Former Blues Academy graduate joins Forest
The left-sided player was shown the door in the summer of 2011 by then Fratton boss Steve Cotterill.
Gregory made two first-team appearances for the Blues – both as a substitute in the opening games of the 2010-11 season.
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Hide AdBut at the season’s end he was released, along with Marlon Park, Tom Kilbey, Billy Goddard, Perry Ryan and Ellis Martin.
Gregory featured for home-town club Eastbourne last season but has now bounced back into the professional game with Forest.
Following a successful trial, he has joined the Championship side’s under-21 squad, who turn out in League Two North.
And the youngster is delighted to have another opportunity in league football.
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Hide AdHe said: ‘It has been a long journey with ups and downs, but I knew I had the ability and it was just a case of keep on going.
‘Forest is a huge club and I feel honoured to play for them.
‘If I can show what I can do then I feel I have a real chance to push on.’