Back in the 80s I worked with a gay man who was a few years older than me. For the first few months I wasn’t really sure if he was gay or just a little effeminate. But I could always tell he was extra interested in/friendly with me. This was a newspaper so there was one late night each week. During lulls we often would end up talking, sometimes about personal stuff. At some point he mentioned that I looked exactly like his first boyfriend in high school who had died very young. That’s why he had always been very taken with me. Of course, I was flattered even though it was a little weird being the object of desire for another man. Remember, this was the 80s.
Eventually, it came out that he really wanted to see me naked. After some persuading, I figured it couldn’t hurt and, at some point, he even offered money. OK, so for a certain amount of money – I don’t remember how much now – I would just strip for him. Don’t judge me; this was the 80s and I was making just above poverty level. So, after work one night we went back to his place and headed to his bedroom. He lay on his stomach across his bed much like a teenage girl and I stood at one corner in dim lamp light. Each time I showed a little more skin he would grunt in approval. I got an appreciative “Oh my god,” when I finally pulled my now half-hard dick out. And, yes, it was a real turn-on to have someone – even another man – waiting with baited breath for every inch of revealed skin.
Then he asked if he could touch it. I wasn’t sure about that. I mean, having another man look at me, even in a sexual manner was one thing. Touching was something else entirely. But he offered more money and, being young and broke, I couldn’t really say no. So, the next thing I know I’m being felt up by a gay man 10 or more years older than me.
I never thought I was more than average, but he constantly marveled at my size, which, of course, made me harder, hornier and more interested in continuing. At some point he asked if he could jack me off and watch me cum. I don’t remember if even more money was offered, but I said yes and the next thing I knew baby oil was flowing and I was feeling good. As horny as I was – and due to the fact that he apparently knew what he was doing, it was over pretty quickly. He cleaned me up, paid me and I left. By the time I got home I felt pretty “dirty.” But, I got over it by the time we saw each other at work again a couple days later and everything was normal – sort of.
Of course, this kind of situation doesn’t end at a single encounter. We had quite a few more interactions that escalated beyond this first one. But that’s another story or three.
Source: reddit.com/r/eroticliterature/comments/khx2c6/enticed_pt_1