Michael Merry, aged 55, was on a night out in the holiday resort of Pattaya in Thailand when transvestite Wichai Sripalang began flirting with him at 3am on Sunday outside Go Go bar.
Eyewitnesses said despite Mr Merry saying no, the 24-year-old put her arms around him and 'molested' him, before the tourist pushed her and she fell over.
Sripalang then took off one of her high heels and used it to stab a shocked Mr Merry in the head, leaving a deep gash. Police were called and she was interviewed as Mr Merry was treated by medics, after he was photographed with blood streaming down his face.
Pol Maj Piyapong Ensarn, an inspector of the Pattaya tourist police, said Sripalang waited for officers to arrive after the assault and admitted attacking Mr Merry, reports Asian Town.
He said: 'The transgender woman who approached him and offered sexual services, he declined the offer but she then put her arms around him and molested him.
'This annoyed him and he shoved her away, causing her to fall to the ground. 'When she stood up she took of one of her shoes, and used it to hit the victim over the head.'
Lady boys in Pattaya are notorious for preying on foreign tourists, according to Thai Visa News, and several incidents have been reported of people being pick-pocketed after they were surrounded and hugged by groups.