I was sitting next to the window on the train into the city late one morning. It was one of those seats where someone can sit facing you on the other side, but I was alone. My headphones were on to wash out the noise and chatter around me. The first stop after mine came up and this silver daddy type gets on. He stops, scopes out the area and then picks the seat diagonal from me. We quickly looked at each other, smiled, nodded and went on with our business.
I kept scoping him out to see if there was anything that would light up the gaydar, but nothing stuck out in particular. He looked like a typical IT guy: company polo, jeans, brown shoes and glasses. Someone would text him on his Blackberry every few minutes and he would respond. It rang at one point and he picked it up to speak to whoever it was on the line. The ride continued and he pulled out a New York Times. He held it up high, which gave me the chance to check him out. This went on for some time and I figured it was crazy to pursue anything. Still, I took off my headphones and pulled out a book to increase my chances at conversation.
About 40 minutes into the ride, our knees touched. They stayed that way. I didn’t know what to do. Should I keep mine there or move it away? But it felt good and I pushed my leg into his a bit more. Again, it stayed. Finally, I rounded up the courage and began to push slightly. He pushed back. I looked at him and he looked at me. I smiled. The pushing turned into rubbing. His newspaper came out again and he placed it over his crotch. He pretended to read while his other hand rubbed the bulge that formed in his pants. Finally, he looked at me, got a bit closer and said, “It’s been years since I’ve met anyone on the train.”
We soon arrived at our destination and exchanged phone numbers. He gave me his business card, but scratched out the address and wrote his personal email, which was the dimensions of his penis. It seemed a bit corny and ridiculous, but it had been some time since I last had sex. “Want to come back to my office?“ he asked. I told him I had to get to work, but maybe we could meet up some other time. We parted ways and I texted him on my way to work so he would have my number. He texted me back right away telling me he already added me to his contacts and that our encounter on the train made him really horny.
The next day after work, we met up at a burger joint and had a couple drinks. We had a decent conversation about how we both came to realize our “faggotry” and moved on to stories of past experiences. When no one was looking, we would use the opportunity to feel each other up. Still, despite all this, I questioned his sincerity. It’s not that he had said or done anything wrong at that point, but that gut feeling that something wasn’t right kept going on in the background.
After we were done, we headed out to parking lot where he invited me into his pick-up. “Now give me a big kiss,” he demanded. I tried to hold back, but I was really horny. We made out for a bit, although I was nervous someone I knew would pop up out of nowhere. Then he pulled out his really thick dick and we looked at each other for a second. I scoped out the area to make sure no one was watching us and then went down on him. After a few moments, he asked, “Do you want to stay here or go to the parking garage?”
I got into my car and followed him to a garage about a block away. We drove to the corner of the bottom level where there were no other cars. When I got out of my car, he was already outside of his truck with his pants at his ankles. We started making out and I began jerking his cock. He opened the door to the extended cab and told me to have a seat. He started sucking me off as I rubbed the top of his head. After a while, I told him I wanted to switch and I blew him until my jaw was sore. He pulled out some lube and started rubbing it on my cock and bent over. “What are you doing?” I asked. “Well, I put lube on your cock. What do you think I want you do? This is your first time, right?” He was right. I admitted I had never fucked anyone in the ass during our conversation and this seemed to excite him. Also, neither one of us had a condom. But I jammed it in there anyway. I was nervous as hell and paranoid someone would walk in. The nervousness combined with the fact that we were fucking in the back of a pickup made me unable to perform well and I pretty much called it quits on the sodomy. So we proceeded to give each other blowjobs. As he was going down on me, he came and blurted, “I wasn’t expecting that to happen!”
Afterward, we made out and then he said he had to tend to business. At this point, I had not come at all, even though he promised me in the beginning. I felt like a piece of shit for going through with everything, and I couldn’t shake the feeling that I had fucked up. I had broken one of the most important rules I had set for myself when it came to hookups, which was to only hook up with a condom. “You’ll send me of video you cumming, right?” he asked. I nodded yes, but in my head I clearly said no. The next day I asked if he was serious about the video and he texted back, “Yup.” I didn’t text him again.
Two weeks later, I was sitting in the library fixing up my resume and my phone vibrated. It was him. He asked how I was doing. I said I was doing well and played along with the flirtations. He told me to get back to him if I wanted to meet up at a bar or go out to lunch.
I never did.