Warden Powder standing at the end of the table rubbing his cock and looking at my exposed asshole.
"This is going to feel so good for me boi!" He said now rubbing his cock on my asshole that he shaved just 24 hours ago.
He could see the nervous look on my face.
"Don't worry boi, I will use a lot of lotion and start slowly."
I felt him pour out a good amount of lube rubbing it all over my ass, slipping the tip of his finger in me. The anticipation was insane! I was nervous and excited, my little white dick straining in its chastity cage! Then I felt the head of his cock pushing at my opening, forceful yet somehow gentle.
Then Warden Powder said "Mike grab the lube and pour some more on the top of my cock right by the bitch's asshole."
I felt more pour out and it was now dripping off me and then Daddy gave one more push and POP the THICK head of his cock entered me to take my asshole's virginity. He stayed still as I tensed up from the shock of being so full even though it was just the tip of his cock inside me.
"It's ok boi relax." he said to me.
I felt the pain slowly go away then he pushed a bit more into me. I again grimaced and held my breath from the new feelings of pain and pleasure from having a thick cock stretching out my virgin asshole. He started to rub my aching balls, this calmed me down and again the pain faded into total pleasure! He stayed there like that for a few seconds then started to pull out a bit and go back in. I was starting to really like how this was feeling. Warden Powder looked down at me as I laid on the table feet in the stirrups totally at his mercy to do as he pleased.
He said "I have about 3 inches in you and I am going to go in more now boi."
I looked up and shook my head OK.
He looked at me "What did I tell you before about headshakes boi??"
Knowing he wanted to hear me ask for more of his cock I said "Thank you for going slow Daddy but please give me more of your BIG BLACK COCK!"