From the start I already looked pretty girly, I has a soft smooth round face, curvy hips, small frame etc so I would always get made fun of for not being enough of a boy. One day when I was 18 I met this girl online who would tease me saying what a “pretty girl” I would be. It felt weird, Idk why but when she didnt even though I told her to stop on the inside I kind of liked it, she couldnt see but I would always blush. Our relationship grew and got a little more nsfw with us talking about the porn we watched, our sex fantasies stuff like that. One day she teased me saying “Hey you know what you would look good in? A nice pair of panties! maybe even a skirt!” I didnt know how I felt about this, I was embarrassed but also partially wanted to try them so I asked her honestly “Do you honestly think I would look cute as a girl?” she seemed a bit caught off guard that I went with it but responded genuinely “Yes absolutely!”