H Is for Helen

"OK, shall I do the mouth now? Then you can show me the full effect, lingerie and all."

But I really didn't have time to comment - the phone rang. He seemed annoyed. He was obviously enjoying himself, wanting to see my reaction when he showed me things. But he was interrupted, mid-enthuse, by the phone ringing downstairs in the living room.

"OK. Back in a minute, Harry."

I didn't want to look at the other stuff Mr Carlisle had bought for me, I didn't want to spoil his fun in surprising me. But, when he came back up about three or four minutes later, the smile had gone.

"Harry. Sorry, problems. That was my Aunt Harriet on the phone. She wants me to go over and fix her electricity. Her power has gone off again. This has happened before, it's only her circuit-breakers but she can't reach them."

"Where is she?"

"Just the other side of Halesowen. It takes me about fifteen minutes to get there."

"And how long to fix it?"

"About a minute. Longer if I let her give me tea. I am SO sorry, this has ruined the evening."

"Why? I can still change, can't I? Now that you've done the make-up. It should take you about forty minutes, if you drive carefully. There'll still be lots of time when you come back. If it's all right, I mean, me stopping here - on my own."

Mr Carlisle thought for just a moment. He didn't take long.

"OK" was all he said, disappearing from sight rapidly.

I heard his car start up a minute or so later. I looked round. Mr Carlisle had gone to a lot of trouble. But, if he was an admirer of transvestites, if he liked the dressing-up and make-up stuff, then he'd probably had a lot of fun, planning things and shopping and so on. OK, so now to add to the fun, to really have a good go at this myself and - I shivered once more at the thought - to be his transvestite date for the evening.

I emptied the bag out onto the bed and began to look through its contents. One item was obvious - a shoebox. As always I looked at the label first - 'Black Patent Classic Pumps, style Stephanie, heel 6 Silver Gloss.' Then I opened it and took the shoes out.

They were beautiful! Which is a word I'd never ever used about a pair of shoes before. But this pair were, such high heels, oh-so shiny and with black ankle straps with silver-coloured buckles. I wondered how on Earth I was going to get them on. And even if I did, would I be able to walk in them? The sense of anticipation grew as I looked at the other items from the bag.

I'd had a quick look at the rest of the items Mr Carlisle had got for me, I knew the fingernails, stick-on false ones of course, would take some time. However, I was ready for the main feature, or rather features, the silver top and the tight leather micro-skirt. The first wasn't as easy as I'd thought it would be - until I worked out just how to do it. Or rather how to wear it. The fabric was silver-coloured and stretchy, a little like old-fashioned 'chain mail' but much finer. I slid my arms in and pulled the two halves of the front together, then had difficulties, my long red nails again, coping with the tiny zip up the front.

Eventually I got it zipped up, and spent some time arranging the sleeves and the bodice to properly cover my bra. When finally I was satisfied that I was wearing it correctly I turned to the skirt. The black leather was rather more flexible than I'd imagined it would be, this time it didn't take me long to pull and zip it up, just about managing to encase my bum and cover the tops of my stockings.

Then I tackled the jewellery, there were two small boxes, the sort of padded packaging used for that sort of thing. The first was - well - cheap. It even still had its price ticket with it, it was a 'Dress Ring Multi-pack'. But I wasn't disappointed, not at all. £2.99 for what was basically a pack of ten cheap, rather flash dress rings, assorted, not gold or silver of course. The silver-coloured metal ones were probably steel, the gold ones would be maybe brass. And all the 'stones' were glass, of course. But they actually looked quite good. OK, four of them looked awful, and one was badly made, the 'stone' was stuck on way off-centre.

But I chose five of them as 'acceptable', all with silver-coloured settings, and fitted them onto whichever fingers they fitted. The result was – more than acceptable. Now I didn't know exactly what sort of criteria a woman might use in choosing rings, what type, what should go where, what combinations worked and what didn't and so on. All I knew was that the result looked fine. The five rings enhanced the appearance of my hands, added to the effect of femininity created by my elongated deep-red fingernails.

But the second box - that wasn't cheap. Definitely not. You could tell - the black padded package was of a substantially superior quality. And so were the contents. None of this 'Multi-pack' stuff. The box contained a necklace, and a pair of earrings. Proper earrings, that is, not clips. And these weren't brass or steel, whether they were real silver or just silver-plated I didn't know but they looked good.

