[Insider] Homeless Alley Short Story

Finally, the first rough draft of the last short story vote is here. If you are new or don't recall, the Insider tier voted on short story concepts for me to write. The winner was this one, about a homeless man taking a husband's place in an urban back alley. 

It took a little longer than I had planned to get this one out but here it is. I hope you enjoy it. As always here at the Insider tier you are getting this immediately following me finishing this first draft - which means you get all the grammar errors and ugliness before I do any editing. 

As some extra interest here. Our heroine of this story, Jennifer, is based of a real person who is a big fan.....

Homeless Alley is just a working title, I'm open to any suggestions you might have.

Without further ado....

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“So tell me again who I’m suppoed to play tonight?” Michael asked from the driver’s seat. He was focused on the road as they drove downtown to a pub closed to where Jennifer worked.

Jennifer felt herself grow wet at the question and subconciously rubbed her thighs together, “It doesn’t matter, thats the point really. Just some random person, some stranger taking what they want in the 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 fullfilling yours.”

Micheal 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.

She could tell her husband was getting very aroused by his breathing, his eyes started to roam her body, “Eyes on the road mister.”

Her husband tore his eyes from her and focused back in front of him. For the rest of the drive he was lost in thought.

They parked in 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 spagetti straps that ended mid-thigh, showing a lot of smooth legs. The tops of her breasts were on display, pushing against the material of the dress, threatening to spill out for all to see. He long toned legs were framed by the black stilleto high heels she wore.

Michael rounded the the back of the car and took Sarah’s hand as they began to walk towards the pub. He was dressed in a simple polo with jeans.

As they crossed the parking lot a figure was shambeling in their directed, 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 indvidual, “Eh, got any change?”

Jennifer’s eyes quickly darted to look over the man. She vagely recognized him as one of the local homeless men who lived 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 jean jacket. While it looked newer than the rest of his outfit, it still wasn’t well taken care of. The man reeked of booze and had tattoos on one of his hands, a letter on each knuckle that spelt 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 permenant scowl covered by a white whispy facial hair. He clearly hadn’t shaved in a few weeks and it looked like he had all but given up on his bushy eyesbrows. His eye’s were intense, desperate, hungry and focused on her body. Jennifer felt herself sliding closer to Michael, even as her panties grew wet.

“Sorry mate, no change on us,” Michael replied as he kept his body between Jennifer and this older homeless man passing them in the parking lot. He looked to be at least twenty years older than Michael.

They passed him without incident. As they were several feet away, he shouted at them, “Yeah! Can’t hid any change in a dress like that, what an ass on her. JESUS CHRIST.”

Michael tightened his grip on her hand reassuringly as they stepped out of the parking lot onto the sidewalk. They could hear him dragging his feet and muttering to himself as they left the old tramp behind.

The walk to the pub was quiet, both of them anticiapting acting out Jennifer’s fantasy.

“Is this the alley?” Michael asked as they stopped before the pub. Jennifer looked up from her thoughts down the long alley than ran next to the pub. The sun was beginning to set but the alley already looked dark and dangerous. She’d walked down it once, after a couple of work drinks with some female coworkers. They’d been catcalled while they quickly moved through it, which is probably what ignited this fantasy in her mind. She’d been toying with it for years now.

From their vantage point, they couldn’t see much, it was like the darkness was impentrable to their eyes. Despite the warm night, goosebumps ran over her skin in ancitipation.

“It is,” Jennifer finally responded, “Let’s head inside and grab a booth.”

***

Cash shuffled through the parking lot, trying the handles of each car that he passed by. One was finally unlocked and he slid into the driver’s seat and started to rummage around the contents of the glove box. He found a pack of ciagrettes, 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.

Cash’s grubby hands settled onto his hardening cock underhis sweatpants. He reached under the waistband and began to stroke it in this stranger’s car. He was thinking about the sweet pair of tits on that young woman in the black dress, how they were almost spilling out on display for him. And the sway of her hips as she walks away and the way her black dress fell on her perfect ass. He swore he could rest a drink on that thing.

