when your date turns out to be chubbier than you expected. If date is female, see also squirting jam into a donut
"She wasn't exactly a blind date, I knew her from highschool but hadn't seen her thru 4 years of university so it was surprise jellyroll time when I picked her up at her apartment."
The act of massaging ones penis in between the rolls of fat of an overweight individual in order to receive sexual gratification.
Bertha was so fat that Billy often found jellyrolling to be a more pleasurable pursuit than the act of coitus, especially when she wanted to be on top.
In the water, at the beach. When the oncoming wave builds up, and right before it breaks. It doesn’t break, and just lets you float right over it. At that point, the wave is called a jellyroll.
I thought that wave was going to break on you. You were caught in the jellyroll.