after is not a valid value of transition.
Instead put transition as a property of the :after selector.
div:after {
content: " - positive!";
position: relative;
opacity: 0;
top: -20px;
-webkit-transition: all 3s;
transition: all 3s;
}
div:hover:after {
opacity: 1;
top: 0px;
}
<div>Test</div>
You can also have a different transition on the hover in and hover out state. This allows us to have a delay to show the pseudo-element but no delay to hide it.
div:after {
content: " - positive!";
position: relative;
opacity: 0;
top: -20px;
-webkit-transition: all 250ms;
transition: all 250ms;
}
div:hover:after {
opacity: 1;
top: 0px;
-webkit-transition: all 3s;
transition: all 3s;
}
<div>Test</div>
Here is a list of browsers that support transitions on pseudo elements:
http://css-tricks.com/transitions-and-animations-on-css-generated-content/