H Is for Helen

Then I caught sight of the pair of shoes, probably Marion Carlisle's, which I'd noticed a few days earlier. Though I knew women's feet were in general smaller than men's, these shoes didn't look too small. In fact with thin tights on instead of thick socks they could even fit. I thought of Mr Carlisle's reaction. These weren't something he'd bought for me in order that I could feel more comfortable, these were his daughter's shoes.

Yet I really did feel they would do the job, enable me to wear the tights. And that was the point after all, wasn't it? So I'd feel more relaxed despite my medical condition, and be able to study more effectively. Since Dr Weston had said she couldn't help my skin condition with medication, surely I was justified in trying other methods? I had convinced myself.

I put on the shoes. They were, to be honest, just a little tight. But then so were my trainers, I'd almost grown out of them. Mum had mentioned something about getting me some new ones only a few days earlier. I stood up. I walked round a little. I looked down. I was amazed.

My feet actually looked - attractive. I'd never ever thought that of my feet before but the combination of the sheer tights and the shiny black high-heeled shoes, I really did think they looked nice. Not just any old pair of feet in trainers. I realised that what I was looking at was basically a pair of female feet. I mean, you never saw male ones like that, did you? And it was that aspect of the whole tights-and-high-heels thing I found attractive.

"You OK, Harry?" called a voice up the stairs. "Come on, time's a' going, I need to sort out one or two things with this Biology of yours."

"OK. Coming."

I entered the room nervously. Basically it was the shoes. I'd been presumptive in trying them on, maybe I'd gone too far. Mr Carlisle and I had a good working relationship, I didn't want to spoil it.

"So how are things? You've got the tights on, I see. Oh my! You've got Marion's shoes on too."

"I'm sorry, it seemed a good idea. The tights are fine but they felt wrong with my trainers. I hoped you wouldn't mind."

"I don't mind at all, Harry. They were to throw out anyway, I'd forgotten about them. Marion told me about them before she left, she says they're the wrong size, not labelled correctly. They're too big for her. If they help you, that's fine. OK now, this Biology, come on. The first section is good but you've got your head round something totally wrong in the second part. Look here."

I looked. We discussed. I studied. And I like to think I was doing well. Maybe Mum had been right, I was learning stuff better with a home tutor than I would have done at school. OK so it was only eight hours a week but I did my home-works and so on. And we carried on like that for four or five more weeks, me changing as I got to Mr Carlisle's house, doing my studying, changing before I went home. And my breasts? They seem to have stabilised. And the skin condition? Well, to be honest it did clear up from my body, but I'd got used to the routine, and really in a way I liked the underwear.

But it didn't clear entirely. It was mid-November, just after the half-term break (which was really boring for me, stuck at home on my own, no lessons, no mates to visit except Jake, my one really good friend). During the week, for some reason, the skin problems returned to my face. Very embarrassing, I couldn't effectively hide it at all. Just walked to Mr Carlisle's house with my head down yet again, I was getting used to that. No calling in at shops or anything, just straight there and straight back afterwards.

"Doctor Hill has promised me she'll give me some medication which should help in a couple of weeks. She's reluctant," I told Mr Carlisle one morning "because my - other problem - seems to be slow in subsiding, in fact - they haven't started yet."

"So you're stuck in - entirely?"

"Yes"

Mr Carlisle carried on the lesson, then stopped about half an hour early.

"Harry, I just wonder. Maybe there is something more we can do to help. To hide the problem, just for a couple of weeks maybe?"

"That would do, certainly."

"Well, it's a rather strange idea but I do think it might work. Can I ask you to try something for me? Come upstairs, I want to show you something in Marion's room. "

We went up, it did seem a little odd, this was the first time we'd both been in there together. Since I did my own changing in there I regarded it to an extent as 'my' room even though obviously it wasn't. Mr Carlisle asked me to sit on the chair, the only chair in the room, and then opened one of the drawers in the dresser.

"My daughter, Marion, she has rather a sensitive skin too. Not as bad as yours of course."

He stopped.

"Oh dear, Harry, that sounded awful."

"No, that's all right." I wondered where this was going.

"So she uses a very light form of make-up, something which just does the job, enhances her appearance, that sort of thing. In the sort of job she's in, in PR that is, she has to look good. Well, I just wondered if you'd like to try something like that yourself. Just to see the effect, it's really a good quality product, dermatologically tested and all that. It might help."

