The Life of a Prostitute

by Doris Joe

  “What can I do for you, Penny, for being so kind to me?” Paul asked.

  “I don’t know, Paul. You know, my sister and I are still living with our parents and have always talked about having a place of our own. Do you know of any partments we can rent?”

  “Of course!” he enthusiastically replied. “I know just the place. It’s close to Old Town. You would love it and I’d like to meet your sister.”

  Penny told her stepsister, Janice, all about meeting Mr. Dressler, the Davish Country Club and meeting Paul. She said Paul might have an apartment for them.

  “How much?” Janice asked.

  “I don’t know. I’ll have to ask but I think it won't be too much. Paul is a pretty good friend.”

  “How many times have you fucked him, Penny?” Janice asked.

  "Relax, Sis. He's a good guy. We’re not gonna look a gift horse in the mouth.” The apartment was out of their price range, but Paul said they only had to pay for the utilities. Paul arranged for a housewarming party after they had moved in. He invited a few of his friends that the girls were anxious to meet. Penny and Janice invited some friends of their own but Janice’s boyfriend, Aaron, was not one of them. Janice had dumped him over the DeLaurier scandal and Penny was no longer seeing Kirk.

  Paul and Mr. Dressler were there, and a few others Penny remembered from the Showstopper Gala last year. One of the men was Tyler Hawkins. Penny recognized him immediately. He was one of the men she danced with at the Gala. Penny recalled that he had a lisp. She thought it was cute. Apparently, he remembered her as well when he approached her saying, “You’re a great dancer, Penny. I’d like to do it with you again.” Only she knew he didn’t mean dancing.

  “Yes, I’d like that, Tyler,” Penny said with a smile. “Is your wife here tonight?”

  "She's home sick. Maybe you can be my surrogate wife." Coming on to him with a telling smile, she said, “Yes, and I could be her substitute.”

  Tyler shook his head in disbelief then said, “Would you mind if we talk in private, Penny?”

  "Of course," and they quietly slipped into one of their two bedrooms. The other was busy with Janice who hadn't been seen for over half an hour. “I have to be honest, Penny,” Tyler was saying. “Betty isn’t sick. The two of us aren’t getting along. I haven’t had sex for over three months and it’s driving me crazy.” Penny hugged him and expressed her sympathy. “I don’t know. I don’t know what to do but Paul said you are a compassionate girl and could help.”

  “Of course, I’d like to help. Maybe we can help each other. My sister and I are still looking for jobs and this apartment is more than we can afford.”

  “I’d like to help you with that. Just give me a chance,” and he kissed her like it was his last. There was little doubt about what he wanted and how she could help. They understood each other perfectly. The undressing was slow, deliberate and unhurried. He had his cock in her mouth; he had his lips and tongue on her cunt. They fucked just once in the missionary position, but it was a long deep fuck. She enjoyed it as much as him. They snuggled together for a while, then he said, “I don’t want to be rude, but do you mind if I leave something for you before leaving tonight. I’d feel so much better doing that.”

  Penny said nothing, just kissed him on his forehead.

  The gift was five hundred dollars. It was the first time she got paid for what she enjoyed doing. It wasn’t the last. Networking kept Penny dating a variety of men, many were married and all of them left her with a thank you gift, in cash. Tyler introduced her to Sean and Sean to Dilbert and Frank who brought Damen over for a threesome. Penny introduced Janice to Benny who introduced them to Jack, Sal, and Vince. As for Paul, he came by once a month to collect the rent by spending the afternoon with Penny or Janice, sometimes both.

  The sisters worked as a team. There was never any jealousy between them. Just because one of them was with a wealthier or a more handsome man, the girls never argued over them. They had one checking account and shared everything from clothes to the men they entertained. Over the next year, they felt like princesses. Their lives were working out better than either had ever hoped. They could now afford the best clothes, ate at the finest restaurants and had one-night stands at expensive hotels. They even talked about buying a car.

