One time his girlfriend was out of town, and he invited me over. Even though he knew I didn't drink, he slipped me a soda full of rum, in what I realize now was an attempt to keep me from leaving and to get me buzzed enough to make a play for him.
Time went by, and Tim had plans to get married. One night in the months before he married her, we went out drinking. We went to a straight bar he hung out in, and I took him to a gay bar I went to. It was a great excuse, it had our favorite pinball table. My boyfriend at the time met us there, and he was completely infatuated with Tim. He told me all the time how he read Tim as "bi-curious", and I admitted I felt the same thing from him, but I didn't want to mess up our friendship. I remember that night, my boyfriend dared Tim to kiss me on the lips and he did. It wasn't passionate, but it wasn't just a peck, either. In a brief moment, he leaned in and I felt his lips on mine, and I started to really feel for him.
Since Tim and I arrived before my boyfriend did, we left in separate cars. My boyfriend went back to my apartment to wait for me, while I went to drive Tim home. We ended up sitting in my car in the dark parking lot, and he got out some pot. I hadn't ever smoked any before, never even tried it. He told me if I smoked pot with him, he'd show me his dick. I saw where it was going, so I gave in. I tried the pot, did nothing for me. But then we were sitting there and I said "OK, now you have to show me your dick." He sighed and said "Yeah, you're right, I said I would." With that, he undid his pants and slid them down to his ankles. "There it is," he said. It was a little overwhelming for me. His dick was soft, but I didn't care, it was more about the intimacy he was sharing with me. Something was strangely non-erotic about it, though. It wasn't the way I'd hoped it would be, us sitting there in public where we couldn't really do too much and get away with it. I wasn't hard at all, and I probably wouldn't have been able to get hard if he'd wanted me to.
I praised his cock though, because I did like it. He had huge nuts too, which was very exciting to me. "You want to touch it, don't you?" I nodded. "Go ahead," he said. So there I was, feeling up his cock and his balls. I did my best to make sure he knew I was enjoying it. "What would you guys do now, jack off?" he asked, "you guys" meaning gay dudes. I said "Yeah, I guess." "So jack me off," he said.
But he never got hard, no matter how I stimulated him. "You want to suck it, don't you?" he asked me, his voice suddenly very deep. I immediately said "Yes." He answered just as fast, "You can't." I guess that was going too far for him. I played with his limp dick another minute or so, and then it was over. He pulled up his pants and we went back to being laughing buddies. "Dude, I feel like I passed a test or something, like I was about to go gay and I didn't!" I didn't know what to think, or feel. On the one hand, I wanted to suck him more than anything I'd ever wanted up to that point. But somehow it didn't happen, and I was glad that it didn't happen. I didn't want it bad enough to make it happen.
A few years later, after he was married, it almost happened again. He invited me to his house while she was out of town, and this time he had a buddy there. They were smoking pot in his garage, and I had some. This time the pot worked, I got buzzed, and I started to pick up on two things: number one, the presence of his buddy really got to me. I hadn't realized Dennis would be there, and it spoiled what I thought would be an evening alone for Tim and myself, an evening where we might finally consummate what had been building between us ever since that night in the car. There had been other flirtations after the car incident. We joined a gym together and I'll never forget one day when I caught him in the showers. We stood in full view of each other, and I saw him completely naked for the first time. Broad shoulders, beefy chest and round, firm gut, and this amazing ass I just wanted to slap around. I tried not to look. I tried not to do anything, because I genuinely liked Tim. I felt close to him, and sex didn't really matter to me all that much.
But that night at his house, I felt it again. Tim wanted me to sleep over, and at some point I know he wanted me to make a pass at him. I also think he wanted me to suck Dennis's cock, too. He had told me a lot about Dennis, about how his wife didn't like sucking his dick, and it almost seemed like a dare. Dennis was sleeping over, and Tim offered me a couch in his den to sleep on.
I didn't stay. I had a work obligation for one, and for another thing his wife was coming home early, and I didn't feel like waking up and high-tailing it out of their house before she got home. But mostly I felt that same nagging disappointment. Tim wanted me to make a pass at him, and I didn't think it would go well between us. He might have freaked after getting a blowjob from a guy, and our friendship would have immediately been over. I valued it too much to risk that.
Turns out, I should have just gone for it. Our friendship went sour anyway, for superficial reasons that can probably be traced back to the fact that I never put out for him. He wanted some experience and I wasn't going to give it to him, and that was that. If I'd known then how it would all turn out, I would have given him blowjobs all the time that might have changed his life. As it stands, I just have a few memories, the best of which is that brief kiss. That's probably the part he remembers least.