Second Chance

"Wow, James, you and mom sure had some tricks up your sleeve. And in her ass too," as she gazed at him dreamily and they kissed again.

They eventually got up and took a long shower together, rinsing off all the sweat and cum from their trysts. This wasn't like one of those porn stories though, where the guy can come 5 times consecutively. James always needed time to recover before he could get hard again, even when he was younger. They had breakfast and then Chelsea said, "what are our plans today?"

"Well, it is going to be very warm, so let's go for a swim in the lake. I have a little beach and private dock with my boat there."

"That is a great idea. But I didn't bring a bathing suit with me."

He smiled at her.

"Let me guess, you still have a bikini from mom," as she grinned at him. She went into the closet and sure enough found a string bikini that was in one of the pictures. It was a beautiful flowered pattern. A little faded and out of date, but she didn't care. She put it in on and came out the bedroom, and James nearly fainted. Chelsea again looked like her mom from 30 years ago. They went down to the dock and got into his boat. They took it for a spin around the lake and came back in an hour and docked it. They walked to the beach from the dock and went into the water for a swim, then laid out towels so they could sunbathe and dry off.

After a while, James reminisced in his mind about the times he spent on the beach with Chelsea's mom and he started developing a tent in his bathing suit. He rolled over to face Chelsea, who had her eyes closed as she sunbathed and whispered in her ear. "This reminds me of days when we would find a deserted beach and make love."

He suddenly pulled her bikini bottoms down to her ankles and pulled up her bikini top over her breasts.

"James, no. Someone will see us. We can't have sex in public. You've gone too far. I won't do this."

He rolled her over on her stomach and held her down and took off her bikini. "I am not asking you I am telling you. Your mom did it in public many times when I made her do it." She just wanted him to finish quickly and hopefully the neighbors wouldn't see. "Get up on your hands and knees."

Chelsea grudgingly did what she was told. He pulled off his trunks and started massaging her breasts which were hanging down and she started getting aroused. "I don't care if anyone sees us. I want everyone to see that we belong together."

Chelsea was worried that James was flashing back that he was with her mother, not her, and felt a little jealous. She was getting wet though thinking about how her mother had felt when he took her in a public place. She didn't have long to think about it though, as she felt his hard cock suddenly spear into her pussy. As he slapped against her butt over and over as he took her from behind, she didn't care anymore about the neighbors.

He stopped and pulled out and she was puzzled. He moved around in front of her and told her to open her moth, which she did. She wanted to claim that magnificent dick for hers to own. "Chelsea you had one more orgasm than me. You owe me one."

She opened her mouth, but said, "don't cum in my mouth. I don't do that with guys."

"Chelsea, I thought we had an understanding. Your mom would suck my cock and I would cum in her mouth at the end. She would open her mouth to show me my cum and then she would swallow it and show me her mouth again to prove she swallowed it."

Chelsea was broken now and would do anything to please James, like her mom always did. She sucked his cock eagerly now, feeling competition with the memory of her mom. He soon came hard in her mouth and she swallowed every drop and licked her lips to show him she liked it. He patted her on the head and said, "your mom would be proud."

She was starting to get mad though that maybe James was just using her to relive his memories of 30 years ago. But she felt compelled to just do what he wanted. They went back to the house and he told her they were going to go out to dinner at a fancy restaurant. Of course, he had one of her mom's fancy dresses in the closet, which was actually a classic that was still in style. They went out to the most wonderful restaurant overlooking the lake, which she had never been to before.

They spent hours eating, drinking and talking about their lives. She told him about her disappointments in relationships, and he talked about his late wife, but in the conversations lamented about not having children, because his sperm count was too low. They thought of adopting but he was so busy with his businesses, and his late wife had a busy job as a top lawyer, so they never got around to it.

When they got home, she went to go take the dress off, but he motioned her to come over to the couch so they could watch a movie together. "James, this odd. You and my mom used to go to dinner then watch a movie in your dinner clothes?"

"Yes, it was another ritual we had. We would watch a cheesy romantic comedy movie and make fun of the dialogue and plot." He found a silly romcom on cable and put his arm around her shoulder, and she felt so safe in his arms as they watched it. A half an hour into the movie he slowly took down the straps of her dress over her shoulders and started feeling her breasts and licking her nipples as she watched the screen.

"Chelsea, we would start watching the movie but then make our own x rated version of the movie the way we wanted it to be. He then rolled her over on her side against the arm of the couch, which puzzled her. He pulled up the dress exposing her ass cheeks, since she wasn't wearing panties. He pulled out a bottle of lube he had hid in his pocket and started putting his lube covered fingers inside her ass.

