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

The Making Of A Gigolo (3) - Sherry Winston

Copyright© 2007 by Lubrican

Chapter 1

Erotica Sex Story: Chapter 1 - 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  

October, 1969

Sherry felt butterflies in her stomach when she opened the door and looked at the young man standing there. He had the strap of a bag of tools over his shoulder, and the morning sun was bright behind him, so she couldn’t see his face. His general form, though, was intensified by the sunlight around him.

He had broad shoulders. The butterflies intensified. She’d always had a weakness for broad shoulders. His waist was narrow, and his legs looked slightly bowlegged, like he rode horses. His shock of hair was wild and unkempt, and the wind ruffled it as she stood there.

“Mrs. Winston?” said his soft, deep voice.

She jerked. She’d been staring at him, and standing there mute. She blushed.

“Yes, of course. Come in ... Bobby ... is it?”

She blushed harder. Of course he was Bobby. Everyone in town knew him. Everyone in town knew everyone else in town.

“Yes, Ma’am,” he said, no trace of laughter in his voice. “Your radiator is knocking?”

Sherry got a grip on herself, and pushed away the thoughts she’d been having for the last week, in anticipation of this moment. She had admitted to herself long ago that she’d married Sam only because he had asked her. She’d been thin and boyish at seventeen, and quite sure that no man would ever take an interest in her as a woman. Sam’s interest was both surprising and very welcome, even though he’d tried to move much too quickly for her conservative nature. By their third date he’d been running his hands over her flat breasts, and kissing her in ways that made her head spin. When, as she lost her virginity to him on a blanket under the stars, out in old Mr. Johanson’s pasture, he’d professed his undying love and asked her to marry him, she’d yipped “Yes!“ She now knew that part of that “Yes!“ had been an outlet for the pain of him splitting her maidenhead, and part frantic answer before he could take it back.

Sam’s ardor had cooled somewhat, once they were married. He was, in his own mind, on the fast track toward becoming part owner in Haskins Plumbing Supplies, where he had been employed part time while he was in school. Once married, he went on the road as a salesman, often being gone for three weeks at a time, and returning only for a few days between trips. He covered four states, and was convinced that it was because he was the best in the business.

Sherry, being much closer to the headquarters of the business, knew better. Rupert Haskins couldn’t find the four salesmen he needed to cover all that territory, and with Sam working his ass off, he didn’t need to try all that hard. Vague promises of better times ahead, when Sam would be able to parlay his sales commissions into buying part of the business, kept Sam away from home, building up his company bank account. They got by all right on what money was actually paid to him, but Sherry was beginning to worry. Rupert was driving a brand new Mercury, and living high on the hog. He’d lived the same simple lifestyle as everyone else in town until Sam went to work for him. As the years passed, his lifestyle improved visibly, while Sam and Sherry lived in the same, frugal way.

Even when he was home, Sam didn’t take the kind of interest in her that she thought he should. A man, away from his woman for weeks on end, should be wild with passion when he returned to her. Sam wasn’t, though, and seemed to have very little sex drive at all. Her horror at having to seek release with her fingers while he was gone, turned to terror as she had to do the same thing, sometimes, when he was actually home. She heard stories about salesmen and farmer’s daughters, and things like that, and had a deep seated worry that, some day, Sam just wouldn’t come home anymore at all. Part of that worry was that she hadn’t given him a son yet. Of course that was hard to do when you only tried to make a baby every three weeks or so, and most of those times didn’t happen at a point when she was fertile.

She had no proof that he was unfaithful to her, except for that time when he came home and wouldn’t touch her. He’d gone to visit to the doctor, saying he was feeling under the weather, and didn’t want her to catch whatever it was that was ailing him. He didn’t touch her the whole week he was home, and was taking penicillin for an ailment that he wouldn’t tell her anything about. She’d seen Doctor Grissom a week later, at the butcher’s, and he’d told her it was time for a checkup, even though she’d been to his office only six months before. His examination was much more thorough than past ones, especially between her legs. His smile, when he’d given her a clean bill of health, had been so brilliant that she worried, thinking he’d expected to find something wrong with her, and was very pleased that he had not.

That had been six months ago, and Sam had made love to her only four times since then.