  The good times were not infinite. Paul had a heart attack one afternoon when he was fucking both girls at the apartment during his monthly visit. He lived for several more days in intensive care and died in the hospital with his wife and two sons at his side.

  Now the rent needed to be paid by the sisters. They had saved some money for a rainy day and this was indeed a rainy day. However, every hiccup isn’t life threating. There’s always a silver lining. That was how Janice and Penny met Craig and Daniel, Paul’s adult sons.

  Craig was married, Daniel was not. Daniel offered to help them with the rent on the same basis as their father. When Craig learned of the arrangement, he offered to split the cost with his brother. The arrangement was ideal for the four of them.

  The boys lacked their father’s delicate manners and could be rough at times. They soon introduced the girls to BDSM. Craig was at the apartment one night without Daniel and explained that his wife was against any type of bondage. He said before he was married, some of his girlfriends loved being submissive. His wife wasn’t one of them, so his marriage hasn’t worked out as he hoped.

  Janice was the first to agree to light bondage as long as her sister, Penny, was there in case things got out of hand. Only ropes were used to tie Janice's arms to the bed and spread her legs apart. Craig encased her with a tight breast harness, lifting them and forcing them to swell. Finally, he attached nipple clamps. Penny thought her sister looked so sexy. She couldn’t wait to try it.

  Penny stayed to watch when Craig used a Magic Wand on Janice’s clit. At first, she moaned but as the wand was turned up, Janice began to squeal and cry out with a mix of pain and pleasure. That’s when Craig covered her mouth with a ball gag. Craig’s lust was uncontrollable when he plowed into her exposed cunt. He was so excited that it took only minutes before he exploded. Penny went over to Janice giving her a kiss and told her how beautiful she looked. “Sis, you were wonderful. It’s my turn next time.”

  The next time was soon. The best nights were when the four of them partied together. It wasn't often but after meeting at the apartment, the foursome drove to the country for the weekend get-a-way. They shacked up in the small motel in a sleepy town away from the city. After a few obligatory kisses, the girls were unceremoniously undressed. The whips stung but were not painful. They didn’t mind the anal plugs and the electric shock stimulators were manageable. The nipple clamps connected with chains were a little stressful but both girls eventually got used to them.

  They were strapped together looking like Siamese twins. Penny’s left leg was attached to Janice’s right, left arm to right. The other legs were tied to the bed with legs apart. The free arms were left to explore the men’s cock and balls. Both wore ball gags with their tits snuggly wrapped with rope. Penny’s robust swollen tits turned a rosy red and Janice’s almost purple. Two immobile girls; two horny men was a recipe for an awesome orgy.

  The brothers did not need foreplay. With two shaved cunts staring at them like Cyclopes, it was all the men needed to achieve hard long stiletto-like erections. Daniel went first, sticking Janice fast and deep. Craig soon followed by thrusting his dagger into Penny. The men were not gentle as they pounded into the sisters calling the girls names they’d never been called.

  One in a raspy voice yelled, “Fuck me you filthy whore.”

  The other growled, “Squeeze my dick you dirty fucking bitch.”

  They continued by calling them sluts, degenerates, hookers, hoes and more. Like clockwork, the brothers switched sides and continued with their tirade until they satisfied themselves. Both guys collapsed leaving the sisters shackled and sore. Janice turned to Penny and said, “I guess this is what they mean by hooking up.” A few s
econds later, Penny finally caught on and giggled.

  The foursome slept until dawn, went for breakfast, and drove home. “What did you think of our little escapades?” Penny asked her sister.

  “I don’t know,” Janice answered. My arms and legs have a few bruises. My bottom is still red from the spanking and my pussy feels like someone fucked me with a bowling pin.”

