The walk back to the office was agonising. Boss had made it clear that i had failed to follow an order. He walked at a fast pace, that made judging the required two steps behind him difficult to judge, hopefully i succeed to obeying this command, but dreaded the punishment in store.
We arrived back at the office, i opened the door, allowing Boss to enter first then followed, and knelt. Waiting to hear my fate. Boss wheeled his chair into the middle of the office, sat down and ...
Silence.
He stared at me intently, i could sense his disappointment.
"Here Tommy Boy, over my knee"
"Crawling over towards him, i stood and lay across his muscular legs. He started to firmly massage my butt, working his way round both cheeks, it felt almost as if he was trying to work through the fabric into my butthole.
Then a whack
"Not a sound Tommy Boy"
Then a second, a third, by the sixth my arse was on fire. I wanted to scream, but knew that would result in further punishment. Another seven whacks followed,and i found myself on the floor, Boss hand pushed me off his knees. Tears were streaming down my face as i sobbed silently
Before i could work out what to do next, .
"Here" He said holding out a hand, i took it and He helped me up.
"Drop your trousers"
Doing as i was told, i fumbled as i tried to undo my belt. He lifted my head and using His thumbs dried the tears from my eyes"
"Now Tommy Boy, you will get used to that. I've decided 13 spanks at the end of the working day is what is needed. You have a great arse, just calling out to be smacked, and your gym sessions are going to make it even better to play with."
He then removed His hands from my face, and went towards the cage, and started to laugh.
"It can't have been that bad, you've got a lot of cum down there He said.
He brought a thumb towards my mouth. It was covered in my spunk , having not wanked since I first put the cage on, even before i met Master M, there was a fair amount
"Swallow Tommy Boy" He said feeding me my own cum. He then swallowed some Himself. "Tasty" he said laughing.
He then bent down placed his mouth over the cage and slurped, returning to my mouth He filled it with the evidence that i had enjoyed the experience.
Put those trousers back on, and sit,
"Thank You Sir I "said
The rest of the afternoon, went slowly and was almost like an ordinary work day, save for the ritual of having to ask Boss for permission to do things.
5.30 eventually came.
Time for me to head off Tommy Boy. Sit there for another twenty minutes before you head home. See you tomorrow. I `ll have more instructions on your behaviour, you will be a perfect slave by the time I've finished with you.
That night my sleep was full of dreams, involving cigars, boots and piss, i woke at 2 am and my dick was so hard i felt as if the cage would split.
The next morning i arrived in the office at 8, there was thirty minutes to go, but i was there on my knees waiting.
My eyes looking down at the floor, i saw a pair of Black highliner Wescos appear. My heart skipped a beat before i bent and kissed each one.
After pulling out Boss's chair and i asked for the morning's orders i secretly hoped it would involve some boot worship.
Get on and answer your emails, after yesterday you need to prove your worth to me. I crawled to my desk.
"Sir may i please sit Sir'
"Yes, Tommy Boy"
Sitting i noticed that my desk and chair were different.
" you look puzzled Tommy Boy, i asked maintenance to alter your desk, its a foot lower, as is your chair - and that can't be adjusted. I decided that you need to sit as if you are always looking up at Me."
"Thank You Sir"
It was a busy day , bith Boss and I had some urgent tasks that needed to be dealt with, so busy i failed to realise it was coffee time.
"I'm Thirtsy"
"Sorry Sir?"
"Thirsty, i notice that you haven't asked for permission to get Me a coffee. I want one on my desk in 13 minutes."
"Sorry Sir. Sir May I please get You a coffee Sir?" "Yes , 12 minutes"
I ran to the coffee bar, thankfully no queue, i realised in time that i had only received permission to get Boss a coffee, not one for myself. No coffee for me this morning i said to myself. I returned to the office. Boss was there looking at his watch.
"Another twenty seconds and you would have failed. No coffee for you i see, sometimes you are good at obeying orders."
"Ok new order. No more work time coffee for you, not even at meetings. It's going to be be piss or nothing. Either from your sports bottle or when sat here from this. "
Opening a drawer he took out bright blue adult sized sippy cup. He handed it over. I started to make a move to take it when i remembered.
"Sir may I please take Your gift from You Sir"
"Of course Tommy Boy. I've even filled it up for you, quite fresh too"
I lifted the cup,took a sip, smiled. "Thank You Sir"
At 12.30 Boss looked across at me, Tommy Boy, I'm going out for lunch, you can sit here until I'm back. Here's something for you to eat on whilst I'm out. He walked over and placed three farley's rusks on my desk. Something which I'd not had since a baby.
Goes well with piss, apparently he said when walking out of the office closing the door behind him.
Ninety minutes later i was starving, Boss was still out, and my mouth was still trying to adjust to the taste that the mix of baby food and piss produced.
Suddenly my phone went with a test message
"Tommy Boy I'll be back in 5 minutes"
I rushed to my greeting position, when the door opened and those boots appeared and could have wept with joy. I bent down and gave each one a passionate kiss.
"Miss Me Tommy Boy" "In which case i think it's time you showed me how much you do. " Boss sat down in his chair, out His feet on the desk.
I have a conference call, the treads on these have been neglected show them some TLC.
The next hour was spent slowly licking through the treads on each foot, loosening and swallowing bits of grime. I'd occasionally stop the licking and rub the sole into my face. I could feel a layer or two of skin being removed, as the dirt transferred itself from Boss's boot on my face. All this time Boss didn't utter a single word to me, but carried on with his conference call.
"Cheers speak soon"
"Ok Tommy Boy - back to your desk. You did a good job, ninety minutes before Your punishment"
I returned to my desk to work, waiting for the spanking . 4.30 came quickly.
Boss wheeled his chair to the middle of the room.
"Trousers down."
I stood there with my trousers at my ankles, only my underpants hiding my caged dick. Boss turned me round and and started to tug suddenly the pants were little more than a rag,
He stuffed it in my mouth - "Let's see if that stifles any screams"
"Down and over" he ordered. I laid over his legs, and waited for the spanking. Compared to the previous day's gentle introduction, this session was far more brutal. He started to violently explore My butt hole sticking in to fingers and twisting and turning, the pressure started to make my dick tingle. Then whack. As with the previous day each one burned, Would i ever get used to this. I suspected not.
When he finished he pulled me up, again tears were running down my face , but yesterdays gentle caring wiping away was not repeated. Instead the fingers he had used to explore my whole were forced down my mouth.
"Clean them Tommy Boy. And from today no more underwear. Jocks at the gym maybe but nothing else. Bring all that you own in tomorrow. They will have other uses. "