If I understand what you're trying to do correctly, then I don't think this is possible with CSS while keeping the children absolutely positioned.

Absolutely positioned elements are completely removed from the document flow, and thus their dimensions cannot alter the dimensions of their parents.

If you really had to achieve this affect while keeping the children as position: absolute, you could do so with JavaScript by finding the height of the absolutely positioned children after they have rendered, and using that to set the height of the parent.

Alternatively, just use float: left/float:right and margins to get the same positioning effect while keeping the children in the document flow, you can then use overflow: hidden on the parent (or any other clearfix technique) to cause its height to expand to that of its children.

article {
    position: relative;
    overflow: hidden;
}

.one {
    position: relative;
    float: left;
    margin-top: 10px;
    margin-left: 10px;
    background: red;
    width: 30px;
    height: 30px;
}

.two {
    position: relative;
    float: right;
    margin-top: 10px;
    margin-right: 10px;
    background: blue;
    width: 30px;
    height: 30px;
}