I had been tutoring Carl for 4 months at this point. He had just turned 14. I was now a 19 year-old sophomore in college.
I was hired by his parents, after leaving a posting on the bulletin board of his school, the very school from which I myself had graduated just 2 years prior.
Carl didn't have much of an attention span, so usually after a solid hour of studying his mind would wander and his concentration would diminish. We would usually just talk; he was funny, and very grown up for his age, mentally anyway. His physique however was younger looking. He was probably 5'4", 115, and still hadn't blossomed. His voice
was just beginning to change, but was still rather high. He had brown hair that had grown past his eyebrows and ears, but not far enough to be considered long or shaggy.
I should also mention that I had always considered myself straight, and even had a girlfriend when this happened. The one exception in my past came when I was a junior in high school (wow, only 3 years ago...it feels like more). I had befriended a sophomore on my track team. I felt drawn to him, and had what I would have labeled a "non sexual crush." After hanging out for a few months, and spending the night at my house, one night we both started jerking off. Then it led to sucking each other (but never swallowing). After we had given each other head a few times, one night I began licking his dick, and slowly worked down to his butt. It smelled pretty awful I thought, but I kept doing it anyway. Girls smell bad too, but you just suck it up and be a man about it. After licking his hole for a bit, I stuck a finger in, and then tried sticking my dick in with no lube. I spat on my hand and rubbed it around on my dick, and managed to get about 2" into him. It hurt, I could tell, and he probably wanted me to stop, but it only took me about a minute to finish. We never talked about it, and shortly after that we never really hung out. We were both masculine guys, so no one had ever suspected or found out about our brief experiments.
Carl's parents didn't get home until late. In fact, I had never even met his father. This particular tutoring session was very brief before he started showing me things on youtube that he thought were hysterical. I humored him. Out of nowhere he asked "What does circumcised mean?" I was taken aback. I told him it was when the foreskin is cut from the penis, usually at birth. He asked what foreskin was, I explained. He smiled, then peeked under his shorts, pulling the elastic waist of his soccer shorts out to look at his junk. (I should mention that our tutoring fell after his soccer practice, and I would usually arrive at his place as he came back from practice, hair wet with sweat. I always took note of that).
"I still can't tell." He said. He rose to his knees (he had been sitting on the area rug in his tiny bedroom). He pulled down his shorts and briefs. I looked away, I think because I knew I didn't want to look away. Then he said "Just tell me. It's not a big deal." I looked back to see he was in fact circumcised. I told him.
"Are you circumcised?" He asked. "No," I said.
"Can I see? I just want to see."
"Uhhh..." I paused. I could tell I was smiling an idiotic smile that may as well have said "I really want to show you, yes."
I also quickly convinced myself that unlike my affected response, his request was innocent.
So I did it. I just pulled my jeans down. I was fairly toned, except in the stomach. I'm not fat, I don't even have a tiny gut, but the rest of me looks like I should have a six pack or something. Instead it's just flat. I had a chubby, but figured he couldn't tell.
"Whoa. It's weird looking," he said.
Without thinking I blurted out "Hey, stand up." He stood up. His penis started bobbing up slowly. "And turn around." He turned around. He looked slightly confused, but was eagerly compliant. His hip-less waist and butt cheeks were right in front of my face. I got on my knees and slouched a bit, and I pulled his cheeks apart. "What are you doing?" His tone
was playful and curious; he knew what I was doing but had to pretend, defensively, like this was not his idea.
"I want you to feel something really cool." I said. I inched my thumbs closer to his hole. I spread it, giving me the best view to his tiny little butthole. There was no more than 4 tiny, stray hairs surrounding his pink hole, which looked as small as his belly-button. He eased his butt closer to my face. I just breathed him in a bit. He was stinky, I assume from a
combination of taking a shit recently and running around at soccer practice. But his smell wasn't gross at all. It was
almost like beeswax, only a little dirtier smelling. I licked his hole with the tip of my tongue. He giggled and squirmed and said "Ew, that's gross." The next couple licks were flatter, using more of my tongue, and softer. He tasted good too. Salty and bitter. I told him to get onto his bed, so he did. As he moved I could see he was totally hard, no more than 4 and half inches. He laid flat on his back. I told him to turn over and to stick his butt up in the air.
