The Enlightenment

I seldom look for new guys for hook-up recently as I have a steady pool of regulars and sometimes I have to disappoint them when I don't have enough time for them. So on the rare occasion that I turn on the gay app, I'm normally very detailed in checking the background to prevent wasting of time. That, however, was not the case on my last encounter a couple of weeks ago. His profile showed his well-developed pecs with light brown large nipples, and faintly-visible 4-pack abs. When he sent me his face pic, he turned out to be a cute nerdy chap with glasses. We set up the time and place, I happened to have place available in the evening that day.

He showed up in tight-fitting t-shirt that clearly showed his pecs and jeans, with crumpler sling bag. He is definitely cute. He was a little nervous at first so I gave him alcoholic drinks, which he took happily. We spent little time in the living room and then moved to my bedroom. The session began very slowly and mildly. We took quite a bit of time to just sit down on bed and chatting. He is a student in a local uni, just ended his exams so was quite free, and apparently quite new in the scene. I was partly concerned and partly excited after hearing that. So I'm facing a newbie, but he could be fun enough to try new things. At some point our conversation came to silence, and we were just looking at each other. Then the kissing came up next. He was certainly not a bad kisser for a newbie, I got quite a boner by making out with him. His hands were groping all over my body, slipping underneath my tanktop and played with my hard abs and nipples. Next he removed my tanktop and started licking my body, starting from my belly button, abs, pecs, armpits, and then nipples. As he did that, his hands were fondling my crotch and gradually lowered down my shorts. He continued by holding on my cock firmly and lightly stroking it. I was sitting on the bed while he was kneeling down during this time, so I decided to make myself comfortable on the bed. I lay down on the bed with my head resting on the pillows, spread open my legs and cue him with my eyes. He got it, and removed all his clothing before climbing up onto the bed, and on while on all fours, have his mouth serviced my cock. He did a very decent job at it, if not pretty good. I didn't feel his teeth, his tongue was slurping away, and the suction was just enough. I was super hard already by then, no doubt. He then moved up on top of me, offering his large nipples to me. It was not the very juicy type of nipples but they still look pretty nice. And he got pretty high having his nipples chewed on. Then he inched forward, raising his body higher, and offered his cock instead. His cock was pretty nice actually, probably about 15cm uncut cock with plenty of smooth foreskin to play. But the thing is, I was in my pure top mode so I declined sucking his cock. He was visibly disappointed, and immediately lay down on bed next to me.

Kind of awkward, so I pulled his hand over to my cock hoping that he will continue what he did. And well, he did actually. He went back to playing with my cock and bod again. As half of his body got on top of me, his lower half had become an easy access to me. My hand reached out to his perky butt, squeezed it and smacked on it. He let out a groan. Then I pushed forward to reach his hole. And suddenly he stopped licking my nipples and held my hand firmly. He looked up to me and said "I don't do anal". Damn, then I realized that I had not talked about that at all in the app. It turned out that he's not really into anal, and even if he does (he had only done twice he said), he would be the top. Things quickly turned into even more awkward then before, in fact there's a sense of blaming each other as we began saying "I thought you said". So at one point I said that we could stop there if he wasn't comfortable but I really needed a fuck. He actually had put on his briefs, when he hesitated, then turned around and said "Well, I guess I can try". Now that's awesome, I thought. He asked me to be very gentle on him, which I promised, and then he went to the bathroom to clean up his backside. I'm not sure if he know how to clean since he's not into anal, but I couldn't care since I was horny. He came back with nice-smelling butt, and we continued with making out. I flipped him to 69, and while he sucked my cock, I prepared his hole. I gave him a rimjob, something that I seldom do, since his butt smells nice. When his hole was thoroughly wet by my saliva, I spit some onto my finger and began pressing against his hole. It slowly went it, but he was giving too much resistance. So I poured some lube onto my finger, then started to work again. One of my hand then reached out to his nipples, tweaking and playing with it. He moaned, that's a good thing. The lube eased the entry well, once my whole index finger was in, he let out a groan. I asked him if he was okay, and he nodded without looking at me. Then I withdrew my index finger, and poured in a little more lube. Next I pressed both my index finger and middle finger against his hole. It was hard to enter again. I worked my way in so slowly again, easing in as he got more relaxed due to the nipple play. He let out another groan when both fingers were fully in. And then I began thrusting my fingers in and out of his hole to let him feel it. He didn't react much and continued playing with cock. The next attempt with three fingers became much easier, so  I thought it was time to use something else now. I asked him if he was ready, and he nodded again, this time while looking at me. He flashed a nervous smile, kind of cute in fact. I flipped him so that he lay on his back, then I placed a towel underneath his butt. He voluntarily lifted up his legs, and I poured even more lube onto his hole. I put on the rubber, poured some lube on it, and then inched forward to him. My cock was touching his hole, then I slowly pressed in. His hole was still very tight despite the fingerplay just now. It helped that my cock was so hard though, I could feel that it began to tear open the tight hole. He took a deep breath as my cock started to enter. Despite his best effort to remain calm, it was quite obvious that he began to uncomfortable as seen from his face. As I went in a little, his look quickly turned into a painful one. I thought I could press on, but he stopped me while grimacing and uttered that it was hurting. I leaned forward to kiss him, hoping that it would make him relax. Which worked, he let go of the clenching little by little. Few minutes later, he gave me green light to continue. The cycle then repeated. It took about 5 times slowly entering and staying still before my cock was fully in. I didn't immediately drill him afterwards, and instead I kept still to allow his hole get used to my cock. When I did try to start pumping him, he held me from doing that in fact and said "Just stay still first. Damn, this feels quite good".

