The Making of a Gigolo (3) - Sherry Winston

by Lubrican

Chapters : 1 | 2 | 3 | 4

Chapter Four

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 Flo's age, and in the same class as Flo 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.

"I won't let him," she sighed.

"You wouldn't let me either ... when we started," he reminded her.

"Why do you always do that to me?" she whined. "I'm having such a good time, and then you go and ruin it for me."

"I know what men want," he said. "I worry about you."

"If you're so worried about me, why is your hand inside my nightgown?" She looked steadily at him.

"If I had my way, you wouldn't be wearing your nightgown," he said.

The thought of lying there with him, like this ... naked ... caused an upwelling of something in her that was frightening, and she disengaged, and got up.

"Sometimes I don't like you very much," she said softly.

"I always love you, Mary," he said, folding his hands behind his head.

Her eyes glanced down at his underwear. They were tented with what she now loved to rub against, while they kissed.

She had to rub again, when she got to bed.

"What shall I name our baby?" asked Sherry. She was lying on her back, naked, legs spread. Bobby had just finished rubbing oil all over her belly, and was preparing to lick her to orgasm. She found it too uncomfortable to have him in her now. Her due date was only a week away, in August. Sam had actually said he'd come home and stay for two whole weeks when it was time for her to have the baby.

"That's up to you," said Bobby, sliding his hands under her butt.

"Oooooh, I just love that," she moaned, as he sucked at her vulva. They had grown, for some reason, as her pregnancy progressed, becoming plumper, darker, thicker.

When she had cum, and he was just licking her with the flat of his tongue, lapping up her juices, she sighed in contentment.

"I could name it something crazy, like Frank Zappa did. Moon Unit! Can you believe that?"

"You and Sam should decide together," said Bobby.

"He is getting a little better," said Sherry. "He's been more attentive to me since I got pregnant."

"Pregnant women are the most beautiful women in the world," said Bobby, getting to his knees.

Sherry looked at her swollen abdomen doubtfully.

"I don't know about that," she said. "I'll be glad to be able to see my toes again."

Bobby picked up one of her feet, and held it where she could see her toes. He sucked on the big one, and she squealed, trying to jerk it out of his hands. The baby moved, jerking inside her, and she winced. She saw a heel slide across her belly, as the baby inside her turned.

Bobby leaned forward and kissed her belly.

"Calm down, little one," he said to her stomach. "You'll be out soon enough."

"I'm so happy, Bobby," said Sherry, tears coming into her eyes. "You've given me so much."

"I'm glad you're happy," he said, looking up. "You deserve to be happy."

"Lie down," she said, struggling to get up. She had to roll sideways, and then onto her hands and knees to get off the bed. "I want to do something special for you."

He lay down and watched; only mildly surprised as she prepared to suck him. When she stayed on, as he sprayed his seed into her mouth, he was surprised, but accepted her gift, as he gave her his own. The look on her face, when she stood back up, made him feel almost as good.

"I can't believe I waited so long to do that," she said, wiping a dribble of cum from the corner of her mouth, where it had leaked. "You taste good!"

"There's always time for that," he said.

Bobby knew that another boundary had been crossed, when, as he slid his hand up the back of Mary's leg, he found she wasn't wearing panties. She didn't say anything to him, but she left her hand on his cheek as they kissed, and rolled back, to give him room to move to her breasts. He had been stroking her naked breasts for several weeks, now.

It was probably because Sherry had gone into labor, and had their baby, that he did something he might not, otherwise, have done. Sam was home, and Sherry was in no condition to relieve his sexual urges anyway. Jake still let him see Tilly, but she called only infrequently. They still wanted to wait a little longer before she got pregnant again. Martha and he didn't have that kind of relationship any more, now that Arthur had stayed clean and sober for a whole year. If Bobby had a best male friend, it was Arthur.

At any rate, when his hand slid down, across her flat belly, and his fingertips ran onto a soft patch of pubic hair ... she didn't stop him.

He was good at this ... very good, by now ... having learned with three women, how to get them off. True, she did jerk, as his fingers slid onto her slick vulva, but the energy of that jerk was channeled into her upper leg, which bent at the knee and sprang upwards, to give his hand more room.

Her lips slid off of his, and into his neck, as he probed, gently, feeling the barrier that proved she had never put anything inside her. This was something he had no experience with, and his tentative exploration caused her to tense up and wince.

"Should I stop?" he asked.

"Shhhhh," she said into his neck, her breath hot.

He settled for working on her clit, and she went off like a bomb. Her leg slammed closed and she squealed into his neck as she came hard.

She kept her face buried in his neck, even when he removed his hand, and stroked her back on the outside of her nightgown.

"I need your help," he whispered.

