The Making of a Gigolo (4) - Prudence Harris

by Lubrican

Chapters : 1 | 2 | 3 | 4 | 5 | 6

Chapter Three

The girls split up in the hallway, as each went to the room she shared with another sister. Mary didn't clean up. Instead, she pulled her nightgown up and lay on her bed, her legs spread. Bobby's slippery spunk was all over her pussy lips, and she had two more orgasms as she rubbed it all over her pussy, torturing her clitty. Knowing that that slipperiness was a man's sperm just made it even better, somehow.

As for Beverly, she'd known how to masturbate for a long time too, though she did it infrequently. She was nervous about doing that, because of stories she’d heard. She didn't know if they were true or not, but thought it was better not to take chances. Tonight, though, she needed the release. Carefully, she pressed two fingers against that spot she knew would do it for her, and rubbed in a circle. She held her breath as the feelings flooded her loins, and then sighed, and closed her eyes.

She was very glad she'd spied on them, and demanded to be included.

Very glad.

When Bobby returned to Prudence's house, two days later, to check the fit of the door they'd installed, he was surprised to see Prudence dressed in a skirt and blouse. The skirt was plum colored, and the blouse had lavender flowers on it. Her hair was still up in a bun.

"You look nice today," he said, his eyes taking in the thrust of her breasts, under the blouse. They were larger than he'd thought.

"I wore it to work today," she said. "You'd have thought I came in wearing a necklace of shrunken heads."

"They were surprised?" asked Bobby.

"Aren't you?" she asked. She was well aware that her entire wardrobe had consisted of blacks and grays, except for the white blouses she wore at the bank. It had been that way for as long as she could remember.

"You look good," he said, not answering her question.

"That's not flirting ... is it?" she asked, a tiny smile at the corners of her lips.

"When you're ready for me to flirt with you, just let me know," said Bobby. "Then you'll know what flirting is like."

"I know what flirting is like," she said, folding her arms under her breasts.

Bobby stared, intentionally, at her breasts.

"I love that blouse," he said, his voice almost sighing. He looked up to see Prudence's eyes wide. She was blushing. He grinned. "Is that what you thought it was like?" he asked.

She suddenly felt nervous, and much younger than she was. "Something like that, I suppose," she stammered.

"I've said it before. You're a beautiful woman, Prudence," he said softly.

"All right, that's enough," she said weakly. "It isn't right for you to say things like that."

"Like I said," he smiled. "When you're ready to be flirted with, let me know."

She looked startled, and then thought about what had just happened. He'd offered to be a gentleman, but she'd prodded him. When he'd reacted to her prodding, he'd said things that made her feel distinctly vulnerable, yet, here he was, being a gentleman again. She realized she had missed out on a lot of life, and wasn't yet ready to dive back into that maelstrom of emotion. Just buying new clothes wasn't enough to prepare her for rejoining the adult world she'd shunned for a decade.

"Thank you," she said, without meaning to say it out loud.

"You're very welcome," said Bobby. "How's our door?"

"It's beautiful," she said, feeling calmer immediately.

"No swelling?"

"Not that I can see," she said.

"That means the paint sealed it properly," he said. "We'll give it another coat, and then put the molding back up around the inside. We shouldn't have to do any more adjusting after that."

Constance came in the door they were discussing, with a basket of tomatoes, lettuce and onions.

"Oh!" she said, seeing Bobby. "Hi." She smiled, but didn't show her teeth.

"Hi, yourself," he said. "It's nice to see you again."

Constance blinked, and then smiled enough to show her teeth. She raised one hand to cover her mouth, and ducked her head.

"You seem to make us both feel shy," said Prudence to Bobby.

"I don't mean to," said Bobby.

"We're not used to men paying any attention to us," said the woman.

"I'll try to ignore you, from now on," Bobby said, smiling.

"Now you're teasing," said Prudence.

"How about we tackle that cracked window you showed me the other day," said Bobby, ignoring the women.