I moved over to the bed and knelt on the floor, his ass spread over the edge. I licked him for another few minutes. He said it felt good. I was able to get more of my tongue inside, and stretched it around the rim to loosen him up. I knew now I wanted to put my penis into his little butt. His cheeks were flawless and pale. I could see the notches of his tailbone protruding at the base of his back, all knelt-over. I licked my index finger and wiggled it in a little. He gasped. I held it still, then pushed it forward. He clenched the blankets below him. I removed the finger, then worked my middle finger in the same way. This time I pushed deeper. After about a minute I almost had the entire finger up his bum. I held it there and wiggled the tip around deep inside him. He made some soft groaning noises. I took the finger out.
"Did you like that? I asked. "Uh-huh" he softly said. "Are you going to put it in my butt?" He asked. "Can I try?" He nodded. I asked him if he had any lotion and he replied, to my surprise, "I have vaseline in my top drawer." "Do you have
a towel you use for yourself? Like when you masturbate?" He said yes, it was with the vaseline. I hustled to the dresser drawer, retrieved the lube and cum-towel, put the towel on the bed directly under his tight balls and butt. I coated his hole and all around with a generous portion of lube. Vaseline. Old school. I liked this.
I coated my dick with one hand and put two fingers, lubed, up to his hole. I turned them back and forth, to pry him open and to slip them inside - lube up his pooper. I could tell this was uncomfortable for him. He clenched the blankets again. I held them inside of him for a few seconds, moved them in and out slowly, then keeping one fingertip still inside of him I pushed my dick up against his flesh for the first time. As I removed my fingertip I inserted the head of my dick, a little more forceful than I should have. He yelped, as I jabbed the entire head in. It just had to be done. I held it there, still, for a while and rubbed his back up and down, hoping to relax him.
"You okay?" I asked. He replied "Uh-huh. It hurts, though." I said, "It will just at first. I'll go slow." I bobbed the head in him gently. I lubed up the remaining 6 inches outside of his ass, putting extra coatings on the part that was going in next. I pushed slowly. I told him to push out a little like he does when he poops, but not too hard cause he may poop. He laughed. I got another inch in, then another inch, now half-way in. I pulled it out slowly, and right before it popped all the way out I eased it back in. He was breathing heavily. I started pumping a little faster. There was so much friction I had to pull out cause I thought I was going to cum. I looked down at his semi-gaping hole to see that there were a couple mole-sized specs of poop that surrounded his hole. My dick had a little on it too. It was light brown and soft looking. I dipped my dick down to his taint and wiped it off the head. Then I saw some more had collected between my tight foreskin and my head. I pulled the skin back to see shit all over, packed between. I could smell the scent strongly from where I was. I re-inserted myself, met with resistance again. He sure was tight. It was like I was going in for the first time again. All of a sudden, with no warning, I started oozing my cum right into his butt, just 3+ inches in. I held myself still and didn't let on that I was cumming, cause it was too soon and I wanted to keep going.
I pulled out. Cum was leaking from his butt. Some of it tinted brown from his pooper. I got on the bed and shimmied my way over to his head. He lifted his head and I put my dick up to his mouth. He opened his mouth and started licking the head. "It smells really bad," he said, but he then took it in his mouth and massaged the head with his tongue. He clearly had never had a penis in his mouth, but I wouldn't have thought otherwise. I shoved it in more and more, then told him to get up. I laid down on my back and told him I wanted him to get on top of me. He moved over and started to straddle me, then stopped and said "Can I put it in you now instead?" I paused, thinking I didn't see this coming, but figured he deserved it. I had never had a penis in my butt, but neither had he.
He got between my legs, kneeling on his knees. I told him he was going to have to lick it. He went right for it. I, last time I looked at my butt in the mirror, was pretty smooth. I had some dark hair around my hole, but it didn't go very far out. I also made it a point to wash myself pretty thoroughly. He went right in with his tongue. It felt amazing. He licked a little clumsily at first, but then got better. Then he grabbed some lube and drove his little prick right into me, so that his belly was up against the bottom of my balls. It knocked the wind out of me for a mili-second, but I took to it immediately afterwards. He looked like he was loving it so much, but lacked the coordination between the instinctual movements he wanted to make and the movement he was capable of. His penis was very slim, and at times it felt the tip was jabbing against my insides. This lasted for a total of a minute, tops, before he collapsed on my stomach and came inside me. He laid there for a bit, then got up. He shimmied his way over to my face, straddling my neck, and dangled his dick in front of me. "How do you like it?" he said jokingly. I opened my mouth and took his dick, that was just up my butt, into my mouth. It wasn't so bad. I sucked him till he was hard again, then asked him if I could put it back in his butt.
