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Sex With The Boss

by Obie


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 be my boss from my full time job. He is a very good looking man and I have always wanted to see what he had in his pants. He asked me if I wanted to be his caddie and of course I said yes. While we were playing, he would rub his dick and play with it through his shorts and he always made sure that I saw him doing this. I started to get really turned on by this and decided to start doing it back. After he finished his round. His partner that was playing with him gave me a tip and said that he would see me later. However, my boss was nowhere to be found. It pissed me off because he did not even say goodbye. Anyway, I went to the locker room to get a shower and change. As I was standing at my locker with nothing but towel over my shoulders, I heard,"What a nice ass you have". I turned around to see my boss standing there. "And a nice putter you have also." I said thanks as he walked over to me. He sat on the bench and asked if he could get a closer look at my putter. Of course I said yes. He reached out and held it in his hands and started to rub it up and down the shaft. He then leaned over and took in all the way down his throat. After sucking me for about five minutes, I blew my wad down his throat, which he eagerly swallowed. It was the best blow job I had ever had. He stood up and gave me a kiss and handed me a piece of paper and walked away. The paper had written on it, "My office Monday at 11:00 a.m." Monday finally got here and I was anxious for 11:00 to get here. At about 10:30, my boss came in for the day in his sweats and tee shirt. At 11:00, I went to his office and the secretary let me in. Once I was in his office, I noticed that he wasn't there. So I started to look around. I then heard a door open and there he was, coming out of the bathroom freshly showered with nothing but a towel over his head, drying his hair. This was the first time that I had ever seen him naked. He was nicely built and had a good 8.5" cut dick. "Nice putter you have also." I said. He told me to sit down on the couch and walked over and locked the door to his office and told to secretary to hold all calls. He then walked over and leaned against the desk. As he was walking around the room, he was getting a hard on and so was I watching him. He told me that he wanted to see if I could give him and "driving" lessons. He walked over and got down on his knees in front of me and started to unzip my pants. On this day, I wasn't wearing and underwear and my dick jumped out with the hopes of fucking the boss. He then leaned over and took me dick in his mouth messaging it with his throat. He pulled off of my dick, stood me up, and started to undress me. Once I was naked, He walked me over to his desk. He turned around and laid down on his desk and said, "Give me some hard driving lessons." I leaned down and took his dick in mouth. I sucked on him for about five minutes and then sucked on his love hole for a couple. I then placed the head of my dick to his ass and slowly pushed it in. Letting him get used to me for a minute, I started to pound his ass like he wanted. He reached out and grabbed his dick and started to beat off. He suddenly blew his wad over his chest. Seeing this sent me over the edge, and I filled his ass with my cum. After cumming, I stayed in his ass for a few minutes. He invited me into the shower to get cleaned up, where we got dirtier instea--with him fucking my ass.

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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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