"Can I help with that too?" asked Prudence.

"I thought I'd have you give a last coat of paint to the door," said Bobby.

"I could maybe do that," said Constance, timidly.

"Excellent idea!" said Bobby. "Both of you need to change clothes, though."

"Okay!" said both women, in tandem. Both seemed excited, and Bobby just sighed.

Constance, as it turned out, changed into shorts and a white T shirt. The shirt was an old one, and too small, hence her decision to wear it, since she had seen her mother's ruined sweat suit. She didn't think about the fact that the shirt hugged her young breasts and showed them off. When she skipped into the kitchen, where Bobby had been getting the paint ready for her, she was reminded of that, when Bobby's eyes raked up and down her body.

"Oh!" she said, stopping quickly. Her hands came to cover her breasts, when she saw him looking there.

"Sorry," said Bobby, looking away. "It's just natural for a man to look at a pretty girl."

"Why do you say things like that?" she blurted.

"Because it's the truth," he said.

"I'm not pretty," she said. "Not like Beverly."

"Beverly doesn't think she's pretty either," said Bobby, stirring the paint.

"That's silly!" chirped Constance.

"It's also silly for you to think you're not pretty, but that doesn't make any difference to you, now does it?"

"Boys don't look at me, like they look at Beverly," she said.

"That's because you don't go around dressed like that," said Bobby, smiling.

Bobby was showing Constance how to move the brush in long, even strokes when Prudence appeared. She was wearing her sweat suit again.

"I guess these are my work clothes, now," she said, picking at a paint stain.

"Let's get to it," said Bobby. "We need to work from the inside."

She took him to her bedroom, since that's where the cracked window was, but it felt strange to take a man in there. At the same time, the last man who had stepped into that room was Harry, and, somehow, Bobby's presence made Harry's ghost seem less substantial. She was so used to thinking about Harry, in that room, that she was glad to be distracted by another man.

Bobby showed her how to chip away the glazing that held the window in. When the chisel bit into the wood, he reached around her with both hands, to correct the angle of the chisel, and his body pressed against her back gently. The sensations were so disturbing that she missed the chisel completely, with the hammer.

"Calm down," he said, over her shoulder.

"When you touch me, I get all nervous," she whispered.

"It's just touch," he said, moving his hands to her waist.

"It feels wrong," she said, gripping the hammer tightly.

"You're a woman," he said. "I'm a man. But we're also just two human beings and all I'm doing here is teaching you something. You have nothing to fear from me."

"But I haven't been touched by a man in years," she sighed. "It feels so strange. Right now all I can feel is your hands."

Bobby squeezed his fingers gently on her waist.

"It's nothing," he said. "I can stop, if it upsets you."

"I don't understand this," she moaned, staring at the chisel in her hand. "Why would you want to tease me ... flirt with me ... touch me?"

"I like you," he said, his voice soft. "I like to touch people I like."

"But I'm old enough to be your mother," she moaned.

"That doesn't mean anything to me," he said. "I like you."

"What does that mean?" she whispered.

"It only means that I like to be around you," he said. "Now, work on that window."

"I can't," she moaned. "Not with you touching me like that."

"All right, then," he said, stepping to the side, and removing his hands from her waist. "Remember what I showed you. Get the angle right, so you don't get into the wood."

She gave a few tentative taps, and a long stick of withered glazing popped off the edge of the window. He coached her, until she was chipping away industriously. He explained that the little metal triangles she was uncovering were called glazing points, and held the glass in, until the glazing compound was applied. He told her how to pry them out, and reached past her to hold the cracked glass in place, as she finished removing everything. Then he let the glass tilt, until he could grab the larger piece, while she held the smaller one in place.

"Take this to the lumber yard," he said. "Give it to them and tell them you need a new pane, the same size."

"You're not going with me?" Prudence sounded disappointed, somehow.

"You can do this by yourself. I need to check on Constance."

