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The Bosses Caddy

by Obie


On the weekend, I work at a golf course to make some extra money. I have been there for two years and have done pretty good. However, this weekend I did extremely good. I was coming in from caddying around when I heard my name being called. I turned to see who was calling and it was my boss from my week day job. He asked if I wanted to caddy for him and his friend. I told him I would after I got a quick drink and use the bathroom. Out on the green, he asked my suggestions for club and how he needed to make the shots. On the seventeenth hole. He had to use the bathroom. He turned right to me, pulled out, and started to use the bathroom. When he was finished, he played with himself until he was hard. Then he put himself up and continued his round. Once back at the club house, his friend gave me a good tip, but my boss had left. I was pissed because I had worked for nothing. So I went to the showers and cleaned up. While I was standing at my locker with nothing but my towel over my shoulders, I heard nice ass. I turned around to see my boss looking at me. "nice putter you have also. Do you mind if I have a closer look?" Of course I told him no I didn't mind. He came over and sat in front of me. He took my dick in his hands and slowly started to rub me softly. Then in an instant, he engulfed me to the base. He sucked me like I had never been sucked before. In no time, I was shooting my load down his throat. He kept sucking me until I went soft. He stood up, gave me a kiss, and gave me a piece of paper. Then he said thanks and walked away. I opened up the paper and it said, "Be in my office Monday morning at 11:00." It also had a $100 in it. Monday morning, I did not see him come into the office until about 10:30. At about 10:45, his secretary called me to his office. When I got to his office, he wasn’t in there. So I started to look around. He had a nice leather sofa which I sat on. Then a door opened and he was dripping wet from just having a shower. His towel was over his head as he dried his hair. "Nice putter you have there." He had a nice seven-incher that was growing harder by the second. He walked over to the desk and used to phone to tell the secretary to hold his calls. He leaned back on the desk still in the nude. By this time my own dick was getting hard as a rock. He said," I called you up here to see if you know how to use that putter like I think you can." He got up, walked over to me, got on his knees between my legs, and said that he would like to taste my putter before I used it on him. He reached up and unzipped my slacks. I wasn't wearing any underwear, so my hard on jumped right out. He slowly licked the head of my dick and then slowly took it all the way down his throat. after sucking me for just a minute. he stood up and told me to undress so that my clothes would not hinder me in fucking him. He lead me over to his desk where he climbed on top of it with his ass hole shining right at me and told me to fuck him good. I walked up and started to lick his hole telling him that I had to get it good and wet before I fucked him. Then I stood up and slowly put my dick in his ass. I held it just as I went in when he impelled himself with my dick. He started bucking on me like a cowboy on a bull. In no time I shot my load up his ass. I stood him up and traded places with him and within just a few humps, he was filling me with his load. When he was finished, he told me that we needed to get cleaned up. He led me to the shower where we washed and fucked each other for about an hour.

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6 Gay Erotic Stories from Obie

From Cycling to Sex

On the weekends, I enjoy going to an abandoned park on Lake West Point in Georgia. Here, I can ride my bike and enjoy the great outdoors. I very seldom see anyone else there. So on an occasion, I will stop, strip, and let the breeze blow over my body as I jack off. This weekend, I was getting to the spot where I enjoy myself and there was a truck parked there. I got mad because

My Co-worker Forever

I started a new job near the college that I was attending. Not only was I new to my job. I was new to the area as well. I knew no one. On my first day at the office I met Jacob. He was a very attractive man. He had a look about him that drove me crazy. He introduced himself and invited me out to lunch with him. During lunch, we talked about my coming to the area and job, and his

Sex With The Boss

On the weekends, I work a second job at a golf course as a caddie. I make pretty good money in tips. I also get to meet some interesting people. Some of the people I get to meet, end up being really good fucks. This last weekend turned out to be my best weekend ever. As I was coming in from my last round, I heard my name called out. I turned to see who it was and it turned out to

Summer Helper

When he walked in the office to put in his application for summer work, I knew that I wanted him to work for me. I talked with my boss and we agreed to hire Robert. He was one of those guys that isn't that handsome, but has something about him that made me fall for him from the start. He worked with me for about a week before he started to loosen up. On the day that he did, we

The Bosses Caddy

On the weekend, I work at a golf course to make some extra money. I have been there for two years and have done pretty good. However, this weekend I did extremely good. I was coming in from caddying around when I heard my name being called. I turned to see who was calling and it was my boss from my week day job. He asked if I wanted to caddy for him and his friend. I told him I

Trip To The Beach

Jake, Bob, Sam and I decided to got to the beach for the weekend and relive the old college days. Along the way, we picked up a friend of Sam's. His name was Todd. He was about 6'4" and built oh so nicely. He and I got to talking on the way to the beach. I found out that his home town was just down the road from mine. We knew several of the same people which really surprised me.

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