"Please lift your legs up and hold your knees under your chin," he instructed. I did exactly as he asked, exposing my asshole to what I knew was coming.
He squeezed a generous amount of lube into the fingertips of his left hand and placed the tube down on the bedside table. With his right hand he grabbed my balls and pulled them up and to the side, holding them there firmly. With his left, he smeared the big dollop of lube onto my asshole and all around my ass. He began giving me the same treatment he had given me earlier in the shower, dragging his slippery finger from my tailbone to my scrotum, allowing it to dip into my ass with each pass. Again, after a few minutes of this, he eventually sank one finger deep into me. It was cold and I gasped.
"Let me know if anything hurts," he said. I nodded as he worked the finger in and out, and around in circles. His other hand now grasped both my balls and my cock rather tightly, firmly tugging and pulling up towards the ceiling. He released my balls from his grip, moving the palm of his hand up to grasp the shaft of my cock. He would stretch me tight, pulling the skin of my uncircumcised cock up over its head, hold that position for a couple of seconds. He would then bend my cock up flat on my stomach, then hold it there for a couple of seconds. Then he would quickly bend it town towards my knees, almost a full 180 degrees, until it felt like it was going to break off. He kept up this series of manipulations for quite a while, the whole time keeping a warm finger deep up my ass, sliding it slowly in and out and moving it around in circles. After a few minutes of working me like this, he slipped his finger out and bent my cock up flat on my stomach. "Keep you knees up, he said. He reached in his overnight bag, and removed a black rubbery butt plug. He squeezed another big glob of lube into his hand and coated the plug with it.
"I’m going to ease this into you. I will do it very slowly, and it will feel very good up until we get to the widest part. It might hurt for just a second, but after the biggest part passes your anus, any pain will go away and you’ll begin to get used to the feeling. Ready?"
He put the tip at my ass and began to ease it in and out, and just as he said, when the widest part stretched my ass, a sharp pain stuck me. I gasped again, clinching my teeth, but just as soon as the pain came it began to dissipate. The plug was in and he was gently tugging at its base. I felt completely filled and warm.
"Now stand up and face me, "he said. I stood facing him, arms again at my side, with the plug stuffing my ass. I had to stand with my legs slightly apart to accommodate my visitor. The feeling of being so filled was amazing. He sat on the edge of the bed with his legs slightly spread, his own cock hard and twitching.
"I want you to kneel down in front of me, between my legs, and give me a blow job. I am not going to give you any instructions, I want you to just do what feels natural."
I proceeded to kneel down and do as instructed. I dove in, grasped his hard cock, and sucked its plump purplish head into my wet mouth. I gently tugged and milked his shaft with one hand, massaged his balls with the other, slurped, sucked, and licked all around the head of his cock. He was beginning to leak pre-cum – it tasted musky, salty, and quite frankly kind of gross. I guess I’m not a cum-eater. His breathing became deeper and he let out a couple of soft moans. I tried to take as much of his cock into my mouth as I could; it was almost too wide and almost made me gag. Every couple of pulls I bent his cock up on his stomach and gave his balls a good wet lapping, gently nibbling his scrotum and sucking each individual ball into my mouth.
"Ahh, very nice," he said after what seemed like an eternity. My mouth was a getting a little sore, but I continued, wanting to please him as best I could. I had almost forgotten about the plug up my ass – it was feeling very comfortable by this point – I was only aware of its filling presence when I shifted weight between legs.
"You had better stop now before I cum," he said when I increased the pace of my jerking. "Why don’t we trade positions now. Please sit where I am, lie down on your back, and pull your knees up to your chin like you did before." I did as instructed, pulling my knees up on my chest and waiting for what was to come next. He stood before me with an enormously erect penis – it was shiny and slick from my saliva and a couple of big swollen veins wrapped it. He reached into his bag, pulled out a condom, and put it on. He then picked up the tube of lube and turned to me. He grabbed the end of the black rubber plug in my ass, gently pulled at it, and instructed me to gently push. It popped right out with a squishy sound, he placed it on the bed next to me. "Keep your legs up," he said. He proceeded to smear another generous dollop of lube on my asshole, dipping his fingertips into me with each pass just as he had done in the shower. Next he smeared the tip of his cock with lube, faced me standing, and placed the head of his cock on my asshole.
"I’m going to very gently push, and I need you to concentrate on relaxing your ass.," he said in a very calm voice. When I first push in, there will probably be a sharp pain, just like the plug, but it will pass shortly. Are you ready?"
No sooner had I signaled my approval with a quick nod, he began to push. Nothing, nothing, nothing, then, BAM! Just as he had said, a sharp pain exploded as the head of his cock popped in. I gasped and cringed, feeling like my asshole had been torn.
"Relax, relax, the pain will pass," he said in a reassuring tone. And pass it did, almost instantly. I concentrated on relaxing, and I was suddenly filled with a warm tingling sensation all around my ass. I could feel my own cock hardening from the excitement of being fucked for the first time. I sighed and moaned my approval as he continued to slowly push the entire length of his cock into me. When I felt his pubic hair tickling my own balls I knew he was almost all the way in. At this point he slowly began to reverse his trajectory, gently pulling almost entirely out, then slowly easing the entire length of his cock back into my well-lubricated rectum. He fucked me like this for I don’t know how long. As my ass relaxed and got used to his cock’s presence, it glided in and out easier and easier. A couple of times on his back swing he popped entirely out of my ass, only to gently plunge back in without any resistance or pain on my end. He reached down and began to pull at my own cock as his pace increased slightly.
"I’m very close to cumming," he grunted as he fucked me at a slightly faster pace. My ass and rectum was so lubed up and slippery, he could pump in and out of me with vigorous, full strokes. I’d never felt anything like it – it was wonderfully warm and filling. He gripped and pulled on my own cock even tighter, tugging it in unison with his thrusts. My own orgasm struck with an intense flash, like knocking your head into a wall, without the gradual intensifying tingle that accompanies most orgasms. My ass and thighs bucked with muscular convulsions as the orgasm blazed, squeezing and milking his cock, as thick and sticky ropes of my warm cum spattered all over my stomach and chest. This must have triggered his orgasm as well, he grunted and pumped hard a couple of times, finally stopping when his pubic hair was once again pressing firmly against my scrotum. I could feel his own cock twitching and throbbing as his condom quickly filled with his warm cum; his breathing was deep and quick, his belly and chest glistened with a layer of perspiration from the workout. He stayed inside me as his cock softened, he rubbed his hands all over my belly and chest, working my own come into my skin.
I spent the next couple of hours with him in his room, either on my knees or on my back. I gave him one more blowjob (he came on my face) and he fucked me in the ass two more times – he must have been incredibly turned on to be able to keep going as much as he did. He ended up giving me one blowjob and had me jerk off twice while he sat and watched. I finally went back to my room with a loose, slippery asshole, the hints of yet another hard-on, and a big smile on my face.