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User / Helene Barclay 1 / Sets / Cross-dressing 2014
Helene Barclay / 37 items

N 39 B 90.2K C 15 E Jun 23, 2014 F Jun 23, 2014
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Another (similar) picture from my cross-dressing session on 3 June 2014, my first in nearly a year. It was absolutely amazing to once more be appearing as a woman. I felt totally at one with myself and very comfortable indeed. As I said in the title I was loving it!

Tags:   transvestite transgender transvestism crossdress t-girl t-gurl gurl tranny trannie mature transvestite

N 64 B 140.5K C 37 E Jun 19, 2014 F Jun 19, 2014
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I am still uncertain about posting to Flickr, my nervousness after the events of last years hostility is not going away easily at all. I actually experience great trepidation with each recent picture I've posted.

It is amazing that many of you have kindly said I do look like a woman but to be honest I personally see myself as a complete failure in this aspiration, to my eyes I look, move and sound like a man wearing a dress, I am hopeless at cross-dressing, I really am. I just cannot see things as others appear to.

As I'm still trying to regain my confidence in dressing as a woman so I thought I would try a short video that undoubtedly is poor in content but I confess despite my lack of ability in looking female I did really get quite a thrill out of appearing on video dressed as a woman.

I apologise for the fact the content of this video is rather pointless, just me driving around and in the last part a lot of blurry slow motion of me glammed up in a ton of make-up and big hair.

The only point I can make with the video is it was all a bit of an adventure and indulging my own fantasies by thinking I could try and look like a woman. That was rather rewarding on an emotional level.

Tags:   transvestite mature tranny trannie gurl t-girl t-gurl crossdress transgender

N 25 B 73.6K C 25 E Jun 18, 2014 F Jun 18, 2014
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I have been surprised by the positive responses to my recently posted photos taken in the first week of June. It was my first time in nearly a year of dressing as a woman and I did have a lot of fun and reward from the experience.

I was very much out of practice and all over the place and this manifested itself as swapping wigs all the time. I loved the short hair wig style but just before I settled on that look I was drawn to a longer wavier style.

I am now in my mid fifties so my looks, not that I ever really had any, are fading now and my skin is getting rougher but such is the way of things. I wanted a photo in harsh sunlight to really reveal how I look and I got one! It does not mean I cannot enjoy the delight and thrill of wearing make-up, lingerie, dress and high heels, I adored my male to female cross-dressing experience, it felt amazing!

I have no real idea why I feel a desire, indeed a need, to dress as a woman and try and act is if I am female, all I know is I feel real joy and inner comfort when I do engage in transvestism, it is always a fulfilling and satisfying experience. I am aware I look rough and not really feminine but I still feel delight when I attempt to try and look like a woman. I simply have to set free this aspect of myself now and again..I love it too much to give up on it.

Tags:   transvestite trannie tranny t-girl gurl transvestism crossdress

N 55 B 102.4K C 39 E Jun 11, 2014 F Jun 11, 2014
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Nearly a week has passed now since my return to Flickr. I was certain my return would, like most of my photos and videos, be of little interest to anyone so it came as surprise that my first cross-dressing photo of 2014 was received positively. I thought I may as well post another as there were some kind and encouraging comments posted. I was particularly delighted to receive some lovely e-mails about my return and how I looked in that first 2014 photo.

My current ambitions, indeed dream, is to see if I can one day actually look like a woman. I am now older, in my mid fifties and I aspire to look stylish, well dressed and with nice make-up and hair. I am not pretty or good looking so the challenge is to try and make the most of what I've got. The aim, though it would be nice to look attractive and feminine, is more to look convincing as a woman as I cannot ever be a beauty. My approach is more be the woman I can be not the woman I want to be. This approach proved incredibly rewarding last week and I adored my time as Helene and felt good within, In fact if I daresay so, I experienced real joy and even now over a week since the photos were taken I am still euphoric.

Personally, I feel this photo is probably the closest I've ever come to my ambition to look like a woman as I decided to forgo all the usual cross-dressing influences and choices I go in for. My approach was to seek realism with my appearance and try an pass as a woman. I enjoyed this look considerably but I will acknowledge it is not going to capture much attention as the motivation behind it is deeply personal.

As for returning to Flickr, the truth is I need an outlet to express my Helene persona and Flickr used to enable that until the hostility I encountered last July, which I must admit nearly killed off my female alter-ego forever. I was hugely undermined and experienced a spectacular loss of confidence.

For me, knowing I don't look that good as a woman, I tended to use the photos as a platform for writing an accompanying narrative, it was my only outlet to talk freely about my dreams, views and thoughts on transvestism and provided a much needed vehicle for self expression. It was my narratives that came in for a lot of hostility and it has been frustrating over the last year not being able to open up and express my thoughts, concerns and pose questions I hoped others may respond to.

I will say I am now very wary of Flickr and how my pictures will be received as it was bruising last year and I don't know if I will ever be able to return to being the Helene I was last year. I feel things have changed in my Helene life now and the old delight I used to experience when posting pictures and videos and writing narratives is considerably diminished due those hostile experiences.

Tags:   transvestite trannie tranny cross-dress t-girl gurl transvestism

N 54 B 95.8K C 53 E Jun 5, 2014 F Jun 5, 2014
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My first cross-dressing session since July 2013, a long time coming. I was not going to return to Flickr after the negative attacks on my photos, videos and narratives from July last year but decided I should not let the detractors hound me off the site. This is my first picture post in 10 months. It captures a rather wonderful moment for me this week. I adored being Helene again, I have missed being her more than I realised.

Tags:   transvestite transgender tranny transvestism crossdress t-girl


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