Alex glanced repeatedly at his phone in the darkness, careful not to let his eyes stray from the phone for too long. He couldn't believe he was finally on the way to meet Olivia. He had never actually met anyone from the internet before. They started talking about three years ago on Reddit. The two of them had become fast friends, bonding over their shared love of photography.
They made plans to meet once not long after they started talking. She canceled at the last minute, begging off with lack of sleep. Alex wrote off any chance of their ever meeting until a single message on Snapchat changed their relationship forever.
"Have a drink with me tonite?" Her message was simple but implied more. They made plans to hang out at her place that evening. "I'd love to talk about that photoshoot you offered to help me out with. Maybe we can discuss your fees and availability," she added a wink at the end. Alex was very hopeful for the wink.
Three hours later Alex was in the car, showered, shaved, and anxious, headed towards Olivia's house 100 miles away.
"We're not having sex tonite....In case you were wondering," her message halfway through his drive shot Alex down before it was even a consideration. He was still excited to meet her. Olivia had an over the top personality, bursting with energy and oozing sensual charm. Their snaps had escalated over the years until they were sending nudes often. Alex had gotten his hopes up that he might actually hook up with this voluptuous older woman.
Olivia was a former model who was a little down on her luck. 45 and single, she had a kid in college and bills were stacking up. She lost her job during Covid and was struggling to catch up in a changing economy. Free spirited and open, she was considering joining the internet sexual revolution. Her more risqué friends kept whispering about how much money so-and-so was making on OnlyFans taking photos while they were alone during the day.
It was 9:30 at night before Alex pulled into the driveway of a small concrete block house in the middle of nowhere. A bare bulb lit the small porch off the side door. Her last message said to knock on the side door and present his offering. What the hell had he gotten himself into? He could easily lose a kidney in a place like this...
He grabbed the bottle of Ron Zacapa from the backseat and hopped out of his SUV, taking long strides towards her door before he changed his mind. He reached the door with a small curtain covered glass and knocked softly, steeling his nerves for what might lay beyond. The curtain moved slowly and a shadow peered out at him. Alex raised the bottle of spiced rum and smiled a goofy smile, hopefully optimistic.
Alex wasn't ready for the being that opened the door. Olivia's photos did her very little justice. While he was sure it was the same person he had been conversing with for so long, everything about her was sexier than he could have ever imagined.
"Oh my god, you are stunning," he blurted out, unsure how to break the ice.
"Hi Alex!" She cooed. Olivia's voice was softer and higher than he had expected. She was about 5'6" and 150 pounds, curvy and womanly in every way. Her light hair was somewhere between blonde and brown, dark curls wet as if she were freshly showered. She wore a thin airy dress, freckles visible on her pale Scottish chest where her bountiful cleavage was on display.
Alex opened his arms wide and she stepped in to embrace him, laying her head sideways against his chest. He felt her soft tits mash and spread between their bodies, leaving no doubts as to whether or not she wore a bra. "Its so nice to finally meet you, Olivia!" He exclaimed. "You're even sexier in person!"
"Come inside and get comfy!" She offered, squeezing him tightly before stepping aside to let him into her home. "I thought we'd hang out in here. Let me grab some glasses and ice." Olivia gestured him through an open doorway before heading towards what Alex assumed was the kitchen.
Alex was surprised to be in a bedroom. He hoped it was Olivia's bedroom. Sets of lingerie of various colors and degrees of laciness were strewn about haphazardly and three pairs of heels sat on the end of a queen sized bed. A floor length mirror stood in the corner draped with string lights. The room wasn't necessarily messy, but it was clear she hadn't tidied up on his account.
"Well don't just stand there, have a seat on the bed," Olivia suggested, returning with two tumblers loaded with ice. "Sorry I live like I'm in a frat house." Her apology was more an explanation than an excuse, with no remorse implied.
Alex made himself at home, sliding some of the lingerie to the foot of the bed to clear a spot for them to sit. "I like this jade green color," he commented, testing the waters. "I bet it goes great with your eyes."
"Oooh, that's one of my favorites!" Olivia offered, not making it weird that Alex was touching her lacy bits a mere ten minutes after meeting him for the first time. "I picked out a few sets I thought might photograph well. But I'm open to suggestions. I'm not really in the mood to shoot tonite, but I though we could at least see if we'd work well together."
So much for the car full of photographic equipment, Alex thought to himself. Tonite might turn out to be quite the bust. At least he was putting himself out there and meeting new people. It was a numbers game, right?
"I hope rum is ok," Alex offered, cracking the lid on the fresh bottle of top shelf liquor. Before pouring some into a glass. "Mixer?" He asked her, offering Olivia the first taste.
"The ice will melt," she replied quickly as she slid close enough for their thighs to touch.
A glance in her direction revealed a playful smirk. Olivia was something else. Alex poured three fingers into his own glass before taking his first sip, the liquid burning a smooth but fiery trail to his belly.
"Please don't take this as criticism," Alex started unsurely, trying to tread lightly, "because you are sexier than I could have ever imagined..." His words trailed off as he tried to gauge her reaction. She smiled genuinely, relishing in his attempt at decorum. "But I have a few ideas for poses that I think would be incredibly flattering for you."
"I'd love your input!" Olivia exclaimed, easing his worries. "Want to see some of my old negatives from when I was in my 20's?" She leapt from the bed and raced off, her bare feet echoing off wood floors.
Olivia returned quickly with a vintage portfolio swelling beyond full. Clear binder pages with organized film negatives stuck out haphazardly and loose negative strips dangled comically. Facing him Indian style, they flipped through the negatives together, commenting on most as they looked.
Alex felt as ease, their conversation flowing smoothly. They talked about life, struggles, and dreams. Every time Olivia shifted, Alex was greeted with a view up her dress. Nestled in the shadows just beyond his view, he wondered if Olivia wore panties or if she had thrown on the dress straight from the shower.
Hours passed before he knew it, as one drink turned into two. Alex became more bold, his glances lingering longer between her smooth thighs.
"Eh hem..." Olivia clearing her throat woke Alex from his daydreaming. "My eyes are up here. And I already told you that you're not getting any tonite, mister!"
She shocked him before he could apologize for his wandering eyes, hooking the plunging neckline of her dress with her pointer finger and slowly sliding it to the side until her hard, pink, pencil eraser of a nipple sprung free of its confines.
"You have my undivided attention," Alex assured her.
"Come on!" Olivia enthusiastically prodded, leaping to her feet and twirling a full circle in front of him. "Dance with me!" The bottoms of her ass cheeks and a hint of her cleanly shaven pussy flashed beneath her spinning dress, disappearing almost before Alex could register what he was seeing. Her natural breasts swung braless, her hardened nipple still free of her dress.
Alex had a buzz by now, his inhibitions about dancing long gone. The idea of this scantily clad MILF in his arms was all the motivation he needed to let loose. Olivia turned up the radio slightly and began to sway softly, a 90's Portishead song he recognized playing from the speakers but not drowning out their voices.
