The Misadventures of Josh

Foreword

If you've ever read manga or comics where the main character is too dense to understand women and the situation and is forever passing up pussy, then this story might amuse you as the MC is too dense to understand women and the situation and ends up with all the pussy.

Happy Reading!

***

Once Upon a Bottle of Booze

Josh was not in a good place. He had been kicked out of his apartment for failure to pay for 6 months. He couldn't pay rent because he had been fired from his job. He had been fired from his job because he got into a car accident in the company car, which totally wasn't his fault, but the dumb bitch had waved her tits in front of the cop and then suddenly it was handcuffs and jail for him. There may have been a few more steps in there, but that's basically how he got here, living in an alleyway in downtown San Fransisco, with nothing to his name but a half-empty bottle of rum and a gun with no bullets or trigger. He wasn't really sure why he kept it, but at this point he didn't really have anything else, so it seemed a waste to toss it.

Josh fumed about how he got here, taking another big swig of cheap rum. He was already wobbly and drunk, but he didn't care. He really wished that he could find that bitch again and, and, well shit, what would he do? Maybe make her drink this bottle and, and, what was he saying?

He got up and wandered over to the dumpster, aka the pisser. He stumbled a bit around it so that no one could see him from the street and proceeded to relieve himself. He heard someone on the other side of the dumpster now, but he was honestly too drunk to really make out what they were saying. He swayed a bit, shook himself off, and went back to his spot. Wait, was this his spot? Who the fuck was this? He stumbled past it and turned around.

"Oh my god, please don't hurt me." The blurry person squealed at him as it moved away from him. That's what he thought it said. He rubbed his face a bit.

"No no, please, don't shoot me." She was crying now. What, shoot who?

"I, I have money. I can give you my money."

"I like money." Josh slurred, trying to point at the person. "You gonna give me money?"

Another cry came out of her, "Yes, yes, I have lots of money. It's all yours."

"Woah, thanks. That's mighty fine of you." He took a step forward and then stopped. Wait, it's not right to just take things. He should give them something. He looked at the bottle in his hand, and then the gun in his hand. Well, the gun is busted, so that wouldn't be nice. "Here, have some of this." He lurched forward, practically slapping her in the head with the bottle.

She cried out again and stumbled back, falling on her butt. He could see her a bit better now that he was closer. She was pretty. Well, he thought she was pretty. Honestly, he couldn't really tell, but she had brown hair, great set of tits and a short skirt, so that seemed pretty hot to him.

"Here, have some. It'll be good for you." He pushed the bottle at her again. Or was that the other hand.

"Okay, okay, please. I'll drink it, okay? Please don't hurt me." She had backed up behind the dumpster now, back against the wall as he stood almost over her. She tentatively reached out for the bottle.

Oh right, he should pour some for her. No cup though. Probably fine.

He brought the bottle up to her lips, which was easy as she was on her butt. He couldn't aim very well though, so he ended up pouring it all over her shirt and then into her mouth.

"There you go. Drink that." He could hear her chugging, coughing and sputtering. "Woah girl don't drink too much. You'll get sick."

She was gasping on the floor. "Is that, enough?" She gasped, feeling her stomach roiling with all the booze in her gut.

"Enough? Enough for what?" He was confused again, why were they here?

"Please, I'll do whatever you want. Just don't hurt me. Please." She was softly begging now, crying little sobs.

"There there, no need to cry." He pet her with his other hand, didn't want to spill anything more on her.

There was a choking sob, but she didn't move. "What, what do you want me to do?" fat tears were rolling down her eyes.

That was a good question, what did he want? He was pretty sure he had a long list of things, but for the life of him he couldn't recall anything. He just shrugged, "Guess I don't need anything really." He suddenly remembered, "Oh man, I'd kill for a phone." He had a lot of people he needed to call. The lawyer, the cop, that bitch with the nice tits. He got lost in thought when the girl handed her phone to him.

"Oh, that's a good one" He went to grab it and saw his hands were full. He looked between them and then put down the alcohol. Leaving a gun unattended could be dangerous. "Is this unlocked?" The girl frantically nodded her head. He swiped around and the camera came up. "Oh shit, this is nice. Thanks."

