Between Boobs and a Hard Place

Between Boobs and a Hard Place

I still couldn't believe this was really happening. 

Less than an hour ago, my girlfriend and I had been on a night out, enjoying a few drinks at a night club that was pretty popular among college students such as ourselves. It being a Friday, there'd of course been plenty of older twenty- and thirty-somethings around as well, wage slaves, gig workers and corporate lackies alike letting off some steam - and burning some hard-earned cash. One of the party-goers, however, hadn't quite fit the bill.

I'd already noticed her earlier in the evening, eyeing me up from the bar. Or well, 'eating me up with her eyes' was probably a more accurate way of putting it. I was of course no stranger to getting lustful gazes from older ladies, but usually, they only served to make my skin crawl. This particular mature woman, however, had appeared to belong solidly in the 'sexy milf' category, her deep, fleshy cleavage on full display as she'd leaned over the counter and given her bountiful chest a quick shake. There was no doubt in my mind the show had been meant specifically for me, the chesty blonde's sly grin indicating she knew she'd gotten my attention, just like she'd wanted. Though given the apparent size and composition of the rack she'd been flaunting from across the room, I would've challenged any red-blooded male not to look. 

Now, she was no longer in the bloom of youth to be sure, probably in her mid-forties if I had to take a guess. But the blonde's physique, which was wrapped in a snug, almost skin-tight maroon cocktail dress, looked plenty tempting enough. Not quite the perfect hour hourglass figure, I thought, but featuring ample, luxurious curves in all the right places without looking flabby or out of shape. In one word, voluptuous.

Was I not already taken, I might've actually been tempted to walk over and chat her up. Mature women weren't really my thing in general, but this particular housewife was obviously game, and seemed to have a body built for sex. Ideal for a no strings attached one-night stand, or even a more recurring 'booty call' type of arrangement. Hot and steamy action for casual fun. Definitely attractive.

But since I WAS very much seeing someone, all that had been purely academic. My girlfriend, a college sophomore like me, was more than a match for the blonde in the looks department; her taut but curvaceous figure, sensual, dusky olive skin and beautiful face, which was topped by silky smooth black hair, made for one positively smokey and seductive package. On top of all that, she also had a pair of truly magnificent breasts. They were very firm, pert and round, and fairly sizable to boot. Sabrina was a total babe.

Befitting those slightly exotic, dark looks, my girlfriend did have a bit of a temper as well. So pissing her off by making eyes with some big-titted milf was a definite no-go. 

Oddly enough the blonde-haired mature had seemed to agree, laying off a bit once she'd caught my attention and waiting patiently until Sabrina eventually had to use the restroom. The minute she'd seen my girlfriend get up and head off, however, the cougar had pounced. Almost literally. My eyes had followed her approach all the way from the bar, the mature woman swaying her full hips deliberately and making those substantial assets on her chest jiggle with every step. Her eyes had been locked into mine the whole while, and though I hadn't quite realized it at the time - my brain having been somewhat short on blood due certain developments elsewhere in my body - the blonde had had the look of a carnivore stalking its prey as she'd traipsed toward me.

To cut the story short, Sabrina had found the shapely forty-something practically sitting on my lap, flicking her curly strawberry-blonde hair and leaning forward to let her hot breath land against my neck as she rubbed those large, ample mounds into me. She'd had me hard in seconds. Patricia, as she'd introduced herself, was not exactly shy, and knew exactly where her greatest appeal laid. I hadn't noticed my girlfriend's arrival at first, the cougar's highly provocative actions and deep, fleshy cleavage having distracted me quite effectively. To say Patricia had come over to flirt would've been an understatement.

In any case, there'd been some fireworks as you might imagine, Sabrina quickly yanking the blonde off me and proceeding to reward her brazenness with a slap or two for good measure. The older woman had been remarkably quick to recover from the sudden interruption and given back as good as she got, managing to catch my girlfriend with a nasty-looking open palmed blow to the temple before I'd had time to get in between them. Even then, it had been a struggle to pull the two hellcats apart, and it'd taken a mighty chest-bump, Patricia ramming her big, meaty rack against Sabrina's and causing the surprised brunette to recoil backwards right into the seat of the opposite booth (luckily unoccupied at the time) to bring about a cease in the hostilities.

