Saturday morning, after a solid sleep, i woke with a start. The first thought that came into my head was butt plugs.
Today was the day that i would have to start stretching my hole. The prospect scared me, here i was almost 50 and could count the number of time i'd been fucked on the fingers of both hands, and most of those were in my twenties. but Boss wanted me to loosen up, it was time to bite the bullet.
I got out of bed, and started to think how i was going to do this. The largest of the three was so big that i couldn't even get it comfortably in my mouth, there was no way that I'd get it in my arse ever. Thank god Boss was kind enough to allow me to start with a more manageable one.
Before i could think of anything else a text message came through.
"Is it in yet Tommy Boy? Proof will be required.
I tentatively put it near my hole and tried to push, quickly realising that going in dry was not going to work, unless wanted to damage myself before i even started. Thankfully i had over the years accumulated a good collection of lube sachets, far too many for someone with my track record. I tore open one sachet and smother the shaft of the plug , the closest I'd got to wanking in weeks , i slid the plug back and fore along the whole transferring some lube to my arse, and gently pushed in a finger to make sure that there was at least a minimal coating inside.
Deep breaths, ` push, i felt the pressure against the tight hole as the plug worked its way in, my cheeks widening and my hole happily welcoming the intrusion, then the slight pain kicked in, I started to feel uncomfortable, so gently started to slide it out, before repeating the process, slowly in, slowly out, each time going in a bit deeper, and a bit longer.
Another text.
I haven't got all day Tommy Boy. Photo in 5.
I lay on my back , legs wide apart and pointed my camera phone towards my arse. That should be ok for Him, i hoped.
Sorry for the delay Sir, and sent the photo.
"Good Job Tommy Boy. I hope you've had a shit, I want that in for the next two hours." "Two hours i thought to myself. I have to get some shopping done"
"By the way don't think that gives you an excuse to sit round the house for 3 hours. Get dressed, and go shopping, You will walk, get a coffee, walk around every aisle slowly, join the longest queue , when you have finished go and get another coffee, eat some cake, and then send a photo from the bathroom. Then walk home and send another photo. I hope you have had a shit because that plug is staying in now until you get home"
That in itself made me want to go to the toilet. But orders are orders. It had been years since i last had a buttplug inside me, and then it was for no more than five minutes. Was i capable of keeping it in for even thirty minutes let alone two hours, what if it slipped out. I rummaged through my drawers and found a pair of compression pants, i put them on in the hope that they even if it slipped out the butt plug would not fall on pavement or worse still on the floor of the supermarket.
I then headed out, my walk must have looked ridiculous, i was clenching my buttocks trying to ensure that the plug remained in place, when I finally arrived at the coffee shop i quickly visited the bathroom to check, gently pushing it in further. The need to pee was quite strong at this stage but I feared that just sitting down would result in my butt cheeks relaxing too much. I was going to have to shop on a full bladder. Boss's control on me was getting firmer.
I downed the coffee, and headed to the supermarket, my usual regime was to buy what i needed and get out, this time i walked slowly along every aisle, stopping occasionally to clench, willing the plug to stay in place. Finally i found the longest queue, two families, with what looked like a month's worth of junk food. I soon realised that standing still was more agonising than walking. I willed the queue to get faster, all that made it bearable was the presence of two bearded Daddy types in the checkouts either side. One of them caught my eye and smiled, I returned the smile and then started to put my shopping on the conveyor belt. Shopping over I seriously wanted to go back home but Boss had insisted i had a coffee, and to end him some photographic evidence of my plugged state,
I arrived at the coffee shop, and was followed in by one of the Daddy types, i ordered a coffee, when he whispered to me, don't forget Darren said you need to have cake as well, i turned round in shock,
Order a cake, and while you are at it mine's a Cappuccino and a croissant. I'll be sat over there. I placed the order, and went and sat down. Daddy was a handsome chap, salt and pepper hair and a close cut beard, unlike Boss, he wasn't physically intimidating by still had a presence We looked at each other in silence, waiting for the coffee and cake to be delivered.
It arrived.
We sat in silence, him drinking his coffee, me eating my cake he suddenly took a photo.
" Evidence of obedience. "
The silence again. I finished my cake. Getting unnerved by this man staring at me intently.
Finally
"Paul" he said introducing himself "One of Darren's enforcers, he like to have help making sure his slaves are obeying orders . I've not seen anyone shop so slowly, You did well. Time to send him a picture of that butt plug. Darren thought it would be a good idea if I came along to take the photo, it will probably be easier that getting you all contorted in the toilet, and also he wants proof that it's actually in.
The coffee shop was empty, just us and the barista, Paul went up to the counter, spoke to the barista, who looked at me smirked, and then nodded to Paul.
Follow me boy.
I got up and followed Paul to the bathroom.
As soon as I entered, he turned me round towards the wall and stared to forcefully feel my butt. He reached round and undid my belt my trousers fell top the floor , next he tugged down my compression pants.
"Clench " he ordered as he massaged mu butt cheeks pulling them apart, i tried my best to keep the plug in.
"Look as if it's pretty comfortable in there"
"Photo time. Lean forward and pull those cheeks apart"
"Ok, photo"
Now time for me to have some fun. He reached for the plug and gently withdrew it.
He turned me round , the plug was right in my face
"Look as is if its got a bit dry up there, needs some lube I think. Open wide"
I just stood there.
"I said open wide"he punched me in the gut as I gasped for air he inserted the plug into my mouth. "Get it wet boy" He started to slowly pull it out out before pushing it back in. "Deep throat that plug boy" He finally stopped, forcing it back in for one final time.
Another photo for Darren I think , an extra special treat, just to show how much you have enjoyed His gift.
Ok, that wet enough, back it goes. He again turned me round pushed me over shoved the plug back in.
"Ok. Get those trousers back on and head home"
In normal circumstances I'd have taken the bus, but i knew now that disobeying an order would get me in trouble. It was an agonising walk, but finally got to the flat. I unpacked my shopping and took one final photo. I realised that Boss had certainly done me a favour by getting Paul involved earlier. The only way i could comfortably do it was to lie on the flood and aim the phone camera at my hole.
I sent Boss the picture and waited. The two hours had gone some thirty minutes ago, could i now take it out, i thought it would be best to wait for an instruction.
Finally twenty minutes later, a text.
"Well done Tommy Boy, take it out, and have a rest. I'll be in touch later"
The last three hours had been agony, but now that the plug as I yearned to be filled again