The Making Of A Gigolo 5 Jill TrimbleChapter 5
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Jill worked eight to four at the Wagon Wheel Cafe. She was the only waitress on duty between the hours of eight in the morning and about eleven-thirty. Another woman came in to help with the lunch rush, and stayed after Jill left, at four.
What ruined her Wednesday happened at ten-thirty, when Mark, her ex-husband, sashayed into the diner with Nancy Vickers on his arm. Jill hadn’t seen Nancy since that night in the alley, when Nancy’s pale breasts, and Mark’s face pressed against them, had started their divorce. That had been four months ago. It wasn’t that Mark brought Nancy in, that ruined her day.
It was that Nancy was obviously at least six months pregnant.
Jill had wanted to have kids immediately when she married Mark Trimble, but he had not. He consistently used rubbers when they had sex, no matter what she did. It was suddenly pretty clear to Jill that, when she’d seen them necking in the alley, Nancy was already pregnant with his baby.
Mark stopped at the counter, his arm around Nancy, and called out to Sal, the owner and cook at the Wagon Wheel.
“Isn’t there some other waitress that could wait on us?” he yelled. He knew quite well that Jill was the only waitress in the place. There were only four other customers in the the place.
“Just because she divorced you don’t mean she’s not a good waitress,” said Sal, taking up Jill’s cause.
“I’m just afraid she’ll do something to the food. Nancy here is knocked up with my baby, and I don’t want nothing to happen to it. I been wanting a baby for a long time. That bitch you hired just couldn’t give me one.”
Jill bit her tongue. She couldn’t believe he’d said it. He’d always been snide, and mean, both to her and to others. His own friends, in High School hadn’t even been immune from his cruel taunts. He’d been a bully, though, back then, she had thought of him as being strong and commanding. What she saw now was exactly the same thing, and she recognized it for what it was.
“You want to eat or not?” asked Sal. “Doesn’t make any difference to me. Jill’s my waitress.”
“Well, that’s good, ‘cause she needs a job. There ain’t no way in hell no man will touch a slut like her,” said Mark cruelly. “She’ll never get no man to knock her up, like sweet little Nancy here.”
“You know what, Mark?” said Sal, stepping to the counter. “You see that sign on the wall? Right over there?” He pointed. The sign, in big block lettering, said, “We reserve the right to refuse service to anyone”. “I don’t think you came here to eat, so get out.”
“Fuck you, Sal,” said Mark, swaggering.
“But I’m hungry, baby,” complained Nancy.
“Shut up,” he said casually. “You’re always hungry, or always pissing. At least you’re not diseased, like my bitch ex-wife!” He turned around. The other four customers, all men, were staring at him. “That’s right, men!” he yelled. “Spread the word. That bitch gave me the clap. That’s why I threw her out. I wouldn’t even eat here, if I were you!”
Sal, in a rage, almost caught him, before he dragged Nancy back out the door.
“And don’t ever come back!” yelled Sal, at their backs, as they hurried off down the sidewalk.
Sal turned to find Jill standing there with tears in her eyes.
“Don’t listen to him, Jill,” said Sal, who had a bit of a crush on her, but firmly treated her like she was his niece. “He’s a prick.” He turned to his customers, all of whom were regulars. They were already back to eating, or drinking coffee, or reading the newspaper, like usual. He wasn’t worried about them. He was just glad the bastard hadn’t done that during the lunch rush.
She had to finish her shift. There were no spare waitresses to call in, to give her time to get it out of her system. Sal apologized, and, for probably the twentieth time, said he’d try to hire another waitress, so that the two of them he did have would have some options, in situations like this. For the rest of the day Jill Trimble did a lot of thinking, though, and not all of it was very rational.
Then, on Thursday, Bobby Dalton walked into the diner.
“I have your stuff all repaired,” he said, smiling at her.
“I can’t leave now,” she said. “Have a seat and I’ll get you a cinnamon roll and a cup of coffee.”
