Double Whammy

"Right! It's Jackhammer time!" I tore my gaze off of Aeryn and turned my attention back to Jack, right as the first blow fell. I winced as he drove his heavy rock hard member into mine, slamming into me painfully before pulling back. Taking a few moments to catch myself, I tried to push myself up but the second blow drove me back, relegating me to keep myself propped up only by my shoulders. Grimacing, I then attempted to shift to one side, but Jack still had me pinned by the wrists, and to curb my resistance, delivered a third impact. I grunted in pain. It hurt like hell but I wasn't going to give him the satisfaction of knowing he had gotten to me by crying out. With my hands pinned like they were I was at the total mercy of his hammering... and he was showing no mercy. If I could only pry my wrists free, maybe then-

WHAM! My body jerked as Jack delivered another impact. Thought train derailed and dick in agony, I gritted my teeth as I tried to twist my wrist free. My dick was really starting to feel it now, I NEEDED a reprieve. We'd started without too much of a size difference, but that was steadily growing once more as his shaft rammed into mine. This time I fell all the way back, lying prone on the mat. Jack tried to capitalize by shifting his grip back onto my shoulders, but I had enough sense left to keep my hands away from his. Instead he settling for positioning them on either side of me.

Just as I was about to rise up and throw him off of me, the hammer fell. Then again. And again. And again. Jack had picked up the pace of thrusts, no longer giving the long wind up but instead pounding against me relentlessly. There was nothing I could do but lie there helpless, grimacing as my cock was thoroughly thrashed by Jack's. Not only was his dick bludgeoning mine into submission, but there was another, secondary torment that I'd overlooked before. Each thrust not only hammered my member with his, but also caused his heavy balls to swing into mine, clubbing me with his heavy wrecking balls. Defenseless, I had no choice but to lie there as I learned the true meaning of 'take it like a man'.

After a few minutes of sheer agony, grunting as the entirety of my manhood was made to suffer under Jack's hammering blows, the pain began to subside somewhat. Maybe I was about to catch a break, perhaps the mighty 'Jackhammer' could only go on for so long before he hammered himself tired, this could be my change! Looking down to try and gauge the situation I saw that Jack's dick was still at full size, it was mine that was getting worn out. I watched in despair as Jack continued pounding into me, making a heavy, meaty slapping noise with each thrust. Now that I knew the score, I could feel my member losing nearly all of its size as Jack's erection battered and bludgeoned it back into nothing.

This couldn't be happening, there was no way someone like Jack could outdo me in size AND strength; the 'Jackhammer' should have been no match for my 'Infinerection' (patent pending). I could normally keep it up for hours and here Jack had busted me down to flaccid in... I glanced at the clock... thirty-seven minutes! That meant that there was only twenty-three minutes left! It was a stretch but if I could just get it back up and hold out to beat the clock; there was still the chance that I could win on a technicality. The climax tally was still zero to one in my favor after all.

Gritting my teeth I tried to flex my dick in quick sudden bursts in a bid to jump start my dwindled erection but Jack's grindstone cock filled each and every attempt with pounding agony. Before I'd been able to lift his heavier member with mine but now it looked like his cock pined mine mercilessly. I gritted my teeth and shut my eyes tight and I tried to will every ounce of energy into my dick...

"Alright boys, that's it, I've seen enough to make my decision." Wincing, I open my eyes to look over at Aeryn. Leaning forward with her hands on her knees, her legs were spread open allowing me to see a very visible wet spot on her G-string thong and against her inner thigh. Her eyes almost gleamed as she looked us over, and she casually flicked her long ponytail aside. I grimaced again. My dick, spurred on by her display gave a spirited attempt to come back from the grave but was met with an agonizing reprisal as Jack ground his dick down into mine.

Noticing him, Aeryn called out to him, "That's enough Jack." He didn't seem to notice and continued bearing down on me, squashing the prospect of an erection any time soon. She called out to him again, and this time I caught a hint of irritation in her voice, "I said, 'That's ENOUGH Jack.'" He faltered at this one, pausing in mid-press. He didn't apply as much pressure but the fact still remained that he still had my dick trapped under a full length pin, from head to base and even his balls, the entire weight of his manhood was pressing down on mine and doing no favors to my own virility.

