This is a true story which happened not long after my 18th birthday. I knew these three 20 and 21-year-old girls in town, who were essentially sexual sluts, but because I was 18, they wanted to watch me masturbate in my jeans, and see how big a wet spot I would have. I masturbate a lot in my underwear and jeans, because it's just easier that taking my penis out each time, and these girls knew that from past conversations with me.
They told me $25 per orgasm, maximum of two. I wanted money up front, with a refund for a no-blow. They agreed.
I reached down and started working my dick through my light blue jeans, and got a hard-on fast. Closing my eyes, I found this moment to be really delightful, openly masturbating for girls. Soon I felt myself tense up and shot my load. It was a big, long wet spot down part of my left pocket, and onto my upper thigh. I creamed myself good. The girls were delighted. They even measured my wet spot, and said they really liked watching me do this. Too bad they didn't masturbate, too.
Wearing the cum-filled underwear soon got sticky, as usual, and I got a nice cum stain on the denim fabric, too.
About an hour later, I repeated the process, after allowing myself to reload a bit. I jerked off on the right side of my pants this time, with much the same results.
It was the kinkiest feeling I've ever really had doing that for those three girls. Much more to tell about the conversation, but I won't bother with that here.
A nice way to pick up $50 for sure! Would love to do it again sometime.