Night Shift with Pilot

By Drhank

Published on Jul 14, 2020

Gay

I slept like a baby that night, nestled up against Steve's warm body and when I stirred awake the next morning we were still in the same position spooned together. This morning though I could feel the hardness of his morning wood pressed up against my asscrack. It felt great, and I nestled back into him, grinding my ass against his cock. Steve pulled me closer to him, and nuzzled the back of my neck. "I need a piece of that ass" he whispered in my ear. I ground against him even harder in response.

First things first though, I had to pee so I reluctantly got up to go to the bathroom, reaching back with my hand to give his dick a squeeze first. Steve had to pee too, and while he did I waited for him in anticipation, facedown on the bed with my legs spread apart. "God, what a beautiful sight!" He said as he kneeled on the bed behind me. He ran his hands around my back, kneading my shoulders briefly, before traveling south to my ass. This wasn't a massage session though, Steve had other ideas. He spread my cheeks apart and I could feel the tentative touch of his tongue exploring my crack. I wanted more of that! To give him easy access to that untouched sensitive area I raised myself to my elbows and knees, legs spread apart. I felt so vulnerable in this position, giving someone access to this most private area of my body.

Steve responded as I had hoped, licking down past my perineum to the base of my balls. I could feel the stubble on his face as he nuzzled in and attacked my ass with his tongue. Last night he had blown my mind by rimming me a bit in the shower. This was even better, because with me on my elbows and knees he had much better access. He took his time, moving slowly back and forth between my balls and my rosebud, and very soon I was as hard as I had ever been, with another drop of precum dripping from my uncut cock. Steve must have sensed it somehow, because he reached his hand around and stroked my cock just once, making me groan with pleasure.

Right now though, it was all about my asshole and Steve slowly worked in first one finger, then two, using my own precum as lube. From time to time he would reach around to my dick and gather more to spread around, licking it from my loosening hole before adding more with his fingers. I consciously relaxed my sphincter, secure in the knowledge that I would be able to take his cock. After all, he had fucked me once before, although that was years ago by now. Nothing had been up there since except for my own fingers, and it was much better feeling Steve's fingers inside me, searching around and massaging my prostate.

Steve reached over to the nightstand, and soon I felt cold drops of lube from a bottle dripping onto my crack. "I want to make sure this is really comfortable for you" he said, working it in and stretching out my rosebud. Then there was the moment of anticipation while he rolled on the condom and lubed his dick, and the inevitable pressure of his helmet shaped head against my hole. "Breathe,college boy" he reminded me, so I took a deep breath and as I inhaled I felt my hole pop open and his tip was inside me. He knew that my ass was not used to this, so we just held our position there for a while, breathing together while he gently increased his pressure. Soon his rock hard cock was sliding deep inside me, and I could feel its heat buried up to the hilt, balls resting against me. I reached way back between his legs and held them in my hand. I felt them give a little jump as I touched them but soon they pulled back out of my reach as he withdrew. He pulled almost all the way out. I could feel the helmet of his dickhead stretching open my sphincter before he plunged back in in a single slow stroke which took my breath away.

I pressed back against him as he plunged in, and this time he did not wait before pulling back for another stroke. That was how it was for a while... steadily pulling almost out before immediately reversing and relentlessly thrusting all the way back in until he was balls deep inside me. On each thrust his hard cockhead rubbed against my prostate, making my dick jump. By now I was leaking a steady stream of precum. I pushed back against him, matching him thrust for thrust, and grinding myself against him as I massaged my prostate against his rod.

Steve wrapped his arms around my chest, pulling me into an upright position and nuzzling my neck as he continued his thrusting. Now his strokes were a little shorter, but also faster as he gently pinched my erect nipples. My tits are extremely sensitive, and when he touched them it was like an electric shock, but he didn't let me pull away as he plunged into my ass. This was not to be a slow leisurely fuck. We both had been anticipating this for years, and soon he picked up the pace until he was pounding relentlessly into me. I felt my asshole stretch as he became even bigger inside me, and I heard him panting in my ear as he reached the point of no return.

His arms tightened around me as he pulled me toward him, and at the same time I ground my ass back on him meeting his every thrust. My body started shaking as I felt him unload inside me. I could feel each lava hot blast he shot, filling me up but making me yearn for more.

I fell forward onto the bed, the full weight of Steve's body resting on top of me while his throbbing cock was still buried balls deep. What a satisfying sensation to have him covering me like that. I was not done yet though, and as we lay with him on top of me I started grinding myself back on his still hard cock. Too soon the sensation became too much for Steve, and he gave a twitch and pulled out of me leaving an empty feeling inside. We still lay together like that for a while though, him on top of me as I could feel his slowly softening cock against my skin. It felt too good to move.

"Now it is time to take care of you" Steve whispered in my ear. He wrapped his arms around me, and he held me tightly against himself as he rolled over onto his back. I was now laying face up on top of him, my head resting on his firm shoulder. With his hands he began exploring my body, fingertips just grazing over the skin of my abdomen giving me goosebumps. He went back to my nipples, barely grazing them until I was squirming on top of him. Then finally, mercifully, one hand travelled slowly all the way down to my cock. "Spot seems especially happy this morning!" He said, feeling the precum leaking from under my foreskin, and lubing up his finger. He slid in underneath the foreskin, and he rubbed all around the head stopping at the frenulum, that sensitive spot at the base of the helmet. The effect was electric: My body had never felt more alive. "I bet you could make me cum by just doing that" I challenged him. "Let's see!" He replied. He grasped my full shaft in his hand and gave me a single long downward stoke, pulling the skin off my head with it and spreading around my juices. Then he pulled it back up over the crown again and slid his finger back underneath the hood. He started to gently massage a small circle around the magic spot. With his other hand, he reached down and caressed my balls sending me into spasms of pleasure.

The buildup was slow but intense as he edged me on, relentlessly moving me toward orgasm. Higher and higher he took me, until at last I exploded over the top. The thing about slow relentless orgasms like this is that they last much longer than the quick jerk ones. The thrill of ecstasy goes on and on: It is like launching into the air and soaring on the thermals in a glider, rather than jumping out of an aeroplane and parachuting to the ground. Steve continued rubbing circles on that same spot as I shot out blast after blast of come. It seemed like it went on for minutes before I came down from my high, and we just lay there like that for a while, my balls cupped in one of his hands and his other finger resting in that same spot, underneath the hood of my foreskin.

All good things come to an end though, and eventually it was time to get up. We took another shower together, and continued to explore each other's bodies, but we were both spent.

As we sat at breakfast in the hotel restaurant, our conversation flowed easily just like old friends. He told me that Minneapolis was not on his normal route, but because it was the main hub of the airline he should be able to get back from time to time. "I hope we can get together again next time you are in town." I told him. "No doubt about that." He replied. I am not going to let it go this long again. I will let you know when I can get back to the city." He gave me his number, and I told him I would be careful about calling it to avoid his wife getting suspicious. "Don't worry too much about that," he told me. "Tell her the truth, that we are old friends who met years ago in Montana. Just leave out the part about how we got to know each other, and all the other juicy bits!" I figured that was the best thing to say to my friends at school too, who would inevitably wonder where I had been last night. I would just tell them that I met up with an old friend from home, and we talked so late into the night that I ended up crashing at his place.

Steve and I did see each other again from time to time, but that is perhaps another story.

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