Never Comes the Day

I took everything he had to give—and believe me, it was a lot—with only a minimal amount of choking. Moreover, as I grew comfortable having his meaty cock within my throat, and mentally adjusted to his various teases, I began to play up to his game. I'd hold him to me by that tight ass of his when he did that 'shifty-grindy' thing with his cock, daring him to leave it in longer.

A couple of times he got the better of me, making me gag, but it was all in good fun. Besides, when I gagged, it caused me to cough up more saliva, coating his beautiful cock further. I can't tell you how hot it made me seeing the heavy strands of my saliva drip thickly off his glistening pole. I almost came looking at it, saliva and pre-cum hanging off his shaft and balls as they did, when he pulled out.

Then, I added a little something special to the whole theme. When he was tight against me, I'd spread his buttocks and press a finger to his tight asshole. What surprised me was he liked it, and moaned loudly each time I did it.

Wow, you're not a total top. You like something there, don't you, bitch.

I gave him more of my finger as I held him tight against me. Then, pushing him back just enough so that I could take a short breath through my nose, I pulled him full in again. Sliding another finger into his ass, I took to fingering his asshole as he slow pumped my throat again.

He was groaning loud and long, even when I pushed him back again for more air, he continued to groan and moan. When I felt his legs tremble, I knew he was getting close.

Come on guys, take the hint and jump on in. Fuck his ass while he fucks my mouth.

Just then, he pulled away hard and out of my grasp. Looking down at me and breathing heavily, he said, "You bitch, you. Oh, you naughty, naughty twink. You are good...almost too good...but not yet. We have something special planned." With that, he turned away.

Something special? What the fuck.

I really didn't have time to think on Pete's words, as the others were on me like lightning. One after the other, they took quick turns thrusting into my mouth as Pete had done. No more than four or five thrusts at a time, but always making sure their balls slapped against my nose before the next man in line took his turn.

When they weren't fucking my mouth, their hands were down by my other end, soft stroking or playfully slapping at my cock, massaging my balls, and always, always, pushing well lubed fingers, three...four...even all five at a time, into my ass. They never gave me enough stimulation to get me off—the fucks—but just enough to keep me in that over-excited state. On top of all that, the quick thrusting and shifting to different partners was beginning to deprive me air, and I was feeling light-headed.

It was pretty obvious from the finger probes what they intended to do—getting me ready for Pistol Pete and his 'bazooka'—I just wasn't sure how. There was only enough room between me and the back of the couch for them to slip a hand through, as they continued with their finger probes.

I didn't have to wait long to find out.

Just as I was about to pass out from a lack of air, I felt them grip my legs firmly at my knees and ankles, and then they slid me off the couch and onto the floor. They didn't just lay me on the floor, however. Instead, they had something less pedestrian in mind.

It's hard to describe, but they put me into a weird, pseudo-headstand position, where the back of my head and neck rested flush on the floor, my legs were up in the air and my back was braced against the front of the couch. The Giggler and Clyde continued to have a firm hold of my ankles, giving me support, and then they brought my legs forward so that my lower torso hung above and over my head. It was odd to look up and see my own cock pointing back down at me.

I can't tell you how panicked I felt. Not just from the awkward position they had me in, where most of my weight was bearing down onto my neck, but the position made it difficult for me to breathe. I was feeling almost claustrophobic.

I tried to bellow, "What the fuck are you doing?" but given the constriction to my neck, it sounded like I had laryngitis, "If you want to fuck me, put me in a better way. Please!"

Giggler just laughed at my plea, while Clyde answered, "Shut up, twink, and get ready for the mother fuckin', ass fuckin' ride of your fuckin' bitch life."

It was then that I saw Pete standing over me, looking down and around that horse cock of his and into my eyes. You can't appreciate the size of his tool without seeing it with a rubber on. He was using the type and size the others had used, and although it was completely unrolled, it barely covered half his cock.

Talk about ten pounds of meat stuffed into a five pound bag!

The visual was awe inspiring, frightening, and comical at the same time. I laughed to myself wondering why the 'Group' never got him his own set of max jumbo condoms.

They make rubbers for donkeys, bulls and elephants, don't they?

