Accidental Gigolos - Cover

Accidental Gigolos

Copyright© 2024 by Lubrican

Chapter 4

Romantic Sex Story: Chapter 4 - 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  

“Can I come in?” Trudy asked, when Cathy opened the door.

“Yes. Ron isn’t here. We can talk.”

“Talk?”

“I know why you’re here,” Cathy sighed. “Julie has such a big mouth.”

“She was just happy for you,” said Trudy.

“I guess I can’t complain about that,” said Cathy. “You want to go shopping?”

“Maybe later. Right now I need a cup of coffee. I didn’t make any before I came over. I didn’t sleep so well last night.”

They were seated at the kitchen table, each nursing a cup of coffee when Trudy said, “So...?”

“I don’t kiss and tell,” said Cathy.

“Of course you do. Not counting Julie you were the first one to get Bobby in bed and you told everybody about it in great detail.”

“Well, it was exciting,” said Cathy, sounding injured. “I had to share it with my friends.”

“You had to share him with your friends,” said Trudy, severely. Then she smiled. “But we’re all delighted you did.”

“And now you get to expand your world with Bobby’s best friend and be just as delighted,” said Cathy

“So you did do it,” sighed Trudy.

“I admit to nothing,” said Cathy. “Do you want me to set you up with him?”

“You can do that?” asked Trudy, weakly.

“Julie introduced me to him. I can introduce him to someone else, can’t I?”

“I wouldn’t know how to act,” said Trudy.

“You would act exactly like you did with your math teacher. And I promise you, you would not be sorry.”

“Fuck! I’m horny!” whined Trudy.

“I’m not,” said Cathy, smugly. “I’m almost never horny for more than an hour these days.”

“Liar,” snapped Trudy. “They aren’t on call, like a pair of gigolos.”

“How do you know?” asked Cathy. “I bet I could have either Russel or Bobby over here within an hour and you’d be naked and squealing.”

“You talk big,” said Trudy.

Cathy held up one finger and went to pick up her phone. She tapped it twice and then punched a number. She put it on speaker and it rang.

“Hello,” came a male voice.

“Russell? This is Cathy. Are you free?”

“I can be,” came the voice.

“I have a friend. She’s kind of in the same situation I am. Would you be willing to help her like you help me?”

“If you want me to,” said the voice. “Does Bobby know her?”

“He does,” said Cathy.

“Then no problem. If you know her and Bobby knows her, that’s all I need to know.”

“Thank you, Sweetie.”

“Your place?” asked the voice.

“Uh huh. One thing ... you might have to satisfy both of us. I’m awfully horny, too.”

“No problem. I’m looking forward to it. I’ll be there in half an hour.”

The line went silent and Cathy looked at an astonished Trudy.

“He’s coming here!” gasped Trudy. “I can’t! Not with him! Not now! I’m not ready!”

“Breathe,” said Cathy. “In through the nose and out through the mouth. Calm down. He’s going to rock your world.”

“That’s what I’m afraid of,” moaned Trudy. “I want Jerry out of my life, but that doesn’t mean I want a new man to snare me in an emotional trap.”

“It’s just getting laid,” sighed Cathy. She knew that wasn’t actually true, but she didn’t want to scare Trudy away. She knew that Trudy, like she had, would welcome what Russell could offer.

“I fell in love with a forty-five-year-old man when I was fourteen, Cathy!” whined Trudy. “I am very vulnerable to a man like this.”

“So, be vulnerable. He won’t hurt you; quite the opposite. When you leave here today you won’t have a care in the world. Trust me.”

“I don’t think I can do this.” Trudy paced.

“Think of it this way,” said Cathy. “You’re twenty-eight and he’s seventeen. You’d never be seen with him on a date just because of your ages. So there’s no chance you’ll fall in love with him. It just couldn’t happen. He’s a teenager, Trudy.”

“And I was a teenager when I fell in love with Tim Brimlow, who was in his mid forties!”

“That turned out fine, didn’t it?” insisted Cathy. “You went your way and he went his. You both ended up happy, didn’t you?”

“I only stopped because he made me stop,” growled Trudy. “Back then I’d have happily let him knock me up. I was besotted with the man! But he was smart enough to break things off.”

