On the Way Home

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This is my first piece on Literotica, so I decided to make it short. The first half is based on a true story from a friend of mine.

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There were some things that Lisa knew were a bad idea, but felt she had to do them anyways. On principle almost. She lived in one of the lower quality areas of Hollywood, not a high-crime area by any means, or at least by LA standards, but she knew that a five-foot-two, twenty-something girl, walking towards her neighborhood at night, was going to be hassled by men. And she walked home from work every night, because she knew she could handle herself.

Though I guess that depends on what standard you were judging her by. She had gotten in to trouble on the way home before. Besides the hollers she got from men outside the club she’d walk by on her way home, and the two or three times a week college guys tried to pick her up off the street, she did have a few serious encounters. A man pretending to be a cop tried once to get her into his car. He took a knee in the balls, and eventually a five-year prison sentence, but she had almost done as he asked.

She also had a hard time paying her rent. Except for a few months where she was stripping for a webcam, and a few months where she was giving massages and talking dirty to some rich clients of an escort service (she refused to have sex in either of these cases), she was usually working the counter at one of the top-end clothing shops in town. A job she rarely thought paid her enough. At a previous apartment the landlord had been a good looking Brazilian guy, in his forties, but still a pleasant way to get out of paying the rent. Her current landlord was far less pleasant. And she was late on the rent again.

Her landlord had given her three days, and she was still a week away from her next check. Her roommate had moved out two months before, and hadn’t found her another one, and Los Angeles rents were just so goddamn expensive. She had walked home angrily, thinking of which of her friends she could borrow the money from. She had never borrowed money before, and her friends were all just as bad off as she was, and she couldn’t call her parents. The guys at the club all shouted at her, just like they did every day, but today she flipped them off, she wasn’t in the mood for it.

As she walked on though, thinking about how she was going to get 300 dollars, the idea of letting someone pick her up stopped being so unthinkable. When she worked for the escort service, there were a number of her clients that she had thought of sleeping with. She was just concerned for safety’s reason. Sometimes when college boys would shout at her, they all weren’t so bad looking either.

When she was near home a car carrying three guys drove up next to her. It was a good sized sedan, with all the windows down. The guys were attractive, maybe not her type (she liked rockstars), but they all had short brown hair (one had a shaved head), not too many and not too few muscles, and they seemed alright. The guy in the passenger’s seat shouted at her.

“Hey!”

She turned to scowl at them, but then changed her mind. She looked them over for a moment. When she decided, her face lit up with a practiced smile, that all the men she had been paid to charm fell for.

“Hey,” the guy said, ” you working?”

“What do you mean?”

He looked unsure of himself, but played it off casually. “Sorry, we just… it’s my friend’s birthday today, and his girlfriend just left him. We wanted to find him a birthday blowjob.”

“No luck with the girls at the club huh?”

He laughed, “no.”

“Well I don’t know what to tell you, coffeedonutfest.com I’m not a prostitute.”

“Well would you consider doing it for free then?”

She smiled at his cheekiness. And walked over to the car.

“How much will you pay then?” she asked.

“Fifty bucks?”

“I’ve never had sex for money before, and I’m not changing my policy for fifty bucks.”

“This isn’t sex, this is a blowjob,” he said, noticing that his cheekiness was working.

“One hundred, take it or leave it.” She figured she could drum up another two somehow, and a blowjob was just a blowjob.

“Alright, get in.”

“I should warn you, if you guys try anything funny, I’ve castrated a man before.”

“Duly noted!”

She got into the car next to the birthday boy in the backseat. He was obviously unsure of this, but he wasn’t going to turn down a blowjob, especially if his friend was paying. She put her hand on his pants over his cock.

“Where’s the money?”

The guy in the passenger’s seat pulled out two-fifties and handed it to her. She put them in her purse and then put the purse between her and the door.

“You can drive slowly around the area, anything else and I’m getting out.”