“Sounds great,” said Bobby.
She got the order and brought it to him. She placed it on the table, bending, just like she always did. Her uniform showed a lot of cleavage. She got better tips when she wore a uniform tailored like that. She saw his eyes go to that cleavage, and then move away.
“I can just give you the key to my house,” she said. “If you don’t mind.”
“That would be fine,” he said. “I’ll just put everything back where I got it from.”
“How much is it?” she asked.
“How much do you have?” He grinned.
She looked in her pocket. There were five ones, and a dozen quarters. She pulled it all out. “Not enough,” she said. “I’ll get my purse, while you’re gone, and have more for you.”
“I’ll take the five ones,” he said.
“Bobby,” she said. “It’s worth more than that.”
“I didn’t have to spend much time doing any actual work. Most of it was letting the glue dry,” he said. “You’re a struggling waitress, and I don’t gouge pretty women, remember?” He grinned.
When he brought her keys back, his smile made her want to wiggle. She’d been attracted to him in the square, the first time she’d seen him. She’d been even more impressed when he fixed her washer.
“That your boyfriend?” asked Sal, after Bobby left.
“Him?” she said. “No, he’s my handyman. You know I don’t have a boyfriend!”
“Treats you a lot better than your ex,” said Sal.
“I’m not getting married again, Sal,” she said darkly. “So don’t get your hopes up.”
“Sure thing,” he said. “You going to pay for his cinnamon roll?”
“Yes,” she said, frostily. While she put enough quarters from her tip money in the till to pay for what Bobby had eaten, she thought about men in general, and Sal, Mark and Bobby, in particular.
She did a lot more thinking the rest of that day.
She called Bobby that night.
Matilda answered the phone, and got her brother, who was playing Scrabble with Mamma, Suzie and Linda.
“Hello?” he said into the phone.
“It’s Jill,” she said.
“Don’t tell me a chair broke,” he said, teasing.
“No,” she said. She sounded strange, like she was upset. “Do you remember all those other things we talked about you fixing?”
“Yeah,” he said.
“Could you come over Saturday morning?”
“Actually, I can’t,” he said. “My sister is getting married Saturday.”
“Oh.” She sounded disappointed ... almost angry.
“Are you okay?” he asked.
“I’m fine,” she said, no emotion in her voice. “How about the Saturday after that? I want to do this on a day I don’t have to go to work.”
“I can come that Saturday,” said Bobby. “What are you going to want me to do?”
“I don’t know yet. We can discuss that when you get here.”
“All right, I’ll see you then.”
“Okay,” she said. The line went dead.
Wednesday and Thursday nights followed the same new pattern that had started Monday. Both nights Bev stared, as her brother’s thick penis sank inside of Mary’s clasping pussy, and left it messy with white sperm.
Familiarity with the process began to make it seem less traumatic ... less dangerous looking. Bev lost her fear of that penis, and began riding it again, paying particular attention when, as she rocked forward, the big knob pressed into her own pussy mouth, and stretched it a little. Then she’d push back, and let that knob scrape her clitty. She was sure she could do that for an hour, if they’d let her. But she almost always went first, now, so that when she was done, and Bobby was still hard as stone, he could fuck Mary almost senseless, before spurting in her. When Bev went too long, though, it was no real problem. All Bobby had to do was pull her down and suck a tender, sensitive nipple, and she invariably went off like the fireworks at the 4th of July celebration, so recently seen.
On Friday night, though, the night before the wedding ... only Bev showed up.
“She can’t come,” whispered Bev. “Mamma is keeping her up for last minute plans. Flo is in there with them too.” Flo, who Mary had lived with all her life, was going to be Mary’s Maiden of Honor.
“It’s okay,” said Bobby. “You can go as long as you like, tonight.”
“Goody,” she whispered, climbing on him for a long kiss.
