This is a very early photo of myself attempting to dress up as a woman, I was age 42 at this point. I had only acknowledged to myself I was a transvestite a few months prior to this picture being taken so I admit I was not very good at applying make up, wearing a wig and wearing women's clothing. I was rather elated at the time though and regretted my twenty years of suppression.

Tags:   transvestite crossdress t-girl transgender transsexual transexual t-gurl gurl drag transvestism transsexualism female impersonator female illusion male to female female impersonation tranny trannie trans queen glbt m2f m to f crossdressing crossdresser gender gay lesbian effeminate boy to girl acting performance wig makeup dressing up as a woman

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Searching through my cross-dressing photos has been both revealing and fun lately. I'm trying to build a timeline sequence showing my evolution as a transvestite from my emergence from the closet back in November 2000 up to the present day. I'm planning a documentary video about being a transvestite for eventual posting onto You Tube. It is a self indulgent vanity project with no definite dates for filming or completion. I see it as a long term work in progress but one I am now keen to make as I now feel confident enough to speak openly on camera about my transvestism.

One aspect I wanted to highlight were my off the rails naive dressing up as a woman moments in my early period. I was completely obsessed with wearing mini skirts, showing off lots of leg and having long hair. I feel this picture taken on a self timer using the built in flash on a compact digital camera back in 2001 perfectly captures my naivety in how I should dress as a woman. I was 42 years old in this photo and dressing like I was 17! I think we've all done this but as my focus over the years has shifted to trying to portray myself as a convincing illusion of being female I think I have somewhat better taste in women's clothing these days!

I think it is great though to be open about how one used to dress up and recall the excitement and highs of those tentative early days of being a man who began dressing up as a woman. It was quite an emotional but joyous period in my life.

Helene x

Tags:   transvestite crossdress t-girl transgender transsexual transexual t-gurl gurl drag transvestism transsexualism female impersonator female illusion male to female female impersonation tranny trannie trans queen glbt m2f m to f crossdressing crossdresser gender gay lesbian effeminate boy to girl acting performance wig makeup dressing up as a woman

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This is a shot from the summer of 2001. It was my first year of cross-dressing and I was age 42. I had only come out of the closet the previous November and for me to go outside dressed up in make up, wig, skirt, high heels wearing false breasts was a very exciting moment. I adored the soft caress of the summer breeze against my shaved smooth legs clad in tights. I enjoyed the whole experience of walking in the tight skirt and heels and the delightful feeling of the tight fitting clothes.

I had my phone with me which I answered as the self timer counted down for the picture. The image reminds me of what might have been if I had been born a girl. I could have been taking a call from my boyfriend who desired me for the woman i was.

Of course a complete fantasy as I'm a man and I'm not sexually attracted to men. However, as a woman men fit the portrayal so as a woman I like to act as if I am female with men but avoid intimacy. I love the performance required to act this way and pretend to be what you are not. I always feel if you can crack this one and act female enough then it is exhilarating.

I really do enjoy trying to pass myself off as female but after a lifetime of questioning myself I am more aware of my sexuality than ever before. It does kind of frighten me a bit that I try to be a woman so much and interact as a woman may with men and talking about them, but I now see that as part of the act. If I'm a woman then I really need to become one to make her work convincingly. Deep down I know I'm a charade so it is more of a thrill than a realistic desire.

It's a topic many are not happy to discuss but I enjoy exploring it as it actually gives you a lot of self confidence to realise you need to get into a persona to be a convincing woman.

Tags:   transvestite crossdress t-girl transgender transsexual transexual t-gurl gurl drag transvestism transsexualism female impersonator female illusion male to female female impersonation

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I discovered this picture recently taken in early 2001 during my first few months of starting out as a cross-dresser. I was rather naive and learning the techniques required for successful transvestism. I was experimenting with looks, especially my wig styles, make-up and choice of female clothing.

I'm not sure I did very well with this effort but inside I was excited beyond words and truly thrilled to pose for a picture while cross-dressed. It was rather euphoric!

I think it is good to look back and see if one is evolving and making progressions with your female portrayal. I would like to believe I have improved a lot since this very early effort of attempting to look like a woman.

