Q: I’m a 40-year-old gay male. I live in a big city, in a dense neighborhood. While I’ve been working from home during COVID, I’ve been sitting at my kitchen table facing a big window. Across the alley is an apartment with a deck. At one point, I noticed a cute, young, muscular guy outside. I ran into this guy a few weeks later at a neighborhood liquor store. While I was looking at porn one night I was stunned to find his nudes and a link to his OnlyFans. I instantly subscribed, went through everything, including his gay sex vids, and, yeah, I came. I tipped him and put in a few comments about what kind of content he should put up next. He took my suggestions and I tipped him again. About a week ago he knocked on my door and asked if I had jumper cables. That night, I found a six-pack of beer by my door and a note from him thanking me for my help. I got back on his page and came so hard as I drank his beer. I don’t want to have sex with this guy—he’s not really my type and he’s too young. I do get off on knowing that I can pull up his dick pics whenever I want and that he will do anything for a few bucks. But I question if I’m crossing a line. He obviously doesn’t know his neighbor is jerking off to him and probably wants to keep his porn life separate from his private life. Should I feel gross about this? —Rear Window
And finally, RW, I’m not sure I believe you when you say this guy isn’t your type considering the number of loads you’ve blown while watching his porn. And while he may be too young for you—and you can absolutely set a floor—whether men in their 40s are too old for him is his call to make.