As my girlfriend had lain there, sprawled on the bench seat, gathering her bearings, the stacked mature woman had issued a challenge to her. In no uncertain terms, she'd demanded that the brunette either prove she was woman enough to keep me - by facing her tit-to-tit in a proper match - or, and I quote, 'slink off home to mommy so you can stuff a bit more padding into that bra'. Sabrina's top was somewhat less revealing than the blonde's, but still displayed a fair amount of cleavage, and made it easy to discern that her assets weren't quite as substantial as Patricia's. Her dark eyes blazing with furious indignation, my girlfriend had accepted immediately. 

So here we were. In Sabrina's dorm room, at her sorority house, getting ready to decide my fate. It felt odd to be a trophy to be fought over, I have to admit. But not necessarily unpleasant. My member was still at half mast.

The brunette had calmed down significantly from her earlier, rather enraged demeanor, and was regarding the blonde-haired woman with a cold, catty or derisive rather than angry expression. Frankly, I thought Sabrina looked a bit snooty just then. 

Though given how much more prone to jealousy and neediness the girl I'd dated before her, Samantha, had been, I reckoned a bit of haughtiness was more than tolerable. Especially in these circumstances. 

My girlfriend was resting her hands on her hips, her head held high as she ran her eyes up and down the older female's body, a contemptuous smirk marring her otherwise very attractive face. Sabrina was still wearing the same outfit as before; a black, flimsy silk shirt with a close fit and rather generous neckline, plus a pair of even more snug-looking jeans. Compared to Patricia, she was pretty much dressed like a nun.

The full-figured blonde's cocktail dress looked somewhat redder in the bright lighting, its shiny surface sparkling slightly, and seemed to cling to her like a second skin. Its straps were thin, and the front provided quite an eyeful into the cougar's lavish, creamy cleavage. The dress looked almost obscene, and probably would've been a disaster, did its wearer not carry it so well. While Patricia was not exactly slender or lean, she did have nice proportions. The phrase 'thicker than a bowl of oatmeal' came to mind.

My girlfriend, whose gorgeous college-girl body was also quite shapely, but visibly more toned and compact than the milf's, did not appear to share that view.

"My god, no wonder Kristian couldn't tear his eyes away. You look like a total fucking train wreck," she sneered, shaking her head at the highly suggestively-dressed housewife in overt condescension.

"Any bets on how long it'll take me to get those droopy things all flattened out?" Sabrina asked with a snicker, her gaze meeting mine for a moment as she flashed me a saucy grin. She looked supremely confident as always. And with good reason, I knew.

"Ooh, someone's feeling their wheaties. I love deflating conceited little bitches like you," the blonde shot back, pursing her plump, red lips into a rather sly-looking grin. "Makes the whole stud-hunt that much more satisfying. We'll see how cocky you sound when you're on your knees, pleasuring my better breasts with your tongue while your guy gets ready to shoot his load on your loose, beaten sacks for one last time."

"I like my boy-toys to last more than a few seconds on the first round, you see. Taming them is easy enough as it is," the cougar murmured. Her smoldering eyes locked onto the visible tent in my crotch, my treasonous, quickly-hardening cock making a jolt as she licked her lips, slowly and sensuously.

"Mmm, not bad... not bad at all... You boyfriend's going to be thanking his lucky stars in the morning, that big cock totally drained by a real woman's mature, experienced pussy." Patricia's purr was low and positively feline, and her eyes seemed to burn with pure, confident lust.

"He may have the looks of a fucking Greek god, but once I'm done taking that young, muscular body apart, his voice will be hoarse from screaming out my name, and the only things still coming out of his pretty mouth will be whispers like 'yes, mommy' and 'please fuck me some more, mommy."

"Well aren't you a horny old tart..." Sabrina sputtered, sounding bemused, perhaps even a bit impressed. The nonplussed expression on her face displayed no concern or worry whatsoever, and more surprisingly, I couldn't spot too much anger or irritation either. The brunette appeared to treat her opponent's taunts about bedding her man - me - as little more than pre-match entertainment, obviously convinced of their emptiness.

"I hate to break this to you..." my girlfriend trailed off, pretending to be at a loss as she tilted her head in mock bewilderment. "But you seem to be suffering from a serious case of delusion. Or dementia, take your pick."

"I'm sure your rack's a real menace among the housewives, and may even have managed to flatten some weaker-titted college girls in the past. But those days long gone now," Sabrina sneered, her tone catty and dismissive.

"Your saggy old pillows aren't going to last more than a minute against my firm tits."

