I was introduced to "cross-dressing" by my first partner, who was a much older male.
After months having enjoyable MM sex with him, I would often hang out with him either watching TV or surfing the net. He made the suggestion once, that he thought I would look hot in a short skirt and sneakers. At an impressionable age, I was eager to please so I said I would be open to it to please him. Then one afternoon after sex, he showed me what he purchased online and suggested I tried it on. Obviously we were behind close doors, so no one to see or judge and I felt comfortable to explore.
Fast forward a few months later, when I would come over I change into a short skirt that was so short, you could see my arse and balls hanging as he didnt want me wearing underwear, white sneakers, perfume and a bit of lipstick. I found it liberating to engage with him in this activity and felt sexually very empowered, he very much enjoyed me looking this way, so much so that he would get me to keep my skirt on when he fucked me. While he did feminize me, I did enjoy the experience with him and its not something I regret or at all feel that he took advantage of me. Looking back I think he was missing his wife that left him and viewed me and the sex we had as MF sex.
Today with my current fuckbuddy, he loves when I wear a bikini bottom which I enjoy wearing and its something I can wear without anyone noticing when I turn up.