Accidental Gigolos - Cover

Accidental Gigolos

Copyright© 2024 by Lubrican

Chapter 8

Romantic Sex Story: Chapter 8 - 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  

They stayed another hour, during which the boys tried to help Teri understand why this whole mess was happening. Since she was only sixteen, it was practically impossible for her to put herself in the shoes of an older woman, much less a married one. In the end, she agreed to meet one or two of the women to see if they could explain it any better than the boys had.

All of this, from the position of Bobby and Russell, was merely to ensure that Teri didn’t go blabbing or complaining to a parent and blow the whole thing up. Neither boy really paid much attention to how Teri was feeling about them and her newly-awakened libido. All her references to the kind of things she was feeling were couched in terms of “dreams” or “nightmares” and both boys assumed that would take care of itself.

They were, of course, teenagers like Teri and, while they had a shit-ton more sexual experience than other men their age, that didn’t mean they had enough life experience to traverse the minefield that is normal puberty. If anything, they had been shielded from some of the angst involved in short-term romantic relationships and uncertainty about their own self-image.

The boys chose Julie and Betty and then explained to each of them what was going on and why they wanted Teri to be able to “interview” them. Since the alternative was possible scandal, both women agreed, but only if the boys were present, too. That was fine with them. None of the other women were informed of the danger, since it wouldn’t do any good and all they’d do was worry and fret.

Julie had been chosen because she was only nine years older than Teri. Betty was chosen because she was old enough to be Teri’s mother, and because Teri had been raised in a house where she listened to her elders and did what they said to do. It was hoped that Betty could use ‘parental’ influence on Russell’s sister.

The gathering happened on a Saturday, when Teri could be gone from home for a few hours without it causing interest. Teri and Russell both left home at different times that morning and Bobby picked them up at Friendship Park. They drove to Betty’s house and she let them in with a smile that Teri could see was genuine.

Teri already knew this woman was forty, which was only one year older than her own mother. Her initial impression of Betty was that she didn’t look forty. She looked like she was a gym teacher or something, with fit muscles and an erect posture. Julie was sitting at the kitchen table, which was where the women thought might make a comfortable setting.

What nobody expected was for Dan to be there. He was sitting in one of three chairs that had been placed against the wall.

“What are you doing here?” asked Russell.

“Betty told me what’s going on and I figured I might be able to shed some light on why things are the way they are,” he said. “If it’s too much of a distraction, I can leave, but I think she should hear what I have to say.”

“I do, too,” said Betty. “In fact, I think he should start.”

She went to him and leaned down to kiss him before she seated herself. When Bobby and Russell sat down, only Teri was left standing.

“Sit down, sit down,” said Julie. Only someone who knew her well would have detected the nervous tone of her voice. “I’m Julie.”

Teri sat, but only on the edge of the chair, as if she wanted to be ready to flee if that’s how things ended up.

Dan rose and went to stand behind Betty, where Teri could see both him and his wife.

“My name is Dan,” he said. “Betty is my wife. We’ve been married twenty-one years. We have one child, who is in college right now.”

He put his hands on Betty’s shoulders.

“Have you ever heard of something called erectile dysfunction?”

“You mean Viagra?” Teri proposed.

“Viagra is used to treat some forms of erectile dysfunction. I have ED but Viagra doesn’t work for us. We were trying to have a second child when I was affected. I haven’t been able to make love to my wife for eight years.”

Teri blinked. She hadn’t known what to expect, but she’d never thought of anything even close to this.

“It’s very difficult when two people love each other and cannot express that love physically,” he said. “It’s frustrating and can destroy a marriage.”

Betty put her hand up on top of one of his.

“I have some friends I play cards with, once a week,” she said. “I found out that some of them had similar problems and that one of them had finally done something about it. She decided to have an affair.” She looked at Julie, who took over.

“I’m single and I’m sure you can see why. I’m fat and not pretty, like you. I’d kill to have your body. Anyway, Bobby has been mowing one of our friend’s lawn for three or four years. On her birthday last year, her husband forgot it completely. There were other problems too, that you don’t really need to know about, except he wanted her to do things she didn’t really want to do. Then he forgot her birthday. But Bobby remembered it and when he went to mow her lawn that day he wished her a happy birthday.”

