I was seventeen and already living alone. My parents are a difficult story that I may tell you sometime. I wasn’t actually alone, I lived in a house full of people mostly older than myself. They accepted me, and I liked them. We were like a surrogate family. One was quite a bit older. She had a son, Keith who was sixteen at the time, just a year younger than myself.
Keith and I both worked at a shirt printing company in the afternoons. He still went to school. I had slowly dropped out, working full time at the shirt company. It was just manual labor – folding, putting shirts into boxes, taping and putting labels on the boxes. As you know, I have since made something of myself, but that’s how I started out.
Keith and I got along fine. In fact, I was becoming attracted to him. At home, I’d see him topless from time to time, and once just in briefs, and I’d aways masturbate later on to thoughts of him.
I wanted to get him alone. I kind of knew he’d go along. We both kidded each other about masturbation and being ‘gay.’ The idea for us, at the time, was that ‘gay’ was somehow wrong, inculcated by the society around us. Still, I knew that I wanted to get sexual with him, and was pretty sure he’d go for it.
I booked a hotel room downtown, about 20 miles away. I told Keith I was staying in town, just to get away for the night. I asked him if he’d like to come along. At that moment, I felt great concern that he’d say ‘no.’ At the same time, I also felt outright fear that he’d say ‘yes.’
He said, ‘Yes, but no funny business, right?’ I knew he was alluding to gay stuff. I was kind of crushed, but even still, I wanted to go through with it, even if we just stayed in separate beds and did nothing that night. I was thinking how much of my hard earned shirt pay the hotel was going to cost. Geez!
Transportation was my Vespa scooter. It was a warm evening, so that wasn’t a problem. I handed Keith my spare helmet, and we climbed on. He hadn’t ridden with me before, so I told him to hang on securely. He did, wrapping his arms around my stomach, which sent tingles throughout my body. Having Keith’s arms around me felt really nice. What I thought was odd at the time is that he had no qualms about it. Not like, “I’m not putting my fucking arms around you. That’s gay. Forget it,” which would have been his usual response.
We arrived at the next hurdle, which was the hotel’s front desk. It turned out to be no hurdle at all. They didn’t say a thing about my age. I had no credit card, but they accepted cash.
The room was nice. Typical. Two queen size beds. Keith immediately turned on the TV. It was my time to be bold. “I’m going to hit the shower,” I said.
Keith, looking at the TV, merely said, “OK.” Then he added, “Save some hot water for me.”
Now the bold part. I quickly stepped out of all my clothing right there in the room, hoping Keith would take a long, appreciative look. But no, he kept his eyes focused on the TV, evidently trying to avoid looking at me. I was in the very beginning stages of getting a boner, so I quickly ran into the bathroom. Shoot! I should have boned up in front of him. That would have been an interesting ice breaker. But then, he may have said that was too gay, which would have greatly embarrassed me.
During the shower, I had a huge hardon. It was all I could do to avoid rubbing it. I had to wait until it went down before I stepped out. Even still, being concerned that I had already gone too far with Keith, I wrapped myself up in a hotel towel before entering the room.
I needn’t have worried, Keith was as naked as the day he was born, and idly stroking a very erect penis as he was watching the TV. I thought he’d jump, or cover up immediately as soon as he saw me, but no, he just said, “Me next.”
I was delighted. I learned a lot about him in that moment. He obviously masturbated. But more, he didn’t mind me seeing him. Maybe he was even making a statement, like “Yup, it’s all OK, and I’m on board with it.” But maybe not.
I also learned what he looked like naked. He was a smallish, skinny kid, with longer than usual hair. I liked what I saw. I couldn’t really see his penis clearly, but it appeared to be small in size, and mostly hairless. I boned up immediately, but fortunately was wearing the towel.
Keith got up, walked past me, with his still-erect penis wagging back and forth, and entered the bathroom. I realize immediately, I should have let go of the towel and let him see my erection. I’d be letting him know that his erection was OK. But he didn’t seem to need any kind of encouragement. He walked past me, within a foot, erection and all, without a care in the world. How cool was that? His move was much bolder than mine. I got the impression the evening was going my way.
He took a very long time in the shower while I tried to calm my racing heart by watching something on TV. I was hoping he wasn’t masturbating in there, because if he came, I doubted he’d want anything more. I found a racy channel, which had some mild, R-rated porn. I so wanted to jerk off right then and there. Fuck it. Keith had been doing that. I took off the towel, and started touching my rock-hard penis. I would have to be careful not to get close to ejaculating yet.
Less than a minute later, Keith emerged from the bathroom, holding a towel in one hand, but otherwise naked. And erect. Very erect! He jumped on the other bed, looked at me, and said, “Are we going to do this, or what?”