I recommend reading “The Joys of Penetration Part 1” before reading Part 2.
Marty, my childhood friend, had just been the recipient of the first blow-job I had ever given. As I was reveling in the euphoria of the feeling of control the act had given me, Marty made it clear that my initiation into the joys of penetration was only half over. But first he wanted to return the pleasure I had just given him, and had started stroking my half-mast erection back to standard in preparation. Deciding that we were both wearing too many clothes for the occasion, Marty quickly stripped to nothing before taking the liberty of relieving me of my slacks and briefs. “Now I’ve got some room to work,” he said, as he lowered his mouth to my waiting organ.
Just as I had done to him, Marty’s first assault was to tongue the head as he stroked my length. But, as he began to replicate the up and down that I had performed, I noticed that he was leaving behind a lot more saliva than I had, so that it was soon soaking my balls and running down to the crack of my ass. Just as I began to wonder why, I felt a probing, first at my perineum, and then at my sphincter. Lubing his index finger with his spit, Marty slowing began inserting the digit into my tight brown eye.
At first there was this feeling of pressure, and then suddenly the tip slipped past the outer ring of muscle. As Marty’s mouth continued to minister to my member, the copious amounts of saliva served to keep his finger well lubed. Soon his finger was moving in and out as if we had been doing this for years, and the slightly unpleasant feeling had turned to one of sensuousness. Meanwhile, the tongue lashing and suction being applied to my dick was bringing me closer and closer to climax.
Suddenly, and with amazing coordination and dexterity, Marty did two things at once: he twisted his finger so that it was suddenly massaging my prostate, while at the same time taking the entire length of my erection in one fell swoop so that the head actually became lodged in his throat. This combination of sensations was so intense that I immediately lost my load. As my balls and sphincter spasmed through my orgasm, I could feel my asshole squeezing Marty’s finger still buried within. I don’t think I ever had as strong an ejaculation as he had just elicited.
As we both sat there panting on the love seat, trying to catch our breaths, I asked if that had been the second half of the lesson. “Not quite,” Marty responded, “but we’re definitely moving in the right direction.” At that, Marty decided that it was time to move into the bedroom. He pulled back the covers on the king-size bed as I took off my shirt, the sole article of clothing that had remained. “I’m a little hungry and thirsty,” he said. “I could eat,” I called out, as I went into the bathroom to take my usual post-cum pee. Finishing that, I took a look at myself in the mirror. I looked happy. I looked relaxed. I looked like someone ready to learn the rest of what would be revealed.
When I came out of the bathroom, I heard Marty ordering an ante-pasta salad with vinegar and olive oil on the side from room service. As we lay on the bed waiting for the order to arrive, we sipped more wine, neither speaking a word. When the order finally came, Marty was considerate enough to keep the server out in the ante-room as he signed the bill and the food was arranged on a rolling table. After the server left, we sat at the table in big terry hotel robes as we ate, both trying to ignore the undercurrent of sexual tension. We had almost finished when Marty said, “Don’t finish off all of the olive oil. We’re going to need some for the rest of the lesson.” Then he stood, removed his robe, and strode to the bed, carrying the cruet of oil. I followed, losing my robe as well.
Marty stretched out on the bed on his back. “For this next part,” he said, “I will need to be very hard. Are you ready for the next step?” “Yes,” I replied. “Good, then I want you to lube my cock with the olive oil and bring me to the edge.” Well, while it had been decades since I had last beat Marty’s meat, this part would be easy. The olive oil had an interesting feel when stroked up and down his now glistening shaft, especially when it mixed with the pre-cum that began to ooze from his slit.
I sat alongside, facing him so that I could look into his face and judge his level of excitement. When it was clear to me that Marty was as hard as he was going to get without actually erupting in orgasm, he told me to swing across so that we were in a sixty-nine position, but under no circumstances was I to do anything other than hold his cock tightly at the base. I did so, and soon felt Marty shove a finger back into my anus, this time lubricated with the olive oil. The insertion was easier this time, but he kept adding more and more oil, and then another finger, and then another. As he moved them around, I could sense that he wasn’t finger-fucking my ass, he was preparing it for something bigger.
Just as it began to dawn on me what that was, he slipped out from under me and came around from behind. Before I had a chance to react, the head of his prick was pushing up against the opening to my virgin ass. I was about to experience the second part of the lesson.
“Relax,” he said. “Don’t try to help, just let it happen.” And so saying, he slowly nudged the tip of his oiled cock past the outer muscles. The olive oil was slick, but thin enough that I could feel every contour of his helmet as it slipped in, so that I knew when the coronal edge was past the closure. “Okay,” he said, “now comes the part that feels a little strange at first. Just stay relaxed and go with it.” With that, Marty slowly pushed the rest of his girth into my bowels, until he was up against my asscheeks.
“How is it?” he asked. “Different”, I admitted, “but not bad. There is this feeling of fullness.” “Give it a minute, let your asshole get used to the width. Then we’ll move on.” So I did, and in a minute or so it was almost as if I had a dick in my ass every day. “I think I’m ready,” I said. “Okay,” he came back, and pulled his dick about halfway out. “Now how does it feel?” “Like you took something away,” I moaned. “Do you want it back in?” he asked. “Yes!” I cried out. “Okay then,” he said, “let’s have some fun.”
And fun it was. Grasping my hips, Marty began sawing in and out of my nether region, fast, slow, deep, shallow, hard, gentle. Just like the blowjob I had recently bestowed, he was possessing me once again in the most intimate of ways. Yet, this time he was in control, and I could sense that this time it was as much for my pleasure as his. So I let him take me, possess me, penetrate me. It was as if I felt every bump and vein in his hardness as it passed back and forth over the ring surrounding my opening, the head of his hardness massaging the inner walls of my tract as it probed my depths. And when it was time for his end, I once again felt the sudden increase in girth before I felt the pulsing and twitching of his shaft that preceded the hot liquid he was depositing deep into my rectum.
Marty draped himself over my back as he caught his breath. Then, playfully slapping my ass, he withdrew and spun me onto my back. Lubing my now rock hard prick with what was left of the olive oil, he quickly and forcefully jacked me to another amazing cum, white ropes shooting up and out onto the bed sheets as his recently deposited load seeped out from between my cheeks.
“That, grasshopper,” he grinned, “is lesson number two.” “I think I owe Phyllis an apology, “ I said. Still grinning, Marty said, “Yeah, you do. But man, stay away from that dildo!”