Aping Aeryn, I gave him a dissatisfied glare, "Yeah Jack, get off me man." He snorted, giving a 'hmph' but finally pulled away. As he lifted his cock off of mine I was able to fully witness the devastation he'd caused first hand. I propped myself up and saw that Jack's heavy member was still rigidly hard and protruded straight out with veins bulging all along his thick shaft. On the other hand, although it was still somewhat large, Jack's meaty cock had left my dick completely powerless and it lied limply on my stomach.

Thoroughly worn out I slowly lifted myself up to get back onto my knees. Jack was already facing Aeryn with a smug air of superiority. As I shifted to face her as well, I flinched as I felt a jolt of pain, course through my softened member as it swung flaccidly between my legs. I glanced at Jack. Still jutting out proudly, his rock hard member was on full display for Aeryn, but there was silver lining to this storm cloud... there was still a good deal of dried up cum, MY dried up cum, on Jack's stomach and cock. Perhaps Aeryn would take that into consideration when making her decision. It was a slim chance though as my dick dangled unimpressively whilst Jack's jutted out proudly.

"Well, I've got to say that you both did surprisingly well. Much better than I had anticipated for either of you." She toyed with her hair alluringly, and I felt my stomach twist itself in knots as my erection failed to respond. She turned to me, treating to a sultry smile, "You gave Jack a real run for his money... and a very impressive money shot to close with. But that left you pretty much defenseless, a pity you let your guard down afterwards." She then turned to Jack, giving him a wry smirk, "And you, very impressive turn around. I almost had you marked as a goner if it weren't for you capitalizing on his post climactic cool-down." I smiled inwardly despite the pain, at least she had noticed who'd been directing the match for the most part. Aeryn smiled and looked at us both stretching erotically to show off her bodies curves. Again my stomach turned itself over at the lack of an erectile response whilst Jack's member stood strong, pulsing slightly from her little display. She smirked, then continued, "But, to quote Highlander, 'There can only be one' and so the winner is..."

Aeryn grinned, looking at us both, "Jack." I winced, but it didn't really come as too much of a surprise. I'd only come once, and although Jack was dry on that point, he had managed to retain his erection while mine's had gone limp. If that wasn't a clear sign of defeat then I don't know what would have counted. I sighed, shrugged, and gave Jack a curt nod (a handshake and a pat on the back probably wasn't the most appropriate of responses). I wasn't about to protest the fact that he'd tricked me into giving up my advantage, Aeryn had allowed it after all, that way I came off a gracious rival rather than a sore loser.

Jack sure was a sore winner though, "Hah-hah black boy. Looks like your dick was no match for the might of my awesome Jackhammer!" I looked at him mutely before shrugging it off. He'd won only by decision and all he got as a reward was first go with Aeryn, I'd still have the chance to screw her senseless afterward. I winced again as another pang shot through my shaft. That is IF I could get it up by then. I now understood what she'd meant by 'if he can still get it up', my cock had been ruthlessly bludgeoned into inactivity and even the smallest sign of life was accompanied by a tedious throbbing pain all through my shaft, even my balls felt like they'd gone through the ringer a few times over.

With me out of the picture for now, Aeryn focused in on Jack, smiling coyly and beckoning him towards her as she spread her legs. Erection throbbing and ready to go after defeating me, he stepped up to the plate eagerly and enthusiastically thrust his shaft between her legs. Mentally I gave a laugh, 'Hah! Anyone who knew anything about sex knew that you never just jumped right into things no matter how pent up you were. She could be seconds away from creaming herself, but you still had to build up the anticipation. Just shoving it in and thrusting? That was no way to get a girl worked up, you had to... to...'

My inner monologue petered out as the sounds of Aeryn's spirited cries of rapture sunk in. She'd wrapped her legs around his waist trying to drive him deeper even as he relentlessly pounded into her. Her hands gripped his back tightly and there was a distant look on her face as she moaned louder and louder. I couldn't help but be surprised, and even a little impressed at this turn around by Jack, he was turning out to be more competent than I had realized... At that, a nagging little thought popped into my head, 'Perhaps he was never that incompetent to begin with...'

That train of thought was cut off as Jack brought Aeryn to a screaming orgasm. An actual legs locked, toe curling, eye-rolling orgasm. Despite what had happened before I couldn't help but be impressed... and again that little monologue sunk in, 'How did you 'know' Jack was undersized? Did you really think a girl like Aeryn would trade in two studs for him without a good reason? Maybe this wasn't a chance for you to prove your worth, but for him to prove his... and you drew the short straw...'

