His Great Expectations

by mattwatt

Copyright© 2015 by mattwatt

Romantic Sex Story: The good and bad of his life right then caused Stewart Rainert a need to think. He'd gotten his degree and a job, found a woman in Anita Corso that he was beginning to really like, but his wonderful Uncle Ned died. Little did he suppose at that point that being Uncle Ned's only heir would so change his life. The reality of it was hard to assimilate; he turned to Anita and her son Mark to help.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Oral Sex   .


The words kind of rambled across his mind, as he sat and thought about a late breakfast. The words were 'Great Expectations'.

He smiled a rueful smile.

"Yes," he said to himself, "I remember that. We had to read it in high school, and I hated it. I always wondered if it was my fault or if it was really a bore. Hmmm, 'Great Expectations'."

He mused again and said: "Maybe that title is as appropriate as anything. I just don't know." He closed down that kind of thinking right away, simply refusing to look at his situation from such a vantage point. It was speculation that he simply wasn't interested in at all.

But his mind was in a jumble. Just the popping into his mind of that dreadful — he'd reread it and didn't like it upon re-reading it, though he did in fact like Dickens a great deal — book title 'Great Expectations' was the sign of his mental state.

There had been lately for him, for Stewart John Rainert, so much that was great and then was equally dreadful. It was hard to assimilate it all.

There was his degree. The beauty of that was certainly short lived but he was in fact now 'Dr Stewart John Rainert, PhD. He remembered the joy of that. The dissertation done; the work all finished. It had felt grand.

There wasn't much family to share it with and, apart from his wonderful Uncle Ned, it seemed like such a solitary, personal kind of triumph. But Ned was there, and the two of them had a celebration.

Ned even gave him a gift of a trip to celebrate. He told Stewart that he needed to simply pick the destination.

Stewart had been going over that information, that gift in his mind lately and he more and more thought of going to the southwest to see scenery and sites that were, up until then, only pictures in magazines and on television specials. That appealed to him.

He'd also had an agreement with his Uncle Ned. Ned had made it abundantly clear that he wanted to simply take care of the expenses of Stewart's education.

In that conversation, Stewart talked to Ned about his desire to be the 'master' of his life. He made it, he thought, totally clear that he was not spurning Ned's help. Not at all. But maybe that help could be by making sure that Stewart had a job and could afford his own way.

Ned had told Stewart at the time that that kind of attitude made sense to him.

"It speaks to me about your Mom and Dad clearly," Ned had said, and so, the two of them worked it that way.

Stewart worked for Ned at one of his plants and was able to keep his schedule, get his work done, get his education and, finally, get his PhD degree.

He had been clear and open with his praise for Uncle Ned and the help that he did indeed give.

Ned had said to him that he realized that Stewart was being 'grown up' about his future and the way he wanted his future to be.

So, Stewart had come out of the situation as Dr. Stewart Rainert, and had received an appointment to teach history at the new local Jr College. It was his starting point and a grand one, he'd thought.

He was, right then, 24 years old and was, for most of the time, a runner. He'd done some running for the track team in high school and also in college. It was simply one of his odd interests. He had a head of wavy, sandy colored hair that was under control most of the time but not always.

'But of course, ' his was mentally reminded right then, 'that was only the first part of this sweet and sour kind of reality."

Stewart acknowledged that and went on with his thinking, his assessment. The next had been Uncle Ned's stroke. It was sudden; it was unexpected and it proved to be fatal.

"Well don't you look like you're about a thousand miles away," came a soft voice at Stewart's side.

He looked up and smiled at the waitress, or, as he thought of her, at 'his' waitress.

Her name was Anita and, since he'd been coming into this restaurant for all the years that he was busy studying, he knew her well. They were, in fact, friends.

On occasions, when Anita's boy, Mark was at the restaurant, after school waiting for her, Stewart would take Mark and go do something interesting.

He smiled at Anita.

"Sorry," he said, "Wool gathering."

"Big event?" she asked.

"Oh," he said, "My Uncle Ned died a week ago and I have to sit with the lawyer and iron out his stuff."

She got a genuinely stricken look on her face, and, holding his hand, said: "I'm so sorry. I know how you've talked about that man and his willingness to help you out."

"Yes," Stewart said, "His continuous willingness to let me do these things my way. He was superb. My Momma's little brother Ned. I guess they're together again now. At least that's what I hope."

He smiled at her then and said a quick: "Sorry to be so pokey here about ordering. I'll have the number one omelet, no peppers."