He recognized her immediately but never saw the guy she was with before. He’d seen her several times out during the day with other well-to-do women who ignored him when he would catcall or ask for change. He’d rubbed more than one out to her over the past few months. He was thankful he now had more material to use.

Cash settled back into the seat of the car, with the ciagretta hanging limping out of his mouth, he began tugging his cock thinking about the brunnette in the black dress.

***

Jennifer and Michael had been sitting in the bar for over two hours. Several pints had come and gone and both were feeling the effects.

Michael took a long drink of his beer and looked across his glass at his wife. She was giving him her ‘fuck me’ eyes and he knew it would soon be time to enact her fantasy. Did she really mean what she said. Would my fantasy be next?

“So,” Jennifer mewed as she seductively ran her fingers along the rim of her empty glass, “Let’s just go over it one more time.”

She raised a suggestive eyebrow at him and looked deep into his eyes. Her piercing green eyes always made his heart skip a beat, “I’m going to go down to the backhall way and slip out the door to the alley. You count to sixty and then come find me. I’ll be bent over, waiting for you to come take me.”

Michael gulped and took another large sip of his beer.

“I don’t want any sweet talk, nothing. On second thought, don’t say anything, just come up behind me and shove it in and fuck my brains out.”

“Oh, I can do that.” Michael subconciously ran his hand over the pocket in his pants. He felt the outline of the condom. He’d have to figure out when to slip it onto his cock between the door from the bar and when he got behind her. He was always quite careful about making sure they didn’t end up with any surprises, maybe in a few months when work settled down they could resume talking about starting their family.

Michael didn’t bring up the condom. He knew it would ruin the mood as it had been a sore subject in the past. Jennifer had been annoyned at his insistance to keep using it, even after they were married. She said she just wanted to feel his passion, for him to lose himself for her, consequences be damned. That had been a few months ago but he still knew to tread lightly. He hoped his use of the condom didn’t detract from her fantasy tonight.

“You going to finish that drink?” Sarah licked her lips and looked at him like a piece of meat.

“Yes ma’am” Michael replied and downed the rest of his pint.

Jennifer smiled and stood up, bracing herself against the table as she discovered what the drinks at done to her equilibrium, “Count to sixty and them come find me.”

With that his wife turned on her heel and walked across the crowded bar until she was out of his sight. Michael took out his cellphone and watched the time, staring intently at the device until the next minute appeared.

Michael rose, trying to conceal his rapidly hardening erection as he moved towards the back area of the bar. As he was about to round the corner a heavy scottish voice rang out behind him.

“Oi! Bucko. Not gonna dine and ditch are ye?” Michael spun around to see the beefy bartender leering at him.

“No, just going to hit the head,” Michael started to turn back towards the toliets.

“And what about the lass of yours? Where’d she disappear to? Tell you what, come over her and settle your tab and then you can go take a piss.” The bartender demanded.

“Okay, fine,” Michael said taking his wallet out and moving to the bar. “Let’s just be quick about it.”

***

Bent over a stack of long forgetten pallets, Jennifer waited with anticipation for Michael to come take her. She’d stumbled upon this alcove after carefully navigating the dark alley. She was a few yards down from the pub’s exit to the alley, away from the streetlights. Hopefully it wouldn’t be too difficult for Michael to find her in the dark.

She heard the sounds of slow, shuffling feet coming in her direction. Michael was getting close. She bit her lip and subconsiouly thrust her ass out a bit more, her manicured nailed gripping the wood of the pallet. She dug her heels into the alley’s ashpalt, bracing herself for what would come next.

The footsteps stopped close by. He must have spotted her. She knew how apetizing the view of her bent over and waiting for him must be. The footsteps resumes quicker now until they stopped just behind her. She couldn’t see him, but she could feel his presence.

She felt the warmth of fingertips graze the outside of her thighs as her husband started to raise her dress. Jennifer felt the night’s air touch her naked ass cheecks as Michael raised her dress higher.

She gripped the pallet tightly, and hung her head, completely giving her body up to her husband. His thumbs hooked under the sides of her thong and started to lower it. Jennifer jumped as she felt his tongue begin to lick her ass cheeks.