The driver started moving, it was late, and there weren’t many people on the street, but they didn’t really want to be noticed. He drove out onto the main streets figuring that as long as he kept it under 40 she wouldn’t mind. He also rolled up the windows, because even though they weren’t tinted it would be harder for people to see through them.

As soon as the car started moving Lisa had the boys cock out. It wasn’t a bad looking dick, 6 inches, uncut, as wide as three of her fingers (though she had small hands). She looked at it, and tried to just think to herself how much she liked penises, and avoid the nagging guilt of prostituting herself. She stroked it a few times, trying to get acquainted with this thing on short notice. Then she looked up and noticed the guy in passenger’s seat staring at her, and the driver looking in his mirror. She giggled (she was turning on the charm).

“I almost forgot what I was here to do.”

She got on her knees, half laid down, an odd position but the best she could do in a sedan. She grabbed back a hold of his dick, looking at it, and licking it a few times, before she plunged in and sucked in to the back of her throat.

He gasped, and grabbed hold of her hair. Then moved his hands down to her shoulders. She held him in her mouth for a while, playing with him with her tongue, before she started to bob up and down. He was hard as a rock, and she wondered how long it would take before he came. She considered herself fairly good at blowjobs, and thought with a bit of luck she could earn 100$ in less than 10 minutes.

He wasn’t going to cum though, he almost never came during blowjobs. He didn’t know why, but he couldn’t cum unless he was in the right position, which rarely happened during blowjobs unless the girl lifted his ass off the bed, or he fucked her face. The car was preventing him getting in the former position, and Lisa was preventing him from getting in the latter position.

Lisa was trying all her cock sucking tricks, and he loved it. She massaged him with her throat, pulled out and licked the tip, sucked on his balls before diving down and taking his dick in her mouth again. He played with her tits, which hung down in this position, with her low-cut shirt giving him plenty of room to grab. After 15 minutes though she was getting tired, and slightly annoyed. When the guy from the passenger’s seat started feeling her ass, she felt she needed to get control of the situation. She looked up and noticed the two boys up front stroking themselves (she also noticed the driver’s cock must be at least 8 inches, if not 9).

“Hey, I only remember being paid for one guy,” she said to the guy in the passenger’s seat.

He removed his hand, and then she looked up at the boy she was sucking with a “don’t you want to cum” smile.

“Anything I can do to help you along?” She asked.

He was a bit unsure of himself. But he just said it. “This position. It’s hard to cum in this position.”

“Well what position do you need to be in?”

“I need to fuck… need to have sex.”

She started getting up. She wasn’t going to get AIDS for a few hundred bucks.

“I wasn’t paid for that sorry.”

“We can pay you!” The guy in the passenger’s seat almost shouted. “We have the money, do you want an extra 100, 200?”

“It’s not the money, I just don’t know where you guys have been, and don’t want to get any STDs.”

“He’s been with his girlfriend for over two years, he you’re the first girl since then, and we have condoms.”

She was unconvinced.

“Look, how about 400 dollars?”

She sighed. “500”

“How about this, 500 and you give me a blowjob too… I do cum when sitting down, so no need to worry there.” His friend in the driver seat looked at him angry, having thought this was just a birthday thing, not thinking all his friends were going to get laid while he drove around.

She paused, she didn’t really want it to go this far, but she needed the money. And after all she had boyfriends before who weren’t as good looking as these guys.

“Alright how are we going to do this?”

It was a bit complicated, but luckily she was small. The guy in the passenger’s seat was able to put back his chair, so he was laying down, she was able to stand between the chairs so she could bend over him and put his dick in her mouth, and the birthday boy could kneel behind her.

She got in position, giving the birthday boy space to get her pants down. As he pulled them down, he quietly murmured “oh my God” to himself.

“You ok back there?” She said.

“You have the most beautiful ass I’ve ever seen.”

