This is a fantasy that popped into my head whilst at work today. Now it’s there it is something that I think I would really want to happen.
I have been working on a property for a good few weeks now up and down Scaffolding and doing various jobs.
The owner of the property came up to me one afternoon and asked if I would be willing to do a few small jobs around the house at the weekend so that the property would be ready to be lived in.
I agreed that this would be ok and was given a list of small tasks to do.
The Saturday arrived and I decided that as I didn't really have that much to do and was indoors for the most part I would go commando - Not something I do very often when wearing Work Trousers.
I popped out on the scaffolding to grab something and thought that I felt something snag one of the threads on the crotch of my trousers, I felt behind but could not feel anything so carried on.
One of the tasks I had was to change a few light fittings in the Bedroom and the only pair of steps around were really on their last legs and ready to break. At this point the owner was at home so I asked if he could possibly foot the ladder for me so that I would not risk falling off. He agreed and I set about the task.
Little did I know that there was indeed a small hole in the crotch of the trousers, and when I climbed the ladder I must have given the customer a bit of a view as when I looked down he was looking a little bit uncomfortable with a slightly redden face.
That light fitting was changed so down the ladder I came.
The customer when out of the room to put the kettle on (Or so I thought) and when I bent over to pick the next fitting up and get it prepared, I felt the crotch of the trouser split a little more and that is when I first realised there was a hole, At that point I started to feel a tingle in my groin understanding now why the customer was a bit red faced.
Feeling that little bit horny, I decided that I would test and see how far it would go, worst case he tells me I have a hole and I would have to go to the store and get some more, best case some fun.
The Customer came back into the room with a brew which was a bit too hot to drink straight away, so up the ladder I went again.
To my excitement when I was reaching up with the light fitting, I felt a finger poking me through the hole in my trousers.
Looked down and saw the customer with a smile on his face, I Smiled back.
With that he pulled his finger out and said you do realise that you have a hole there, to which my reply was 'There is actually 2' with a devilish grin.
That is when things started to get really exciting, whilst keeping eye contact with me he put his finger to his mouth made wet and it was then put it back in the hole and started to feel around for the other hole, which felt amazing.
I felt him gently find my hole and draw small circles with his dampen finger, I pushed against it and inside it slips. I then responded with 'I think you found it' I looked down and could see that the front of his Shorts were starting to look a lot fuller.
I got down off of the steps and got on my knees pulled his shorts down and to my excitement there springing to life was a nice 8” uncut cock after staring at it for a while I licked my lips and then up and down the shaft, I then put it in my mouth and started to suck it.
After a couple of minutes of sucking he grabbed me by the shoulders spins me round and pushes me over the edge of the bed with my arse in the air, I then again felt him probing at my hole, I guess he wanted a bit more room thou, as he grab both sides and ripped my trousers to make the hole bigger...
He then went back to working on my arse, I felt some cold liquid applied to the crack of my arse first one finger, then two, then three he played around with my arse for a while then pulls out,
I asked what the liquid was and he said that when he saw the hole in my trousers and the fact I was commando he picked up the bottle of lube from his car whilst he was making the tea.. He said that he wasn't sure whether to do anything or not till he saw the hole was bigger.
I stayed in that position unsure as to what was going to happen next - I knew I wanted to be fuck by that lovely cock.
I felt more lube being applied to my hole, I was expecting his cock to be the next thing I felt but it wasn’t. 3 Fingers again enter me and probe me for a while. Which feels amazing. Soon I feel a bit more stretched as the 4 Finger enters inside me. He could sense from me pushing back that I was enjoying this and in goes the thumb. Now I am really feeling my hole stretch but know that I want his fist in me.
After a while his fist goes in (First time ever having a real fist in there) The precum is dripping on the front of the trousers I am still wearing and can feel my cock straining for release.
After what feels like 30mins (Probably more like 5) he pulls his fist out of me flips me over and takes off my trousers.
I think he may have been happy with what he saw as when he did, he was straight down on his knees and sucking the Pre Cum off of the tip.
I could feel that it wasn't going to be long before I came so I told him to stop, and that I felt empty and needed his cock inside of me.
To which he grabs my ankles flips them by my head and lines his cock up to my hole.
As I had just been fisted it entered with ease and OMG it felt amazing, I could feel every stroke he made rubbing against my prostate, It was as if it was design to hit the right spot.
After a couple of minutes of this I could feel that I was about to Cum and told him so. He started then to pound me harder and harder, with a further minute I was releasing a load all on to my belly and screaming in ecstasy. I looked up at him and saw him closing his eyes as he pushed in Hard and stayed there, not sure how many ropes he shot inside of me but once he pulled out, I could feel it all running down the crack of my arse.
I laid in bed to recover for at least an hour when I said that I had better finish up for the day.
Thats when it hit me that I did not have any other trousers to wear and told the customer so - To which his reply was you can do the rest with nothing on and then he would lend me a pair. To which I Happily obliged.
I didn't get much done for the rest of the day and when It came time to go home, I thought that I would just wear the trousers with the hole in and maybe stop at the local cruising area to see if anything else might happen.
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