Teri reflected on how Bobby had always wished her a happy birthday, too. He always remembered her birthday.

“For someone as young as you, it may be difficult to understand, but when Bobby was kind and thoughtful, it kind of twanged something inside our friend. Neither of them intended for anything to happen but she invited him in and he listened to her. Again, you might be too young to understand, but a man who is kind and thoughtful, and who listens to a woman, can become very attractive to that woman if her own husband is none of those things. So she started an affair with Bobby that day.”

“She was one of the women you saw that night,” said Bobby from behind Teri. “The one with the brown hair.”

“Our friend was very glad she started that affair. Bobby gave her something she needed badly. Well, we all noticed it at the next card game. She was all bubbly and happy and of course we had to know why. When she told us, I said I wished I could get laid and she offered to introduce me to Bobby.” Now Dan spoke up again. “We had spent many anguished hours with me trying to be a man and not succeeding. There are other ways to make love and we did some of that, but it isn’t as satisfying as the real thing. At one point I felt like Betty should have an affair so she could enjoy real sex occasionally. I knew she loved me and I loved her. I suppose it sounds weird to you, but I wanted her to be as happy as she could be. So when she came to me and told me about this young man she could meet, I told her she should do it. Then we could talk about it afterwards and decide whether it had been good, bad, or something in between. Does any of that make sense to you?”

“I know I’m supposed to go yuck, but it sounds kind of romantic to me,” Teri said.

“It was romantic,” said Betty. “He was sacrificing our fidelity so that I could enjoy what every married woman wants to enjoy. I wasn’t sure I was going to do anything with this boy, but I couldn’t have loved my husband more in that moment when he said I could.”

“So ... you did it?” asked Teri.

“I got to know him first. Remember, I was old enough to be his mother, so it was very strange for me. But he was a good kid and fun to be around. And when I finally gave in, I’ll be honest. He rocked my world. Our friend had taught him some things, ways to make a woman happy, and he let me teach him even more. Pretty soon he was kind of like my living dildo. I know that sounds harsh, but it really was like that. If I needed him I could call and he’d come for a visit and I’d be relaxed again.”

“I was next,” said Julie. “I’m twenty-five and when I met Bobby I had never been on a single date. I knew no man would ever be interested in me. But I still wanted that. Every girl wants that. Russell has told me a little about what it’s like for people who look like you two to live in a town where everybody looks like me.” She blinked. “Well, not like me. Most people are better looking than I am.”

“Julie?” Bobby’s meaning went far beyond that one word, posed as a question. Even Teri heard the censure in his voice.

“I’m sorry,” Julie said. “I know my friends think I’m beautiful and I know Bobby and your brother think I’m beautiful. It’s all a little new to me, though, and I don’t think I fully believe it yet.” She leaned toward Teri and used a stage whisper when she spoke again. “I’m not supposed to say I’m ugly, or plain, or fat.”

“Julie!” Bobby said again. This time it was clearly a chastisement.

“Okay, okay, I’m gorgeous and you’re helpless around me. I get it.” She looked back at Teri. “Anyway, Betty and our friend introduced me to Bobby. I’m going to use a bad word, but it conveys just the right meaning. Have you ever heard of a ‘charity fuck?’”

“Good grief, Julie,” came Bobby’s voice.

“Well? That’s what it was, that first time.” She looked at Teri again. “I’m not doing this well. I knew what was going on when I met Bobby, but all we did was talk for a long time. He was the first male to really listen to me and have a real conversation with me. And I’m not sure exactly how it happened, but suddenly he asked if he could see my breasts and I let him and there was something in his eyes that made me feel like I needed to pee. Do you understand?”

Teri nodded. That’s how she’d felt as she watched Bobby and her brother thoroughly fucking four women.

