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In this diary, I record my life as a transvestite. Perhaps it will help somebody else, who finds their lifestyle doesn't quite match that endorsed by the 'tranny mafia'. Well, I've been there... and survived. The debriefing starts here.

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'Catherine'
1:30 a.m. -- 2008-08-21

It's time I told you about 'Catherine'. Have I been putting it off because I'm acutely embarrassed by the whole thing, or merely holding on to this particularly juicy morsel of gossip from my past? Maybe a little of each... but I'm determined not to lie by omission, so this is a tale that must be told. This is one of those "names have been changed to protect the innocent" things, although 'Catherine' was perhaps less than innocent.

The year was 1996. Costas Simitis had just been elected president of the Panhellenic Socialist Movement in Greece...

Okay, I'm joking. I don't actually remember that. But I think it was 1996.

'Veronica', whom I have written about before, had put me in touch with another UK-based cross-dresser, suggesting that maybe we should get together.

A few months before, I'd had a great time meeting 'Rebecca' and 'Helen', and spent a very pleasant evening in a London pub (in 'bloke mode' I should explain). That had been my first experience of meeting kindred spirits, and I was really looking forward to repeating it. 'Catherine' and I exchanged a couple of emails, had a telephone conversation and all was arranged. I was invited to 'her' home, and encouraged to bring some girlie clothes so we'd actually meet each others' femme selves as well.

Seemed like a fun idea.

I had a heart-stopping moment when 'Catherine' proposed meeting me at the station en-femme. Bearing in mind how thoroughly cautious and secretive I'd been about my own cross-dressing, I wasn't sure how I felt about being met by a tranny in their full regalia. (Don't believe tranny fiction; very, very few males can successfully pass themselves off as female. So what would a bystander think if they saw me meet 'Catherine' at the station?)

Maybe I worry too much about what other people think, but I was young back then. And I'm allergic to being beaten up by homophobic chavs, you see...

Whatever. Perhaps my lack of enthusiasm was obvious; 'Catherine' was in 'bloke mode' when we met. And thank God for that. He wasn't one of those rare males that have feminine proportions or bone structure.

We had a pub lunch together, talking about all kinds of things, including references (made quietly) to our mutual hobby. Then we went back to his place and he left me in the living room while he disappeared off to begin his transformation into 'Catherine'.

Eventually, 'she' emerged. I gave an encouraging smile and 'she' nervously asked, "Can I have a hug?"

Seriously.

A hug was duly awarded.

When my turn came, I tried too hard to achieve a perfect, smooth shave, and ended up with a cut on my face. The damned thing didn't stop bleeding for ages. D'oh.

Just when it matters, I can be so crap.

It being the early afternoon, I wore a skirt and blouse. Going for what I'd consider a 'girl next door' look. Well, if the girl next door was in the habit of wearing corsetry... we males really do suffer to achieve that hourglass figure!

There was a hug for me, too, and we spent the afternoon experimenting with makeup. Perfume was shared; shoes were admired, and tried on. Basically, I suppose we acted out what we imagined girls do together in their teenage years. It was really quite fun. I felt a little bit awkward, or perhaps I should say hypocritical. In those social circles it's hard to say "you look nice" at times. I have a very critical eye... not least when I turn it upon myself.

Now, I've reported before that there are trannies and trannies. In other words, like any slice of the population that you might obtain, there are differences from one person to the next. 'Catherine' surprised me, for example, by saying "If I won the lottery, I'd have a sex change tomorrow."

Er... you'd what? I mean... if that's what you really want, you're not actually a transvestite. You're a transsexual. So, um... gosh. That's a surprise. Not such a kindred spirit after all.

Fortunately, the path that a person must follow to get sex reassignment surgery is sufficiently tortuous that a person can't just change sex on a whim. So if 'Catherine' has explored all that, in the dozen years since we met, the outcome will have been determined by professional medics. It's certainly not my problem, so I'll leave that there. But it was a bit of a shock - even from a man in high heels.

What was my problem as the shadows lengthened and we both did out best to turn two bottles of wine into water... was that 'Catherine' really, really wanted to have sex with me. Which (I hope you realise by now) isn't what I'm in the trannying business for.

If you read my book report from a couple of weeks back, you'll know about Richard Novic. (You'll probably remember him as the guy with a fondness for carrots?) Novic felt that the ultimate way to express his femininity was to be penetrated by a man; and here was another example (actually the first one I encountered) of the kind of tranny who glibly describes himself as "bi when dressed."

'Catherine' wanted the same. It was a toe-curlingly embarrassing moment, made worse by the ineptness with which the plan had been put into effect.

I have to admit, I was a tiny bit turned on, simply because I was dressed as a girl, and that always has a sexual component for me. It didn't have anything to do with the presence of my host, though, who was beginning to show a certain amount of five o'clock shadow through his Boots No. 7 concealer. Trust me; it's not a sexy look.

Next objection: having been plied with alcohol for six hours or more, I was almost certainly cock-cripplingly drunk, so I doubt I'd have been able to oblige.

There's also the somewhat ludicrous context, in that I was feeling girlie too... freeing my male equipment from its foundation-wear and using it to penetrate 'Catherine' wouldn't have been a very girlie thing to do, would it? No thanks.

And finally, he wasn't to know, but there was that unhappy event in my childhood which has left me with absolutely no interest in anal sex. In fact, on this occasion it provided me with salvation; I recounted the tale of my being indecently assaulted (or whatever) when I was little... and promptly dissolved into a tearful, snotty mess. Again, this is not a sexy look.

Sympathy, apologies all round, et cetera.

If I'd been less thoroughly f*cking stupid I would have seen the way things were heading. I'd have drunk less, hugged less, responded differently to the situation. I live and learn. For example, I learned that a packet of condoms sat on top of a fridge-freezer is not an innocent failure to put your shopping away. It seems, instead, to be a coded message that means "I'm hoping this is leading towards some gay sex."

Fortunately, 'Catherine' was really understanding, and very decent about the whole thing. I was sent abject apologies in an e-mail a couple of days later. We spoke on the phone a couple of times, too... but it seemed that we had nothing in common, all of a sudden. We never met again.

Since I have committed myself to being honest in this blog, I need to add another fact. There were some kisses. I'm sure there wouldn't have been, without the alcohol and the cross-dressing... but nonetheless, I have to accept responsibility. (Some people would of course wonder what the big deal is. I think the big deal is more the hypocrisy than the same-sex issue.) As something like fifty percent of humanity already knows, kissing a guy can be quite nice. It doesn't taste weird, or anything. It feels a tiny bit scratchier, and caresses are oddly unsatisfying since one's hands don't encounter the usual shapes; that's all.

It wasn't something that I wanted. Not even in an experimental sense. I'd just as soon be ignorant about what it feels like to kiss a man. It's more that there was a kind of inexorable progression to that stage. A seduction, I suppose. A point came where it would have been unreasonable, childish - even uncouth - to execute a U-turn. But of course, that's exactly what I did, right afterwards.

Even at my most gender-confused, in those dark days after Lucy and I had split up, I was never really tempted away from mainstream sexuality. Call me a soppy sod, but I wanted love, not sex. And I love womankind; I don't think I could settle for a simulacrum of femininity.

So I didn't.

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