Charlie hated driving for a rideshare and would have quit a long time ago if it wasn't for one special perk: drunk female passengers.
This story is a work of fiction, and all characters depicted are 18 years of age or older.
Rapeshare - The Beginning
“Have a safe flight,” Charlie said to the man who exited Charlie’s car and walked through the terminal doors at the airport without acknowledging Charlie’s existence.
“You cheap fucking asshole,” Charlie muttered to himself after seeing that the guy didn’t leave a tip.
Charlie was 52 years old and had been driving part-time as a rideshare driver for the past two years to supplement his income.
He hated it, though, and would have stopped a few months into it if it wasn’t for a special, unexpected perk that came with it: attractive drunk women.
The busiest times were when the bars and clubs closed for the night, and at least once or maybe twice a week, he’d have a totally shitfaced woman by herself in his car.
Whenever that happened, he lied, saying he had to pick up another passenger or that the back seat was wet, and then asked her to sit in the front seat.
Then, depending on how drunk she looked, he’d let his hand wander over her legs and see what kind of reaction he got from her before going further.
If she were unresponsive to his touch, he’d start feeling her tits, and if she were wearing a dress or skirt, he’d try to get her panties off and his fingers in her pussy.
Usually, he’d take them to their destination and end the fare before sexually molesting them somehow.
That way, he didn’t have to keep one hand on the wheel and his eyes on the road.
But if a woman were drunk to the point of passing out, he’d park a little bit away from the destination address before raping them.
That way, if anyone was expecting his passenger, he wouldn’t be seen and could have some fun before letting them out of his car.
Often with some coaxing and maneuvering, Charlie could get the girl’s top and bra off and then get himself a blowjob while he was squeezing her naked tits.
A few times, if he had parked in an isolated and dark enough place, he’d get a woman into the back seat for a normal fuck, but that was a lot of work and had a high risk of getting caught by someone walking by.
Last night, he was telling his close friend, Kevin, about his latest blowjob from a blonde wearing a cocktail dress that was so short that he had full access to her pussy from the moment he tricked her into sitting next to him.
Suddenly, his buddy stopped him from finishing his story and suggested that they work together in the future.
Kevin said that when Charlie had a potential target, he should text him the destination address, and he would meet him there with his van and put her in the back.
Then, they could both either fuck her in the van right then and there or drive her to someplace else more secluded.
Since there were two of them, they also came up with a few ways to use the rideshare app itself to give Charlie a few alibis to prove he was working and not raping anyone.
Charlie wholeheartedly agreed to his friend’s devious plan.
A few nights later, Charlie thought he had a reasonable prospect named Amy.
She was in her mid-twenties with long curly black hair and was wearing a strapless cocktail dress that showed off her big tits and lots of tattoos on her bare arms.
Amy was clearly shitfaced and kept asking Charlie the same questions repeatedly, but she never stopped talking and never once fell asleep.
Charlie put his hand on her thigh a few times, but she always pushed it away.
Amy was drunk, but just not drunk enough.
The very next night, Charlie picked up a drunk and good-looking MILF, named Karen.
She kept asking him if he thought she was pretty, and it didn’t take Charlie long to talk her into taking off her shirt and bra for him.
By the time Kevin met them at her destination, she was in the middle of giving Charlie a blowjob in the back seat while he had her dress up to her waist and was fingering her pussy.
Unfortunately, when Kevin opened the door and started to get into the car with them, Karen sobered up fast, told them both “to fuck off,” and left Charlie with a full erection covered in her spit and hanging out of his pants.
Two weeks later, though, they hit the jackpot.
His fare was two women who had just left a bar. From their manner of walking as they approached him, Carlie could tell they were both drunk out of their minds.
From what he heard through an open car window, a mutual guy friend of theirs was trying to get one of the girls (a pretty Asian) to go back to his place.
Charlie heard the Asian girl agree, but wanted to ensure that her friend made it safely to the cab.
Once her friend was in the back seat, the couple waved goodbye to her and walked away.
