H Is for Helen

Doubts appeared in my mind as soon as I looked closely at the skirt. Maybe there was another one? But I had a good look at the one in my hand first. The colour was OK, it was a sort of dark blue, slightly denim-like. And the fabric was basically neutral too, probably just polyester or polyester-cotton. But it looked as if it might be too small for me. I took off my own trousers and stepped into the skirt. It was not that easy to pull up over my bum, it really was rather tight. But I did get it on, and fastened at the waist. I looked at the blouse-skirt combination in the mirror. It was rather short but OK, at least it didn't fit into the 'extremely short' category, I couldn't see the tops of my tights below the hem which was about seven or eight inches above my knee.

And with the jacket? I slipped that on and grabbed one of the two shoulder-bags hanging on the rail inside the door. I looked again.

Perfect. Female. Definitely. I shuddered. This had begun as a practical exercise, it was turning into something more, very much more. I was going out as a woman, OK, but no longer did I just want to 'pass' as female. I imagined myself on the High Street. I didn't just want to look female, I wanted to look good. So there were a couple of other things to consider.

I was hurrying now but still managed to varnish my finger-nails quite quickly and effectively, having seen some of the small bottles in Marion's drawer. And jewellery. I knew I'd feel better, maybe even look better, wearing jewellery. I was prepared to be disappointed when I started hunting through the largish collection of earrings, they were all for pierced ears. Then I found one gold hoop with a clip on, I desperately searched for the other one, hoping I wouldn't find it damaged as I had the suit trousers. I found it.

The necklet and rings were easier, not so much problem there, I just slid three gold rings onto whichever fingers they fitted, and slipped one thick-ish gold-effect chain round my neck. It hung there, its small pendant dipping into my blouse. I undid the top two buttons to show it off, enjoying the fact that it revealed – cleavage! I stood up. Ready!

When I walked into the dining room Mr Carlisle wasn't there. I heard a car engine noise from outside, realised he was backing out. I was glad. Though very confident by now, almost proud of my appearance, I didn't fancy public transport. I picked up my project folder and put a couple of pens into my bag. Then I had to go back upstairs to get a few personal items from my jacket pocket.

Mr Carlisle came back in and saw me.

"Well Mr Carlisle. Will I do?"

I had expected him to come very close to me, to inspect for flaws, to see if he thought I could pass OK as female. But he just stood there.

"Harry, you look - wonderful."

I glowed. I was so pleased. I had wondered if he'd make a fuss about what I'd chosen to wear. I thought he might go on about my wanting to wear a skirt, maybe compromising my position and him as well if it didn't suit, if he thought I wouldn't pass. But he didn't. He just stood there. He didn't say anything, he was just staring. I walked over towards him, probably for the first time really aware of the effect of my 'boobs' on my general posture and appearance. The bra was doing a great job of showing them off, even through my blouse. And it was doing a pretty good job of controlling them too, as I walked towards him in the short-ish skirt they seemed to begin to wobble up and down. I got the impression that, walking like that, in short jerky steps, they would have oscillated madly without the bra doing its job.

I was going to say something else when Mr Carlisle interrupted my train of thought.

"Harry. Really. You look incredible. I just thought you'd do the jeans and top, and maybe a little make-up. But this - well, you look gorgeous."

"Mr Carlisle, really?"

"Really Harry. There is absolutely no way anyone would know. You look totally female. Maybe this is going to be easier than I thought. I was trying to come up with ways of doing the photos and the inspection from the car. Perhaps driving slowly up the High Street."

"Er - you can't. I mean, it's pedestrians only, isn't it?"

"That's why I was having difficulty coming up with some sort of plan. But now, really, there is no need. Nobody will 'read' you."

" What do you mean 'read' me?" I asked.

"Oh sorry. I didn't really mean to say that. What I mean is, nobody will spot you as male. nobody at all."

He thought for a moment.

"Unless of course I call you 'Harry'."

"Sorry?"

"If I call you Harry and somebody overhears, they're going to be very confused. That could be an issue. So, Harry, just in case, you need a female mane. We've not had to think about it before, just the two of us at home if you like, but if you are going out you're going to need a girl's name, aren't you? Any ideas - what would you like to be called?"

