Recollection (II)

Jez had been texting me for a couple of days after our last meeting. Our chat often became dirty talk, couldn't be helped because he's one horny young boy. It turned out that he had two anal sex experiences so far, he was top in both times. I immediately knew then that he wanted to try the other role, but he was too shy to ask directly. He wondered how those bottoms felt when being fucked by him, how much pleasure in being fucked, would it be painful, how to get hard while being fucked, etc etc. But I had never been a bottom at that point so I had no answer for him.

When one day he told me he missed my cock, I decided to take a day off from work and asked him to come down to my house. And yeah, he couldn't get more excited. He arrived right on time, it was 10 in the morning. And he looked just like a morning sunshine boy, with that wide smile across his face. We had a bit of small talk but our hormones simply took over quickly. Before long, we were busy making out on my bed. He was a good kisser, no doubt. Although we were fully clothed, it was obvious that both of us had a huge hard on down there. Jez' hand slipped in under my shirt and caressed my abs before making its way to my nipples. There, his fingers skillfully teased my nipples, circling around them, lightly touching, then pinching. When I finally removed my shirt, he immediately buried his face on my pecs and sucked on my nipples. While he did so, I pulled up his shirt and played with his nipples. We both groaned softly. When he retreated for a while to take off his shirt, I removed my shorts and rewarded him with my meat. He excitedly grabbed it and started touching it around, his eyes fixed, as if he was worshiping my cock. He swiftly removed his bermudas and briefs and then on his fours, swallowed my cock whole. He slurped and sucked on it like a lollipop and I was just enjoying the pleasure his tongue gave. When he momentarily stopped with my cock inside his mouth, I thrust my hip up and down, fucking his mouth. He seemed to enjoy that a lot, his one hand pinching his nipples while his other hand stroking his own hard cock. We spent a long time with the foreplay, probably close to an hour, when I realized that he was touching his own hole while sucking my cock. I pulled up his head, looked him in his eyes and asked him "What do you want today ?". He sheepishly smiled and asked "Can you fuck me ?". I asked him if this was his first time and he nodded. I asked him again if he was really ready and he nodded again. So I got up to grab my kit, a bottle of lube and a couple of condoms. Then lied down on bed again, this time I motioned him to turn around so that we were in 69 position. He continued sucking me while I wet his hole with the lube. Then my point finger slowly went it. He let out a soft moan, his hole tightened, resisting the entry. I told him to just relax and slowly pushed in further. When the whole finger went in, I slowly fingered him, testing his reaction. He didn't make much noise and just continued on sucking. So I continued fingering for a while before my middle finger joined in. I wasn't sure whether he didn't realize or he got used to my fingers but he didn't make much noise still. So the third finger joined in and then he let out a louder moan. I asked him if he was okay, and he nodded. And then finally I asked him if he's ready, and he said yes.

I got up and told him to flip so that he lied on his back. I put down a towel beneath his lower half, then put on the rubber and lubed it up. He looked at all my actions in excitement and when I positioned myself in front of his hole, he instinctively lifted up his legs and exposed his virgin hole. I fingered him a little more, before placing my cock on the entry. "I'm going in", I said and then he took a deep breath and closed his eyes. Despite loosening with three fingers, it was still pretty tight and the initial entry met with much resistance. I poured more lube, then moved forward and whispered to him to relax, then kissed him and sucked on his nipples. That worked and I managed to press on and finally half of my cock disappeared. Then his face suddenly contorted with pain, and he tried to push me away, reluctantly. I maintained my position and kissed him instead, my cock stayed still. When his hole finally stopped resisting, I asked him if it's still painful. He smiled at me and I took it as a cue to go deeper. It took fifteen minutes for my cock to finally be fully inside him and when it did, Jez let out a heavy moan. I slowly pulled out and pushed in to let him get used to my cock. Although he moaned softly, I noticed that his cock had gone entirely soft. Honestly I was a bit lost at that time, I wasn't sure whether to continue and picked up my pace or stayed that way. Until he mumbled "Fuck me please". And I hesitated no further and began drilling his hole, still slowly but deep. I moved to hug him and kissed him while my cock slide in and out of his sweet hole. Then I felt something wet on my abs. When I got up, I saw his cock went back to semihard and massive precum leaked onto his abs. Then he said "Harder". So I lifted up his legs and placed them against my shoulder. I hold on both his legs and began thrusting rapidly. Each thrust slammed against his butt cheek and I was rewarded with loud moans, almost like screams. I reckoned that he was game for anything then so I flipped him so that he was on all fours and began impaling him mercilessly. My cock went in deeper in this position and that must have done good to Jez because his cock went rock hard, swinging back and forth on each pounding. I then pushed him down so that he lied flat on bed and continued drilling him. He didn't seem to like it, maybe because my cock couldn't get in much so he flipped to his side this time round.  I entered him from behind, my body was parallel to his, with his upper leg lifted to allow me accessing his hole deeper. I fondled with his pecs and nipples while kissing his neck. He went crazy with that. He finally asked me if I was about to cum and I said I was close. He said "Me too. Fuck me harder". So I gave it to him, I slammed fuck him, hardest ever, while he was jerking off his own cock. Then the scream "I'm cumming, I'm cumming, ah... ah... ah !!!", followed by streams and streams of cum flying across the bed, landed on the bedsheet (damn). As he cummed, his ass clenched my cock tight and I couldn't resist anymore. I soon came too, in him. We rested for a while to catch our breath, I hugged him from behind while he held my arms. I asked him how it felt and he said it was amazing. Now he knew what those bottoms felt when he fucked them. He said it was painful and weird in the beginning, the shitting feeling. But as soon as the pain went away and I started drilling him, he said the feeling of his hole being filled and rubbed against was just awesome. And when I pounded him deep, the pleasure was just amazing. But when I asked him if he preferred to be top or bottom, he said he still preferred being top, lol...

