Jon Bowles, 46, from Chichester, suffers from fibromyalgia and was determined to raise money for his local support group.
He said the group pulled him through dark days after he was diagnosed with the condition which causes extreme pain in muscles, tendons and ligaments.
After 10 months of preparation, Mr Bowles jumped with the Army Parachute Association at Netheravon, Wiltshire. He was joined by Groupie – the support group teddy bear mascot.
After the jump, Mr Bowles said: 'I'm still a bit stiff around my neck and right shoulder but it was worth it. Wow! What an experience.'
Josephine Fisher, chairwoman of the Fibromyalgia Support Group for Surrey and Sussex, said: 'For Jon, who suffers with fibromyalgia, to undertake this tandem skydive was a personal triumph over his condition.'
Mr Bowles, of Caspian Close, left sponsorship forms every time he made a delivery and many of the group's 400 members canvassed friends to help raise cash – with money pouring in from as far way as Belfast.
To make a donation to the group, phone Ms Fisher on 01403 255450 or contact her on e-mail at fibrojoatsyandsx@hotmail.com