Though she had lost some of the excitement she had from the blowjob while cavorting in the car, the comment made her smile, and made her ready for what she might otherwise have cringed at. He began nudging at her vagina a little with his dick, then he grabbed her ass to steady himself, and slowly pushed the head in. He wanted to savor this, he slowly moved in until he was half way, and then he thrust all the way in. She gasped. She loved the feeling when a cock first penetrated her.

Once he got his rhythm going she stuck the other guy’s dick in her mouth. She had done this before, taken two guys — actually twice before, but both times with the same ex-boyfriend, and the same friend of his. She loved sucking dick, and she loved the attention, it was a huge turn on, even with two complete strangers. She even thought she might…

The guy came first. After the blowjob he received it only took him three minutes to go over the edge, she reached a hand down to finger herself, but only a minute later she felt the cock in her mouth bulge up and begin to shoot stream after stream of cum. She fell back on the seat next to the birthday boy, trying her best to get herself off.

But then she noticed the car had stopped. They were in a mostly abandoned parking garage. And the driver was looking back at her.

“I need to cum” he said. “I’ve got 500 dollars,” he already had a condom on as he fished out the money for her.

“I don’t know.” She said. It wasn’t so much the money as it was the attitude that bothered her. Before the guy in the passenger’s seat at least sweet talked her. Now the passenger’s seat guy was just moving up his chair and getting his pants back on.

The guy in the driver’s seat got out, when the birthday boy shouted, “hey, be cool Mark.”

Lisa went for her pepper spray, but by the time she got to her purse he was opening up her door, and managed to grab her by her kicking legs. He pulled her to the door, spread her legs, and started… licking her?

His sudden concern for her orgasm threw her off, and she wasn’t sure whether she should continue struggling or enjoy it. She didn’t know whether her brain was just thinking poorly, but she decided anyone who could give her such a blowjob couldn’t be taking her against her will. She decided that, she decided that she just wanted to cum. Lifting her ass off the seat a bit, she exploded, grabbing his hair during the orgasm and grinding him as hard as she could against her cunt. “Bastard,” she thought as her orgasm wore off, though she thought it with a grin.

The man did want to cum though, and as soon as she was done he flipped her over on her knees and entered her from behind. She couldn’t help but shout as his big dick roughly entered her, but she quickly got into it, gasping with each thrust.

She was almost hitting her head against the birthday boy, who looked at her with an almost look of curiosity, reaching down to grab her bouncing breasts. He then scooted over, so his newly erect prick was right in front of her face. She didn’t think about it, she just sucked him in. Letting the thrusts of the man behind her guide her movement.

The driver lasted 20 minutes before she felt him tense up and his dick shoot off in the condom. When he pulled out she didn’t move, she slowly let her wits come back, but then the guy from the passenger’s seat had taken the driver’s place and started fucking her. The birthday boy moved into a position where he could move his hips a bit better while she blew him, fucking her face while his friend fucked her from behind. The guy from the passengers seat went almost ten minutes before blowing off. When he pulled out she collapsed on to the seat with her eyes closed, before long she felt the warm splash of cum from the birthday boy falling on her face.

She took a moment to collect herself, get all her clothes back on, wipe most of the cum off her face. Then she got out of the car.

“Here,” the passengers side guy said to her, “its all we have.” He handed her another 1000 dollars. “1600 dollars… and you had fun right?”

“We can drive you home,” the guy from the driver’s seat said, obviously feeling a little guilty.

“That’s ok,” she said. She took the money, put it in her purse, and started to out of the garage. The guys started the car, saying a timid bye as they drove slowly by her.

When she got outside she realized she was only a block from her house. She walked home, feeling more than a little bad about herself.

When she got back to her room, she took a shower, cleaned up her face. She felt like she wanted to call someone and tell them what happened. But who could she tell?

She lay in bed, tense and thinking. She wasn’t really thinking about anything though, she just couldn’t believe she did that.

She sighed, and took the vibrator out of her bedside table. She turned it on and put it inside her. As the orgasm washed over her, she slowly felt her muscles relax.

The next day she felt better about everything. And when she walked home from work she just ignored the shouts of the guys from the cars driving by.