Our Milkman

Posted by: Age: 37 Posted on: 0 comments
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I wish I had more courage and understanding back then....

 

The first time it happened, I was about 17 years old, and a freshman in college. This is actually not one incident but a series of incidents with our milkman (the one who used to come to our house to milk our cows), who for some reason remained single, into his mid thirties. Since I had known him from when I was much younger, our encounters were always playful, mocking each other. On this day, I was sleeping in the open, upstairs, like I used to do sometimes during summers. I was sleeping, turned to one side, when I felt our milkman sit next to me, lean on me, and started reading the newspaper. He had just finished milking our cows. I felt him place one hand of his on my thigh - it felt very nice. Honestly, up until that moment, I had never had any erotic thoughts involving him, although I had heard of other people's male-male encounters when I was in the high school dorm. His palm was still on my thigh, and for some reason, I turned face down, rather slowly, so that his hand wouldn't slip of my body. All this while, he was still reading the newspaper, and I was pretending to be asleep... Once I was lying face down, I felt his palm on the back of my thighs - his wrist resting comfortably between my buttocks. He pressed his hand gently - I suppose neither of us had the courage to make it obvious - at least, not yet... After a few minutes, I picked up courage, and turned to one side, again - back to my 'original' position - his palm was back on the side of my thigh, but it started slipping down towards my dick. His palm gently cupped my dick. Now it was pretty obvious we were enjoying it, but still did not have the courage to do it openly. His hand gently massaged my dick, but only through my pajamas... After several minutes, I pretended like I 'woke up' - I was a little embarrassed to face him - because I was not gay - though I thoroughly enjoyed the sensation that another man's hand gave me. For some reason, I felt that I had behaved like a woman! However, after I went back to college after vacation, I thought about it - and regretted not letting him go all the way. I had to wait for a long time before I got a few more opportunities - just a few - when I let him touch me 'playfully'. Though our milkman was almost part of our family, and though he was kind of testing my limits, he did not have the courage to push it too far... One day, though, I went upstairs, hoping that he would join me there. And he did, a few minutes later. This time, I let him take out my dick from inside my pajamas - he did a nice job until I came, though I pulled off from his hands just before I came, so as not to dirty his hands...

A few years later, (after I graduated from college), when I was about to take up a job in a far off place, I knew that I would not get to see him - so, as a parting gift to him, I let him do me from the back - only on the surface of my buttocks, with my clothes on ... until he came. He probably used some cloth - because my pants were not messed up even after he came. I often wondered if he was gay - or may be just that he did not get a woman...? Years later, I often think about him... and also about my own hang-ups back then.... Because, I knew I was not gay, but still I enjoyed these sensations...I deeply regret even to this day that I did not do it more often with him... I even feel guilty, because our milkman is so nice - and it seems that I wouldn't have lost anything by letting him touch me more often, since I was seeing him only during my vacations, anyway...

- Natureseeker

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