This was the frustrated, lonely, horny young woman who ushered Bobby into her house, and to the radiator that had made horrible noises last winter. She was quite sure it would make the same noises this winter. That, and the fact that she had no idea how to start up the boiler, were her excuses for taking Martha’s advice to let this young man ... brighten her existence.

Bobby surveyed the radiator ... and the woman.

The radiator took only a few seconds to determine what its problem was. He spent the rest of the five minutes that he “looked” at it examining the woman.

She was over thirty in his estimation, but looked closer to being in her mid twenties. She was very short, with slight bulges under her sweater, and slim hips, encased in slacks. She had short, blond hair, cut in a bob, and huge blue eyes that looked nervous. She acted like Martha had acted, the first time he returned to her house after tasting her charms. Her eyes went everywhere in the room, but always returned to him, moving up and down his body, and her hands fluttered, as if she didn’t know what to do with them. She went from letting them hang, to folding her arms, to putting them on her hips. If she’d had pockets in the slacks, he suspected she would have put them in those pockets.

Her physical appearance reminded him of his sister, Susie, who had just turned fourteen, and looked boyish, to her immense chagrin. Bobby had gone to some lengths to “accidentally” see Susie naked, at which time he had whistled and grinned, telling her she was going to be a heart-breaker. Her beaming smile had made him feel good, because he knew he’d made her feel good. She’d been much less modest around him ever since.

In truth, he found his sister’s spare charms exciting. Perhaps it was the promise of maturity to come, or the smooth clean lines of her youthful figure. Whatever it was, he’d had to make a special visit to Martha’s house to work off the passion that had stiffened him. This woman affected him in a similar way, and he felt his cock move in his pants.

“Can you fix it?” asked Sherry, trying to concentrate on the matter at hand. She was embarrassed that just being in the same room with this man made her want to masturbate.

“It’s out of level,” said Bobby. “See here? The floor has settled, and this end of the radiator is lower than the other end. That traps air there, and then steam flows in and makes the water on both sides boil. It’s the boiling that makes the noise.”

“We can’t raise the whole floor!” gasped Sherry.

“No, but we can put a shim under this end of the radiator, and level it back out.” He made it sound so simple.

“It’s embarrassing ... having to call you here ... when my husband sells plumbing things,” she said, trying to remind herself that she was married, and shouldn’t have listened to Martha at all.

“He’s busy, and I have the time,” said Bobby.

Yes. That was the problem. Sam was busy ... too busy to take care of her ... and this handsome young man had the time. She felt a tightness between her legs, and bent forward slightly. She hadn’t felt like this since the second time she’d had sex. Her face flamed red.

“I ... I feel a little tired,” she said, her voice breathy. “Do you need me to help you?”

“No, I can do this by myself.”

“I think I’ll just go lie down for a little bit then,” she said, keeping her hands away from her loins.

“That’s fine,” he said. “I’ll try not to make too much noise.”

Sherry all but ran to her bedroom, taking time to push the door closed, and then flopped on her bed. She undid the hook on her slacks, and groaned as she slid her hand into the front of them, going beneath her panties, to hook a finger into her sex. She closed her eyes, which was why she didn’t see the door, on its sagging hinges, slowly swing open a foot.

Bobby couldn’t help but hear the moans coming from the bedroom. He had seen in Sherry some of the signs he had learned to look for in Martha and Tilly, but had ignored them. He’d been very lucky with both of his lovers, and he knew that. He went to the bedroom door, but only to make sure she wasn’t sick, and didn’t need help. Seeing her hand moving furiously in her pants convinced him that she was all right, and he moved back, to give her privacy. He had no idea what would happen, but thought he should just do what he had been called here to do. Then he would see if anything else needed ... doing.


He was lucky. The pipe that came from under the floor, in the crawlspace under the house, had some flex in it, so he was able to make and drive home a shim, and didn’t have to disassemble the connection. He was actually finished making the repair before Sherry was finished taking the insane edge off her sudden sexual need. She rubbed herself through three orgasms, remembering that black hair, and those gorgeous blue eyes, above those strong, wide shoulders, before she felt relaxed enough to take her hand out of her slacks and lie there. She wasn’t sleepy, though. Sexual release seemed to give her energy, rather than sap it. She lay there long enough to get her breath back, and then bounded up off the bed. She found Bobby, sitting on the floor. He had removed the pressure release valve from the end of the radiator and was cleaning it.

