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True Stories: My First Boss 
 34 votes
Author: Arthur  Published: 12/4/2007  story views: 3508


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I was hired for my first job at the age of 18, fresh out of high school. I was a virgin when it came to men, but not girls. I had a girlfriend, but felt this attraction to members of the same sex.

My first job was at a restaurant in a small town. I was one of the waiters. The only waiter - the rest were waitresses. My boss James was very good-looking, athletic, and all the waitresses gushed about him. After 3 months of working at the restaurant, I found another job and one night after the restaurant closed I told James I was quitting. We talked and shared a few beers and talked for a long time after the place had closed. The conversation turned to girlfriends and sex, and he told me of some of his past sexual encounters before he became married. He went into explicit details. I became aroused as he relived these past encounters, especially the ones he told about how his girlfriends would give him head; and in the same breath told me his wife wasn't into oral sex, and how much he missed blowjobs. I glanced at his crotch a few times during his story telling, and I could see the outline of his hardening cock. He noticed me looking at his bulging crotch and we both fell silent. It was a bit nerve racking. He finally grabbed my hand and put it on his crotch. That was all it took. I was rubbing my first cock through a pair of slacks, my own dick as totally hard.

Soon I had his hard cock in my hand, stroking it. It looked and felt huge, but in actuality it was about the same size as my own. I heard him say, 'suck it', and before long I had a cock in my mouth. I loved it. The way it felt and tasted. I must have been doing a good job because he was moaning and urging me on, telling me to take it all. I took it as deep as I could and felt his pubic hair against my nose and lips. He held my head with his hands and I sucked him. He said, or rather moaned that he was going to cum. I continued to suck him and he held my head firm as he shot his load in my mouth. I swallowed what I could, choking; but I really enjoyed it.

From that night on, I knew that I was a cocksucker. So at 18 years of age, I sucked my first cock, swallowed my first load; of my 40 plus year old boss.
 
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