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Rated: 18+ · Book · LGBTQ+ · #2346254

Joe Farelli had always chosen the wrong women. He bounced from one break up to another.

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#1097610 added September 22, 2025 at 3:19pm
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Best sex, worst sex, Heather
Joe drove home through heavy traffic; the hour was late, but the summer sun still had some bite. He could feel its intensity burning into the backs of his hands as they rested on the steering wheel. It was late August, and the summer would soon be over. He hadn't done a single fun thing this year, and he wasn’t going to count the winery tour he and Rhonda had gone on last July. All they had done was bicker as their relationship had dissolved.

The commute used to take ten minutes; now it was more often twenty-five, with all the roadworks and new construction. Many people were moving here; it was a popular city to live in. He glanced down from the top of the bridge as he crossed the busy freeway. Splashes of vibrant color caught his eye in the trees far below. It was not the annual state fair or the circus come to town, but rather something less cheerful. The swell of the homeless and their tent city had begun to take over the parkland. With the inflation of the past year and the state of the general economy, he was hardly surprised.

He flicked on the radio to try to steer his thoughts onto something more pleasant, and all he got was more political commentary with the elections only being a little over eight weeks away. He turned it off almost as soon as he had begun to listen. All this gloom and doom was the last thing he needed going home to his almost empty condo, if he didn’t count the terrible company of Salt.

Joe’s salary used to be considered substantial, before the erosion of inflation had bitten deep. He had found it easy to buy a new car, pay his rent, go on nice holidays, and buy smart clothes. The plan had always been to purchase his own apartment, but now, with how much everything cost and the spiraling interest rates, that plan had long ago been shelved. He had even thought about moving to a more modest address, but he could not bring himself to do so. That would be to admit he had failed. He liked where he lived, and considered it a perk of his good job.

The maw of the parking garage loomed cool and dark. He was glad to be out of the harsh sunlight. Joe pulled into his allotted parking space, took off his sunglasses, and headed up to his fourth-story apartment. The first thing he did was throw his suit jacket onto the floor, loosen his tie, and flop down onto his sectional lounge. He closed his eyes and enjoyed the almost silence. Though the hum of the metropolis was ever-present in the background.

He didn’t really feel like spending the evening here alone. He opened his slate gray eyes and looked about, as he suspected Salt was nowhere in sight. He was a user that cat. The ladies at the shelter had told Joe he was loving and enjoyed cuddles. He guessed they had lied. He was probably skulking behind the toilet or on the bottom shelf of his computer desk. The creature did little else except to demand food.

As it was Monday, only some of the local bars would be open, and he pondered getting freshened up and going for a stroll downtown. However, he had never picked up a viable date on a Monday. He sat up and went to the kitchen to peer into the fridge. All that greeted him was a stale-looking piece of Domino's pizza in its greasy box and an open tin of cat food.

However, in the freezer, there was a microwavable meal. Sweet and sour chicken with rice, that would have to do. He spooned out Salt’s rather stale-looking cat food, reminding himself he would have to go to Pet Smart tomorrow, because Salt refused to eat any of the brands of food that could be readily acquired at the corner store run by immigrants. That cat sometimes really had the nerve.

Monday, yeah, he’d never picked up a decent date on a Monday. The chime of the microwave roused him from his reverie, and at the same moment Salt came striding in, meowing for food. The only time that lazy cat ever seemed animated. As Joe took his meager dinner into the other room, he suddenly remembered the first almost fuck of his life had been on a Monday. Her name had been Heather.

Joe hadn't always been a city dweller. He had been raised in a small country town of only four hundred or so people. He had attended this quaint little school that sat on the top of a hill with only seventy students. He knew everyone in the town on a first-name basis. Most of those names were still etched indelibly into his memory. Especially hers, the girl who had popped his cherry, Heather.

Now, Heather was a big, solid girl, one you didn’t get in a fight with. Not without ramifications anyway. She was the first girl in his class to develop noticeable breasts. So even though she was hardly the most beautiful girl in class, many of the boys were enamored. In late elementary school, she already sported C-sized breasts that had seemed to have sprouted overnight, and by the time she finished high school, those breasts were a magnificent, all-natural triple H. Joe would always look at them straining at the fabric of her dresses, and wonder what it would be like to bury his face in that. His love for bimbos had blossomed.

Joe wondered just how long it had sat there in the freezer. He had, of course, already discarded the package and hadn’t read the expiry date. While he ate this unappealing dinner, Joe meandered through his now somewhat hazy senior high school memories to a past he rarely visited. It was at the school prom that he had first made his intentions to Heather clear. From that moment on, there was a lot of kissing and holding hands. However, he still had not gotten to first base. That would come later, during college, on a wet and dark wintry afternoon. The day he first saw her naked.

She was a shy kind of girl, Joe suspected. She wasn't fond of her plus-size appearance and didn’t understand the power that those breasts had. The moment they flopped out of the enormous beige bra, Joe was held in Heather’s thrall. He could not look away. Heather no longer had a face; all that existed for him was the soft rolls of a milky white cleavage. He wanted to bury his face in her luscious folds and never return to reality.

As Joe looked at Heather in all her topless glory, he thought, ‘This is the one for me, my Mrs Right.’ He was at that moment, even though he was totally unsure of quite what to do next. Ecstatic that he had found his ‘One’ so early in life. Of course, the couple both had zero sexual experience, and the ensuing sex was a fumbling disaster. However, that didn’t matter to Joe; those immense breasts were everything.

