Between Boobs and a Hard Place

"Fuuuuccckk!" my girlfriend cried out, a deep and pained gurgle leaving her still open mouth as the cougar's bosom crashed into hers. I could see her firm, round boobs reshape against Patricia's for a moment, both women's racks molding together and splaying out violently. My eyes remained on Sabrina's dense titmeat as it waved out from the center of her chest, pushed inward by the opposing, more expansive mass of thick yet supple boobflesh. The top-heavy blonde leaned away briefly in order to ram her chest forward, thrusting those big, mature mammaries against the brunette's jiggling pair.

Sabrina cursed again, grunting as Patricia's attack forced her to back up a step, but managed to meet the next blow head-on. Both women groaned, and a loud smack of flesh meeting flesh erupted from their visibly displaced racks. While the milf's paler mounds did seem to morph around her rival's smaller breasts slightly, the brunette was pushing against the pressure in obvious discomfort. Patricia half-smirked, half-grimaced, sliding her big, hefty mounds from left to right and back, and I could see my girlfriend's boobs compress and shift as the larger set of breasts made their way across the space between them, both women's best assets moving more fluidly than before.

Having finally regained her bearings and her feet, Sabrina reached for the older woman's waist, pulling the blonde closer. Their ample busts smashed together more tightly, both pairs of breasts yielding some real estate. Patricia, whose ability to move was now greatly hindered, threw a short jab with her left breast, catching my girlfriend's right orb and causing it to wobble enticingly. That small distraction gave the buxom mature just enough room for a more powerful strike, which she took immediately, slinging her substantial jugs from the side and slapping them into Sabrina's still-shivering breasts.

My girlfriend didn't take long to start responding in kind, and I watched the fighters trade blows for a while, pounding their teats against one another with wild abandon until one particularly sharp, stinging slap from the milf caused my girlfriend to lose her grip on Patricia's waistline. As Sabrina stumbled slightly, the blonde, true to form, sprang forward and landed another solid blow with her full, weighty chest. My eyes followed the buxom - and obviously very skilled - housewife closely as she rammed ahead, tits-first. The forceful collision caused each woman to groan, and their sizable boobs to balloon out noticeably.

Both fighters looked down, and I noticed that Sabrina's expression was somewhat more pained, her rack having of course taken the brunt of the impact. As I followed their gazes downward, however, another possible explanation for the difference presented itself; the two large, meaty pairs of breasts seemed to meet at the same point, compressing against each other and slowly spilling away to the sides in an almost perfect mirror image. A small, strained smirk crept onto Patricia's lips as she took in the sight, and I saw her begin to twist her hips slightly, the blonde rolling her torso from side to side in a lazy rhythm. It was obvious to everyone in the room that the larger, somewhat more pendulous set of mammaries had managed to soften up their pert rivals quite a bit, Patricia's greater mass pounding and pummeling the thick breast-tissue in Sabrina's big, solid-looking tits and causing them to lose some of their usual cohesion.

It was a classic contest that pitted size and weight against youthful, springy firmness, and as I watched their breasts continue to meet each other evenly, waves of supple flesh ebbing and flowing back and forth with every push or shove, it was starting to look like the blonde's hefty jugs might actually prove too much for the brunette's perkier pair to contain. I could hear Sabrina trying to stifle a string of grunts and groans as she ground her boobs against Patricia's larger mounds with more vigor, their dense, meaty busts continuing to duel in a virtual stalemate despite her efforts.

"What's the matter, missy?" the blonde breathed out confidently, narrowing her eyes into a mean, almost predator-like look. "Don't tell me my big, strong boobs are turning those teen floppers to mush already?" Her sugary tone was laced with unmistakable smugness.

"Just what are they feeding you kids these days? All that cheap, fatty over-processed crap seems to be making your racks a lot softer than they look," the blonde grinned, emphasizing her point with a chest-bump that sent both sets of breasts into a delicious cascade of wobbling, ample titmeat.

"Mmm, they're so nice and comfy now," Patricia murmured throatily as her eyes drank in the scene below. "Much sexier than before. Your bouncy little jello-tits are going to look amazing covered in spunk."

"Oh, as if, you dumb whale," her opponent spat with an annoyed, unfriendly hiss, though I did think I could see Sabrina's cool expression betray some concern. She appeared to be losing her main advantage in this match, after all, and would need to find a way to turn the tide quickly.