In any event, I could see that he was already well greased. He waited a bit while Giggler squirted about a half a bottle of lube into my ass. When it looked like I was as prepared as I would get, Giggler and Clyde each took an ass cheek and spread me open. Pete kept one foot on the floor, near my head, and step over and between my legs with the other, bracing that one on the seat of the couch.

It was a weird and awkward position he put himself in, and I was curious to see how he was going to manage putting his cock in my ass without it breaking off.

I probably should have been more worried how my ass was going to accept the horse cock without collapsing in on itself, but such was my mind at the moment. His anterior engineering difficulties seemed more interesting to me than my posterior anatomical health.

I knew his great cock was 'bendy,' but I didn't think it was that 'bendy.' However, neat as you please, he just leaned a bit forward while grabbing the back of the couch with one hand, then pushed his cock down a tad with the other—presto chango—he slid right into me.

'Slid right in...' I make it sound easier than it was.

Easy for him, of course, he knew what he was doing. It was a totally different animal for yours truly.

I had been fucked six ways to Sunday, over and over, by most of them. They had lubed me up, pushed and prodded fingers and even hands into me until I could take any and all easily without pain, and still I wasn't ready for Pete's size. It was worse than that first butt fucking from Conklin. Pete barely pushed his cockhead in, before the shattering pain started.

I let out a loud grunt of agony. My cock, so stiff and hard moments ago, deflated like a pricked balloon from the pain. Worse than going soft, it just about retreated up into my body, like a turtle retreats back into its shell, as the pain continued.

None of the others said anything, or even made a sound. I guess they knew what I was going through, and stayed quiet out of pity and regard. Even the Giggler kept his normally incessant snickering in check.

Pete continued to push in, millimeter by millimeter, before halting for long stretches when my grunts and groans grew too loud. Unlike Conklin had done the day before, Pete never pulled out once he advanced to a particular point. I guess he didn't want to lose the ground just gained, and as I would learn, it was better that way. The constant pressure of his cock pressing into me forced me to relax sooner than I had with Conklin. However, until that point of calm was reached, I was groaning in pain and wondering what I'd say to the emergency room doctors as the sewed up the split in my ass.

What helped me get through the continual pain was that I focused on one particular thing, the advancement of his cock into my ass. For some reason, it seemed to deaden the pain somewhat—at least psychologically.

I had a ringside seat of the proceedings, and it was truly a sight to behold. I was amazed at how truly thick his cock was in comparison to my skinny ass. More amazing still, was that it fit at all.

Yet, there it was, thick and slick like a great serpent, slowly slithering its way inside of me and disappearing from view. Moreover, the more I focused on that thick rod spreading my ass wide, the more aroused I became. It was such a strange sensation, and one that I had never experienced before, to feel both pain and arousal at the same moment as he slowly advanced himself within me.

Somewhere, in the back of my mind, I had an urge to touch it as it made its way in. I touched all about my opening, and at the exposed part of his shaft, and felt such a heat at the junction of the two. His thick rod was hot, and my ass, stretched wide and cherry red, even hotter, as I ran my fingers over and around the area where his cock met my ass. He was so tight within me, it was as if we were one in that moment—welded together, pipe to spigot.

Excess lube was building up around that junction between cock and ass, having been scraped off the rubber and deposited there as he advanced inward. I took a little bit of the excess on a fingertip, and reached way up. Barely within my reach—he was only a quarter of the way inside me—I cupped his tightened balls within my palm. They too, felt warm to the touch, not nearly as warm as his cock, but close, and oh, so heavy.

A low moan escaped his lips as he halted his slow advance. He waited, letting me squeeze and massaged his heavy balls with abandon. Then I remembered his reaction from before, when I slipped a finger into him. Still cupping his balls with a palm, I slid my greased finger between his cheeks and pressed against his tight asshole. He moaned even louder as I slid my finger fully inside him.

It was sort of a trigger; a catharsis moment for the both of us. He grunted loudly in pleasure from my finger probe while pushing down gently, and I finally relaxed fully, accepting him with some ease.

Now that I could take him without pain, a torrential flood of euphoria and bliss washed over me. I was hard as a rock, again, as a large ball of sexual bliss started to expand in my groin, enveloping my whole lower torso.

