Bum

[SideSet]

Wondering how many of us started crossdressing about the time we were developing?  Also, was it just breasts, or other parts of your bodies that were developing?

For me, I developed a large round feminine backside even before my breasts had grown much.  I remember one time we were lining up at middle school and the boy in back of me said my "ass was so big you could pin a medal on it."  

By then I had already been trying on some of my mother's things.  Interestingly enough, not yet bras; they would come later.  Mostly her panties and girdles and stocking and pantyhose.  I found an old pic I took of my backside in her panties.  I wish I could find some of me in her girdles and such.

[aboywithgirls]

Most of you know when and why I started wearing a bra. At my first bra fitting, I found out that I was a 34C. I had a feminine shape on top and bottom with long hair. I even had a unisex name. After I found 5 or 6 bras that I liked, the SA asked my mother and I if I needed any panties. I just looked at my mom. She said "your the one who's going to wear them." The SA definitely thought that I was a girl and we never bothered to correct her. That's when I started wearing panties from that day on. The rest of my journey toward womanhood was gradual and natural. 👭

Sophie ❤️ 

[Orb]

Side Set I can remember much of the same in my youth.  I fought hard to suppress those urges and feelings. 
I did know I liked it and felt comfortable then.  It's all a lot clearer to me now.
 That's why as we as a nation struggle with the gender issue I hope it's easier for those coming of age now.  I have to say I think it's getting better.

[SideSet]

Back then it felt wrong but it felt right.  It was confusing and conflicting 

[Gino]

I have never thought of it as crossdressing, just clothes I loved. My story is very different than most here, but now that I am retired I wear clothing designed for women about 95% of the time. I love the feel, and look of the clothes I wear now. I have never been what the world considers a real man and that is ok, I am just being the real me, panties and all.

Your story sounds much like mine. Being on the petite side in a man's world at 5'3" men's pants, shirts and even shoes (I'm a size 7 men's) are generally unavailable and just  about everything I buy is ill fitting even if I have it altered. 

So, I have always gone for the androgynous look. Now that my hormonal changes have brought me breasts I wear sports bras to hide them. 

[aboywithgirls]

I spent several years shopping the ladies stores and departments for my clothing before transitioning. 

It was ridiculous to spend $50-$75 on a pair of slacks that fit and looked terrible on me when I could get a pair that looked and felt great by simply looking in a different department. 

Sophie ❤️

[taxmapper]

At 10 my sister had me try on her 4 inch Thigh High Go-Go boots. Then later at 12 had me put on a pair of her high heel Mary Janes.   I was able to wlak just fine in them thankyou very much. 

Then at 16, a friend of mine dared to put on a pair of her high heels. Strangely enough my feet (though flat) were the same size as here and again was able to walk just fine in them.   

I also tell the story of how I was accused of "walking like a girl' and this got me to keep my hips in a straight alignment and walk with eventual muscle pain from my butt as a result. 

I was also told I had a panty waist by my father.   Having always been curious over women's underwear when I was young, I eventually found out the obvious. 

Always fighting urges to do anything other than women's bike shorts.   That's as far as I have taken that except the capris.   

I still cant understand why i keep getting upset that I have no hips to speak of. 

[Orb]

Last week I walked through the men's side and the rack said, Men's and Ladies T's.  I bumped into a lady friend and she was there, in the men's side, looking at T shirts for herself.  No big deal!
Bottom, pun intended, line is, get what fits.  We are all different shapes, and retailers just want to sell merchandise.