"Oh, I think you'll be surprised by how much punch they still pack, missy," the blonde replied, stepping forward and bringing her substantial, fabric-covered mammaries into contact with Sabrina's somewhat less ample pair. I looked on with great interest as the women pushed their clothed racks together, both flashing small grins at their rival as they felt their big boobs meet for the first time.

My eyes were glued to the action, staring at how each pair struggled against the pieces of lingerie surrounding them, pale and tan flesh spilling and bulging out of the cups as the women ground their breasts together gently. It wasn't difficult to tell whose jugs morphed more.

"See? My boobs are pushing those fat udders out of their support bra already," Sabrina smirked spitefully, her expression smug as ever. "This is going to be a cakewalk."

"Sure hope those toyboys of yours like having tit pancakes for breakfast," the brunette laughed. "'Cause that's what'll be on tomorrow's menu."

That small smile on Patricia's lips, however, didn't appear to be faltering. I watched her thrust forward with greater force, shoving her expansive bust against Sabrina's. Hard. I could hear my girlfriend's surprised grunt as more of her dense, full jugs began to squeeze out, compressing from the increased pressure as the blonde's deliciously plentiful mature mounds squashed against them.

"I'd pay closer attention to your own tits if were you. Those perky little teenboppers you've got trapped in your bra seem to be trying to escape. Unlike you, they can tell when they're outgunned," Patricia sang, her voice light and musical.

"Take a good look at your girl's cute boobies while you still can, pretty-boy," the blonde called out, glancing over in my direction and giving me a wink. "My bigger, sexier jugs are about to pancake them against her chest.

"You seem to be blind as well as senile, bitch," Sabrina snorted, pushing against the pressure confidently. "One set's pancaking, alright, but it isn't mine."

Like the figurative kid in a candy store, I gawked at the way all four breasts kept ballooning out of their bras, their partially-exposed titmeat ebbing and flowing with each shove. Still, my girlfriend definitely had a point, I thought, noting how the blonde's pale, ample flesh appeared to be molding noticeably more than the brunette's firm orbs did. Just as I'd expected them to.

What confused me was Patricia's serene, almost bored demeanor, the buxom cougar continuing to regard her opponent with that knowing smirk.

"Oh, you'll be singing a different tune soon enough, sweetie. I can promise you that," the blonde intoned softly. Her murmur was a strange mix of threat and amusement, appearing to contain both in equal measure.

"First, these thick, powerful jugs are going to squeeze your school-girl tits flat, squishing them like the cute little marshmallows they are," Patricia continued, her voice lowering and becoming more predatory. "And when you've finally paid the proper homage to your betters with that nasty, stuck-up mouth of yours," the blonde added, practically growling now, "I'll make you watch as I mount your tasty teen-dream hunk in your bed, wrapping my wet pussy around his big, hard cock like a vice and riding him like he's never been ridden before. His roars will turn into moans, and then into whimpers as I slowly take him apart. He's going to cum hard enough to see stars, time and time again, all night, until he'll forget he ever even knew you."

"I'm going to conquer your boyfriend the same way I'll conquer your precious young boobs. And you, you will get to see me fuck him to within an inch of his life."

"How's that sound, miss bitch-tits?

WOW. Just wow. I don't know about Sabrina, but to me, that sounded like an awful lot of fun. If this milf's dirty-talking was any indication, she ought to be a total beast in the sack. 

It's just too bad it wasn't ever going to happen. I'd seen my girlfriend beat some seriously impressive college-age knockers before, and highly doubted this (admittedly rather attractive) cougar had what it took to take her down. Patricia seemed to have a nice rack, but I knew you'd need a truly EPIC pair of breasts if you wanted to match, let alone surpass, Sabrina's perfect set. As much as that scenario intrigued my oversexed young mind, I knew there was simply no way this busty housewife could hope to out-boob my girlfriend.

Sabrina, quite unsurprisingly, was thinking along the same lines.

"You should've told me you were a comedian," the brunette muttered, shaking her head in genuine if a bit baffled amazement. She seemed to be entirely unfazed by Patricia's vividly detailed description of her intentions.

"If I'd known you were a professional jokester, I might've taken your ridiculous attempt to chat up my boyfriend, and the even more far-fetched challenge to titfight over him, as nothing more than improv stand-up." My girlfriend guffawed, but her tone was anything but friendly.

"Would've saved those hangers from a world of hurt," she added coolly. "But as it is, I'm afraid I'll have to insist on going ahead with the ceremonies."