I thought for a moment. Makeup?

"So what would that involve, Mr Carlisle? I'm not sure it would help. And I'm certainly not sure I could do it properly."

"OK Harry, let's leave it for now. How about we try it just a little at the start of tomorrow's session? You change now, it's almost time. I'll look through these drawers and see what I can find. OK?"

"OK then." I said. "I'll try anything once."

The next morning I went straight up to change. Then Mr Carlisle came in, he brought another chair and sat beside me.

"I don't want to spend a lot of time on this, just a quick go. OK?"

"Sure."

He had arranged quite a few bottles and tubes along the dresser. He started with one flesh-coloured tube, squirting the thin paste onto a sponge and spreading it over my face.

"Here, Harry, you continue. It seems to be covering, and it doesn't look too bad, does it?"

Indeed it didn't. On the one hand it did cover the irregularities in my skin very well, and on the other it gave my face a pleasant sheen. I took a minute to smoothe it into place, then Mr Carlisle took a brush and spread some powder over some areas of my face, basically to give the rather flat surface some sort of relief. Then he got a bigger brush and some deeper pink powder.

"And just a little blusher, I think. OK?"

After that he got a pot of deeper pink paste, basically a lip colour, and applied it very carefully with a brush over my lips, finishing by coating them with a gloss liquid.

"Now, I have to admit, Harry, I think that looks very good."

I looked. I rather liked what I saw. My skin had become rather badly marked over the previous week, Dr Weston had said it was a sign that things were finally coming to a close.

But the effect of the make-up was to cover all the flaws, very effectively. I knew I couldn't go out in the street like that, Mr Carlisle agreed, but he was quite happy for me to continue with our studying with me made up. I didn't do it on the next few days, but at the end of the following week I suggested I try the make-up again.

"You want to do it yourself?"

So I did. I managed very well with the foundation, the highlighter, the blusher, then the lip-colouring and the blusher. The result looked - quite good, I thought. Finally I looked in the wardrobe. OK, so Marion's shoes were a little smaller than mine, what about her clothes. I took off my sweater and trousers, and slipped on a pair of her jeans. They were tight, yes, but wearable. I got a sweater too, with a V-neck, again tight-ish. I liked the way it felt. I looked in the mirror. I wasn't hiding my breasts, my cleavage any more. I was revelling in it. But - what would Mr Carlisle say?

I walked out of the bedroom, down the stairs, and into the dining room.

"Well, Mr Carlisle. What do you think?"

He looked at me. A strange sort-of glint came into his eyes.

"Well, Harry. I see you've decided not to hide things any more."

"Well, just here, Mr Carlisle. I mean, just for today. I couldn't go out looking like this, obviously. But just for in here, I borrowed some of Marion's clothes. I hope, that is, if you don't like ..."

"Harry, it's fine. Really. You look nice. Will you excuse me for a moment?"

He rushed out. He looked weird, like that first time I'd tried on the purple bra. Somehow it wasn't the reaction I'd expected. I sat and looked at my books for a couple of minutes before he came back.

"Harry, you look great. Feel like some studying?"

"Definitely."

We actually got through a lot of stuff that session, and in the next couple of mornings though I didn't go quite so far with the dressing and the make-up. But I just felt good. The whole combination, the lingerie, the jeans and more than anything the revealing sweater, they all contributed to a feeling of well-being. We both worked, hard, tutor and student, we made a lot of progress.

Then, a couple of days later as I was going to leave, Mr Carlisle surprised me.

"Harry, I know you've been working really hard recently but we do need to sort out something. Your Geography is coming along really well but there's a problem looming. You have a Project Study to do."

"I know that. I had thought of using the High Street in town as an example, looking at the building styles and so on, that sort of thing. I thought I'd mentioned that?"

"You did, Harry. But I've been in touch with your school. The teacher there wants to get all the projects started before Christmas. And that should really include yours."

"So what does that involve? Internet searches, I thought. I could do it all on PC."

"You could, Harry, but I have to tell you the examiners are not so fond of Net-projects. They like you to actually get into the real world."

"Shit."

"Harry!"

"Sorry Mr Carlisle. Maybe I could do it in the evenings?"