I wanted to wear them. Big, pendant, diamond-like earrings, with the little hooks pressed through my piercings they dangled about four inches below my ears, glittering and sparking as my head moved slightly from side to side. I could feel the weight, I could 'feel' the attractiveness when I saw them in the mirror. Even with my newly-acquired long fingernails I managed to fit them quite easily, but the small clip on the matching necklace, that took me several minutes to negotiate. Eventually though it just clipped into place.

The overall result, as the heavy gem-studded centre of the necklace nestled against my chest, at its lowest point just dipping into the very top of my cleavage, was very satisfying. Real diamonds even? Maybe. Logic told me Mr Carlisle hadn't just bought this for me to wear for the evening. This had to be his wife's. I felt strangely 'honoured'.

I realised that the fiddling with the jewellery had taken time. Mr Carlisle would be back soon. All I had left to do, basically, was to put my shoes on. It's strange how packets and boxes and labels intruded into my life that evening. Basically, I suppose, providing information about their contents which was not at all obvious to a member of the male half of the species. I looked at the shoe-box again.

'Heel 6 inch Silver Gloss'.

High heels. Very high heels. OK, if I was to play the part fully, the part of a sexy woman, I had to try this.

I stood the two shoes beside my feet by the bed and slid my feet into them. The fit was as near perfect as I could have hoped for. I'd mentioned to Mr Carlisle that Marion's shoes, the other pair I'd worn, were basically OK but just a little bit tight. He'd obviously taken that into account in choosing these. But where the hell had he got them? I just couldn't imagine myself, Harry that is, going into a shoe shop and buying a pair of Ladies' shoes. Not a pair like this.

Again the long finger-nails gave me a little trouble as I fiddled with the small buckles on the ankle straps. Eventually the first slipped into place, then the second was easier. Then I stood up. Strange. Very strange. Then I moved, the simple task of moving one foot in front of the other. 'Walking' it's called, but this was a different version of the 'walking' I'd been doing for the whole of my previous existence.

This was on my toes, nearly, I wobbled a little. Then I got into a 'run', in a sense, took about ten steps across the whole width of the room. This was fun! This was different. And to my surprise, it was nothing like as difficult as I'd imagined. Very quickly indeed, as I tottered back and forth across the room, basic balancing techniques came into play. This was indeed fun.

'OK, Helen' I thought. 'Time to move'.

With my bag in hand, the last of the 'special' items Mr Carlisle had bought for me - or should that be for him - I carefully negotiated the stairs and went into the kitchen. A quick glance at the clock told me he was maybe due back in about five minutes. I wanted to make an impression.

Earlier, as he was doing my make-up, he'd shown me some pictures he'd down-loaded of 'Lucy', the transvestite he'd used to model my make-up. In different outfits, of course, and in a variety of poses. But one I'd specially liked showed her sitting on a high stool in a bar, legs crossed, chatting to a man who was clearly very interested in her. In fact he'd had a hand on her exposed thigh. Maybe a little later in the evening .... - hell, what was I thinking?

But for now, I could do that in the kitchen. I filled a glass - a wine glass, that is - with orange squash and sat in one of the two high stools at the breakfast bar. And I heard a car outside, braking rather hard. I crossed my legs. I sipped my drink. I waited. The door opened. I looked up and smiled.

"So, Mr Carlisle, how does your Barbie look tonight?"

Mr Carlisle didn't freeze, he didn't stare, he wasn't rendered speechless. He just grinned, extremely widely. Then he recovered.

"Barbie never looked like that! Christ, Helen. You look - stunning!!"

Which was, of course, exactly what I wanted him to say. I sipped my drink.

"So, Mr Carlisle , are you ready? For your big transvestite adventure?"

"I fucking am!"

Mr Carlisle dashed upstairs himself. to finish dressing. It only took him a few minutes, then my 'date' reappeared fully regaled in dress suit and bow-tie.

"Mmmm. Handsome" I said, and I meant it.

Insofar as I was any sort of judge of masculine desirability, he fitted the bill. Nice suit, neat shirt, well-groomed. Yes, attractive. Handsome even.