  “I feel pretty much the same. Daniel was wearing a studded condom that felt great at first, but he was so rough I got a little numb. Would you do it again?” “To be honest, Sis, I didn’t mind some of it, but I wasn’t so happy being confined. I like touching and kissing and hugging, you know, a little romance before fucking a guy. What about you?” "Well, I actually had an orgasm before Craig started fucking me. There's something about being submissive and obedient that turned me on. I thought I could go on forever."

  Janice added, “It sure was memorable.”

  Penny agreed. “Yes, and it was something we’ll never forget.”

  Her sister chuckled, “You make me laugh, Penny.”

  “People keep saying I’m funny, but I don’t try to be funny.”

  “I guess you’re just a natural comic, Penny.”

  Neither of Paul’s sons called for two weeks. Daniel sent both girls an e-mail saying he was having a bachelor party for a friend. Would they like to come along?

  Janice said, “I think there’s more to this than being at a party. We better ask a few questions.”

  Daniel said, “Yes, sure you would be the only girls at the party, and we’d like you to perform for us.”

  “Perform?” Penny asked. “What are you talking about?"

  “Just a little girl to girl. You know, you’ve done it before.”

  “Yeah, but not for an audience.”

  “You did it for Craig and me.”

  “But Daniel, that was private when you guys demanded the rent.”

  “Well this is a private party and I owe my friend a favor. Can you and your sister help us out with this?”

  It was subtle but Janice understood the innuendo of helping out. The brothers helped the sisters and now it was payback time.

  “I don’t see what you mean, Janice,” Penny said after they agreed to participate in the bachelor party. “Don’t you get it, Penny? He’s saying if we don’t show up, we don’t keep the apartment.”

  “Oh, so that’s it, like blackmail,” Penny answered.

  “Yeah, kind of like blackmail.” The party was held in a renovated barn that looked like a large dancehall. There was no hay, no stalls, no animals except for the invited guests. In place of the farm implements were kegs of beer, food, tables, chairs and a hastily constructed stage. There were a few artifacts from the dairy farm, several large milk cans, a milking machine and a cattle prod.

  Penny was quickly undressed and chosen to be hooked up to the milker. Her jumbo size breasts were an ideal fit. Janice was positioned between her sister's legs to suck her clit. Much later after the party, the sisters agreed it was the best part of the evening.

  As the liquor flowed with some of the guys high on pot, their voices got louder and more insistent. They came up to the girls looking for hand jobs, then blowjobs. If the girls didn’t do as they demanded, the guys would encourage them with the prod. It was just a reminder of who was boss. Janice called the guys perverts. It had its intended effect when they shoved their dicks down their throats.

  Charles, the groom, was pushed on stage by his buddies to get a pre-honeymoon fuck. Janice said, “Fine, but only Charles. Everyone else pays $500.” Janice thought a figure that high would stop their lust. It didn’t.

  Harry Snyder, a banker, threw five hundred-dollar bills in Janice’s face, lowered his pants, pulled her close to him and pushed in, bringing howls of encouragement from the other guests. When he finished, Zak Perkins did the same. After he finished, Zak slipped off his used condom and emptied it in Janice’s mouth.

  Penny was not a spectator. Grant and Percy turned her over and DP’d her, earning the girl a quick thousand. Quick because neither man lasted long enough for Penny to get the beginnings of an orgasm. Todd Colington was different. He had a great cock and lasted so long that Penny had to endure a few splinters from her ass being rubbed on the wooden stage floor.

  The evening ended with each girl pocketing two thousand in cash. Sleep came easily to the two tired girls when they arrived back at their apartment just before sunrise. “Look, Penny,” Janice told her sister, “after last night, I kinda think we don’t need an apartment this nice or the Trimball brothers. They’re going to use us more and more. We’ve saved a little and can afford a less expensive apartment.”

  Penny frowned and said, “I like this place!”

  “I do too,” Janice said, “but I’m tired of the Trimball brothers’ and their expectations.”

  “Yeah, and I don’t like them telling us what to do,” again sounding like Gracie Allen.

