The Greatest Humiliation Story Ch. 01

Part 1: The Rivalry between the Haves and the Have-Nots!

I still remember growing up in the seaside City of Middletown: We had two high schools, one 7-11 (that wouldn't card you when you bought beer!) and three churches, but what was really unusually was how this one sleepy town had so many "haves" and "have-nots." This was decades ago, before all the sloganeering about the One Percenters and Occupy Wall Street, but in the seaside City of Middletown, either you were filthy rich - or you were a poor, pathetic working stiff.

My family was... well, we were not filthy rich.

On the east side of town, right alongside the sparkling white seaboard, lived the filthy rich. They had the big, beautiful homes, the big, beautiful yachts - and all the beautiful housewives with the big, beautiful tits. On the other side of town were the poor. Their homes were smaller, their wives' tits were smaller... and instead of yachts, there were motorcycles.

Lots and lots of motorcycles.

The Queen Bee who ruled the city with an iron fist (and manicured French nails) was Mrs. Lacy Lovington, a.k.a. The Empress. She was the wife of the local Mayor - and good Lord, was she BEAUTIFUL! With her long blonde hair, eye-popping cleavage and ultra-curvy figure, she was the epitome of suburbanite sophistication. She always wore the latest fashion - Parisian dresses, Italian heels, Tahitian pearls and Manzoni mink coats (even when it was hot out) - and all these years later, I still remember how she'd tower over me. (Not that I minded; it meant that her freakishly big boobs were eye-level!) With her stiletto heels (and she ALWAYS wore heels) Mrs. Lovington was easily over six-foot, five-inches.

I'll admit it: I masturbated to her. (Hey, ALL the other 18-year-old seniors in my high school class did! Probably most of the teachers, too.) Okay, maybe she had a BIT of a butter-face and a slight double-chin, but the mild hint of pudginess was her only flaw. Trust me, she was a stunner.

She was also the mom of Timmy Lovington - my best friend. We were the same age and had been BFF's since kindergarten.

Mrs. Lovington was president of the PTA, president of the Church of Middletown, president of the School Board, president of Middletown's Special Events Committee... and the president of pretty much everything else she wanted. She had it all - and she also had an archenemy.

Rachel Trovolli.

Lacy Lovington and Rachel Trovolli HATED each other! And that's what the rest of this story is about:

Rachel was a tough-as-nails, pixie-sized brunette from the "wrong side of the tracks" who was more at home shooting pool than sipping Chardonnay at the Middletown Yacht Club. She was in her early 20s and always wore black leather pants, a snug black top, a black leather jacket and jet-black sunglasses. Her biker-boots were also black - with six-inch spiked heels. Her lipstick was bright red and her mascara was heavy, giving her something similar to a "Goth" look, but even if you're not into Goth-babes, there was no denying her beauty.

She had the world's sexiest smile. Like she was sharing a devilish secret with you - and you alone!

Rachel moved into Middletown a few years earlier, when her Dad (or maybe it was her uncle?) took a job at the construction yard. Almost immediately, Rachel was turning heads and dropping jaws. Maybe it was because of her tight tops, bold makeup and bad-girl attitude - or maybe it was because of how crazy-sexy she looked when she slammed back a few shots of Jack Daniels while kicking your ass at pool - but Rachel quickly became the most lusted-after girl in town.

If we weren't jerking-off to Lacy Lovington, we were doing the Five Knuckle Shuffle to Rachel Trovolli.

One night, Mrs. Lovington overheard Timmy and me talking about how sexy Rachel was. The tall, busty MILF glowered at us and snidely retorted, "You think that dark-haired little tramp is actually good-looking?! She's a shapeless twig with gaudy makeup! Furthermore, her REAL hair-color isn't even dark brown - it's light blonde! I heard it at the hair salon! And I'll bet you anything she stuffs her bra! You can tell! Hmmph!"

I was speechless, because until that moment I hadn't realized how jealous Mrs. Lovington was of Rachel. After all, the telltale sign of a woman's jealousy is when she belittles another woman's looks... and in my teenage mind, how could a woman as beautiful as Mrs. Lovington be jealous of anyone?

In hindsight, the writing was on the wall: ALL women are insecure, and let's face it, Mrs. Lovington was getting... older. Maybe late 30s, early 40s? And I noticed from Timmy's family photos, as Mrs. Lovington had matured, her hips had grown wider, her curves had grown fuller, and her outfits had become more layered. But back then, I was still a kid - I honestly didn't know any better.

