Date: Fri, 30 Dec 2011 08:58:49 -0800 (PST) From: Coolie Labop Subject: Me and Jay 5 This is a continuation of "Me and Jay," a Nifty series under the "Young Friends" category. It is a true story. Feel free to contact the author at jtguy23@yahoo.com Once I had busted my anal cherry, there was very little that could intimidate me or scare me anymore. Jay began to take me to the roadside park more and more; we progressed from weekend nights to several times during the week, too. Men of all races, sizes, and ages would pay for my services, and of course we were still doing pretty good business with the photos and videos, too. Jay and I, of course, continued our sexual relationship through it all. After watching several men take me, he began to hint to me that he'd like to give it a shot. The day it finally happened started like any other. Jay picked me up from school, as he had been doing for a few months, and took me to my house. Since both my parents worked, we had the run of the place for several hours. We almost always fooled around first thing, because I'd been in school all day and would normally come home really horny. I've always found it extremely erotic to give pleasure, and usually the hornier I get, the more I want to please. On this day, we unlocked my house, grabbed a couple of sodas from the fridge, and made our way to my bedroom. As soon as we got in there, I took off my clothes. Jay liked me naked, and I enjoyed being looked at. For his part, Jay took his clothes off and we both climbed into my king-size bed. I grabbed his cock, already stiff with anticipation, and absentmindedly began stroking it. Jay had taught me, in the time since we'd first started, exactly what he liked, and I tried to do my best for him. When he was first getting started, he liked it when I wrapped his dick in my hand and used my thumb all over the head. Usually, Jay would produce a good amount of precum, and when I saw a drop form from his slit, I'd slide my thumb over it, spreading the lube all over the head of his prick. As he got harder and more turned on, he liked me to start pumping that dick, very slowly at first, gripping it tight in my hand. I'd bring my hand up, just to where I'd brush the underside of the rim of his head, then work my way back down to the base. Jay wasn't exactly hung like a horse, but he really enjoyed being stroked that way. The hornier he got, the faster he liked the strokes, and the more he liked to have my hand come all the way up, sliding over the head. He'd give me tons of his precum to work with, and I almost never had to use any lube with him. While I jacked him off, he ran his hands all over my smooth body. To this day I don't have much body hair, and of course I've always kept my privates shaved bald. Jay loved the silky feeling of my pubic mound, and the smoothness and softness of my bald sack. He really liked it when my balls drew up tight to my body, forming a compact little package. He cupped it, letting his fingertips trace down the seam, all the way to my asshole. "Let's 69," he said. "Hell yeah!" I climbed on top of him, and as I got into position my balls traced over his lips. He stuck out his tongue and gave them a lick, which made my little stiffy jump and swell. He took my dick in his hand and brought it down, since I was so hard, toward his mouth. I had my mouth at about his belly button, and I could see his cock throbbing with his heartbeat. I gave the tip a little lick, making Jay quiver, before engulfing his wet head with my eager mouth. I felt the warmth of Jay's mouth on mine, and his hands slid around to my butt cheeks, rubbing them and every once in a while, giving them a squeeze. Being in a 69 is always really interesting, whether it's with a man or woman, because it's almost like sensory overload. On the one hand, you’re focused on giving the person pleasure, and on the other you can feel them doing the same for you. While I greedily sucked Jay's cock, every once in a while I'd get a shockwave of pleasure from him giving me head, and I'd have to close my eyes and moan, usually with his dick deep in my mouth. I just couldn't keep quiet. We'd done a 69 a few times before, of course, but the first indication I had that this would be different was when I felt Jay's fingers working ever closer to my asshole. He normally wasn't really into anal play, but I guess his curiosity was getting to him. With his left hand, he sort of opened my cheeks, and with his right he traced a finger from the top of my crack down to the ring of my ass, then back up. He did this several times. I had learned from the men at the rest stop that anal play felt good, and I'd begun using things in my own ass when I masturbated alone, so I was completely fine with what he was doing. Just to reassure him, though, I gave a muffled "mmm hmm" when his finger traced over my anus. Faintly, I became aware that Jay was gathering some of his spit and my precum and lubing up his middle finger. He kept my cock in his mouth, but stopped sliding up and down on it, as his fingertip traced a circle around my hole. He pushed, and my ass opened for him, allowing