“And even though I knew he was only play acting I went through with it. I expected him to get up and leave once he was finished, but he didn’t! He stayed there until he could go again and this time I knew he was there because he wanted to be there and I almost lost my mind! And it wasn’t the last time, either. He really did like me. It wasn’t love or anything. He just liked me for the person I am. And I know people would say all he wanted was sex, but I knew that wasn’t true. Sometimes we just cuddled and talked, or kissed a little. He just liked being with me and that meant so much to me that I know I’m going to go insane when they go off to college and I can’t call one of them up when I need them.”

This was an opening to let Teri ask a question and she jumped on it.

“Okay, I get what you were saying, but how did you meet my brother?”

“Ahhh, Russell,” said Julie, and it sounded like she was talking about a sweet dessert she was about to eat.

“There were five women by then,” said Bobby. “I had work and other stuff and I ... um ... couldn’t –”

“We were hard on him because we were very appreciative of what he was doing for us,” said Julie. “So one day when I had made an appointment with him he brought Russell with him. Bobby couldn’t stay but Russell did. And I found out he was just as thoughtful and kind as Bobby.”

My brother?” said Teri. “Kind and thoughtful?”

“Yes,” said Julie, firmly. “You have a very special brother, Teri. There are five women who depend on him, especially now, before he goes off to college and meets some pretty girl who will snatch him up and who will not be willing to share him in the future.”

“I wanted to ask about that,” said Teri. “They said something about ... babies?”

It was Dan who spoke next.

“I could not make my wife pregnant and we wanted another child,” he said. “I suppose we could have gone to a clinic and spent ten thousand dollars trying to use in vitro fertilization, but we both had a lot of respect for both Bobby and Russell and I couldn’t think of any other donor I felt would be acceptable. Betty agreed, so we asked the boys if they’d be willing to help us out in that way, too.”

“I know how you met Russell,” Teri said to Julie. She turned to look at Betty. “How is it that you met him?”

“The five of us in the card club are very close, like sisters,” said Betty. “We have no real secrets, so the rest of us found out about both Bobby and Russell. Like Julie said, they are both very special to us in the club. The three who aren’t here today are all in terrible marriages and were thinking about divorce before Bobby and Russell came along. But if a woman just files for divorce, sometimes the fighting gets brutal. If a woman turns up pregnant, though, and her husband knows he didn’t get her that way, he may kick her out and if she doesn’t ask for much, the divorce will proceed much more smoothly.”

“That’s a kind of piss poor reason for having a baby,” Teri commented.

“Your brother said the same thing,” said Julie. “But things change and now all of us want children just to love them and raise them. Bobby and Russell agreed to be donors for us. They know they’ll never get to come out in public as the fathers, though I would not be shy about that at all. And we would all have a piece of one of them after they left. That’s how special they are to us.”

“So, basically, you’re telling me that my brother and his best friend can provide mind-blowing sex of the type that makes a woman want to have his baby?”

“It’s much more complicated than that,” said Betty, “but that’s the gist of it.”

“And all five of you really, actually, positively want to get pregnant?”

“That is what we were trying to do when you spied on us,” said Julie.

“Wow,” said Teri, softly.

“So can you see how it might cause problems if you decided to ... share ... this information with anyone?” asked Betty.

“Can I talk to the two of you privately?” Teri asked the two women.

“Of course,” said Betty. “Boys? Go make yourselves useful and get us some lunch.”

“Taco Bell?” asked Dan, standing up.

“This is why he has erectile dysfunction,” said Betty in a stage whisper, with one hand blocking her lips from her husband.

“There are many more factors in play than the fact that I’m twenty pounds overweight,” he said, with a dignified voice.

“I know, Dear. I love you and you know I love you. But we are all sitting here because of all those factors and I get to be a little snippy about it.”

To Teri’s astonishment her brother got up, went to Betty, and leaned down to kiss her in what could only be called the kind of kiss a husband gives his wife.

“Be nice,” he said, when he rose. “If it wasn’t for his ED you would never have met me.”

“I suppose that’s true,” said Betty, whose eyes were bright.