Once her thong was hanging limply around her knees, she heard him shuffling behind her. She felt like her pussy was drenched, aching for his cock.

A strong hand pushed on her back, while she felt her husband’s cock push past her thighs and begin to to search for her opening. Jennifer shifted her hips, helping to guide him into her.

Without a whisper of romance, her husband pretending to be a stranger, roughly shoved his cock fully into her.

“Oh fuck,” Jennifer moaned, she gripped onto the pallet harder for support as she started to be roughly fucked in the alleyway. Perhaps it was the alcohol, the situation or the angle they were fucking in but Michael had never made her feel so full before.

Another thought passed through her mind. That’s his bare cock. Finally. He isn’t wearing a condom.

***

Michael watched the ancient debit machine screen spin, processing his card. It was taking forever to process. Not to mention that the bartender had served a couple of customers for totalling up his drinks.

‘Accepted’ finally appeared on the screen and the machine printed out a receipt.

“Alright!” Michael said loudly over the sound of the music and crowd, the beefy baretender’s back was facing him. “All settled up. Have a good night.”

The bartenders peered over his shoulder and lazily waved at him before turning his attention back to the young ladies sitting at the bar.

Michael quickly hurried down the back hallway and threw open the alley way door.

***

Cash’s dirty hands sank into the pale flesh of the hot brunnette bent over in the alleyway for him. He couldn’t believe his luck but never looked a gift horse in the mouth. He grunted, feeling his old cock sliding in and out of the young woman.

Her pussy gripped his cock, trying to pull more of him into her. He wasn’t about to complain.

“Mhmmmm,” she moaned as the tip of his bare cock pushed as far into her as it would go, “Fuck.”

Cash gritted his teeth and smiled. He waited years to prove to himself that he could please one of these priledged woman he saw in his neighborhood and now he was doing it.

“Oh fuck baby, don’t stop, I’m so close. So close,” Jennifer moaned. She could feel her orgasm rapidily building, the fullness of her husband’s cock and dirty alley around her was pushing her body into overdrive.

Cash had the street smarts to keep his mouth shut. He knew she wasn’t bent over waiting for him but he would be happy to beat whoever it was to the punch and drop a load of his homeless cum into her.

He eyes the spagetti straps on her shoulders and quickly began to lower them. Jennifer respond by lazily moving her arms until the straps were down by her sides. Cash grinned and reach around and roughly grabbed a handful of her breasts, while his other hand griped the base of her neck for leverage.

The rough handeling of her body was too much for her. Jennifer’s orgasm finally exploded and washed over her body.

***

Michael peered into the darkness of the alley, unsure which direction to head. He had just exited the door. Down to his left her could see the streetlights and wondered if Jennifer had gone in that direction. To his right it was much darker, he didn’t know if she would risk going down there.

As if on cue he heard a familiar sound.

“Mmmmmmmhmmmmmmm,” It sounded like Jennifer. The sound she makes when he was able to make her cum in bed. She must have taken matters into her own hands as he got held up. The sound came from the darker end of the alley. He moved in that direction, following the unmistakeable sounds of his wife pleasuring herself.

As he rounded a corner and came across a small alcove he stopped dead in his tracks. His heart suddenling beating out of his chest.

Jennifer was bent over a stack of wooden crates as some homeless man was fucking her from behind.

“Oh fuck,” his wife moaned as the man’s cock pistoned in and out of her, “Don’t fucking stop. Uh. Right there. Right there.”

Michael took a step forward and stopped again. He was hear to inact his wife’s fantasy but he had inadvertly stumbled onto his. His brain was having trouble procesing what he was seeing and trying to figure out how to react to the situation. His cock was hard in an instant and he didn’t know how this situation started.

The homless man looked over his shoulder and spotted him. It was the same rough looking older guy from earlier in the night. When he noticed that Michael wasn’t stepping in to intervene, an amused look spread across his face. With a sneer her turned back to Michael’s wife and increased the pace of his fucking.

“Oh, uh,” Jennifer reacted to the increased tempo, she was impressed with her husband’s renewed stamina. The length of his bare cock sliding in and out of her for the first time felt amazing. There was no way she wanted to go back to condoms after this, “Fuck Michael.”

