Combined effort in chat for an idea..

sheepish(DW): maddie: ohhh i got one... Take a naughty pic of yourself for his desktop picture

suchaminx: and put in on, so its a surprise the first time he turns the PC on

suchaminx: maddie: or you could take a picture fully dressed use that, then over so many days, remove one piece of clothing take another picture use that and so on.......until one day .......

sheepish(DW): maddie: and then from there.. once naked.. start adding things.. collar, clamps.. etc