Trials and Tribulations of a cross dresser

Funny story written by IainB

Sunday, 12 August 2012


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This isn't me.

You turn up for work once in a wig, heels and a dress, and that's it, you're branded forever as a cross dresser. From that point on, every charity event, work's night out involving fancy dress and dress-down Friday, you're expected to turn up dressed as a woman. Eventually, even an alpha male will give in and admit his feminine side. And I'm anything but an alpha male.

Well, okay, I admit it: I quite like it. I don't look that bad. But to be frank, occasionally, I'd like to do something different. My wife's no help. Her and her friends think it's hilarious. My boss is one of my wife's friends. Yes, we've been out as a threesome. And okay, I do have a good time. Don't tell my wife, but I love the feeling of a skirt. The Scots have it right. If I wasn't a transvestite, I could quite go for being Scottish. Having said all that, it would also be fun if I went out in trousers and a shirt. For a start, I would get chatted up less. The Scots can go out in trousers and a shirt. How difficult is it to become Scottish?

An example: We were having a charity ball at work. It was a James Bond theme. Obviously, I went as Pussy Galore. At least the cat-suit had trousers, even if the heels were six inches high. It was my wife's idea, despite me not telling her what the theme was; leading me to suspect my boss told her. At the party, one of the sales guys, who'd come as Blofeld, completely didn't recognise me and chatted me up. He was drunk, he was desperate, he was cute, what? No, scratch that last one... There was quite a lot of hilarity at his mistake. If people I work with can chat me up, you can understand why a night out with the wife has become less and less fun. I don't want to be chatted up. I'd also quite like to drink a pint of Guinness or foreign lagers straight from the bottle without the rest of the bar looking at me like I'm a freak.

For any women out there reading this article, I have to tell you that being a man is brilliant.

I like it. It's fantastic. Some days, even though I really need to...I don't shave.

Although I have embraced my feminine side, being a girl is expensive. You might not realise this girls, but you're male partner's entire wardrobe probably cost less than that gorgeous pair of heels you bought last week. Maybe that's an exaggeration, but it's not far off. Now I've got a half and half wardrobe. Most of the stuff I own, I've worn once. Each new do comes along, and I immediately think "I've got nothing to wear" making me more female than I'd like. It's annoying. Nothing to wear? I've got a really nice shirt from Bench. When am I going to wear that? As well as the expense of my female side (have you seen the price of concealer?!) I still have my male side. I go through a lot of razors these days. I have developed a liking for good male clothes too. Pre-cross dressing, I'd have gone outside in an entire outfit bought at a supermarket. No longer. I also take more care of my appearance. No longer do I just stuff donuts in my face, I have my size fourteen figure to consider!

Don't tell my wife (assuming you can find her!) but I now know a few transvestites and cross dressers. They think my situation is bloody marvellous. Oh, in case you were wondering, the difference is that a transvestite has been out in public. A couple of them are still in the closet. To me, it sounds quite cosy in there, but I was locked out of the closet without ever realising that I could have gone in it. More people knew about me before I knew about me. Apparently, if you're not in the closet, you're not allowed in. In this respect, it is like an exclusive club. Oh, and if you're struggling to get in that new club in town? Slip on a minidress, five inch black heels, pump up your boobs, and try again. We had no issues at all, proving bouncers are as blind as most men when faced with good calves.

I have bought clothes on my own, so I guess I'm a convert. I should just accept it really. I struggle with shoes as I am a size ten. This is quite big apparently. As far as women's shoe shops are concerned, you might as well ask for the rest of the clown outfit to go with the shoes. Most of them go up to eight and then tell anybody with bigger feet to try a specialist retailer. My specialist retailer is on-line. Putting on a pair of heels has an odd effect on me. If I'm stressed, they can instantly calm me down. I don't know whether this is a physiological thing, or entirely mental, but I reckon that for any meditating monks that are struggling to reach Nirvana, slip on a pair of peep-toe sling-backs and they'll be there.

My wife is pushing me to grow boobs and get my ears pierced whilst at the same time maintaining she's one hundred percent straight. I don't fathom. Unless… she is secretly a post-op transsexual, and straight according to birth gender. I wouldn't put it past her. Between you and me, I have started making all my own food and drinks; just in case there's something slipped in there on a regular basis. I'm checking my chest more frequently than a mammography technician.

I realise I'm making this sound all bad.

It's not.

The sex has been brilliant lately. Even when I'm not in a lacy basque, killer heels and lipstick. Also, for those guys that think I'm weird, there's something brilliant about being in a pub in a gorgeous dress from Next, dolled up to look sensational and knowing that despite being taller than the average bear, you still look good. Sceptical? Have a word with your wife and try it. Go on....dare you. I actually made a spelling mistake there that I'm glad I noticed, I mistyped "dare you" and put "date you", easy mistake to make, but it could have been disastrous as I don't have access to a pink carnation.

Since first donning heels, I have discovered quite a few things about myself. I have discovered that no bisexual tendencies, which is reassuring, as I've had plenty of opportunity to explore that side. I love my wife (despite what she's put me through this past two months) and she loves me (I think...). She's certainly (I think...) never cheated on me. I think the dressing up pleases her enough to make us stronger as a couple.

I have come up with a plan to reclaim my masculinity. It's a plan that may backfire.

I am going to tell my wife that I want to transition, and go full time. I will tell her that I'll take the boob pills. Grow my hair, and start saving for the op.

This is going to go one of two ways. Either she'll see the light, or I'll be changing my Spoof name to DebbieB in a few months…Wish me luck.

The funny story above is a satire or parody. It is entirely fictitious.

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