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When Harriet Met Sallie: A Sissy Cuckold Story

Chapter One: Sal Has a Very Bad Day

Salvatore Brewster was having a terrible day. To start, he got fired from his menial job for the third time in less than a year. As usual, he groaned that “it couldn’t be his fault.” He was (or, had been) a stocker at the local big-box home store. For starters, he was twenty minutes late to work that morning, then in a rush to get a refrigerator off a high shelf, he turned the forklift too quickly, knocking the fridge into the one next to it, causing a fridge avalanche on the backside of the shelf.

“Anyone could have an accident,” his Goliath-like supervisor, Mike Delgado’s angry red face barked at him, in front of the whole backroom staff (who had run to the commotion of the tumbling refrigerators).

“…but it doesn’t help if you don’t follow basic safety protocols. Just Clock-out! and don’t bother coming back! That’s y’r last strike! Ye’r done! Brewster!!”

At home (in the apartment he shared with his wife, Harriet), he responded to his former supervisor as if he were in the room:

“Whoever put that fridge there in the first place? That’s! whose fault this was. It was packed too close to the next one.”

He mumbled aloud to the empty apartment, ignoring the “spotter rule” when moving larger items from high shelves, also forgetting it was he, himself, who had placed that fridge there two weeks earlier. Neglecting also that he had raced to get the fridge down with no spotter, to make up time after sneaking out to take a few tokes of his vape pen; running into his friend Randy on break, he took more than a few.

Harriet was still at work when he got home. She had recently been promoted from cashier at the local Fraugger’s supermarket, to executive assistant to the VP/COO, at corporate headquarters. The whole thing was serendipitous; she cashed out a customer, while he was checking her out hard, and he offered her the promotion on the spot.

She was so hot, she had to beat back men hitting on her all the time. She was a stunning beauty, tall winsome, with caramel skin and long curly reddish-brown hair, big beautiful tits that sat up high on her chest, the kind of curves that drive men crazy, long shapely legs to go with them, and a simply spectacular plump ass. She was 26, but looked younger.

How Salvatore Brewster–a runty pasty little white boy–ever scored this gorgeous Amazon was anyone’s guess. It was, Sal’s greatest achievement. As for Harriet, she might’ve said, he was sweet and loved her unconditionally, though he was a loser who couldn’t hold down a job or protect her in any traditionally masculine way. In fact, in their relationship, she did most of the protecting; she was more imposing, muscular and outweighed him by ten pounds.

Harriet was biracial; her mother a striking Irish redhead and her father a tall, dark, handsome African-American, now a retired Marine Corps Sergeant Major. Her mother died when she was four; so, she was raised by a very strict, very uptight and self-righteous Marine, who would not brook the slightest disobedience. She was punished with “the belt” for infractions her friends might have been put on “timeout” or grounded–like breaking her 7 pm curfew as a late-teen, by ten minutes, when many of her friends were staying out partying all night.

From Sergeant Major Harold Hopewell’s perspective, the fact that his prized daughter had married a loser like Salvatore Brewster was an act of rebellion, from which she would eventually repent. He lived in hope that she would realize the error of her ways and divorce the pathetic twerp and find a suitable match more befitting a daughter of his.

The man flirting with her at the register would be closer to what her father imagined for his daughter. Dressed in a Brooks Brothers’ suit, Tyrone Thompson was not representative of the clientele at this Fraugger’s market. He didn’t even look like a man who did his own grocery-shopping. At 41, he was already the Chief Operating Officer of Fraugger’s Markets, Inc.

He was fortuitously on his way from the grand opening of a new mega-store way out in the boonies and happened to stop in this store, in Harriet and Sal’s little town, more than an hour and from his office, where his store was a primary employer.

He spotted her immediately, as he walked in. He made sure to go to her checkout line and flirt with her in a very cocky way. She did no more than blush and smile tensely. He reminded her of her father, the same kind of tall manly build, nothing like her Salvatore. She had to admit she found his looks and his cocky manner arousing. It was oddly familiar and comfortable to her.