“Feeling better?” he asked, his attention on the valve in his hands.

Sherry’s breath caught in her chest. Something in his voice made it sound like he knew, somehow, what she’d been doing. She looked at her watch. She realized she’d only been gone for fifteen minutes ... not nearly long enough to have “gotten better”, or taken much of a nap.

“I was just feeling strange,” she said, nervously. “I guess it passed.”

“That’s good,” he said, looking up long enough to smile. “As soon as I take care of this, you’ll be all fixed up.”

“That’s wonderful!” she said, happy to change the subject. “Can you start the boiler for me too?”

“Sure,” he said, looking up again, with that beautiful smile. “Whatever you need.”

Sherry stared into his blue eyes, and felt the urge come back. How could he do this to her? She’d had fleeting moments, when she noticed a man, here or there, and had a little fantasy ... almost always banished immediately, as she had clamped down on her imagination.

He went back to working on the valve, and she watched his fingers work. She realized suddenly what it was that was so troubling about him. She knew that he had lain with Martha ... many times, if Martha’s less than complete confession were true. Looking at him was different than looking at just any old man. This man had made Martha happy ... in bed ... and she couldn’t ignore his sexuality, because she knew he had made Martha happy ... in bed. Her nipples tightened on her small mounds. That hadn’t happened in a long time.

His fingers were long ... longer than hers. She shuddered at the thought of those long fingers probing inside her. She felt faint, suddenly, and went to the couch and plopped down.

“Are you all right?” he asked, concern in his voice.

“I feel so strange,” she said, leaning her head back, as the room seemed to spin. She felt weak, and realized she was panting.

“Do you need to go lie down again?” he asked.

“No,” she sighed. “I just need ... I don’t know what I need,” she said helplessly. She felt like she was in a dream world. Her pussy itched, but she couldn’t touch it. Not with him right there in the room. Somehow she knew that even if she did go back to her room, and shove her hand in her slacks again ... it wouldn’t be enough.

She felt better with her eyes closed. Not looking at him helped. She heard the sound of metal on metal ... him using tools ... those long fingers ... gripping ... twisting ... manipulating...

She felt, rather than saw him rise, and come to stand in front of her. She realized that her knees were a foot apart, slack in her weakness, and closed them, automatically.

“You look pale,” he said softly.

“I’m fine,” she said, knowing she wasn’t. “Can you start the boiler?”

“Whatever you need,” he said.

She wanted to moan. What she needed was those fingers, stroking her, bringing her to a point where she didn’t feel like she was going to waste away into nothingness. She brought a hand up to cover her eyes, so she couldn’t open them and look at him.

She lay there limply for long minutes as she wrestled with her emotions, until she realized he wasn’t in the room any longer. Opening her eyes, she lifted her head. Her knees had fallen apart again, and she closed them, feeling the need still in her. Wasn’t this why she’d called him here? Why was she fighting this so hard? He was obviously willing, according to Martha’s veiled admissions. Another part of her mind railed at her, calling her a slut, and reminding her that only one penis had ever entered her body ... that of her husband. The warring factions created energy, and she stood.

She found him in the boiler room, bent over, lighting the burner. His buttocks were tightly encased in the jeans he was wearing. She found herself comparing him to Sam, who was about the same height, but much heavier, with much more flesh on his body, from eating in restaurants every day. Sam was portly ... almost fat. She suddenly wondered what Bobby’s penis looked like. Sam’s was usually a short pile of flesh with a shiny head, that stuck up out of his nest of pubic hair. When it was hard it stuck up further, but she’d never really had time to examine it. When Sam had taken her virginity, it had been dark. Since then, whenever they made love, he was quick and efficient about it, climbing on top of her as soon as he was ready, and, occasionally, lasting long enough that she could reach for the orgasm she’d learned she could have by using her fingers. She’d never had an orgasm with him for the first two years but, once she’d learned how ... without him ... she was able to move and rub against him in such a way that, if he went long enough, she could squeeze one out before he sighed and collapsed on top of her. By the time she got to see his penis again, it had returned to its normal, short, shiny appearance. She’d never seen another one.

He leaned back, turned a knob, and there was a whoosh and bright light as the burner caught. He closed the door, and walked past her as if she weren’t there, going out the back door. She followed him, and saw him looking into the oil tank.

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