During the summer following high school graduation, Penny testified for the defense saying Mr. DeLaurier was a gentleman, kind and and generous. The girls and women on the prosecution side didn't agree. That's where Penny met Mr. Dressler, at least that's what everyone in the courtroom called him. Lawyer Dressler lived in the biggest house in town, drove the nicest car and everyone knew he had money.
After DeLaurier was found guilty of a minor misdemeanor charge, Mr. Dressler asked her if she wanted a ride home. Penny gladly accepted and climbed into his Rolls-Royce. He said she was beautiful, and the chauffeur drove them to a upscale apartment.
“I thought you were taking me home,” Penny said.
“Well, this is home, my home.
“Yes, I know that but why are we here?”
“Well, I’m an acquaintance of Wendell DeLaurier’s and he told me about you. He was right. You are a lovely girl. I was thinking we might have dinner together.”
“Where?” she asked.
"My personal chief is preparing lobster thermidor in my apartment. Have you had it?”
“I’ve never had lobster. Is thermidor a special kind of lobster?”
He smiled and said, “No, Penny. It’s broiled lobster with wine sauce and cheese. You’ll love it.”
Dressler’s apartment was on the top floor overlooking the city. They walked out on the terrace watching the city’s lights come to life.
“How about a glass of wine?”
“Okay, I like wine.”
“How is Sauvignon Blanc?” he asked.
“Perfect,” she said having no clue about Sauvignon Blanc.”
But the wine was wonderful, and the lobster even better followed by cognac for an after-dinner drink. Her head was swimming when he kissed her.
“You know, Penny, my wife died two years ago, and this place is so lonely without her. Having you with me brings me back to the best times in my life. Wendell said you were a compassionate girl. I like that in a woman.”
“I guess I am compassionate,” and they both knew what that meant.
Penny stayed the night. Mr. Dressler wasn’t a great fuck but a happy fuck.
She met him for a second time a week later. They went for dinner, then a show followed by a romantic evening at his apartment. Before his chauffeur took her home, Mr. Dressler said, “I’ve got some friends that would like to meet you, Penny. Would you like that?”
“Maybe. I don’t know. Who are they?”
“Friends that I’ve known for years." He gave her a gentle kiss. "I'm having dinner with them on Thursday evening. Would you like to join us?"
“Okay, I’d like that. It would be kind of like a date, wouldn’t it?”
“I guess it would. I’ll have Colin, my driver, pick you up at six-thirty.”
Just as she was leaving, Dressler gave Penny a beautiful gold pendant with a diamond inside. "It’s what my wife wore on important occasions. Wear it on Thursday.”
Dinner was at the Davish Country Club where she met his longtime friends.
“Penny, I’d like you to meet Donna and Paul Trimball. Donna was my wife’s best friend and Paul is the executive director here at the club.”
Penny felt a little out of place being the youngest in the group but quickly felt at ease after Paul and his wife included her in the conversation. “Where will you go to college in the fall?” Paul asked.
“I’m not sure. Maybe the community college would be best for me.”
“That’s a very good choice, Penny,” Donna remarked. “It gets you to focus on what you want to do later in life.”
Penny smiled at her, but she was already doing what she wanted to do in life. The conversation gravitated to the DeLaurier trial when Paul asked, "Penny, you were at the trial. Did you know him well?"
"Only a little. I was at his home for a party and he took me out on his yacht." That was enough to get Paul interested in something other than where she would go to college. It was only a matter of time when Paul would hit on her and she could move forward with her career.
Penny didn’t need to wait long. Paul’s hand was riding up her thigh. She thought he was handsome, distinguished looking, especially with a full head of black hair and greying sideburns. They met at an exquisite hotel in the city two nights later.
She liked that he treated her like a queen. They went up to his hotel room for a quickie, then to dinner. The food and presentation were fit for royalty. They drank wine and embraced in the elevator going back to the room.
“I think I’m in love with you, Penny,” he said as he undressed her. She smiled at him but said nothing.
He wanted her to masturbate for him. She did. He wanted her to put on his cock ring and suck him. She did that too. He asked her to fuck him, cowgirl. Penny was delighted to oblige. Paul wanted anal sex. Penny didn’t object. He said she had the hottest wettest cunt he could remember. He asked if he could cum in her pussy. She agreed.
Paul took her home before his wife, Donna, would become suspicious of his late business meetings. They did it again a week later.
“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.”