P Is for Penni

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A series of stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me!
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"So Paul. Are you a transvestite?"

Not the sort of question you expect in that sort of situation. Not in the bar after the match, even at the end of the evening when Martin and I had each had about six pints each. But - to be honest, I'd been expecting the question. Just the way the conversation had been going earlier, and the sort of things Martin had said. And the way he looked at me.

"Er - yes."

There. Said it. I'd actually admitted it, for the first time ever to anyone. I'd never even told my wife, or any of the kids, or anyone in my family. But I'd told Martin.

We'd both stopped on in the bar for maybe ten or fifteen minutes after all the others had left. I think Martin and I both knew that our first-team careers were over. We'd had a run of three or four good games after getting drafted into the firsts. That was when the open-side prop, Jeff Holliday, had gone AWOL for a month to go to his brother's wedding in New South Wales, and have a holiday as well. And at the same time the blind-side prop got himself trampled on and laid up again for about a month.

Martin was the natural choice at open-side, of course. He'd always done well in the second team and in fact had been promoted for a few games in the past year. Quite why the committee decided to pull me out of the thirds instead of Lenny, the seconds blind-side, I didn't know. Except that there was bad blood between the chairman of the selection committee and Lenny, on account of something involving Lenny and the chairman's daughter. But I kept out of that, I just relished the chance of playing in the first team.

And Martin and I, even though we'd hardly played together before, hit it off straight away, both as mates and on the field. In our first three games together we really stormed it. We won the first and the third game. OK so we lost the second, but that was against the league leaders. And even in that game Martin scored, after I'd put him through. But in the fourth game, just before Jeff and Lenny were maybe due to return - we were awful. The other team had us sussed.

They realised we're neither of us really big enough for the job at that level, and played on it. OK so we're both tall-ish, and a bit muscular. We have similar physiques, but we're not really not big enough. Like I said, we were awful. So it was in the bar that evening, when Martin and I both had realised we were going to be back in the seconds or thirds next week, that we were enjoying our last drinking session with the 'big boys' of the first team.

And somehow, I don't remember how, the conversation got onto women, naturally, but then onto drag-queens and cross-dressers and so on. There was of course a natural disdain expressed, but one of the reserves happened to mention that he'd once met a cross-dresser and that he - or maybe she - looked attractive. Martin joined it with some sort of positive comment, and one of the second row said something and so did I.

Anyway, at the end of all this Martin and I found ourselves on our own for a few minutes, which is when he asked me. THE question. And to me amazement I'd not laughed it off, I'd said 'yes'.

"It's just the way you looked when Keith said something about him finding a cross-dresser attractive. Me too."

Now - what did that mean? That Martin liked CDs too? I must have looked puzzled.

"I like to dress up too. Not all the time of course, but - it's the vicarious thrill, isn't it?"

I realised Martin was opening up to me, and also that like me he was feeling relieved to be able to tell someone about it. I just had to say something too.

"Yes it is. Wearing stockings or tights, that sort of thing."

"Oooooh yes" was Martin's reply.

And that was that. We got interrupted by one of the other players at that moment and, despite having got through maybe seven or eight pints at that stage, we both realised we'd better change the topic.

Anyway, over the next couple of weeks, when I managed to stay in the second team which meant Martin and I were still playing together, we sneaked a couple of other conversations about our newly-discovered mutual interest. Nothing much, just some sort of acknowledgement of the 'bond' between us. Not that we mentioned anything, of course, to anybody else about it.

And then something came up with out of the blue.

"Martin? You mentioned that next weekend your wife is at her sister's?"

"Er – yes."

He said that he remembered me saying something but wasn't too sure exactly what I'd said.

"Well, I'm at a training session Tuesday to Friday. It was going to go on until Saturday but it's been changed. So Chrissie thinks I'm away until Saturday."

He didn't get it. He didn't realise what I was on about.

"So how about I come round to your place Friday evening? We could dress together."

