Summer 1997. I was 16. In between my driver's ed class and my AP history class that July, I would walk through the woods between my high school and my friend Justin's house. It was usually 10 AM when I would show up, and he would always be asleep.
Justin, who was 15 that summer, and I had been friends for just a year at this point. Looking back I can't even remember what we did, but we spent all of our free time with each other. I had just started driving, and we had very few responsibilities. I do know that in the past year I had grown very fond of him, and although I identified myself as straight, I was physically attracted to him.
He was short and stocky, but very fit and athletic. I'd say he was 5'5", 135lbs., and, being of Irish descent, he was very pale. He had freckles, and big round blue eyes. I was lankier, about 5'9", 130, and dark hair.
I rang the doorbell. Moments later he opened the door, sleepy eyed, shirtless, in plain hanes boxers. As usual, I just followed him back into his bedroom. He'd turn on his stereo -- we were both really into punk. Again, I don't recall what we normally did. I guess we'd talk, he'd eat cereal, and after 2 hours I'd take the path back to school to finish up my class. This particular day, though, we broke whatever our routine normally was.
He was sitting on his bed when I noticed he was giggling. I looked at him waiting for a clue as to what he was laughing at. He just pointed down to his boxers. His dick was hanging out through the hole. This is the type of stuff we thought was absolutely the funniest thing in the world, with really no traces of sexuality attached; just teenagers appreciating our penises. He didn't put his dick back in though. It just remained limp, exposed.
"You've been throwing off my masturbation schedule coming over in the mornings. I've got to start doing it at night," He said.
"You can do it now, I don't mind," I replied, knowing that he wouldn't. We often discussed our jerking-off habits, so that was nothing new. We weren't those shy guys who pretend not to masturbate.
"Nah, it can wait." Just then, it started sort of bobbing, filling with blood. He started giggling again. "Or maybe not."
I decided I would just pull my dick out. It couldn't hurt. Plus we've been naked around each other before, skinny dipping and mooning the commuter train near the river. So I walked over and sat down next to him, pulling it out as I moved.
We both just sat there. He was fully hard at this point, and I didn't take a long time to catch up. We both started jerking off, staring at each other's junk. He soon reached over and touched my penis. It was a little bigger than his, probably 6.5 inches. His was about as long, but not as thick. Plus, he wasn't circumcised. "Want to give each other blow jobs?" I asked.
He smiled and blushed, "Not really."
"Okay," I said.
"I guess it would be good practice," he decided. "But I don't really want dick in my mouth."
He was no longer playing with my dick at all. He was just stroking his own. I inched toward him. I'm not sure if it was a reflex or what, but he removed his hand from his dick to allow my head access to it, saying, "What are you doing?" He knew what I was doing. I sucked and licked the head of his dick, putting my tongue between the head and the foreskin. He moaned softly, and said stuff like "Shit."
I pulled his boxers off, he bent his knees kicking them off. I moved onto the floor on my knees, giving some attention to the base of his penis. Then his balls. He spread his legs wider and bent his knees. I stroked his dick while I lifted his balls with my other hand. Straight ahead I saw my goal -- what I had started all of this for (I guess). His little button of an asshole, tucked away back there. I extended my tongue all I could, but it didn't reach. I pulled his hips forward a bit, pushed his legs back, and spread his cheeks.
He laughed a little "Oh man, I wouldn't do that if I were you," he advised. I did it anyway. He hole had a wisp of thin hair around it, but not very much at all. I could smell it though before my tongue even got there. I guess I hadn't occurred to me that even though I was highly aroused by the thought of his butt, that it would probably smell like shit. Makes sense.
My tongue made its mark. I stroked his hole up and down with the tip, trying not to inhale too much as I did it. He moaned softly, but immediately started giggling again. "This is so gay," he said.
I stopped my lapping for a second and agreed, "Yeah, it is. Can I put it up your butt?"
"No!" He said, but with a somewhat unconvincing smile.
"You can do it to me too," I offered.
He thought about it for a second. "Okay, but you can't tell anyone. Seriously."
With that, I stood up. "Turn over, I guess." He rolled over onto his knees, looking behind him somewhat nervously. I settled behind him and pulled his cheeks totally apart. I had never seen anyone's butthole before, but I quite liked his. His body was so taught and fit, and his butt was smooth and hairless. I crept the tip of my index finger inside. It was really tight and didn't even make it to my first knuckle. I took it out, spat on a couple fingers, rubbed it around his hole, and tried again (Several years earlier I had found an old Playboy from the 1970s in my uncle's garage, and there was a piece of erotic fiction of a woman describing how she likes a guy to warm her ass up before anal sex. I read it over and over, and I guess I learned something from it). My index finger got halfway in before being met by a lot of resistance, so I just kept it there, moving it slowly left to right. I pulled it out again. With it came a waft of poop smell.
"Ugh" I groaned.
"What?" Justin asked, somewhat alarmed.
"Smells gross."
"It's my ass dude. That's where my shit comes out." He laughed. "I haven't showered in a couple days either."