The feud began with catty name-calling: Mrs. Lovington would demean Rachel whenever possible, calling her a "tramp" or a "slut" in a voice loud enough to be heard by EVERYONE. At first Rachel ignored her. But finally she responded by walking right up to Mrs. Lovington at the Middletown Thanksgiving Festival, where the glamorous MILF was showing off her new designer dress. All the important people in town were hovering around her.

"What a pretty dress, Lacy! I didn't realize they made them plus-sized!" Rachel purred.

Mrs. Lovington turned beet-red! But Rachel wasn't done:

"Hey, let me know when you get a zoning permit for that big ass of yours! I'm looking for a place to park my Harley. Well, see ya!"

Everyone tried to stifle their laughter, but you could still hear the snickering ricochet like rim-shots! Mrs. Lovington turned even redder and placed her hands over her butt. (Personally, I didn't know what Rachel was talking about: Sure, Mrs. Lovington's butt was bigger than normal, but to me it looked round, firm and perfect. I LOVED her ass!)

Christmas break was when the feud flew into overdrive. Two of Mrs. Lovington's relatives came to Middletown for their annual visit - Abby the sex-kitten and "mature" Yvette. A.K.A., the bitch-cousins.

Abby and Yvette were local legends. High school boys, college boy - it didn't matter. Every red-blooded male DREAMED of getting in their pants!

But none ever did.

They were older than Timmy and me and TOTAL snobs. We HATED them! Abby looked sort of similar to Mrs. Lovington: She had the same sexy hips, buxom frame and heaving cleavage, but with red hair instead of blonde. (We called her "arrogant Abby" behind her back, because her ego was the only thing bigger than her tits!) Yvette was prim and fussy, and had one of those expressions that seemed to convey how unimpressed she was with everything. Her big thing was bragging about how "mature" she was - and how Timmy and me were a pair of whiny little babies.

Still, the cousins were both gorgeous - and they never failed to dress to the nines. Abby mimicked her aunt's style and wore beautiful clothes that accentuated her large bust and rollercoaster-curves. She was so preoccupied with her looks; Abby never met a mirror she didn't like! Yvette wore less-revealing clothes that encouraged her firm, perky tits to pop right out of her torso. And whereas Abby typically dressed like a 20-something socialite who belonged in a swanky Manhattan nightclub, Yvette preferred to dress like a business executive in her early 30s - she called it the "sexy professional vixen" look.

Well, a high school senior was throwing a party, and Abby and Yvette dropped by to check it out (probably because they ran out of things to belittle). Most of us were wearing your typical high school clothes: jeans, t-shirts, and whatever else we could dig-up. Abby and Yvette, on the other hand, were dressed like they were walking the red carpet of a Hollywood movie premier!

A buddy of ours - Nedley Nelson, a 19-year-old dropout from the poor side of town - asked one of the cousins out on a date. (I forget which one.) What I DO remember is how Abby and Yvette laughed in his face! I had never seen anyone act so rude! Then they starting going back and forth, discussing what a pathetic LOSER he was:

"Look at his clothes! Hello? Like, shop at the Salvation Army much?"

"Like, totally! And nice hairstyle, homo! That bowl-cut totally says, 'I'm poor and my Mom cuts my hair in the front yard!' What a dork! Take a hike, needle-dick!"

A crowd of us observed the commotion, staring uncomfortably. I'm ashamed to say that none of us had the guts to stand up to them. Looking back, I guess we were afraid they would make fun of us, too... because, let's face it: Our clothes weren't any better...

But Rachel Trovolli wasn't scared. Hell no! She was watching the whole thing while perched on her motorcycle. Hearing enough, Rachel took a final swig of beer, hopped off her Harley and marched right over - flicking her cigarette in the cousins' faces!

"Ow!! W - watch it, skank!!" shrieked Yvette, the "mature" one.

"You think it's cool to insult my friends?" threatened Rachel. "Just because your clothes are more expensive?"

"Oh, whatever!" snapped Abby. "As if we'd date your loser friends!"

"Yeah!" chimed Yvette, making the "Loser" sign with her hand. "Like we'd ever date a Middletown high school dork. No offense, but we're REAL women - and we dress the part, bitch!"

Rachel narrowed her eye. "So, it's your fancy clothes that make you too good for Nedley, hmm? The clothes make the woman? Well, let's see how you look without them. Strip!"

The cousins gaped at her. "You, like, can't be serious!" Abby sputtered. "We're totally not stripping, you psycho! Tell your loser friend to, like, go buy a Playboy!"

"How immature!" sneered Yvette. "YOU WISH you could see a naked body as FINE as ours!"

Rachel cocked her fist and glared menacingly: "If you don't want your spoiled faces busted and bleeding, you will do exactly what I say. NOW STRIP!"