Now that surprised him. And me too, I was suddenly amazed at myself for suggesting it. But I did. We'd mentioned some aspects of our dressing, obviously, in the preceding weeks. And we'd each admitted that we'd done it all solo so for. Pretty similar, really. Dressing at home, in our own secret clothes or our wives', both of us. And the fact that we'd both considered in some way dressing with another 'T-girl', but that in neither case had either of us done anything about it.

"So, Martin. How about it?"

He thought.

"I need to think."

"OK then, but I still think it's a good idea. I mean, I'd like to see how you look dressed, and I'd really appreciate your comments on me as well."

He'd thought. Steph was going to be away almost all weekend, from Friday morning. I think, like me, he realised that we may never get a chance like this again.

"OK," he said, nervously.

I rang Martin at work a couple of times in the following week and we sorted out the details or our little deception. And before setting off back from my training course on the Friday, I inspected the 'femme' clothes I'd got down from the loft before leaving. I'd sneaked out them when I'd left home, packed into a small case ready for Friday evening. I'd even made a couple of small purchases that Friday lunchtime to try to enhance my appearance when dressing at Martin's house.

When I got there at about six, rather nervous about the whole thing, I realised Stephanie hadn't left yet. Martin was home, both cars were in the driveway. I parked up the road and waited. After about ten minutes, I was planning to drive home myself, maybe to ring Martin later and abandon the whole thing if Steph had changed her plans. But she came out, followed by Martin carrying two cases. He loaded then into the boot, kissed her goodbye, and waved as she left. Then he turned and opened his garage door. We'd agreed that I'd drive my car into it so it was hidden from view. Just in case, VERY unlikely, Chrissie drove down that road and saw my car parked there when I was supposed to be still in London.

I waited, as instructed by Martin, about ten minutes. So that if Steph had forgotten anything, something for her sister or the baby or whatever, and came back there wouldn't be a problem. After that time, he said, she'd be on the motorway, and if there was some sort of problem then she'd ring. She didn't return. I started my car and drove the fifty yards, then swung into Martin's drive and into the garage.

I got out and grabbed my small bag. When I rang the doorbell Martin opened the front door to me almost immediately.

"Hi Paul. You sure about this?"

"I think so. Are you?"

"Yes. Let's go for it."

We sat and chatted for just a couple of minutes, both of us I think trying to put off the 'evil hour' or something. Then I stood up.

"OK Martin. How are we going to work this?" I asked, picking up my small case.

Martin had realised what was in it, and I knew the sort of things he would have been getting ready himself in those intervening ten minutes.

"Well, Paul. I'm not sure how these things work. But I thought we should maybe dress separately. You in the spare room, me in the main bedroom. That's where my clothes are now."

So we did just that. We each had a very brief look at the others' clothes while we began to sort things, in a sense to reassure ourselves that this thing was indeed going to go ahead. Then I was alone. In Martin's spare room, with my case of girly stuff. He was going to use the en-suite bathroom, I was to use the main one in the hall.

So I went through the routine. Except this wasn't routine, this was doing the same thing as I had many times before but in a different situation and for a slightly different reason. I showered. I shaved. Twice. I shook scented talc over by body. Then I tackled my lingerie.

Though I'd always regretted - in a sense - not having enough opportunities to dress, being in the closet and all, there was indeed an element of routine to my dressing. Black thong and basque, tied almost as tight as I could, side-padding in my bra to give me some sort of a cleavage. Though I don't have a very hairy chest I have always removed just the few hairs at the top to give my 'boobs' a smooth divide. Then stockings of course, black of course, for the visit to Martin I'd bought a decent pair. Black and sheer, with seams at the back. I sat down at the small dresser in Martin's spare room to go at my make-up.

It had taken some years of experience to get the right type and thickness of moisturiser and foundation to look good but not over-done. And I've always totally relished the practice of making up my eyes. It's at that stage that I really begin to feel, in some way or other 'female'.

The eye-making-up went well, that's always one of my main criteria of how good I'm going to feel, and look. I was especially pleased by my mascara, I always feel it's going to be difficult to do the lower lashes well but on that occasion I'd bought a tube of 'X-X' thick mascara which did a particularly good job. And I didn't overdo the eyebrow pencil either, which I know I'm prone to do. Just a little blusher to accent my cheekbones, then my own very favourite deep red lipstick and I was done!

