An Actual First Time Gay Experience (pt. 4)
The beginning of that Summer seemed like lifetime ago. A couple weeks in and I'm watching porn with a stranger, jerking off with him, then us jerking each other off. Then sucking dick. Some days turned into everyday. Lying about where I was, what I was doing, and having it all be with Craig. This older man who saw something in me. Something he wanted, I'm pretty sure he knew I'd be open to exploring this with him. No other young guy like me would have gone so, even gotten to jerking off with this man if they were against it. Me? It was my shot to experience something I had spent a lot of time thinking about, getting turned on about. When Craig opened the door, it was my best shot to walk through.
And that brought me to where I was here. I had at this point been accepting to the fact that Craig was the one calling the shots now. He'd rarely sucking my dick anymore, but it was my job to suck his. And this was a job I loved, by the way. I had learned how delicious his cum was. I remember it being thick, big wads that were salty and just a bit sweet. It was the first cum I truly loved. And I'd swallow it as much as he could provide it. Though, it was his call where he came on me. While most times it was in my mouth, he'd also cum on my face. Which, like I said, his wads were so big they glazed my whole face. Then he'd have me collect it with my fingers and eat it. Either way was a win for me.
But here it was. Time for the next level. I knew it was coming eventually. You don't have this guy over each day, naked, watching porn, jerking off, and sucking your dick before the time comes to fuck. Actually fuck.
Craig had already been fingering me, stretching my whole a bit with lube. He was ready after a while of that, though I wasn't sure I was. But Craig ran the show now, and I wasn't going to say no. He had me arching my back, slathered up my hole with lube, and covered his cock too. He began rubbing his cock up and down between my ass cheeks, slowly. His breath picked up a bit. Deeper breathes. He then leaned down over me, and said "this is where don't turn back." He then nibbled on my ear a bit "You're going to have a pussy now." He had already brought up me getting this new "pussy". And when I felt the head push against my hole, I knew one thing, and this was the point of no return.
His cock was rock hard, and the head felt like it was way bigger than when he had his fingers in me. But that moment. That moment when his helmet breached me and went inside, it was almost excruciating. It hurt, and I tried to move away, but his hand went from guiding his cock to grabbing hips. He told me to never run. That I would learn from this and enjoy it. I was terrified. But I couldn't do much. I was frozen at that point, feeling him slowly fill me. To Craig's credit he did take it slow. He slid into me for what felt like forever. It burned and stung and I could feel his cock stretch me out. "This pussy is SO good!" I rember, crystal clear, "this is going to better than I've had in a long time." As that initial entry came close to an end, he did warn me about the end, and shoved the last inch into me. I remember the scream.
But he kept up. And thankfully he kept lubing us both up. As the fucking went on, I kept going from crying to a dull whimper. I had to learn. I had to. After a while, he had me flip over onto my back. "You're going to get to love this. Fucking is so great, and your pussy is beautiful." I didn't know how to respond or what to do. But his cock slid back in, and I leaned my head back and moaned. "See, you like it." This is when he grabbed my legs and lifted them up. He placed them on his shoulders and grabbed my hips. He picked up his tempo. He was fucking me faster and deeper, and while I kept my head back, I realized my eyes were rolled back and I was moaning.
I was starting to like this.
Of course he was at the point just before what I'd call full on fucking. He was in the zone. And as I felt his cock slide in and out, I was experiencing something new. Having my prostate stimulated by this thrusting. It was amazing. He then slowed almost to a stop and looked at me. "You can't have a pussy with cum." He started back up. This time things went quickly. He started slow and ramped up fast. Then I could feel something. That feeling when his cock was about to blast a load in my throat. But now it was a sensation around my hole. He grunted and pulled me in, smashing his dick into me as hard as he could. Not expecting it, I cried out before I felt it inside me. I could feel his cum. It was so warm.