“Well, there you go. You’re older and wiser, now. Nobody’s going to fall in love with anybody else. I understand how a young girl could be swept off her feet by a handsome older man, but how many times have you ever heard of that happening the opposite way? Boys just don’t fall in love with older women. They fantasize about fucking them, but not about marrying them. This will be good for you. Hasn’t Bobby been good for you?”

“You know he has,” grumped Trudy.

“All this does is expand your choice a little. We’re kind of Bobby’s harem, if you think about it that way. What’s wrong with there being two sultans?”

“You make it sound so simple,” groaned Trudy.

“It is simple. When he gets here just talk to him a little. Think of it like an interview. Do you know what I did on my first time with him? I asked him to tell me what he wanted to do with me if there were no rules. When he said he would want to see my breasts, I told him I’d do that, but he had to show me his penis. I didn’t time it, but he was probably on top of me within ten minutes.”

“I’d freeze up and look like an idiot,” said Trudy.

“Okay. How about this? You heard me tell him I was horny. When he gets here he could take care of me first. You could kind of watch us to see what he’s like.”

“That’s the most insane thing I’ve ever heard of!” gasped Trudy. “I can’t just watch you have sex with a stranger!”

“Why not? We’re friends. I mean sure, we don’t hang around each other naked and all, but I’ll tell you right now you could be stark naked, standing right beside us, and I wouldn’t pay you any attention at all. When I’m with him the only thing I can think about is what I’m feeling. He’s just as good as Bobby. I’m telling you, there’s no down side to doing this, Trudy!”

“Well, I’m not getting stark naked and standing beside you like that,” growled Trudy.

“That’s fine. I’m not trying to get you to do that. All I’m saying is that if you saw him doing ... that ... it might calm you down and you’d be less worried about it.”

“Why are you so intent on making me fuck this boy?” yipped Trudy. “Things are fine the way they are. If you want to do it, that’s great, but that doesn’t mean I have to.”

Cathy took a breath. She realized she was tense. Trudy was right.

“I’m sorry. I just have such a good time with him that I wanted you to feel that, too. I mean we all share Bobby, so I just assumed we might want to share Russell, too. There’s no pressure. When he gets here I’ll just tell him there was a screw-up and that you’re not the friend I was talking about when I invited him over here. Okay?”

“Okay,” said Trudy, who should have felt good that she’d “won” the argument, but somehow didn’t. She jumped as the doorbell rang.

“That’s him,” said Cathy. “You hang out in the living room and when we’re finished you and I can go shopping. We’ll both have a nice day.” She smiled widely and got up to go let a stranger into her house; a stranger she was going to let mount her and fuck her; a black stranger who, like Tim Brimlow had done so many times back when Trudy was fourteen, would flush her friend full of his black seeds. Trudy wanted to cry.

But then there were voices and Cathy brought him into the kitchen and said, “This is Trudy. She’s another one of my friends. We’re going shopping after you leave.”

“Hi. I’m glad to meet you,” said the tall, handsome young man, who carried himself as if he was much older than seventeen years. His smile looked genuine and he sounded as if he really was happy to meet a random, strange white woman. Then, as she saw Cathy’s hand drift to interlace with the darker fingers of the lover she was going to go to the bedroom with, she thought, ‘Of course he’s happy to be here. He gets to fuck a grown woman. What boy would turn that down?”

“I’ll try not to make this too long,” said Cathy. “You can watch TV if you want to. You can watch You Tube videos, too.”

“Right,” mumbled Trudy.

Somehow, it never occurred to her that she could just leave and come back later.

As her friend led her young, black lover to the bedroom, Trudy looked at the doorway to the living room. She stood up, but before she could take a step, she heard Cathy’s passionate voice say, “Thank you so much for dropping everything and coming over.”

“You know how much I love spending time with you,” came the deep voice of the man she was with. He sounded like a man, too. “You want to start out on top this time?”

“Mmmm, yes,” said Cathy. “I love it so much when you get deep in me like that.”

Then the voices became muffled as, apparently, they left the hallway and entered Cathy’s bedroom.

Trudy had taken three steps toward the living room when she realized she could still hear the muffled voices. And she had not heard a door close.

‘That bitch!’ thought Trudy. ‘She left her door open. It wasn’t an accident when she invited me to watch. She knows I’d want to watch. But how could she know that? How could anyone know that?’

