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(posted December 22, 2005)

Aiming For Pleasure

by Daniel Miller

With the semester almost over and the warm weather rolling in at least, I decided to take a well-deserved break from writing my master’s thesis. I settled down at a picnic table in front of the Campus Center with a soda and a plate of curly fries, enjoying the view as a group of shirtless frat boys tossed a frisbee around. I was so entranced by the sight of all those flexing, sweat-drenched muscles that I didn’t even register the frisbee heading straight toward me until it hit my wax cup smack in the middle, bursting it wide open and drenching me and my fries with cola. I was still sitting there, stunned and soaking wet, when one of the kids jogged up to me.

“Shit, man, I’m sorry. Are you okay?”

“I’m fine,” I said, catching my breath after the last of the ice had trickled its way down my shirt and into the crotch of my pants. “Just…startled.”

Actually, it was probably a good thing my eyes were a little glazed from the sudden cold. It helped obscure the fact that I was staring right at this boy’s bare nipples. The brown tips stood erect. They glistened with fresh, clean sweat. He was completely hairless, all the way down to the waistband of his loose nylon shorts, though a hint of brown curls poked through all the same. That dusty trail led to an obvious enormous mound that pushed gently at the middle seam of his shorts. I stared, mesmerized, as the excited flesh seemed to pulse and stir under the fabric.

“That was totally my fault. I shouldn’t have missed such an easy catch,” he was saying when I managed to tune back in.

He retrieved the fallen frisbee from the ground, tossed it back to his friends, and waved them off.

“Let me buy you another lunch. You know, to make up for the one I ruined.”

I was about to tell him that wasn’t necessary when I realized that he intended to stick around and eat it with me.

“So you should! Not because I think you owe it to me, though. Just because I’d appreciate the company!”

Reaching down, I lifted my clammy, wet shirt with my fingers.

“I’ll have to change out of this first.”

His fingers trailed over his bare chest. Fingertips gently brushed the tips of those perfect plump nipples.

“And I don’t have one on me to give you, mmm…”

He bit his lip for a minute, then his face lit up.

“My dorm room’s right over there,” he said, pointing. “Come on up and I’ll…lend you a new one.”

I nodded, got up, and followed him across the green to one of the older dorms on the campus. On the way over, he introduced himself as Jeremy and explained that he was a senior. That meant he had a single room. He asked if I were a professor.

“Nah,” I said, laughing.

At 30, I guess I am a little older than a lot of the other grad students, but no way am I stuffy enough to pass for one of the old goats in our faculty. That’s what I thought. That’s what I hoped. There was obvious relief in his clear grey eyes, followed by the hint of another emotion I knew pretty well. It got my boner up to full mast before we had even reached his tiny dorm room at the top of the stairs. Inside, he grinned as he reached out for the hem of my polo shirt.

“Here, give me that. We can hang it up while…uh…while I find you something else.”

“There’s no rush,” I told him.

He started to peel away my shirt in a slow, deliberate motion, running his fingers purposely but seemingly by accident up my bare chest. My flesh was still cool from the spilled cola. The sudden warmth of his hands made me shudder. I looked down at his crotch. What I saw there startled me. The boner he’d popped was jutting up at a 45-degree angle, so big it literally pushed the shorts up off his body. At one end of the raised cylinder was the outline of a cockhead as big as an ostrich egg. At the other was a melon-sized ballsack that bulged out around either side of the middle seam. How he managed to stay inside those skimpy pants at all was a mystery. I pulled him closer and hooked my thumbs into his elastic waistband. A second later he was standing naked in front of me. Now the mystery was over.

I paused to stare, open-mouthed, at what had to be the longest hard-on I’d ever seen. It swung between us like a baseball bat, a good 11-inches long. The piss-slit alone flared to the size of a dime. To see such a young, soft-bodied guy wielding a weapon like that left me momentarily speechless. Then a more practical concern occurred to me.

“How…how in the hell can you get that into a rubber?” I stammered.

Jeremy laughed.

“Don’t worry. I mail-order them special.”

Turning casually, probably so I could get a long, breathtaking look at his family jewels in profile, he sauntered over to his desk and fished out a box with a picture of King Kong on the front. When he unwrapped one and shook it out, it looked big enough to double as a windsock at the airport. It fit him like a glove, the latex clinging tightly enough that I could still see the outline of the pencil-sized vein bisecting his plump shaft. Keeping his legs wide apart, Jeremy flopped down on his narrow dorm bed and leaned back so his hard cock reared up in the air.

“I want to stick it up your ass,” he said in a husky voice. “I’m so big most guys won’t even try it. But I want to stick it in you.”

Jeremy stretched out on the bed, his legs open, his iron crowbar of a cock thrusting up at the ceiling. Under the stretched-out rubber, I could see the dark film of pre-cum already forming around his cockhead. He seemed to be getting bigger by the moment, though maybe that was just my fearful imagination. Licking my lips nervously, I crawled up beside him.

“You can sit on it,” he suggested, reaching down to massage his balls with his fingers.

Perhaps he was aware of my hesitation.

“That way you can take a little bit at a time. When it starts to hurt, you can stop for a minute.”

