This story happened to me a few years ago, I met up with a girl I met online,and we had talked about okinks before hand, but we really started as a normal date.
She had asked me to wear red boxer briefs, and towards the end of the date we were saying goodbye, and she asked if I had worn them. “Yes mistress” was all I could respond. She grabbed my shirt and pulled me close, kissing me aggressively before telling me to get in the passenger seat of her car. I did and then she ordered me to pull my pants down. She teased my cock through my boxer briefs, commenting on how small it is (which is such a turn on for me) and she stroked me for a minute before ordering me to take my cock out and jerk off for her.
I was so turned on that I didn’t last long, before I came I had to ask her permission, and she told me to put my cock back in my underwear and cum in them. I soaked my underwear, and when I removed my hand there was some cum on it, she grabbed my hand and moved it up to my mouth, told me to eat it and then kiss her. It was so hot! As the date ended she told me to wear my cum filled boxer briefs all day, which I did!
It was the hottest experience!