Dan came and kissed her in exactly the same way. It felt to Teri almost like he was erasing Russell’s kiss with his own lips, like wiping a dry erase board clean.

Or writing on top of the kiss with his own, making the words on the board seem legible, but fuzzy.

“Is Taco Bell all right with everyone?” asked Betty.

Dan got a pad and took orders. When Betty ordered a taco salad Teri spoke.

“Did you know the taco salad at Taco Bell has the most calories of anything they sell?”

“I did not know that,” said Betty, frowning.

“Yeah. I always thought it was ironic they could take a word that the whole world thinks of as wholesome and good for you, and make it the fattiest thing on the menu.”

“She’s right,” said Julie, who had served countless taco salads to her customers.

“Bastards,” muttered Betty. She looked at Julie. “Is there anything on the menu that won’t make me fat?” Teri answered instead of Betty.

“Well, you’re certainly not fat now, so if you’ve been eating Taco Bell you haven’t been overdoing it, but the answer is no.”

“Thanks for talking about fatness,” complained Julie. “Here we were, having a nice time, getting to know someone, and fatness enters the conversation to ruin everything.” Her voice was much milder than her words.

Teri was a little less astonished when Russell went to the hefty woman and kissed her, too. This time he cupped one of her breasts and squeezed it.

“You’re not fat,” said Russell. “There’s just more of you to love.”

“Not fair,” complained Julie. “I don’t get you again until Monday and now I’m going to be all worked up until then.” Julie blinked, looked around, and said, “I’m sorry. I get a little crazy around him.”

“Obviously,” said Bobby.

Then another amazing, astonishing, mind-blowing thing happened to this girl who was already overstressed.

Bobby Grisham, her brother’s best friend and the boy she’d had disturbing, sexual thoughts about, came and leaned down with his face inches away from hers.

“Thank you for being cool about this. I know it has to be freaking you out.”

And then he kissed her on the lips.

And it wasn’t a mere peck.

“Dude!” she heard her brother say. “Don’t make me kick your skinny, white ass!”

Bobby stood.

“All I did was thank her for listening and discussing all this.”

Julie leaned toward Teri. There was no stage voice this time. She spoke clearly and in a normal voice.

“That’s the first thing he does. He’s just nice, and polite, and he makes you feel good. Then, before you know it, you’re in bed with him. Be very careful about this one, Teri.”

“Dude,” growled her brother. “I really am going to have to kick your ass.”

“You and what army?” teased Bobby.

Teri was a little weak, as she contemplated that five-second kiss. He was bantering with her brother, just like always. They both looked like they always did.

But they weren’t just like they’d always been. And while she’d kissed a lot of white boys on the dates she went on, none of them had kissed her with a tenderness and depth of feeling that made her want another kiss like that. She liked kissing boys. All the kisses were different, but almost all of them were fun. This kiss made her radar go wild, like it did when she decided the date needed to be over, lest something forbidden happen.

Then the men trooped out and she was left alone with Betty and Julie.

They had already made themselves vulnerable and showed her everything, almost literally. If you counted what she’d seen through the window, Julie had showed her everything.

Now she felt like she could make herself vulnerable.

Now she could tell someone – another woman – about the feelings that had been torturing her.

When the door closed behind the men, she relaxed, visibly. Her face turned from watching them leave, toward the two women.

“Your brother can be a little impetuous,” said Betty.

She smiled.

“Now, what do you want to talk about?”


Through all of this, from the moment Teri peeked through a window and saw what real sex looked like, to the point where two grown women treated her like she was a grown woman and explained it to her, rather than threatening her or bullying her, there was a small but very fundamental change in Teri’s psyche. Her personality didn’t change. Most of her opinions about life in general didn’t change. She was still a junior in high school with a lot of friends and she still planned on going to college to get a degree in political science.

It has been explained why Bobby and Russell were not normal seventeen year old young men. Now it must be understood that Teri was no longer a normal teenager in the sense that she had knowledge of a kind that most teens do not. She had knowledge of why a woman – multiple women – might choose to have a stable of men, including her brother, who could be called on like gigolos to come “service” the women upon demand. That concept, in and of itself, is something very few people outside the group would even try to understand, much less retain inside them as if it was just normal, private information that wasn’t for public consumption.

