Accidental Gigolos - Cover

Accidental Gigolos

Copyright© 2024 by Lubrican

Chapter 2

Romantic Sex Story: Chapter 2 - Bobby happened to be in the right place at the right time and lost his virginity to a woman twice his age. He was a quick learner and soon he was ringing her bell regularly. Then one of her friends needed the same thing. And another friend after that, until Bobby was satisfying the needs of five women. That's a lot for a seventeen-year-old kid to handle. But maybe his best friend could help him out. And that was just the beginning.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   mt/ft   mt/Fa   Consensual   Heterosexual   Fiction   Cheating   Cuckold   Incest   Brother   Sister   Interracial   Black Male   Black Female   White Male   White Female   First   Lactation   Masturbation   Oral Sex   Petting   Pregnancy   Safe Sex   Size  

“Dude!” said Bobby as he bumped shoulders with his best friend. “We haven’t been hanging out much.”

“It’s not because I’m too busy,” said Russell Jackson. “I’ve been hanging around home all summer, with nothing to do.”

That wasn’t entirely true and they both knew it. They’d gone swimming a dozen times over the summer, and gone together to climb the local “mountain” where, history said, a Civil War battle had been fought. That was one of the few times the difference in their races had been discussed. They imagined men, fighting each other, trying to kill each other, just so some of those men could own other human beings.

Russell had adopted his father’s outlook on race and racism in America. More than once Russell had heard his father addressing another black man and say, “Look, if you could go in a time machine and bring any slave from 1850 here, what he’d see would blow his mind. Yes, there are problems to solve, but don’t say the black man is oppressed. Some black men may be oppressed, but most of us oppress ourselves by our attitudes.”

Then the conversation (argument) would usually go on. Russell had never cared about all that until his father moved them to a town where there were only twelve black people in the whole population, not counting his family of four. All the others were grownups, which meant Russell and his sixteen-year-old sister, Teri, were the only students of color at Pine Bluffs High. Teri had no problem, or at least said she didn’t. She was popular and was welcomed on the cheer squad, since she already knew five times as much about acrobatics as any of the other girls on the squad. She was popular with the boys, too, but everyone in their family knew that was because of the novelty of being with a black girl, and not because of any real interest in getting to know her. She didn’t care. She got taken on dates and had a good time. Their parents didn’t worry about her virtue. Russell got the idea that his parents were actually relieved at getting away from the black culture of the big city, instead of missing it.

Their dad had expected pushback from the white officers on the police force when the town fathers hired him to be the Chief, instead of promoting one of those who had already served Pine Bluffs. He had used the unheard of approach of arranging for the sheriff to patrol Pine Bluffs for a week while the police force went camping. It was a training/bonding kind of thing where his men got to know him under circumstances where there were no civilians around to hinder. Whisky flowed at night around the camp fire and during the days Beaufort Jackson taught them policies and techniques nobody else had even thought to offer to them in the past. When the week was over there was grudging respect for the big black man and things were calm. Pine Bluffs was a sleepy little town and most of the excitement they had was caused by drunks or outsiders who came to steal copper or whatever else of value they could burgle. Two residents of Oberlin, twenty miles down the road, had been caught in the act. A state highway went through Pine Bluffs, which meant there was a lot of traffic through town and, occasionally, the force might be called on to assist some other office or agency.

So things were okay with the Jackson clan, for the most part, and Russell was looking forward to his last year of high school, so he could go to college or join the military, one of the two. And Bobby had been a good friend. Life is always a little better if you have a good friend, or two.

What Russell Jackson didn’t know, yet, was that his best friend was going to make his life a lot better, depending on one’s perspective. It would be a lot more complicated, without a doubt, and Russell would benefit from it in ways he would never have contemplated. But it also had the possibility for ruin, and not just the ruin of one young black man in rural America.


Bobby’s life had been so unusual at that point that it is perhaps no surprise that what he chose to do next was unusual, too. He’d spent hours and hours with Russell and knew how Russell felt about almost anything, including women. While his sister went on a plethora of dates, Russell did not. Whenever he asked a girl out she either already had plans or there was some other reason to say no. This was not because no girls were interested in Russell Jackson. It was because their parents weren’t interested in their daughter being out, unsupervised, with an African-American boy.

Russell knew this. He’d even been told about it by a few girls who felt sorry for him. Bobby knew that Russell was a virgin and hadn’t been involved with a girl here on any level, although he did have a little experience before their move to Pine Bluffs. Here he’d had sex with his hand, like just about any other teenage boy, but that was all. Bobby was pretty sure Russell would jump at the chance to have sex if he thought he could get away with it, and Bobby knew some women who were more interested in being sexually satisfied than the color of the man satisfying them. At least he thought so. If at least two of them accepted the idea of bringing Russell into the program, that would ease Bobby’s ‘burden’ a lot.