Her mind drifted to thoughts of little Sal and all his issues. They had met in college as third-years. Sal was about to flunk out and was the primary driver for Harriet dropping out the following year, her senior year with just a few courses to finish (Sal had not bursa otele gelen eskort accumulated enough credits to be called a senior).

“We don’t need to be turned into corporate tools,” he had said to her. Yet another reason Harriet’s Marine Corps father resented Salvatore.

Before Sal, she had done everything her demanding father asked; she got good grades, exercised regularly, followed her father’s strict rules. And, all her boyfriends had been big jocks or ROTC types, with similar attitudes, but those guys seemed like assholes; she thought she’d try something new with Salvatore. Perhaps it was a rebellion against her domineering father, after all. But now, after years with him, she often thought of her former boyfriends, with some regret.

Mr. Thompson showed her a business card bearing his title and offered her a promotion on the spot. There was something in her, he said, “that made him sure she was meant for a better position.” He emphasized the last word, creepily, and chuckled under his breath at his private joke. She would be making about five times her minimum-wage salary, plus benefits. In the back of her mind, she had an idea of what such an offer might entail. But she pushed those thoughts out of her mind and accepted the job, without another word.

“Besides…” she thought, “if she had to fuck somebody for a job that paid all their bills, this tall handsome stranger wouldn’t be much of a hardship.”

Salvatore’s terrible day was three months almost to the day after Harriet started the new job.

Having been fired, Sal thought he’d do something nice, like clean up the apartment and make dinner, before his wife got home from work. He would gently break the news of losing yet another job. He had plenty of time; he got home about 3pm, and she was not due home until the quarter to six, at the earliest. But as usual, he began to straighten their messy apartment, by getting high, then figured he had enough time to rub out a quicky. He was just setting up, when his phone rang.

It was Harriet, “Hey, Sal, sorry, I’ll be late getting home from work tonight.” She sounded genuinely sad.

“Oh…, mm-k.” He hummed unconcerned. This would him give more playtime.

Since her rise to Fraugger’s HQ, her mood around the house had improved dramatically from the cashier days. They were also flush; she bought all sorts of things, improvements for the apartment, furniture, and a whole new, not off the discount rack or Goodwill, wardrobe.

Her life improved significantly; they had gone from eking out a living at $20K/year to having disposable income at $92k per annum, and her new boss sent a Towncar to pick her up and take her home every day. Sal was probably wiser to attribute the mood change to these new conditions, but even he must have had an inkling there was more to it.

This would be the third Friday in a row, along with a few of random mid-week days, that she would be home late. Another man might have been suspicious, but Sal didn’t imagine there could be anything going on. “Besides…,” he thought; he had met Harriet’s new boss at a company event the previous weekend, and he was a real asshole to her the whole time: barking orders, like she was his personal slave, and belittling her in front of people.

Sal didn’t dare say anything, not wanting to jeopardize her new job, and, ya’ know… being a wimp. But she seemed to accept this treatment, which was not at all like her; he chalked it up to her also wanting to keep the job. He didn’t want to ask her about it either, fearing it would make her feel bad. So, he pretended he hadn’t notice.

The last two Fridays, she had gotten home after ten O’clock, exhausted and gone right to bed. Sal’s first thought after her call was: “well… that gives me time to really get my groove on,” and he wiggled his skinny ass around, as he sucked on his Hindu Kush-filled vape pen–yet another perk of Harriet’s new gig. He got good and high first.

He wandered around the house in a desultory attempt at cleaning for almost two hours, before getting down to business then connected a laptop to the new fifty-inch monitor, another perk. He went into the laundry hamper and found a used pair of her panties.

He sniffed a few, looking for the foulest ones; he found a really funky pair that felt musty. He covered his face with it and took a big whiff; they smelled like pussy, and something else, he couldn’t quite place it. He slipped them on. The nastiness of it turned him on, as his pea-sized testicles rubbed up against his wife’s drying juices.

Before Harriet, Salvatore had had no luck with women; and she was a complete fluke, only the second woman he ever went out with and the only one with whom he’d ever had sex; he was a sexual naif then. Today, however, he was a chronic masturbator whose tastes in porn had evolved in a very peculiar direction. He started with vanilla porn: hetero-vaginal intercourse with hot elden ödeme alan escort women and men. But from the very first, he couldn’t help notice how much bigger the penises in porn were. He chocked it up to self-selection, them being in porn and all.