She knew where this was going. "James, I told you I don't take cock up the ass. I took the small butt plug, but your dick is much thicker, and it will hurt. I don't care what my mom did with you. What are you going to ass rape me if I say no?"

"No, I am just going to take what you never gave to anyone else. Now please give yourself to me completely like a good girl."

She knew she couldn't resist him anymore and after he took down his dress pants to his knees, she got on his lap, and he entered her ass slowly. He had opened her up a lot, so it didn't hurt at all. Obviously, James had an anal fixation, since he seemed to love spanking, using a butt plug with vaginal sex, and having anal sex. She bounced up and down on him while they watched the cheesy movie, where the guy barely gets a kiss at the end of the movie.

"Chelsea, play with yourself while you give me your anal virginity."

"James, I've never done that in front of a man. It's embarrassing." She caught herself though before he could respond, telling her she had to do it. She started playing with her clit furiously as he came deep into her bowels while he massaged her breasts. She came right after him with the strongest orgasm yet. She wasn't competing with her mom anymore. If she had just met James through friends, she would be doing the same things as her mom did if he just asked her to. She now liked anal sex and hoped she had pleased him as much as she knew he wanted to please her.

After they finished, they held each other for a long time and finally got up to go to bed. As they walked to the bedroom he laughed and said, "the dry cleaner is going to wonder about these stains on our clothes."

When she woke up, she didn't see James next to her and got scared. She found and bathrobe and looked around until she found him on the deck overlooking the lake, with a full breakfast on the large dining room table. He was wearing his red silk pajamas, which she loved the look of. She was ready for a great breakfast and a day at the lake again, when he said, "Chelsea, before we eat breakfast on the deck, we need to have an appetizer. He started taking off his pajamas and he said, "take off the robe and lay on the table."

She knew she couldn't say no anymore and did what he asked. She didn't care about the neighbors anymore. She didn't care about her mom anymore. She just wanted him whenever and wherever he wanted her. She took off the robe and sat on the table, next to her breakfast, which was now getting cold, but she didn't care. He got on top of her and they didn't have sex; they made love, in many different positions. They knew they had found something special and didn't want to let it go.

Chelsea moved in the next week, and she knew they only had three months until the end of the summer, when her 30th birthday would come on Labor Day, and then she would have to leave for her new job 500 miles away. She didn't want to have a long-distance relationship, but also wanted a career.

They had a happy, passionate and bit of a kinky relationship, but one day Chelsea started getting upset, which surprised him. She started sobbing and finally cried out, "I feel like I am competing with my mother. She's gone and I only have memories of her, but your memories of your time with her is all you have. You don't care about me. I am just a clone of her!"

"Chelsea, that is not true. Maybe it was that way in the very beginning, but knowing you now, you are your own person, not a clone of your mother. You may look like her, but you are unique and special to me in your own way. When we are together, I am with you, not your mom."

She felt better and they enjoyed the summer together. James had executives managing his various companies, so he only had to work part time and told Chelsea about what each company was currently working on.

When Chelsea' 30th birthday came on Labor Day, they were both sad that they would soon have to part and weren't sure what would happen to their relationship. James took her out to a dinner again at the restaurant they had enjoyed earlier in the summer, and when they returned they watched a cheesy romcom and made their own x rated version while they watched it, and laughed while they were doing it.

Afterwards James told her he had something to tell her and Chelsea dreaded that he might tell her that he was breaking up with her.

"Chelsea, I have something to tell you that you should know, although you might think bad of me after I tell you."

"What is it?" she asked worriedly.

"I was the one who paid your private school tuition all these years."

Chelsea was shocked. "why would you do that? I'm not your daughter."

"I couldn't have a child with your mother and wanted to be married to her and have one but couldn't do either. When I saw pictures of you and heard about your life, I was worried that they would never have enough money for you to get a good education, because they would waste all their money, which they ended up doing. I held the tuition funds in trust and paid the bills myself directly."

"Why didn't anyone tell me this when I was growing up?"

"Because your mother and I didn't want my wife to know, because she might wonder if I was cheating on her with your mother, which was not the case."

"James, why didn't tell me when you first met me?"

"Because I didn't want you to feel obligated to me because of money and wanted you to love me for I am, not for what I did for you."