While Prudence was gone, Bobby went and stood, watching the girl painting. He just chatted with her, telling her she was doing a good job, and talking about nothing of any real importance. He had no idea that she was thrilled that he was paying any attention to her. To her, he was an "older male", and it was a real honor, from her perspective, that he would notice her at all. She was aware of his eyes on her, and that thrilled her too. She was suddenly glad she'd worn this old, too-tight shirt. She wasn’t sure any other man had ever looked at her like he looked at her, and it made her quiver inside. It was a good quiver, at least from him. Her mother liked this man ... she could tell ... and that made her like him too.

Prudence returned with the glass, beaming at her victory. It fit perfectly, and Bobby showed her how to use the edge of the chisle blade to tap new glazing points in to hold it in place. Then he rolled a strip of glazing compound between his hands, making a long line, which he pressed into place. Then she did it, until there was a line of lumpy looking putty all the way around the window.

"It doesn't look nice, like the other did," she complained.

"That's because we're not finished, yet," he said. "I have to touch you again," he warned.

She said nothing, and he put the chisel in her hand, and showed her how to angle it and drag it along the line of putty, smoothing it, and removing the excess.

"That's amazing," she said, delighted in how the window looked.

"Now you're a door installer, and a window glazier," he said, putting his hands back on her waist.

"You're touching me again," she said, leaning back, ever so slightly.

"This is nothing," he said.

"It doesn't feel like nothing," she said, her hands hanging at her sides.

"May I tell you the truth?" he asked.

"Why couldn’t you?" she asked back.

"It may make you very uncomfortable," he warned.

"What is it?" she asked.

"I'd much prefer to touch you like this," he said, sliding his hands around and up, to cup her breasts.

"Ohhhhhh," she moaned, her hands jerking to grab his wrists.

"It's just how I feel," he said, squeezing gently. "That's all."

"You shouldn't," she said. "I shouldn't let you."

"You feel very good," he said, rolling his hands up and over the tips of her breasts.

"This is crazy!" she breathed. "You have no right to touch me like this."

"That's true," he said. "I just want to, that's all."

"I should stop you," she moaned, her hands squeezing his wrists.

"You can, if you really want to," he whispered.

"Why are you doing this to meeee?" she whined.

"I told you," he said. "I like you."

"This is for married people," she panted.

"That's old fashioned thinking," he said. "You're an adult, and I'm an adult. What's the harm, if it makes us both feel good?"

"Bobby Dalton, you're a wicked, wicked man," she sighed. Her hands dropped from his wrists, and she leaned harder against him.

"Thank you," he said, his hands moving all over her breasts. "You feel just as delightful as I thought you would."

"You thought about this ... before?" she gasped, leaning her head back. She couldn't remember the last time she'd felt like this.

"I thought about this the first time I ever came over," he said.

"That's horrible!" she scolded, feeling butterflies in her belly.

"Does this feel horrible?" he asked, mauling her breasts.

"No," she whispered.

"Maybe some day I can touch them ... naked," he whispered.

She shuddered, and her hands came back to his wrists.

He dropped his hands to her waist, and she was so relieved that she turned to face him. His face was right there, and he kissed her before she could react. That hadn't happened in a long time either, and it shocked her to her core.

When he pulled back, she stared at him with huge eyes.

"What, exactly, are your intentions, sir?" she gasped.

"Only to make you feel good," he said, staring into her eyes. "Only to do what makes you feel good, and nothing more."

"You don't intend to court me?" she asked.

"No," he said. "As you pointed out, there is a significant age difference between us. People wouldn't accept that."

"Yet ... you'd dally with me?" she whispered. "You'd toy with my affections?"

"I'd share something sweet and precious with you," he said. "I want only to please you. You've punished yourself for many years. All I want to do is make up for that a little. It doesn't need to be me. You could find another man."

She shook her head. "No, I'll not be married again. Once was enough. It is too painful."

