Let me tell you about my buddy who I will name "Vince." Vince is a little older than me and we met by messaging each other on Grindr. He's a pretty built guy who was just as tall as I was, maybe a bit thicker. He has a girlfriend who I think was okay with him fucking around with other women, but didn't know that he was also looking into messing around with guys too.
He was primarily looking for another guy to jerk off with. Nothing super serious and I thought it would be hot to have a jerk off buddy too. We met up and immediately got to jerking off.
He never touched another guy's dick before, with mine being the first he's ever touched. I can remember him commenting how he really liked the shape of it and how hard it felt. I jerked him off until he came all over my hand. His cum was so thick and warm. I didn't cum, but it was hot to get him cumming.
We met a couple more times with things gradually getting a bit more curious from him. He asked if he could suck my dick and of course I said yes as someone who loves getting sucked. I can remember him kneeling before me, hesitating a bit as he first licked the head to taste the precum oozing out. Then he takes one hand and wraps it around my dick as his lips slowly wrap around my head and he slides on down. He was new to sucking dick so I didn't want to ram my cock into his throat to make him gag and choke, so I let him go at his own pace. His moans when he would taste my precum was so hot though. Again, I didn't cum, but got him to cum by jerking him off some more.
Things escalated a bit more with the next encounter as he asked me if I wanted to milk him. Of course, I wanted to. So he bent over for me as I lubed up my fingers and slid into his super tight hole. Damn was it tight because it was wrapping around my finger like a vice. I finger his prostate and give him enough pressure to make sure he's feeling the pressure. As one hand finger fucks him, the other strokes his cock. He moaned so loudly as I was stimulating him and came in no time. He shot so much fucking cum from getting finger fucked by me. This was enough to get me so hard that he was finally able to see me cum after I jerked off and used his own cum as lube.
In between the time of us meeting and hanging out to jerk off or whatnot, we would chat and text each other. And something he mentioned a couple of times is that he thinks he would be okay with me fucking him. I told him that I'd be down once he felt ready. And that day finally came.
I could tell he was really nervous when he got to my house, the guy has never been fucked after all. When we sat on my couch, I was easing him into it a bit more by touching his thighs and reassuring him that if he wants to stop we can stop. But boy was he determined to finally get his cherry broken by me.
We pull down our pants and he's already hard just at the thought of getting fucked by me. We do our usual of reaching for each other's cocks and stroke and feel. I was precumming so much from the thought of fucking my friend who has been presenting himself as this "straight" guy for as long as I've been talking to him.
Gradually we both got harder and harder and heated up to the point that I couldn't stand getting stroked and that I needed to fuck his ass. He gets down on all fours, his thick ass pointed at me.
I lube up my dick and slap it against his tight hole to tease him. He wags his ass at me a bit, almost begging me to slide it in him. Slowly, I enter his tight, puckered hole. I push past the tight ring of muscle and he let out the hottest moan I've ever heard him make. I press further and further inside him, going slow to ease him into it. He was so fucking tight, I swear my dick was going to get gripped and pulled off.
Once I get all the way inside him, he moans loudly again. I instructed him to take several deep breaths so he can get used to having me inside him. Once he felt more ready, I slowly start moving. I pull my cock out just enough to keep the head inside him before pushing back in.
When I pick up my speed, his breaths became a bit ragged and sweat was forming on his head. I squirt on a bit more lube to help with the tightness and friction to help with the speed I was fucking him at.
He moans softly with every single thrust hitting deep inside him, his cries of pleasure were nothing I ever heard him say before. "Fuck me! Fuck me! God that feels so fucking good!"
His hole felt so fucking good. It was so hot and tight, gripping around me with such an intensity that it felt like it would just suck me back in every time I moved back. I hit him deep and hard, my fingers digging into his hips and I thrust his thick juicy ass. Every time I thrust in, his ass would bounce. I slap his ass, making him moan. Each thrust was getting harder than the last.
I could feel his contractions with every thrust and I knew he was about to cum hands free. But I didn't want him to yet.
"No, I want more," he whimpers. I slow down my pace until I pull out. He looks back at me and asks, "You okay?"
"Yeah, get on your back," I tell him.
He does as I tell him and rests on his back. I pull his legs up over my shoulders and line my cock up with his hole that's waiting for me to fill it up again. I push in, and the entry is much easier this time around. I push all the way in him and now I can see his face in all of its flushed pleasure. He moaned and his eyes were glossed over.
I pound my cock into him, his body shaking with every single thrust. His breathing gets ragged again and I can tell he's enjoying himself with just how much he's moaning and holding onto whatever is nearby to brace himself for each of my thrusts.
"Fuck me bro! Fuck your cock feels so good in me! I didn't know it would feel so good having you fuck me!" he moans loudly. He was desperate for me to fuck him nice and hard.
I reach down and grab a hold of his cock and start stroking him in rhythm with my thrusts. His moans were getting me into a lustful frenzy which only urged me to fuck him faster and harder.
I pound into him without abandon, making sure he feels every goddamn inch of my cock inside of him. Vince's hole contracts around me and I knew he was close again. He cries out, "I'm cumming! I'm gonna fucking cum!"
He bangs his head against the floor, his eyes rolled back and in a total daze. Within seconds his thick hot cum shoots straight out of his hard cock and shoots all the way up his chest and drips down my hand that was stroking him. The moan he let out was so loud and so fucking hot.
With him tightening around my cock so much, I was ready to cum. I warn him, "I'm gonna cum soon."
"Cum inside me bro! I want to feel your cum inside me!" he cries out, drooling and a complete cloudy mess.
I thrust in him some more, pushing deep and hard with each one. With one good thrust, I can feel the cum shoot out of my cock and inside of Vince's tight hole. I let out a moan that mixes with his as he feels my hot cum filling him up. His ass clenches around me tightly to milk me dry. My cock pulsates to shoot out every drop of cum that I was holding in, and I was holding in a lot of cum that day.
Once I felt the last bit of cum shoot out, I slowly pull my cock out of his hole. He arches his back and moans when he feels the head of my cock pop out of his tight hole. I take a moment to catch my breath and wipe the sweat off my forehead. I reposition myself to kneel next to Vince's head and slap my cum-covered cock against his face.
Without even needing to be told, Vince takes my cock into his mouth to taste the mix of my cum, sweat, and lube. He happily devours my cock and I watch his hungry mouth at work and admire the fact that he was once such a hesitant guy who now happily is taking my cock.