So then I had to think. I'd been happy, for many years, with 'Harry'. There weren't so many Harry's around. I was pleased Mum and Dad had chosen that name, not something ordinary like John or Peter. Or even Clyde, apparently that had been in the offing just before I was born. But - a girl's name? I thought about 'Harry'. Something a bit similar, maybe, but not too similar?

"All right. There was a girl, when I was in junior school. I used to like a lot, she was called 'Helen'. Her family moved away, pity really. But the name's stuck in my mind."

"OK then. Right, Helen. I quite like that. Ready for off?"

I picked up my folder and 'my' handbag.

"Ready as I'll ever be."

I was a little nervous even going out of the front door of Mr Carlisle's house and towards his car. As I approached it, he walked past me - and opened the passenger door for me.

"Let's do this right from the word go, Helen. Careful getting in, you're female now. Sit first, then swing your legs in.... That's right, well done."

Just sitting in the car as we drove wasn't too bad, I was somewhat hidden from everyone we passed. But when Mr Carlisle parked at the back of the Council Offices and we had to walk down the narrow street and onto the High Street, my nerves got the better of me.

"Mr Carlisle. I can't do this. Really. I mean, I want to but I can't."

"Helen. Look at me" he said, standing just in front of me. "There is no problem, believe me. Nobody will stare. Or at least, if they do, the men are eye-ing you up, and the woman are just jealous. You look gorgeous. And you've come too far now. Not in distance terms, we've only come a few miles. But in dressing and making yourself up, you've made yourself into a woman. So enjoy the feeling. But remember, we're here to work. You've got things to do. So - OK?"

He took my hand and squeezed it. I realised that people were watching. They had seen what they would see as a symbol of affection.

But nobody came over and started going on at me. for going out in public dressed like that. And - one person, a man, probably in his mid-twenties, walked past the two of us. I saw his eyes move from my legs to my cleavage, then to my eyes. And he smiled! I shivered, but I did realise, I could do this.

Though we'd had some doubts about actually how to do this, my project stuff that is, we had discussed in some detail just what needed to be done. So I did it. I actually walked up and down the High Street, slowly at first. Stopping every few yards to make a note about the buildings on the other side of the street, the style of architecture, the approximate age, the current use.

My project was to be about the 'Built Environment' - an aspect of Human Geography, what buildings are used for, how big they are, not just shops of course, offices and flats and houses and so on. Sure I could get some of the data from the Internet, I would have to, but these observations together with the photographs I took as I walked back down the street, they would form the bulk of my study. And as I walked along Mr Carlisle stayed a few yards behind me, basically just window-shopping. We'd reckoned it ought to take just over an hour, in fact I'd got what I needed in about fifty minutes.

"OK Mr Carlisle. I think I've done."

I'd approached him looking in a dress shop, of all places, there happened to be one close by as I completed my task.

"Right, well done Helen. So - what do you think of that? The black one, there."

I looked in the Roddhams' window. The theme for the window-dressing seemed to be something like 'Party-wear' or 'Formal evenings' or something like that. And in the middle of the display was a mannequin - surely that should be womannequin - wearing a tight glitzy silver-coloured top - and an indecently tight, short, black leather skirt.

"How would you like to wear that?" he asked.

I looked again. Basically it was a very attractive ensemble. It seemed a strange word for me to use but that's what I thought. And I said so.

"It's lovely."

"And, though I hesitate to say so, Helen, you would look stunning in it!"

I didn't know how to react to that comment. I just looked at it. It really was a very strange thought, to try to imagine me wearing something like that. So I imagined Holly Tomkinson wearing it. Wow!

"Do you think we'd better be heading home now, Helen?" asked Mr Carlisle.

I agreed, we turned and began to walk back in the direction of the car park.

"Shit!" I muttered.

Though quietly, but Mr Carlisle heard it.

"Helen?!" he hissed, not wishing to draw attention.

"Mr Carlisle. Twenty yards ahead, at twelve o'clock. My Mum and Dad!!"

He was flustered. Probably thinking the worst, straight away. Himself, trusted tutor, found in town with student dressed in women's clothes. One helluva scandal. But I reacted more quickly, probably a case of needs must. I just had to get by them in some way. They'd just stopped to do some window-shopping of their own so I grabbed Mr Carlisle by the arm and steered him across the road. I let go as soon as I could, and veered into WHS and out of sight of my parents. I hoped.

