H Is for Helen

"But Mr Carlisle ...." I tried to interrupt.

"Harry. Seeing you dressed and made up like that, in your short skirt, I was sexually aroused. And that's not a good thing for a tutor to be with a student. I knew I had to go ahead with our outing but - since then - I think things have begun to get out of hand. I'm afraid - this has to stop."

I got up and walked around a little. I had to think. This did explain a lot. How Mr Carlisle had been able to help me with the make-up and so on, how he had been able to do it so well. And the frequent looks he'd given me, maybe not quite the looks from tutor to student. Basically, he liked 'Helen'.

It was then I realised how my own slant on recent events had changed. I liked being Helen.

"Mr Carlisle. You said you don't really trust yourself."

"Yes. That's right."

"Do you trust me? I mean, you're older. Older and wiser, as they say. And maybe with all the transvestite stuff I didn't really realise what was happening. But - I like being like this. Today has been a wonderful day, maybe except for seeing Mum and Dad in town, that was scary. But just being out, and being looked at, I've enjoyed it. So much. And I may be younger than you but I do know what I'm doing. Maybe it would be best if I stopped dressing up, especially if my symptoms are going to subside. But I'd still like to continue the sessions next term, at least until I can go back to school."

Mr Carlisle sat thinking for maybe half a minute.

"OK Harry. I won't ring the school yet, we'll see how the next few days go."

I turned and went up to Marion's room to change. That evening Mum and Dad were late-ish home. I did myself a snack. I was just sitting, thinking about how things had developed, waiting for them when Jake turned up at my door. Jake was just about the only real friend I could trust in school. He was the only one I'd told about my own problems in any sort of detail. But even with him I still wore the baggy sweater. And I'd never shown him my MPMs.

As soon as he arrived I realised. The image of my own earrings, worn that morning, for the first time, shot into my head. Or rather Marion's earrings.

"Jake! You've had your ear pierced!"

"OK, Harry. Cool, isn't it? Rib me if you like, but it worked."

"Worked?"

"Yeah. Real cool, it worked on Holly. I'm taking her to the Christmas party. Friday. At the 'Dragon'. Do you think you'll be able to come?"

I'd known he would ask me that. Jake kept going on about how my mates would understand but I knew that wasn't entirely true. Like in any class, there are some all too willing to poke fun at anyone different, whether he has thick glasses, or he's black, or - whether he has big swollen tits. It just wasn't on. I still had to stay out of sight.

I changed the topic again.

"So - where did you get your ear done? Was it painful?"

"Only a bit. My mother did it. Cheaper that way of course."

At which moment Mum and Dad appeared.

"Hello Jake, how's things?" asked Dad.

"Fine, Mr Davies" replied Jake.

"OK at school? Did you get your Geography project started, Harry's been doing his today?" added my mother.

And, as she did so, for a reason I just couldn't see, my Dad smiled as she asked.

"Sure, I got it in last Thursday. No problem."

"Harry, you were doing yours this morning with Mr Carlisle weren't you?" queried my Dad.

His smile grew.

"Er - yes."

What was this about? Surely he hadn't ...... No, of course not, his reaction would have been much more explosive. But something was going on I didn't know about.

"We reckon Mr Carlisle has had a busy day, Harry. We saw him in town this afternoon, after we left the restaurant."

"Oh. Did you?"

Maybe they'd just seen him, not noticed me.

"You remember he said he has another student, Harry. A girl, I think he said. Well we saw her. She was obviously doing some project or other, like you. She had a clipboard, you know, a bit like yours. They were just off the High Street."

"Was she?" I replied, rather weakly, not at all sure where this was going.

"Pity you've not met her, Harry" continued my Dad, smiling even wider now. "Drop-dead gorgeous, she is."

"Jim!" exclaimed Mum, not too sure about her husband saying things like that, clearly about a young woman or so he thought.

"Well, she is dear. Very attractive, at least. Long red hair, tight top, short skirt, you'd like her, Harry. And gorgeous tits"

"JIM!!"

My mother was almost shouting. But she wasn't really embarrassed, she was smiling too.

"Jim, I think we'd better change the topic. Jake, I've just noticed, you've had your ear pierced."

Jake told her about it, about his Mum doing it, said it hurt a bit but not a lot. He didn't mention Holly Tomkinson. I was still recovering a bit from my Dad's comments, I was really glad I'd spotted him and Mum in town. Clearly he had noticed me and Mr Carlisle. And if he'd got up close to us...... I hated to think. I moved onto the new topic of conversation, suddenly keen to take advantage.