What did change was her attitude toward her big brother. He hadn’t changed, either, on the outside, but their relationship was irrevocably altered in a phenomenal way. Both of their parents would notice this within a few weeks, but both teens expected that and were co-conspirators, of a sort, in responding to that.

The shift in behavior was that she wasn’t as argumentative, and was more amiable than she’d been in the past. She didn’t make snide comments anymore. Russell didn’t call her “Squirt” any longer, and actually apologized for that nickname, confessing that it meant she was the product of a literal squirt of semen from her father’s balls. He got a punch in the arm and was then forgiven. He also gave her hugs, but not in front of anyone.

That part of their relationship was very complicated.

The reason for that was because when Teri cried and moaned about her unwelcome, sexual dreams, and asked the women how to get rid of them, their advice was not what she expected.

“You can’t un-see those things in your mind,” said Betty. “You need to turn them into something you don’t mind.”

“It would actually be even better if you could use them as your own, private happy thoughts,” said Julie. “I’ll give you an example. The very first time I had sex with your brother he blew my mind. I was a virgin, except for Bobby, and Russell unleashed something in me that felt dangerous. That very night I had a dream that the head of his penis had pulled my IUD out.” She blinked. “I had an IUD implanted when I started making love with Bobby. Do you know how they work? There’s a little tail that sticks out of the cervix, kind of like the string of a tampon. Well, Russell is really long and he goes really deep.”

“Too much information, Julie,” Betty interrupted in a calm voice.

“No it’s not,” said Julie. “I kept having these dreams that because he was so deep, the head of his penis somehow pulled my IUD out and I had a little black baby. I watched my tummy swell up and watched as this little brown thing came out of me and wanted to suck milk from my breasts. It was awful. I knew it probably couldn’t happen, but there have been instances where it did happen. Anyway, I couldn’t resist him. I can’t resist Bobby, either. Because of who I am and how I look, they’re the only game in town. So I knew I’d let Russell make love to me again and that I’d probably keep having this dream. And I did. It was always Russell who got me pregnant in the dream, but sometimes the baby was black and sometimes it was white.”

“Get to the point, Julie,” said Betty.

“I decided that if I had his baby it wouldn’t be the end of the world and turned it into one of my favorite dreams to have. Eventually I had the IUD taken out and now that dream is going to come true. One of them will get me pregnant and I’ll have either a little brown baby or a little white baby.”

“Wow,” sighed Teri.

“Wanna hear my bad dream?” asked Betty. “I can tell it in a much shorter version.” She glanced at Julie, who stuck her tongue out.

Betty took a sip of coffee.

“I dream I have twins. One of them is Bobby’s and the other is Russell’s.”

“You never said anything about that,” said Julie.

“I think I can handle one,” said Betty. “Two, on the other hand, would probably wreck my life.”

“Wouldn’t a mixed race baby ruin your life, too?” asked Teri. “I mean you’re married to a white man and everybody knows it.”

“I don’t care what others think,” said the older woman. “Whatever color baby I give birth to will be my son or daughter and both Dan and I will love it and cherish it. If it’s a mixed race baby we’ll also try to protect it from a racist world.”

“Good luck with that,” said Teri. “It’s a very racist world.”

“Not here,” said Julie. “But enough about us. Let’s get back to you. I don’t have a brother, so I can’t tell you how I’d feel if I wanted to see him naked and hug him naked and those other things in your dream. The nearest thing I’ve done to that is my relationship with a black man.”

“I do have a brother, but I don’t think of him that way,” said Betty. “I think what you can try to do is think of him as someone who isn’t your brother. He’s just this black guy you know, but who you can’t have sex with. Isn’t there anybody at school you’ve had naughty thoughts about but you knew nothing would ever happen? Maybe somebody else’s boyfriend?”

“Yes,” said Teri, slowly. “There was also a substitute teacher we had one time who I had some ... um ... thoughts about.”