She did go for an hour that time, cumming four times. She went so long that he couldn’t cum. She sucked him, then, and jacked on him. When he said he was about to spurt, though, she stood up and lowered her pussy, holding his prick up so that it would spurt on her pussy lips. That was as close as she could bring herself to doing what Mary had done. When she felt his spunk hitting her, she lowered her pussy lips against him, to see what it felt like for that warm, gooey mess to be right there, where her pussy lips hugged it.
“Careful,” he panted, as his prick spat twice more.
“I’m not putting it in me,” she gasped, feeling his warmth surge up into her pussy channel, where her lips sealed against him. “Besides,” she moaned, loving that feel, “you squirted in Mary lots.”
“She’s getting married tomorrow,” he hissed. “If I got her pregnant, Fred will just think it’s his. You shouldn’t get that inside you!”
Her hips shot up in the air, as her legs straightened and she stood, looking down at her pussy lips, which were dripping long drops of white sperm back down on him. She hadn’t thought of that at all!
It was a perfect day for a wedding. It was partly cloudy, which meant the sun’s intense heat was held at bay, yet the day was bright with promise. The Oddfellows hall, which had been the least expensive to rent, but was still nice, was filling up with Fred’s family. Prudence was there, in a dress made by Mirriam to fit her pregnant form, and Constance sat with the girls who weren’t in the ceremony. Only Flo and Bev were standing up with Mary. Linda and Suzie were taking care of the gifts, and Matilda and Betty manned the guest book, using their natural charm and cute looks to encourage people to fill out every block in the book.
Bobby was also acting as an usher. They weren’t seating people based on whether they had come to see the bride, or groom, because the groom’s side would have made the bride’s side seem empty. They just took people as far forward as they could. Mirriam was already sitting in the front row, on the opposite side of Fred’s parents. Bobby was scheduled to walk Mary down the aisle, but Mirriam was going to give her away.
A nervous and full-of-energy Florence hurried up to Bobby, as he came back from seating a family.
“She wants you to come to her dressing room now,” she said.
Bobby checked his watch. “It’s half an hour too early,” he said.
“She insisted,” said Flo. “I think she’s getting scared, or something.”
“You guys were supposed to play Scrabble with her, to distract her,” he said.
“We tried, but she wouldn’t play. She’s been pacing for ten minutes. Then she said she wanted you there.”
Bobby followed his second oldest sister to the room that had been set aside for the bride. Mary turned, when he came in.
She was so beautiful that it hurt his heart. She had offered to let her mother make her wedding dress, but Mirriam had demurred, both because it would take so long, and because, while she was quite adept at making shirts, and pants and dresses, a wedding gown was, in her opinion, beyond her skills. Carefully hoarded money had been used to buy the gown Mary was wearing. Her shoulders were bare, except for thin straps that held the bodice of the gown up. The neck scooped low enough that her cleavage showed plainly, with pearls along the edge that seemed to frame that cleavage. Her hair was done up, with pearls and tiny flowers woven through it. That had been done by Madge Carlisle, who ran the beauty shop in town. The barest hint of eye shadow, a little rouge, and a touch of lipstick were all the makeup she wore. She looked like a dream, with the exception of the anxious look on her face.
“Am I doing the right thing?” she asked instantly, when she saw him.
“Of course you are,” he said, calmly.
“You two!” she said, looking first at Bev and then Flo. “I want to talk to Bobby alone.”
“But...” Flo said, closing her mouth as Bev grabbed her elbow and pulled her toward the door.
“Just wait outside for a minute,” said Mary. “Don’t let anybody bother us.”
“Gotcha,” said Bev, a half smile on her face.
When the door closed, Mary didn’t move. “I feel so scared,” she said.
“It’s normal,” said Bobby.
“Make me feel better, Bobby,” she said.
He smiled. “Sweetheart, you’re getting married in half an hour. You’re in your wedding dress. You have makeup on.”
“You can just lift my dress,” she said. “I’m so nervous, Bobby. I’ll screw everything up!”
