Disciplined For Peeping Ch 05

You might want to read the previous chapters

Ronnie, Molly, and Tony began spending more time together. Molly and Tony were really a couple now and often had sex. Ronnie was frequently included but not always. Ronnie knew this and didn't mind. She wanted the young couple to enjoy each other as a couple like she and her late husband, Walter, had.

The three frequently had dinner together and other outings such as movies, theater, and opera. Ronnie was finally recovering from Walter's death enough that she began to entertain again. Mostly it was her sister, Jane, and other friends around her age, 50 and older, but she always invited Molly and Tony. It was at one of these dinners that they met Jane. Although Jane was in her late 60s, she was still an attractive, intelligent woman. Molly and Tony got along very well with Jane.

Occasionally Ronnie would meet Molly for lunch near Molly's work place. They became quite good friends and confided in each other. The types of confidences were different for each of them because of their large age difference. It was at one of these lunches that Ronnie shared her older sister Jane's health situation and what Ronnie wanted done for her. It turned out to be an extended lunch.

Jane had an inoperable brain tumor. She was expected to live maybe a year. Ronnie was trying to fill her final year with activities and events that Jane would enjoy. The two of them had already visited New York to see Broadway shows and had taken a Mediterranean cruise. Ronnie wanted something else for Jane. Jane had been married to Stuart for 43 years before Stuart passed 3 years ago. Ronnie wanted to give Jane the opportunity to enjoy sleeping with a man again before she died. Ronnie had spoken with Jane about this, and although initially reluctant, Jane conceded that it would be wonderful for Jane. She missed the companionship of a man. But what man would they find? Ronnie had an idea. This is what she had talked to Molly about on their extended lunch. Ronnie needed Molly's permission.

That same week, Ronnie invited Molly and Tony to her house for dinner. Ronnie had a part time cook that prepared these delicious meals; Ronnie wouldn't cook for others. They all had several glasses of Ronnie's excellent wine.

The subject of Jane's condition was brought up. Ronnie said, "Tony, I need your help with something."

Tony replied, "Sure, anything. You know how much I care for you."

Ronnie wanted Tony to spend the night with Jane. Ronnie explained that she had already talked with Molly and told Molly what she wanted. Molly had thought about it for a few days and finally gave her permission.

Tony was taken aback. "I can't do that. It's you two that I want in my bed. I may even be in love with both of you."

Molly said, "Tony, think about it for a few days. I think it would be a very caring thing for you to do. You are a very sensitive man. Ronnie and I are OK with this, and it won't affect our relationship."

The most Tony would commit to was thinking about it. The dinner party soon broke up and Tony and Molly headed home.

Tony did think about it. Since Ronnie asked and Molly was encouraging him, he agreed.

Ronnie spoke with Jane and gave her Tony's contact information. Jane met with Molly for lunch and told her how grateful she was for this. Molly gave her a few hints of what Tony liked to help make their evening together go more smoothly.

Tony was mildly surprised when Jane called a few days later. "Tony, I would like you to come to my house for dinner and other things as soon as you have a free night. If you are still agreeable, you can spend the night and leave early the next morning." They agreed on the next Friday, so they wouldn't be hurried Saturday morning.

Tony showed up at Jane's house at the agreed time. Jane had a luxury apartment with a doorman in a high rise. Jane greeted him wearing an informal button front red dress with white polka dots, hose, and high heels. Someone must have told her that red was Tony's favorite color for women's dresses.

Jane fixed them drinks - an old fashioned for each of them. Again, one of Tony's favorites. Jane was well prepared. Jane and Tony were both nervous. No surprise there. Jane hadn't been intimate with anyone since years before Stuart had died. They sat across from each other, Jane on the sofa and Tony on one of the easy chairs facing her. Jane said, "Tony, thank you very much for this. I know what a great favor it is."

Tony started to relax. "I would say you're welcome, but being intimate with a woman as beautiful and intelligent as you is a gift." Jane knew this wasn't strictly true but appreciated hearing it just the same. Tony was going to give it his best effort. They both started to relax. Jane fixed each of them another drink.

Jane really was an intelligent woman, and they had plenty of shared interests to fill their conversation. There was a knock at the door. It was delivery from one of the nicer French restaurants in town. Raviolis aux Champignons and Filet de Boeuf "au poivre". Tarte Fine aux Pommes for dessert with a lovely port. They continued to talk over dinner.

They cleaned up, mostly shoving things in the trash or dish washer. They had more pressing items on the agenda than kitchen duties.