Hearing his name made it all click into place. She thought it was him fucking her, playing the role of the stranger in the alley.

Jennifer could feel another orgasm building, threatening to rip her senses away from her. She started fucking back on the cock hard, desperate to feel it.

Cash wasn’t prepared for the woman to start fucking him back so hard. He loosed his grip on her breast and grabbed onto the pallet for support.

The hand landed in Jennifer’s view. Something in her brain tried to register but her mind was focused on the feeling of the naked cock occuping her pussy. It felt amazing to finally feel a condomless cock.

Something was off about the hand. It didn’t look familiar. Her brain processed something about it. Was there writing on it? C…A…S…

Jennifer whiped her head around to look behind her. It wasn’t her husband there. More importantly it wasn’t her husband’s naked cock inside of her building her to another orgasm. It was that heinous homeless man from earlier. They looked eyes and he grinned at her.

“I knew I’d have you moaning on my cock one day,” He gruntted while gritting his teeth. He roughly pulled down her dress until it was bunch at her mid section. He uncaslped her strapless bra and let it fall onto the ground of the dirty alley way.

“Oh fuck,” Jennifer moaned. The old man’s cock felt so good. Her fantasy was actually happening. Not just a pretend one with Michael. A real homeless man had her bent over in an alley fucking her. She braced herself against the pallet and stared at him, taking in his features, trying to memorize this moment as her orgasm was begining to throttle up.

Then she spotted Michael standing a few feet behind her homeless lover, just watching them, stroking his cock through his pants. She knew in that moment that both of their fantasies were coming true but she was surprised he hadn’t stepped in.

Those thoughts were ripped away as the homeless man’s cock finally pulled another orgasm from her body.

“Mhmmmm. Oh GOD,” Sarah gripped onto the pallet hard for support as a tsuanmi of an orgasm rippled across her body. She felt the muscles in her pussy gripping the homeless cock inside of her. It felt so good. So big. No wonder it felt different. It wasn’t Michael at all.

The homeless hand fodeling her naked breast suddenly let go. It landed the side of her head and roughly pulled her backwards. Jennifer opened her eyes in time to see the man’s face get close to hers, his tongue pushing out.

Without thinking she opened her mouth and took his tongue in. It pushed in and roughly danced across hers. He tasted so different than her husband. Booze, cigarettes and other foreign tastes she couldn’t make out. Jennifer moaned into his mouth as his tongue explored every inch of hers.

Michael stood like a deer in the headlights watching the lewd scene in front of him. His formerly faithful wife was making out with a homeless bum while he slide his cock in and out of her unprotected vagina.

Jennifer moaned at the double invasion, this foreign cock stretching her out and touching depths of her that were vigin territory while his dirty tongue explore her mouth. The tongue retracted and his lips left hers.

Jennifer tried catching her breath as she stared into the eyes of the homeless man. The darkness of the alley did wonders to soften the hard features she had seen earlier in the parking look.

“Good girl,” He chuckled and then forced her back down onto the pallet with one hand while his other held her hip and relentless picked up his speed, fucking her hard and fast with his unprotected cock.

“Oh, uh, uh,” Jennifer mewed to the pallets as she forced her ass back onto the man’s eager thrusts. She knew it was wrong and knew she should be more worried about the situation. Especially because he didn’t have a condom. But those were things she could worry about later, right now she just wanted to continue getting fucked like this.

“Jenn?” Michael said from somewhere close by. She lazily looked over her shoulder and made eye contact with her husband. It was hard to focus on him as her vision blurred everytime the stranger pumped his length into her. “Are you okay?”

She dropped her head. She knew he wanted to watch her with someone else, which is why he hadn’t intervene yet.”

“So good,” she moaned in response to her husband, “So fucking good.”

“Mmm, thats right. Moan for me baby. Moan for my dirty cock,” Cash grunted from behind her, his dirty fingers nails digging into the clean skin of her thighs. “I know you’d be a good fuck ever since I saw you. I wish your friends could you now, bent over and moaning for me.”