“Come on, Mary,” he said, softly. “You can do this.”
“I needed you last night,” she moaned. “But Mamma kept me up, and then Flo wanted to talk. Please, Bobby. One last time. We won’t be able to do it after I get married, and you always calm me down so well.”
“You can’t lie down in that dress,” he said. “And you can’t take it off either.”
“I’m going crazy!” she hissed. “Isn’t there another way?”
Bobby thought of the other ways he’d taken women. He’d never done Mary that way, but it might work.
“Put your hands on the back of that chair, and bend over,” he said.
She did, and he walked behind her, to lift the voluminous folds of the dress and lay them on her back, exposing her garter belt, and the panties that went on over it. He pulled the panties down, and she stepped out of them delicately, leaving her butt bare. Her pussy peeked out from between her legs.
Bobby unzipped. Seeing her like that had gotten him started, and all he had to do was stroke it a few times, and he was straight and hard. Putting one hand on her hip, he stepped up and held his prick to her pussy lips. She was already wet, and he slid in effortlessly.
“Ohhhhh yesss, that’s what I need,” she moaned, pushing her butt back at him.
He stroked a few times, holding her hips.
“It feels different,” she sighed. “It feels good, but I don’t think I can cum this way.”
Bobby knew he couldn’t reach her clit, and still thrust into her.
“I’m going to pull your top down just enough to get to your breasts,” he said.
She helped, sliding one strap off her shoulder, while he did the other. Her breasts fell free of the built in bra that lined the bodice of the dress, and hung, as he fondled them. Finding her nipples, he squeezed and pulled at them, fucking strongly.
“Oh yessss,” she whined. “That’s going to do it Bobbeeeeee.”
He pounded her and tortured her nipples until he felt her pussy start spasming and she moaned that she loved him. He couldn’t resist giving her one last load of brother-spunk, and held himself in her deeply as he spurted five strong jets of sperm into her.
“Don’t move,” he said, pulling out. He put himself away first, and then stooped to get her panties back on, and pulled them up. Then he told her to stand up, and she turned to face him, letting him put her breasts back in her gown, and straighten the straps.
“I want to kiss you,” she said, her eyes full of passion. “It would mess up my lipstick, though.”
“I know,” he said. He looked at his watch. “It’s almost time.”
“I’m going to miss you,” she said, looking at him coyly.
“You’re going to get fucked three times a day, if not more, for the next week,” he said grinning. “I don’t think you’ll miss me a bit.”
“I’m going to do all the things to him that you taught me,” she said.
“Go slowly,” he cautioned. “Just tell him what you like, when he does it. You can think up new things to try as time goes on.”
There was a tapping knock on the door.
“Mary!” came Flo’s tense voice.
Mary opened the door, and took Bobby’s arm. She smiled, at Flo’s anxious face. Bev was just smiling.
“I told her not to worry,” said Bev, winking.
“I’m fine, now,” said Mary. “Bobby always knows how to calm me down.”
They walked to the double doors that led into the hall. One of the ushers made a sign, through the door, and the piano player began to play the music. Flo went first, and then Bev. Fred’s niece, a three year old girl, skipped down the aisle, to stop and dump her basket of rose petals, instead of throwing them a few at a time, and the congregation laughed. There was no ring-bearer, and the music changed.
With a smile on her face, and her brother’s sperm soaking into her womb, the bride stepped lightly down the aisle, her eyes pinned on Fred Brogan, who was grinning like an idiot. All Bobby felt, as she left him, was a quick squeeze on his biceps, and she stepped to stand by Fred.
Bobby sat down by his mother, and watched his oldest sister get married.
Prudence requested that he escort her home. When they got there, she hugged him, as well as she could.
“Weddings always make me so horny,” she moaned, unbuttoning her new dress. She laid it carefully on the bed, and turned to find Bobby naked, his prick standing out in salute to her.
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