I have known him for a decade by now. I shall call him HB, short for Hungry Boy, in this post. The first time I met HB was when he just started his JC 2. He messaged in me in Dudesnude with his face pic. A cute boy with some body definition, probably from some CCA sports, nice large pale brown nipples, and a big sweet smile. He was 17 years old in his profile, 170cm tall (or maybe less), around 60kg heavy (or maybe less too). His message said that he was a virgin boy who just decided to explore his sexuality and was looking for someone experienced. When I asked him if he was gay or just curious, he told me that he was definitely gay. That was good to me, because curious boys often tend to be passive during sex. I told him upfront that I was a top and wasn’t interested to get fucked, and asked him if he had any experience with guys. He replied that it was cool because he was indeed looking forward to try getting fucked. He had non-anal fun with two guys so far. Both guys wanted more but he wasn’t ready for any anal action, either as top or as bottom. We set a date and decided to meet in a hotel (the 2-hour booking kind) because neither of us had place. I specifically told him what to clean up his boyhole and he enthusiastically acknowledged it.
On that day, we met at a coffee shop nearby the hotel first. I was certainly pleased at how he looked in real life. He was definitely a cute boy, somewhat droopy eyes with pimple marks on both his cheeks, not too much and overwhelmingly turning off but just enough to add a hint of extra cuteness. He was also certainly pleased at what he saw. The first thing he said was actually a compliment to my big arms and chest. He was all smiley but slightly nervous. I walked him to the hotel, but we separated when nearing the hotel. I told him to wait there while I checked in, and go up only when 10 minutes have passed. So I checked in, got the key, got in the room, and he came in about 5 minutes. The hungry boy couldn’t wait, he immediately grabbed me and hugged me tight as soon as he put down his bag. His hands were all over my body even though I was still fully clothed. I took off my shirt and he let out a faint “wow” sound. I pushed his head closer to my chest and his tongue instantly danced around my nipples. He actually did a pretty decent job. I sat down on the chair and he knelt down, continuing to suck one of my nipples while his hand played with the other one. My cock got hard, so much that it strained the undie. As I removed it, I saw a boy with a look full of marvel. He said that was the first time he saw a real muscular guy naked in real. He caressed my bulge with both his hands, for a moment I wasn’t quite sure what he wanted to do with it. So I pushed down his head to my crotch and he started licking it while inside my brief. That was enough for now, I thought, so I pulled him up and motioned him to remove his t-shirt. His bod was not bad at all, there is a slight definition of chest and abs, but lean overall. His nipples are like the main features of his bod, considerably large although not really perky. I pinched both his nipples hard, and he gave out a moan. While still pinching, I asked him if he liked that. And he nodded with his pleasured look and moan. I removed his shorts and briefs, exposing the 5.5” uncut, slightly thicker than average cock. It was already hard and wet with precum. I asked him if he has cleaned up his boyhole as I told him. And he confirmed that with a nod and big grin. So I turned him around, made him bent and exposed his boyhole to me. It was smooth shaven, clean and smelled alright. This hungry boy prepared well I thought. I spit into his hole and then had one of my finger played around his hole, before pressing it in a little. There was resistance, so my other hand then reached out to his nipple and played it. It helped him to relax his boyhole a little. I could have pressed my finger further but I changed my plan and attacked his hole with my tongue instead. Immediately he hissed and moaned in pleasure. And when my tongue pressed into his hole, his moan turned louder. I slurped and licked away, occasionally alternating with one or two fingers. Then I noticed his legs trembled and turned weak, so I moved him to the bed instead. He lied on his back and I pushed his legs up. He grabbed and held his legs, allowing me to have full access to his hole. I continued the rimming business for a good ten minutes. Then I removed my briefs, inched towards his head, and positioned my hard cock in front of him. He immediately grabbed it with both his hands, before putting it into his hungry mouth. He was definitely still a noob, I had to tell him a couple of times to watch his teeth. For a few times he did well, swallowing my whole cuck and sucked it like a vacuum cleaner. I got him to move down a bit so that he lied flat on the bed, and I turned to face his hole. We were in 69 and apparently, he knew very well how to do it. Of course, he did a sloppy job at it because he had to keep stopping to moan as I rimmed his boyhole. This time though, I alternated the rimming with three fingers. He probably didn’t even realize there were three fingers but he received it quite well. Another ten minutes passed, I could have gone longer to make sure he’s totally high, but he finally popped the question “Do you want to fuck me?”. I asked him again to be sure, and he was doubly sure. So I reached out to my supply bag, took out a box of condoms and a small tube of lube and sort of threw them onto the bed, near him. He grabbed the box of condom, remove the plastic wrapper, got one piece out, and tore it open. As he approached my cock, he cheekily said that he was being a good bottom by serving his top. I laughed at that corny comment. He continued jerking off my cock after putting on the condom, and I squirted generous amount of lube onto my hand. Then he instinctively lied on his back, exposing his boyhole for me again. I took a couple of minutes to finger his hole with the lube, making sure that it would be well lubricated. There is no such thing as over-lubricated so I applied even more lube directly onto his hole. I needed to make sure that his virgin experience would not be traumatizing. After making sure he was ready, I positioned my cock in front of his hole. I told him that I was going in, and he rested his head on the pillow, closed his eyes, and took a deep breath. As my cock pressed in, I played with his nipples at the same time. He was probably quite relaxed, as his boyhole muscle didn’t resist much. However as I pushed in more, beyond my cock head, he grimaced a little. He took another deep breath and then he looked relaxed again. I decided to stay still first, then bent down to lick his nipples. As he moaned in pleasure, I concurrently pressed in further. It took almost ten minutes to finally got my whole cock in, but I think it was worth it as he seemed to enjoy the process. The next thing, I kissed him while slowly drilling him. He loved it so much, turning me to hug him while continuing the fuck. He moaned and groaned softly. Five minutes on, and he told me to stay still. Then he told me softly that he felt like shitting, lol… I told him it was normal to feel wanting to shit for beginner bottom. I could tell that he was still worried despite my assurance but he didn’t want to disappoint me so he let me continue. The fuck in missionary continued for ten minutes before his cock suddenly squirted out his cum when I gave it just two strokes, lol… He was clearly quite embarrassed to cum so quickly and unexpectedly. He told me that I could keep fucking him but every tops should know that bottoms don’t feel good to be kept fucked after cumming. So I told him it was fine, and we could take a short break and I could always fuck him more later. I gave him a kiss on his lips, withdrew my cock, and told him to wash up first.
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