Recollection (I)

I received a message on one of the app recently, it was from someone familiar. He was back in Singapore for a medium-term stay. Several messages later, the conversation turned steamy and no prize in guessing where we ended. Instead of writing about our last hook-up, my mind wandered to the past where we first met and subsequently.

It started about four years ago. I went in to IRC on one lazy Friday evening. Couldn't recall exactly how it progressed but I chatted with this young chap who had just finished his NS. We chatted rather mildly, no mention about sex whatsoever. We exchanged picture and I saw a rather cute nerdy boy with thick framed glasses. Despite the nerdy look, I could tell a reasonably toned body behind the shirt. He asked me if I was keen to meet for a dinner on the next day, which I couldn't refuse. He gave me his name, Jez.

Jez was a very pleasant boy to be with. Cute, bubbly, irresistible laugh, and quite intelligent. He finished his NS three weeks ago, and waiting for his application to a number of universities. He was still rather closeted, so he took this free time to explore the scene around. He chatted with a number of guys but I was the first one he met, how amusing. At one point, he told me that I look very familiar. That actually set me thinking, indeed he also look familiar to me. But my mind couldn't figure out why. We decided to watch a movie since we clicked quite well. The movie must have been a lousy one because I couldn't remember what that was. But what I remembered clearly was he held my hands and towards the end of the movie, hugged me. Then I knew why he chose the last row seat. We bid our goodbyes at the MRT station as we were heading opposite direction.

We met again the following week for the same thing, dinner and movie. He got a bit more bold during this time, he touched and caressed my chest during the movie. Then his hand slipped under my shirt and roam around my abs. I stopped him after a while, fearing someone will notice. On our way back, he asked me if he could drop by my place. Damn, this boy was horny. But I told him that my parents are at home so it was not quite possible. He was visibly sad. Then he started asking me about where my house is and that was when it got clearer how we found each other familiar. It turned out that he is actually my cousin (our mothers are sisters). I had seen him when he was in his early teens but we had not seen each other again as our families drifted apart due to some conflicts. But amazingly he could still remember my address. Despite that, bringing him to my place openly was still not an option. Which then reminded me of my office. Very risky but I reckoned that no one should be around at this time. And it's not so far. He didn't mind, more like excited in fact.

It was pitch dark, it took me a while to move around and finally reached a corner where I thought shouldn't be too noticeable with the lights on. This corner was a sitting area actually, with a few sofas and a coffee table. As soon as the lights were on, Jez pulled me down to the sofa and started making out fiercely. His wet lips were so succulent and his tongue was dancing in my mouth. For a closeted boy, he sure was a good kisser. His hands were busy groping my chest during the kiss and it didn't take long for me to let him pulled up my shirt and exposed my upper body. He looked happy like a little kid upon seeing my body. He pulled up his shirt too, revealing a lean toned body, firm but not very big pecs, flat abs and dark chocolate nipples.

His hands played with my nipples for a while before his mouth started attacking one of my nipples. I stroked his hair while he was busy sucking my nipples like a baby. His other hand was down on my crotch, feeling my cock getting harder. I pushed him away, took off my short and brief, and he did the same. While my cock was fully hard, his cock was just semihard, uncut and covered with foreskin, around 5" of meat hanging down. I pulled him towards me again, holding his head, kissed him tenderly then whispered "Let's just keep it to oral for tonight, ok ?". He nodded in agreement, and then began busying himself pleasuring my cock. Again he surprised me. For a closeted boy, he sure was a good sucker too. His tongue skilfully licked the underside of my cock while it was inside his mouth. And his mouth was like a suction cup, everytime it left my cock, it sent waves of pleasures onto my whole body. His one hand was jerking his own cock while another hand was fingering his own hole. As he was such a good boy, I couldn't bear to let him do all the work and returned his favor. I pushed his head away, told him to switch position. When he did, then I finally got a good look at his cock. I was in awe seeing his cock. I honestly think it is a very beautiful cock. It is probably around 7" in length and thicker than average. But the impressive part is not about the size. It's very straight and very hard, veiny, and the foreskin is just enough to expose half of the head. And when the skin is pulled back, it displays a large bulbous mushroom pink head. I don't suck much but I couldn't resist putting Jez' meat into my mouth. Either because I'm inexperienced in sucking or because his cock was too large, my jaws were aching after a short while. He somewhat noticed that and asked me to switch again, all with that smile never leaving his face. He continued sucking for a good ten minutes until I had to ask him where he wanted me to cum. He didn't answer but his tongue service got faster and harder. I couldn't hold on and finally shot directly into his throat while my cock was in his mouth. He choked a little after a few sprays, but he recovered like a pro and swallowed my cum. He continued by kissing me while jerking off his cock. Few minutes later, he grunted and I felt warm liqued sprayed onto my abs. He collapsed on top of me afterwards and stayed there, breathless. After he regained his composure, he stood up, collected his own cum on my abs and his abs with his fingers, and licked them clean. Then he flashed his boyish smile again. That was the start of our journey.