Josh considered a bit; he didn't really need anything now. "Time to go." He pointed at her while checking the phone. The quality was really good, there was a movie of a sobbing woman on it. Really high def, but he wasn't following the plot.

She sobbed hysterically, "Please, I can, I can suck your dick. Please don't kill me."

"Oh, I haven't had my dick sucked in a long time. That sounds pretty good."

The girl in the movie crawled up to the cameraman. She kept crying, which was a weird choice for the director, but he wasn't an art critic. The girl pulled out a limp dick. Really weird direction of this movie.

The girl looked up at him, tears streaming down her cheeks as she slowly licked the cock, shuddering at the foul taste. She continued, seeing the gun waving around more, sucking it harder, getting it hard.

The dick was finally coming to life in the movie. About fucking time! It was a good-sized dick he thought. Looked kind of familiar; maybe some famous porn actor like that guy, that one, the one with the dick. The gun waved in front of the camera and the girl pressed her mouth down, taking most of it down her throat in one go. Damn, lookit her go. That guy with the gun though was really ruining the mood.

The gun kept waving around her, and she kept sobbing and trying to cram more of the fat cock down her throat. She didn't know why he was doing this, but she knew she needed to get him off so that she could run. She extended her tongue, licking his vinegary shaft as she continued bobbing on it. Suddenly, he lurched forward, and she choked on his cock. She backed up but hit the dumpster. The cock came again, pressing hard into her throat until it slid the rest of the way down. She sobbed as the cock forced her throat open, she couldn't breathe, her nose was rammed into his body. He was choking her.

Holy shit, this movie went hard! The dude just shoved his fat cock down this little slut's throat. Just watching it was getting him off. It was like he could feel her throat gripping him. He stumbled back a bit and then got his balance back.

The cock came out of her throat, and she took a huge gulp of air, coughing and crying as her abused throat ached. She knew that she couldn't stop though because he was still there filming her. She sat up again as he moved forward, jamming his cock down her throat again. She tried to swallow, to cry out, but the pain remained. She could feel his cock in her throat with her hands, it was bulging it out, but she couldn't move.

Oh fuck, this was so hot. He felt like he was gonna pop just watching this shit. The little slut's eyes were rolling into her head as she choked on the cock. He couldn't take it and unloaded blast after blast. It timed up perfectly with the movie as the girl swallowed hard, gagging over and over as she tried to swallow the load.

He finally stumbled back, the girl doubling over and vomiting cum and booze onto the ground. That was a weird way to end the video he thought. He put the phone in his pocket, he'd watch it again later. He looked over and saw the girl from earlier lying on the ground crying.

"Aw shush sweety, it'll be alright. What's your name?" She stared up at him, eyes red from crying, throat raw from being violated, but she saw the gun wave again.

"Allison." The gun kept waving, "Allison Escora."

"That's a pretty name Allison. You should get home though. It's not safe in these parts."

A moment of hope flared in her eyes. "I, I can go? You'll let me go?"

"It's a free country, isn't it? Oh, didn't you drink some of the booze? You should pay for that."

"Yes, yes, here, it's all the money I have. Can I go now?" She was smiling at him through her tears. She had done it; she had convinced him to let her live.

"Yeah. You be a good girl now."

She nodded and slowly stood up. Josh stumbled back a bit and saw the booze. When he went to pick it up, she ran, as fast as she could. She never looked back.

"What a nice young lady." He took a swig and pulled out the phone. He swiped a couple of times and that movie started playing again. "Fuck, that's hot."

***

Home, Sweet Home

Josh woke up the next day with a massive hangover, promising himself once again to stop drinking. He sat up against the dumpster, covering his eyes as the sun was coming up over the rooftops. He looked around, found his empty bottle of rum, cursed himself for having tipped it over, and his busted ass gun. He then noticed something else in his pocket. The most interesting thing he thought was the $500 that he had in wadded bills. The other really interesting thing was a phone he didn't recognize.

Well, first things first, where the fuck can a homeless person go to get a shower, a meal, and some clothes? That was a real question, he actually had no fucking clue. He pulled out the phone again and checked it. It fully unlocked, sweet.

