This is the story of my first real gay experience, I had fooled around with boys my own age, albeit none of us knew what we were doing and had never gotten to "completion", but I knew at an early age that I was attracted to both men and women. In fact I was very attracted to the dad of one of my closest friends from school. Don was in his 40s while I was still in middle school and was 14 when this happened, over summer break.
I would spend the night at my friends place regularly, 2 or 3 times a week and he would do the same. One night I was over and had woken up just after midnight and had gone downstairs to get a drink, adjacent to the kitchen Don had his library/tv room. When I walked into the kitchen I heard noises coming from the room and saw the tv was on, the door was slightly open and I looked inside. Don was watching porn, being 14 I got very excited and quietly watched, after a minute or two I realized that Don was masterbating and was completely naked. I was just amazed, he kept jerking off until he came all over his stomach, at which point I stepped back a little and made a noise, he asked who it was as I quickly went back upstairs. The next time I spent the night, I was nervous and excited, I went back and this time the door was locked. Yet if I stood close I could hear sex noises coming from the room. Eventually it stopped but before I could leave the door open and his wife walked out and I made an excuse of wanting a drink as I quickly went back upstairs. The next week I avoided going over there afraid they were going to say something. But nothing was said. So, eventually I started go over again and I would sneak downstairs and watch him jerk off. Then one time I was there the video he was watching was of 2 guys and a girl except the guys also had sex with each other.
The next weekend I came over, and when I got there Don said that his wife was running late and her and the kids would be home soon. So, I stayed. I hung out with Don and after a while he said that he was going to see why they weren't home yet and went and made a call. I walked in as he was hanging up and told me they had car trouble and were staying at her sisters and he offered to take me home. He said it was okay if I stayed and I happily agreed. I went to bed and as usual, snuck downstairs to watch. He was watching one of videos and was slowly stroking his cock when he said my name and turned to look at me, he said that I was welcome to come in and watch with him. So I sat down and sat quietly and after a few minutes he said that if I wanted to get undressed and jerk off too he was okay with it. I got undressed and he put in a new video, it was of an older guy with a younger guy. We sat there and stroked our cocks slowly and he began to ask if I liked the video, I said yes, and he suggested that we try what they were doing in the video. He kissed me and placed my hand on his cock and as he kissed my kneck he pushed my head down to his cock and told me to suck it like the video. I did the best I could and after several minutes he blew a load in my mouth as he held my head and told me to swallow it all. Afterwards we sat and talked and he told me that he knew I was watching all along. As we talked he told me to suck it again until it was hard and then he said that he was going to fuck me. So, I licked and sucked his cock until it was hard, he then told me to bend over the small sofa we were sitting on. I did as I was told and he lubed my ass with his fingers and then pressed his, (to 14 yr old me), huge cock to my asshole. Then slowly working it into me, it hurt, but I was so excited I didn't want to stop. Eventually he was all the way in and began to fuck me, slowly at first then faster and faster. I began moaning and I told him to do it more. When he blew his load up my ass I came without much more than me touching myself for a moment. We went to bed and when I woke up he was lubing my ass again and told me to get on all fours and he fucked me again, this time we fucked for over an hour and he filled my ass up again. He later told me that his wife and kids weren't going to be back until Monday morning. So, I stayed all weekend getting fucked and sucking his cock over and over. Over the next couple of years I would stop by his house on my way home from school, go into his workshop, and drop to my knees and would suck him dry. He put in a lounge chair and sometimes he would fuck me, teaching me to ride his cock, and many other things. When his family was out of town I would come over and stay. Eventually we stopped for whatever reason, but about ten years later I ran into him at a bar near his home and ended up with his cock in my mouth again.

Comments

Anonymous

by Anonymous on Feb 2, 2016 at 6:43 AM

What a wonderful introduction to sex for you, My own first experience with a man was similar in some ways, It was when I was 14 too, There was a man who lived nearby and he would often speak to me when he was working on his car or garden on my way to and from school, He was in his late forties and quite (I thought) good looking, Over the weeks I started to flirt unconsciously with him until one hot summer afternoon he asked me in for a cold drink, I went into his kitchen and as he handed me a drink he put his hand on my thigh saying that he knew I liked him and there in that kitchen I was kissed for the first time and was soon naked as he undressed me his beautiful cock mesmerised me I wanted him so much that I did everything he asked sucking him as I sat on the kitchen chair I was lost and sucked him as best I could, Suffice to say he took my virginity as I was bent over the kitchen table I loved every second of it after the slight initial pain, Over the years he taught me a lot about sex with other men and I admit I even fell in love with him and to this day I much prefer much older men.

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Anonymous

by Anonymous on Feb 2, 2016 at 1:57 PM

Most of my friends who are gay/bi had their first successful or enjoyable encounter with older men. Don eventually even shared me with a few of his friends. Those were some of the best sexual experiences of my life. Now I am the older man, but I don't enjoy it as much as when the roles were reversed. Nothing like being the center of attention, and a room full of older men lusting after you.

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Anonymous

by Anonymous on Feb 13, 2016 at 3:22 PM

Thank you for sharing your amazing and erotic introduction to man sex. You had my cock throbbing.. and it still is. I was 14 and the man was my 22 year old male cousin.

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Anonymous

by Anonymous on Feb 13, 2016 at 11:25 PM

I had relationships with 3 older men regularly in my teen years. Don(44) from age 14-16, Russell(25) at 16-17, and Robert(32) from ages 17-20. My favorite was Don, he taught me a lot. Robert was awesome too, he treated me like a slut, his slut, and I loved it.

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