As Mr Carlisle drove us through the town centre and out towards the by-pass, I asked him about his Aunt Harriet, what he'd done, what she'd said. I really wanted to keep the topic of conversation neutral. I had to try to stay calm. This really was about to be a big adventure. Going into town a few days earlier in a skirt had been one thing, but this - going into a pub so provocatively dressed, this was in another league. And the same pub as all my mates at their end-of-term party, well, the word 'insane' came to mind. But the danger, the risk, the however-remote possibility of being found out, these all seemed to add to the experience.

Mr Carlisle pulled up in the car park and got out, coming round to offer a hand to assist me in getting out of the car. We walked together towards the front door of the pub. I was glad to get inside the lobby, it was actually quite cold and I was revealing quite a large amount of bare flesh. Just inside the door Mr Carlisle pulled me to one side. He spoke quietly.

"Harry. Listen, this seemed like a good idea the other day. But - really - we can turn round and go home right now if you like."

I was tempted. This was beyond what we'd done on Monday. So far beyond. Maybe it was going too far? Perhaps we should just drive back and sit in Mr Carlisle's living room, maybe have a drink or two, flash my thighs at him, that sort of thing? The sensible course of action would be to do just that.

I might have suggesting doing just that if, the very next moment, the main door hadn't opened behind us. And if Darren Harris, class dork, hadn't walked into the pub. Obviously nobody had told him the pub's function room was at the other side of the building, and that you had to use the other door. Or, more likely, someone had told him and the full meaning of the words 'other door' hadn't sunk in.

But it wasn't just the fact that he'd come into that door that decided me, it was what he said a few seconds later. He actually looked me straight in the face as he came in. And then his eyes moved downwards. Somebody, one of the others in his little party pulled him back, realising their mistake, knowing they'd have to seek out the other entrance.

And as the door swung shut I heard his voice say "Christ Jake. Did you see those tits? Christ they're gigantic! Wish I could ..." and I didn't hear the rest.

But that was enough. I wanted to do this and I knew Mr Carlisle did too. I moved closer to him.

"Mr Carlisle. We're going to do this. But remember, none of this 'Harry' crap. I'm Helen. And, while we are at it, I suppose I should call you David for tonight. Now, come on, just what you've always wanted, going on a date with a sexy transvestite. Like you said, your only chance really - so come on, let's do this!"

I took his hand and, with our fingers interlocked and with me holding on very tightly indeed, we went through into the bar. Now it would not be true to say that as we entered absolutely everyone turned to look at us and to stare at my boobs and my figure and so on. But, there was a bit of a hush as we strolled across towards the bar, and several men moved out of the way to allow me through. And Mr Carlisle too of course since I was still gripping his hand tightly.

"Half of bitter" he called out as the barman came straight over towards us.

He looked at me. All right, we should have sorted this out in advance.

"And I think I'll have a vodka-and-tonic this time, darling" I added in response to his questioning look.

Trying to give the impression we did know each other and that, in some way, I didn't always have the same drink and he'd had to ask me for that reason. And also trying to keep my voice quiet and in some way 'gentle'.

He paid for the drinks of course, and I settled down on one of the tall stools at the end of the bar, replaying the scene from the kitchen and from the pictures he'd shown me. He leaned over, the noise level in the bar was beginning to rise again.

"Helen, you do realise most of the men in here are staring at you."

I smiled.

"Actually Mr Carlisle - er - David, I'm rather surprised at how nice a thought that is. And does it make you feel good?"

"Incredible" was his reply.

He just grinned. Stupidly, really, and I told him so.

"David, my darling, stop it. People are going to wonder just what's wrong with you."

"I don't care, Helen. I dare say other guys have had as much fun before walking into a bar with a transvestite, but I guarantee nobody has ever had more fun. And nobody has ever had the pleasure of being with such a fuckable babe!"

"David!"

And we just chatted, quietly between ourselves, for maybe half-an-an hour or more, commenting on what we thought about what we'd done and what we were doing, both of us being really rather smug about our 'adventure'. Eventually I decided it would be rather nice to move on just a little, so after David had got us a second round of drinks I took hold of his hand, and began to stroke it gently.

"Helen, please, you really should stop that. Not that I don't like it, or course, but - oh hell, what's the use..."

He took hold of my hand and kissed it!

"David. You really do have to do better than that!"

And I leaned over towards him and kissed him! Not passionately, just a sort of affectionate kiss, just for a second or so - but on the lips!

"Is that OK, David?"

He looked round, clearly somewhat embarrassed.