But it made him curious about how big a penis could be; at the time, he had never seen a live one, except his own meager equipment. He Googled: “largest cock size,” genuinely looking for information, but got a ton porn videos with big cocks; that soon led him to BBC. He began to spend more of his masturbatory energy focused on the cocks than the girl. He still appreciated a hot girl, big tits, hot ass, but more as pleasing repositories for big black cocks.

After that, he moved on to anal, which first made him contemplate what one of those cocks might feel like up his own ass. Next, was trans porn, and now he was obsessed with sissy hypno videos. All of this, of course, he kept a deep dark secret, hidden from the world, and even, one might say, himself. Wherever his kink led him, he just repeated to himself that he was still very much a cisgendered heterosexual man, in love and attracted to his hot wife; these were just fantasies to jerk off to, and no more.

He did have a hot wife, but not a very satisfied one. From early in their relationship their sex life consisted of very little penetrative sex and mostly Salvatore going down on Harriet to get her off. He certainly could not get her off with his tiny little prick; and though both he and she, pretended it had happened, they both knew deep down: his teeny peenie had never given her an orgasm.

Each session they would passionately kiss, he would eat her out, then poke his semi-stiff three inches into her and cum in less than four minutes. Then, he would clean her out, eating his own puny cum. After the first two years, where this cycle was repeated more-or-less weekly, it became monthly, and then bi-monthly. They had slowed to birthdays, anniversaries, maybe Christmas, if he had been a “good boy.” On his terrible night, it had been much more than three months since he had been with, or even just seen, his wife naked.

Over the years, Sal turned more and more to porn and his right hand. And, these days, the idea of something up his ass, while he jerked off watching sissy hypnos dominated his mind. He hadn’t tried more than a finger or two up there, but he often thought of it when looking at phallic objects he came across; he had even contemplated getting a toy at the adult shop off the interstate. The urge to try something this particular night was overwhelming, especially after his difficult day.

He was particularly horned-up that night. The shame of his huge alpha-male ex-boss humiliating him in front of everyone and abruptly firing him, while he stared up at him like a scolded puppy, weighed on him. It didn’t arouse him directly, but it was like he had to overcome the shame through an extended session of masturbating to sexually humiliating videos. He was sexually and socially inadequate and the humiliation had become naturalized and somehow turned into arousal. He had noticed his penis twinge, even as the tall burly manager shouted at him.

As his tiny penis engorged from arousal, Mike Delgado’s image, his angry face snarling at him; his huge body towering over him would pop into his mind. As the video showed pictures of similarly shaped alpha men and the soundtrack encouraged him to obey and worship them.

He had stopped at Fraugger’s, on his way home, to get groceries for dinner, and now searched through the bags for the carrots he had bought. When he picked them out, the thought flashed through his mind. And, he had chosen, perhaps subconsciously, especially phallic carrots. He picked the one that looked to him most like the delicious cocks he obsessed about on sissy porn sites. He looked around the apartment for some kind of lubrication.

He was about to settle for Crisco, when it occurred to him to look through her dresser for lotion or cream, or anything he could use.

He found more than he bargained for. Apparently, he was not the only one in the house fantasizing about big black cocks. His wife had a rather large, remote-controlled, very realistic (including huge balls), black dildo stashed in a box at the bottom of the “junk” drawer in her dresser.

“How long has this been here,” he thought. Looking at the monster, he got very excited; it looked like the most appealing cocks he had seen in his videos. He was half drooling, but also a little frightened by it. The carrot was about half the girth of this thing; there was no way he thought. But he had time; “who knows when I’ll get another chance?” He whispered to himself.

He found some lube in the box too. He brought his new found treasures into the living room and searched online for his latest obsession. He had been consumed for weeks with videos of sissies coming from anal: “a sissygasm,” eskort bursa he had just learned it was called. He laid out a towel on the new couch and began to open his hole with two fingers using his wife’s lube.

