I was only 14 years old at this time. My grampa asked me if I wanted to do a painting job on a house with a friend of his. He was in need of a helper.
I knew the man for quite a while but I didn't realise he wanted more than just a helper.
I jumped to the offer because my mom and sisters did without money for quite a while being on welfare since my dad left us when I was just 5 years old.
This was going to be my first time of making any real money.
Bill was his name. He picked me up at 7 am and took mme to the house in the east end of Vancouver.
We took a few tins of paint and rollers into this old 3 story house on 12th ave. He introduced me to the old woman that owned the house.
Then we proceeded to move furnature around and cover other stuff with tarps.
It was now noon time. The old woman said she had fixed us a lunch at the table and she was going to lye down for a while.
Bill and I sat at the table corner and proceeded to dine.
Bill started off the talk with my family and knowing that we needed the money to servive. And stated that he knew I was able and ready for work. He also asked if I had a girl friend yet. I awnsered no not yet.
Then he took his right hand and rubbed it up and down my left leg and thigh. He said, Well it won't be too long, your a good looking boy and you should know what to do with a girl when you get one. I just sat there kinda playing dumb and nodded assent.
He continued to rub my thigh and talk about the good things a guy can do with a girl. Then he told me that his wife was going through problems and she wasn't able to give him any sex for a long time now.
I kind of knew where that was heading but I kept silent and just nodded again. I could see that Bill had his other hand under the table and there was movement coming from it.
Bill then went a little higher with his right hand and was rubbing against my cock of wich was starting to get erect. This was a situation that I could not get out of. He was offering me money for the work and I couldn't turn it down.
He then started to rub my cock and tell me how good it felt and looked. He kept saying that it was OK to touch other peoples body parts as long as both people are accepting of it.
I got to admit, it was feeling good.
He then pulled at the zipper in my pants and pulled it down over the tight little mass that was swelling up.
Bill then took my left hand and pulled it under the table to his open pants. There was a cock sticking out of his pants and it was very swollen.
He was moving my hand up and down over his cock and doing the same to mine. He had mine out of the pants and standing erect with his hand stroking it ever so slowly.
Well he stated, lets clear the table and see what we can do.
We cleared the table of dishes to the kitchen and placed them in the sink.
He then turned to me and led me to a big chair in the kitchen.
Bill started rubbing my cock again until it was swollen again and started to ache.
He then told me to get up on the chair with my pants down. I then got up on the big chair with my pants down to my ankles, this left me wide open at my rear end. he reached around me and stroked my cock until it was hard again and still aching. Then he started playing with my ass cheeks, rubbing them ever so softly and working his way toward my ass hole. He reached into his pocked and pulled out this little container, took the top off and dipped his finger into it so as to put it on his finger. Then he started to rub this stuff around my ass hole slipping the tip of his finger in to the hole slightly. Still slow stroking my hard cock. I could feel him now pulling at his own cock and trying to direct it to my ass hole. All the while telling me of stories of him and girls and what to expect when I run into this situation. I just kept nodding and saying yes.
He said that my hole was a bit bigger than he thought it would be. He also asked if I had had anything up my ass in the past.
Only my finger when masterbating I said. Little does he know that I have had a lot up my ass. From my finger to tooth brushes and even my mom's douch. And it all felt good while masterbating.
I just kept thinking, put it in, I can feel it against my ass hole, just push it in. Just as I thought that I heard him grunt and he came all over my ass cheeks and he was stroking me faster at that time and I exploded into his hand. He closed his big hand around the end of my cock and caught most of the cum as he was still stroking.
He then walked over to the sink and cleaned himself up and turned to wipe my parts off with a cloth. Both of us now cleaned up and went back to work. All the time he was assuring me that maybe we could do that again. I was thinking, ya if you can put it in before cumming.

Later, there was a knock at the door. I went to awnser it. It was just a delivery guy with something for the old woman. I was standing there talking with him, the door was just a jamb open. Bill had come up behind me and was pushing the front of him into my back side. I then closed the door. Bill then put his hands around my waist and was pushing his hard on into my crack of my pants. He bent down and started to kiss me. I turned away and said please not that. He understood but kept pushing his now bulging member at the back of my pants.
I said to him that the old lady could come down at any time.
He said Ya that's right then led me to the basement stairs. Lets go down there, I have stuff to show you that we have to do in the basement anyway.
Sure enough we arrived into a make shift bedroom. He said that he had already cum at the front door and that I should have a turn.
I just thought, about time. He laid down on the bed with his pants down and bum in the air. He said just put a little spit into my hole and put yourself in. That was great. I was in such a hurry I couldn't use much spit so I was pushing my now throbbing member up to his ass hole. It popped in. I started moving it in fast. He colapsed on the bed and said to take it easy. I slowed a bit but kept pushing. I was able to get all 5 and a half inches in in no time at all. I was moving faster as feelings started to tingle in my cock and body. This felt great, I said to myself. I came very fast but still kept moving in and out so as not to let him know. I just could not pull out, it felt so good. I pushed in and out until I was biult up for another explosion of cum. I was moving smooth and fast and could hear him grunitng under the pressure, but I didn't care I just wanted to cum again. As I was finally spent I pulled out reluctantly and slowly. That was the first time I had ever cum in someone and especially an older man. I didn't expect this to be my first sexual experience.
We cleaned ourselves up and went back to work.
He drove me home after our day was done. Bill asked if I wanted to come over to his place this weekend. He said his wife was going out of town.
I said yes that sounds great but I knew that I wasn't going to do it. I wasn't sure at that age wether I wanted that type of sex with another man.
So, Yes I quit working with him and found another job out at my aunt and uncles place with no sexual advances.
I still think about it. Maybe I shoul have, I did miss it and had that feeling for a long time. OH Well.