As Pete began his slow, steady pumping, immediately I could feel my arousal building. I was still a long way to climax, but it was building in the right direction...and it continued to rise...only to stop just before the precipice—that point where climax was inevitable. Just like the other day with Conklin and Clyde, my arousal stalled, maddeningly short of its goal.

Pete never pushed all in, although I wanted him to, and only advanced about half-way each time. I thought that maybe if he pushed all in, it would trigger my climax. As such, I tried giving him clues he should pound deeper into my ass. I grabbed at his buttocks first and tried to pull on them, but my hands kept slipping off. Next I tried grabbing his thighs to pull him down that way, but he just stayed where he was, flexing his knees just enough to push his cock only half-way in. I even pulled on his balls, though not too hard, but still, he just continued with his slow, grinding fuck.

Not knowing what to do with my hands, I placed them everywhere, on his balls, his thighs, his ass, sifting them about haphazardly and without direction. I was hoping against hope that as they fluttered about they would magically spur him fuck me faster and harder. No such luck, however.

Soon, I fell into some sort of sexual trance and just stared at that thick piston of his, slowly grinding in and out of my ass.

It was hypnotic—and maddening—watching his thick stick slowly slid in and out of me. The fucker never went too deep, just deep enough to slide his cockhead past my prostate. Nor did he ever completely remove himself, which would, at least, have added a different sensation to his steady pumping. Instead, he would just glide his cock between head and quarter-shaft using that slow rhythm.

It was unvarying, almost monotonous, and like I said, definitely hypnotic. Moreover, as I continued to stare at it, I fell deeper into a trance. Soon, it was as if I could almost see, or visualize, it tickling my insides; tickling that part of me deep in my cock and balls that builds one toward climax. That was the maddening part. That was the thing that was driving me crazy the most. I could feel that his fat, heavy cock was slowly bringing me ever closer to release, but it was going far too slow. It was all like the low, slow smoldering of hot embers, never getting enough oxygen to produce a flame, but burning the fuel none-the-less. I knew all that was needed was my own metaphorical puff of air and my whole being would finally be set to blaze, but I just couldn't get it to happen. Where was the bellows that would finally ignite the smoldering embers?

I couldn't take much more of it, and started to beg, "Please! Jesus, would you just pound into my ass. Please, fuck my ass like I know you want to! I need you to fuck my ass long and hard!"

The onlookers all laughed at my plea, knowing the sexual agony Pete was driving me into.

I tried reaching a hand up to my cock, but again, someone slapped it away.

I went back to staring at the slow piston driving into my ass, almost willing it to pick up speed and force.

It was then that I caught sight of my own hard-on, hanging down, stiffly, a scant, couple of inches above my mouth.

An idea hit me—not a great idea, but an idea—and I wouldn't have to use my hands to accomplish it. Just a quick lick, or a short suck would be all I needed to get off and to stop this slow, creeping, butt fucking torment. They couldn't object to that, could they?

I latched hard onto my own ass in a vain effort to pull my head closer to my cock. I tried repeatedly to bend just enough to touch myself to my lips, or even just lick myself, but I always fell short of the goal.

The only thing I managed to do was repeatedly crush my insides against my diaphragm, and starve myself of air. I almost passed out from exhaustion. In the end, my tongue came up a fraction of an inch too short. A small droplet of pre-ejaculate fluid, undisturbed by my tongue, twinkled at me from my opening, mocking me.

********

Later on that evening, when this first round of sex games were over, Conklin put on the video he shot of our first cabana boy gangbang with me as star. When it came to this moment in the video, where I was straining to get myself off in any way possible, everyone began laughing and hooting their approval at my determination. Along with their laughter, they would repeatedly ask, "What are you trying to do, Jeff?" The question was always rhetorical, and said to give me embarrassment. They all knew damn well what I was trying to do, but they wanted to hear me say it; say that I was trying to suck myself off.

********

Back in the here and now, through the fog I was slowly descending into, I heard Giggler say, "Yeah, Gary couldn't do it either, although he tried...just like you, bitch." He giggled before adding, "Bitch wanna come? Then beg me, bitch."

