wearing that we saw earlier. However unsuitable, I really wanted it.