Cuttyng is first heard of early in 1367, when he and other burgesses of Wilton were accused by the prioress of Studley of carrying off 40 cattle and 500 sheep, worth £100, at Warminster and Wilton, of assaulting and imprisoning her servants at Wilton, and of abducting one of her bondwomen there. A royal commission was set up to investigate the charge, but what resulted is not known.
First returned to Parliament in 1377, Cuttyng thereafter sat for Wilton on six further occasions. He also served eight times as a tax collector in the county at large. Meanwhile, he had acted as surety for the attendance of Adam Daubeney at the Parliament of 1385. Three years later, together with William Chitterne and John Cole I, he was made responsible for repairing bridges at Wilton, a royal grant of pontage for two years being made to them on 4 May 1388 when Cuttyng was sitting in the Merciless Parliament. Cuttyng’s name frequently appears as a witness to deeds relating not only to Wilton but also to Fisherton Anger, the neighbouring suburb of Salisbury.
By 1384 Cuttyng enjoyed a remainder interest for life in a moiety of the manor of Poulshot, then held by Agnes Cuttyng (perhaps his mother). Ten years later he was in possession of property at Wilton and land nearby, at Ugford St. James, and in 1402 he acquired yet more at Warminster and Bugley. In 1412 his holdings in Wiltshire (which by then included estates at Poulshot — presumably the moiety of the manor — and Burcombe) were assessed at £17 6s.8d. a year, and he was also said to hold lands in Dorset.