I begged, a lot, professing undying loyalty to him and his clan.

Sexual favors to that inbred cousin of yours? No problem.

I loudly made promises to them all of an unlimited supply of blowjobs, day or night, if only one of them would speed me on my way to release.

You want me to do a blow and go on your buddy's intramural soccer team? All of them? But it's three in the fucking morning and you're drunk...oh, all right. Just make sure they're clean and no one has a rash.

That last promise wasn't much of a promise, since blowing them all, day or night, was my new gig from now on, anyway.

Only when I whimpered my final plea, just like a whipped puppy, did Giggler lift a finger to help. Thankfully, a finger was all that was needed.

He started by tracing a wetted finger around by tightened scrotum. Oh god it was nice. Not so much that it would get me off, but that the feeling was at least different from Pete's slow, monotonous, yet tortuous, grinding of my ass.

As he continued to trace my balls with a finger, Giggler gave Pete's ass a little squeeze, as he said, "Giddy up, Pete, time to ride this bitch into the sunset."

Pete quickened his pace, and took longer strokes as well. Immediately, I could feel my arousal begin to rise again, and it felt wonderful.

As Giggler continued to massage my balls and Pete continued pumping away, drops of pre-ejaculate fluid would form at my cockhead. They quickly grew as more fluid issued forth, before falling under their growing weight onto my lips below.

Giggler said, laughingly, "Just look at all that pre-cum, oozing out of that hard cock of yours. Lick it up, bitch. Ooh, it looks like there's more where that came from. Open wide and let it fall into your mouth."

I licked up the fluid that landed on my lips and then kept my mouth opened, as commanded. Like Conklin's pre-cum of the other day, mine had no discernable taste as far as I could tell, and even if it had, I probably wouldn't have noticed. My mind was slipping deeper into the sexual fog. All I really noticed was the smooth sliding of Pete's cock and Giggler's finger rub, as my arousal slowly continued to rise.

Hearing about all my pre-cum, Pete increased his pace and depth of his pumping. Now, I could feel his balls just brushing against my perineum.

Giggler continued to trace a finger around my balls, and sometimes ran that teasing digit of his down my shaft, which sent tingles shooting throughout my groin...

...and still the pre-cum continued to flow from my dick. Soon, a long strand of the clear, viscous fluid remained connected between my lips and cockhead. No matter what Giggler or Pete did, repeatedly tapping my cock or tapping my ass, the strand wouldn't break, and just twinkled in the lights as it vibrated from my tormentors' actions.

Seeing the state I had fallen into, Giggler took pity on me. Holding my cock steady and right over my mouth with one hand, he began using a circling finger massage along my shaft with the other, and slowly, ever so slowly, bringing that massaging finger closer to my cockhead.

Moreover, as he brought his finger lower, down my shaft, his action seemed to pull the feeling of my pending climax out of my groin where it had stalled, brought it out and forward where the burgeoning feeling of climax seemed to encase my cock and balls.

I had finally been brought to the pinnacle of climax, when everything seemed to align all at once. Pete slammed down into me hard, and stayed there with his balls flushed tight against mine. At that same moment, the Giggler finally touched my cockhead.

It was the barest of touches. A mere brush of his callused finger to the swelling underside of my head and shaft, but it was more than enough to ignite the embers. Pete's cock, renewing the hard pumping action of before as it raked across my prostate, became my bellows and did the rest.

Surprisingly, I thought my cum shot would burst out as rapid fire shots, as it usually does when I'm over-piqued in sexual arousal when ejaculating. Instead, it just flowed out, unbroken. Like one, long white waterfall of cum, flowing out and down and in and around my mouth. Only when Pete's cock pushed past my prostate did the rate of flow and the thickness of the stream briefly increase.

I licked and swallowed as much of my cum as I could, but there was too much. When it was all over, lot of it flowed and dripped off my cheeks and chin, and pooled along my neck, or oozed itself over my face and forehead.

I think I passed out briefly after climaxing, because I don't remember much immediately after. When we played back the video later, I saw that Pete didn't last much longer after me. He pumped into me five or six more times before pulling all the way out, pulled off the rubber, and fed me his cock as he jerked himself off.