We spent a minute or two looking at the magazine rack in there. Mr Carlisle was inspecting one about cars, I surprised myself by skimming through 'Marie Claire', actually enjoying looking at an article by a celebrity about very high heels and how she didn't like to wear them but felt she had to. I asked Mr Carlisle to have a look outside, he came back to report that he couldn't see my parents any more. I breathed an almost-audible sigh of relief when we got back to the car.

As we went into his house, Mr Carlisle did exactly the same.

"OK" I said. "That's over. I need a drink."

With a combination of relief and, in a way, regret. It was almost the end of term, after a couple more sessions I wouldn't be seeing Mr Carlisle for a couple of weeks. No chance to dress myself up - had I really just thought that? And why did I feel disappointed about it?

I remembered.

"I'm sorry, sir, I forgot. My Dad wanted to thank you for all the help you've given me. He gave me something for you." I tripped up the stairs and came back down with the bottle of wine. "You know, we really are all very grateful. Mum and Dad and me, we all are. Even though they don't know about this stuff today. I'd have had all sorts of problems if you hadn't been there to help. Thank you."

I handed over the bottle. And, while Mr Carlisle had both of his hands full, I leaned over - and kissed him on the cheek.

"I hope that's OK, sir."

Yet again Mr Carlisle looked concerned. He did smile a little and turned towards the kitchen.

"Thanks very much - er - Helen. Now excuse me, please, now I really need a drink after that."

He emerged with a corkscrew, and two glasses.

"Join me? After the shock of seeing your parents, you could probably do with one too."

We sat in the lounge this time, not in the study-cum-dining-room where we'd always done our schoolwork. I sipped the drink quietly, wondering if Mr Carlisle was going to suggest we got on with the project there and then. Or should I change out of my feminine clothes first? And what about the project? If I had another drink or two I probably wouldn't be able to concentrate. After a few minutes Mr Carlisle offered me another glass of wine. I took it and sipped it, a little more slowly this time.

"Mr Carlisle. What did you mean when you showed me that outfit in that window? Did you really mean you think it would suit me?"

"I meant it, Helen. You'd look knockout."

"Thank you, Mr Carlisle. That's a very flattering thing to say. "

"That's OK. Helen."

He was staring at me. I was staring intently at him. I had something to say.

"Mr Carlisle. I've been coming here for over three months now. OK so you know about my problems. The reason I have to have special tuition, I mean. But I'm a bit puzzled. You obviously are concerned, I suppose that's why you've been so supportive, with me needing to be comfortable and so on. And with dressing up so we could do the project data stuff today. But you've never actually asked to see - my 'problem'. I'd have thought you would have, at some time in all this time, that is."

Now what I did next wasn't really a follow-on from that. Honest, it wasn't. It's just that I was getting a bit warm, what with all the excitement and the glasses of wine. I just stood up and took my jacket off. Just stretched a little, then I realised that in doing so I was giving Mr Carlisle a clear view of the front of my blouse, and the purple bra showing through it. And of the effect caused by my 'breasts'. However, I continued.

"I saw my doctor again on Friday. Apparently they are going to start going down. The hormone tests showed that, the skin condition has cleared up, but that was always going to decrease first. Now these - they've stabilised, the doctor said."

Mr Carlisle stared even harder. I felt he wanted to say something but for some reason didn't dare. I walked over towards him, actually enjoying the sensations I was experiencing as the tops of my tights rubbed lightly against the inside of the hem of my mini-skirt. I deliberately, carefully, took his hand.

"Would you like to see them?"

He gulped. My tutor gulped, visibly. I'd hoped I might relax him by holding his hand but it only seemed to make him more agitated.

"Would you like to?"

"Oh yes. Yes please. Helen." He was breathing heavily.

"You can call me Harry now, you know."

"I think I'd prefer 'Helen'. After all, you are - you do look like - an attractive woman."

"OK Mr Carlisle. Enough of the flattery. Come here."

I led him across towards the door, it seemed a good idea to go through and sit on the sofa. There we could be side-by-side comfortably. I began to undo the buttons on the front of my blouse. Mr Carlisle was still staring.

"Oh Helen. They look gorgeous" he said as I pulled the front of my blouse apart to reveal my bra-covered 'bosom' in all its glory. "May I - er - feel them?"

"If you'd like to, yes, of course."

