How it all started

[Kitty]

I must have been about 8 years old and seeing my sister in a button up long skirt and thinking I wish I was wearing that.

I wasn't confused by these feelings, I just accepted it. But knew I was probably rare, for a boy to want to dress in women's clothing. But I enjoyed it and I became quite adept at sneaking into my sister's bedroom when she went out to put on her clothes. For some reason I loved her skirts the most.

But as I got into my mid teens I started buying my own clothes through mail order catalogue. I bought stockings, panties, bras, slips, skirts, dresses and shoes.

That was 30 years ago and I am still crossdressing. It all used to be about the feelings I got from slipping on a skirt, dress, heels, etc. But this year there has been a sea change. I actually want to pass as a woman. A convincing - if not ugly woman. LOL. I am realistic.

Rule No.1 NEVER dress younger than your age. For me, it's 45-55. Even though I am mid 40s. Sensible, conservative female clothing, and also the make up.

I never used to do make up, but now I have discovered a look. I can do my eyebrows and full make up. In fact, I have discovered two looks. A blonde and a raven-haired woman.

My aim is to perfect the best I can the illusion of looking like a woman. To be continued...

[Penelope Carol]

Hi Kitty, my way of thinking is very much like yours. I'm 50 but people often say that I look younger. When choosing fem clothes I look for clothes I will feel comfortable in, I really want to be able to blend in with the crowd when I go out. So, I dress my age. I don't say I'm what you'd call a beauty queen but when I took a delivery recently I answered the door in my female guise and the postman did seem a little more pleased to see me than if I'd been presenting as male!

Regards

Penny x

[Kitty]

Hi Kitty, my way of thinking is very much like yours. I'm 50 but people often say that I look younger. When choosing fem clothes I look for clothes I will feel comfortable in, I really want to be able to blend in with the crowd when I go out. So, I dress my age. I don't say I'm what you'd call a beauty queen but when I took a delivery recently I answered the door in my female guise and the postman did seem a little more pleased to see me than if I'd been presenting as male!

Regards

Penny x

Penny, lovely to hear your experiences. Yeah, dressing one's age is the key I think to success.

When my late mother found out I was dressing as a woman she freaked out quite a bit. I heard all the insults. One being 'why do you wear granny clothes?' I'm not sure what she thought I should wear, but it wasn't going to be a micro skirt, six inch heels and a skimpy top!

I would put my style somewhere along the lines of Mrs Thatcher. But I don't think she dressed like a granny!

[Requal Jo]

Thank you for sharing Kitty. I too only dress to my age (over 60 years). I would not feel comfortable to anything but be my age.

[Kitty]

Thank you for sharing Kitty. I too only dress to my age (over 60 years). I would not feel comfortable to anything but be my age.

Agreed, Requal.

That said, anyone can dress any age they want (indoors) but when going out I think we all need to blend. Not stick out like a sore thumb.

Another tip I would give is to wear clothes that are slightly loose.

Tight tops, or anything tight or skimpy can accentuate a man's manly body. And we don't want that.

[Emily]

That said, anyone can dress any age they want (indoors) but when going out I think we all need to blend.

Thank you for sharing, Kitty - and I agree 100% with your statement. Dress how ever you like in the privacy of your own home, but while out and about, dressing to blend is an absolute must!

[Kitty]

Thanks, Lexi.

[Martha]

Thank you for sharing Kitty. I too only dress to my age (over 60 years). I would not feel comfortable to anything but be my age.

Agreed, Requal.

That said, anyone can dress any age they want (indoors) but when going out I think we all need to blend. Not stick out like a sore thumb.

Another tip I would give is to wear clothes that are slightly loose.

Tight tops, or anything tight or skimpy can accentuate a man's manly body. And we don't want that.

Hi Kitty,

I am 57 and am getting close with my wife to going out in public for the first time next summer. I do need to dress more conservative but I still like short skirts. My wife has ordered me some loose blouses and some slightly longer skirts. Just above the knee. Just because your 57 doesn't mean you have to dress like grandma though.

Martha

[April Rose]

I thought I was being sensible, not trying to dress too young, maybe even a little older, since my face is more weather beaten than most women, even my age. I bought a grey wig. My wife hates it. She says it makes me look like my mother.

Awhile ago she decided a lot of my clothes are too dowdy, so we went out to a consignment shop and she picked out a short leather skirt and a leopard print top for me. I'm not complaining!

The way she puts it is; women of whatever age will try to look as youthful as they tastefully can, consistent with their age, but not giving in without a fight.