He approached Julie about it first. He chose her because she was the hungriest of the bunch. She’d been trying to make up for 25 years of nothing and was extremely appreciative of the only man she knew about who genuinely thought she was pretty. Bobby thought Russell, as an outsider of sorts, might be able to understand her situation and empathize with it.

He did not discuss this with his friend, which could have worked out very badly. That, too was a product of how Bobby assumed that his friend would have the same interest in all the women as Bobby had developed. It would have been a little arrogant except Bobby actually believed he and Russell had the same tastes.

He was right about Julie. By now he and she had the kind of relationship most men and women never have. That was friendship of the deep and abiding kind, where people who know them assume there’s some hanky panky going on, even if there isn’t. It’s very difficult to have a good friend of the opposite gender if either or both are married to someone else. Bobby and Julie could do it because neither of them was married and neither wanted to be married.

The point is that one afternoon, as they lay catching their breath after having made love, and Bobby asked, “Would you ever think about doing this with somebody besides me?” Her answer was, “Of course I’d be interested. But it will never happen.”

“What if it could happen?” he probed.

“Just tell me what’s on your mind, Bobby,” she said.

“I have a friend, a close friend, and I know he’d love to be where I am right now. He’s never had sex and he’s like you. He doesn’t think he ever will.”

“So he’s fat and ugly,” she said.

“He is neither,” said Bobby. “There are ... other issues.”

“I assume he’s your age,” she said.

“Yes. He’s my best friend.”

She blinked.

“But your best friend is...” She didn’t finish.

“Russell Jackson,” said Bobby.

“As in the son of the Chief of Police?” Julie was an assistant manager at the Taco Bell in town so she got to see practically the entire population of Pine Bluffs over the course of a month.

“Yes,” said Bobby. “You see why his prospects are slim?”

“I do,” she said. “Let me think.”

He let her think and a good three or four minutes went by.

“I am not horrified by the idea,” she finally said. “I’ve seen him around. He’s kind of cute. Not cute like you, but cute.”

“I can set something up,” said Bobby.

“Why are you doing this?” she asked.

“Because the Card Club is about to kill me,” he said.

“It’s not called the Card club anymore,” she said.

“What’s it called?”

“Never mind. We didn’t know we were wearing you out.”

“There are five of you, Julie,” he groaned.

“If I had to take care of five horny men I wouldn’t complain,” she said.

He just looked at her.

“Okay, okay. I’m not opposed. How would this work?”

“I’ll bring him with me to mow your lawn and then have to leave before it’s finished. He’ll have to finish and you can work your magic on him.”

“I have magic?”

“Julie, I know you don’t believe this, but some day – if it hasn’t happened already - some guy is going to look at you and get as stiff as a board. He’s going to pant after you until you let him in and then you’re going to wear him out.”

“You’re right. I don’t believe you.” She frowned. “Next Saturday? It’s getting late in the season and the grass won’t need mowing much longer.”

“If Saturday doesn’t work I’ll call you,” he said.


Bobby couldn’t figure out a way to broach the subject to Russell about becoming a guy who serviced two or three or even five women, sexually. So he called Julie and told her they were just going to wing it. She said, “I can’t imagine anything could go wrong, so what the hell.”

He asked Russell to help him do a yard on Saturday and Russell agreed, having nothing else to do. The yardwork went quickly and when everything was finished he told Russell to come with him to collect.

They were approaching the back porch when Julie came out and stood, waiting.

“I can’t stay, today,” said Bobby, when Julie came out on the porch. “My mom says I have to go to this thing this afternoon and I have to get a haircut first and all that crap.”

“I’m disappointed,” said Julie. Her voice was flat. “I assume this is one of your friends?” she asked, glancing at Russell, who was still trying to figure out what Bobby meant by “stay today.”

“Yes. He’s my best friend,” said Bobby.

“Your bestie?” Julie clarified. “Does that mean I can be myself around him?”

“Absolutely,” said Bobby.

She looked at Russell and said, “Is it true?”

“Is what true?” asked Russell.

“Do Black men have bigger schlongs?”

“That’s kind of racist, don’t you think?” suggested Bobby.

“Is it?” she said, looking at Russell.

“Yeah, it is,” said the black young man whose penis was being discussed, “or at least most people would say so, but don’t feel bad. About a zillion white women wonder about that.”

“So, back to my original question, then. Is it true?”

