It Started With a Nightie


From what I’ve read and learned there are crossdressers, transvestites and transsexuals to be found in every walk of life, every background and every social group. I don’t think I could come up with one ‘type’ of person who couldn’t fall into one of those categories or another.

Fair enough, not every individual is a transvestite, but I reckon that we all know one without ever knowing it. The nearest to the ‘type’ of person I could think of who was least likely to be a transvestite was me. Now if that isn’t a sweeping statement I don’t know what is, but let me try and explain.

I’m in my mid-thirties and I work in the security industry. I love contact sports, football and rugby. I’m six foot tall, long-haired and I’m a heavy metal loving, part time writer, full time beer drinker. Oh, and I served in HM forces in all the mud and muck that the wetter parts of Europe could supply.

You know the sort, the gun-toting, hard drinking, hard swearing, macho type that terrifies the locals, smashes up bars and the countryside with equal abandon, all in the name of our national defence. Best off all, the good old tax payers paid me and my colleagues for doing it. Travel the world, meet interesting people and kill them. Fun, huh?


When I left the forces I wandered about a bit, met some very interesting people and realised that I didn’t want to kill them. I got a short term contract job with a security firm and moved down South. It was in a not so sunny London that I first came across the ‘alternative scene’. I found London to be a pretty lonely place, busy as hell and full of people, but no one seemed to have a minute to spare for themselves.{product_snapshot:id=560|134}

Unless you got ‘in’ with the crowd quickly, it seemed you were destined to spend most of your time on your own. For a bit of pocket money, I worked the door at a couple of nightclubs, many of which ran theme nights. One of these was a real eye opener for me even though I’d lived in Germany for three years.

Fetish clubs seemed to be springing up all over the place – having seen evidence of one or two ‘fans’ at rock clubs and heavy metal gigs I wasn’t repulsed, but then again I wasn’t particularly drawn to it. I wasn’t really bothered either way, long sifts, little cash and little interest in anything but beer and bands really.

No whether this had planted a time bomb in me I don’t know, but a few years later I read a newspaper advert looking for new writers. One of the subjects the advert requested manuscripts under was erotica, so working along the lines of ‘anyone can write that’, I sent off for the publishers guidelines and got by return a sample of their previous output. One of the pieces was transvestite fiction at its very worst…



Putting my ‘anyone can write that’ attitude next to my very limited knowledge of fetish clubs, I set off and began writing. Easy as that, no problem, even my four finger typing couldn’t keep up with what was pouring out of the word processor.

Heady stuff this sudden creativity, it isn’t until you’ve read it over that you realise how bad it actually is. Descriptive, suggestive, sensuous, whatever words I tried to apply to the stories and tales didn’t quite fit. I’m biased enough to say it was good, but it lacked feel, missed intuition.

I couldn’t express what the characters felt when they were dressed or forcibly dressed, what was it like to put on lipstick or to wear spiked high heels? I didn’t know, and there’s nothing worse except writers block than having an excellent idea for a story but not knowing how your characters feel, act or react.


How was I going to get over the problem? Brain wave! Ask my girlfriend! Great idea? Well, yes and no. You see, I’d developed this particular character, Daniel – I’ll leave the plot out for the most part, but he’d fallen into a tangled web involving this mistress, she’d got him to crossdress and I didn’t know what to do with him.

The trouble was doubled in that the more I was writing, the more I was becoming intrigued by the whole thing. I found it easy enough to get into the character’s heads, but I couldn’t get into the character’s clothes, so to speak. If I was already writing good stories, how much better would the stories be if I understood what my character got from crossdressing? Which is roughly where the nightie came in.

The first time was innocent enough – HA! Who am I trying to kid! I don’t know if it was innocent or not, what I do know was that is was as broad a hint as I could possibly have come up with. I sneaked off to bed early one night, slipping under the duvet in the light blue, strappy nightie I’d ‘discovered’. Just below knee length, slightly flowered over the breasts (or where my breasts would have been). Soft and smooth on my skin. Exciting? Yes. Arousing? Definitely.

