Author Note: This is another "Quick Stroke" story. Less world-building and character-building, quicker jump into the action, meant for...well...quickly getting off. This is the second short story I've done, I'm still experimenting with this style in between larger chapters of my other work. Hope you enjoy it.
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"So, tell me again who I'm supposed to play tonight?" Michael asked from the driver's seat. He was focused on the road as they drove downtown to a pub close to where Jennifer worked.
Jennifer felt herself grow wet at the question and subconsciously rubbed her thighs together, "It doesn't matter. That's the point really. Just some random person, some stranger taking what they want in a dark alley."
She ran her hand over her husband's crotch, "...taking me."
Jennifer felt how hard he was through his pants. She didn't want to admit out loud the type of person she fantasized about in this scenario. She wasn't sure what Michael would think about his prim and proper younger wife fantasizing about a homeless man taking her, running his dirty hands over her clean body. She shuddered at the mere thought.
"Hmmmm," Michael moaned softly, feeling his wife's manicured fingers teasing his shaft, "I like the sound of that."
"Bad boy," Jennifer responded. "Tonight is about my fantasy... maybe after we can discuss fulfilling yours."
Michael tore his eyes from the road to quickly look at his stunning wife. "Uh, really?"
She continued to lightly stroke his shaft while staring deep into his eyes. "We can talk about it. If we find the right guy for the job, I'll consider letting it happen while you watch."
To date, both of their fantasies had stayed strictly in the bedroom, but with some encouragement tonight they were acting out hers. The least she could do was consider his. He knew it would still take a bit of work to get her there.
She could tell her husband was getting very aroused from the sound of his breathing, and the way his eyes were roaming her body. "Eyes on the road, mister."
Her husband tore his eyes from her and focused them back on the road in front of them. For the rest of the drive, he was lost in thought.
They pulled over into a small parking lot next to Jennifer's office building. It was a nice summer night, warm but not too hot. Jennifer was wearing a loose black dress with spaghetti straps that ended mid-thigh, showing a lot of smooth leg. The tops of her breasts were on display, pushing against the material of the dress, threatening to spill out for all to see. Her long-toned legs were framed by the black stiletto high heels she wore.
Michael rounded the back of the car and took Sarah's hand as they began to walk towards the pub. He was dressed in jeans with a simple polo shirt.
As they crossed the parking lot a figure was shambling in their direction, weaving between the cars. The young couple tried to ignore the homeless man who was now in their vicinity. A horrible hacking cough emanated from the rough-looking individual. "Eh, got any change?"
Jennifer's eyes quickly darted to look the man over. She vaguely recognized him as a local homeless man living on these streets. He was wearing stained baggy sweatpants and old shoes that looked like they were ready to fall apart. His black faded t-shirt was full of holes and stains but was partly covered by what looked like a relatively newer denim jeans jacket. While it looked newer than the rest of his outfit, it was still poorly cared for. The man reeked of booze and had tattoos on one of his hands, a letter on each knuckle that collectively spelled out 'C-A-S-H'. The man's face looked like a leather glove that had been left out in the sun. He had what looked like a permanent scowl covered by white wispy facial hair. He clearly hadn't shaved in the last few weeks and it looked like he had all but given up on his bushy eyebrows. His eyes were intense and desperate, one slightly larger than the other. His look was hungry and focused on her body. Jennifer felt herself sliding closer to Michael, even as her panties grew curiously wet.
"Sorry, mate, no change on us," Michael replied as he kept his body between Jennifer and this older vagrant who was accosting them in the parking lot. He looked to be at least twenty years older than Michael.
They managed to get past him without incident. But, just as they had gotten several feet beyond him, he shouted after them, "Yeah! Can't hide any change in a dress like that, what an ass on her. JESUS FUCKING CHRIST!"
Michael tightened his grip on Jennifer's hand reassuringly as they stepped out of the parking lot onto the sidewalk. They could hear the old tramp dragging his feet and muttering to himself as they left him behind.
The walk to the pub was quiet, both of them running through the details of acting out Jennifer's fantasy in their heads.
"Is this the alley?" Michael asked as they stopped before the pub. Jennifer emerged from her thoughts to look down the long alley that ran next to the pub. Although the sun was just beginning to set, the alley already looked dark and dangerous. She'd walked down it years earlier when she had been interning with her company while she was still in college. She'd had drinks with a group of the older women she worked with and the group of them had all heard a noise - it was a woman moaning. Jennifer still remembered her head snapping around to see a homeless couple openly having sex in the alley - as if it was their personal space. The other women she was with had all run away quickly, giggling. In their embarrassed haste, they'd left Jennifer, who was still gawking at the rutting tramps, behind. Jennifer had studiously avoided porn before that, so the sight of this bum fucking a bag lady had been the first time she'd ever watched anyone having sex. The woman had twitched and her head had swung around - and her eyes had locked with those of the young intern. She then screamed a string of profanities as her mouth opened in an almost toothless smile. Jennifer would later realize that she was witnessing the first orgasm she'd ever seen, followed quickly by the second as the homeless man shook and spasmed. The man pulled his member out of the woman and turned to face Jennifer. She remembered thinking at first that it was a large flashlight or club hanging out of his pants.
"You want?" the man said, as he began to walk toward her, his dirty dripping phallus already beginning to harden again. That was when one of her coworkers had returned and grabbed her arm and they had gotten out of there. Jennifer had thought about that question over and over in the years since it was first asked. Did she want? Sex with Michael was good, but something about the street sex she'd seen had continued to intrigue her, maybe even obsess her, over all that time. Lately, there had been more homeless around the area of town she worked in, which is probably what had brought this fantasy flaring back to the forefront of her mind. She'd been toying with it for years now.
From their vantage point, they couldn't see much; the alley's darkness was deeper than the lighting conditions could easily explain, almost impenetrable in its uncanny depth. Despite the warm night, goosebumps ran over Jennifer's skin as the time for committing to her fantasy drew nigh.
"Yes. This is it," Jennifer finally responded to Michael's question. "Let's head inside and grab a booth."
***
Meanwhile, the bum whose tattoo identified him as 'Cash' shuffled through the parking lot, trying the handles of each car he passed. The first one he tried was locked, so he relieved himself on the car door out of spite. After a few more tries, he finally found one that was unlocked and he slid into the driver's seat. He rummaged around the contents of the glove box and found a pack of cigarettes, a lighter and some change.
He immediately lit up a cigarette, letting the nicotine wash into his system. He grabbed a battered steel flask from the breast pocket inside his denim jacket and took a long swig. Cash took another drag of the cigarette and exhaled into the cab of the car, smoke settling into the fabric.