“Nobody’s ever seen it to give me an opinion,” said Russell, shrugging. He did not feel threatened by the overweight woman who was being so forward with him. Had she been gorgeous he might have had some self-confidence issues, but her “normalness” made what she was doing also seem normal, somehow.

“I could give you an opinion,” said Julie.

Russell looked at Bobby.

“Wow,” said the dark-skinned boy.

“She and I have a kind of special relationship,” said Bobby. “I’ve never talked to you about that.”

“You better not have talked to anybody about that,” said Julie.

“I haven’t,” said Bobby, his voice almost a whine. “Russell wouldn’t know about it if you could control your sex drive.”

“You guys have sex?” asked Russell, wonder in his voice.

“What’s wrong? Do you think fat girls shouldn’t be able to have sex?”

“I wouldn’t call you fat,” said Russell. “Healthy, yes. Robust, maybe. Stocky, perhaps, but not fat. It would be rude to call you fat.”

“Just like it would be rude to ask a black kid whose name you don’t even know if he has a big dick,” said Bobby, with sarcasm in his voice.

“His name is Russell,” said Julie. “He’s your best friend and now he knows about you and me. I’d say we already have a relationship, or at least the beginnings of one.”

Bobby stared at her. Julie had always been crazy in bed. He thought it was because he was the only guy who paid attention to her in that way, but he didn’t know that for a fact. Maybe she was just highly sexed. Some of the other women were pretty highly sexed. All he knew was she usually needed to cum at least six times before she’d let him go. He held up one finger.

“One moment. Let me converse with my associate,” said Bobby.

He pulled Russell twenty feet away and put his friend between him and Julie, so she couldn’t see his face.

“Okay, here’s the deal,” said Bobby. “I fuck her pretty regularly. I’ll tell you how that came to be later. The thing is she has this crazy strong sex drive and I usually stay after I mow her yard and spend a few hours in bed with her.”

“A few hours?” gasped Russell. “As in multiples of sixty minutes?”

“Yes,” said Bobby. “I have to make her cum six times before she’s satisfied.”

“This is insane, man. How is it possible I didn’t know this?”

“There are lots of things you don’t know. Anyway, trust me that she’s crazy horny right now and I think she’d let you fuck her. Can you get into that?”

Russell’s eyes were big.

“Shit, man, the only girl I ever even messed around with was my cousin at a family reunion two years ago. I don’t know nothin’ about fucking, much less how to make a woman cum six times!”

“She’ll teach you that,” said Bobby. “She seemed to have great fun teaching me how to make her happy.” He grinned. “Actually, she taught me how to make other women happy, too.” It was only a little lie. Russell didn’t need to know more, yet.

“Other women?” Russell’s voice rose. “Dude! What the fuck have you been up to?”

“I can’t tell you that unless you join the club,” said Bobby. “I’m not trying to pressure you or anything, but to be honest I could use some help. I just can’t share any details unless you’re doing it too.”

“So you’re fucking more than one woman and you want me to help you fuck them?”

“We’re partners in everything else,” said Bobby.

Russell looked over his shoulder at Julie, and then back to Bobby.

“I just can’t believe all this,” he said. “I knew white people were crazy, but not like this.”

“I’m not crazy and you don’t have to do anything,” said Bobby. “We can go on like always and pretend you didn’t hear anything today.”

“I can’t pretend I don’t know about this,” said Russell.

“So, do you want to find out what it’s like to fuck a woman or not?” Bobby just waited. “I know you do,” he added, when Russell didn’t say anything.

Russell looked over his shoulder again, and then turned and walked towards Julie.

“I’m Russell,” he said, standing in front of her.

“Hi, Russell. I’m Julie. So what did you decide?”

“I’m having a hard time believing that you and I could ... you know...”

“Fuck like bunnies?” asked Julie, brightly. “Russell, when you look like me men don’t line up to make you squeal. I lived without sex for twenty-five years and then I met Bobby and found out what I had been missing. I’m not in love with him. I just adore how he treats me in bed. You’re his best friend, and I’m just curious about you. That’s all.”

“Because I’m black,” said Russell, stiffly.

“Maybe a little, but I bet if I cut you and Bobby nobody could tell whose blood was whose. I just get really horny and sometimes I wonder what a guy other than Bobby might be like. We don’t actually have to do anything. I’d have fun just chatting with you while we drink iced tea.”

“You’re serious,” said Russell. His voice wasn’t as stiff.

“Russell, I have no idea if there will be any of the kind of chemistry I have with your friend, but if there is, I can promise you won’t leave here unhappy.”