"Maybe your Mum would do mine, Jake. Do you think?"

I waited for my own parents' reaction. They surprised me, I might have expected some hassle. I struck while the iron was hot. Within forty-five minutes I'd gone back with Jake to his house, up the road and round the corner, chatted with his Mum, had BOTH my ears pierced and small 'sleepers' put in, and walked home again. It was dark by then, I was OK with that, specially with my big padded coat on. No problem.

Mr Carlisle noticed, of course, the next morning almost as soon as I'd walked in. But he didn't make any adverse comment, just muttered something like 'very nice'. For the first time in several weeks I didn't go up to Marion's room to change or anything. And we didn't say much about the events of the previous day at first, not about the subterfuge I'd used in order to collect the data for my project. We did deal with the data of course, even though I was supposed to be doing Biology that morning. But he did say something about ten minutes before we were due to finish, we had in fact reached a suitable stopping point.

"Harry, I think you were wise, not to dress up or anything today. We have to get things back on a professional footing, there really could be problems otherwise. Please, what I said, about my liking transvestites and so on, you won't mention that to anyone, will you?"

"No way, Mr Carlisle. Nobody at all, not mates, not family, nobody."

I wondered whether to say anything about my Dad's remarks. I decided I should. He looked rather horrified when I told him, then grinned at the 'gorgeous tits' comment.

"Harry. I think we got away with it. And, though I shouldn't say this but it was worth it. From what I've seen that's going to be a damn good project, maybe an 'A'."

Dad was pleased when I told him that.

"Well done, Harry. This tuition thing seems to be working very well. Finish on Thursday, isn't it? Oh yes, while I remember. On Friday Mum and I are off out again. For the night this time. Remember that hotel we had lunch at? They've sent us a special offer, so we're re-celebrating our anniversary on Friday, which is the actual day. And staying there overnight. Will you be OK on your own for the night?"

Friday. So I'd be on my own. Mum and Dad having a sort-of dirty night of it reliving their wedding night, Jake and everyone at the 'Dragon', and me at home with the TV. Oh well.

"Sure Dad." I could have said more, but I didn't.

A couple of days later, at the end of our session, Mr Carlisle and I had sorted out the stuff I was going to do over the Christmas holidays.

"Maybe you'll be - partly at least - back to normal by then. Physically, that is. Anyway, Harry, have a good holiday. See you in January."

Mr Carlisle came to the door with me. I was just about to go. But there was something else I'd been thinking about, wondering whether I should say anything. I decided I had to. There may never be another chance. I turned to face Mr Carlisle.

"Sir. Just one thing."

"Yes, Harry."

"I enjoyed Monday."

Mr Carlisle paused.

"So did I."

I hesitated again.

"Look, sir. You said you like transvestites, you've looked at web-sites and magazines and so on. Well. How would you like - to take me out? "

I stuttered. No. Not that, not go out with Harry.

"I mean - take Helen out. On a date, just out to a pub maybe. Would you like to?"

"Well, I'm not sure about that...."

"Oh go on, Mr Carlisle. Look, on Friday Mum and Dad are away for the night."

I went on to tell him why, it wasn't really any sort of secret. And I told him about the party. The one I couldn't go to. The one where Jake and Darren and George would be getting very tipsy, and Jake would end up feeling up Holly's mammoth jugs, at least he hoped he would. And there was me, with the television.

"So. Friday. How about it?"

He looked at me. He thought. I mean, I KNEW he wanted to but he was hesitant. A big step, and with a student too.

"Well, since Marion's due back on Monday, this would be the last chance. The only chance really."

"Marion? Your daughter?"

Quite why I asked that, I just don't know. He was obviously talking about his daughter. After all, she is the only Marion we had in common. In a sense.

"Yes. She's flying in on Thursday night. I think she's staying with a friend near Heathrow for a few days. "

He stood still. He was thinking.

"OK Harry. You're on."

I was pleased. Obviously. Like I said, this may be the last chance. And going out on Monday had been SUCH a thrill.

"OK, Mum and Dad are off about half-seven. How about I come here at half-eight, you can help me to do my make-up again, and I can wear that top and skirt again if you like. We could get to a pub about half-nine or ten just for half an hour, maybe an hour. How does that sound?"

