The 18-year-old made his first team league debut in his side's 1-0 defeat at Montgomery Waters Meadow a couple of weekends ago, when he came on for Jordan Shipley in the 81st minute.
The left-back had been one of a number of young players given an opportunity to impress in the EFL Trophy, and with the injury to Geroge Nurse, the youngster has found himself on the bench a lot recently.
And Bailey is enjoying being around and learning from members of the first team squad.
He said: "Joining in with them and travelling with them was good - but to get on the pitch is obviously a dream of mine.
"To become a pro first, but it is very good for me to get on the pitch with the first team lads.
"It was nice to see the fans as well.
"Training with the first team is very beneficial
"I go up and watch them train, but for me to get to the next step I have to take tips from him (Jordan Shipley) on playing as a wing-back.
"It is good for me to go down there and train with them and see the tempo and how they train as they play.
"When I went on (against Barnsley) they started talking to me and instructing me on how they wanted me to play.
"So it was good to get involved."
Town have a lot of home-grown talent on the bench.
At Sheffield Wednesday at the weekend Josh Barlow, Declan Hutchings and Tom Bloxham joined Bailey which is a testament to the academy program headed up by David Longwell and Charlie Musselwhite.
His manager Steve Cotterill has given lots of players their professional debuts - many of whom have gone on to have long and distinguished careers.
And Bailey is enjoying working with the experienced boss insisting he is helping him to keep improving.
He continued: "He has given me more confidence in myself, and playing me must mean something to him.
"He trusts me - and I trust him - there is a great pathway here that is good for me to go up there and make my debut.
"I am very happy with how he is with me.
"In a few years or so I would like to be a started in the first team squad hopefully at Shrewsbury.
"That is my ambition while I am at Town."