For the first time Russell looked her up and down. She was probably thirty pounds overweight and it showed mostly on her bare arms and the bulging roll beneath her breasts. Those breasts were big and pillowy, too. Russell had never gotten to see real breasts before, other than his sister’s, when she was twelve and he was thirteen. He felt his groin reacting at the thought of what might happen to him.

“I’ve never ... um ... done anything,” said Russell, softly.

“Really? Well, then, the girls in your school are crazy. You’re a studly looking young man, to me.”

“No I’m not,” said the young man who was five-eleven and weighed a hundred and seventy-five pounds.

Bobby came up and interrupted them.

“I have to go. Are you guys good?”

Julie looked at him.

“What if I like him better than you?” she asked.

Bobby laughed.

“I’m not worried. You okay, Russell?”

“I’m okay,” said the black man. “Go on and do whatever your mom wants you to do. I’ll be fine here.”

“Here?” said Julie. “Ooo, goody. I’m getting excited. Can I offer you some tea, Russell?”

“A shot of whisky would probably be better,” said Russell.

Julie laughed and turned back to the door. She looked over her shoulder when she opened it.

“I don’t want your senses dulled by liquor,” she said, her voice sultry. “You coming, or not?”

Russell looked at Bobby, who was edging away, and then back at the woman who was offering him something he’d never have believed any woman would offer him, probably ever. If he went in this house, his life would change in a huge way.

“I like sugar in my tea,” he said, moving toward her.

“That’s good,” she said. “I like sugar in my men.”


“I know I’m coming on a little strong,” said Julie as she set a glass of tea down in front of Russell with one hand and a sugar bowl beside it with her other. “Bobby is pretty remarkable and I think he has kind of spoiled me. I don’t quite know how to behave anymore when there’s a strong, handsome young man around anymore. I’m not a slut. I promise you that. I’m babbling a little bit because I’m nervous, too.”

“I don’t think you’re a slut,” said Russell, as he dumped one heaping spoonful of sugar into his tea and used the same spoon to stir it.

“Yes you do,” she said, calmly. “I only met you ten minutes ago and I’ve already propositioned you. I’d say I was a whore except I’m not charging you anything.”

“You’re not a whore, either,” said the boy.

“How old are you?”

“Seventeen.”

“Seventeen,” she sighed. “I was seventeen only eight years ago, but your seventeen-year-old world is so very different from mine.”

“What do you mean?”

Julie calmly took her T shirt off. She had on a plain, white, utilitarian bra that was stuffed full to overflowing with very white looking breasts. She pinched the area below the bra, squeezing two inches of excess stomach.

“I was even fatter than this back then,” she said. “I’ve actually lost ten pounds since Bobby first made love with me. He motivates me to work harder to take the weight off. I’ll never be a skinny woman, but maybe one day a man will ask me out for coffee.”

“Do you want to go out for coffee sometime?” asked Russell, as he stared at her deep cleavage.

“They’re thirty-eight EE’s” she said. “I know everybody wants to know what size they are. I think people are kind of awed by how much there is.” She cupped her bra-encased breasts and bobbled them.

She saw him lick his lips and said the exact same thing she’d said to Bobby on that very first fateful day when her whole world had changed.

“You want to see them?”

Russell’s eyes jerked up to look at her face.

“You’re not a slut or a whore. Maybe you’re carrying some extra weight, but you have beautiful eyes and I like the shape of your face,” he said.

“Ohhhh, boy, you’re going to get sooo laid,” she sighed.

“I would say don’t call me boy, but right now that seems kind of trivial,” said Russell.

“I wasn’t calling you boy,” she said. “It’s just a turn of phrase.”

“I know,” he said. “But it has evolved from slave times. Back then you might have said, ‘Boy, don’t you stare at my lily white titties.’ I get it that you didn’t mean it that way. Maybe my reaction is just a learned one.”

“It can’t be easy, living in a town like this when you look like you,” she said.

“It’s not so bad,” he said, shrugging. “Most people are cool. What makes it hard is that doesn’t seem to extend to dating their daughters. Every girl I’ve asked out either made up some excuse not to go out with me or said her parents wouldn’t let her or whatever.”

“I can understand how a girl might be uneasy about dating a black bo-” She stopped and licked her lips. “Man,” she went on. “It’s normal to fear the unknown and in terms of romance you’re a very unknown. I’ll be honest that I’m very curious about what your skin will feel like. I know it’s silly, because I know your skin will feel just like Bobby’s skin. But something in my mind makes me notice how black you are. Is that racist?”

“No,” he said. ‘You’re not showing prejudice, discrimination, or antagonism toward me. People get all wrapped around the axle if race is noticed, but if that doesn’t involve any of those three things then it isn’t racist.”

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