Her cheeks were still stained with the red of her blushing, when she finally pulled it out of his neck.

"Would you touch me?" he asked.

Every time she had gotten up to leave ... to go to her bedroom ... Mary had looked, however briefly at the proof that her brother found her sexually desirable. She had wondered, fleetingly, what it might feel like to her touch, but had always chased that errant thought away.

"I shouldn't," she whispered.

"We shouldn't be doing any of the things we do," he said, maddeningly.

"We always seem to do a little more," she said, uncertainly. "All I ever wanted was a kiss."

"I'll stop touching you, if you want me to," he said.

She frowned. "I don't want you to stop! That's the problem."

"I tried to tell you all this," he said.

"I know that!" she hissed. "That's part of why I feel so ... “ She threw up her hands. "I don't know how I feel!"

"It's okay," he said. "I can do it myself, after you leave."

"Do you do that a lot ... after I leave?" she asked, instantly curious.

"Every time," he said.

"Really? Because of me?"

"What have I been trying to tell you for most of a year?" he asked patiently.

She stood there for a long time, staring at the lump in his underwear.

"Show it to me," she said, finally, her voice tentative.

Without ceremony, he pushed his briefs down, and his stiff prick slapped against his stomach.

Her breath caught in her throat.

"It's ... huge!" she gasped.

"I don't think so," he said. "Looks like it always has, since I grew hair."

"How can that possibly go inside a woman?" she asked.

"It does," he said, not thinking.

"I knew it!" she pounced, like a cat. "You have done it!"

"Millions of men have done it," he said, carelessly. "That's how babies are made, and there have always been babies. It has to fit. That's all I meant."

"What will happen if I touch it?" asked Mary, staring at the tube of flesh.

"I think you know what will happen," said her brother.

Looking at this amazing thing was making her pussy hot again. She had already stayed longer than she usually did. The house was quiet, though.

"How long will it take?" she asked. "If I touch it, I mean."

"Not long," he said, “especially if you kiss me while you're doing it. You're a very good kisser, Mary."

She felt inordinately proud that he considered her to be a good kisser. As far as she was concerned, he was the best possible kisser ever born.

"I don't know how," she said.

"I'll teach you."

Mary eased into her room quietly. It certainly wouldn’t do for Flo to wake up now. She held her hand out, away from her body. It was wet with what had come spurting, impossibly high into the air, from that beautiful, soft-yet-hard thing she had loved stroking. She couldn't go to the bathroom and wash her hands. The pipes knocked in there. And, if she went to the kitchen, someone might hear that and get up to investigate.

She was so horny she could hardly stand it. She knew she needed to rub, but the hand she rubbed with was all wet with his stuff. Her body felt hot, and she shrugged her way out of her nightgown. She was careful not to get any of his stuff on it. Mamma might notice, when she did the wash. Unless it was either her or Flo's turn to do the wash. She couldn't remember right now. Better not to take chances.

She lay down on top of her sheets and spread her legs, so the cool air could reach her steamy pussy. Her mind went back to watching her hand, on his stalk, sliding up and down, the slick, bulbous head being covered, and then uncovered, over and over again, until a stream of thick white shot upwards. She was so intent on remembering every detail, that she didn't realize she had relaxed her hand, until she felt cool wet on her belly, where it had fallen. Now his stuff was on her body. What would it look like when it dried? Would anyone be able to tell it was there? Was it really any different than when her hand was wet with her own juices?

Her hand drifted down. She got some of his stuff in her hair. She liked the way he rubbed her, with three fingers. She usually only used one, but his way felt better. Soon she was mixing his thick white residue with her own clear emissions, as she rubbed her pussy lips, and strummed her clitty to orgasm.

Sherry's story went on, but the time it takes to cover includes other women's stories as well. A few of the details will be related, in later stories in this series but, suffice it to say that, Sherry and Sam stayed together. Unknown to either of them, Sam's fetish turned out to be one for pregnant women. Once his wife was pregnant, his interest in other women, out on his sales route, began to wane. Life was a lot easier, not having to sneak around with those women, too, and he found that, by not having affairs, his work went much more quickly, and he could get back home to his pregnant wife. Then, when she wasn’t pregnant any more, he was fascinated with the baby girl she had, named Jessica. That was because he had no idea how to be a parent, which was a big part of his resistance to ending up that way. Now, with the memory of his wife's big, beautiful belly, which he fully intended to make big and beautiful again, and the darling bundle of joy she presented him, he was much more inclined to spend time at home, rather than on the road.

That transition took some months, as he finally figured things out, but the fact is, his life was made much better by the man who his wife cheated with, and who got her pregnant. It was good that he didn't know about that.

As they say ... what you don't know ... probably won't hurt you.

The End

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