I've cum in my pants loads of times.
Sometimes it has been a deliberate act on my part or hers, but sometimes it's been unintentional - at least on my part. The first time it happened was a at a disco when I was a teenager. My first girlfriend and I managed to sneak into an unlocked store room and were making out like a couple of champs. She had let me put my hand up her skirt and touch her pussy for the first time, and I had actually made her orgasm - completely by accident!
Anyway, after she had done shuddering she reached down and felt my rock hard cock though my jeans and started to squeeze it gently. I was so turned on by actually touching a girl that I lasted about 5 seconds before I gasped and shuddered and shot what seemed like a gallon of cum into my white y-fronts. I was mortified!
She was really pleased with herself though, and this became a regular thing with us. She would let me touch her and masturbate her to orgasm, and in return she would make me cum in my pants. She would sometimes put her hand down my trousers and either stroke me directly or though my underwear, but she never once let me take it out. She said she was worried it would get on her and her parents would see, but I think she was worried that I would try to make her go too far and this was a way of keeping that boundary. I think it also later became a power thing for her.
So I had to always make my way home with my underwear full of my own cum, and a big wet patch on my jeans or my school trousers.
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