What she was thinking about was another part of her life she thought of as perverted. Tim Brimlow got put in that category because he was an adult who, legally speaking, molested and raped a girl. She hadn’t felt like there was anything wrong going on, back then, and she hadn’t felt like she’d been molested. She certainly didn’t feel like she’d been raped. It was only later that society’s norms made her think of it that way. But then, after she was properly married, Jerry had talked her into going to a sex party. He’d said it would be fun and that she’d be glad she went. She knew he was glad he went, because she saw him with the host’s daughter, who couldn’t have been more than sixteen. He made out with her right in front of everybody and nobody said a word. She knew he’d taken that girl to a bedroom, too. In the meantime she tried to become invisible. Her sensibilities were shocked as she saw other people getting naked and having sex, right out in public.

“You like to just watch, too, huh?” came a voice at her left side. She looked to find a man standing there. “That’s my thing,” said the man. “I love to watch. It gets me going. I don’t actually want to have sex. So, are you like that, too? Want to hang out together? You’ll get hit on less.”

In a daze she had acceded to his suggestion and she had found herself standing beside couples who were having sex. Her partner had introduced himself as Chuck and as she and Chuck went from couple to couple, Chuck got his stiff dick out of his pants and started stroking it. He didn’t try to cum, at first. He just rubbed his cock. He paid no attention to Trudy other than to tug at her to change scenes. And Trudy had found out watching other people have sex was a turn-on for her.

She had hooked up with Chuck at a second party Jerry dragged her to. This time she had stroked his hard prick as they watched other penises slide in and out of wet vaginas. She’d had to masturbate for an hour when they got back home and she knew that if she kept going to those parties, she’d eventually end up being one of those women Chuck watched getting fucked. She still felt guilty about Tim Brimlow and she didn’t need this kind of complication in her life. So she’d stopped going with Jerry to the parties. That’s when they began to drift apart. He happily went to parties to fuck other women, but he didn’t try to get her pregnant. He fucked her occasionally, but not with any intent or frequency that would let her conceive.

All this was why Trudy Carver was astonished when she found herself under Bobby Grisham, letting him rut in her and actually teaching him to do what she craved feeling. Over time she decided it was the disparity in ages that allowed her to think of it as non-romantic fun. It was the same thing Jerry was doing, except there weren’t a dozen other people around. And Bobby was so considerate, and passionate. When she was with him she always felt like she was the most important woman in the world, at least to Bobby.

A noise interrupted her reverie. It was Cathy’s voice, and it was a passion-filled moan.

Her feet took her towards the bedroom door before she could make them stop. She fought it unsuccessfully until she got to the open doorway and then stopped resisting. She peeked and actually felt her pussy get wet as she saw what was happening. The foot of the bed faced the door, so what she saw was their feet. Cathy’s knees were spread wide and her feet were planted on the bed. Russell’s very black ass was moving up and down. Then he stopped while he was all the way inside her and wiggled his hips sideways. Tim had done that to her way back then. It had driven her crazy. She’d tried to get Jerry to do that but he was too intent on cumming. He never seemed to care if she came or not.

That was one reason she was addicted to Bobby. Bobby did that, too and he wouldn’t leave until she’d had lots of orgasms.

“Ohhhh, fuck that feels good,” groaned Cathy. “I think I love you.”

“No you don’t,” said the young man as he drew almost out and then slid back in, slowly. “You love this.”

“Don’t spoil the mood,” panted Cathy. “Just fuck me.”

Trudy found herself inside the room, somehow, kneeling at the foot of the bed. She could see the heavy black sack that held his balls, and his dark penis splitting her friend’s shockingly pink pussy lips. Was this what it had looked like when Tim fucked her? The juxtaposition of his dark penis in her very pale pussy was startling and fascinating at the same time.

He went in and ground and Cathy had an orgasm. It was just like that and Trudy knew exactly how her friend felt. Bobby could do that; could manufacture an orgasm and then slap her with it when she wasn’t quite prepared to have it.

“You’re squeezing me,” panted Russell. “If you keep doing that I’ll cum.”

“It’s okay,” said Cathy. “You took the edge off and I told Trudy I’d go shopping with her.”

“I wish she was the friend you were talking about,” said Russell. “She’s really hot.”

“Don’t you worry about her. You’re here to take care of me.”

“I’m trying to but you’re going to make me cum.”

“Do it. Shoot your lovely sperm up inside me. Get me pregnant.”

“I told you that kind of revenge isn’t healthy,” said the boy, who was still sliding in and out of his lover.