I watched as his hand moved closer and cupped the underside of my right breast. I felt good as his hand began to stroke under the swelling mound.

"Do they, I mean, do they - hurt, or ache? What does it really feel like?"

"Oh, no. They don't hurt at all. It was odd at first, with the weight and so on, but specially with this kind of bra, well, they're well supported. They don't ache at all. In fact they feel rather nice. In a strange way I'll be sorry to lose them. They're a DD cup now."

"Oh my!" muttered Mr Carlisle as his hand began to move further round the breast, and to begin to stroke and feel my left boob.

It felt good. I said so.

"Here, let me show you."

I un-fastened the small clip between the cups of the bra, releasing my boobs. They sprung outwards a little, free from the tension of the bra. Then, suddenly, they sprung outwards a lot.

"Oh my GOD!" exclaimed Mr Carlisle. "They are just so beautiful, Helen."

I didn't reply. I couldn't. I was tingling. It wasn't just the breasts which were excited, a shiver was going through my entire body. This was something new. Someone was actually - fondling - that's the only word for it - my breasts. And rubbing his fingers over my nipples. And my nipples were going wild. I'd felt something like this the previous week while the doctor was measuring things, but this was better. Bigger and better. I was shaking with excitement.

"Oh wow. Sir. That really does feel good."

I looked down, I didn't really need to but I could feel something extraordinary was going on. Blood was coursing through to my nipples. They were swollen and seemed to be turning a much deeper red colour, they were suddenly so sensitive. I could feel so much pleasure as Mr Carlisle stroked them gently.

"I don't understand. Why is this happening?"

I think I was almost crying, the waves of pleasure were so exquisite. I looked up. Mr Carlisle was sitting there, stroking gently. A tear began to roll down his face. I couldn't help myself. I'd kissed him on the cheek earlier, this time - I just had to - I kissed him. Once, very lightly - on the lips.

He jolted backwards. As we parted, his hand stopped moving. We sat very still for a minute. I fastened my bra and buttoned up my blouse.

"Helen. Harry, that is. I know it's nearly the end of term. Look, this shouldn't be happening like this. It isn't right. I'm sorry. I'm going to ring your school tomorrow and suggest they arrange for a different tutor next term. I think it would be for the best. "

Which is exactly what I didn't want to hear.

"Why?"

"Because this isn't right, Harry. Though it's OK to get involved with a student's problems, a tutor should be interested of course in order to provide support. And I am. But I'm rather worried - what this could lead to. I think you'd better go and change now. I just hope we can continue until Thursday, we really should get this project sorted before the end of term."

I was really disappointed. I mean, the day had all gone brilliantly, certainly as far as I was concerned. I got up to go up and change.

"Mr Carlisle. I do understand some of what you've said, but, hell, things seem to be going so well. And if it is the dressing-up which is worrying you, maybe I can see why. But I don't have to. If my condition is going to improve soon there won't be a need to, will there?"

"Harry. Please. Sit down for a moment. There's something you should know."

I sat. Mr Carlisle cleared his throat. He was obviously going to say something very important to him but had some difficulty in starting out. I was unsettled too, obviously.

"OK then. But please, before you start, do you think I could have another glass of wine?"

He got up and poured me another glass. I sat and crossed my legs again, and sipped it slowly. I knew I had to listen.

"The trouble is - Helen - you look so fucking sexy, if you'll excuse my language. I'm sorry but I don't know another way to put it, to express what I think. I just don't know if I can trust myself. Hell, I'm not saying this right. Helen, do you know what a transvestite is?"

"Yes I do. And I do realise, though I hadn't thought about it, right now I'm really a transvestite. Dressed like this, I mean."

"Well, for several years now, since not long after my wife died, I've had a 'thing', some sort of obsession, with transvestites. Not in a big way, you understand, I'm just fascinated. I like to look on the Internet, look at their web-sites, pictures of men dressed up and so on. Some of them look very convincing, very sexy indeed. "

I sipped my wine. OK, young and somewhat naïve I may have been but I was beginning to understand Mr Carlisle's situation. And why he had helped me initially, with the ladies' lingerie and so on.

"I have admit, I've been 'playing with you' to an extent over the past few months. Helping with make-up and clothes and so on. And when I saw you this morning, in a skirt for the first time, well, you probably wouldn't understand."