Jack gave a few final thrusts for good measure as he came as well, burying his member deep inside her to shoot his load inside her. I tried to dismiss my doubts with the belief that while it was possible for Aeryn and Jack to be in cahoots in trying to make me look bad, her 'screaming orgasm', was more a performance from Aeryn than it was proficiency from Jack. I mean that was just something you saw in porn, girls didn't do that in real life.

Yet here Jack was, proving me wrong in the most brutally blatant of ways. Pulling his big cock out of Aeryn with a damp flopping noise, he looked over to me with an arrogant smirk as strands of cum trailing between Aeryn's quivering pussy and the head of his cock, "Alright, she's all yours little man," he gave a smug self- conceited chortle as he left Aeryn gasping on the couch, a thin sheen of his leftover cum smeared over her labia. "And to show I'm a good sport I even warmed her up for you." I grumbled inwardly at this 'show of sportsmanship'. I doubted that he or even Aeryn knew of my sexual prowess when it came to oral foreplay, so instead I chalked up his snide commentary on what was effectively an outright act of sabotage to general vindictiveness rather than arrogant gloating.

Frustrations aside, it was my turn now.

Though the pain in my dick had subsided significantly, I was still nowhere near to reaching full size yet. In theory, I could still work my magic with a lower level lip-lock that would soon have her screaming, but in reality, it was just too demeaning to get down on my knees and eat Aeryn out just after Jack had cum inside her. No, I'd have to do this the hard way without any foreplay whatsoever. Standing up, I cracked my fingers like a pianist, stretching my arms outward extravagantly as I stalled for time, "All right then, you've had fury, now it's time for finesse."

This got a haughty laugh from Jack, "Hah-hah, oh yes! Let's see how little Mr. Black Man compares to the Almighty Jackhammer," he gestured dismissively to my semi-hard hard cock, "And look! You still can't even manage to get it up! But I guess after getting hammered by my huge cock, your puny little pecker knows to stay down."

I did my best not to glare at him after that remark. Snide commentary and general vindictiveness aside, what was really getting to me was that arrogant little smirk he was wearing. Without resorting to cunnilingus I literally wasn't left with much to work with, and it would be a job and a half to wipe that smug grin off his face. However, as he took time to mock my mediocre member, I couldn't help but noticing that his own manhood seemed to be steadily shrinking as well. Perhaps I was right after all, maybe Jack was a one-trick pony; impressive out the gate but couldn't handle the long run.

Ignoring him, but keeping that invigorating thought in mind, I stepped toward Aeryn to take hold of her legs to continue from the Missionary Position. However, as I approached, Aeryn waved me away dazedly and for a moment I wondered if she was going back on her promise on letting me screw her. However seeing my expression she smiled, and gave me an airy sigh, "Hold... just hold on a second so I can catch myself..." For a few moments, she just lay there, panting and looking amazingly sexy while doing so. Each breath made her beautifully proportioned breasts rise and fall spectacularly and I could feel my stomach straighten itself out as my erection built back up to steam. After a minute or two of this, Aeryn gave a sultry smile, "Man... that was as exhausting as it was invigorating..."

"Well if you thought Jack was good, then I'll just have to show you Nirvana." I smiled back confidently; Aeryn's cool-down time had given my cock a few much needed moments of respite to revitalize. Nearly back up to full size, I thrust my rejuvenated erection out confidently for Aeryn's evident approval. Warmly smiling at her, I leaned forward and softly spoke into her ear, "Try not to cum TOO much," with just enough volume to let Jack overhear what I was saying.

Jack opened his mouth, primed for a snappy retort, but as he glanced down at my dick and noticed my burgeoning erection, he settled for giving a guttural grunt. I smiled inwardly, 'Not so smug now Jackie-Boy?' However, I didn't dwell on Jack's dwindling dick-size for long... after all I had more important things to think about. I looked down at Aeryn's prone body with a slick smile, "So Aeryn, if you'll all done lounging about after Jacks mediocre performance, how'd you like me to show you how it's really done?"