"Fine by me." 

Patricia's laugh had a tinkling, almost fey-like ring to it, I idly noted, watching the full-figured blonde take a small step backwards as she first discarded her slinky dark-red cocktail dress in one clearly practiced, fluid motion, and then started to remove her bra. The lingerie she wore was beige and quite sheer, making her appear practically nude. I felt another lurch in my groin. She was one sexy housewife, alright.

A quiet 'snap' announced the clasp's release. Patricia's lacy garment slowly began to slide off, and my eyes followed two pale, jiggling globes as they fell on her chest slightly. Well aware that my attention was now fully on her, the mature woman pursed her lips seductively, grinning at my vacant expression as she leaned forward to free her breasts completely. They thudded down, shaking, and I could practically feel my eyes widen. Before me was a pair of breasts that seemed to be fully competitive with those of my previous girlfriends in attractiveness, and had all but one of them beat in size.

Making a soft, almost girly-sounding giggle, the voluptuous blonde cupped her large jugs as she slowly straightened her back. She flashed me a playful smile, letting those two glorious mammaries drop again, their denseness slapping against her chest with a dull, meaty thud. Each breast shook rather than wobbled, I noted, marveling at the lavish display. While you wouldn't call them 'perky' or even 'round', Patricia's large teats had far less sag than I'd anticipated, maintaining an ample and only moderately pendulous shape. Despite their age, each breast was located relatively high on the woman's torso, looking ripe and full.

And as a certain engorged, rapidly throbbing organ reminded me, also very, very arousing. While my mind was vaguely aware of the fact that those boner-inducing jugs belonged to a woman who was easily old enough to be my mother, 'the junior' downstairs did not seem to care one bit about such trivialities. I swallowed, craning my head towards Sabrina while I tried to look as sheepish as I possibly could.

It turned out I didn't have any reason to worry about invoking my girlfriend's wrath. The brunette's eyes were transfixed to Patricia's thick, heavy breasts, drinking in their unexpected fullness in silence. She blinked slowly, still offering no verbal reaction to her opponent's reveal, though her facial expression did tell me a story of some considerable surprise. Not that I could blame her; this mature broad was stacked like a page three girl. Sabrina quickly followed the blonde's lead and started to take her own top off. I watched her yank off her snug, thin blouse, flinging it to the side before she reached behind to remove her bra. Instead of leaning over like Patricia had, Sabrina cupped her big, round tits at the base, pulling them completely out and giving them a substantial shake.

My eyes locked onto a sight I'd gotten to ogle several times before, but which I knew I would never grow tired of. My girlfriend's pert, flawlessly-shaped boobs jiggled enticingly, their considerable firmness evident from the way those minute ripples swam across the tanned surface. When the brunette finally let go her breasts and allowed the dense titmeat to settle down, it did so almost immediately, all bounces and jiggles dying out after a second or two. She raised an eyebrow at her rival.

I noticed that Patricia had also gently palmed her own tits, cupping those large jugs from below for a moment as she stared down the young brunette. When she released them, both plump and mature mammaries fell with a delicious yet solid-looking bounce, two stiff, red nubs pointing directly ahead. If the cougar felt intimidated by my girlfriend's perfect college-babe boobs, she hid it remarkably well.

Now that their pairs had finally been unclothed, both women paused to give the other a once-over - and more importantly, to assess their opposition. I joined them eagerly.

Sabrina's full, just about ideally-formed teardrop tits sat high on her chest, seeming almost perky despite their size (a medium D-cup, I knew). They weren't as large Patricia's jugs, which could probably fill a low-to-mid range Double D bra if my guesstimation was correct, but still looked plenty big enough. You'd certainly count her in the 'busty' category when ranking the girls at the college. In any case, my girlfiend's prodigiously solid orbs had precious little visible hang, jutting out proudly like two slabs of marble. They looked absolutely magnificent.

Her dark nipples were growing larger in the cool air, and I took a deep, shuddering breath as Sabrina palmed her pert breasts again, this time lightly caressing both hardening tips. Her skin, boobs included, was much more tan than Patricia's, whose creamy complexion looked rather pale next to my girlfriend's olive-ish tone. Sabrina's nubs were sticking out of two dusky, half-dollar sized areolae, located dead center of her firm boobs. The bounce she'd given her breasts when showing them off to the blonde was not indicative at all. Without that deliberate effort, they barely jiggled.