He collapsed by my side, smiling. "Not so bad?" he asked. I shook my head no. "Well, you've got yourself a cum-filled pussy now. And I expect to start getting it regularly. Do you understand?" Of course I did. He had just broken me in. Just about all bases covered. I kept returning. Kept sucking his dick, still getting fucked. I really did get to love the fucking. We'd do it wherever we could. On my favorites was when I'd be doggy style and we'd both be watching guys doing the same in those porn videos.
It was full circle.
And that brought me to where I was here. I had at this point been accepting to the fact that Craig was the one calling the shots now. He'd rarely sucking my dick anymore, but it was my job to suck his. And this was a job I loved, by the way. I had learned how delicious his cum was. I remember it being thick, big wads that were salty and just a bit sweet. It was the first cum I truly loved. And I'd swallow it as much as he could provide it. Though, it was his call where he came on me. While most times it was in my mouth, he'd also cum on my face. Which, like I said, his wads were so big they glazed my whole face. Then he'd have me collect it with my fingers and eat it. Either way was a win for me.
But here it was. Time for the next level. I knew it was coming eventually. You don't have this guy over each day, naked, watching porn, jerking off, and sucking your dick before the time comes to fuck. Actually fuck.
Craig had already been fingering me, stretching my whole a bit with lube. He was ready after a while of that, though I wasn't sure I was. But Craig ran the show now, and I wasn't going to say no. He had me arching my back, slathered up my hole with lube, and covered his cock too. He began rubbing his cock up and down between my ass cheeks, slowly. His breath picked up a bit. Deeper breathes. He then leaned down over me, and said "this is where don't turn back." He then nibbled on my ear a bit "You're going to have a pussy now." He had already brought up me getting this new "pussy". And when I felt the head push against my hole, I knew one thing, and this was the point of no return.
His cock was rock hard, and the head felt like it was way bigger than when he had his fingers in me. But that moment. That moment when his helmet breached me and went inside, it was almost excruciating. It hurt, and I tried to move away, but his hand went from guiding his cock to grabbing hips. He told me to never run. That I would learn from this and enjoy it. I was terrified. But I couldn't do much. I was frozen at that point, feeling him slowly fill me. To Craig's credit he did take it slow. He slid into me for what felt like forever. It burned and stung and I could feel his cock stretch me out. "This pussy is SO good!" I rember, crystal clear, "this is going to better than I've had in a long time." As that initial entry came close to an end, he did warn me about the end, and shoved the last inch into me. I remember the scream.
But he kept up. And thankfully he kept lubing us both up. As the fucking went on, I kept going from crying to a dull whimper. I had to learn. I had to. After a while, he had me flip over onto my back. "You're going to get to love this. Fucking is so great, and your pussy is beautiful." I didn't know how to respond or what to do. But his cock slid back in, and I leaned my head back and moaned. "See, you like it." This is when he grabbed my legs and lifted them up. He placed them on his shoulders and grabbed my hips. He picked up his tempo. He was fucking me faster and deeper, and while I kept my head back, I realized my eyes were rolled back and I was moaning.
I was starting to like this.
Of course he was at the point just before what I'd call full on fucking. He was in the zone. And as I felt his cock slide in and out, I was experiencing something new. Having my prostate stimulated by this thrusting. It was amazing. He then slowed almost to a stop and looked at me. "You can't have a pussy with cum." He started back up. This time things went quickly. He started slow and ramped up fast. Then I could feel something. That feeling when his cock was about to blast a load in my throat. But now it was a sensation around my hole. He grunted and pulled me in, smashing his dick into me as hard as he could. Not expecting it, I cried out before I felt it inside me. I could feel his cum. It was so warm.
He collapsed by my side, smiling. "Not so bad?" he asked. I shook my head no. "Well, you've got yourself a cum-filled pussy now. And I expect to start getting it regularly. Do you understand?" Of course I did. He had just broken me in. Just about all bases covered. I kept returning. Kept sucking his dick, still getting fucked. I really did get to love the fucking. We'd do it wherever we could. On my favorites was when I'd be doggy style and we'd both be watching guys doing the same in those porn videos.
It was full circle.
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