The background was of a cute busty brunette, maybe 18 he guessed, with another stacked blonde as they posed doing the peace sign. Both girls were wearing skimpy bikinis and had rocking bodies. But he'd look over that another time. He clicked the map app and looked around the area. He actually didn't even know where he was, but he managed to find some thrift shop right around the corner. That takes care of the clothing. After that maybe get a cheap ass motel for the shower and then grab a burger.

After the shopping spree of $35 got him a new wardrobe, he walked across the street to the motel and dropped $50. He showered, he shaved, he felt like a human again. He also chugged a ton of water because he also felt like shit. Finally, he grabbed himself a big burger and just chowed down.

Back in the room he looked over the phone, trying to figure out where this came from. He found Allison Escora as the owner, and she lived in the area. He did a quick search and saw that she was some small-time influencer. Either way, he should probably return her phone. He clicked the uber app and saw that the home address wasn't too far away, so he called one and rode the 20 minutes to a nice-looking neighborhood. These were actually houses with little yards.

He rang the doorbell and waited for a bit. He didn't hear anyone, but he saw a car by the garage. Maybe she just hadn't heard. He tried again, and this time someone came. The door swung open and a 5'2" gorgeous brunette in skin-tight leggings and sports bra supporting her perky C-cups answered. She had her hair in a ponytail and light makeup on. She may have had some Hispanic in her. Her soft brown eyes looked gorgeous.

"Hi, can I help you?"

"Uh, hi, sorry, you probably don't know me. I found your phone downtown and wanted to return it."

When he said "phone" she froze. A look of dawning recognition came over her. Josh wasn't sure what was going on, but he reached for his pocket.

"No no, please, it's okay. I won't say anything." She pleaded with him, stepping back into the house.

Josh froze, thoroughly confused. "Won't say anything about what?"

"Nothing! Nothing at all." She looked nervously around, worried that he brought friends this time.

"Well, is there a reward or anything? I'm actually kinda down on my luck."

Allison's heart started racing, but she could see the gun in his pocket. He had let her go last time, he wouldn't hurt her this time either, would he?

"Y, Yes, of course." She licked her lips, "Right here?"

"I mean, that would be great if you could."

Allison saw several people walking down the road, and started to tear up, thinking about how he was planning on throat fucking her here in front of everyone.

"No. Please not here." She begged quietly again, "Not in public. Please."

"Oh, uh, sure. I guess we can do it privately."

A nervous smile spread across her face, "Thank you." She nodded her head gratefully. "Would you like to come in?"

"Oh? Uh, sure. If that's what you want." He stepped into her house. It was a nice-looking place. Very neat.

"What would you like?" She watched him carefully, trying to keep him happy and away from the gun.

"Well, I just ate, so I'm all set there. What else you got?"

She swallowed hard, "There's, there's what you had last night."

Josh tried to think what that was. All he recalled was throwing up at some point. "I'm going to pass on that, thanks." She let out a little whimper. "Why don't we sit down? I could use a break."

Allison stifled a cry but nodded. She took his hand and led him to the bedroom.

Her hands were really soft, he marveled as she led him deeper into the house. Very outgoing too. He couldn't recall the last time he'd held a woman's hand. She took him into a pristine bedroom, like one you'd see in a magazine. She led him to the bed and sat down next to him. She was sniffling.

Josh felt bad, she must be really torn up about her phone. "Here, I can give it to you now if you want." He reached into his pocket and she caught his hands again, looking into his eyes and pleading. "No, please no, it's fine. I'll take care of you."

She slowly moved her hands from his and reached into his pants. She ran her hand up his length, which was already engorged. She glanced up at his face, "Is this good?"

This was the greatest form of payment he could have ever hoped for. No wonder she wanted to do this in private. Her soft hand was already wrapped around his cock and stroking him. "That's real good."

She nodded, and pulled out his cock, leaning her head down to lick the tip. She was surprised that it was clean, remembering the horrendous odor and taste from last night. This was almost pleasant. She bobbed on his cock, slowly taking more and more into her mouth, sucking and drooling on it like he had wanted last night.

Josh was in heaven. This 18-year-old goddess was sucking his cock and was a fucking pro at it. He stroked her silky hair, enjoying the feeling on his hands as he lay down on the bed.

