He would approach unaccompanied women in alleys and courtyards at the east side of the city, bend them over his knee, lift their dress and spank them on the buttocks before fleeing.
The Whipping Tom of 1681 was active in the warren of small courtyards around Fleet Street, the Strand, Fetter Lane and Holborn, where he would wait after dark for unaccompanied women.
[3][4] It was reported that he approached his victims, "seize[ed] upon such as he can conveniently light on, and turning them up as nimble as an eel, ... [made] their Butt ends cry Spanko; and then ...
[5][b] His probable first attack was in New Street on a maid servant: ... who being sent out to look for her master, as she was turning a corner, perceived a tall black man standing up against the wall, as if he had been making water, but she had not passed far, but with great speed and violence seized her, and in a trice, laying her across his knee, took up her linen, and laid so hard up-on her backside, as made her cry out most piteously for help, the which he no sooner perceiving to approach (as she declares) then he vanished.
[18] While many women stopped going out after dark, those that did would "go armed with penknives, sharp bodkins, scissors and the like",[12][19] although one woman who was attacked and spanked stated that her assailant was wearing armour.
[2][20][9] The legal scholar Christopher Hamerton considers that there were some who saw Whipping Tom as a moral crusader, providing a form of social justice against dissolute women.
A local man, Thomas Wallis, attacked lone women, raising their skirts and beating them "with a great rod of birch, that the blood ran down their tender bodies in a sad and dreadful manner".
[11] As an example of this, Toulalan highlights the description of one attack: Mary Sutten the milkmaid of Hackney also deposed that when the prisoner whipped her backside in a ditch near Shoulder of Mutton Fields, to prevent her crying out, he stuffed his handkerchief into her mouth, and would have thrust something else into another place, had not the watchmen come happily to her assistance.
[28][31] Hamerton considers that the reason Whipping Tom's history gained notoriety at a time when sexualised violence was common, was due to the "very deviance that provided the engaging factor".