The Making Of A Gigolo (3) - Sherry Winston - Cover

The Making Of A Gigolo (3) - Sherry Winston

Copyright© 2007 by Lubrican

Chapter 4

Erotica Sex Story: Chapter 4 - Sherry was married to a man who was gone all the time. There were some troublesome indications that Sam, her husband, was fooling around on her too. She heard about Bobby from a friend, who described him as being capable of fixing anything - including a lonely heart. Meanwhile Bobby's mother is getting suspicious, and his oldest sister is worried about not knowing what to do on dates. Bobby's sexual world expands.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Reluctant   Cheating   Incest   Oral Sex   Masturbation   Petting   Pregnancy  

A week later, Bobby was again reading in bed, when Mary slipped into his room.

“How’d it go?” he asked. She’d been on her date that evening, and had been home at the prescribed nine o’clock.

“I let him kiss me,” she said, standing there, with her hair down.

“And?”

“It wasn’t like kissing you at all.”

“He’s better?”

She took a step towards him. “No way,” she said.

“I’m sorry,” said Bobby. “Maybe he’ll get better.”

“How did you learn to kiss like that?” she asked, taking another step closer. Her hands fluttered at her hips.

“A gentleman doesn’t talk about what he’s done with women.”

“That doesn’t make any sense, Bobby. You never go out on dates. You’ve never had a girlfriend. So how?”

“I still can’t tell you,” he said. “It would still be talking about a woman if I explained. I don’t do that.”

Mary knew him well enough to know he wouldn’t budge. She resumed on a different tack.

“I expected to feel the same, when he kissed me,” she said. “But it wasn’t anything like kissing you.”

“So what do you want?” he asked, knowing, somehow, what she wanted, but making her say it.

“Um ... I thought maybe ... you’d kiss me again,” she said, rushing the last words.

“I told you, you’re not ready for that,” he said softly.

“It’s just a kiss,” she whispered.

“Okay, kiss me, then,” he said, staying where he was.

She came to bend over him, and, as her lips touched his, he raised his hands to press them to her breasts. She jerked back, her mouth open wide.

“What are you doing?! You can’t do that!” she whispered urgently.

“It’s all part of kissing,” he said, smiling at her.

“No it’s not!” she said. “That’s something else completely.”

“Not to me,” he said.

“I just want a kiss,” she moaned.

“Come lie beside me, and I’ll kiss you,” he offered.

“I’m not getting in bed with you, Bobby Jordan!” she whispered.

“I’m not going to have sex with you,” he said, smiling. “I’m just going to kiss you.”

“You want to touch me too,” she argued.

“It’s all part of kissing. Last time I touched your butt.”

That was true. She remembered that part. She remembered his lump pressing against where she’d liked to rub, too. But her memory of that kiss ... those two kisses ... pulled at her.

“Only a little,” she said.

“Okay, only a little,” he agreed.

She crawled gingerly onto the bed, and lay stiffly beside him. He twisted until he was on his side, and laid his hand on her hip. She clamped her elbow down, as if to keep his hand there. He leaned forward to kiss her.

This was, however, a different kind of kiss. It was gentle, a fairly quick pressing of loose lips against hers. She opened her lips, to receive his tongue, but he didn’t do that. Instead, he pulled back just enough to let him slide his lips sideways a fraction, and he kissed her again. He kept doing that, giving her just quick, warm kisses, moving all around her lips, until she felt like she was going to scream if he didn’t kiss her!

The pressure on his hand disappeared as she lifted the hand on that arm to put behind his head ... to pull him to her lips.

He gave her what she wanted, and she went limp as he ravaged her mouth. The feelings were so intense that she didn’t even feel it, at first, when his hand slid up her side, to mold her left breast, and feel for the nipple on that breast, through her cotton nightgown. She wore only panties under her nightgown, and the cotton of her sleeping garment was old and thin.

She felt like she was floating again, and then, a niggling little spark of electricity wormed its way into her brain, and she realized he was squeezing her nipple. It added so much to the kiss that she felt like she could cum without even touching herself. Almost.

She didn’t need her hand on his head any more. He had rolled toward her, and she realized she was mostly on her back. Her hand went to the front of her nightgown, and she pressed hard, between her legs as the kiss went on and on.

She bucked and jerked spasmodically, as she came, feeling things with her lips, at her nipple, and between her legs, all at the same time. It was so sweet that she thought she might drift away, never to return.

Her mind came back, to find he had pulled back from her, and was just staring at her face, a small smile on his lips. His hand was just smoothing over her breast now, rubbing gently, pushing the hard flesh to one side, and then down, like he was rubbing on oil or something.

“That was fantastic,” she sighed.

“It’s really serious, though,” he said, warning plain in his voice. “It makes me want to do other things ... things we shouldn’t ever do.”

“Not me,” she said.

“Not yet,” he countered. “You never wanted to kiss me like that either, until you saw me kiss Mamma.”

“Have you touched her ... like you touched me?” she asked.

“No.”

“How many times have you kissed her?” asked Mary.

“Once.”

“Just once!?”

“Well, two times, but at the same time ... when you were there. I kissed her once before you saw us.”

