Oxford-born McCleary spent much of his youth playing at non-league level before shooting up the footballing ladder when he joined Nottingham Forest in 2008.
The 25-year-old went on to make over 100 appearances for Forest and was voted Supporters' Player of the Season last year.
His exceptional campaign, which included a four-goal haul against Leeds United, caught the eye of a number of clubs but McCleary says he only wanted to leave The City Ground to go to Berkshire.
"My agent had told me Reading were interested and I was more than willing to listen. I know of a few other clubs who were looking at me but I only really wanted to hear what Reading had to say," he said.
"I'd met with the manager and he made his intentions known and spoke about his plans for the club. Nottingham Forest wanted to keep me and it was very hard to leave. I have so many good friends there and everyone has been brilliant with me. But when an opportunity like this comes along you have to take it. You may never get another chance like it in your career. I had to take all that into consideration and come to a decision."
Reading's attempts to sign McCleary were helped by the fact that manager Brian McDermott has known about the 25-year-old's talents for a while.
The pair both passed through Slough Town - McDermott as a manager and McCleary as a player - and the winger obviously made a lasting impression on Royals' boss.
"I know Brian McDermott was at Slough as well, in fact, he spoke about it the day I signed for Reading. He said he's known me since I was a youngster and had been following me for ages," said McCleary.
"I suppose I've come a long way since those non-league days if I'm honest."
Indeed, with Reading now plying their trade in the Premier League, McCleary's rise up the footballing ladder is all but complete.
Next the winger will be competing against the likes of Manchester City, Manchester United and Arsenal as Royals bid to cement their spot in the top flight.
Asked who he is most looking forward to playing, McCleary said it still hasn't sunk in that he will be up coming up against some of the biggest names in world football.
"There are so many players I really want to go up against and test my ability against them," he said.
"I'm a winger so I really admire players like David Silva at Manchester City, Aaron Lennon, Theo Walcott and Alex Oxlade-Chamberlain. To think I'll be playing against them soon is hard to take in at the moment."
"But you've got to believe in your own ability. Hopefully with some hard work and bit of luck I will be okay at the top level.
"I will get my head down and work hard and try and take my chance when I get it."
McCleary, who has spent most of his career playing on the right wing but can also switch to the left side, will face stiff competition for a starting spot next year.
Reading already boast a number of talented wide men including Jimmy Kebe, Jobi McAnuff, Hal Robson-Kanu and Michail Antonio, who enjoyed an impressive loan spell with Sheffield Wednesday in the second half of last season.
But McCleary believes the competition will bring out the best in him and he is looking forward to challenging in the top flight.
"It's going to be hard for me because there are already some very good players in the Reading team. I'm looking forward to meeting them all in training and trying my best to impress the manager," he said
As well as his Reading ambitions, there is also the prospect of McCleary playing at international level, although he admits that is not something he is thinking about yet.
"It would be something I'm interested in but that's a long, long way off," he commented.
"Hopefully I can do well in the Premier League and we'll see what happens.
"My parents are from Jamiaica but I'd want to play for England first and foremost.
"But one step at a time and I'm certainly not thinking that far ahead."