Clearly determined to re-establish some control over the mature woman and her unexpectedly potent vintage mammaries, Sabrina forced herself back on the offensive. I watched her lean away for a second before ramming her still quite firm-looking, nicely rounded boobs into Patricia's substantial rack. The fierce piercing attack hit its mark dead-center, and Patricia let out a loud grunt, evidently feeling her rival's solid tits dent her own jugs slightly. The brunette kept her boobs there, allowing me to take a brief mental snapshot of their busts - my girl's tan, pert pair appearing to dig in and displace the more massive set of mammaries by just a bit - before Sabrina coiled her back, thrusting forward as she started to force the issue in a very intimate way.

"You've got a big mouth, granny," my girlfriend hissed through gritted teeth, her expression dangerous. "But do you really have the jugs to back it up? Why don't we see if these overaged fun-bags can hold off mine in a proper grind?"

Patricia's only reply was another grunt, and I could see Sabrina's taut upper back and shoulder muscles flex visibly as she turned up the heat. The brunette seemed to be doing her best to stab, shove and drill her boobs straight into the mature woman's pride and joy, making full use of her breasts' smaller size and pert shape. I watched in dully throbbing arousal how my girlfriend's dense titmeat slowly pressed forward as it sought to burrow its way into the blonde's plentiful flesh.

"I'm gonna fucking end your big, fat udders," Sabrina growled under her breath. She sounded slightly winded from the exertion, but her opponent's gasps and groans told me all I needed to know about who was controlling the space between them. I found myself idly wondering what the sensation was like, feeling your tits yield to another pair? To feel them slowly loosen up as the tissue inside lost its resistance, before finally breaking down completely and melting around a superior pair?

It did look like Patricia might be getting to experience all that pretty soon, I thought, watching how Sabrina worked her big, firm boobs further in. The brunette was sliding those impressive orbs across and against the blonde's fleshier pair, trying to force Patricia's large mammaries to part for her own. And appearing to make good progress with the attempt.

My imagination instantly conjured up a scene with Sabrina stroking my cock until I went off, jets of white spunk shooting out and landing on Patricia's loose, beaten udders as I coated the mature man-eater's soft bosom with my cum.

That little day-dream not only made my already painfully hard erection lurch violently, but also very nearly caused me to miss the blonde's counterattack. I only barely managed to drag my focus back to the present to see the older woman leaning down to sling her heavy teats upward - possibly for the second or third time?

In any case, the massive uppercut struck the underside of my girlfriend's sizable bust, deforming both of Sabrina's pert, solid breasts and propelling them to fly toward her chin. The brunette groaned loudly, clearly stunned by her opponent's powerful blow, and appeared to be still recovering from both surprise and pain when another slam, this one from the left, sent her round left breast crashing into her right one with a wet, meaty smack.

With another deep groan, Sabrina looked down, and I was sure she'd never seen or felt her big tits quiver like they were at that moment. Patricia's full, pendulous jugs were like boulders, it seemed, crashing into the brunette's firm but rapidly reddening teats and making them splay out and displace significantly. Not for the first time in this match, I wondered how my girlfriend might react to getting out-boobed by this voluptuous housewife. Despite their obvious age difference, the blonde's meaty jugs seemed to be giving Sabrina's perfect sorority-babe tits a serious workout, and if I was entirely honest, had so far proved themselves every bit as sexy and powerful as their college-student counterparts. This old bird must've been a right catch in the tit department back in the day.

Ahhh, who was I kidding. She still was.

As the buxom mature readied herself for yet another blow, appearing eager to keep whittling away the firmness in her opponent's boobs, Sabrina finally found an opening. She twisted her torso to the left violently, and I watched the tips of Patricia's mammaries - elongated from the centrifugal forces as she slung them outward - miss almost completely, brushing against the sides of my girlfriend's round tits as they barreled past. The brunette's grunt indicated that she'd felt Patricia's hard, thick nipples scrape across her visibly discolored skin, and I saw Sabrina wince as her big, tender boobs pushed in slightly from the glancing impact, jiggling on her chest and looking blotchy and sore.