He backed up so that his butt hole was over my dick. I was oozing precum again, and totally hard. In fact, from my perspective, I looked girthier than I had ever seen myself. I told him to guide it in and move at the speed he wanted to. He moved slowly, lowering himself onto me about 2 inches, then stopping, removing my dick, then starting over. This time he kept going and going. He clenched his teeth and breathed heavy, looking up toward the ceiling, then closing his eyes. He held his breath and lowered himself so that 6 inches was inside of him, just less than an inch to be to the guild. He held still, then moved upwards. He went too far and I popped out again. As I came out he farted a wet sounding plop. I could feel some of my cum from before drip onto the shaft of my dick. He said "I want to lie down again."
He stretched himself out on his bed, on his back, and spread his legs. I inched my mouth toward his bum, licked his balls, his taint, and then down to his sticky, stinky hole. He was definitely leaking. Not so much shit, but more the lining
of his chute that mixed with the lube and my semen. It was kind of hot, I thought. I slipped two fingers inside him again, then even a third. He yelped a little, but told me to keep going. I got all three fingers almost half way in, but not quite. I was amazed I could even get that much in. I rubbed the head of my dick around his slightly parted hole, gathering up excess lube, cum, and some of the lad's bum juices, and shoved it back in. I started fucking him quickly. I pushed as far as I could into him, his eyes shot open wide and then closed into a squint. I rolled him over so that he was on his side, but I was still in the same position. I pulled at his waist and tugged him closer to me, so that his folded legs and bum were resting on my thighs. I could tell that I had gone so deep that I was past that second sphincter, the one that leads into the bowels. It felt open and cavernous. I moved my dick inside of him, up and down, really stretching him out. He was moaning loudly, at a regular rate. I drew my shaft almost all the way out, then plunge back in, the come all the
way out and just massage the head in and out quickly. I pulled out too far, more of his insides dripped out and onto the pubic hair above the base of my dick. I could see his poop being pushed down on my dick, and leaving little rings there.
I couldn't believe how turned on I was by this.
"You okay?" I asked quietly, breathing heavy as I fucked him. He barely muttered "Uh-huh." I pumped away for a couple
more minutes like this. I don't think I had ever been this rock hard. I pulled out all the way. He was panting and glistening with sweat. There were little tan mounds of poo and lube all around his dilated hole. My dick had some poop remnants on it as well, all gooey from my precum and the vaseline. I turned him onto his stomach and straightened his legs, then spread them apart a little. I placed my knees on the inside of his legs, mid-thigh, and slowly lowered myself onto him. He clenched and made noises of painful pleasure. I was as deep as I could be in this position, and certainly deep enough for him. I humped him real slow, long ins and outs. I flattened myself right onto his back, and tucked my bent arms under his armpits. He turned his head to the side. He was sweating, and looked very concentrated. "You still okay?" He said "Yeah, it feels good now." I moved faster and faster, then bobbed my legs around his so they were on the outside. I told him to bring his legs straight. He did so. I entered him again, and slid right in. I pumped hard and braced his shoulders, pulling him closer to me each time I sunk into his little butt. I could feel my second orgasm coming closer, so I took it slow, long strides, and I began shooting. I held it in him all the way for the first time, an extra little push that sent both of us over the edge. He gasped a high-picthed moan, and I shot at least 6 times inside of him.
I stayed in him for a half minute, then slowly pulled out, his cum-rag ready to collect whatever he was going to let out. As soon as the tip emerged, his butt spewed an almost endless stream of cum, in little throbs of his hole, producing tiny bubble-fart noises. I had definitely gone too far in, as small little turds rode the stream of lube and cum, of which there was ample. I watched as he gushed and gushed. He was limp and flat. The stream ended. I spread his hole with me hands, and opened it up with my finger. More juices flowed out of his bum, followed by one last bubbley fart. My dick was slick with cum, and had streaks of his poo. I was going to wipe it off on his towel, but the towel had been covered so much that I couldn't pick it up without all kinds of fluids running off onto his bedspread. Instead I wiped it off on his inner thigh. I crawled over in front of him, his face still on the bed, and I spread my legs around his shoulders. He lifted his head and opened his mouth. I stuck my penis in his mouth. He licked it clean. He started bobbing his mouth, up and down, but it was going limp. He stopped and we stayed still for about 10 minutes. I didn't know what to say, nor did he. But I wanted to make sure that he not feel bad about what we did. I also made it clear to him that we probably shouldn't do it again.