“It’s not for revenge anymore,” panted Cathy. “Now I just want to have a baby.”

“Not my baby,” said Russell.

“I don’t care whose it is; yours or Bobby’s. I just want to feel life growing inside me. If I have a little brown baby I’ll just tell people I partied too hard in Oberlin one night.” Oberlin had a whole section of town with black residents in it.

“You don’t want to have a brown baby. Not in this town. Would you please stop doing that?”

But he didn’t pull out, and as Trudy watched, that heavy black sack jumped as he groaned and shot her friend full of virile, black sperm.

Cathy obviously wanted it, despite the danger.

Just like Trudy had wanted Tim Brimlow’s black sperm to take root in her fourteen-year-old belly.

She was glad that hadn’t happened, and that he was smart enough to cut things off. It would have ruined her life.

But it wouldn’t ruin her life now if she got pregnant.

Especially if the baby she had was obviously a mixed-race baby.

Jerry would have a fit.

And she would not care how he felt about it at all.


Trudy felt like she’d somehow entered an alternate reality. Everything had happened so fast! It was a blur, really. She knew she’d stood up and boldly walked to the side of the bed. She knew both lovers had turned their heads to look at her. She remembered saying, “I changed my mind.” Where things got fuzzy was when she somehow found herself kissing warm, full lips while hands slid all over her somehow naked body, making her feel like she’d break apart if she didn’t have an orgasm. A single, stark memory was there, when she looked down to see Cathy’s hand guiding a black penis to her sexual portal, and then saw that same juxtaposition of the dark column slowly disappear into her own pale pussy. When it got all the way in her she saw him slide his hips sideways and there was nothing after that except ecstasy.

Now, who knows how many orgasms later, she was finally relaxed, sitting up, impaled on his spike, as her body was rocked gently and he sucked her nipples.

“I need to cum,” came the voice of the complete stranger whose prick was all the way inside her.

“Okay,” she hummed.

“Can I cum inside you?”

He was considerate, too. Cathy had been right. She needed this. It was different than how she needed Bobby. This satisfied something deep in her psyche. She knew it was because he was black, but she also knew she would love actually getting to know this young man before she let him mount her again.

“Please do,” she murmured. “I love the feel of a man giving me his gift.”

He didn’t say anything. She just felt it happen. His penis swelled a little more and then flexed in her four or five times. As she heard his sigh of completion, she felt the warm wetness of what he was shooting in her.

“Thank you,” she moaned.

“Ohhh, trust me. It was my pleasure,” he whispered in her ear.


He had lain there, relaxed and sleepy, as Trudy got up and went to the bathroom to clean up. She felt odd walking around in Cathy’s house, naked and with a virtual stranger’s sperm leaking out of her. She had thought he’d be finished after he came, but he had necked with her while he waited to get hard again, just like Bobby did. She’d lost count of the orgasms she had but she knew he’d cum in her twice. She realized she was sitting on the pot, letting him drain out of her, but she couldn’t just lie there and let it soak in. She’d have to have him come to her house for that. She stood and walked without shame or angst to stand, nude, beside him.

“I need my lawn mowed,” she said. “Do you do that kind of thing?”

“Yes,” he said, sleepily.

“It’s a tiny lawn,” she said. “It won’t take you but fifteen minutes.”

“Okay.”

“Will you be able to stay an hour or two?”

“I will be most happy to stay that long or longer,” he said, opening his dark eyes and staring at her. “Maybe we can talk and get to know each other.”

“I’d like that,” she said. “I’m not usually this way.”

“You’re whatever way you need to be,” he said. “I’m certainly not going to judge you.”

“I’m going to leave, now,” she said.

“Do you have to? I think I could get hard again.”

She felt a thrill that he wanted to get hard again because she knew it would be primarily for her pleasure, rather than his.

“Save it for next time,” she said.

“I am so lucky,” he said, softly. “Thank you.”

“I don’t think you’re the lucky one,” she said. “I think we women are.”

“Bobby and I both feel incredibly lucky,” he said, proving that he knew she also let Bobby fuck her.

“I hope one of you gets lucky,” she said.

Russell was still trying to figure out what that meant when she left the room, fully dressed.

She stopped in the kitchen to give Cathy a hug.

“We can go shopping later, okay?”

“I’m so glad it all worked out,” said Cathy. “So ... who should we debauch next? Betty or Sarah?”

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