"Yes you could, but you really need photographs, you should do it in the daytime. There is a way, Harry. Please don't be surprised, but from what I've seen recently I think you might be able to get away with it."

"Yes?"

"Harry, in many ways, your figure specially, you look as much like a girl as a boy. I don't think it would take much for you to be able to carry it off. I could drive you into town, then you could spend an hour or so on the High Street. With your notebook, and the camera on your phone. You can see what you need to see, get all the data that is and the photos. Then do all the analysis the next day. If you're prepared to do it, that is."

I'd listened carefully to the last part of what Mr Carlisle had said, then I realised just how he'd started the sentence.

"You mean - dress as a girl, a woman. And go out?"

"Yes, dressed like you are now. Not in that big sweater, those jeans would be OK though. It would just have to be for an hour, Harry. I can't do the actual research for you, it's your project. You have to collect the data yourself. How about next Monday? My other student won't be with me then, she's - er - had to go away for a while. We could spend a bit more time on it then, maybe do some of the analysis later, even."

"Do you really think I could do it? I mean, it sounds a bit extreme really."

"I'm sure you could."

I thought. It was a silly idea really, but ....!!

At the end of the week I had my regular medical assessment, more tests and measuring. It was Dr Weston again, she sat down with me after all the tests.

"OK Harry. I really do think we're coming to the end of this. The swellings have just about peaked and your skin is beginning to clear. Now it won't happen instantaneously but things will change quite quickly. After the next week or so I imagine you'll notice a decrease in the swelling. You might consider a bigger bra in the meantime, in women's terms you are pretty massive right now. Look, let's actually measure the cup size. OK, lift up your arms."

She fed a tape round under my swellings, then repeated over the widest part. She looked at the tape, her eyebrows lifted.

"I think, Harry, even just for a few weeks, you definitely need a bigger bra!"

I didn't tell Mum and Dad what Mr Carlisle and I had planned. Obviously. I mean I did tell them I was going to be out studying all day, just said I had to do a special project, probably I'd go to the library in the afternoon. Which was partly true. As I was leaving the house, Dad thrust a package into my hands.

"Just a small present, Harry, for your tutor. It's only a bottle of wine, not a lot really, but we are all grateful for his efforts. You really have made progress, I'm sure, and an awful lot of it is down to him. Oh, and Mum and I may not be in when you get home, Harry. We're celebrating our anniversary. We're having a long lunch at the 'Regency'. Will you be OK?"

"Sure Dad."

I arrived at Mr Carlisle's house a little early. The thought of actually going out in public was beginning to disturb me. I hadn't done that for so long apart from my brief excursions, head down, four or five times a week. And in Marion's clothes too, that caused me concern as well. But at least it was in school-time, none of my friends would see me. I hated to think of the teasing I could get if I got recognised.

It really hadn't occurred to me to ask Mr Carlisle quite how he knew about make-up, and indeed how he was so good at it. That first time he'd shown me how to do it had surprised me. And I was no less amazed that morning. After I'd changed into my usual lingerie, and put back on my old trousers and sweater, he began to augment the basic make-up I'd done.

"This is probably the best mascara colour for you, Harry. You can get it in all sorts of dark colours, this one is a very deep blue. I think it will suit with the sort of eye-shadow You'll be wearing. ...... OK now, hold still, let me do your eyeliner ---- and just a little eyebrow pencil ... there, that looks OK. Now I'd thought of a rather darker lipstick, what do you think?"

What did I think? How the hell was I supposed to know?

"OK Mr Carlisle, you choose, I think that one does look all right."

He very gently and meticulously, with a brush this time and a small pot of colour, spread the deep-ish red paste over my lips, adding another slightly darker colour at the edges.

"There. That's a lip-liner, it marks out the edges quite clearly, but I think you need quite a thick lip-gloss over the edges. That will look really good."

I looked in the mirror. Yet again I was surprised, not just at the fact that I was clearly wearing make-up, but also that I was doing so very overtly this time. It wasn't just a case of trying to cover over my skin blemishes, which had indeed receded in the previous few days. But I was wearing quite heavy makeup, obviously so, but of course if people saw me and thought of me as a girl or a woman maybe that would be OK.

