crossdressing in 2007

Whenever I dressed prior to 2011 my wife was never very happy with it. I think she accepted it was part of me, and we had worked out a way of dealing with it by letting my wife dominate and control my dressing sessions. she'd tell me what to wear and what I should do while dressed. I also learnt a little deportment and improved my look no end.

In 2011 she stopped being quite so concerned about me changing after sessions. Once there were men on the streets also in skirts, she allowed me to dress up pretty much as I wanted though she stopped me from "female impersonations" right away.

She even donated some items - including a couple of dresses and the skirt you can see in this photograph (right) which had a long split up the back. Still it becaem my favourite item of clothing for a short time.

early days - still uneasy in a skirt

My early loooks weren't great though. it took a while to find my look. And work on my figure - like all working class men had I had assumed it was my birthright to let myself go in middle age!

I'd worn make up a little as a crossdresser (above, left) but it wasn't great, and besides the idea wasn't now to look like a woman but to find my look as a man.

Also - keeping the skirt on all day and living your life in it - doing all your jobs, sitting in it for hours on end, walking outside in chill factor winds, etc. all took some getting used to.

One of my first times out in a skirt was the slut walk in 2011. My wife helped me choose the outfit and allowed me to turn up the make-up a little, with well worn tights and a yellow mac, high heels, I walked nervously out to central London via the tube. No one really paid me much attention. I saw the odd guy in the new man-skirts around, but no-one actually in women's clothes until I arrived at the demo.

Later, as one of the first few men to turn up to work in a dress i got sneered at a bit, and called names at the depots etc. For a bit - mostly not quite out of ear-shot. Management intervention sorted them out and of course it was only a few years before we were wearing skirts. Though i didn't know that at the time.

But the female reaction i got was fantastic. Women could be very attentive, sometimes having a feel of my long (conditioned) hair, checking my make-up - most women weren't masculinised yet though skirts were pretty much gone for women in public, they did still lean a bit on make-up (indeed still do), and some tended toward the feminine in their dress. This was slow to go as wardrobes depleted and peer pressure kicked in. Feminine women got called manly-girls - or boy-women.

later: more comfortable

What happened was slowly over next couple of years as men saw the positive female reaction, they started to adopt some feminity in their look. A soft blouse, shorty shorts and tights, or even a skirt or dress. As managers turned up to meetings in smart skirt suits and shift dresses it was commented on, entirely positively and the accusing eyes were turned to those who had not yet moved forward.

I was several steps ahead of most and did feel a little smug i must admit. As well as enjoying wearing dresses in the open for the first time in my life, i was a leader in fashion, and a role model!

Women were now dumping their feminine clothes. And this is how male feminisation was really driven forward.
At that point make fashions were still fairly staid - apart from business outfits and a few leisure items it was bland - with little colour. what moved it forward was ebay and the second hand market generally. women were either handing their wardrobes straight over to their husbands or ebaying it to someone else who wanted it for their husband. Yes, women led this one. Few men knew how to buy feminine clothes or what they should look good in. so women led them.
As men consitently wore more girly clothes that those avaialble in the shops, the retailiers began demanding more antique, feminie attire. And yes - flowrrs and frills began to appear in the men's departments.
Eventually the ebay supply of used clothing ran dry, but by then men were thoroughly feminised and would no more dream of going back to torusers than my father would have of putting on a dress.

an early dress for men