Life Lesson #1: Older Guys Are Fun!

I was 24 and living on my own in a different town from where I grew up. It was far enough away that I could be anyone I wanted to be and so I got deeper into dressing up. I had a good job now, so I could afford some nicer clothes, and now that I had my own place, I could order things through the mail without worrying about prying roommates or parents.

In the city where I lived, “curious” men placed personal ads asking for guys to meet them in a coffee shop, park, or something. It wasn’t to meet for sex in public, it was just to meet, sort of a way to determine if someone was gay before you make your move I guess. One day I followed up on an ad asking to meet in the back corner of a bookstore. The ad said to pick out a specific book (I don’t remember the book) and thumb through it so the guy would know you were there answering the ad. It sounded interesting, so I went to the book store, in guy clothes of course, found the book and sat down on a nearby chair. After a few people cleared out of the section, an older guy sat down in the chair next to me - and by older I mean around 55. He asked if I had ever read that book before and I said no but a friend I was meeting here had recommended it. He took the hint and introduced himself and we made small talk for a bit, then he asked if I would be interested in continuing our conversation over lunch. I went along with it for now, not quite sure where this was going, but we DID actually have lunch and we got to know each other with some pretty interesting conversation. We will call him Jones for this story. Jones was basically just a bit lonely and bi-curious and also seemed to be into the fact that I dressed. We met up again a few more times in public for lunch and conversation and eventually I gave Jones the address to my apartment.

After a few missed connections, Jones found his way to my apartment one night and I could tell he was excited and had finally built up his nerve. I let him in and excused myself to my bedroom to get dressed.