Finally, here is the last chapter of this story:
I havent always felt this way, but over time I have become much more confident in bed. With age I have learned how to be a considerate lover and how to avoid most of the complications of being well-endowed, and my self-doubts have lessened dramatically. In an odd way, however, even though I was performing about as well as I ever had, my adventure with Brady was making me very self-conscious again. I so wanted to make his first experience not just enjoyable, but unforgettable. As I was helping him prepare to accommodate me, it felt like juggling - there was so much going on. I was trying to conceal from Brady the complications of it all, and hoping that it all seemed as if it was flowing naturally.
I have grown comfortable with my various fuck-buddies, in part because it is nice to be past all the worry and fumbling. Knowing their likes and dislikes, even if things get a little routine sometimes or stay pretty tame, allows me to get on with the sex and not waste time on pointless insecurity: mine or theirs. I didnt have this with Brady yet. He was eager and seemed open to about anything, but I was still pretty hung-up in my head.
At that perfect moment, however, when Brady slid on all the way onto my willing erection I suddenly knew we were home free and everything clicked. I felt certain that even if this were all that came of the day, he would feel well served. That dissolved my worry. It was at that precise moment that I began to actually enjoy the experience myself. It dawned on me that I knew a few more bells and whistles that might just give us both an extra jolt, but Brady didnt even suspect they existed and if they didnt work, why, he never know what he missed. It was a cant-lose situation.
After a few moments of rapturous indulgence, Brady had begun to gently work himself up and down my dick, and I slowly began to thrust gently with his rhythm. He felt amazing. I began to let him ride all the way down my nine and a half inches. (Okay, so you caught me. I know I told Brady it was only eight, but it was for a good cause. I wanted to help him get over his fears about it. Some minor underestimation can convert skepticism to lust sometimes. It is all in the mind!) He loosened up with each pump, and before long he was able to slide down until he rested on my pubic bone, snugly against my balls, at the bottom of each stroke. He groaned, but his steadily increasing pace led me to believe what he was feeling was pleasure.
I took hold of him by his hips and gently eased him backward a couple of inches as he continued. With luck, I thought, Im going to find his prostate in a minute here. I adjusted the angle a couple of times, but the fact is that I was getting so swept up myself that I wasnt giving it that much effort. It was blissful and I was enjoying the hell out of it. Bradys sudden gasp on one fortunate stroke told me that I was hitting paydirt. I kept him centered for the same angle and went back a little deeper. This was it. He tilted his head back toward the ceiling and began moaning. That turned me on even more and I sped up a little but kept the pressure in exact the same spot. His back arched further and further and his head tipped so far that all I could see from below was his neck up to his Adams apple, where his pulse was perfectly visible pounding in his carotid arteries.
I felt like a god. I was so into the moment that it took a few seconds when he looked back down at me to register that tears were streaming down his face.
I was horrified. Oh, shit, I thought, Im doing to him exactly what had happened to me. I was so carried away with how great it felt to me that I hadnt even realized how much it must be hurting him. My mood crashed and I froze in mid-stroke. Oh, God, Brady. Im so sorry. Im sorry. I didnt mean for this to hurt.
You are so fing stupid, he gasped out with a teenaged sarcastic tone that told me he didnt mean it. It doesnt hurt. I never thought anything could feel so good. Im happy, man, he said as his lips spread into his now familiar smile. Then he reached down and grabbed fistfuls of chest hair with both hands causing me to startle from the shock of it. He pulled me up toward him by my hairy pecs and, with a voice an octave lower than Id ever heard him use, said, SO DONT STOP. Cmon. Go. Go. The tears had not slowed a bit even though he was grinning, but I took him at his word and started pumping against his prostate again. It was not even another half minute before I felt his ass grip down on me like a cockring adjusted one snap too tight. I knew he was going to cum, and I tipped my head up to get a good view as he violently jerked and his first shot launched completely over my head. Fuuuuuuuuuck, he growled out as he got off a second blast. It left a trail from my navel all the way up my chest and dripped off my left shoulder. It was only because I had deftly moved my head to the side at the last second that I didnt get a mouthful. Damn. Damn. Daaamn, he uttered as he shot again and again. I was completely covered with stripe after stripe of cum, when he finally slowed down and began to ooze slowly. And then to my surprise he collapsed forward onto me, and just lay there sobbing. He held me tight, his sperm bonding us together, as he heaved up and down from the force of his own crying.
Brady, are you alright, I asked as gently as I could while I held and comforted him.
He was quiet for a while until he calmed down. Im gonna be alright, arent I, he said, not asking a question. When hed gathered himself a bit, he sat upright again, me still completely hard in him. Im going to be able to find somebody to love, arent I, he said marveling at the discovery. I didnt know quite what to say. I dont know why Im feeling so overwhelmed like this, he said. From the day I figured out I was gay, Ive been worried it would mean I would always be lonely. I cant tell you what you just did for me. I feel so relieved. And then with a edge of wonder he said, Is it always like that? Jeeze, no wonder people like to fuck.
I laughed out loud. Id forgotten that he really didnt know. Im sorry to be the one to tell you, but it isnt really that good every time. This was very special. You are very special. But yes, Brady, you are going to be okay. A lot of times sex is like that, and it sure feels like love to me.
Then, as easily as if nothing had happened, he glanced down at me, nodded, and said, Well, as long as we are already sticky, we might as well just get on with it, and started slowly pumping himself up and down my dick again. It was a bit of a surprise that I had stayed hard, but damn that boy was tight and I am sure that helped. He seemed completely into the experience, and that helped me just luxuriate in the incredible feeling of his riding me. At first he was quietly intense, but after a bit he began to talk to me. Do you like that? How is my ass? Cmon, fuck me harder. I knew he was putting it on, but frankly I no longer cared. Id gotten him off twice today, and right then I was I was just indulging my own pleasure. His hot talk, however manufactured, was actually working for me. Are you getting closer? I want to feel you cum, he whispered hoarsely.
I was getting close. Before I had been distracted worrying about Bradys orgasm, but now I felt free to concentrate on my own, and I was getting there. I started edging closer and I warned him that it was going to happen before long with a few grunts, and an occasional, Yeah, that feels good. As I felt my balls tighten right up against the base of my cock I said, I am almost there.
To my complete surprise, on the next upstroke, Brady lifted himself completely off my pole and slid himself back onto my thighs. I want to see it, he explained excitedly. Without missing even a stroke, he reached down with his right hand, gripped my cock and with one quick upstroke slid the condom right off me. He quickly gripped the base of my unit with his left hand and squeezing tightly, pushed back down hard against my pubic bone. The with his right hand, now slick from the lube that had been on the condom, he took hold of my dick head and started stroking it furiously. Teenaged boys may not know much about fucking, but they are the worlds greatest experts on jacking. Brady knew exactly what he was doing. He added a slight twisting motion to the short strokes he was using on my knob job and in seconds I was bucking like a rodeo bronc. I started invoking the names of every deity I had ever heard.