All characters are 18 or older.
This is my first attempt at a story like this. Feedback, suggestions and kindness are welcome.
*
Sitting on his flight to reunite with his father on the west coast, Josh wasn't thinking about the fact that he was moving across the country. His mind wasn't on his college career, set to begin in a couple of weeks. He wasn't even really thinking about the life - high school, long-time friends, his mom - that he was leaving behind.
Josh was thinking about his new stepmother. Specifically, his new stepmother's tits.
He wasn't expecting Darla to even be his new stepmother when he met her the first time a few months ago. She was another in a long line of his dad's increasingly younger girlfriends - all of them beautiful, poised women, sophisticated in their way but also with young, lithe bodies. Expensive hookers, his mom had always called them. Darla seemed no different.
When Josh's parents divorced when he was little, he stayed with his mom on the east coast. His father David was a high-powered lawyer for a large international firm who travelled a lot for work. He was a good provider, and Josh and his mother didn't want, financially, when he was growing up. When David relocated across the country - for convenient access to increasing business in Asia, not to mention easy access to young, beautiful women and the warm weather that attracted them - Josh saw less and less of his father. More than a handful of times, cross-country visits had been cancelled or delayed by his father's changing plans and last-minute business trips.
When Josh visited this past spring, however, his father had a proposition for him. And to Josh's shock, so did David's new girlfriend.
There'd been a lot of women that paraded through David's bed, if not his life, in the ensuing decade-plus since the divorce, but Josh hadn't met too many. Fewer, it seemed, since he hit puberty; an insolent teenager was less of a panty-dropper to David's prospective conquests than the adorable moppet of a nine-year-old he'd been.
As he sat in the plane on the way to his new life, Josh reflected on that first meeting just a few months ago.
Darla and his father were already at the restaurant when Josh arrived. David waved him over to their quiet corner table, but Josh barely glanced at his dad. Beside him was the most beautiful woman Josh had ever seen in person - Darla had long, curly blonde hair that cascaded down her bare shoulders like a shampoo commercial. As she stood to greet him, he saw she was wearing an expensive-looking red dress - a halter-style top barely covered her breasts and her bronze, beautiful legs were exposed by a very short hemline. Darla tugged the dress down with a giggle as Josh approached, and as she opened her arms wide with a little shriek to greet him with a hug, he drank in the vision of her spectacular breasts. They were big and perfectly shaped, far from the cartoonish balloon boobs Josh had masturbated to in various porn, but amazing enough that he wondered if they were real. They certainly defied gravity - the plunging neckline of her dress exposed perfect half-globes unsupported by any visible bra. This amazing display of cleavage was made even more tantalising by the possibility - the likelihood - that any move Darla made might pop a tit right out into the open.
Josh's brain was sending signals exclusively to his cock as he took in the vision before him. The vision coming right at him. The vision that made a high-pitched noise as she pressed her body against his as if they were long-lost lovers separated by wartime.
"I'm so excited to meet you!" Darla told him without letting go. Her boobs were squished against his body and his cock continued to swell. Instinctively, he hugged her back, his arms wrapping her thin waist. Darla was tall, Josh thought to himself, almost his height - he realised that his hugging arms weren't halfway down her back like they would be on a smaller woman - in fact, his hands came to rest across the small of her back, just above the next thing he noticed, the shape of her incredible ass. Darla continued to hold him, murmuring her excitement into his ear, while he looked down her back at the curves that swelled behind her.
In that instant, he forgot that he was hugging his father's new girlfriend; his body was simply reacting to the sexiest woman he'd ever touched - the press of her breasts against his chest, the way she snuggled his neck and he could feel her hot breath, and, as he moved his hands down her back, the contours of her booty. His erection swelled further and he was sure that Darla could feel it poking into her hip through the khakis he'd chosen over his regular jeans-and-hoodie combo.
"Okay, you too, that's enough," Josh heard his father saying, laughing. Did the hug last more than a couple of seconds? He couldn't tell, and when he replayed this moment later, repeatedly, often while he stroked his cock, he extended and savoured every detail. The neckline of the dress, the bounce of her breasts when she stood to greet him, the tug-and-giggle modesty of the dress that rode up her spectacular legs, and of course the hug, all deposited in his spank bank.