"Helen - wow - you do know what you're doing, don't you?"

"I hope I'm exciting you, my darling."

"You certainly are!"

And before he could say or do anything else I grabbed his hand again and kissed it myself, and then laid it on my exposed thigh.

"Excited now?" I asked.

Mr Carlisle swallowed a little, not totally sure what was going on and to be honest neither was I. There was a definite excitement here, being dressed so sexily in the bar and flirting with Mr Carlisle. But he realised and I did too that time was getting on.

"David, I think we'd better make a move. It's getting late, I think some of the gang from school may well be coming through to the bar soon, I really don't want to be seen like this - with you, you know."

"Helen, believe me, absolutely nobody will realise."

"Maybe so but ...."

We left it at that and started to get up to leave. I held on to Mr Carlisle's hand tightly again as we moved towards the exit. As we left the actual bar and were just going to go through the main door, a couple of girls came through from the other direction and turned right. I knew exactly where they were going, and a rather naughty thought came into my own mind.

"David, hang on, back in a minute."

I released his hand and turned that way myself, following Anna whatever-her-name-was and the gorgeous Holly Tomkinson into the Ladies' Loo! Of course I didn't really NEED to go into there, I'd only had a couple of drinks and anyway we were due to be heading back 'home' very soon after. But it was just the thought - me, Harry, in the Ladies'. Wow!

I went in and was immediately slightly flustered. There was nobody there. Then I realised, of course, this was different. There were four cubicles in front of me, three had closed doors. I went in the other. Now I could have experimented, tried to pull down my panties and pee and so on but I thought it was better not to try. So I just sat there for a minute or so, I heard shufflings next door. I was inches away from Holly Tomkinson with her knickers down! The thought send a shiver through me but I resisted any temptation to look over or under the panelling in there, I just stayed seated.

Then I heard doors opening and water flushing so I pushed the press-button in my own cubicle and opened the door. I could see two girls with their backs to me, leaning towards the large mirrors in there. And the nearest bum to me was Holly Tomkinson's. I walked over to stand next to her, opening my handbag as I went and taking out my lip-gloss. I leaned towards the mirror myself and touched up my own make-up, totally un-necessarily but what the hell. I could see Holly clearly, she hadn't recognised me at all. Well, in that situation, she wouldn't have expected to see me - Harry, that is - at all.

And I enjoyed the sight, staring in front of me, the sheer delight of being able to look straight down the cavern between Holly's tits. I made eye-contact with her briefly and smiled a little. Then I realised. She was staring at my cleavage too. I glimpsed across from one to the other, there was no comparison. Holly has the reputation in class of being a very well-developed girl in that department but, looking at the two pairs of tits I could see, she was nowhere. The combination of my swollen MPMs and the tight under-wired bra gave me a substantial advantage in the breast area.

And I could see, and I'm sure Holly could too, that as I leaned over the weight of my 'tits' was pulling my bra forward and pulling my tits out! I could just see the deep pink circles of my aureoles jutting out above the top of my dress. It wasn't just the thrill of seeing them, it was the fact that Holly was seeing them too! I couldn't resist a slight wriggle, seeing my boobs wobble and seeing Holly gasp in amazement.

I walked out in front of her and the other girl who I didn't really know, hoping Holly was similarly staring at my too-short skirt and extra-revealing thighs. As I left the Ladies I saw David. He was waiting - and he was talking to Jake!

Shit! Now what? Then I realised that Jake wasn't alone. He was with Darren, the lad who'd glimpsed me before when he'd come in the wrong door. Actually it was Darren that Mr Carlisle was talking to, though Jake was stood right next to him. I hoped Mr Carlisle was right about my being so well-disguised. I had no choice, I walked up to him and slid my fingers into his.

"Hadn't we better be going, darling?" I asked, trying to keep calm and to keep the tone of my voice 'light'.

Both Jake and Darren had turned towards me. And, I'm glad to say, neither of them was really looking at my face. Obviously. That gave me a chance to turn a little and give them a full frontal view, or as near as they were going to get. Mr Carlisle had taken my hint, he began to lead me towards the outside door. I could feel the eyes of the two boys staring at us as we left, and in the reflection from the tall glass panels by the entrance I could see that, even as we walked away, one of them had pushed the door open with his foot. They were both still staring, Mr Carlisle had noticed too.