An Actual First Time Gay Experience (pt. 3)
At this point, it's mid Summer. A lot of the other people my age were out doing typical things. Sports, hanging out, movies, parties. While I did do these things, it certainly wasn't nearly as much as them. My time became spent more at Craig's. It was a lot more of a different Summer than I originally thought about. I never expected I'd be naked with a man at all, let alone one 30 years my senior, getting off on hours and hours of gay porn and sucking cock. I never thought I'd be another man's "boy".
There was a ritual now, just an unspoken sequence of events when I came over. I had been pushing my lawnmower over, just to keep up appearances, mostly at home. I'd leave the mower in the backyard and come in through the sliding door and brush aside the closed curtains. Craig would be waiting, naked, waiting on the couch. Whatever. As soon as I came in, I'd take my clothes of, as this became the rule. There was kissing now, deep passionate kissing, but it was more of the sensual and erotic kind. We both knew what we were in, and it was a solely sexual relationship. We'd decide on which porn we were going to put on first and start rubbing each other's bodies. Craig had gotten to a point where he loved my nipples, and would spend time licking, sucking, and biting them. It drove me fucking wild. He knew it too.
A lot of our time was spent sucking cock, and as time went along, it became a situation where it was less about reciprocation and more about me sucking him off. He told me I was his boy, and I had to take on a submissive role. He didn't quite use those words. He said it was "feminine responsibilities". At this point, already being all in on these visits with Craig, on our bodies together, the feel of his cock. I accepted these "responsibilities". As far as sucking his cock, I learned quickly how to use my tongue and lips properly, and the feel and taste of his cum. His loads were large, and he usually fired off two or three in a row. They were thick and a bit salty. I came to love those loads, to make sure I tried to swallow each and every drop. He taught me to deep throat. But, of course, there was one thing missing. While blowjobs were great, and growing submission coming into place, there was another responsibility I needed to take care of.
I remember us being in his bed. We were in there so he could spread his legs nice and wide and push my head down while I drooled all over his dick. It was a usual situation. After a while, he hot up and told me to stay on my hands and knees. I did as I was told, and watched as he pulled a bottle out from the drawer on his nightstand. Craig said to me, which I'll never forget, "Boy, one more thing I'll need from you is a pussy, and I making your pussy now." I wasn't dumb, and knew what he meant. I started to rise from from knees, but he put his hand on my back and pushed me back down. It wasn't violent or painful, but it was definitely stern and made a clear point. I was breathing heavy, as nervous and as panicked as when I first started exploring with Craig. This was going to be different though. This was going to be where I truly going to experience being with a man, no matter if I wanted to or not. But like all those weeks ago, I also was ready somewhere in the back of my head. We had made it to this point. The point, for me, of no return.
The lube was cold. Craig attempted to warm it, but it didn't quite work, and he apologized for the chill. While being the true Man in this situation, he wasn't being rough or cruel. He just knew I was going to stay here, basically because he told me so. He put a generous amount of lube around my asshole, and then slowly it began. I felt pressure, then the deliberate insertion of his middle finger. I gasped in shock and pulled forward, but he put his other hand around my balls, tugging gently, but with a grip "don't pull away". His finger slowly went in and out, and I moaned, because there were moments it hurt. He let go of my balls and put his free hand on my back while his other hand was fingering me. "Put your head down, it will be more comfortable. But leave your ass up." I did what he said, and continued to moan as I felt his finger move in and out, exploring my insides, giving me this weird feeling of pain but also a touch of pleasure.
It was after a while that Craig said it was time for more "Boy, we need to make sure your pussy is ready, so it's going to get stretched out a bit." There was the second finger, along with more lube. I'm pretty sure I let out a cry. It was almost too much. That second finger was joining the other, stretching my hole, and putting more pressure inside me. He fingered my ass to where he was moving a bit faster, and knuckle deep. He'd reassure me as I cried and moaned, but attempts to pull away were met with those tugs on my balls, which were more deliberate each time. After what was probably an hour or more, time got away from me, he pulled his fingers out and said "Your pussy is so tight, boy. I think it's time we pop that cherry".