They retired to the living room with snifters of brandy. They sat next to each other on the sofa this time. Jane said, "Tony, please forgive me if I call you Stuart at some point in the evening. We were married for a long time, and he was the only one I was intimate with." Tony just smiled. Jane laid her right hand on Tony's left thigh and gently rubbed. Tony bent over and lightly kissed Jane on her cheek. Jane reached behind him and ran her fingers through his hair. Tony then kissed her on her lips. Jane said, "Oh, Tony. Please don't hurry. We have all night, and I don't want to forget this lovely time."

Tony kept kissing her gently, placed his right hand on her left thigh, and his left arm around her neck. Jane sighed and moaned softly. Tony started to unbutton the top button on Jane's dress. "Wait, Tony. There's no reason for us to be uncomfortable. Let's go to my bedroom."

Jane's bedroom was down the hall. Even though she lived alone, she had a king sized bed. Jane unbuttoned Tony's shirt and pulled it off him. "Relax, Tony. Older women know things about what pleases a man that younger girls don't." She kissed down Tony's chest and started to kiss and suck his nipples. She undid his belt, unzipped his pants, and pulled them down. She then pulled his pants down. Tony helped her remove his pants and place them on the chair by the bed.

Jane then eased Tony to the bed and laid him down. She took his cock in her mouth and moaned. "Oh Tony, it has been too long. Your cock is beautiful."

Jane began to lick and suck. Jane sucked each of his balls into her mouth. Clearly, she was enjoying it all. She then moved up and kissed Tony passionately, their tongues working in each other's mouth. Jane moved down and started playing with Tony's nipples. She squeezed them, rubbed her nails over them, then started to suck them. Tony started to moan. He had never had anyone pay attention to his nipples. Jane then started to bite his nipples, softly at first and then quite hard. Tony loved it. While she was biting his nipples, she started to jack his cock. Tony was afraid he would come. "Jane, I'm afraid I'll come."

Jane said, "Don't worry. We have all night. Jane moved from biting his nipples and started to suck his cock. She kept pinching his nipples hard. Jane put lube on one of her fingers and slowly pushed it into Tony's asshole. "Relax, Tony." She found his prostate and gently massaged it. Tony couldn't hold back for long and started to cum in Jane's mouth. Tony had warned her and thought she would pull back, but she didn't. She wanted to swallow his cum. When she was satiated, she moved to Tony's mouth and shared some of his cum.

Tony realized that Jane was still dressed. "Jane, this can't be much fun for you. Let me help you get undressed."

Jane was not distressed, "Oh don't worry, Tony. This is what I want. Let's get me naked."

With that, they slowly undressed Jane. She was wearing matching bra, panties, and garter belt. She had obviously worn this tonight for him. Tony hesitated so he could admire her and commented. "Jane, you are truly a beautiful woman. Thank you for this evening."

"Oh Tony. I so needed this."

With that, Tony began to slowly kiss all of Jane's body. He unclipped her bra and started to caress her breasts. He paid special attention to her nipples. From what she had done to him, he knew she liked it a little rough. He pulled off her panties and began to kiss her thighs moving to her pussy.

Jane said, "Tony, my age and health have stopped me from being wet enough. Please use the lube and fuck me."

Tony did just that. Jane didn't come. Tony was a bit concerned, but Jane said, "Don't worry. I don't think I'm able to at this point in my life. Please just sleep with me by my side."

Tony seemed to understand and stayed next to her. They both slept late. Jane awoke first and went to the kitchen to fix them breakfast. Tony came in and said, "Thank you. That was a wonderful experience. Can we meet again?"

Jane was so happy, "Yes, but we needn't have sex. I'd just like to be with you as a friend. On a business note, I also need help making my final arrangements. Ronnie had told me that one of the services you can provide is help making decisions and plans -- for a fee, of course."

Jane became Tony's only client for more than a month. He walked her through her will, final documents, funeral arrangements, power of attorney, even making a short bucket list of things she wanted to do while she was still healthy enough. Tony made it clear that she could not leave anything to him in her will.

They only had sex that one time, but they frequently slept together. Jane wanted the closeness of a man in her bed. They went to dinner together, met for lunch and just met for coffee. They talked and talked. They developed a relationship. During this period Tony spent little time with Ronnie and Molly. Something had changed in their relationship.

Jane died six months later. During her last weeks, she had moved to a care facility. She told Tony not to visit, since she wanted him to have pleasant memories of her. Tony attended the funeral and cried. He was truly going to miss her. Ronnie and Molly weren't really surprised. They knew sensitive Tony could be. That was one of the reasons they hadn't hesitated connecting Tony with Jane. But now they worried that they had pushed him too far. Were they going to lose Tony?

Ronnie and Molly tried to comfort Tony after the funeral. All Tony said was, "Please don't loan me out to anyone again." With that he left.

To be continued.