Cross-dressing 2023
8 photos, 3 videos
Cross-dressing pictures taken in 2023
Cross-dressing 2022
3 photos
Cross-dressing 2020
19 photos, 12 videos
Photos of myself cross-dressed as a woman taken throughout 2020.
Cross-dressing 2019
13 photos, 5 videos
Pictures and videos taken during 2019 of myself cross-dressed as a woman.
Cross-dressing 2018
9 photos, 4 videos
Images from my cross-dressing opportunities in 2018.
Cross-dressing 2017
13 photos, 3 videos
Photos of myself cross-dressed as a woman taken in 2017.
Cross-dressing 2016
6 photos, 2 videos
Photos of me dressed as a woman from 2016
Cross-dressing 2000
2 photos
My very first cross-dressing pictures. I began to practice as a transvestite in mid November 2000 after over two decades of suppression, what a wasted period of opportunity!
Cross-dressing 2014
36 photos, 1 video
Dressing up as a woman in 2014
Cross-dressing 2013
5 photos, 2 videos
Photos of myself cross-dressed as a woman taken in 2013.
Risqué
1 photo
I do on occasion like to attempt more risqué female portrayals. This is a collection of my rather inept efforts to try and carry it off.
Cross-dressing Videos
48 videos
Videos of myself cross-dressed as a woman.
Cross-dressing 2001
10 photos
After over twenty years of suppression I finally began to cross-dress at the age of 41. This set contains pictures of my first year of dressing up as a woman.
Cross-dressing 2002
21 photos
2002 was a year in which my transvestite life took a leap forward and a lot of changes occurred. To date it is probably the most important year in my life as I discovered parts of myself I had...
Cross-dressing 2003
9 photos
Photos of myself dressed as a woman from 2003.
Cross-dressing 2004
20 photos
Four years into my cross-dressing I was beginning to get the hang of male to female transformation. Emotionally I was al ot more comfortable appearing as a female and my fears and guilt about...
Cross-dressing 2005
5 photos
I realised by 2005 that I was set for a lifetime of limited opportunities to cross-dress. I accepted it would likely be two or three times a year I could set free my female alter-ego. This is how it...
Cross-dressing 2006
17 photos
Pictures from my sixth year of cross-dressing. I was getting older but also I hoped more refined as i learned the techniques and practiced transforming myself from male to female.
Cross-dressing 2007
5 photos
2007 proved to be yet another year with few opportunities to dress up as a woman and act female. A brief moment came in the summer and I simply adored indulging myself in wearing dresses, high heels,...
Cross-dressing 2008
10 photos
2008 was to prove yet another fallow year and I only had one opportunity to indulge in cross-dressing. That delightful moment came in August of that year. It felt wonderful to shave my legs, chest...
Cross-dressing 2009
23 photos
2009 was a year I had little opportunity to dress up as a woman but late in the year in December I finally managed to dress as my female alter-ego Helene. It was liberating and euphoric.
Cross-dressing 2010
17 photos, 1 video
Stills of my cross-dressing from 2010.
Cross-dressing 2011
1 photo, 1 video
2011 was a busy time in my 'real life' siomy cross-dressing indulgences were dormant for nine months. Finally in September I had an opportunity to cross-dress once more, it was truly a delightful...
Cross-dressing 2012
17 photos, 2 videos
Cross-dressing pictures from opportunities in 20122