Sometimes you end up involved in things that when you look back on it, you have no idea how you got there. In my twenties, I didn’t really know what I wanted to do, and was renting a house with a couple of people. Nobody had a lot of responsibility, but the pay was okay enough that rent wasn’t a struggle for three people. One of my roommates (Bob) had a bunch of out-of-town peeps, so every once in awhile they would be gone for a few days, and my other roommate (Greg)was there to escape their family situation because it wasn’t that great. Turns out it was partly because they were gay, and they really wanted to strike out on their own without all the baggage. I had had friend-of-a-friend gay friends before, but nobody that I had interacted with directly as much as him. I was both eager to have a friend and curious about his sex life.
One of the times that was Bob was gone for a weekend, Greg and I had decided that we would watch some porn together. Greg hadn’t watched that much straight porn, but I certainly noticed some nights waking up to get a glass of water that Greg would be watching gay porn. Once or twice I left my door cracked to see if I could look down the hall from my bed into the living room to see if I could keep watching. I didn’t see much and it never amounted to anything, so I was a little surprised when Greg made the suggestion and let me pick the movie.
The living room was kind of sparse, mostly because even though we had a decent TV stand, we didn’t really have a couch at the time. Nobody had a truck, and we hadn’t quite figured out thrift stores yet, and nobody wanted the commitment of a shared expense. I grabbed one of the chairs out of the kitchen to sit on like I would normally use to watch movies and Greg sat on the coffee table. I suppose we could have both sat on the coffee table, but either I was apprehensive about close contact,or about knocking the coffee table over, but thinking about it now it seems like the whole thing would have gone a lot differently if we had had a couch.
It was the weekend, so the dress code was totally t-shirts and gym shorts. However, the comfy pair of Converse gym shorts I had didn’t hide that much once I became excited because they weren’t that baggy. All I remember from the movie that I had picked out was that the main actress was blond and had big tits and I spent most of my time fixated on her. I edged as long as I could until I had a wet spot on the front of my gym shorts, and finally took off my gym shorts because the wet spot felt weird. Greg might not have noticed the wet spot, the only light in the room was from the TV. Greg had rubbed himself from time to time during the movie, but I got the impression that he was watching me more than the movie. Once my shorts came off, I felt like I had to start over a little bit, but I definitely wasn’t apprehensive about Greg being there. After a few more minutes of direct contact, I came all over the tile floor, and it wasn’t until after I came that Greg whipped his dick out, told me how hot it was to see me come, and then came himself. I stayed out in the living room and watched more of the porn, but Greg excused himself to his room after cleaning up. I guess I felt like I wanted to get my rental’s worth, instead of listening to what Greg was trying to tell me about “if I needed anything else to let him know”.
It was probably another month before we had the opportunity to do anything like that again. Greg and I were walking back to the house in the evening after running a errand. There weren’t any other pedestrians out, but there was a lot of traffic on the road. We ended up talking about the last time and Greg told me that he wished that he could have watched from a closer vantage point where he could see better. So, when we got to the house, I was sitting on the toilet and he was sitting on the edge of the tub, jerking together. No porn this time, I guess because the act itself felt a little taboo for me, and I was all the motivation that Greg needed. It didn’t take long for me to get close, and I assumed that I was just going to scoot back on the seat and shoot directly into the toilet like I might normally do when I was jerking off in the bathroom, but as soon as it seemed like I was getting close, Greg just leaned down and took the head of my cock into his mouth and I immediately came. It was a lot to process for me at that moment, because it was a little unexpected for me, and then it got weirder because Greg just stopped without coming and I felt bad that he didn’t finish. It had not occurred to me that me coming in his mouth was actually what he wanted.
The third time was different, because he started by kissing me, and I was again caught off-guard by the new sensations. I didn’t react to the kiss much, and didn’t even think of trying to touch him at this point, so I was kind of under-reactive while he pushed me onto the floor and gave me a very aggressive blowjob. I still think about that because nobody else had ever duplicated the feeling of so much suction on my glans (but I never tried one of those penis pump gadgets, either).
Unfortunately, that put a rather one-sided feel on the whole arrangement. I had even tried to jerk him off a few times and might have done more, but was always shooed away before it got too far along. It started to seem like he wanted to have my cum in his mouth, and that was it. At a certain point, he decided he needed to move again, but we still saw each other from time to time. He got me to realize that I liked getting rimmed, but that knowledge was of limited value when he was the only person that would do that to me. I don’t know why it never escalated to much else, and I was later disappointed by the idea that we never figured out about frotting, or maybe like a bunch of other things between us I spent too much time being overwhelmed by things to figure anything out.
Once I had even come by where he was staying, sweaty from mowing the lawn on the weekend, and grabbed a shower in his bathroom wondering if he would just climb in the shower with me, but it was also a tiny shower. We spent a fair bit of time trying to respect each other’s boundaries, even when we didn’t know what they were.
He moved further away, and got a job with better healthcare, and I would see him every couple of years and while he was more comfortable with me doing things to him we still weren’t quite in sync. I did try to return the favor a few times, and the closest I got was giving him oral long enough for him to get excited enough to have me finish him with my hand. He hungrily licked his own cum off of my hand, and in a strange turnabout we were done and I didn’t feel the need to come and we walked off to whatever else we were doing, partly because I was freaked out about being in a dark parking lot on a holiday weekend and worried the cops would come find us.
Given another opportunity, I fear I will still be as clueless as ever, because there’s always the disparity between what we think we should do and the expectations of other people. Maybe I will feel better about it if I can find another pair of those comfortable gym shorts.
Source: reddit.com/r/eroticliterature/comments/ps05yt/melancholy_and_reminiscence_mm