I had a similar experience when I was a teenager. I was at my grandmother's house playing around in the attic. I found a few old bags of clothes that had belonged to my aunts whebn they were teenagers. I was about thirteen and for whatever reason, I tried on a beautiful green dress from the fifties. Wearing it made me painfully horny. Terrified the whole time I was going to get caught, I jerked off wearing the dress. I came super hard and changed back to my own clothes.
Years later, I was thinking back and getting horny and feeling frisky I slipped into a dress my girlfriend had left hanging in my closet. I was young and slim and a little make up and I looked pretty good. I later bought a wig, dressed up, carefully applied make-up and I was a not quite passable girl.
I went for a ride then did this a bunch of times after. I never got pulled over but once I picked up a hitchhiker who was into it. He knew instantly that I was a guy but was into it. He started talking dirty and before long we were stopped and I was sucking his dick. For the first and only time in my life I felt the joy of a man shooting his load into my mouth. After he came he watched me jerk off using dirty talk to excite me until I came all over myself. I outgrew it eventually but still think back fondly.
I was 18 and dressed like a girl, being small and short I really got a lot of attention doing it. One night I was dressed like a teen girl, heading for a friends house, got stopped by a county monty. We knew eachother, he hates my dad, he had me follow him off into this field. Got me in his car and fucked me like the girl I was dressed as, I kinda hated him for it, but never said anything.
Hahaha, #2, sometimes acting like a girl has its rewards.