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What seemed like hours passed by, no message from Boss, i took the opportunity to clean the house and get my clothes ready for the week ahead, both at the gym and for work. Remembering His orders to only wear tight trousers in the office I went through and discarded those that were so loose that not even a hint of the cage's outline was visible. This left five pairs , one which was obscenely tight, whilst the other four whilst not as bad made sure that the casual observer would notice that it wasn't just dick underneath the fabric.
Then a message. It was 2pm.
Tommy boy you are to to spend the next ten minutes fucking yourself with the butt plug, then keep it in for five, then rest for five, then repeat, do so until you next get a message. Starting NOW.
Even though i had spent some two hours with the plug more or less firmly nuzzling in my arsehole earlier in the day, the fucking was a different sensation, Boss had not given me any instructions on how to fuck myself, so i took the decision to try different methods, first a few minutes of slowly pushing it in then retracting until only the tip was still in, and repeating the process, i quickly built up speed ensuring, that at no stage was the plug totally out of my arse. Next after slowly pushing it is, i with drew it quickly and completely, waiting for the hole to close and then pushing it back in , again building up speed as i went. After ten minutes pushing it in, and keeping it there came as a relief, the lips of my hole gently caressing when the base of the plug rested on my cheeks. Rest time, removing it resulting in a gentle pop as it exited my body. The five minutes dragged, i was itching to start the fucking process again, i decided that the rough entry exit method would be best for the start of the cycle, and kept it up until it was time to keep it in. After eighty minutes of alternating between fucking myself, keeping the plug in,a nd having an empty hole, my butt was tarting to feel tender, i decided to get some more lube when a message cam through.
That's enough for now. Be ready to repeat this at 6pm and 10 pm.
By 10pm by arse was now quite raw, and i honestly didn't know how i'd cope with another hour or more of forcing the plug in and out of my hole, but orders are orders, and as 11pm approached i realised that my hole was giving less resistance, it was slipping in my quicker and easier, as a result i got into a faster rhythm , in out in out in out.. When the time came for it to just remain in my arse, Boss sent me another message.
" That's it, send a photo of that hole of yours, and get some sleep"
The next morning i woke, my hands reaching back to my arse. I realised i had played with it more in the last 24 hours than I had with my dick in the last two months. I checked my phone. Messages.
"Good Morning Tommy Boy, good job yesterday, now time to try that second plug, I want you to go deeper and wider for Boss." " 10 am you keep it in for an hour, 12.30 fuck for thirty minutes, 1.30 in for 2 hours, 5 fuck for an hour , 7 in for an hour , 9 in for an hour Tomorrow fuck for ten minutes before heading for work.. I'll check up on you,on my arrival . Remember the tightest trousers, and i want you plugged. "
Thankfully Sunday was generally a day of just lounging around the flat, so i could probably manage this schedule. I went and retrieved the second plug, it was longer and thicker than yesterdays ,with ridges, it the first twenty minutes felt like i'd not had anything up my arse ever before, however eventually i soon got used to the invasion and by 11.05 i again had that empty feeling. This feeling of emptyness arose when ever my plug session finished be it full insertion or fucking, however by 9 everything ached and i was looking forward to the relief of being empty.
The next morning it was raining quite heavily , i had returned from the gym, showered and was about to get dressed when i remembered the plug. Boss had not specified which pug to use, i wanted to make him proud of me, and prove that i had obeyed his orders, should I try the third. I had not looked at it properly when i opened the parcel on Friday. On closer inspection i realised that it wasn't particularly longer than the second , but significantly wider, the main difference being that it was hollow,it would therefore if kept in place keep my hole open.
. Let's give it a shot. It too some effort but it went in. and by the time i put on my trousers they were so tight that there was no risk of it falling out. I also realised how lucky i was that it was raining, my long raincoat would hide the obscene bulge.
8.15, i arrived at work, got on my knees and waited.
8.30. A pair of police motor cycle boots came into my eyelin, i dutifully kissed each one restraining myself from worshipping every single centimetre of leather. Crawling to Boss's desk i could feel the blug keeping the hole open. I pulled out His chair, waited until he was seated, and got back on my knees.
"Sir, How can i serve You today Sir?"
"I think you know. Stand"
He put on a pair of tight leather gloves and started to feel my crotch, Good Tommy Boy, nice and tight. I want everyone to be aware that you are caged. Everyone. Turn round. Nice firm buttocks, but i knew that, now lets see how well you did . He gently undid my belt, and slowly pulled down my trousers, he guided me so that i was sent over my desk.
