When a gang member or affiliated person represents (jacks) two different gang sets. An example of this would be OYs and OGz in the Bronx, New York, who often throw up OY OGz even though they are two completely different gangs.
A fat chic being penetrated by two men in the ass and vagina. Since she is fat and usually disgusting, but willing,the men workfast to get it over with.
Fat susanask bragged about her doublejacking. Shes been much happier ever since.
While our lifespan is the number of years we will live, our healthspan is the number of healthy years we will have and our sexspan is is the number of years we will continue to be healthy enough to continue having an active sex life.
A lighthearted reaction upon receiving disappointing news of some sort. Usually something that isn't a particularly a big deal, esp. when it primarily affects someone else - sort of a mild schadenfreude. Sometimes doubled or tripled, and possibly said in a sing-songy voice for added comedic effect to imitate a muted trumpet, which is how the meme originated.