I braced myself as he began to spread lube on his cock and scooped more in and around my hole. It was going to be a pussy soon. I was his boy, but in reality, I was going to be Craig's bitch, and the rest of this insane Summer was going to be spent living out what I had been curious about for so long.
But we haven't even talked about the actual fucking yet.
9
There was a ritual now, just an unspoken sequence of events when I came over. I had been pushing my lawnmower over, just to keep up appearances, mostly at home. I'd leave the mower in the backyard and come in through the sliding door and brush aside the closed curtains. Craig would be waiting, naked, waiting on the couch. Whatever. As soon as I came in, I'd take my clothes of, as this became the rule. There was kissing now, deep passionate kissing, but it was more of the sensual and erotic kind. We both knew what we were in, and it was a solely sexual relationship. We'd decide on which porn we were going to put on first and start rubbing each other's bodies. Craig had gotten to a point where he loved my nipples, and would spend time licking, sucking, and biting them. It drove me fucking wild. He knew it too.
A lot of our time was spent sucking cock, and as time went along, it became a situation where it was less about reciprocation and more about me sucking him off. He told me I was his boy, and I had to take on a submissive role. He didn't quite use those words. He said it was "feminine responsibilities". At this point, already being all in on these visits with Craig, on our bodies together, the feel of his cock. I accepted these "responsibilities". As far as sucking his cock, I learned quickly how to use my tongue and lips properly, and the feel and taste of his cum. His loads were large, and he usually fired off two or three in a row. They were thick and a bit salty. I came to love those loads, to make sure I tried to swallow each and every drop. He taught me to deep throat. But, of course, there was one thing missing. While blowjobs were great, and growing submission coming into place, there was another responsibility I needed to take care of.
I remember us being in his bed. We were in there so he could spread his legs nice and wide and push my head down while I drooled all over his dick. It was a usual situation. After a while, he hot up and told me to stay on my hands and knees. I did as I was told, and watched as he pulled a bottle out from the drawer on his nightstand. Craig said to me, which I'll never forget, "Boy, one more thing I'll need from you is a pussy, and I making your pussy now." I wasn't dumb, and knew what he meant. I started to rise from from knees, but he put his hand on my back and pushed me back down. It wasn't violent or painful, but it was definitely stern and made a clear point. I was breathing heavy, as nervous and as panicked as when I first started exploring with Craig. This was going to be different though. This was going to be where I truly going to experience being with a man, no matter if I wanted to or not. But like all those weeks ago, I also was ready somewhere in the back of my head. We had made it to this point. The point, for me, of no return.
The lube was cold. Craig attempted to warm it, but it didn't quite work, and he apologized for the chill. While being the true Man in this situation, he wasn't being rough or cruel. He just knew I was going to stay here, basically because he told me so. He put a generous amount of lube around my asshole, and then slowly it began. I felt pressure, then the deliberate insertion of his middle finger. I gasped in shock and pulled forward, but he put his other hand around my balls, tugging gently, but with a grip "don't pull away". His finger slowly went in and out, and I moaned, because there were moments it hurt. He let go of my balls and put his free hand on my back while his other hand was fingering me. "Put your head down, it will be more comfortable. But leave your ass up." I did what he said, and continued to moan as I felt his finger move in and out, exploring my insides, giving me this weird feeling of pain but also a touch of pleasure.
It was after a while that Craig said it was time for more "Boy, we need to make sure your pussy is ready, so it's going to get stretched out a bit." There was the second finger, along with more lube. I'm pretty sure I let out a cry. It was almost too much. That second finger was joining the other, stretching my hole, and putting more pressure inside me. He fingered my ass to where he was moving a bit faster, and knuckle deep. He'd reassure me as I cried and moaned, but attempts to pull away were met with those tugs on my balls, which were more deliberate each time. After what was probably an hour or more, time got away from me, he pulled his fingers out and said "Your pussy is so tight, boy. I think it's time we pop that cherry".
I braced myself as he began to spread lube on his cock and scooped more in and around my hole. It was going to be a pussy soon. I was his boy, but in reality, I was going to be Craig's bitch, and the rest of this insane Summer was going to be spent living out what I had been curious about for so long.
But we haven't even talked about the actual fucking yet.
9
11 months ago
