My mentor at work turned into a mentor at play.
In my second real job after leaving college, I had a supervisor/mentor who was a very personable, friendly guy. He lived alone, and there were rumors he was gay, but he was also known to date women, even some from our company. He was a consultant really, and only came in every week or so. We worked closely, and I came to enjoy his company and look forward to it.
I also (this I realized later) would go back to my apartment and indulge in a long and hot session of masturbation, stripping my clothes off at the door after a day of working with him. Now and then he would make comments about masturbation, and I started to think that maybe here was someone who loved to masturbate as much as I did. At first, I let his comments go past, but gradually, as I came to understand they weren't just idle guy jokes, I warmed to them, or I should say blushed to them, as if we had a little secret together.
He lived in a nice house in the suburbs with a pool; I'd been there a couple of times to work with him in winter, but when summer came, he invited me out on the weekend, 'no work, just to kick back', he said. I wasn't sure I could go, and actually was a little afraid, but we made tentative arrangements. When he called to confirm, I said yes, and he said I could bring shorts to swim in if I wanted, but 'it's not really necessary.' I held the phone, and it froze in my hand, and I felt my cock stirring between my legs. In that moment, I knew for sure 'something' was going to happen. Like a cornered rabbit, my mind raced back and forth and I couldn't think of what to say 'Cool?' 'OK?' 'Yeah?', 'alright? 'Thanks?'
I think I said, 'Great', and when I showed up at his door on that warm Saturday one of his first questions was whether I brought shorts. 'Nah,' I said, trying to be cool about it, but the truth was I'd spent the whole week imagining what it would be like to be naked with him.
In a few minutes I was out at the pool, my cock a little shriveled with embarrassment, trying not to stare at his. He was a handsome man, and not overly endowed, but his cock was extremely attractive, balanced, tan, thick and held up a little by full, round balls. And he was beginning to swell.
Quickly, he turned the conversation: 'I bought this house because the yard is so private. I go around nude, and I love to come out here and masturbate.' I looked over, and his fingers were lightly touching his cock, which was beginning to show it's full size.
Well, the game was up. I knew something would happen, and now it was. For a moment, I wanted to run back to my car and into the city. Then, months of desire, months of masturbation after spending time with him, months of, yes, fantasy about this very moment...they all came together in a huge rush, and I tilted my pelvis toward him and let him watch as my cock swelled to full size.
His fingers slipped around his cock, and he began slowly stroking, and I followed suit. I could hardly touch myself, though, I was so excited! so I gently grazed the tip with my finger, letting him see how stiff and turned on I was.
'I've wanted to do this with you for a long time,' he said.
'Me, too!' and the moment I said those words, uncontrollably, an orgasm swept over me and my cock was spurting cum. I was embarrassed, and relieved, and awesome didn't begin to describe it. He laughed, said something, and I lay there and watched as he brought himself to orgasm. His cock was so thick, and his body got so hard as he neared climaxing, and then, wow, he shot cum way more and way farther than I ever imagined possible.
That was my embarrassing beginning, but the rest of the day was indescribably hot. After we relaxed a little, he came over and began rubbing my cock, and when I was fully excited, he dragged me into the living room, onto the carpet, lay next to me and put my hand on his cock while he stroked me. I'd never stroked a guy before, and it felt a little strange..plus I was about to faint with pleasure from what he was doing to ME. But I managed to bring him to orgasm, cumming in my hand, shooting on my body, and he let go of my cock but I was so excited I came touching his thigh.
We got together regularly for about three years before I moved away, and even then continued to meet up. He was a mentor in SO many ways!