“Well, there you go,” said Betty. “That’s perfect. You wanted these men, but they were unavailable. When you dream about them, though, that’s not a bad thing. It’s just fodder for masturbation. You can have them in your dreams and fantasies and when you start thinking about them, you just Jill off and have a nice, calming orgasm. Then you can put them away until next time.”

“Hmmm,” Teri replied. She didn’t even think about trying to deny she masturbated. She’d never admitted that to anyone else, not even on sleepovers. She’d only been invited to two of them, and while the subject had come up, she had just observed, instead of taking part in the conversation. And the fact was that she did masturbate. She masturbated what she thought of as a lot. She masturbated after all those dates she ended because she got too excited. During the week, she masturbated thinking about lots of movie stars and men or boys she knew or had seen somewhere. She loved masturbation. It did exactly what Betty had referred to. It took the edge off and she could then think of other things, like homework or whatever.

She had, in fact, masturbated after seeing the orgy and that’s when the problems began. In the past there had been hazy, indistinct penises involved in her masturbation fantasies. On that night, however, and ever since, the penises that intruded on any of her masturbation sessions were either Bobby’s white one, or Russell’s black one.

That’s why she was so freaked out she was afraid she’d have some kind of breakdown.

After talking to Julie and Betty, though, she felt much better. Actually, just meeting Betty and Julie had started a relaxation inside Teri. They looked, talked, and seemed so normal! She hadn’t talked to all that many grown up white women. Mostly she talked to teachers. Sitting there with these two, who accepted her as just another woman, had been fantastic on one level, and unsettling on another. Those kisses Russell had given the women had been unsettling, but then seemed to somehow be normal. It happened right in front of Betty’s husband, who didn’t make a sound. And then she’d been able to unburden herself.

Now, if she thought of either one of them on top of her, or under her, or inside her mouth, all she did was save it until she could get alone and rub a little.

There was only one little fly in the ointment.

That fly lived in the bedroom right next to hers, and occasionally went to or from the shower in very little clothing.

That fly was ... available ... in one sense. He was more than a mere character in a sexual fantasy.

He was a living temptation to engage in something that, before she talked to Julie and Betty, she would have thought of as a perversion.

Now, she thought of it as what Betty had called them: naughty thoughts.


Teri’s confession to her two, new, very unexpected friends was intended to be private, on Teri’s part. That’s why she had asked if she could speak with them privately. To be technical about it, though, she never asked the women to promise not to tell either Bobby or Russell about what they learned.

Betty, being better able to see the possible potholes in the road Teri was trying to move along, thought both boys needed to know they were the subjects of Teri’s sexual fantasies. They needed to know so they didn’t unintentionally tease or torture her.

For example, on two occasions Bobby had referred to Teri as “beautiful.” He had said, “Move over, Beautiful, I need to get by you.” The other time was when he got to the house and she opened the door and he’d said, “Well! You’re looking particularly beautiful tonight. You going on a hot date?”

Bobby had never intentionally teased Teri. He’d just been “Bobby.” Russell, on the other hand, teased her unmercifully, though not in a sexual sense. On the other hand he never called her ugly, or said boys wouldn’t be interested in her. To the contrary, if a guy got out of line with her (in Russell’s opinion) he stepped in to “straighten things out.” Before this she’d thought of that as butting into her business. She could take care of herself. She didn’t need him mucking about in her life.

When Bobby had kissed her, however, and Russell had objected, it was almost like Russell had said, “Back off, Dude. She’s mine.”

That shift in how Teri contemplated her brother’s protective stance made him seem much more attractive than he’d ever been before.

She still didn’t want anything to actually happen, and neither would have Russell, except for the results of her wanting to know where he was going on that fateful night she got an eyeful she could not forget.

What she did not know, however, was that Betty had had a little counseling session with both boys.


“She can live with the fact that her brother has relationships with all these women,” Betty told them, a day later. “She still thinks of it as weird, but she can accept it. What’s bothering her is that she’s had a crush on you, Bobby, for quite a while, and now that she’s seen your handsome penis, she’s even more interested.”

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