"You've thought this through, Harry, haven't you? I bet that's why you had both ears pierced, so you can wear one of Marion's other pairs of earrings."

"No, sir. Not at all. Sure I've been thinking about this, but only since Dad told me I'd be on my own tomorrow night. The ear-piercing, well, it was Jake prompted that."

For the rest of the day I was on tenterhooks. I was worrying that Mr Carlisle might ring up and cancel. It was just after eight when the phone rang and Mum answered it.

"Oh hello Mr Carlisle." I heard her say.

Bother! He's thought twice about it.

"No, don't mention it .... Yes, we really are very grateful .... Yes ... Yes, he's here, one moment."

Mum called me from the hall.

"Harry, it's Mr Carlisle. He's just rung to say thanks in person for the wine. He'd like a quick word, Harry."

I took the phone as Mum went back towards the kitchen.

"Hello."

"Harry. Can you speak?"

An odd question really, then I realised. What he meant was 'Can anyone else hear you?' I pulled shut the door from the living room and spoke quietly.

"OK, go on."

"Harry. I've been thinking."

And he didn't sound as if he was going to pull out. There was a bit of an excited tremor in his voice.

"You said your friends are going to their party at the Dragon? I assume that's the Green Dragon, just off the by-pass. Well, they've got a separate lounge there. It's a bit upmarket, it's well away from the Function Room. I just wondered if - if you'd like me to take you there - as Helen that is. If that's OK. So maybe you could get here a little earlier, so that you have some time to prepare and so on, I've got something a little special for you."

I had to think quickly, obviously Mr Carlisle had been doing just that. I spoke quietly.

"But what if someone recognises me? I mean, they might, Jake or somebody, I don't know, Mr Carlisle."

"Harry. I promise you. Nobody will. I mean, your parents didn't the other day, did they? And really dressed up for the evening, there is no way will anybody recognise 'Harry'. Trust me."

I did trust him.

"OK. So, about eight then?"

"Great. And, just so there's an excuse for us talking, don't forget your Biology homework this holiday. OK?"

Mum and Dad accepted the excuse when I told them, and went on a bit about what a nice man Mr Carlisle was, calling to thank them like that. I was still nervous about him ringing to cancel, all through the next day. But I have to admit my excitement level rose, even though it was high to start with.

'Something a bit special'?

What did Mr Carlisle mean by that? It had to be something to wear, jewellery maybe, or a different top to wear with the skirt I'd worn before? It was just a few minutes after eight when I arrived at Mr Carlisle's front door. He greeted me, obviously still rather excited himself.

"OK Harry, let's get straight on with it. I've got all the clothes ready, in Marion's room of course. Come on, let me show you."

I followed him up, and I really did gasp in amazement when I saw the garment hanging there on the outside of Marion's wardrobe.

"Mr Carlisle! Is that - THAT skirt - and the top as well?"

I could see it was. The black one, from Roddhams' window. The one we'd seen a few days earlier. And the shiny silver top too.

"I said I thought it would suit you. Just the thing for an attractive young lady to wear on a special night out. Which this is, of course. I really did think it would be a good idea not to borrow any of Marion's things. I don't think she'd realise, but just to be sure."

I was speechless. Literally. I just touched the skirt, I slid my fingers over it, and over the sheer material on the sleeves of the blouse. I revelled in the texture and the shape of the bodice. I goggled at the incredible plunge neckline.

"You want me to wear - THAT!"

Of course I wanted to. It was beautiful. Shiny and silver, a clingy material which would obviously show off my 'assets'.

"Well, Harry. Let's see what it looks like shall we? But I really did think you might want to, after all this may well be your only chance."

"Mr Carlisle. Don't try to tell me you're going to claim that on expenses."

I smiled, he laughed too.

We settled down to prepare for the evening. Mr Carlisle had assembled the cosmetics on the dresser. From what I could see he had been spending, I recognised the brand names of several of the items. This wasn't cheap stuff, he'd gone for up-market cosmetics too. I shivered yet again at the thought.

And the surprises didn't end there. Mr Carlisle had a rather self-satisfied smile on his face when he opened the wardrobe and removed a large bag . The first item he pulled out to show me was a new lingerie set, not purple this time but black, and very exotic. It seemed so sheer to me, so smooth, black and ever-so-slightly lacy round the top edges, of the bra and the thong, each with a small jewelled insert, on the bra just above-left of the left cup, on the thong it was on the left too, near the top. They looked lovely. And it had a garter belt too. And stockings.

