Emerging sissy / girly side in middle age

[philder74]

Wondering if anyone else here had a girly / sissy side emerge later in life? I'm 49, and over the last few months have started to really feel the desire to explore and express a feminine side. It's not a rejection of male gender identity as such, rather a blurring of the boundaries I've existed within thus far. Have a few sensible skirts that I've worn to a few more kink focussed events, but would really like to explore full sissy headspace and attire. Curious if anyone else has experienced anything similar at this sort of age, and if so, how you navigated it?

 

[Seasonedcitizen]

I had the urge to dress up as a kid many years ago. My advice is to shop at thrift stores for outerwear since it is inexpensive there and use stores for underwear. Don’t go nuts buying a lot of stuff unless you plan to stay dressed most of the time.

 

[Ali123]

I’ve been dressing as a girl since I was 14. My advice would be to go for it. If it makes you feel good, and doesn’t affect anyone else then why not?

When I first started to go out dressed I was worried that everyone would stop and stare, but do you know what? No-one really cares.

 

[BabyTheleste]

I first began exploring my sissy side in my mid thirties, starting with bringing my wife breakfast in bed in her Anne Summers French maids dress. Let’s just say we had a lot of fun that morning and over the coming months I slowly made the outfit more elaborate to get her used step by step to it.

For me it grew as the availability of sissy attire on the internet became more common. Had it not I’m sure it would have remained much more low key. Certainly the type of ultra sissy maid and baby clothes I now enjoy wearing as a matter of course would have been just a dream back in those days.

Another big step was when the children had left home, which immediately introduced much more freedom to dress as I want around the house when I want.