The woman in the backseat was a drunken mess and was unconscious just a few moments after sitting down.
Charlie turned around, turned the overhead light on, and got a good look at her.
She was gorgeous and looked like she was barely old enough to get into the bar where she was drinking.
The girl didn’t respond to any of Charlie’s questions, and when he reached back and started rubbing her legs, she didn’t react at all.
It was hot that night, maybe 90 degrees and humid, so she wasn’t wearing much.
She wore a blue strapless dress that stretched and hugged every curve of her 5’5”, 120-pound body.
Her long and straight blonde hair reached down to just above her D-sized breasts.
The dress was short enough to show off her long legs, and Charlie could see that she had already kicked off her heels.
Charlie had even lucked out with where she lived.
Her home was only 20 minutes away.
Kevin said that he could be there in 25.
Twenty-three minutes later, she was in the back of Kevin’s van, which was parked down the street from her house.
Kevin had removed the back row of seats and had a few blankets spread out to make it comfortable for the two men.
Charlie made sure to turn off both his rideshare app and his phone before Kevin got there.
As far as the rideshare company was concerned, the ride was over, and Charlie was off the clock.
The two horny men didn’t even know her name, so Kevin checked the sketchy-looking license in her purse and saw that her name was Emily and that she was supposedly 21 years old, but neither man thought she was even in her 20s yet. He also pocketed the two twenties he found in there.
Emily’s dress was so thin and stretchy that it was easy to take off, and soon she was naked and having both her breasts squeezed and sucked on by Charlie.
Kevin started rubbing her pussy and jamming first one and then two and then three fingers into her while he was kissing and sucking on one of her legs that he brought up to his face.
Kevin took his pants and underwear off and, after getting Charlie’s permission to go first, positioned himself between her spread legs and got a good look at her round breasts that were jiggling like mounds of jello.
Then, he saw the thin landing strip that she had for pussy hair.
Kevin’s heart was pounding out of his chest!
He had loved listening to Charlie tell him about the drunken women he had molested in his car, but this was all new to Kevin.
Sure, he talked confidently to his friend, but he couldn’t believe that he was really going to do this.
He shoved half his dick inside her and stopped, suddenly having second thoughts.
But her warm pussy felt so good that he couldn’t resist and just slowly pushed the rest of the way in.
Within seconds, he was pounding his cock in and out of Emily’s defenseless pussy.
Her head rolled back and forth, and she started mumbling something incoherently.
Her hands tried to push Kevin off her, but Emily was barely conscious and too weak to stop him.
Charlie said that it sounded like she liked what Kevin was doing to her, which just made Kevin fuck her faster and harder.
It didn’t take long before he groaned loudly as his cum shot inside her pussy.
After Kevin rolled off her, Charlie rolled Emily over, and the men propped her up on her hands and knees.
“Shit! Look at that cute little ass! I wish I thought to fuck her her doggie style!” exclaimed Kevin.
“Yeah, it’s the best position to fuck these sluts in the back of a car when you can’t spread their legs out wide. Now, it’s the only way I like to fuck ‘em,” said Charlie.
While his hands were firmly holding onto Emily’s hips, the 52-year-old continued to plow into the teen from behind and moved her forward inch by inch until her head was stuffed into the gap between the two middle row seats.
“Dude, you are really giving it to her!” Kevin encouraged his friend.
Emily lifted her head off the empty Doritos bag on the floor of the van and tried looking behind her at the man who was fucking her.
At that, Charlie nodded to his friend and said with a smile, “Watch this,” before slapping Emily across the face so hard that she collapsed and passed out on the floor.
Charlie grabbed her hips again and kept her face down and ass up while he continued to fuck her.
With a loud groan, Charlie dumped his load deep into the pussy of his unlucky ride-share passenger.
Following the plan, Charlie got dressed and drove home in his car, leaving Kevin to bring her closer to her house or dump her out somewhere safer where he wouldn’t be seen.
Kevin, though, was still riding high on the sexual rush he was experiencing.
