I met Jack online, and though he is a few years younger than I am, at first, I thought he was a much younger man, someone just looking for a Daddy. And well, that's not really my thing as a result, initially I kept my distance. After he made a certain comment, I said to him that he only thought that way since he was so young. He asked me how old I thought he was. When I told him, mid 20s, he laughed and said his age, which was 3 years younger than I am.
After that, our conversations changed in tone and context. He's divorced, has children (grown) but is currently single and has been for some time. He runs his own company, which despite the pandemic is doing well. We began to flirt, to discuss sexual fantasies.
Jack confessed that while he'd thought about being with a man, he'd never actually been with one yet, aside from some teenage experimentation, and had only dated women. He had had toys used on his ass and had been pegged by one girlfriend. That and recalling his teenage exploration is what got him thinking about being with a man.
We continued to chat for some time. I had made an assumption about where he was located, based on his late-night posts, I decided he must be a west coast resident and US based, as well. When he suggested that we meet, I asked him how he thought we could do that, given the geographical challenges.
He informed that he lived in Scarborough (the same borough of Toronto that I live in) and we deduced that we're about 10 minutes away from each other.
I agreed to meet him for coffee at a local mall - it was the heart of the pandemic and everything was still closed due to the ongoing pandemic, but coffee shops were deemed necessities so they were open. I walked; he drove. And on a Saturday morning we met for coffee. Took it to go, the only option at the time, and sat in his car.
I've been vaccinated, and he's had his first jab.
We sat and chatted, getting to know each other. He's very cute, about the same height as I am at 5'8", nice build, not overly muscular, but not gone to pot either. He was wearing a hoodie, a tee and sweatpants, over a pair of jogging shoes. As we talked, I noticed movement in his sweatpants. I'd seen a pic of his cock, it has a narrow shaft and a bulbous mushroom head that flairs out. Someone getting fucked by that would feel it going in. Without asking, as we talked, I reached over and slid my hand into his sweats and clasped onto his semi-hard cock. No underwear.
He moaned immediately, and uttered an "oh my god" and I traced that big head with my fingertips.
Taking his coffee and putting it in the drink holder, I reached over and took his hand and brought to my own cock. I was wearing jeans, so it wasn't as easy for him to access it. But together we managed to get my cock out. He stroked it a few times and then I told him to suck it. We had discussed that he needed guidance, someone to tell him what to do, so I was taking that roll.
He tried to bend over but was knocking the coffees and he couldn't quite reach.