“But not since then?”

“She knows better. That’s what I’m trying to teach you.”

“I love kissing you,” she admitted. “It makes me feel so special.”

“I love kissing you too,” said her brother. “It makes me want to have sex with you, though.”

She was shocked, and sat up.

“I would never do that!” she gasped.

“I’m just telling you how it makes me feel,” said Bobby, lying back harmlessly. “You need to understand that’s how boys feel. Kissing is fun, but it leads to wanting other things.”

She was quite aware of that, except that it somehow seemed safer with Bobby, than thinking about doing any of those things with another boy.

“So ... you’ve done other things?” asked his sister, suddenly interested.

“I told you, I’m not going to talk about that,” he said.

“But you’ve done them,” she insisted.

“Yes,” he said. “Now, go to bed!”

She got up, and started out. Then she came back.

“Good night,” she said, leaning down to kiss him again.

This time, when his hands molded themselves to her breasts, she didn’t jerk back.

She just licked his tongue with her own.


Months passed. Sherry still needed him, though not quite as often. Being pregnant wasn’t as much fun as she had thought it would be. Her stomach was upset a lot, and her ankles swelled. Still, there was something about sliding her hands over her swelling belly, and knowing that a baby was in there, waiting to grow enough to come out, where she could hold it in her arms ... that made up for the tedious parts of it.

She spent hours trying to decide how she felt about Bobby, and how she felt about Sam, and what her future should be, with both of them. Sam, as it turned out, got more interested in her as her belly got larger, rather than less. He still complained that it was too soon for children, but when he came home, he stayed a day or two longer, and he had more energy for making love. He was particularly happy when all he had to do was lie there, while she rode him, using muscles she’d trained with Bobby, to get her husband to the point where he couldn’t hold it in any longer.


Mary came to kiss him good night every night now ... always after everyone else had gone to bed. She no longer waited to be told to lie down. Based on his warnings, she expected him to touch her other places, but his hands stayed on her breasts, outside her nightgown. She knew he was aware that she was touching herself as they kissed, and that she was having orgasms but, despite his warnings, he didn’t try to do anything else to her.

She was both happy and unhappy about that, in ways that were very complicated. She went on more dates, and kissed more boys, but none of them made her feel like Bobby did. It was fun, but it wasn’t as exciting. Not like Bobby. She didn’t want to have orgasms with the boys she dated. That part of Bobby’s warning had sunk in.

But she did want to have them while she kissed Bobby.


Bobby got a call from another potential customer. Again, she was referred to him by Martha. Her name was Prudence Harris and, of course, Bobby knew a little about her. He knew she was a widow, though he didn’t know anything about how she became one. She had a daughter that was Bev’s age, and in the same class as Bev in school. Prudence worked at the bank, as a teller and, as far as Bobby could remember, didn’t ever attend the town celebrations, or ice cream socials.

He repaired her broken gate, and painted the rest of the pickets in the fence. A door in the back of the house had rotted at the bottom and needed to be replaced, but they were waiting until warmer temperatures arrived, since the open doorway would let expensive heat out until then.

She seemed like a nice woman, and they talked a little, as she gave him a piece of cake one time. He rarely saw her daughter, Constance, who seemed to stay in her room at all times he was there. He could tell Prudence was lonely, even though she saw, and talked to people every day at the bank. She made no overtures toward him the two times he’d been to her house, and he behaved like the gentleman everyone in town was sure he was.

She had lots of ideas for sprucing up the house, but was thinking about them, prioritizing them. She said she’d call him when she was firm about what she wanted.


It was coming on Spring, and Mary finally went out with a boy who was more interesting than the others. He touched her breasts, outside her shirt, and he kissed with his tongue, like Bobby. He still didn’t make her tingle, and want to rub, like Bobby always did, but he was interesting, and she agreed to keep going out with him.

On their fourth date, his hands wandered from her chest to her belly, plainly on their way somewhere lower. She stopped him, but continued to kiss him. He relented, and went back to her breasts, which suited her just fine.

That night, though, when she climbed onto the bed to kiss her brother good night, and she told him about it, her kisses were a little more urgent. Bobby’s hand slid down her back, during one long kiss, and then slid up the back of her naked leg, dragging her nightgown up. His hand, on the outside of her panties, didn’t feel that much different to her than it did outside her nightgown. She reached down to rub, and tensed as Bobby’s hand slid around, up, over her hip. She tried to say “No!” into his mouth, but he was sucking her tongue, and all she got out was a strangled “Mpfh!”

But then his hand came on top of hers, and pressed. He was ... helping her rub ... but not rubbing himself. This wasn’t so scary, and, with his hand on top of hers, one of his fingers occasionally slipping between hers, to touch her panties, her orgasm was, if anything, more intense.

As she relaxed from her orgasm, still kissing him, and his hand slid up her naked belly, to her naked breast, it just seemed natural, to her, somehow. Skin on skin felt so much better! When he found her nipple, and rolled it between his thumb and fingers, she moaned, and sucked his tongue.

“These are all things he’ll want to do,” he whispered, when they stopped to catch their breath.

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