I Want To Walk Around Like That
Try underdressing at first. When I was your age and a twink I would wear tan pantyhose under my jeans as I walked around midtown Manhattan. The feeling was so incredible. I would find ways for guys to catch a glimpse of stocking at my ankles which at times led to me being in a video booth at an adult bookstore or an apartment where I was then felt up and sucked off in nothing but my pantyhose. So many incredible orgasms from those days. I still wear today and still get the attention.
Go for it. I walk around town wearing women's clothes.
there are a lot of form enhancing padding out there now: stick on, wearable, or otherwise. you need not worry about an "ugly" body, enhance it with padding in the right places.