"David, you didn't tell me your son was such a stud!" Darla said, turning without fully letting go of her grip on Josh. One hand remained wrapped around his back, where she clasped his arm and held it in place, ensuring that his hand remained resting on the top of her butt. She ran her other hand across his chest. "He's so handsome!" she added playfully. Josh wasn't a star athlete by any means, but ten years on the swim team had given him a lithe, muscular physique.
"Keep your hands off my son," David said playfully as he moved in for a hug of his own. They didn't have a particularly close relationship, father and son, but it was affectionate enough and David liked to keep up appearances of closeness that were driven by financial generosity more than actual time spent together; it didn't bother Josh, who'd grown used to both the amenities and the absences his father's success entailed.
"You must be starving," David said as he gestured for everyone to sit.
Josh responded that he was, and Darla piped in with an enthusiastic "Me too!" David didn't see that she locked eyes with Josh as she said it. "I'm desperately famished," she added, while her hand absentmindedly stroked the edge of her halter dress, fingers delicately brushing across her full breast. She licked her lips, never breaking eye contact with Josh.
David gestured for them to sit in a U-shaped booth in the corner. Josh moved into the middle, with his father on one side facing the restaurant, and Darla on the other, completely hidden from view by the height of the divide behind her.
Darla was, somewhat to Josh's surprise, completely delightful and seemingly not a gold-digging bimbo at all. Smart, witty, well-read; she worked as a paralegal and had started dating his father a few months ago. She laughed easily and flirted openly with both David and Josh. His father didn't seem to mind, and it was a dynamic that Josh was not unfamiliar with. There had been plenty of younger women in his dad's life over the last few years and the attention he would receive had evolved in the last three or four years, from pats on the head to flirtatious looks. But Darla was on another level completely.
Josh wasn't sure he'd ever been this close to a woman so stunning, and as much as he forced a voice in his head to repeat, on a loop, "don't look don't look don't look," he looked. Darla's breasts were fascinating to him, large and pendulous like a sexy teardrop, but also perfectly firm and in place behind the thin material of her red dress. Josh couldn't distinguish any visible tan lines around these mysterious globes, yet they were a consistent light golden colour. When she laughed, easily and often, it was with her whole body, and both tits jiggly gamely against their restraints. Her nipples were hard and clearly strained against the halter top, but what really captivated Josh's attention was a tiny detail - a bump, or maybe a circle, below or around her nipples.
"Joshua, it's rude to stare." He heard his father's voice suddenly, and he started back to attention.
"I'm so sorry," Josh stammered, "I was just lost in thought."
"Nevermind what you were lost in," David responded. "I was just saying that I have to take a work call for a minute. Do you think you can manage to entertain Darla?"
"Oh absolutely."
"Try to be charming, don't just gawk at her Josh," his father said with a laugh as he stood up. He gave Darla a quick kiss, followed up by a more enthusiastic one, and gestured to the waiter, who guided him to a room nearby for privacy.
"So you like them?" Darla asked Josh directly. She had a mischievous look.
"I'm sorry?" Josh asked, embarrassed that he'd been caught staring.
"My tits. You like them?"
"I'm sorry," Josh found himself saying again. "I didn't mean to stare, I feel terrible, I was just curious about..."
Darla turned in her seat on the beach and looked directly at Josh. She grasped the edges of her red halter top above her boobs and slowly slid her fingers down toward her cleavage. She pulled the fabric apart as she went, exposing more of her breasts until the seams caught on her engorged nipples. "Oops," she giggled, looking down; she spread the fabric completely, freeing the nipples, and cupped her hands under her tits, lifting them up as if she were offering Josh some dessert.
Dangling from each erect nipple was a ring with a diamond swinging from the bottom of it; the piercings themselves gave Darla's nipples an extra boost, it seemed. That was the shape Josh had been trying to discern beneath the fabric. He felt his cock, hard in his pants.
"It was nipple rings," Josh blurted awkwardly.
"What?" Darla laughed. It was one of the more curious responses she'd ever had to showing someone her boobs.
"They're amazing. They're the greatest things I've ever seen," Josh continued. "But I... I mean, my dad." He still couldn't stop staring and Darla giggled again, amused that she was able to entrance him so easily,
"Your father loves them too. What about nipple rings?" she asked, feigning innocence. She made no effort to cover up, and in fact, she encouraged Josh's attention. Her hands bounced her breasts a little more, and the rings jumped in time.
"That's why I was staring," Josh tried to explain, as if his attention was somehow innocently clinical and not lascivious. It wasn't convincing. "I saw the outline of the rings through your dress and I couldn't make out what they were."