Patricia cursed, her somewhat more pendulous set bending from the power she'd put behind her unsuccessful blow. I licked my lips, admiring the way the blonde's large, heavy jugs slapped back down with a wet smack and wobbled like two fleshy water balloons. Her once pale skin had turned bright red from all the pounding and grinding, but I couldn't really gauge much of a change in their shape or composition. Each ripe, feminine breast still stood proudly on the blonde's chest, hanging a bit from the weight and decades of gravity, but also looking decidedly majestic. Not to mention attractive.

Holy shit, I was no longer sure if I even wanted my girlfriend to win. The thought of seeing this milf's big, meaty breasts slowly overwhelm Sabrina's perfect tits was intensely arousing, and I couldn't resist picturing how the brunette's mouth opened into a silent moan as she felt her firm, young flesh getting pushed in, those once-unyielding sorority girl boobs spreading out gently as they reached their limit and started to make way for the mature woman's thick, powerful titmeat. My girlfriend's stunned, disbelieving gaze drifting down to witness her prized but by now badly worn-out breasts flatten and pancake against her chest, the brunette's outmatched pair at last losing the grueling contest of endurance and slowly succumbing to the blonde's more robust, dominant vintage rack...

Oooh fuck. Apparently, I could not WAIT to watch my girl get her epic tits flattened by some busty housewife!

Well okay, not by 'some' housewife. This particular old broad was seriously stacked. Now, she wasn't incredibly well-endowed in terms of pure size - larger than Sabrina of course, but nowhere near as massive as that top-heavy sorority sister of hers, Tanya - but clearly, those sexy, seasoned milf-jugs were made of impressively stern stuff.

Struggling to shake myself back to the present, I noticed that both women seemed to have chosen to take a moment to catch their breaths and to recuperate, each fighter squeezing and kneading their bruised breasts carefully, appearing to gauge their condition. All four mounds had sustained plenty of observable battle damage, looking red and tender. Even Sabrina's perfect boobs, which still weren't droopy or anything, certainly looked softer and more pliable than usual. I could only imagine how exquisite my girlfriend's young, nubile flesh would feel against my palm if the cougar actually managed to break them.

Out of all the breasts my greedy hands had gotten to grope and caress so far, Sabrina's were by far the firmest. Or, well okay, I guess Samantha could just about claim parity in that area. But since the Hooter babe I'd been dating briefly earlier this year was a tad smaller up top, it wasn't quite as impressive of an achievement. In addition to being smarter - and more importantly, way less prone to bouts of insecurity or enviousness - Sabrina also had her predecessor beat in pretty much every other beauty category, the brunette boasting both a prettier face and a more pronounced, strikingly svelte hourglass body. I had to admit that aside from Sam's thick, well-muscled cheerleader's thighs, which did hold some appeal, dumping the blonde for Sabrina had been nothing but an upgrade. My girlfriend was a bona fide stunner.

Which made it all the more curious that I now found myself lusting after a busty, full-figured milf who was over two decades her senior. Oh well...

Their short break now over, the two females stepped closer again, each large, full bust bouncing deliciously as they jutted out at the opposing pair in an obvious challenge. It was every man's teenage fantasy come to life, I thought, watching Sabrina and Patricia gently bring their breasts to meet nipple-to-nipple. My girlfriend's much younger pair still sagged less, maintaining a more rounded, pert shape, but looked sore and had lost quite a bit of firmness compared to their usual, just about ideal teardrop appearance. The cougar's slightly pendulous mammaries, in contrast, also appeared to have softened up from their initial state, and certainly had more noticeable droop and hang than the brunette's, but the difference between the two sets seemed to be smaller than at the start. Not a particularly encouraging sign for my girlfriend, I thought.

Sabrina was not on the same page with me, however.

"I'm going to wreck your sad, saggy boobs, you overaged skank," she sneered, sounding a lot more self-assured than I would've expected. Then again, she'd won all three matches I'd been to, including the one against that black Hooter girl, and certainly had quite a reputation within her sorority. In short, Sabrina seemed to have every reason to put a lot of stock in her tits.

"Oh really?" Patricia chortled, raising an amused eyebrow. "And just how were you planning to achieve that, sweetie?" she quipped, glancing down between them and giving the brunette's boobs a long, hard look. "Those sure aren't going to cut it. Your perky little tits put up a fight, I'll admit that, but they're on their last legs now."