I lay quietly in bed, nervously waiting for my girlfriend. This nervous anticipation certainly lent an edge to the experience. At worst it would be outrage and disgust, at best she’d just laugh!

As it turned out, it was better than that – it was sensational! To protect the less than innocent I will spare you the details… oh alright then! I couldn’t get my head to follow what my body was feeling, from the touch of Lynn’s hands on me through the nightie, to the way my nipples seemed to set themselves on fire. Lynn ‘asserted’ herself and it came as a very pleasant surprise to me that she loved the ‘power trip’. When she straddled me and took over completely I was totally blown away.

It became a regular ‘nightie’ game, too regular for both of us really so we cooled off from it for a little while. The nightie was still around but it wasn’t on all the time. I explained to Lynn about my problem writing and where the idea for the nightie had come from. If I could work out what it felt like then I’d have a better idea what to do with the characters in the wstory. (I think I’d left poor Daniel standing there in a white lace nightdress and negligee).



After getting the problem off my chest, the writing took off again. I now had the added advantage of Lynn proff-reading and giving me a sounding board for ideas. I was very pleased with the insight into what women get up to getting themselves ready and why they disappear into the bathroom for hours on end.

I’d been writing almost by rote, following the same routine for the characters getting dressed, doing make-up and so on. Having Lyn’s guidance into how women think about their clothes and cosmetics gave me pointers. I was able to channel these into the characters, putting flesh onto the bones so to speak, albeit with a certain amount of guesswork. Some things were apparently sacred.


Somewhere along the line I graduated from the nightie to lingerie – bra, stockings, suspenders and panties. If the nightie had been a shock to the system, the lingerie just about blew my head off. I know that it was a little strange for Lynn, the first time I filled up the bra cups with balled up socks she wasn’t too happy at all. I could see her point, so I didn’t push it, though I think that when she saw what she could achieve by playing with my nipples through the bra, she was as impressed as I was!

After a boozy night at the local we got home and I got it into my head to ‘go all the way’. The beer having loosened my tongue from my brain I asked if she’d mind making up my face. She agreed with the proviso that in the future I was to start doing my own. Watching the transformation in the mirror while she worked, I was astounded by the amount of work that actually goes into making up a face. The change in my looks astounded me even more, once Lynn had attacked my unruly hair I just about fell off the side of the bath…

The make-up kept dragging me back to the mirror, staring at my reflection in fascination, puckering my lips and trying to see the ‘ME’ beneath the cosmetics. I’ve never been particularly fashion conscious, nor have I ever really been bothered with how I look. This ‘other self’ was immediately different though, I was deeply concerned about how my hair looked and what would other shades of lipstick and eye shadow do?

Lynn says she notices a change come over me when I’m dressed, calmer, softer, kinder? I’ve not really explored this with her, perhaps I should, but then again I find the prospect rather daunting. I know I feel much more relaxed and at ease and that I’m intensely aware of ‘myself’. It might be that I’m afraid of losing the feelings and sensations if I try to classify them. There is also the worry that Lynn is merely ‘putting up’ with my sudden interest in crossdressing. I’ve asked her, halfheartedly, if she minds. She has said that she doesn’t and that she actually actually likes it, though I still have the nagging fear that she’ll ask me to stop.


That must be the guilt coming through I guess. Though why I should feel guilty about being a transvestite I don’t know. It’s not as if anyone I know has ever told me that crossdressing is the ultimate evil and that practitioners of this ‘black art’ will be sent to eternal damnation.

Alright, so the media does, and the bible does too. I’ve never paid much attention to the former, and no attention at all to the latter, so, as I don’t really care what anyone thinks of me, where does this guilt come from? I don’t know and I don’t care, but I don’t like it either.



High Heels

My worries over Lynn’s feelings towards my crossdressing were assuaged when she told me she’d love to see me in high heels. Quite where she got this bolt from the blue from I don’t know, but believe me I’m not complaining! She was insistent about it, even down to wanting twin thick buckle straps at the ankle and the style of the shoe!

The enforced change to my posture made me all the more conscious of the whole effect. My mannerisms and movement had to change and adapt, even I noticed this ans I revelled in it. Lynn was so right about the ankle straps, they definitely have an effect.

