The same as a shoejob (a footjob with shoes/boots on) but specifically with high -heeled shoes or boots of some sort. High heels are a sexual fetish object within themselves; a heeljob is masturbation of the male by a female using her high-heeled footwear as the only or main means of contact. The act generally puts the female in the dominant position as there are usually undertones of masochism on the part of the male. The experience is often enjoyed by the female and some will even reach orgasm themselves as the male reaches his climax and ejaculates. Some see it as an act of goddess worship, a sort of offering by the male at the feet of his goddess. Others see it as the complete humiliation of the male, as basically his precious life giving semen is only fit to polish their high-heeled shoes or boots; their own phalluses (the heels themselves) have won over his!
She felt her own orgasm rising inside her as the heeljob she was giving him came to an end and his semen spurted all over her new high heeled shoes!