the tip of his finger to penetrate me. Slowly, Jay inserted his entire finger into me, all the way down, deep. My penis reacted, swelling and jumping inside his mouth. He rewarded me by running his tongue all around it, focusing on the rim of my rather large head. I could feel that he was excited, too, for when he felt the warm tightness of my butt on his finger, his cock also got harder. The head pressed against the back of my throat, and there was the salty-sweet taste of more of his precum, which I swallowed. Soon, Jay let my erection slip out of his mouth, and his hands lifted my hips up off of him. He roughly placed me into a position on the bed where I was on all fours, with my ass up in the air. He got behind me. I had my head on a pillow as Jay's mouth found my ass for the first time. His tongue lightly brushed against my hole, before going around in slow, deliberate circles around it. I moaned, letting Jay know that I enjoyed what he was doing. Before long, he brought his finger back, and put it all the way into my asshole, while still licking the ring around the outside. In and out, in and out. He was speeding up, then slowing down. He took me to the edge of orgasm a time or two, then back down. When I glanced at the bed under me, I saw a pretty big wet spot where my cock had leaked precum. A little string of it ran from the sheet up to my pink cockhead. Jay fingered me for a pretty long time, bringing his mouth down every once in a while to lick and kiss. Then, without warning, he pulled his finger out. "Roll over," he told me. When I was on my back, knees up, legs spread, penis hard and throbbing, he looked me in the eye and asked if he could have me. "Have me?" I replied. "As in..." "Well, I, um..." Jay stammered. "You want to fuck me in the ass, don't you?" I said, boldly. Jay nodded, but said nothing. "Well," I said, "it’s not like I haven’t been fucked there. Yeah dude, you can do it.” Now, by this point I'd been fucked quite a few times, but it was always from behind, doggystyle. Jay, though, wanted to see my face while he did it, so he left me laying on my back. He reached under the bed, where I kept my baby oil (hey--I was a teenager) and spread a liberal amount of it on his prick. He raised my knees up, so that he had access to my butt. I helpfully reached down and spread my cheeks open for him. He put his dick, soaked in baby oil, up to my hole, and pushed. With little effort, he was in. I moaned, and said "oh, yes!" It felt good. Jay took little time in putting himself in me all the way, and while he didn't have the longest cock in the world, it was long enough to stimulate my prostate. He pulled it back, almost all the way out (I could feel the head spreading my anus) before pushing it back home. He brought his hands up to my chest and squeezed my nipples as he fucked me, speeding up a bit. Then, he reached down and took my hard on in his hand, and he jacked me off. I could hear the wet sounds of his fucking me and the sliding sound of his hand on my dick. The baby oil on his hand made it silky, and his hand slid effortlessly up and down my shaft. I had a moment where I sort of mentally paused and looked at the situation. Here I was, all of 14 years old, and my oldest friend was inside of me, fucking my asshole, while he had my cock in his hand. And both of us were enjoying it! I almost giggled at the absurdity. Before I knew it, Jay's pumping got fast and hard. His balls slapped against my asscheeks, and his grip on my own cock got tighter. He was going to cum soon. I'd learned that men really liked it when they got close to cumming if I squeezed my asshole, so I did that for Jay. The contraction of the muscle served to pull his cock deeper into me, and I could feel my insides locking down on his dick, making me tighter than any pussy. Jay fucking exploded inside me, and I continued to squeeze as tight as I could, milking his semen into my ass. He clenched his teeth and slammed into me, as though he were trying to shoot his load as deep inside me as humanly possible. I was already ready to blow my own load, and as he drenched my insides with his juices, I allowed myself to go over the edge. Jay actually had my penis pointed right at my face, and my first shot, aided by the pressure in my ass and the contraction of my muscles, left my slit fast, and hit me in the forehead. "Oh god, dude, yes, cum, cum, cum!" Jay said. "I am...I am...." I moaned. I shot my sticky white cum on my chest and belly before the orgasm started to subside and the rest of my load oozed out, down Jay's fingers and onto my pubic mound. For his part, Jay continued pumping my asshole as his orgasm faded. I could feel the warmth inside me. When it was all over, Jay sort of collapsed on top of me, his cock still inside, but softening now. His spunk slowly ran out the sides of my ass as his dick got smaller. I could feel it sliding down my crack and onto the bed. After about a minute, Jay pulled out of me and went for a towel to clean us up. I just laid there, two pretty big loads of semen on and in me, and smiled. I was having way more fun than most of my classmates!