I inspected my reflection. I was just going to make a comment about my hair. It was just a little long by then since I hadn't dared go to have it cut for several months. But Mr Carlisle was ahead of me. I noticed him getting something from a bag beside the chair.

"Right Harry. The crowning touch, literally. This should do the trick."

He had a wig in his hands. Oddly enough I'd not really thought about that.

For some reason my own thoughts over the preceding few days had been concerning my own problems, the breast-like swelling, the skin blemishes and so on, and the steps I'd taken, with Mr Carlisle's encouragement, to overcome them or hide them. I hadn't really considered my hair. In some way I'd just assumed having slightly long hair would be OK, as far as me resembling a woman was concerned, that is.

"I have to admit, Harry, that I bought this some time ago. Somehow I knew you were heading in this direction, that in some way you'd need to resemble a woman more closely to be able to go out in public. Your natural hair has a reddish tinge. I know it's mainly mid-brown but there is some red there, so I thought a wig with longer hair, red hair really, would look OK. Are you ready for this, then?"

Mr Carlisle slid the wig on from the front, trapping my own rather unkempt locks invisibly under the 'cap'.

"It's quite a cheap wig, really. Even so I thought it would look realistic enough, that it could make quite a difference."

He took a brush from the dresser and smoothed the long strands down at the sides and the back of my head, returning to briefly tease the fringe into place. He stood back.

"There."

I was impressed. Very impressed. I actually looked female, from the neck up at least. The make-up and wig combination worked well together, looking back at me from the mirror was - a woman. OK, a woman, not a girl, I reckon the overall effect of the wig and the make-up had put about five years on me, maybe as much as eight. Definitely a woman.

And as I looked downwards, to see the baggy shape of my sweater and thought about its contents, when the image of my 'breasts' came into my mind, yes, definitely a woman.

"I've put the top and the jeans in the wardrobe, Harry. If you want to change now? I'm just going downstairs to sort a few things."

And, sounding very 'squeaky' I thought, somewhat excited by all this and yet again seeming not quite right in some way, Mr Carlisle left me in 'my' room. To finish my dressing. My transformation, from swollen slightly spotty young man - into a woman. I took the hanger with the jeans and the sweater from the wardrobe, then looked in there again. Why wear the same things again? Why not something else?

By now I was sure Mr Carlisle wouldn't mind, and Marion wasn't there to object, she was half a world away. I inspected the hangers. Quite a few of the things in there were not really suitable, pants which I knew would be too tight, sweaters too, but at the end my eyes lit up. I put the jeans back.

There was a suit. A sort-of business suit, jacket and trousers, which looked as if they might fit. I took the hanger out and inspected it. The jacket was a deep blue, maybe it could work, after all I was wearing blue eye-shadow. It had a somewhat mottled appearance, not just plain blue, a bit of a silvery glint to the fabric. Indeed, though I was in no way an expert, it looked quite expensive to me. I looked at the label. It was a designer I'd actually heard of. Not one of the top-notch names but someone reasonably famous. Certainly it would have been expensive. I could wear the jacket over - I reached into the wardrobe again - that blouse. It was a creamy white colour, very shiny, maybe even silk, long-sleeved and hopefully not too tight. Which was good since it would have to cover up my bulging boobs.

I took off my big sweater, and slipped the blouse on. Now THAT felt good. I was sure it was real silk, I really didn't know why Marion had left it behind after she'd moved. And it fitted too, quite snugly over my shoulders. It had slightly flouncy sleeves and amazingly it wasn't too tight over my 'breasts'. I was a little worried when I realised my bra was clearly visible through the fine light-coloured material but if I was going to be wearing the jacket over it, that should be OK.

I picked up the matching pants and then noticed - there was a button missing from the waist-band. I couldn't wear them, I was SO disappointed. I mean, the jacket was fine, I checked that, nothing wrong with it. Maybe this was why Marion hadn't taken the suit with her, at least. I still wondered about the blouse, that seemed fine. But - no trousers. Slacks. Pants, whatever. OK so the jeans I'd had on the other day would have to do.

'Pity' I thought, I really had hoped to wear something smarter.

Mr Carlisle had hung the jeans up at the end of the rail. I was just reaching out to get them when I realised there was a skirt hanging next to them. A skirt? Well, why not? If I was going to be pretending to be a female so that I could get my project data, I could wear a skirt. Of course I could.