The Making of a Gigolo (3) - Sherry Winston

by Lubrican

Chapters : 1 | 2 | 3 | 4

Foreword

This is the third in a series of stories about how Bobby Dalton was transformed, from a normal teenage boy, into a man sought after by many women. His story starts with "The Making of a Gigolo - Tilly Johnson", and there is much information in that first story that will be useful to you in understanding what happens in this story. Please read the stories in order, for your fullest enjoyment. Bob

Chapter One

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.

"The tank's about a third full," he said, coming back toward her, wiping his hands on a rag he took from his pocket.

"I'll call to get it filled," she said, feeling her knees weaken as her eyes slid down to his hips, and then back up to his broad shoulders.

"Need anything else?" he asked, smiling.

"Yes!" her mind shrieked.

"I suppose that's about it," her voice said. It sounded sad, even to her.

"Maybe I should check the other radiators," he suggested.

"Yes!" she blurted.

Everything went well, until they got to her bedroom. As soon as she followed him into it, she knew she was lost. He was in her bedroom. The bed was right there!

"This one is close," he said, examining the metal object. "If it rattles, it should be easy to fix."

"All right," she said weakly.

He turned around.

"You look pale again." There was concern in his eyes.

"I don't feel too good," she moaned.

"You'd better lie down," he cautioned, as he saw her lean to one side. She had to take a staggering step to keep herself upright.

She felt his hands on her elbows, and let herself be steered to the bed, where she sat heavily, and then flopped backwards. Then his hands were on her thighs, just above her knees, as he lifted her lower body, effortlessly, and moved her until she was lying on the bed. She felt him press his palm to her head.

"You feel hot," he commented.

"I'm fine," she moaned.

"Be right back," he said.

She lay there, wondering what was happening to her, and he returned with a wash cloth. It was cool and wet as he applied it to her head. His fingers were gentle. Martha had said he was gentle. He'd been gentle with Martha too ... when he...

Her eyes opened to see his face above hers.

"Better now?" he asked.

Her mouth started saying things, and her mind listened to her voice, astonished.

"Martha said that you could make me feel better."

"She did, did she?" said his soft voice.

"She said you'd be gentle."

"Do you want me to be gentle?" he asked.

She stared into those glorious, deep blue eyes.

"Yes," she sighed.

"Then I'll be gentle," he said.

"What are you going to do?" she panted.

"What do you want me to do?" he asked, stroking her forehead with the cool cloth.

"I can't say it," she moaned.

"I see," he said. He dropped the cloth, and stroked her short hair. She pressed her head into his fingers. "When you're overheated like this, sometimes it helps if you loosen your clothing. Would you like me to do that for you?"

"Uh huh," she whispered, with barely enough air to make the sound.

She closed her eyes as his fingers went to the buttons of the sweater. She did feel cooler, as he flipped the halves of the sweater apart, exposing her bra. When his fingers touched the closure of her slacks, she sucked in her belly, instinctively.

"Do you have to do that?" she asked.

"Yes," he said.

She lifted her hips, as he pulled her slacks down.

"You smell good," he said, casually.

She realized that, with his nose where it was, he probably smelled the results of her previous attempt to satisfy her aching pussy, and felt heat suffuse her chest and cheeks. She realized she was lying in front of a strange man in only her underwear, and felt completely naked.

"I shouldn't be doing this," she whispered.

"It's all right," he said.

She flinched, at the feel of the cool cloth, on her upper chest, but then sighed as he swabbed her exposed skin with it. It felt wonderful. It had been cool in the house, but it didn't feel cool now, for some reason. He had just lit the boiler. It hadn't had time to produce heat yet, but this felt so wonderful. She felt him roll her to the side, and his fingers went to the catch of her bra. She wanted to stop him, but only because she was ashamed that she didn't look like a woman.

When she rolled back, she covered her bra, pressing the cups to her spare mounds.

"Let me take that off," he urged.

"I'm so small," she moaned.

"You're beautiful," he said.

Her eyes snapped open and searched for his. In them, she saw not teasing, or derision. Instead she saw that he was telling the truth! He did think she was beautiful.

"How can you say that?" she asked, in wonder.

"It's easy," he said. He tugged, and she let him remove the bra, sliding it out from under her hands. Gently, but with firm pressure, she let him move her hands, slowly, away from her breasts. He picked up the cloth, and she held her breath, watching, as his hand brought it to her left breast.

