Dean had Cas walked out the front door towards the stables, Dean tied a rope to Cas' horse just to hold.
"Alright Cas, get up on ya horse I'll be here," Cas was patting Dean's horse before walking over. His hands shook slightly as he tried to pull himself up.
"Need help there buddy?" Dean didn't wait for Cas to speak, as he pushed Cas up.
Once Cas was seated on his horse his eyes widened "D-Dean.. I'm not sure about this.." Dean patted his leg.
"Hey, at least you're on the horse now!" Dean gave him a smile, before telling him to hold on.
Cas listened to Dean, holding on the saddle with Dean praising him all the time making him at ease.
Dean had noticed the way Cas' back straightened up the more he got used being on the horse, as well as Dean telling him how great he was doing.
Once they got back to the stables, Cas was smiling at Dean "did I do good? Even if all I did was sit on the horse?" Dean chuckles "yes Cas, you did awesome, now let me give ya somethin,"
They both smiled at each other, Dean leading him to a small room inside the stables.
"Lets have some fun..."