I dared to straddle him carefully, my own more modestly sized boner bobbing up in front of his face. With his free hand, he grasped my shaft and started kneading me like dough. With his other, he let go of his own bursting balls as he tilted his cock toward my asshole.

Grunting with the effort, I lowered myself onto his upthrust prong, trying to pace myself to maximize my pleasure and minimize my hurt. For the first few seconds, I didn’t think it was going to hurt all that much. Sure, his cockhead was pretty wide, but my ass-muscles seemed to flex and stretch to accommodate his girth just fine. I felt a little tearing sensation when his flange punched through my tight sphincter, but on the whole I thought I managed to fit him in pretty well. I smiled. I was happy with my success.

“Guess I’m not like most guys,” I grimaced.

Next came the first two inches of his shaft as he went on pushing his cockhead deeper into my guts. With a moan, he humped his hips and pushed in another inch or so. Then another. And suddenly the pain began. Long after most guys would have hit bottom, Jeremy kept on shoveling more cockmeat inside me. And I felt it, believe me. My distended guts burned, heaved, and strained against an invasion that seemed like it would never end. It really felt like he was shoving a clenched fist, followed by his entire arm, up my chute.

“That’s good,” Jeremy gasped, hoisting his ass off the mattress and skewering me deeper.

He gave my aching boner another powerful yank for good measure.

“Way better than most guys I’ve been with. You’re…you’re…really doing it. Not much more!”

“Yeah, I’m with you, man,” I grunted back.

By now it felt like I was slowly splitting down the middle, from the crack of my ass all the way up to the top of my head. All I wanted to do was hold myself together until we got it all inside.

“Not…not giving up.”

Taking a deep breath, I started wriggling my ass down on him. My whole body started to shake with the effort. Sweat poured down my back and dripped off my forehead, blurring my vision. My asshole felt like it had cleft open all the way to the underside of my balls. My entire middle turned into one fierce ache. Even my throbbing cock went temporarily numb in Jeremy’s fist, my bubbling cum ebbing back like the tide. More than once, I almost gave up as wave after wave of searing pain overwhelmed me. Then, almost before I knew what was happening, Jeremy’s whole body went rigid with pleasure.

“Oh! Omigawd, yes!” he wheezed. “I’m in! Oh, yeah, I’m all the fuckin’ way inside you!”

Sure enough, when I wriggled my ass, I could feel the scruffy fringe of his bush tickle my crack. I’d done it. I’d taken all of him inside my bunghole.

“What’s it feel like?’ he asked, his eyes glazed with happiness.

I guess he hadn’t been kidding when he’d said none of his other conquests had ever taken him that deep. He seemed genuinely interested in what I was experiencing, genuinely concerned.

“Does it hurt?”

“Yeah, just a little,” I answered through gritted teeth. “But to tell the truth, Jeremy, if you had another four or five inches, I bet I could take that too.”

His response was a deep, satisfied moan, and a few more tugs on my cock. The numbness I’d felt before disappeared as a rush of blood and cum flooded directly from my balls to my cockhead. A hot bolt of ecstasy zigzagged through my body with such force that it seemed to weld our bodies together. Jeremy was going to come any second too. I could tell from the expression on his face and the extreme tension of his balls against my crack. Summoning every shred of my willpower, I managed to flex my bruised bun-muscles around his jumbo sausage. But even the slight rubbing movement I managed to produce was too much for him, as I felt that fat firehose swell with fluid.

“G—gonna blow,” he croaked.

Sure enough, the pressure started building in my ass as the condom strained and squealed around a torrent of scalding jizz-juice. Every time he spasmed, his hips rose up in the air, lifting me half-off his body. Pretty soon, I started bouncing along with him. Desperate to keep that bucking snake inside me, I clamped my ass-cheeks together and rode him like an urban cowboy clinging to a mechanical bull. I’m sure my teeth would have been rattling if I hadn’t kept my jaws clamped shut in the most intense concentration I’ve ever known. Then he clamped both fists around my own shaft and started yanking me in a total frenzy. That was when I felt the last of my mental barriers crash.

The cum drained out of me in a searing wave that splashed his bare chest and ran in rivulets around his nipples. I don’t think I’d ever dumped so much so fast, but Jeremy didn’t seem to mind. No doubt the super soaker between his legs flooded that narrow little mattress every time he jacked off too. Bouncing wildly up and down, grunting and moaning, we drained ourselves to the dregs long before we slumped together in a shaking, sweaty, cum-sodden heap.

“That soda we were talking about sounds pretty good about now,” I commented when I finally found my voice again. “I think I’m dehydrated.”

Smiling weakly, Jeremy nodded.

“Sure thing. I’ve got that extra shirt around here too somewhere.”

He hoisted himself off the bed and started fumbling around the room, while I kept my eyes glued to the flaccid meatstick swinging between his legs like a baton. It occurred to me that if I could get it in my ass, I could probably cram most of it into my throat just as easily. And I was game.

“On second thought,” I croaked as he returned with two drinks in his hand.

Reaching out, I gathered his warm, cum-moistened helmet in my palm. The rounded bulb nearly filled my hand. Jeremy flashed me one of the horniest grins I’ve ever seen as my mouth started to open wide.

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