I never really try to see the 'look' at that stage, the short slightly-balding hair would disappoint me, I know. But after donning my most extrovert wig, redhead and definitely 'big hair', together with clip-on long gold earrings I did begin to study my appearance. OK so I know I could never be TOTALLY convincing, never pass in public in daylight and all that sort of thing. But I really did think I was coming as close to looking like a woman as I'd ever be able to.

I always leave my nails until last for practical reasons. OK so I can lift a glass while wearing very long fingernails but the intricacies of dressing while wearing them always have been beyond me. So I slipped on my blouse, a rich pale pink number, very feminine, you might almost say effeminate. But I like it, the ruffles down the front give a suitably tarty impression in revealing something of my 'cleavage'. Then I slid into my skirt and fastened it. Martin and I had discussed the sort of woman we each liked to 'be'. Though my own favourite mode of attire has always been the classy cocktail dress style he preferred the more classic business-woman look, power-dressing, that sort of thing. So we'd compromised, deciding to go for our second-favourite style - tart.

I'd taken along my shortest, slinkiest, tightest and sexiest skirt, a little black number, smooth and shiny, leather-look and in my own opinion just plain gorgeous. There are probably quite a few women in the world who don't look good in a skirt like that, but an awful lot of them do! Rather arrogantly, I like to think I'm one of the latter. With the skirt in place I was nearing the end of my own preparation. I wondered just how Martin was getting along in the next room. However, I wasn't quite finished.

Since I was to be a tart the choice of shoes was obvious. The pair of classic black patent stilettos with six-inch killer heels remains even today one of my favourite purchases. Especially since I'd found them in a sale in a factory shop. With shoes in place, buckles fastened, I walked round a little to practice though it has to be said that I've never really had a problem there. I LIKE wearing very high heels, unlike Chrissie, and I do realise they can make or break a tranny's appearance.

I was just finishing sticking on my longish deep red fingernails when I heard a slight noise in the hall.

"Penni? Are you ready yet?"

We'd discussed names, or course. I was to be 'Penni' and my companion was to be 'Marti' - with an 'i' as well, Martin had said. OK by me.

"Nearly ready, Marti, just a few minutes" I replied.

"OK then, Penni. I'm just going downstairs."

I heard footfalls on the stairs but I didn't hurry. I knew the adhesive I was using on my nails worked well if I was careful, so I was. Very careful. OK so it slowed me down, but results here were more important than speed. And finally - this much I can manage in long nails, I slipped on my heavy-ish gold chain, nestling the round pendant just above my boobs. And slid on four or five rings onto assorted fingers. Missing out, of course, the third finger of my left hand.

I stood and looked in the mirror. I picked up my black purse, a shiny soft leather one which nearly matched my skirt, and looked again. OK, not perfect but then I was never ever going to look 'perfect'. But definitely good, maybe even 'very good'. I was ready.

As I've said I'd never done this before, dressed up with another TV that is. My tranny existence had always been totally solo at home with the exception of a few late-night drives and short walks when there was going to be no-one else around. I'd never subjected myself to the scrutiny of another person except someone several yards away, and in the dark. But I was ready to do just that.

I opened the door and made my way carefully down the stairs. Martin had closed the downstairs curtains as we'd ascended earlier since we realised that it would be after dark when we came down again and we'd need the lights on. I could see no-one was in the kitchen from the bottom of the stairs. So I turned and pushed open the door into the lounge.

We stood for a moment facing each other. Then Marti spoke.

"Penni. My dahling! You look gorgeous!"

************** Reality check #1 **************

OK. So just what was going on here. A pause for thought is needed. Martin and I - two nearly-middle-aged men, reasonably fit and manly and macho and all that stuff - were facing each other, totally tarted up. Martin had gone for white-and-red, though in similar garments to myself. OK, so he was blonde, long flowing blonde locks cascaded over his neck and some way down his back. But with a white top and red skirt, and red high-heels too, almost as high as mine. Like me he liked to show his bra through his top, scarlet red of course.