At that point I was done with trying to warm him up and wanted to get inside of him. Not knowing that a lubricant should be used, I just aimed my dick head with his hole and tried pushing in. I pushed his whole body forward instead. I braced his hips, pulling him close and tried again. The head of my penis just mashed up against his hole, not going in at all.
"I think you have to wet it first, dude." He said.
"With what?" I asked.
"I don't know. Spit."
I moved off the bed, around to his face and aimed my dick at his mouth. He reluctantly went for it, closing his eyes before wrapping his lips around my dick. He almost immediately spat it out. "That's gross. It smells like my ass," he said. I laughed, still rock hard, wanting to fuck him like crazy. "Just spit in your hand or something."
So I tried that, and attempted to get back in. This time I got my head in. He gasped. "Ow, ow, ow!"
I held it in him, still. "I don't know, man. This isn't working so well," I said.
"I think I have to take a shit," he added. I slowly pulled out. I could see I loosened him up a bit, cause his hole was showing the brightest pink I'd ever seen. It was fascinating.
"Maybe if I go in right when you finish taking a crap you'll be, like, relaxed enough for me to go in," I suggested.
With that, we got up and moved down the hall toward the bathroom. We didn't talk as we walked. We were on a mission now, even though both of us seemed to be somewhat unsure about how far we were prepared to go.
We went into the guest bathroom, as it was bigger and cleaner than the bathroom he and his younger brother shared. He started to sit on the toilet when I suggested he turn the other way, that way I can have easy access to his butt after he shits. "Oh, yeah," he said, as he turned around, facing the tank of the toilet.
He sat there for a few seconds before there was any action. Soon I could smell that he was about to let it go. I sat on the floor, facing his butt, watching his hole slowly open up.
"I've never seen anyone shit before," I added.
He didn't reply. Just then he started to poop. A long piece came out, looking thicker and about as long as what I was planning on putting in there. It fell on the front of the bowl, not sinking into the water completely.
"I'm almost done," he said.
It sure smelled, but now I was getting turned on by it. Then the next piece popped out, but really slowly. "Get ready. Spit on your dick or something." Instead I stood up real quick and pumped a few squirts of lotion by the sink into my hand. I coated my dick in it. The poop fell from his hole into the bowl, and I quickly replaced it with the tip of my dick. It was nice and loose. I was in an uncomfortable position, as was he I can imagine, my knees bent and legs spread low enough to get my dick at toilet bowl level. He grunted as I slowly pulled him onto his feet. Soon he was bent over in front of me, his hands gripping the lid of the toilet, with about 2 inches of my dick inside of him.
"Just hold it there. It kindov hurts," he said.
So I held it there. He flushed the toilet in the meantime and we both laughed. Without any effort at all I could feel myself sinking deeper into him with ease. I just slowly navigated the tip of my dick as far as it would go. After a minute I was balls deep in his butt. It felt amazing. I had to hold still just to keep from cumming. Once the feeling passed I slowly pulled out. I stood straight so I could watch my dick go in and out of him. I pulled almost all of the way out, shocked (for some reason) to see a smudge of shit on my pubes. His hole left streaks of poop on my shaft too. I pulled all the way out without thinking.
"Are you done?" He asked.
"No. But I guess you should have wiped." I said.
He laughed. "Lift your leg up onto the seat," I added. He put his foot up, and I guided the shit covered tip of my dick back in his butt. He cringed in pain and held his breath. "I think you should relax your muscles, otherwise it'll keep hurting," I said.
I could see him exhale and loosen up a bit. I was buried inside of him again. I started to pump him like a madman, it was feeling better than anything I had ever done while jerking off. In and out, in and out. I could tell I was getting closer to cumming. I wanted this feeling to last forever, or at least for five more minutes, but I gave in to it. I thrust my dick in him really hard a few more times, sweat dripping down my own hairless butt crack, my balls making slapping noises against his lower cheeks, then bang -- I held his hips against mine and squirt after squirt of my teenaged cum, 6.5 inches up his hole. I could feel my dick head had grown larger than ever before. I panted and let the last couple squirts of jizz come out with as much post-orgasm chill as I could muster.
Unlike later in life, when I mostly slept with girls, there was really no love here, no romance, so there was no cuddling or kissing or hugging. I just pulled out. Not gently enough either, as he cringed and gasped. My dick was a mess. Cum and shit and butt juices, all mixed together. His poop was caked around the tall ridge of my head, too. I stepped back, wanting to turn away before he saw, as I thought he may be embarrassed, but I got sidetracked watching my cum trickle down his thigh, followed by a piece of shit that was probably supposed to have made it into the toilet. He turned right around and sat on the toilet.
He burst into laughter. I did too. I washed myself in the sink. "That's gross," he added as he saw me picking the drier shit off the tip of my dick. "Oh man, that felt really weird." Just then he farted my cum and whatever I loosened up in there into the toilet. All kinds of gross, sloppy sounds.
"Get ready, man," He said. "You're up next."
"Well, I hope I'm cleaner for your sake."
(Part 2 soon)
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