She smiled: "Right a number 1 with no peppers, and I am sorry to hear about your Uncle Ned. He certainly seemed like a gem, the times that you two were in here together."

"He was," Stewart said.

Then he broke into a smile and asked: "How's my pal?"

"Mark is fine," she said, "At school now. He'll be back here this afternoon."

"Maybe I'll stop by then and see if he and I can get into some trouble together," was his next statement.

"Then I'll ground you both!" she said with a soft giggle.

"Yes, Mom," he said, holding up a hand. "I promise only wholesome things this afternoon for him and me."

"You're so nice to even consider it," she said, "To help me out in this way."

"Hey," he answered, "We're pals here!" He held her hand, as he said this.

"Yes," she agreed, "Pals."

Then she went away to put in his order, shaking her head and saying to herself: "Pals! Too bad."

It's strange that maybe the same kind of sentence was traveling across his mind just then too.

He had his breakfast and then, as she was standing again at his table, looked at his watch and said: "Oh, I have to go. Meeting with Mr Caruso, the lawyer is in forty minutes."

"Good luck with that," she said to him.

"Tell Mark that I'll be in later," he said.

"Yes, I will," was her reply, "That will make his day."

"Good," he said.

She took the time, when he stood up to pull him into a hug. It surprised him a bit but pleased him no end. The thought that was in his mind just then was how great she felt, pressed against him.

"I appreciate you taking care of my Mark," she said.

"Yes, welcome," he said, "Pals, you know."

He'd said it this time more softly, as though it were something about which he had to think.

Allowing Mark to come to the restaurant was one of the ways that Anita Corso dealt with the way her life had turned out.

Mark at that point, was nine years old. She'd had him during the first year of her marriage to Wayne Corso. Wayne had turned out to be a party person. Being married never stopped that at all.

He seemed to be pleased at first about having a son but then it, after a bit, turned out to be just one more 'ho-hum' kind of thing at home, and no big thing at that.

For Anita, Mark was always a 'big thing'.

Then Wayne was gone; gone away with friends. Gone, in fact for years, when finally Anita, to get her life ordered, had divorced Wayne for abandonment. One of the weird things in Anita's life was that Wayne was never heard from in any way again. He'd just dropped off the map, kind of.

She didn't have good work skills but didn't mind working to make her and Mark's way. The restaurant was fine for her. She liked the people for whom she worked and was popular there.

They allowed Mark to come there after school and gradually, as she met and got to know Stewart, he and Mark formed a friendship, much as she and Stewart had also. Stewart began to do things with Mark in the afternoons. It was just grand.

Despite the kind of job she had, keeping her on her feet so much of the time, Anita Corso pushed herself to work out and keep fit. It was a kind of 'pride' thing for her. She worked out a couple times a week, and with her job, that kept her in good shape.

She was, at that point in her life, 30 years old. She had red hair and, with her job and all of her workouts, kept her 120 lbs under control. With green eyes, Anita Corso, despite her name, looked like an Irish treat.


Dan Caruso greeted Stewart with a huge smile and a good handshake. They had known each other for quite a while. Dan, in addition to being Uncle Ned's lawyer, was also a good friend and the two of them would get together periodically. Stewart was frequently involved in such gatherings.

"Stewart," the smiling man said, as his secretary ushered Stewart into Dan's office.

"Mr Caruso," Stewart said, with his usual politeness.

"No, I guess not," Dan Caruso said, "It had better be Dan; I think."

"Thank you," Stewart said, "Dan it is then."

"Sorry for our circumstances," Dan said.

"I know," Stewart agreed, "He was a great man."

"He was that," Dan agreed. "First class head for business, kind gentleman, good to his friends, very generous. That's how I always found him."

"Yes," Stewart said, "You knew him well."

They sat down then in a small seating area off in a window alcove at the side of Dan's office. Dan had, on the table there, a pile of papers that would guide their conversation.

"How have you been, Stewart?" Dan asked, once they were seated.

"Well, it's been the up and down kind of thing," Stewart said. "Just was in the process of getting used to having gotten my doctorate, when Uncle Ned had the stroke."

"Yes," Dan said, "I know how proud he was of you for that whole process."

"Yes, he allowed me to do it fairly my way," Stewart said.

"I know he struggled with that but respected your wishes in the process," Dan commented. "We talked about it a number of times."

"It was such a good feeling to know he was always there and ready to help," Stewart said.

"Well, he certainly was that," Dan replied.

"What I want to do now," Dan began, "Is explain to you what your Uncle Ned's financial situation was. You are his sole beneficiary. We've checked and there are no others with any claim on Ned's affairs."