"I understand. But I would have fallen in love with you either way, but now you know my love is true and not about what I didn't even know you did for me. I want to make my own way on the world, and since I am leaving you don't have to be concerned that I am just after your money."

"Chelsea, I would never ever think that. I have something else to tell you."

"I am really afraid to hear this. I am still trying to process what you just told me."

"I was afraid that your parents would go broke even after I paid for your tuition, so I set up a trust for you that you would be able to draw on once you turned 30 years old."

Chelsea was speechless. "Why would you do that?"

"When I saw through the pictures and emails from your mom what you had accomplished, I knew you might need help after you mom passed. I knew she was sick, but she never told me she was terminally ill. I knew she had probably built up debts you might need to pay. I was going to have her tell you when you turned 30 but she passed before that."

He took out a bank statement and showed her the amount of money in the trust and was astonished. It was enough that she would never have to work, but she didn't want that.

"James, this is generous of you, but I can't accept this."

"Chelsea, my company's general counsel could use some help managing some of my businesses, and she could give you great training to be a lawyer. I wouldn't be giving you anything, the yearly payments would just be equivalent to a market rate salary for a lawyer who also has an MBA and some experience. You could stay here with me."

"James, I would love that more than anything."

"But there is one thing. We won't be able to have children of our own but could adopt one."

"Well I have something I was going to tell you too."

"Chelsea, what is it?

"I'm pregnant. Your sperm count may be low but maybe I willed them to swim better because they really wanted to get to my egg. You're not the only one who won't take no for an answer. I want to have a family with you and spend our lives together."

"But Chelsea, don't you think I am too old for you?"

"I don't feel that way and your sperm don't think so either. You have more sexual energy with me than guys my own age. But from now on sometimes I want to give the orders in bed, and you can't say no."

"You are a tough negotiator, but I agree Chelsea. I promise."

Chelsea's mom's spirit saw this scene from the other side and smiled that they had both gotten the second chance at love they both deserved. Her spirit laughed to herself that Chelsea and James had together created the most unrealistic romcom a writer could ever dream up, patching together every cliché imaginable, except every scene was true. In a good romcom, there is always conflict between the two, but the guy always gets the girl in the end. Sometimes in the rear end.

They looked at each other and he hoped they would have a great evening of wild sex. She slowly turned to him and said, "now wait here James, I have a special treat for you, but you have to close your eyes while I put my mom's nightgown on. Go put on your pajamas too. Mom told me about everything you guys did, and there is one thing you never did with her. You have to promise though you will do whatever I want."

"I promise Chelsea."

He waited patiently but nervously with his eyes closed. He tried to remember what Chelsea's mom had done with him and what they hadn't done. He thought they had done everything a man and woman can do with other. Maybe Chelsea was going to suggest a threesome? He never did that with Chelsea's mom.

Chelsea came out of the bedroom and walked over to the couch and sat down. She said, "now open your eyes and come over to me."

He opened his eyes and saw her in the nightgown and walked over to her excitedly.

"Now pull down your pajama bottoms and get over my knee."

He didn't question her and just smiled and obediently got over her knee and thought he knew what was coming next. As she softly spanked his bottom, he reached for her pussy, expecting something warm and wet. He felt something weird though. He looked over to her as she opened her legs and pulled up her nightgown revealing what she had tucked down between her legs. He was horrified to see a strap on dildo between her legs.

"Chelsea no. I won't do that. I am not into that. With me it is an exit only, not an entrance."

"James, turnabout is fair play they say. And you can't say no, remember?" She pulled out a bottle of lube she had hidden under the couch seat cushion and squirted some onto his now quivering asshole, and slowly stuck a finger in.

"Chelsea, please no."

"Yes James. Now tell me all the naughty things you did to me these past months. By the way, have you ever heard of a woman milking a man's prostrate?"

"Yes, Chelsea."

"I like that word yes. I am going to enjoy hearing that word a lot more from you."

"I love you so much Chelsea. You can do anything to me you want to."

James winced as Chelsea pulled her finger out of his ass. "Now get down on all fours James, like a good doggy. Time to take your punishment." She got down behind him and he knew what was going to come next. It was going to be a long night. Chelsea was right. She was not her mother. She was much kinkier than her mother and had big plans for James sexually going forward. He might not like some of her ideas at first, but she knew they would never say no to each other.

Chelsea's mother's spirit looked down on the scene with amusement. Chelsea had created her own version of a romantic comedy. This one is where instead of the guy getting the girl in the end of the movie, the girl gets the guy in the end. Sometimes in the rear end.