So when I was younger I had a girlfriend who was a year older than me, which at the time was like a big deal I thought it was awesome. She wanted to bring me over to her house but her parents wouldn't let her bring any boys over let alone a boyfriend.

So, her idea, her way of getting around this, was to dress me up as a girl. We spent a little over a months of her basically coaching me how to look like a girl, do makeup, make my voice sound like a girl (it was easier then than it is now) then she brought me some of her old clothes after school one day and I changed into them before we went over.

Went to her house dressed as a girl, she told her parents I was a girl from a grade below that she was mentoring and brought me up to her room.

I got my first blowjob dressed as a girl, and then the next day I had sex for the first time dressed as a girl.

And it was great, I loved it, even though it started to get a little weird later on. She told me a while later that she thought it was odd at first but she actually liked dressing me up as a girl, and we never ended up having sex where I wasn't.

We broke up when she graduated, and I met her again later on and she was with another younger guy who she had also convinced to crossdress, this time because she wanted him to though and not out of necessity. He was wearing a collar when I met him.

Meanwhile I'm pretty sure that whole relationship is why I have a thing for crossdressing myself now.