If one thing could be said about Aeryn it was that she was a real trooper; dedicated to her ideals. Even after a ruthless pounding from Jack's unwieldy dick, she still smiled eagerly as she spread her long legs wide open, licking her fingertips and encouragingly rubbing her pussy. With a sultry laugh and a saucy smile, she gestured for me to come forward, "Well then, if you feel so confident with yourself, feel free to step up to the plate and show me what I've been missing..." Her enthusiasm, especially after such a brutal bang at the hands of Jack, was worrisome, and again I wondered just what had I gotten myself into. However, the promise of steamy sex with a smoking hot babe quickly flooded me with a torrent of confidence.

Ignoring the dull aching sensation in my dick and forgetting the trials she'd put me through (not to mention the tribulations Jack had subjected me to), I happily complied. Still not fully recovered from the hammering prior, at first I didn't think I was hard enough to make it in, but Aeryn seemed loose enough for me to slide into her without too much difficulty. So sidling up between her legs, I gave her pussy an experimental massage with the head of cock, and then without further fanfare, shifted my hips forward for a hands-free entry.

Despite the smooth entry, once inside, her pussy gripped my cock like a vice. I groaned as she clamped down on me, her tight folds squeezing my still somewhat soft cock to a standstill. Gritting my teeth, I tried my best to thrust forward. With a harsh jerk, I managed to shove another inch deeper. Barely more than halfway in, I tried another thrust. This time I was rewarded with a throbbing pain along the length of my dick. Looking down, I saw that unable to move forward, my shaft had bunched up and bent sideways some. Trying not to panic at my predicament, I shifted my hips back. With her pussy still gripping the head of my cock in her tight folds, I was relieved to feel the bend straighten out.

Unsure as where or how to progress from here, I shifted my hands from off of Aeryn's legs and onto her hips. Lifting her waist, I pulled back as far as her tight folds would let me before thrusting forwards as forcefully as possible. I didn't make much progress penetration wise; my semi-soft cock scarcely sliding in even an inch, but the force of my thrust did manage to make Aeryn's boobs bounce spectacularly. Bracing myself, I backed off for another thrust forward; another bounce. Securing my grip on Aeryn's hips, I grinned inwardly.

I have to admit that I am an unabashed breast man and having Aeryn's fantastic pair right in my face was more than enough to counter the hammering Jack had handed me prior. With each thrust into Aeryn's tight cunt and every bounce of her supple tits, I could feel my erection strengthen, growing more and more rigid inside her. The way her lithe body was positioned allowed my dick to slide unbendingly into her tight body, and I could begin to steadily increase the speed and force of my thrusts beyond a slow tease. Soon I could hear her polite pants of feigned interest turn to genuine gasps of pleasure. Setbacks aside, I was finally gaining some traction with my modified missionary position.

However, while Aeryn was undoubtedly feeling it, I could also tell that I wasn't doing quite well enough to 'WOW' her. Though after the vigorous plowing she'd suffered just moments prior from Jack's tactless yet relentless fucking, who could really blame me? It was like trying to impress someone with fireworks after being blinded by a flash-bang.

I wouldn't say I was completely ineffective, after all I'd managed to get Aeryn moaning in genuine ecstasy, but there was at least a half octave difference in the impassioned cries she gave Jack and the subdued ones she was giving me. Jack hammering me down and plowing her out had left me with a significant uphill battle, unable to utilize my techniques that would have her having the orgasm of a lifetime.

With the effects of my efforts still limited, I knew that while she was undoubtedly feeling it I would need something more if I was to show up Jack and get her to cum at least as vocally as she'd been with him. A minute or two of an oral administration to her snatch would rectify the issue, but I wouldn't be putting my mouth anywhere near where Jack's dick had been. Furthermore, I doubted that Aeryn was in the mood for foreplay anymore, especially not after Jack's dry entry penetration. No, if I was going to wipe the grin of Jack's face, I'd have to ditch the mundane and take an extremely risky gamble.

Under the guise of adding a little extra oomph into my thrusts, I leaned in toward Aeryn wrapping my arms around her slim waist and securing my hold against her back. Her soft gasps took on a slightly raised pitch at our increased intimacy but suddenly turned into an impassioned cry of elation and surprise as I lifted her up off the couch to continue with a little mid-air intercourse.

At this sudden change in altitude, Aeryn wrapped her arms tightly around my neck whilst clamping her long lithe legs around my waist. With the added security of her support, I was then free to release her waist and shift my grip onto her pert ass. Not only did this give me a priceless opportunity to cop a feel of her tight buns, but in the process of shifting my grip she panicked and tightened her hold on me, sinking my dick even deeper inside her.