Her breath whooshed out as he scraped the cloth, which suddenly felt rough, over her nipple, and then dragged in another breath to moan as he did the same thing to her right nipple.

"Beautiful," he sighed. He dropped the cloth, and used his hand, to slide over them again, bending her stiff nipples, until they fell sideways under the pressure of his palm. His fingers traced around them, pulling, but not gripping, as if he were coaxing them out of her breast flesh, trying to get them to get even longer.

"I know what you need," he said, leaning over to kiss her breast mound, right beside the nipple.

"I shouldn't need this," she moaned.

"You do," he said firmly.

"I knoooowww," she whined.

"I can make you feel better," he said, kissing her breast again.

"Like you did Martha?" she panted.

"She told you?" he asked.

"Not in so many words," she gasped, arching her chest against his lips.

He finally captured the nipple he had been kissing all around, and sucked gently. She spasmed instantly. Sam never did this ... never teased her ... never made her want to scream. Her hand flew to her panty-covered mound. She had just pressed there, when his fingers gripped her wrist firmly, and moved it to her stomach.

"Let me do that," he whispered.

He kissed slowly up her throat, and she arched her neck, giving him more room, as his lips moved up over her jaw, to the corner of her mouth. She closed her eyes again, feeling his hand, flat on her abdomen, those long fingers sliding inexorably downward, slipping under the waistband of her panties. As his finger slid between her slick labia, his lips moved to hers.

Her mouth and legs opened at the same time. She didn't intend to open her mouth to him. That was something she'd heard of ... kissing open mouthed ... but she'd never done it. Sam didn't kiss her much at all, except when he was leaving, or getting back. As Bobby's impossibly long finger slid into her, touching her where it seemed as if nothing had ever touched her so deeply, her knees came up and she arched her hips up into his hand. His tongue, touching hers, was electric, and an orgasm thundered through her body as she let out an agonized groan into his open mouth. Her body went rigid and, for an instant, only her head and heels were in contact with the bed, as her gyrations snatched her lips away from his, and he switched to kissing her throat again.

Then she was limp again, as she crashed back down on the bed. She groaned with frustration as his finger slid out of her, and his hand left her body. She looked over, about to object, and saw him taking his shirt off his upper body. She stared at rippling muscles, and her breath caught in her throat as he worked at pushing his jeans down, kicking his shoes off, and pulling the legs off his feet. When he stood, her breath stayed stuck, and she felt faint, at the bulge that was visible under his jockey shorts.

Unceremoniously he pushed them down, to expose himself to her. He was ready.

She gaped. Never in her wildest imagination could she have envisioned something like what jutted from his loins. It was huge! It had to be six inches long, and as thick as three of her fingers pressed together. She felt another spasm in her loins, at the thought of this thing being forced inside her.

"You can't!" she gasped, knowing this thing would split her apart.

He stopped. His hand came to the thing she was staring at, and stroked it. What she had thought was deformed, took on the look of Sam's, as the shiny head was exposed. Even that looked bigger than Sam's, what little she had seen of it.

"I can use my hand, if that's what you want," he said, his voice breathy.

"It would never fit!" she whined.

"Oh, I assure you, it would fit perfectly," he said. "It always has."

"How many ..." she started. "Were there others? Besides Martha?" she gasped.

"Yes," he said, not wanting, for some reason, to tell her there was only one other than Martha.

"I'm afraid," she moaned.

"It's all right," he said. "I'd never hurt you. I only want what you want."

She watched as he stroked. She saw a drip of something clear, forming on the tip.

"Would you like to do this for me?" he asked.

"Could I?" She voiced the question, but it was more to herself, than to him.

"Of course," he said, not knowing she was talking to herself. He stepped within reach.

She reached, tentatively, and he took his hand away. Her first impression was of heat, and then the velvety feel of it. She realized she had never touched Sam's. It had touched her, but she had never touched it. She was instantly amazed at the conflicting sensations of soft and hard, all at once.

"That feels good," he sighed. "I want to touch you again."

"All right," she said, her mind on the new, exciting thing in her hand.

He pulled away from her, and she looked at him, confused, until she realized he was going to take her panties off.

"I feel so shy," she blurted.

"You look so delicious," he said, smiling at her.