So he was enjoying the feeling of having a hard cock inside his passage, but I need to pump so I started by very slow and short thrusting. He didn't resist and let out a soft moan instead. He closed his eyes, seemingly enjoying the pleasure. I gave him a slow and gentle fuck, nothing fanciful, I was simply sliding my cock in and out of his boyhole. It was a good thing because the friction was too great (i.e. pleasurable) due to his tight hole. Any faster or harder and I would cum too quickly. His cock that was limp when I first entered him slowly gained hardness. Within ten minutes after I started pumping him, his cock had become 3/4 erected. While pinching his nipples, I told him "Your cock is telling me that you're enjoying the fuck". He opened his eyes, looked down to his own cock and sheepishly replied "I didn't expect this at all. You really know how to fuck". Well, I have not even given you half of my fuck, boy. Another five minutes on, and I flipped him to his side now, pulled down one of his leg (the one on the lower side), and pulled up the other leg, resting against my shoulder. It's somewhat like in between missionary and spoon position. I could get slightly deeper in this position, and that seems to work well as he moans a little louder. I picked up my pace a little, anticipating for resistance but he didn't. So I gradually got faster and harder. I noticed that his cock went back to semihard, he probably hasn't gotten used to the quick and hard pounding yet. So I toned down and went back to the smooth and slow sliding moves instead. That did the trick and his cock went harder again. But damn, I needed to pound hard actually. So no choice, I continued doing that way which bored me a bit so I decided to let him do the work. I withdrew from him, moved to the back of the bed, and motioned him to come over. As I lay down on bed, he took the hint and position himself on top of me. This time my cock went into him immediately, but as he sat down on me, his face still showed a little painful look. He stayed still for thirty secs, took a deep breath, and then began rocking. Now by the time his rocking was in full force, I would never be able to guess that he was not into anal sex at first. With his eyes closed and mouth half-opened, his face clearly showed that he was enjoying every bit of pleasure he received. His cock, hard then, was bobbing up and down in the air without being touched. That lasted for about ten minutes, after which he said "I'm gonna cum soon, can you fuck me like the first time ?". So I obliged, and pushed him down onto the bed, lifted up his legs, and began drilling him. It wasn't a hard pounding still, but it was clearly enough for him. As he came closer, he began talking dirty. And then finally he muttered "I'm cumming", his hand reached out to his cock and jerked it hard, until thick creamy liquid sprayed all over his abs. I pumped harder into him, pulled out as I got close, removed the condom, and cummed onto his abs, mixing with his cum. I wiped the mixed cum with my fingers and then brought it over to his lips. He licked, rolled out his tongue and said it was salty. We rested for a while and he described the feeling he had during the fuck just now. He said that the first entry was so painful, as though his hole was ripped apart. But he endured, and then the pain slowly subsided. When my cock was fully inside him, he felt as though his hole was stimulated by the stretching alone. It wasn't a pleasure like having his cock jerked off, rather more subtle and widespread. He said that at some points his body shuddered uncontrollably because of the pleasure. I explained to him that it was because my cock was rubbing against his prostate. Apparently he had been fucked before, when he first came out to the circle. But apparently that guy did a lousy job and only cared about his own pleasure. When I asked him if he's going to become more bottom now, he said he would probably not go into anal so much yet still. As he left, he gave me a high note by saying that I really know how to fuck and that I did such a good job. One happy new customer left, lol...