Stewart just shook his head in agreement. That title flashed again across his mind just then, 'Great Expectations' and he banished the thought and settled down to listen.

Dan started with Uncle Ned's company, where he managed and worked. He talked to Stewart about the company's worth and it's production and bottom line situation.

"I think what we should do," Dan explained, "Is let the present management handle the company with you taking what essentially was your Uncle's salary and benefits, as the present owner. That would amount to about $175,000 a year and health benefits."

Stewart was a bit taken aback by this and showed it on his face.

Dan smiled and said: "Just hang in there with me; there is more. But how does that sound to start?"

"Fantastic," Stewart said.

"Ned and I talked about this a few times," Dan explained. "He also met with the management of the company about it. They are fine with this arrangement. I think we should also make sure that salaries are raised there to match their new management duties. The business will easily absorb that. What do you think?"

"Yes, fine," Stewart said. "That amount of money for me is more than what I could possibly need per year."

Dan smiled.

"Okay then, let's go on," Dan said.

Then Stewart discovered why Dan was smiling.

"There are the other holdings that Ned had," Dan went on. Then he described the other ventures that Ned had been a partner in or owned outright.

"We also went over these, Ned and I" Dan said. "Arrangements have been tentatively made to liquidate these assets. Ned has arranged for interested parties to make offers for these assets. By dividing the assets up, as Ned had done, and going ahead with his plans we can liquidate a great deal of what he is passing on to you. It seems like a good way to proceed."

"Yes, thank you," Stewart said.

"Apart from that there are a few minor assets that you might keep just to see how they do. I don't know how you feel about such a thing but tracking the way that they work out might be an interesting thing for you," Dan said, giving Stewart an inquiring look.

Stewart agreed. The 'minor things' that Dan was talking about were indeed ventures that Stewart felt it might just be interesting to oversee.

"Good," Dan said finally. "Then we're in broad agreement about these things?"

"Yes," Stewart said. "Dan, you're making it so easy for me."

"Well, that was Ned's plan," Dan explained, "It was almost as if he knew that something was going to happen."

"So, let me summarize," Dan said then. "We'll have the basic income for you from Ned's, now your, business of at least $175,000."

Stewart nodded his head 'yes' to that. His mind was almost at that point where it was swimming here.

"In addition, "Dan went on, "We have agreements in place to sell off this whole pile of side interests that were Ned's in toto or in which he was partnered."

Again Stewart shook his head 'yes' to this description.

"When that is accomplished, and we should have it all settled within the next two weeks. These arrangements were pretty far advanced already by the time that Ned got sick, the balance that you're looking at will be a little over 13 million dollars."

Stewart only stared at him. Then he slowly put his head in his hands.

"Ohhhh," he groaned. "I don't have any idea at all about how I can get my mind around that, around all of this."

"I know," Dan said, putting his hand on top of Stewart's. "Here's my advice: take some time to let this settle in. We'll have a meeting in a few days and go over it again. I will proceed with the arrangements that Ned already had begun and we'll get all of that in the works. You just take some time to let it become reality."

"Yes, thank you, Uncle Dan," Stewart said, lapsing into the kind of language that he'd used for this very kind man for many years, as he was growing up.

Dan Caruso smiled and said: "You're welcome, Stewart. I'll be in touch with you about all of this, and we'll review it all again. I will make sure that the money from Ned's main business will be coming to you as of tomorrow. We'll have you on that payroll. I know he has not taken that money this year yet and will see that it's all put into an account for you. I'll also get you a card to use with that account."

Stewart thanked him again, trying to let it sink in.

The two men hugged, as they parted and Stewart walked out with his mind reeling and those words 'Great Expectations' rolling around in his mind.

It was already later in the afternoon and he realized that he'd need to go and think about this. His mind was suddenly swirling with thoughts about a car, a house, trips, all sorts of ideas that he had never allowed himself to have or worry about. He closed down that kind of thinking quickly enough but realized that it certainly heralded a new kind of reality for him. But he decided that all of that was for later.

Then it was that he remembered that Mark would be at the restaurant and he'd promised to be there.

But it was another kind of quick thought that impressed his mind right away. That was that a nice dinner out with Anita and Mark was exactly the way that he wanted to begin his new kind of existence. He knew that he had to let the facts settle in and couldn't really dwell on it all or think about it yet but that seemed to him right then to be an excellent way to make a beginning.


He went to the restaurant.

She was there and he got a seat at her station. Mark was also there and joined him immediately.

"Hey, pal," he said and got an effusive greeting from Mark.