He worked his tiny prick, while pushing two fingers in his hole, while the video played. He was trying not to touch his peenie too much so he would last longer, rubbing it only from time to time. He wondered if he could really make himself cum from just anal, like the sissies he obsessively watched. He had searched and learned that to help achieved this, he should not jerk his peenie, but he did not have the discipline to keep from touching himself altogether.

In the video, a sissy was sucking on a great big black cock, he took up the carrot, it was about six inches long–his wife’s huge black dildo, just within reach, was twice that. He tried to keep up with the sissy on the screen, sucking on the carrot like it was a real cock and worshipping it, licking it, and slobbering over it.

Suddenly, the video scene changed, and a new sissy was jumping up and down on a big fat black cock in her ass. Her caged little clitty bounced uselessly as she rode the cock in reverse cowgirl position, squeezing puffy little titlets. He thought that’s what he needed: to cage his teeny prick so he could concentrate on achieving a sissygasm.

The audio-track was pounding electronic music with a voice repeating humiliating phrases like “you love big black cock,” and “you want to suck cock, Faggot! You only deserve to cum from anal, sissy!”

He held his wife’s dirty panties aside and slowly pushed the carrot onto, then gently in, his tight anal rosebud. The lube had a numbing agent, so that when his anal ring distended, it didn’t hurt as much as expected. It was painful but felt like a pleasant pressure to him, filling up his bowels as he wiggled around, driving it deeper. Soon he was matching the screen sissies stroke for stroke and his tiny penis stood straight out like a twig, tenting his wife’s soiled panties, the feeling in his ass so overwhelming, he now forgot about jerking his peenie.

The next clip went back to the first sissy, only now there was another cock in the frame and she was sucking on it, shoving it all the way down her throat. He grabbed the great big dildo and imitated the screen sissy. He could barely get the head of the rubber cock in even with his mouth opened at its maximum. He took it out and spat on it and tried again.

It was so thick; he could feel the corners of his mouth stretching and aching, and he got the head in finally, but no more. The carrot felt so good in his ass; there had been so much more pleasure than pain, he thought he would try to switch. He thought of the improbability of fitting a cock in his ass that couldn’t fit in his mouth. On the screen a similar sized cock pounded into the sissy’s hole as she begged for more and moaned alluringly on the cock she was sucking.

He took out the carrot, and proceeded to try to impale himself on the monster dildo. He added lube and spit to the fat head of the dildo and rubbed some more around his hole. He had just gotten the head past his sphincter, feeling it pop in. The pain he expected before was in full bloom now, but still not so bad, he kind of liked it and was eager to feel go in further.

He was panting excitedly from just the head popping through and about to try to push it in further when…

The front door flew open, and in walked Harriet, who apparently didn’t have to work late, after all. He couldn’t hear her coming in because of the booming bass of the video. It didn’t take her long to assess the situation including the kind of porn he was watching and that he had found her new toy and was trying to shove it up his ass. Not to mention her dirty panties on his bottom.

“Sal! What the fuck?!! I mean, what in the actual fucking fuck!? You know what… don’t even bother.” Sal got up on his knees from his (trying-to-get-a-huge-dildo-up-the-ass) crouch. His asshole gripped the head, with the rest of the heavy rubber phallus dangling out of it. When he straightened up the big fat dildo with its huge balls, too heavy stay in, fell out onto the floor with a wet embarrassing squelch.

“I can’t! I just can’t.” Harriet cried out.

Before he could formulate a response, or even dissociate from her enormous dildo, trying to stop the video, Salvatore inadvertently hit its remote control and the thing came alive and now writhed, slithered, and buzzed on floor behind him. This seemed to be the last straw for Harriet, who re-opened the door and disappeared, leaving poor Sal in the worst state, though he had been more than halfway to the sissygasm he had recently become so obsessed with.

Sal spent the whole weekend sending desperate texts and leaving voicemail messages for Harriet, with no response. He had no idea where she could be, or if she intended on leaving him for good. He was in shock; Saturday and Sunday came and went, without his notice of the world; he lay in bed sucking on his vape pen all day, barely getting up to go to the toilet.

On Monday, he thought briefly about going to her work, but luckily thought immediately better of it. Wednesday morning, he got an ominous text from her. “B by after work. Need To Talk.”

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