Raping a teenage girl like they had and under these circumstances was exhilarating, and his dick was still hard as a rock.
After making sure that Charlie had safely driven away, Kevin pulled both of Emily’s legs up against his chest so she was bent in half and then entered her pussy a second time.
With Charlie gone, Kevin lost any inhibitions and let his darkest fantasies control him.
Within seconds, he fucked the barely conscious girl as violently as he could.
Throwing his body down on top of hers with each hard thrust.
Emily was moaning and gasping in pain constantly at this point as each thrust down pushed all the air out of her lungs.
Kevin wasn’t sure if she was moaning in pleasure or pain, and he didn’t care so long as it wasn’t too loud.
After several minutes, Kevin’s body went rigid as he orgasmed and flooded her pussy with his second orgasm.
At that point, Emily started to wake up a little and aggressively tried pushing him off her, but Kevin stayed on top of her with his half-hard dick still in her pussy.
Kevin was 57 years old and married to a fat, frigid bitch of a woman.
It had literally been four years since they had last had sex, and now here he was with a beautiful blonde teen who was naked and all alone in his van.
His cock had started to soften, but was getting hard again just thinking about it.
Meanwhile, Emily was now awake but still so drunk that she didn’t know where she was or what was going on. She sensed she was in trouble, so she started to fight back and make noise.
Thinking quickly, Kevin slid her off the blankets and slammed the back of her head against the metal floor of the van a few times until she went still.
Then he started mauling her tits, and then gripped them both hard like he was going to rip them off her chest as he used them to lift her up and move her back to the middle of the van.
Keeping his fingers plunged into her big tits, he sat on her flat stomach, put his cock between each crushed mound of tit flesh and then aggressively gave himself the best tit job of his life.
After seeing her beautiful, full lips open wide from the pain he was inflicting on her breasts, he slid up her body and forced his whole cock into Emily’s mouth.
Then he pistoned his cock up and down, hitting the back of her throat each time until Emily woke up again, choking and retching for air.
Kevin stopped, rolled her over on her stomach and lay on top of her with his cock-head pressed into her little asshole.
He was on fire!
This might have been a once-in-a-lifetime chance to fuck a beautiful blonde teen in the ass, and he wasn’t going to miss it.
He reached into a bag of supplies for tonight, which hung on the wall of the van, and pulled out a jar of petroleum jelly.
Wiping some on his cock and whatever that was left on his fingers all around and in her asshole, Kevin held his hard cock in his hand and forced it slowly into Emily’s ass.
The heat!
The tightness!
He had never ass fucked a woman before.
It was amazing.
He fucked her ass slowly and enjoyed every minute of it.
Emily, meanwhile, was trying to get up on her knees and away from whatever was causing her such intense pain in her bowels.
Each time she rose to a certain point, Kevin just smashed his arm down on her back, causing her to go back face down on the hard floor of the van.
After a long while, he grabbed her hips, pulled her up to her knees and then started ass fucking her faster and faster.
Emily’s hair started whipping around as her body started rocking back and forth.
Then, with a loud moan, Kevin held her ass tight against his groin as his balls released whatever was left inside them inside her ass.
But with all the rocking back and forth motion and then the sudden stopping was too much for poor Emily’s alcohol filled stomach, and she vomited all over the blankets and onto some of the van’s floor.
When Kevin was done cumming he shoved her forward again and pushed her face down on her own puke.
Rather than being upset at the mess Emily had made in his van, Kevin smiled, thinking that this was something that he could use.
After getting her and himself dressed, he pushed her face down into her vomit and rolled her all around in it until it was all over her dress, face and hair.
Then, after looking out the van’s windows and seeing no one around, he opened the back doors, laid her down on the sidewalk about a hundred yards from her house, and drove away.
Emily woke up a few hours later, stumbled into her house, and went to bed. When she woke the following day, she remembered being forced to have sex with someone, but was so mortified from being covered in her own vomit that she never told a soul what little she remembered from that night.
Meanwhile, Charlie and Kevin looked forward to summer coming to an end and the college girls returning to town.