She came over and said: "Hi!" to him, with a smile.

"Coffee for me and a piece of pie," he said.

"Oh, living dangerously," was her comment.

"I certainly am, and something for my pal here," Stewart said. "He looks faint from hunger."

Mark laughed and also ordered a piece of pie.

"On me," she said but Stewart, almost out of his new kind of reality said: "No, this is my treat, thanks."

"Mr Big spender," she said with a giggle and went to get the pies.

Now Stewart was looking for a chance. The thought, the idea of taking her and Mark out to dinner had stayed in his mind and had grown to a kind of a major thing for him.

Mark went to the men's and it gave him a chance. He caught Anita's eye and she came to the table.

He began by hemming and hawing a little but settled himself down to it quickly.

"Anita, I'd like to ask you out to dinner tonight," he said softly.

She gave him big eyes but smiled.

"I'd like that," she said, with little hesitation, knowing her own mind about such things. "I would need to go home and get changed, you know, cleaned up and get someone for Mark."

"No," he interjected, "Why don't we just take him with us?"

Her smile was huge and he kind of bathed in it.

"What a guy you are," she said. "We'd love it. Where?"

It was then that Mark had returned.

"Where what?" he asked.

She said: "Stewart has asked you and me out to dinner tonight. I've said 'yes' and was wondering where he wanted to go."

"Choose," Stewart said to her.

She smiled again and said: "I hear that the chicken place out near the airport is a good one. Not too expensive either."

"No, it's totally on me," Stewart said, "Don't worry about that."

She smiled again. "Is that okay? I know Mark would like it too." Mark smiled at that a nodded his agreement.

"Fine," Stewart said, and their plans were made.

He and Mark did indeed go off then on a traipse of their own. They poked their noses into stores and specialty shops, mainly just looking around. When it was time, they returned to the restaurant and he dropped Mark off.

She told him the address of their apartment building and they made arrangements for him to pick them up in about two hours.

He himself went to his own apartment and took a shower, giving himself the chance to get ready slowly.

As he did, he thought about the apartment. This too was something that he and Uncle Ned had talked about and also agreed upon. He had his own place. Ned had said that having his own place like that was important for a young guy Stewart's age.

(As a matter of fact, selling the house and property that was Uncle Ned's, and Stewart didn't think that he wanted, had been one of the side issues that he and Dan Caruso had agreed upon that morning.)

Stewart had a supply of 'mad' money that he kept for emergencies. He stuffed all of it into his wallet, knowing that he'd have cards on the new account that Dan Caruso was establishing for him in only a day or so.

He wore a sport coat, a blazer type, with a blue shirt, whose collar was button down, with gray slacks and loafers. He looked into his mirror and approved of the way that he looked, as he set out.

His car, a vintage, Corolla, was one of the very things that his mind was now telling him that he needed to change. He also shuffled this thought off to the side, simply knowing that getting a new car was one of the things that he could now rely on. It was, for him, strange thinking.

He did make a stop on the way to Anita's for some flowers. She buzzed him in, when he rang her doorbell at her apartment building, and opened the door, when he knocked.

She was wearing a skirt and blouse with a pair of low heels. He thought that she looked lovely, and realized that he was saying that to her.

She smiled at him and gave him a hug. As they were hugging, they heard a voice coming their way.

"Hey," Mark said.

"Hi, pal," Stewart said, holding out an arm so that Mark could join the two of them in the hug.

The dinner was a super treat, especially for Anita and Mark. They were certainly doing okay, not great but okay. Anita's hard work saw to that. But excessive money or even enough money for treats out like tonight were not part of their life style. She was almost giggly about the possibility.

"This is so nice of you," Anita said to him, while they waited for Mark to be ready. She kissed his cheek, as she said it.

Stewart had also made, he realized, the decision to not do anything substantial about the money that was now his until he had a chance to see his way with Anita and Mark.

He was clear in his own mind that these were the priorities for him, and he acted on them.

He had his 'stash' of mad money that now could be used for simple daily things in a way that he wouldn't have allowed himself before. That much at least his new situation was allowing.

Dinner was slow and marvelous. Both Anita and Stewart refrained from subjects that they knew would best be handled, when Mark was not there. But for that night, going out to dinner with Mark was a treat for the three of them...

Anyone looking on would have simply marked them down for a loving family out for dinner. They at least acted that way.

During the dinner, Mark spoke openly about some of their dreams and plans.

"We're going to Rome some day," he said.

"Oh, Rome?" Stewart said, while Anita just laughed.