Abby and Yvette glanced nervously at each other. One of them tried to protest -

- and Rachel SLAPPED her right in the face! Then she SLAPPED the other! And then she SLAPPED them again! Although they were both taller than Rachel, it was obvious that the leather-clad brunette had them completely intimidated!

Shaking and trembling, both girls began disrobing - outside, in front of everyone! Yvette, the "mature" one, turned bright pink, hyperventilating like an asthmatic little kid. Abby, the curvier one, looked like she wanted to cry. First their fancy designer jackets hit the ground. Then their blouses were unbuttoned and removed. Next, their skirts were unzipped. Yvette slid off her pantyhose. It was so quiet, you could hear a pin drop as they wiggled out of their clothes...

Soon, the two rich bitches were stripped to their bra and panties! Yvette had white, ultra-firm undergarments - exactly what a 30-something lawyer or CEO might wear. Abby's undies were black, sexy and silk - surprisingly slutty. But Abby was also wearing something else... something... WEIRD was wrapped around her stomach...?

"Is that a girdle?" laughed Rachel.

Abby instantly began bawling like a baby: "No! It - it's for my back! It's a back-brace! I - I have a bad back, that's all! STOP LOOKING AT ME!!"

"Yeah, a bad back from carrying too many bags of Cheetos! Take it off, Fatty!"

With everyone circled around her, Abby howled in humiliation. Cameras were flashing as she popped out of the girdle. POP!! And POP is the right way to describe it, because once her belly was freed from the confines of the girdle, a big, flabby tummy sagged over the top of Abby's panties!

"Wow, what a porker!" someone laughed.

Abby just stood there with her eyes wide open, her big tummy shaking violently.

"I think she swallowed a bowling ball!" giggled another.

Both cousins looked like they were going to die of embarrassment!

But Rachel wasn't done: "Okay, ladies - take off your bras. Do it!"

Now a blubbering, quivering mess, Abby reached behind her back and unhooked her Victoria's Secret brassiere. OUT came her glorious tits! Her long, sagging breasts were crowned with saucer-sized areolas that wobbled in the night breeze - easily the biggest tits ANYONE had ever seen. They had no firmness whatsoever - but they were HUGE. The audience roared with approval. (And my teenage mind just about exploded!)

"Look at those udders!" said one boy.

And look, we did!

"Big deal - all fat girls have big tits," retorted a girl. "See? Her stomach sticks out farther than her tits!"

Abby tried to suck-in her stomach... but the girl was right!

Meanwhile, Yvette refused to move. Instead, her eyes were wide open...

"Please... please don't make me!" she whispered to Rachel, keeping her arms crossed over her sturdy white bra. "Please let me keep my bra! Please - I'll do anything you want!"

"Why should I let you?" asked Rachel.

"Because... because... I - I have a secret!" Yvette whispered.

"You rich-bitches shouldn't keep secrets from us!" Rachel laughed.

With the crowd chanting, "Take it off! Take it off!" Rachel reached over to Yvette - and with one hard yank, tore the bra completely off her body!

Two silicone falsies flew through the air, spinning like footballs, landing softly on the ground.

It took Yvette a split-second to react, but we all saw her: She was as flat as a board! She was stuffing her bra! By the time she covered herself, it was too late: All our eyes had seen her tiny little nipples. "Mature" Yvette was as flat as a middle-schooler!

(Weirdly, I noticed Rachel blush when she saw Yvette's miniscule titties. Nobody else noticed, though.)

What a scene! The crowd was roaring in approval, pointing, laughing and repeating: "Fat Ass and Tiny Tits! Fat Ass and Tiny Tits! Fat Ass and Tiny Tits!"

"Now lower your panties to your knees and put your hands on your heads!" Rachel demanded. "Let's see your cute little bushes!"

Both cousins were too shell-shocked to disobey: Abby sobbed and clumsily yanked down her panties, revealing a thick, tangled, black web of pubic hair that definitely DID NOT match her ginger mane. Her bulbous ass wiggled and vibrated with every breath - almost like ocean waves on a stormy night. (By contrast, Yvette's pussy was as bare as a cue-ball. Totally bald! Not one hair! And her scrawny little butt was half-the-size of Abby's.)

"Not a natural red-head, are we?" laughed Rachel.

"Sh - shut up!!"

"And you... wow, you're completely hairless! Weren't you bragging about how 'mature' you were?"

"WAH!! WAH!! WAAAAAAAAHHHHH!!"

For the next several minutes everyone was cheering and taking pictures of the cousins' private charms. Arrogant Abby was forced to shake her jelly-belly and go: "MOOOO!! MOOOO!!" Just like a cow! And flatchested Yvette was made to cluck like a scrawny, titless chicken: "CLUCK, CLUCK, CLUCK!"

