With the server version, the ui is harder.
Using system.drawing means the server creates a img file and returns. The page will have a img ref. This will either be a separate request, which requires the server keep track of the previous drawing or use hidden field and return a data url ( which will increase download size)
You will also need to tell the server to regenerate the image on click. You can make an img button, and on postback the browser will send the coordinates. Or You can use JavaScript to send the click coordinates to the server via the query string of the img, or use Ajax to get the img as a dataurl.
You will also need a way for the server to keep track of the current image. You could cache and use a unique id
<img id=“theImage” href=“/getimage?id=someid&x=&y=“>
With JavaScript you will need a graphics library.