Allison felt the hand and knew what he wanted. She pressed down harder, until she could feel him in the back of her throat. There were still 4 inches left to go, so she opened her jaws wide, and pressed until her throat barrier popped open, and it sank all the way down her throat. It didn't hurt as much this time, and she swallowed around him, running her tongue on his balls.

She pulled it out a minute later, beginning to feel light-headed. She took a deep breath, coughing a bit, and darted a glance at him. He seemed happy with her work, so she went back down on him. She slid it into her throat again, more forcefully fucking her own throat for him. She made gagging and retching noises the way he liked it and came up for air when she needed to. He was groaning and thrusting his hips as she went in again, and she kept going until she felt him press her head down and cum down her throat.

She swallowed again and again, marveling at the massive load he was dumping into her. Last night she had been terrified and he had been so rough, but today he was much gentler.

Josh couldn't even think straight. He had just dumped his massive load down this girl's throat, and she just moaned as she took it into her tummy. He loved San Francisco.

Allison pulled her head up slowly, licking off the excess saliva and cum, before swallowing it down. "How was that? Better than last night."

"So much better than last night."

Allison was starting to think that she had satisfied him enough and that he'd leave now. She went to put his pants back on but noticed that he was still hard. If anything, he was harder than before.

She started breathing harder again, certainly, he didn't need more.

He leaned up and saw her staring at his cock. "Oh yeah, don't know why, but it never seems satisfied with the one." He chuckled.

She looked at him horrified. It wasn't good enough.

"Oh, here, let me give you this now."

"No, no, no, please, I can do better."

"What? It's not about that."

Allison stood up and pulled her sports bra off in a panic, her perky tits jutting out at him. She peeled off her leggings, showing him her shaven pussy and tight ass.

"See? I can do better. Please, let me do better." She pleaded with him again. "Any way that you want, please, just don't hurt me."

Josh nodded; she must be a virgin. Weird that she was being so aggressive, but he guessed that societal pressures being what they are, she probably just wanted to get it over with. "Sure, I'll be gentle."

She nodded, tears welling in her eyes. "Can I, can I lie down please? I don't want to watch it. Please?"

Ah, squeamish girl, afraid of seeing potential blood. "Sure, make yourself comfortable."

She hesitantly climbed onto the bed, grabbed a pillow, and placed it under her hips as she rested her upper body on the bed, face down. Tears were flowing down her cheeks, silent sobs caught in her throat as she presented herself to him.

The girl was obviously nervous, she was practically shaking in fear. Josh moved behind her, running his hands along her back to make her feel better. He slowly spread her glorious cheeks to see her tight rosebud and silky lips. They weren't wet yet, and he certainly didn't want to hurt the girl, so he leaned down and started lapping at them.

She gave a startled gasp as he continued licking her, running his tongue down to her clit and up again. She shook as he slowly aroused her body, even though she didn't want it to. She was slowly getting wet from his gentle licking. He would flick his tongue over her clit, making her shudder and squeeze her eyes as tears ran down them. She was starting to gasp, her hips responding to him as he suddenly pressed his finger into her.

Allison bit into the sheets as she felt his finger intrude into her. He was surprisingly gentle, feeding it into her with little pulses, which made her pant. She shook her head in denial as his second knuckle sank into her, curling and hitting her g-spot. He continued to flick at her clit and curl his finger into her, she could feel an orgasm building, but she ground her teeth hard. She didn't want to cum, not to him. She begged herself not to cum, willing herself to stop, wishing he would stop.

She held out for another minute, until she suddenly screamed into her mattress, her pussy contracting hard around his finger, her hips twitching as the delayed orgasm wracked her body. Long gasping sobs came from her as he continued to finger her through her titanic orgasm.

Allison finally slumped on the bed as it thankfully ended, no strength in her legs to support herself anymore. She could barely think straight following the orgasm, which was why she hadn't noticed him getting up and placing his bare cock at her hole. She only noticed as his swollen head opened her up and popped in with minimal resistance that he was fucking her raw. Panic set in as she tried to move away from him, but she was already against the bed, and he had her hips pinned as he fed more of his cock into her wet tunnel. She gasped, tears still on her cheeks as he smoothly fit his entire cock into her. She lay with her mouth agape in shocked silence as he stretched her, grinding his cock into the deepest part of her.