"Harry. Believe me. Every transvestite in the world, every single one of them, totally loves wearing stockings. And you're going to look great in them. Now, let's begin to sort things. I think it would be a good idea to get the make-up done first, but you may like to shower before we start. We have to get you smelling sweet."

He handed me a robe. Not a pink one, at least. My change-over was about to start but hadn't started yet. I was still male, still Harry.

"OK, Harry, you have a shower. I've left some things in there, gel, foam, whatever. It's called 'White Linen', it's a famous fragrance. Something I used to like to buy for my wife though she wasn't awfully keen on it herself I must admit. And a razor and things. You go and sort that. I'll shower in our room - I mean my room - and get changed myself. OK?"

"Sure, Mr Carlisle " I replied.

He left to do his own thing and I set to my own preparations. I had shaved already that day, twice, but after showering I did so again. I felt clean. Refreshed. And indeed sweet-smelling. Back in 'my' room I stepped into the black thong with its diamante motif, somewhat surprised but delighted that it did its job rather well, its extended job that is. Not just of covering what it might have been expected to cover if worn by a real female, but also that it just about managed to compress and hide my - extra bit!

I slipped my bra into place and noticed it didn't have any shoulder straps. I clipped it in the centre, then adjusted the cups. Of all the items I had tried, and in fact the ones which came after, this was so definitely the best. The very best. Simply, because it worked. It did its job, or rather its jobs. One, even though it was strapless it supported me in a way none of my other bras, not Mum's sports bras, not the purple one Mr Carlisle had got me, had managed to do. My MPMs nestled snugly in the bulging cups, the stiffening and the under-wiring working together to support my bulging boobs. I resolved, there and then, whatever happened that night, to get Mum to get me one just like it or at least get one myself. Maybe in white. Mum would probably not be happy with me wearing a sexy black bra but this one was SO comfortable.

And two, it looked good. Now that aspect, I wasn't at all sure I could convince my mother of. I checked its label.

'Black poly/cotton Bra, 40-DD, Padded, Strapless and Under-wired, Plunge, Diamanté motif'.

And plunge it most certainly did, the edges of the cups just manages to cover my enlarged nipples, and in the middle - wow. A cleavage, and what a cleavage. I stood admiring my figure in the mirror for a few minutes.

The suspender belt, by comparison with the rest of my lingerie, was easy to put on. But the stockings, well! They were labelled as 'Nearly Black, 10D, seamed'. They were incredibly sheer, or so it seemed to me. And they felt just plain gorgeous. As I heard Mr Carlisle coming back, I quickly put the robe back on, gathering it at the neck. I wanted to surprise him with the effect of my lingerie, but not yet.

"All right, Mr Carlisle. Barbie doll time again?"

We'd joked earlier about why Mr Carlisle had liked to dress me up. I'd made a comment, something about him having a full-size Barbie doll to play with, to make up, to in some way 'make' a woman. It seemed a rather insulting thing to say, both about him and about me in a sense, but we both knew we were playing at something. That hadn't been serious. And now, this was. I was going to be his real-life Barbie, his escort for the evening.

"I thought the better-quality make-up might be a good idea, your skin seems so much better now. No need for the medicinal stuff, is there?"

Of course, he was right. No need at all. And good though Mr Carlisle's previous efforts had been, he did an even better job on me this time. He actually showed me a full-page print-out, one which showed a woman - or rather a transvestite - he'd found on the web. The image showed very clearly the sort of make-up he had used and the effect it produced. He was using that picture as some sort of model for me, changing things a bit of course but basically going for that 'look'.

Well, it worked. After less than a quarter of an hour he'd finished doing my face. When I looked in the mirror I wasn't that impressed, the hair and the robe didn't look at all feminine. Basically I looked like a young man with make-up on. And a rather silly one at that.

"OK, let's try the wig, Harry."

That made a big difference. I looked again, at the same face, big dark eyes, smooth skin, thick lashes, cheeks lightly highlighted with blusher and all augmented by the same red wig I'd had the previous time. Well, there was a definite feminine feel to the whole 'look'. We were getting close.

"I thought a darker lip colouring this time, Harry. This dark red will match your nails. "

Mr Carlisle showed me the pack of longish, stick-on false nails.