"We said we'd plan and save and then one day we'd get there," Mark continued.

"Why Rome?" Stewart, interested now, wanted to know.

Mark talked then about his fascination with Roman history, with Caesar and the progress of the Roman empire.

"So we made a pact, Momma and I," he explained. "We promised ourselves that we'd go to Rome some day, after saving our money and getting enough."

"Sounds like a plan," Stewart said, putting that information in the back of his mind to think about and maybe use later.

As the night went on, there was one question that was dominating Stewart's mind. He kept it there and knew that he had to act on it, ask it, before this night was finished.

He drove to Anita and Mark's apartment building and walked them to the lobby. They went upstairs together and then Anita told Mark to say 'thank you' and give them a minute.

Mark was, also, effusive in his thanks. He certainly liked Stewart and looked on him as as much of a pal as anything, and if Stewart was paying attention to his Mom, it was that much better in Mark's mind. He also opted for a hug from Stewart, before he went into the apartment.

They were left alone there and simply looking at each other. It was Anita who made the first move, putting her arms around Stewart and raising her face to kiss him.

The kiss turned out to be every possible thing that Stewart could or had ever wanted. It was a kiss to get lost in, finding the passion of it, the softness of it, the loveliness of it.

It made him sigh, when it was finished and they both smiled at each other.

Then he was ready. "Anita," he began, "I would like to do this again, often; it's what I'd like. That ... that kiss was more alive for me than anything that I've ever experienced with any woman before, ever."

She was smiling at him, as he said that.

"Yes," she said, "Let's do it again and often. I like the idea of being your girl! I just like it a lot."

They kissed again then.

"Do you have any time this weekend?" he asked.

"I work on Saturday but have Sunday off," she replied.

"How about if I make plans for me and Mark for Saturday, while you're working?" he asked.

"Lovely," she said, "But keep Sunday reserved for me and you."

"Yes," he said, liking the idea very much.


Stewart had another meeting with Dan Caruso two days later. In the meantime, he went to the restaurant for breakfast and spent some time with Mark in the afternoons each day.

He was on time for Dan Caruso and was ushered into his office.

"Let's go over all of this again," Dan said.

They did that, going over all of the details of what Ned had and bequeathed to Stewart.

There were some special items too: "Have put the house and property into the hands of a real estate agent. We've priced it low enough that I expect it to sell easily. I will contact you for your approval of any offers."

Stewart agreed to that.

(In fact the price was reasonable enough that the property sold within a month for $200,000, which was simply added to Stewart's liquid account, the account into which the money from the main business was deposited.)

Dan also indicated that the arrangements to sell off the other parts of Ned's business dealings were fairly complete and that should be taken care of quickly. They agreed that Dan would act as Stewart's power of attorney for those items.

Dan had for Stewart a new credit card and also a debit card that would draw on the account that had been established with the money from the main business and would also have the money from the house sale. It gave Stewart a good amount of liquid cash for his day to day items.

It certainly seemed to be more real this time, after their consultation and Dan mentioned, with a smile, that the end result of the negotiations and sale of side businesses would in fact amount to closer to 15 million than his previous estimation.

In the meantime, as these items were being taken car of and Stewart was becoming more aware of what his new financial situation was like, he and Anita were seeing each other regularly.

He saw her almost daily at the restaurant and doing something, after school, with Mark was becoming a main feature.

She also began to save her days off for him and whatever parts of the weekend were available to her.

Stewart dwelt on it, thought about it and came to at least an initial decision. He realized that his first priority, even before a car, was going to be where he, and he hoped, where they would live.

In his own mind, this would be the point at which Uncle Ned's goodness would become real in his life. That was his decision. He also decided that he at least wanted to talk to Anita about it. Their attachment to each other had grown and they'd become lovers, initiating a kind of relationship, that included now a physical relationship that was fairly all encompassing for them.

That evening he bought a bottle of wine. Once he'd done that, he went to her apartment. He rang the bell and she was that pleased, when he told her, over the building intercom, that it was he visiting.

She buzzed him up and opened the door, when he knocked softly.

"Hey," she said, putting her arms around his neck and kissing him, as he went into the apartment.

They remained kissing for many minutes.

She was wearing a pair of tight, black capri style pants and a tee shirt.

"You look wonderful!" he said. "And you feel wonderful." While saying this, he let his hand wander down until it was under the hem of her long tee shirt and cupping her ass cheeks.

"Bet you say that to all the girls!" she quipped, while wiggling her ass at his hand at the same time.

"No, only my Anita," he said.

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