She lifted her hips for him again, without even thinking about it, but kept her legs tightly closed, as he dragged the panties down to her ankles, and then off her feet. He returned to where she could grip him, and stroked her belly with the flat of his hand. Her legs relaxed almost instantly, and she took him in her hand again.

"Like this?" she asked, stroking up and down lightly.

"You can grip it tighter," he said, letting his fingers play in her blond pubic hair.

"I don't want to hurt it," she sighed.

"I don't think you can hurt it," he said, grinning. The fingers of the hand that wasn't driving her to distraction in her pubic hair went to his balls and hefted them. "You could hurt me here, but not there."

She looked at his balls for the first time. She immediately wondered how she could have missed them. They hung low and full, round and heavy, not at all like Sam's, which always hugged his body tightly, looking like walnuts, in a wrinkled flesh sack. Bobby's looked ... bigger, somehow.

Her legs had relaxed to the point that he could slide his hand between her legs. He didn't go in her, this time, but just rubbed the outside of her sex. One finger searched for the bump she knew would send sparks through her body. Her hips lurched when he found it, and slid slick fingers along it, up and down. Her legs sprang open. She realized she had stopped stroking him, and was just holding him.

"I can't ... do this ... while you're ... doing that," she panted, squeezing the thing in her hand.

He leaned over to kiss her, and that only made it worse.

"You can do it later," he said, finally sliding a finger into her.

He probed deep again, and she whined, as she felt the most delicious pain, deep inside her, where his finger tip was pushing and pressing against something that made her want to scream in joy.

His lips lifted off of hers, and he whispered into her mouth.

"Let me try ... just a little."

She knew what he meant, but she was on the verge of another of those amazing orgasms, and couldn't talk. She'd do anything to keep that feeling happening, and she nodded.

He was up on the bed in a flash, between her thighs. She lifted her head to see that enormous thing, in his hand, the tip pressed into her sex. She felt terror, and took a breath to tell him to stop. That breath whooshed out of her as he slid half of his stalk smoothly into her ... just like that.

It didn't hurt.

She stared with wide eyes as she felt pressure, forcing her apart ... but no pain. None at all. She watched as what was in her slid out, and then back in, going fractionally deeper. Her eyes bugged, as he did it again, going almost all the way in. She let out another tortured groan as, on the third try, he socketed the monster all the way inside her.

That place, deep inside her, that yelped with exquisite pain, sounded off again, but this time, along with that exquisite pain, came a feeling she had never felt in her life.

It was the feeling of completeness ... of rightness ... that the world was finally as it should be. Sherry Winston, for the first time in her life, was full of gloriously hard, warm prick. As his loins pushed even harder, and she felt her clit crushed, Sherry Winston realized, in that split second, that she would need this again and again, for the rest of her life.

Bobby stayed deep and rotated his loins in three complete circles. That was all it took, and Sherry Winston's body exploded in streaks of passionate joy that left her bawling, and laughing at the same time.

She flopped beneath him. She had no more control over her body than a person enduring an epileptic seizure does. Streaks of electricity jolted her and made her thrash, as the orgasm went on and on.

Then he fucked her.

Half an hour later, Sherry's limp hands came up and she gasped, crying, "No more! Please ... no more ... I can't ... breathe!"

"Just a little longer," he panted.

"I can't ... take it!" she whined.

"Almost there," he gasped.

She looked up, as his eyes stared into hers.

"Your eyes ..." he panted. "So beautiful."

Then he stopped, deep inside her. She felt his prick jump in her, and a flood of warmth suffused her belly, as he gave tiny jerks into her. She had never felt anything like that in her life. She felt like he was pumping fire into her belly, and realized that what was happening was the culmination of everything she hadn't known she wanted. She welcomed that warmth as he sagged onto his stiff arms, and his eyelids fluttered with the power of what was happening inside him. She was so centered on the feel of his spend, soaking into her, that she was taken by surprise when he rolled, pulling her with him, to lie, side by side, his prick still firmly planted inside her. He felt even bigger with her legs closed on his penis, but that feeling soon left as he softened. She closed her legs tighter, not wanting his penis to leave her, but sighed as he rolled further, to land on his back.

Now she was on her side, lying against him, with one arm across his chest, which was heaving from the exertion of their lovemaking. She watched his face, as his eyes closed, and realized that this ... what had just happened ... really was lovemaking.

She also realized that it had never happened to her before this day.

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