The thought of someone seeing her, seeing how far she had fallen to be taken by a back alley bum sent shivers down her spine, “Mhmmm right there. Right there.”

“Heh,” Sweat began to drip off of Cash’s head and land on Jennifer’s ass. “Thats right. Daddy Cash is going to keep fucking you good. Nice and good until I get my nut. Say my name baby. Say Cash. Tell Cash how much you want it.”

Michael stepped closer to the coupling, he was now just a few feet to the side of them. He could see his wife’s face contorted in uncontrolable pleasure. It looked so raw and animalistic. Jealously panged his heart at never having seen her face like this until now.

“Cash,” Jennifer whimped, “Oh, fuck. CASH.”

Hearing his vile name escape her pretty lips had Cash move into overdrive. He could feel the sensation of tingeling begin in his nutsack.

Michael could see the tell tale signs of the old man working himself up to cum. A thought strayed into his mind.

“Are you wearing a condom?” He asked. Cash ignored him and kept up his pace, desperate to release himself.

“No….” Jennifer grunted as she felt Cash’s cock press against her cervix. “He’s not….”

“Baby?” Michael got a step closer and felt the heat emanating from the contray couple. “Hey baby? What did you say?”

Jennifer looked up at him, her mascara mixed with sweat running down her face, “He’s…Noo condom Michael….he isn’t…baby….not…ughh” Her sentance was interrupted as Cash thrust hard against a sensitive area, causing her body to jerk. She felt another orgasm quicklly rearing its head, threatening to over take her senses, “He’s fucking me bare….Michael….ugh……fuck….its not a good time…..the worst time. Oh fuck.”

Cash started picking up his speed, desperate to cum in the young wife bent over in front of him. He could feel her pussy gripping his cock, wanting milk out every last drop of his cum.

Michael finally comprhended the full gravity of what she was saying. He turned to the homeless man and put a hand on his shoulder. He immediately retracted it, not wanting to touch him and his dirty clothing, “Hey man, stop, don’t come in her, okay?”

Cash didn’t look at him, he focused on the sweat dripped off this woman’s back. He reached around and grabbed a handful of her heaving breasts and tweaked her nipple, elicting a loud moan from her. She was thrusting back her hips in time to meet his. She was going to come any second.

“Fuck that,” Cash declared loudly to the alley way. “I’m cumming! Take it bitch.”

“Uh, Cash,” Jennifer moaned of her own volition.

Time slowed for Michael as he watched the couple push into each other. The homeless man’s face groan in ecstacy as his balls emptied and he blew his hot load of cum deep into his wife’s feritle pussy, something Michael had never done.

For all of Michael’s diligence around family planning over the years, he was now watching his wife milk the cum from a disgusting tramp.

“Oh fuck, FUCK,” his wife’s loud moan snapped him out of his. “Oh yes. Fuck.”

Jennifer’s body convulsed, her pussy gripping the cock of the unkempt man behind her. She felt his hot cum spray against her insides, washing over them. Her body reacted on a primal level. She came immediately feeling a man’s cum inside of her for the first time. Something clicked into place in her mind that it just felt right. She groaned as she pushed her hips back against Cash’s cock, her nerves were on fire as her orgasm exploded inside of her. It seemed to run up and down her entire body, leaving her quivering.

She stumbled for a second and the heel on her shoe snapped.

Cash was leaning over her, breathing hard. She could feel his breath on her back and what felt like a drop of drool running down onto her. They stayed like that for several seconds catching their breath as the world caught up to them.

Jennifer moaned as Cash eventually withdrew his cock from her. She stayed hunched over the pallets as she felt his cum running down her leg.

Cash stood back and looked proudly at his handywork. He had loved every moment of this. Getting kicked out of the shelter the week before and having to come back to this alley had been the best thing that ever happened to him. He pulled up his sweat pants and finally remembered the broad’s husband standing there.

He looked shell shocked, unable to move to speak. Cash grinned as he passed by him. He smacked the taller man on the back and laughed, “Thanks, that was much better than the change you didn’t give me earlier.”

Cash disappered down the dark alleyway as Michael began to collect his wife.