So there we were. Two guys dressed as women. Did I feel foolish? Hell, no. It may have been the very first time I'd dressed in company but I'd been mentally preparing for this moment ever since we'd stared thinking about it. And Martin's first words, or rather the way he said them, seemed totally the right thing to say, and in the right sort of affected effeminate voice too. It's all in the mind, you see.

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"Why thank you, Marti, my dear. And may I say you look totally delicious too!"

We each stepped towards the other and air-kissed each other's cheek in a totally girly way. Both not wanting to spoil our make-up.

"I do like that skirt, Penni. Only a total slut would wear a skirt so short, my dear. Clearly you're on the pull, as it were."

"Maybe I am, my dear. We'll just have to see. You're not exactly Miss Prim yourself, Marti, not in fishnets and those heels. "

We went on like this for a few minutes, looking at each other and making over-the-top compliments and talking just like ....

************** Reality check #2 **************

Like what? Like two women? Certainly not. In no way would two women have gone on like we did. Thinking back, I think I realise why each of us was behaving in that way. We were just looking for confirmation. Each of us, in wanting desperately to give the impression of being female, was looking at the other - and seeing a woman. As far as I was concerned I may well have been standing in front of a guy in a skirt and make-up but I really didn't see it that way.

I wanted to see - and I did see - Marti. A woman. Not a guy in a skirt, a real woman. OK so not a gorgeous sexy girl, the sort of 'look' we'd both seen with some of the trannies and she-males on the Web, but someone who nevertheless could be thought of as a woman. I think we were both seeing that, because each of us wanted to be seen by the other as exactly that. A viable woman.

OK, I know it's weird. But tranny stuff is like that sometimes.

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Marti invited me to sit on the small sofa with my back to the window, then looked at me and smiled.

"Can I get you a drink, my dear?"

I smiled at her.

"Thank you, honey. A gin-and-tonic maybe?"

Marti stepped across to the large drinks cabinet and opened the door.

"I thought champagne might be more appropriate, Penni. To celebrate."

"Sounds delightful, Marti."

And she poured us each a rather full glass of champagne, then held hers up.

"A toast. To being female, womanhood, to us, Penni."

I repeated her phrase and sipped my champagne.

"So, Penni, please do tell me, what have you been up to lately."

By which I knew she meant Penni, not 'Paul'. As far as that conversation went, Paul didn't exist. She was asking what I'd been doing as Penni, when I'd been able to dress, what I'd worn, what I'd bought and so on. So we spent maybe twenty minutes discussing dressing-up, and make-up, and where we got our shoes, and what sort of lingerie we liked and so on. All the time, Marti and Penni, woman to woman.

Sitting there crossing our legs, sliding fingers with attractively-varnished nails across our exposed thighs, both of us slightly thrusting out our 'boobs' and flicking our hair. Just enjoying it.

It was when I told her about my last 'outing' that Marti expressed surprise, and became rather excited.

"You went out? As Penni? You never told me about that."

"Well, it was only a short trip, my dear. And not in the daylight of course. Don't want to excite the guys too much, after all. Somebody might get the wrong idea..."

"Ooh how delicious. My clit is getting excited at the thought of it. Where did you go? And more importantly WHAT did you wear?"

I have to say my own 'clitoris' was getting a little excited as I remembered the occasion. Causing me, briefly at least, no small discomfort in my knickers.

"I wore this top, and a blue jacket, and a short-ish blue skirt. Not as short as this one of course."

"And stockings?"

"Of course, stockings, and my other high heels. They're black too but not quite such a high heel. Maybe four inches."

"And what happened?"

So I recounted to Marti the whole tale, of my trip out when I'd been on my own one evening. The vicarious danger of going out to my car and driving off while wearing such an outfit. And about going to the ATM of a supermarket the other side of town, a fairly traditional tranny activity. It had turned into my one 'close encounter' with a rather old-ish gentleman who'd appeared out of nowhere and stood behind me for a couple of minutes at the machine.

"And - he didn't - come onto you?"

"No way, Marti dear. I didn't give him a chance. Though I like to think he got a little aroused standing behind me and staring at my miniskirt and heels."