"Speak for yourself, you wrinkly skank," my girlfriend spat back, her nostrils flaring in anger as she regarded the blonde's calm, confident face with cold fury. "You can't seriously think you can take me? These boobs have crushed some of the nicest and firmest racks around. Nearly all of them, in fact. You're dealing with one of the top girls in town."

"Yes, emphasis on 'girls', I'm sure," the older female noted, a wry smile caressing her lips. "Sweetie, my superb, womanly breasts have flattened more sets than you could ever dream of taming, and will outlast those teen dreams without much trouble," she breathed, her deep, husky tone full of promise.

God, I was so fucking hard. Never in my life had I lusted after a milf this badly. In that moment, I would've probably given my left nut for a chance to bang her. And to get to grope those gloriously ripe melons. Instead of spraying them with my spunk, I now found myself wanting to cum inside her. Holy shit was this old broad hot.

"I hope you're good at sucking tit, missy, 'cause you'll be doing a lot of that later tonight," I heard Patricia taunt the brunette, clearly loving her enraged expression. "Your hunk can join in, too, after I've fucked his brains out. Shouldn't take long, considering how horny he looks."

Oh thank you God, thank you! I could practically feel the cougar's strong, velvety cooch clamp around my dick and milk me dry. The need to fill this milf with my seed was so intense it hurt.

Sabrina was seething at the busty blonde, but took a deep, calming breath to regain her focus. It definitely wouldn't do to let rage fog up your concentration against such an experienced (and stacked) opponent. My girlfriend glanced down to see their breasts lined up, and pushed forward without further ceremony. Patricia grunted as she felt the brunette's tits trying to burrow again, and I saw Sabrina reach up to grab at Patricia's forearms. This time, the contact was slow and languid, almost erotic, as both women brushed their nipples against each other. Neither was able to hold back the soft groans from leaving their slightly parted lips, and I could only imagine all the tingles and shocks passing through their breasts. The sensations had to be close to ecstatic.

A close visual observation of the action seemed to confirm my initial assessment, and I took in Patricia's turgid, exceedingly stiff-looking nipples flicking across my girlfriend's. The cougar let out a low purr, her gaze sliding down to watch the younger woman's equally thick nubs rubbing against her own tips and dueling with them for a second before sliding to the side and starting to dig into her sore boobs, Sabrina's hardened nipples pushing the soft flesh inward.

Sabrina's eyes were on their chests as well, and she let out a groan when her own tips seemed to bend slightly during one pass, then sighed as she felt her turgid nipples pop free. I watched both pairs of big, meaty breasts pull back a few inches as each woman cupped their tits briefly. Without any warning - or even eye contact - the women thrusted their ample chests into the opposing pair at the same time. The resounding thud was dull and damp, and both fighters groaned as their large, tender boobs flattened at the point of impact.

A slight wince appeared on Patricia's face as Sabrina kept her tits in contact, and I watched my girlfriend begin to reach her arms around the busty mature, attempting to wrap her into a hug. She was clearly feeling confident about her chances in a close grind, and I had to admit that the brunette's tits had so far seemed to have her opponent's impressive but much less youthful rack at a disadvantage there. As thick and resilient as the tissue in Patricia's mammaries undeniably was, she couldn't quite match the college girl in sheer firmness. 'A' college girl, sure - I reckoned these big, premium-vintage breasts were at least as dense as that that blonde hooter babe Sydney's, maybe even better, despite having a more pendulous shape. Come to think of it, the two blondes appeared to be almost exactly the same size, though Patricia was of course easily old enough to be the hooter girl's mother, making it only logical that her rack, even if it did have superior density, would sag more obviously.

Besides, it's not like they were droopy or anything. More like... ripe and succulent? Their shape was full and plump, fairly rounded, and those big, mature jugs certainly looked very, very delectable to me. Oh shit, here I was again, fantasizing about a forty-something instead of that modelesque hooter blonde. And to be sincere, just then, if I'd had to choose, I may well have picked the cougar over the gorgeous teen. Sydney's bikini-model looks and beautifully curvaceous body be damned.

Speaking of figures, Patricia's own measurements were actually quite competitive in most key areas, I thought, watching her struggle against my girlfriend as the latter tried to pull, and the former sought to push. Apparently, the mature female had no interest in meeting her rival in a close-quarters tit-grinding engagement right now, and was instead doing her best to create some space between their sweaty, heaving chests.