Wow Tommy Boy, I'm so proud of you , you went for the largest one, I think that deserves bring forward your afternoon punishment forward a few hours. Consider it a treat. Come on over my knees.
I complied, i felt the leather gloves move over my buttocks gently massaging, then i felt a finger enter my hole, unlike the first occasion he did this it had no impact on me, it was only when i had three fingers inside going deeper than i had ever experienced.
Like that Tommy Boy,
Yes Sir I groaned. It was a new experience and it was making my brain fly. Ok, I want you to countdown from 13.
Whack, 13 Sir, Thank You Sir Whack 12 Sir Thank You Sir Whack 11 Sir Thank You Sir ... Whack two Sir, thank You Sir Whack one Sir, Thank You Sir
`Tommy Boy, I'm going to have to start whacking harder at this rate, not even a grimace. Now let's have another feel that hole.'
He returned to exploring for five minutes, working his fingers around the circumference created by the plug.
Ok, get up, and take it cout, i dont want you being distracted by pleasure all day, come back and kneel on your return.
I ran to the bathroom.
Hello Thomas, said Robert, a colleague who had worked with me on previous projects. How's it going. Is Darren treating you well. He certainly looks as if he has you under control.
`Yes Rob" I replied "It's been a challenging few weeks, but working for Darren is going to be a great developmental opportunity"
"Good, I'm glad someone has taken you in hand" As he left he smacked my arse. "It's been a long time coming"
I removed the plug, and popped it in my jacket pocket, and returned to my desk. Back on my knees I waited for my orders. Boss was sat in his chair, rubbing his gloved hands together.
"Back then are we?, these need a good clean. Open, and worship."
I opened my mouth and he place his right hand in my mouth ,
"Get them clean T Boy, get your arse juices off of this fine leather"
He forced three fingers right down, encouraging me to gag slightly and produced some saliva. Removing the fingers he placed his palm over my mouth, his left hand forcing my head forward
"Good boy taste that leather, taste the cigar I had last night, taste your hard work from getting that loosening up that hole." As the saliva drooled out of mouth mouth His eyes looked directly into mine, a look of encouragement, i so badly wanted, my aim was to please Boss,the look was all i needed to know to prove that i was, eagerly licking his hand i mumbled "Thank You Sir, Thank You for taking control of me. "
"I've only just begun Tommy Boy" "Tommy Boy" he said throwing a pair of what were once my underpants at me ", I have another appointment at Charlie's office. You're coming with me, I'm sure Dave would love to see you again."
Wiping the drool off my chin, i nodded, "Yes Sir,
"Follow me, remember two steps behind, open doors."
"Yes Sir."
It was actually good to be out of the office, as i really enjoyed watching Boss walk, he had a very confident gaite, and i still wanted to be sat under his arase one day , it was so meaty as a result of his gym regime, i could see myself fighting for air as his whole placed itself firmy on my mouth ready to be worshipped.
"Tommy" Come on you stupid cunt, press the button we need to cross. "Sorry Boss" i pressed the button at the pedestrian crossing and again waited two steps behind him
We arrived at Charles office building. I opened the door for Darren, and followed him in. We got to the top floor, and Dave was outside the lift waiting for us.
"Hi Darren, Charlie's down there waiting" "Thanks Dave, - you remember Tommy don't you. Can I leave him here with you to entertain when I'm with Charlie." "Of course, I've been looking forward to it all day." He said giving me a leery grin.'
Tommy Boy don't disappoint me, behave now for Dave,
Darren walked down the corridor and without knocking walked into Charles's office.
I looked at Dave, he was not as scally looking as he was last time, his eyes were now far more focused,and his posture was that of someone who knew that he could be in charge given the opportunity, he was also far better dressed, more of an executive than an office dogsbody.
Ok Tommy follow me.
I followed, and he entered a spacious office and walked to the window, below one could see the city.
Great view , eh Dave!
He responded by punching me hard in the gut , and pushing me to the floor.
"David Sir, to you , not Dave, show some fucking respect. Darren will join us once he's finished with Charlie, you don't want him to come in in the middle of me punishing you do you ?"
NO David Sir?
Good, now let's get started, he started to undo his trousers and took out his dick,
Come on then, just do sit, or should I say kneel there.
He approached and placed one hand behind my head ...