"I'm sure, in this day and age, there are many men who would be happy to bed you," he said.

She pulled back. "Is that your intention?" Her voice was an octave too high.

"Only if it pleases you," he said.

"You're a very strange and disturbing man, Bobby Dalton," she sighed.

"Think about it," he said, releasing her, and stepping back. "I'm sorry if I shocked you, but I felt that the truth was best."

"Shocked me is an understatement!" she gushed. "I had no idea you harbored such feelings for me!"

"You haven't looked in a mirror, then," he said. "I told you any man would be proud to be in your company, and I meant it."

"I believe you've showed me what you meant by flirting," she said weakly. Her stomach was in turmoil. "I think you should go, now."

"Call me, if you need anything," he said.

Bobby was reading ... and waiting. Mary and Bev must have been talking, because, for two nights, they had come in, given him long, lingering good night kisses, and then skipped back out to their rooms. Bobby could understand why they did that. The feel of his naked prick against Mary's pussy had made him want to fuck her. He'd moved very fast with Prudence, taking a chance that he'd read the signals correctly. He'd figured that, once she had gotten a grip on her guilt, she'd have the same urges as any woman. Her change of clothing signaled that she was coping, so he'd gone ahead to explore new territory. He hadn't seen Tilly in almost a month, and Sherry didn't seem to need him more than once a month. Martha was very friendly, when she saw him in public, but didn't call.

Bobby glanced at the clock on his night stand. It was later than usual. He was beginning to think they weren't coming at all, this night, when the door eased open, and they slipped in together.

Mary shrugged out of her nightgown immediately, and stood, naked, looking at him.

"We want you naked, tonight," she whispered.

Without a word, he skinned down his shorts, and lay back, his penis flaccid and lying at an angle on his thigh.

Beverly looked nervous, and, stood quietly. She had watched, two other nights, as Bobby stroked Mary to orgasm, and then kissed him hungrily when it was her turn. Bobby hadn't even started touching her any place other than on her back and sides. Her kisses were still virginal, if filled with passion. She had then watched, as Mary masturbated him until he spurted, and then licked her hand, where his warm spend covered it.

"You two are playing with fire," he said, as his prick moved, all by itself, getting longer and thicker.

Mary didn't say anything, but walked to the bed and knelt beside it. Bev copied her. Beverly reached for his penis, and grasped it tentatively.

"It does feel warm and soft," she whispered to Mary.

"Wait until it gets hard," whispered Mary back, watching her sister do this for the first time.

"It's getting hard already!" sighed Bev.

"Don't make it squirt," cautioned Mary. "He kisses better when he's hard."

"I'm right here," said Bobby, smiling.

"Do you want to try it, tonight?" asked Mary, looking at Bev.

The younger girl shook her head. "I'll just watch."

Mary stood and climbed up on top of Bobby, making Bev release his prick. She looked down, and reached, to position his organ up, pointing at his belly button. Then she settled her pussy down, spreading her lips with two fingers, and started to rock.

"Ohhhhhhh, I love this," she moaned. She leaned down to kiss him gently. "Try not to squirt. I think Bev wants to try to make you squirt later."

Bobby looked at Bev, who had gone around the bed, and was standing, watching the juncture of her brother and sister.

Mary rocked, picking up speed, and lifted panting lips from his.

"Suck them," she moaned, arching her back and suspending her breasts over his mouth.

He did, and she shuddered and whined, as she came, grinding her clitty on his prick hard. She looked down at Bobby. "I love this, and I love you," she moaned.

"I love you too," he said softly.

"I want to go again," she sighed, sitting up. "But it's Bev's turn."

Mary crawled off of him, and knelt on the floor, as Bev crawled on the bed and lay down beside Bobby. Her hand went to his prick.

"It's wet!" she whispered.

"That's from Mary," said Bobby. "When you get excited, don't you get wet?"

"I'm wet right now," she sighed, reaching her lips to kiss him.