It would be very interesting if other T-girls posted pictures of their own early efforts as I'm sure it would encourage those who are starting out with their own explorations of cross-dressing.

Helene x

Tags:   transvestite crossdress t-girl transgender transsexual transexual t-gurl gurl drag transvestism transsexualism female impersonator female illusion male to female female impersonation tranny trannie trans queen drag queen ladyboy third sex glbt m2f m to f crossdressing crossdresser gender homosexual gay lesbian effeminate boy to girl acting performance wig makeup dressing up as a woman men who dress as women dressing up men up dressing

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Despite wanting to be a girl when I was younger and having a lifetime desire to dress as a woman and become one in my head and how I behave when I cross-dress, I suppressed this powerful emotional desire within me for over twenty years of my adult life. In November 2000, at the age of 41, I finally dressed as a woman for the first time in my adult life and was overcome by that initial experience as two decades of suppressed emotion were finally released and set free my inner female self.

I won't deny I looked a real mess that day, I had no make-up skills, a bad wig, poor choice in female clothing yet the joy, the euphoria, the elation and also great fear came out. I was a wreck, my mascara was ruined yet a new freedom was present within me and I knew a new journey had begun.

I have not travelled far on that journey as my female self only appears two times a year due to the necessary compromise I committed to in my life. By the time I set free my inner female self I was a married man with a family and responsibilities. I have no wish to give up this life which now means more to me than the my inner dream of being female. I do need to express my female self so I have to become Helene at some point. My family though not pleased do tolerate my need and allow me to get on with it quietly on these two occasions each year.

Returning to this picture. I was staying with my daughter who in my early cross-dressing period in the year 2001, recognised my need to learn and experiment and go through the emotional roller coaster of freeing up suppressed emotions. I was left on my own one Sunday afternoon to enjoy my explorations of becoming female. I began by plucking my eyebrows followed by a hot bath in which I shaved off all of my body hair. Next it was the delight of tucking away my genitals (a technique I discovered researching transvestism on the Web) and I attached my breast forms using adhesive to my chest. I then felt I had a female looking body and almost wept with joy as I pulled on my knickers (panties) and fastened on a bra. Suddenly this was it I was going to be a woman…well I hoped I was!

To say I was on a real high would be an understatement. The tactile sensation of being hairless, feeling make-up going onto my face, donning the wig and putting on a dress and stepping into high heels…it was a moment I have never forgotten. My whole life had wanted this moment to occur. A simple act I admit, that of shaving, applying make-up and dressing in female clothes yet it was an incredible and truly liberating experience that had me so light headed I had to sit down and recover for nearly twenty minutes!

After that I was in heaven. I was laughing, smiling, loving it and imagining I was actually female not just dressed up as one. I wanted it to be real, I really wanted it. In this picture I was joyous and truly desired to be female, to be a woman, to be a wife, to be a mother, I wanted the life of a female but bang…I was a man. I can never quite escape this reality but I think to experience a few hours of gender freedom and cross over into what you really dream for is just incredible.

This picture, taken on a self timer, captures me in a private moment but one of sheer joy at appearing as a female and inside my head forgetting I am a man. Helene was no longer a dream she was free. It was about my fourth time dressed as a woman and I was very determined to see if I could actually look convincingly female. Of course I failed, I can see I'm a man in a dress yet within me positive things were happening, I thought I could maybe improve if I put in the effort. This picture was a turning point as I had a small sense of achievement that I may be able to do a reasonable job of looking like I am a woman. Twelve years on from this picture I've not had much opportunity to progress and evolve my efforts to look like a woman but discovering the picture in my archive has brought back those amazing memories from that day back in January 2001, I was given the freedom to free my inner feminine self. I am forever grateful to my daughter for her understanding of my need.

Helene x

Tags:   transvestite crossdress t-girl transgender transsexual transexual t-gurl gurl drag transvestism transsexualism female impersonator female illusion male to female female impersonation tranny trannie trans queen drag queen ladyboy third sex glbt m2f m to f crossdressing crossdresser gender homosexual gay lesbian effeminate boy to girl acting performance wig makeup dressing up as a woman men who dress as women dressing up men dressed up

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