Alan Elder and Paul Stirling allegedly launched the attack on the vulnerable lad in Edinburgh city centre last year.
The boy, now 15, said he was befriended by Stirling as he made his way along the city’s Lauriston Place before they met up with Elder and a third unknown man.
He said after being led into the secluded Niddry Street he was suddenly punched to the face by one of the men before being robbed of a £1000 neck chain and a £300 designer jacket.
The boy added the men also stole a pair of earrings worth £200 and a £180 hat as well as his mobile phone and a vaporiser.
The boy told Edinburgh Sheriff Court he was left “anxious and scared” following the afternoon attack on December 11 last year which left him wearing just a t-shirt and jogging pants.
Elder, 30, and Stirling, 35, are standing trial on indictment at the city court accused of the assault and robbery of the 14-year-old boy. Stirling is also facing allegations of possessing a knife and a pizza cutter at Shandwick Place, Edinburgh, and to resisting police arrest, both on January 20 this year.
The court heard evidence from the boy via video link who said he met up with Stirling near to the capital’s College of Art around an hour before he claims he was attacked and robbed.
He said: “The man [Stirling] walked past me then came back towards me and started a conversation. We were chatting and he walked beside me.
“[As we headed to the Royal Mile] at that point he said he was looking for some of his friends and he then met up with two men.
“I tried to walk away but felt pressured so I walked with them. We went down a side street. I stopped near the top and the men were walking down the street then stopped.
“They didn’t want to let me walk away and I stood against a doorway. One of the guys started touching my neck because I was wearing jewellery.
“He removed it [a chain] and I became really unsettled. Then one of the men punched me in the face - there was no warning.
“At that point they decided to steal a number of my things. They took my hat, earrings, chain, my phone, a jacket and a vaporiser.”
The boy, who cannot be identified due to legal reasons, added he was then warned “not to tell anyone about it” before the three men made off.
During cross examination the young boy admitted to drinking around half a bottle of Buckfast before meeting the men but denied he had approached Stirling in a bid to sell his mobile phone in a bid to raise funds for more alcohol.
Stirling and Elder, both from Edinburgh, deny assaulting and robbing the 14-year-old boy of his belongings at Niddry Street, Edinburgh, on December 11 last year.
The jury trial in front of Sheriff Donald Corke continues.