Big voluptuous Heather just lay back on the bed, a canvas for Joe’s big-breasted worship and fixation, as the late afternoon rain beat against the windows. He did spend a long while before venturing onto the rest of Heather's mystery. He just could not get past the wonder of those huge mounds; they were even more surreal than he imagined. Just the sheer weight of them in his hands, purely unbelievable!

He’d just recently read a very kinky novel one of his buddies had lent him, it was called Screwed Up. He could not remember the author, but it was full of some really good masturbation material in lieu of the real thing. He had read about oral sex, and he had decided he would try it today.

With that expectation, rather clumsily, Joe helped Heather remove the rest of her clothing. She seemed to be enjoying herself, even with his fumbling inexperience. Working with Heather out was almost like trying to use an old operating system like Mac OS 9. Scary, and vastly unfamiliar.

He plunged his face between her solid thighs and hoped for the best. At least she had shaved. She tasted salty and earthy, so not terrible, but not at all what he had expected either. He didn’t know what flavor he had anticipated her to be, but not the one he tasted anyway. At least she was wet, so that was a good sign. He must be doing something right. Though he was unacquainted with the female anatomy and how it worked exactly, or what to look for. Honestly, at this distance, he couldn’t see a thing. So he sloshed about with his eager tongue and hoped for the best.

Heather was stroking his chestnut curls and softly moaning, and he could feel his manhood hardening, and that urgent, fractious feeling of need rise so powerfully. Awkwardly trying not to disengage his probing tongue from her hot, wet sex, he wrestled off his jeans to free his now throbbing member. He was almost shaking with excitement. Home base was so close, not quite the well-choreographed scenarios in the Screwed Up novel, but it was his to own.

It was then that Joe had this terrible dilemma. He wanted to fuck those breasts so hard, far more than he wanted to penetrate that hot pussy between those thicc thighs. He paused for long moments, and Heather looked up. She was still gently caressing him. However, she was not much more than a passive recipient of his passions. He guessed she didn’t know what to do either, or perhaps that’s all women did during sex? Though the books he had read, and the few porno's he had watched, suggested otherwise.

Damn it, he could get to home base later. Those enormous mounds were the real lure, and he straddled her at once, pushing his hard cock into the deep cleft between them. It was warm and all-encompassing, surrounding his excited member, pure heaven; he was in his element.

Joe closed his steel gray eyes and let the feeling of envelopment overtake his sensibilities. He arched his back and groaned as his release came powerfully, and all too soon. He had hoped to fuck her tits for a time and then pop her cherry. On this dark winter’s day, it was not to be.
Heather sat up, her light blue eyes housed questions, and she was possibly a little distressed. “I thought we were going to…” She began to say.

“Yeah, sorry, I got a little carried away.’ Joe said sheepishly, planting an apologetic kiss on her lips. He was annoyed that he had finished long before the job was complete. Next time, he would get it right. Because those breasts were Mrs Right, and there would be a next time.

It was then that he made his inglorious mistake; he should have shut his mouth. “Did you cum?” He asked, trying to be courteous as he stroked her silken, light brown hair.

“Almost, but not quite,” Heather replied, cinching up her bra.

Joe wished that she had left those breasts free to roam free for a while longer. As he was still very much enjoying the scenery. He could tell by the inflection of her words that he had well and truly missed the mark, but he’d study up and hit the right spot next time, right?

“So how was it?” She said, looking for his approval. It had, after all, been a first for her as well, her pale blue eyes on him intently in the fading afternoon light.

“Well, it sure didn’t taste like roast beef!” Joe could not help but say, and one look at her face as she rapidly pulled on her disheveled clothing told him his attempt at humor had fallen far wide of its mark.

He tried to apologize as she left his flat, and after that, she broke it off. Those wondrous breasts were now forever denied him. However, the allure had never died, and with the exception of the lazy Vita, every woman he had dated wore highly engineered bras.

After his uninspiring dinner and the remembrance of his first time, Joe decided he would stay in after all. He didn’t expect a heavy work day tomorrow, but that could all change in an instant. Perhaps a long hot shower followed by some time with Mrs Palmer and some sexy busty videos before bed.

The shower had calmed some of his prior friskiness and eased the tension in his shoulders and neck from the long days of sitting at his desktop. He didn’t feel like playing computer games; in fact, tonight the last thing he felt like was sitting at the computer hunched over his keyboard as he had done all day. He should have taken a walk, or spent time on the expensive stationary bike that was all the craze, but he did neither. He didn’t know why he had purchased the thing, but it had seemed like a good idea in the moment. All he did was look at it.

So he decided to go to bed and get an early night, settling under the puffy white duvet, and with that, thoughts of Rhonda flooded his mind. She had chosen this thing after all. He threw it off the bed and got up to get his old dull green one from the top of the walk-in closet, the one she had called an eyesore. Possibly it was, as it didn’t go with a single thing in his bedroom, but it was his. He threw it on the bed and pet Salt on the top of the head as he passed. Salt barely acknowledged the attention, just like all those women online never acknowledged or even read his messages of introduction.

Even so, he sat once more browsing dating sites for Rhonda’s replacement. He was these days very specific with his ‘type.’ She must have the hourglass figure, and a dramatic cleavage, the more top-heavy the better. Not only that, but she also had to want to show it all off. Not at all like Heather, who kept it all covered and held in at every opportunity. He had learned a lot over the years, and he knew she was out there somewhere. He must never give up.
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