When I stand up or walk, my back is straighter and my legs appear longer and far shapelier. My steps have to be smaller and neater, calf and thigh muscles stretch delightedly. I’m always filled with elation when I hear the heels click on the kitchen floor.
We are never ever going to get a carpet or carpet tiles in there.

From Lynn I learned that less is often more, toning down my make-up from the full-blown parrot and panda to a more sophisticated look. I remember Lynn’s initial reluctance to kiss me after my first attempt at painting my lips, hardly surprising really as I might as well have used an industrial sized brush! The same conclusion occurred in the boob department. I’m slim as well as tall, so big boobs don’t work – smaller can be more beautiful and I think Lynn was absolutely right.


Being on a restricted budget, neither Lynn nor myself can go on rash spending sprees – thank goodness for charity shops! Whilst our wardrobes are not bursting, they have grown and I’ve a selection of outfits to experiment with. My days off often coincide with Lynn’s work. Well, stick alone in the house with no intention of doing much, a girl has to find something to do, doesn’t she!

Not every day and often not all day, but Lynn will sometimes come home to find me dressed. After a quick inspection, we generally end up in bed, so I guess Lynn quite likes the idea of me being at home dressed while she’s at work

How far one goes is obviously dependant upon the individual. I can only speak for myself, of course, and I know how fortunate I must be compared to some of the other articles I’ve read.

I know I’m never going to pass in public, I would love to do so, but I know that it isn’t practicable. It doesn’t upset me because I can dress more or less whenever I wish and can stay dressed for as long as I choose. I also have an outlet through my writing. It doesn’t really matter whether anyone reads what I write; I can use my creativity to go out for me.

Granted, I’ll never buy a drink in a pub when I’m dressed, or go to restaurants etc, but I’ve done all that in ‘real life’. I combine the memories with what I know through my dressing and I’ve got the best of both worlds.




As for being more convincing, yes, I’d love to be more convincing, to be able to express my ‘other’ self more openly. I am, however, conscious of the limitations and how far I’d be willing to go to achieve ‘convincing’. I fully expect that some transvestites long for their own breasts and would give anything for a course of hormones or a boob job. I understand that some people need to go all the way, to become the person they were born to be.

Me? Well, lets see. I’d love to have a trimmer shape. To that end I’d love to go overboard with corsetry. The idea of my body being forced to adapt to tight laced and boned corsets or basques thrills me. Obviously this would only work until I removed whatever garment it was, but I’m not looking for a permanent change. Then again, I do shave my legs and paint my toenails. I know neither are permanent, but they are longer term, and I often wear lingerie under my ‘normal’ clothes.

For me, the most wonderful aspect of transforming myself is painting my lips. I think that this is because it’s such a feminine thing to do. Similarly, painting my toenails and shaving my legs. I see where Lynn was coming from with the high heels as well, whether or not this is my defining moment, I don’t know. Then again, I’ve read so much on the subject of the ‘defining’ moment that I’m beginning to think mine is the

When I’m alone and dressed, I still get all the sensations that I had when I first slipped on the transvestite road, but when I’m dressed and Lynn is with me the sensations are heightened and intensified to such a huge extent that I sometimes struggle to keep my feet on the ground. I don’t feel the need to dress full time – often I don’t dress for weeks. The sensations and feelings seem to become all the more intense with each transformation, not only for me, but hopefully for Lynn too.

My writing has evolved from sketchy ideas to new heights, opening new adventures of exploration. I’ve also found that writing female characters has become a lot easier for me to handle, seeing things from different perspectives, ones I hadn’t really considered seeing things from. My crossdressing isn’t a crutch for the writing, nor is my writing a crutch for my crossdressing.

The writing could exist without the dressing, but would not be anywhere near as ‘readable’; I can write without being dressed and I can dress with absolutely no intention of writing. I should admit though, that my crossdressing sets my imagination free to pursue ideas that I would never have contemplated without ever having tried on the nightie…

One thing that I am absolutely certain about is that my writing would never have flourished without Lynn being there to prompt and probe.


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