Only after offering a naked apology to Nedley (and kissing his feet) were they allowed to go.

The next day, when Lacy Lovington heard about what happened, she was FURIOUS! The Empress of Middletown was convinced that her family dignity had been violated...

...And she blamed Rachel Travolli, SWEARING to get even!

But Rachel wasn't the only target of Mrs. Lovington's wrath: When I went to Timmy's house the next day, both cousins were still there. Only they weren't wearing their fancy-shmancy clothes anymore. And they weren't wearing their fancy-shmancy makeup and jewelry. And they weren't making fun of the way I looked.

I couldn't believe my eyes:

Yvette was TOTALLY naked, standing pigeon-toed next to the Lovington's backyard pool, being lectured by a college-aged swimming instructor! The very same swimming instructor who taught Timmy how to swim when he was younger!

I looked closer: Yvette wasn't actually totally naked. She was wearing inflatable swimming rings around her arms. "My Little Pony" swimming rings, to be precise.

When she saw me, she tried to cover herself - but Mrs. Lovington was having none of it: "Oh, stop it, Yvette. Everyone's already seen your little-girl body, and it's not my fault you forgot to pack a swimsuit without those silly falsies. I don't care how old your college I.D. says you are; to me and everyone else, it looks like you haven't even reached puberty yet. Put down your arms! You look ridiculous!"

The swimming instructor roared with laughter! With a look of absolute dejection, Yvette lowered her arms... letting me see everything once again. And I had to agree: She looked JUST like a middle-schooler! Even though Yvette had always dressed so mature, without her clothes, it truly looked like she hadn't developed at all: Her body was shapeless, her pussy was bald, and instead of womanly tits, she had pointy little nips. And then - SPLASH! - she was thrown in the pool by the instructor! I stared at her narrow ass as she swam away...

Even more shocking was the other end of the yard: Abby was buck-naked, jumping rope! Her big belly, saggy breasts and wide hips shook and jiggled with every jump! Her long red hair was a frazzled mess! She saw me staring at her body and freaked out:

"Pl - Please, Aunt Lacy! L - Let me come in! Th - this boy is w - watching!"

"No," Mrs. Lovington curtly replied. "You need to exercise AT LEAST another half-hour. I WILL NOT have a tubby little cow for a relative. Now finish your workout!"

The sight was hypnotic! Those large breasts heaving! That black, furry pussy glistening with sweat! Those big thighs and chubby buns!

Timmy told me how furious his mother was. "Mum says our family name was dishonored. If you think Mum's mad at Abby and Yvette, you ought to hear what she says she's going to do to Rachel! I've never seen her so angry!"

However, I thought that maybe Mrs. Lovington had another reason to be angry - a reason that was deeply personal. It happened about a month ago:

After swimming in the pool with Timmy, he asked me to go upstairs to his parent's room to grab some suntan lotion from their upstairs bathroom. We thought we were all alone in the house.

But... we weren't.

I guess Mrs. Lovington had just gotten out of the shower!

She was dripping wet, holding nothing but a small towel near the middle of her body. No shoes, no clothes, no makeup, no false eyelashes - nothing at all - when I barged into the room.

When she saw me, she gasped... nearly dropping the towel!

My heart skipped a beat.

It was the first time I had ever seen her like that! Even when I spent the night (which was fairly often), the next morning for breakfast, Mrs. Lovington was ALWAYS wearing top-dollar makeup, expensive jewelry and had her beautiful blonde hair immaculately-styled. (And of course she was always wearing clothes! Duh!) It was... so BIZARRE to see her like this!

The towel was BARELY covering her feminine goodies!

I'll never forget what she looked like: Without her makeup, her face was pale. Almost blotchy! Her lips and eyes seemed so exposed without their accessories. I looked down her body: Her thighs were fat and meaty, with a fair degree of cellulite. And it's funny, I had never noticed how THICK her midsection was! Even from behind the towel, you could get a pretty good idea of her true figure, and I'm telling you, she looked more like my chubby Aunt Patty than the sexy MILF-goddess who ruled the neighborhood!

I think she desperately wanted to scream at me - but she froze!

At that exact moment, I noticed that her naked rear-end was being reflected in the bathroom mirror! Clear as a bell! The very same derriere that I had lusted after for YEARS was now unveiled in all its glory! Yet I was stunned to discover that her REAL ass wasn't round and firm at all, but dimply and rectangular, with multiple pimples across her wet, white bootie! Her butt-crack was deep and pronounced, making each cheek seem almost like separate entities. Baby got BACK! Lots and LOTS of back!