  Janice rolled her eyes and said, “So, we agree.” They moved into a small cute furnished garage apartment without telling the brothers. It was in a good location, private and affordable. Their furniture was sparse, but they didn’t need much. The selling point for the girls was the large closets.

  Once settled, they registered on a couple of adult dating sites. They began hooking up almost immediately with men of all ages. Some were young horny dudes, some middle-aged men, some pensioners. More than half were married but the girls liked the pensioners best because they had the money. Most dates ended in bed and always included a gratuity.

  All went well for a few months until something dramatically changed their lives. Janice met someone. Someone she liked. Someone Janice thought was smart, considerate, and best of all, he had a sense of humor. Jordan was ten years older than her, divorced, and she thought handsome in his own way. They dated once a week, then twice, then exclusively. She moved in with him a month later.

  Penny noticed her sister wasn’t adding much to their bank account. They had to have a heart to heart. “Penny,” Janice told her sister, “I love Jordan. I want to marry him.”

  “Has he asked you?” Penny asked.

  “Not yet but I think he will.”

  “Is he rich?”

  “No but he is a CPA. Jordan is a partner at a really good company.”

  “What’s a CPA?” "He's an accountant, someone that works with money."

  “Well, that sounds great. So, he has lots of money.”

  Janice laughed and said he works with other people’s money.”

  Penny thought about that for a moment then said, “I hope you know what you’re doing.” Penny didn’t know much about love. She had never been down that road. All she remembered was a song on the oldies station that sounded like her, Don’t know much about history, don’t know much about algebra or biology. She thought it ended with maybe I can win your love. Penny began to think she could win someone’s love too.

  For a while, Penny continued with the dating site. She took a job as a stripper in the city. It helped pay the rent. She missed Janice. Penny had never been separated from her sister for so long. Some days, Penny became depressed. That’s when she decided to attend a church service. It wasn’t the Catholic church that she knew but a Lutheran church that was almost the same. It was better because she didn't need to go to confession.

  The pastor was young and handsome. He shook her hand when she left on Sunday morning. Penny went back the next Sunday and two more after that. The pastor always smiled at her when the service was over, and his handshake was warm and comforting. His name was Pastor Ronald Wilcox.

  As if it was meant to be, Penny ran into Pastor Wilcox at the local ice cream parlor. “Hello,” he said. “I’ve seen you at church, but I don’t know your name.”

  “I’m Penny Stratton.”

  “Well, it’s so nice to meet you Penny Stratton," and he said it with his characteristic smile. There was one thing different from when she saw him at church. There was a twinkle in his eyes.

&
nbsp; “Can I buy you an ice cream cone? What’s your favorite flavor?”

  “Do they have Rocky Road?” “That’s my favorite too! Two Rocky Roads coming up.” They sat at a table with their ice cream talking about nothing important. Penny wasn’t good at small talk, so she mostly listened. The attraction she felt after the church services became more powerful as the afternoon melted away.

  “Will you be at church on Sunday?” he asked. “I’m working on a sermon that will include my favorite subject, love. You might like it.” Penny was there. The sermon lasted longer than most, too long. Pastor Wilcox talked about the love of nature, parental love, love between a man and a woman, and God’s love. He told the story of Mary Magdalene and how Jesus didn’t condemn sinners. Penny only remembered what he said about men and women falling in love and the Mary Magdalene story.

  Pastor Wilcox greeted her as she left saying, “Hello again, Penny Stratton. Perhaps we’ll meet for ice cream again.”

  “Yes,” she said. “I’d like that.”

  “Monday afternoon is my ice cream day. Maybe you’ll join me.”

  “Okay, but I’m buying this time.”

  Pastor just smiled and turned to shake the hand of the next person in line. Penny’s relationship with the pastor became more serious during the weeks and months that followed. He was her soulmate, confessor, and companion. He never was judgmental and accepted her as she was. Like in his sermon, he reminded the faithful that “love is blind.” They were engaged for a year before getting married. He sister, Janice, was pregnant and her maid