Bobby kissed her hard, and slid his hand up her leg, under her nightgown. He was surprised to find she wasn't wearing panties, and he squeezed her naked butt cheeks.

"That feels good," she sighed, into his mouth. Her hand jerked on his prick, and Mary's hands came to steady them. Mary instructed her on how hard and how fast to go.

"Do you want to cum?" asked Bobby, after a hot kiss.

"I'm scared," whined Beverly.

"It's just an orgasm," he said.

"I'm still scared," she moaned.

"Just kiss me," he said.

She did, and, without warning, he moved his hand to her front, and dipped between her legs. She was wet, and his finger slid effortlessly between her puffy vulva. She jerked, but only kissed him harder.

He probed, gently. He didn't know why, but there was no barrier in her, like there was in Mary. She moaned into his mouth as he slid into her up to his first knuckle. He pulled away to let her breathe.

"Oh shit!" she gasped, as he wiggled his finger in her.

"You mustn't let any other boy do this," he whispered. "Promise me!"

"I won't!" she moaned. "Ohhhh, Bobby, it feels so goooood."

She'd stopped stroking him, and even Mary's hand couldn't get her going again.

He slid deeper, and she jerked again, lifting her upper leg. Her hips made a movement toward him.

"Ohhhhhh," she gasped. Her eyes opened wide. "I feel so full! It's going to happen, Bobby!"

He started sliding in and out of her slippery channel, mauling her clitty and she flopped to her back, abandoning his penis. Mary immediately grabbed it and stroked. She peered at Bobby's finger, disappearing inside Bev's pussy and then appearing again.

"Ohhhh shit!" groaned Bev, arching her hips up.

She was tight, but seemed to be able to tolerate his finger, so he pushed it all the way in. He felt the little knot at the end, and rimmed the tight opening with his fingertip. Bev flopped, and started to make noise, so he rolled half on top of her and sealed his lips to hers. She gave a gut-wrenching groan into his mouth, and her tongue lashed against his, and then she went limp. Easing his finger out of her, he petted her pussy gently, still kissing her, and then took his hand and lips away at the same time. She lay there panting.

He looked down at Mary, whose brow was furrowed as she worked on his penis.

"You like the taste," he said.

She looked at him, and he smiled at her.

"I'm about to cum," he announced. "Just put your mouth over it."

"Can I?" she whispered.

"Sure," he said.

Mary leaned over, her mouth open wide, as her hand sped up.

"Now!" he grunted.

She lowered her head to seal her lips around the tip, and he felt the spurts. She jerked in surprise, and he heard a convulsive swallow. Two more streaks of pleasure jolted through his prick and she pulled back, her mouth full, dribbles of spunk leaking from the corners of her mouth. Her hand continued to milk him, while the other came up to wipe at her mouth. She swallowed again.

"So much!" she gasped. "I didn't realize there was so much!"

"You make me cum a lot," he sighed.

Beverly rolled half on top of him and kissed him urgently again. When she was done, she pulled back just enough to look into his eyes.

"Thank you," she gushed. "That was the neatest thing that ever happened to me!"

"We'll do it again, sometime," he said, smiling.

"We sure will!" she sighed, and kissed him again.

Looking at her, he was reminded of Constance.

"Hey, I want you to do me a favor," he said to Bev.

"Anything," she sighed.

"There's a girl I met. I'm doing some work for her mother. She's in your class."

"Who?" asked Bev.

"Constance Harris," he said.

Bev nodded. "I know her. She seems kind of stuck up."

"She's terribly shy," said Bobby. "But she seems like a nice kid. I'd like you to be friendly to her."

"You'll keep doing this with me?" she asked.

"I'll keep doing this even if you don't do it," he said, smiling. "This is fun for me too, you know."

"Okay," said Bev. "I'll see what I can do."

Neither girl seemed to want to leave, but it was late, so Bobby chased them out.

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